1.0 2020-03-18 23:21:22 UTC 2020-09-11 20:08:57 UTC CDB006137 Choline Choline, also known as bilineurine, is an organic compound containing a N, N, N-trimethylethanolammonium cation. Choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. In plants, such as Cannabis, the first step in de novo biosynthesis of choline involves the decarboxylation of serine into ethanolamine, which is catalyzed by a serine decarboxylase. The synthesis of choline from ethanolamine involves three consecutive N-methylation steps catalyzed by a methyl transferase. In terms of human health, choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to fatty liver disease and general liver damage. This arises from the lack of VLDL , which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer. Bilineurine CHOLINE ion N,N,N-Trimethylethanol-ammonium N-Trimethylethanolamine Trimethylethanolamine Choline cation (2-Hydroxyethyl)trimethyl ammonium (2-Hydroxyethyl)trimethylammonium (beta-Hydroxyethyl)trimethylammonium 2-Hydroxy-N,N,N-trimethyl-ethanaminium 2-Hydroxy-N,N,N-trimethylethanaminium Biocolina Biocoline Cholinum Hepacholine Hormocline Lipotril N,N,N-Trimethylethanolammonium Neocolina Paresan Choline O-sulfate Citrate, choline Fagine Hydroxide, choline Vidine Bursine Chloride, choline Choline chloride Choline citrate Bitartrate, choline Choline bitartrate Choline hydroxide Choline O sulfate O-Sulfate, choline C5H14NO 104.17 104.1075 (2-hydroxyethyl)trimethylazanium choline 62-49-7 C[N+](C)(C)CCO InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 OEYIOHPDSNJKLS-UHFFFAOYSA-N belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. Cholines Organic compounds Organic nitrogen compounds Organonitrogen compounds Quaternary ammonium salts Aliphatic acyclic compounds 1,2-aminoalcohols Hydrocarbon derivatives Organic cations Organic salts Organopnictogen compounds Primary alcohols Tetraalkylammonium salts 1,2-aminoalcohol Alcohol Aliphatic acyclic compound Alkanolamine Amine Choline Hydrocarbon derivative Organic cation Organic oxygen compound Organic salt Organooxygen compound Organopnictogen compound Primary alcohol Tetraalkylammonium salt Pesticides a small molecule cholines melting_point 302 - 303 °C (chloride salt) boiling_point 113 °C Wikipedia logp -3.59 ALOGPS logs -1.59 ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 13.97 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (2-hydroxyethyl)trimethylazanium ChemAxon average_mass 104.17 ChemAxon mono_mass 104.1075 ChemAxon smiles C[N+](C)(C)CCO ChemAxon formula C5H14NO ChemAxon inchi InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 ChemAxon inchikey OEYIOHPDSNJKLS-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 42.19 ChemAxon polarizability 12.57 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00114 DB00122 FDB000710 299 305 15354 C00007298 CHOLINE Choline 33910 56 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:21:24 UTC 2020-09-11 20:08:58 UTC CDB006138 Succinic acid Succinic acid is a four-carbon acyclic dicarboxylic acid. It is a white, odorless solid with a highly acidic taste. It is used as a flavoring agent, contributing a sour and astringent component characteristic of the umami taste (PMID:21932253). The anion, succinate, is a key component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in mitochondrial function, being both part of the respiratory chain and the Krebs cycle. SDH, with a covalently attached FAD prosthetic group, is able to bind several different enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the entire Krebs cycle. Succinate can readily be imported into the mitochondrial matrix by the n-butyl malonate- (or phenyl succinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate (PMID:16143825). Human mutations in the four genes encoding the subunits of the mitochondrial succinate dehydrogenase are associated with a wide spectrum of clinical presentations, i.e.: Huntington‚Äôs disease (PMID:11803021). Moreover, succinic acid is found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Additionally, succinic acid has been identified as an oncometabolite or an endogenous cancer-causing metabolite. Oncoetabolites are metabolic intermediates whose accumulation causes a metabolic and non-metabolic dysregulation leading to tumorigenesis. (PMID:23999438, PMID:27117029). High levels of succinic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears due to its ability to inhibit prolyl hydroxylase domain-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by succinate. Succinic acid has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid is also a microbial metabolite. Indeed, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter sp., Acinetobacter sp., Proteus mirabilis, Citrobactes frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid, or its anion succinate, is used as an excipient in pharmaceutical products to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. In 2004, succinic acid was identified by the Department of Energy of the United States of America as one of twelve molecules that can be produced from plant sugars through biological or chemical processes and that have a potential to subsequently be converted to a number of high-value bio-based chemicals or materials. In this regard, industrial hemp (Cannabis sativa L.) has been identified as a source of succinic acid after several chemical and biological treatments (PMID:25682224), suggessting it could serve as a promising source of building blocks for green chemistry products. 1,2-Ethanedicarboxylic acid Acide butanedioique Acide succinique Acidum succinicum Amber acid Asuccin Bernsteinsaeure Butandisaeure Butanedionic acid Dihydrofumaric acid e363 Ethylenesuccinic acid HOOC-CH2-CH2-COOH Spirit OF amber 1,2-Ethanedicarboxylate Butanedionate Dihydrofumarate Ethylenesuccinate Succinate 2-Acetamido-2-deoxy-D-glucose D-GlcNAc N-Acetyl-D-glucosamine N-Acetylchitosamine N Acetyl D glucosamine 2 Acetamido 2 deoxy D glucose 2 Acetamido 2 deoxyglucose 2-Acetamido-2-deoxyglucose Acetylglucosamine 1,4-Butanedioate 1,4-Butanedioic acid Katasuccin Wormwood acid 1,2 Ethanedicarboxylic acid 1,4 Butanedioic acid Potassium succinate Succinate, ammonium Butanedioic acid Succinate, potassium Ammonium succinate C4H6O4 118.09 118.0266 butanedioic acid succinic acid 110-15-6 OC(=O)CCC(O)=O InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) KDYFGRWQOYBRFD-UHFFFAOYSA-N belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Dicarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound C4-dicarboxylic acid Dicarboxylic acids alpha,omega-dicarboxylic acid water_solubility 83.2 mg/mL logp -0.59 HANSCH,C ET AL. (1995) melting_point 185 - 188 °C boiling_point 235 °C Wikipedia logp -0.53 ALOGPS logs 0.25 ALOGPS logp -0.4 ChemAxon pka_strongest_acidic 3.55 ChemAxon iupac butanedioic acid ChemAxon average_mass 118.09 ChemAxon mono_mass 118.0266 ChemAxon smiles OC(=O)CCC(O)=O ChemAxon formula C4H6O4 ChemAxon inchi InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) ChemAxon inchikey KDYFGRWQOYBRFD-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 23.54 ChemAxon polarizability 10.14 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1078 DB00139 FDB001931 C00042 15741 1738118 SUC C00001205 Succinic_acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Thakker C, Martinez I, San KY, Bennett GN: Succinate production in Escherichia coli. Biotechnol J. 2012 Feb;7(2):213-24. doi: 10.1002/biot.201100061. Epub 2011 Sep 20. 21932253 Briere JJ, Favier J, El Ghouzzi V, Djouadi F, Benit P, Gimenez AP, Rustin P: Succinate dehydrogenase deficiency in human. Cell Mol Life Sci. 2005 Oct;62(19-20):2317-24. doi: 10.1007/s00018-005-5237-6. 16143825 Rustin P, Rotig A: Inborn errors of complex II--unusual human mitochondrial diseases. Biochim Biophys Acta. 2002 Jan 17;1553(1-2):117-22. doi: 10.1016/s0005-2728(01)00228-6. 11803021 Yang M, Soga T, Pollard PJ: Oncometabolites: linking altered metabolism with cancer. J Clin Invest. 2013 Sep;123(9):3652-8. doi: 10.1172/JCI67228. Epub 2013 Sep 3. 23999438 Sciacovelli M, Frezza C: Oncometabolites: Unconventional triggers of oncogenic signalling cascades. Free Radic Biol Med. 2016 Nov;100:175-181. doi: 10.1016/j.freeradbiomed.2016.04.025. Epub 2016 Apr 23. 27117029 Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. 22292465 Sauer M, Porro D, Mattanovich D, Branduardi P: Microbial production of organic acids: expanding the markets. Trends Biotechnol. 2008 Feb;26(2):100-8. doi: 10.1016/j.tibtech.2007.11.006. Epub 2008 Jan 11. 18191255 Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. 26360870 Gunnarsson IB, Kuglarz M, Karakashev D, Angelidaki I: Thermochemical pretreatments for enhancing succinic acid production from industrial hemp (Cannabis sativa L.). Bioresour Technol. 2015 Apr;182:58-66. doi: 10.1016/j.biortech.2015.01.126. Epub 2015 Feb 4. 25682224 1.0 2020-03-18 23:21:26 UTC 2020-09-11 20:08:56 UTC CDB006139 Glycine Glycine, also known as Gly or aminoacetic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Glycine is a very strong basic compound (based on its pKa). Glycine exists in all living species, ranging from bacteria to humans. Glycine is an odorless tasting compound. Outside of the human body, Glycine is found, on average, in the highest concentration within a few different foods, such as gelatins, gelatin desserts, and beluga whales and in a lower concentration in hedge mustards, pumpkinseed sunfish, and prunus (cherry, plum). Glycine has also been detected, but not quantified in, several different foods, such as boysenberries, fruit juices, giant butterburs, ginsengs, and Chinese mustards. Glycine is most important and simple, nonessential amino acid in humans, animals, and many mammals. Generally, glycine is synthesized from choline, serine, hydroxyproline, and threonine through interorgan metabolism in which kidneys and liver are the primarily involved. Glycine acts as precursor for several key metabolites of low molecular weight such as creatine, glutathione, haem, purines, and porphyrins. There are a number of reports supporting the role of supplementary glycine in prevention of many diseases and disorders including cancer. Dietary supplementation of glycine is effectual has been shown to be effective in treating metabolic disorders in patients with cardiovascular diseases ( PMID: 25332814), several inflammatory diseases, obesity, cancers, and diabetes ( PMID: 27292783). Glycine has also been shown to enhance the quality of sleep and neurological functions. (PMID: 28337245) Aminoacetic acid Aminoessigsaeure Aminoethanoic acid G Gly Glycin Glycocoll Glykokoll Glyzin H2N-CH2-COOH Hgly Leimzucker Aminoacetate Aminoethanoate 2-Aminoacetate 2-Aminoacetic acid Aciport Amino-acetate Amino-acetic acid Glicoamin Glycolixir Glycosthene Gyn-hydralin Padil Glycine carbonate (1:1), monosodium salt Glycine carbonate (2:1), monopotassium salt Glycine sulfate (3:1) Glycine, monoammonium salt Glycine, monosodium salt Glycine, sodium hydrogen carbonate Monoammonium salt glycine Calcium salt glycine Glycine hydrochloride (2:1) Glycine phosphate (1:1) Glycine, monopotasssium salt Monopotasssium salt glycine Monosodium salt glycine Glycine carbonate (2:1), monolithium salt Glycine carbonate (2:1), monosodium salt Glycine hydrochloride Glycine, copper salt Hydrochloride, glycine Salt glycine, monoammonium Acid, aminoacetic Cobalt salt glycine Copper salt glycine Glycine phosphate Glycine, calcium salt Glycine, calcium salt (2:1) Glycine, cobalt salt Phosphate, glycine Salt glycine, monosodium C2H5NO2 75.07 75.032 2-aminoacetic acid glycine 56-40-6 NCC(O)=O InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) DHMQDGOQFOQNFH-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Amino acids Common amino acids alpha-amino acid proteinogenic amino acid serine family amino acid water_solubility 249.0 mg/mL logp -3.21 HANSCH,C ET AL. (1995) melting_point 262.2 °C logp -3.34 ALOGPS logs 0.87 ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 2.31 ChemAxon pka_strongest_basic 9.24 ChemAxon iupac 2-aminoacetic acid ChemAxon average_mass 75.07 ChemAxon mono_mass 75.032 ChemAxon smiles NCC(O)=O ChemAxon formula C2H5NO2 ChemAxon inchi InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5) ChemAxon inchikey DHMQDGOQFOQNFH-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 16 ChemAxon polarizability 6.65 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00037 DB00145 FDB000484 730 750 15428 C00001361 GLY Glycine 33610 20 Razak MA, Begum PS, Viswanath B, Rajagopal S: Multifarious Beneficial Effect of Nonessential Amino Acid, Glycine: A Review. Oxid Med Cell Longev. 2017;2017:1716701. doi: 10.1155/2017/1716701. Epub 2017 Mar 1. 28337245 McCarty MF, DiNicolantonio JJ: The cardiometabolic benefits of glycine: Is glycine an 'antidote' to dietary fructose? Open Heart. 2014 May 28;1(1):e000103. doi: 10.1136/openhrt-2014-000103. eCollection 2014. 25332814 Perez-Torres I, Zuniga-Munoz AM, Guarner-Lans V: Beneficial Effects of the Amino Acid Glycine. Mini Rev Med Chem. 2017;17(1):15-32. doi: 10.2174/1389557516666160609081602. 27292783 1.0 2020-03-18 23:21:29 UTC 2020-07-22 22:11:09 UTC CDB006140 Mannitol Mannitol, also known ashexan-1,2,3,4,5,6-hexol (C6H8(OH)6), osmitrol or tobrex, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, and is produced by a plethora of organisms, including bacteria, fungi, algae, lichens, and many plants such as Cannabis (PMID:19578847). Mannitol is commonly used as a sweetener in diabetic foods as it is poorly absorbed by the intestines. Mannitol is also used as medication to decrease pressure in the eyes, (i.e. glaucoma) and to lower increased intracranial pressure. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. Mannitol can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function. Mannitol is commonly used as a research tool in cell biological studies, usually to control osmolarity. Chemically, mannitol as a sugar alcohol, is similar to xylitol or sorbitol and is considered an isomer of sorbitol. However, mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this reason, it is not uncommon to add a base to adjust its pH, such as sodium bicarbonate. Mannitol is a non-permeating molecule, meaning that it cannot cross biological membranes. Because of this inability to cross biological membranes, mannitol has been used for the determination of glomerular filtration rate (GFR). Altered levels of mannitol have been found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312; PMID: 29480337). (2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexaol (2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol D-(-)-Mannitol Dulcite e 421 e-421 e421 Manna sugar Mannite Osmitrol D-Mannitol Tobrex Bronchitol 1,2,3,4,5,6-Hexanehexol Cordycepate Cordycepic acid Diosmol Hexahydroxyhexane Hexanhexol Invenex Isotol Manicol Maniton S Maniton-S Mannazucker Mannidex Mannigen Mannistol Mannit Mannit p Mannogem 2080 Marine crystal Mushroom sugar Osmofundin Osmosal Resectisol SDM No. 35 (L)-Mannitol Mannitol C6H14O6 182.17 182.079 (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol mannitol 69-65-8 OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1 FBPFZTCFMRRESA-KVTDHHQDSA-N belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Monosaccharides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Monosaccharide Polyol Primary alcohol Secondary alcohol Sugar alcohol mannitol water_solubility 216 mg/mL at 25 °C YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -3.10 HANSCH,C ET AL. (1995) melting_point 166 °C logp -2.68 ALOGPS logs 0.10 ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 12.59 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol ChemAxon average_mass 182.17 ChemAxon mono_mass 182.079 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ChemAxon formula C6H14O6 ChemAxon inchi InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1 ChemAxon inchikey FBPFZTCFMRRESA-KVTDHHQDSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 38.4 ChemAxon polarizability 17.04 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001982 DB00742 6015 C00392 6251 16899 C00001165 MANNITOL Mannitol 142 Song SH, Vieille C: Recent advances in the biological production of mannitol. Appl Microbiol Biotechnol. 2009 Aug;84(1):55-62. doi: 10.1007/s00253-009-2086-5. Epub 2009 Jul 4. 19578847 Wisselink HW, Mars AE, van der Meer P, Eggink G, Hugenholtz J: Metabolic engineering of mannitol production in Lactococcus lactis: influence of overexpression of mannitol 1-phosphate dehydrogenase in different genetic backgrounds. Appl Environ Microbiol. 2004 Jul;70(7):4286-92. doi: 10.1128/AEM.70.7.4286-4292.2004. 15240312 Zhang M, Gu L, Cheng C, Ma J, Xin F, Liu J, Wu H, Jiang M: Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies. World J Microbiol Biotechnol. 2018 Feb 26;34(3):41. doi: 10.1007/s11274-018-2425-8. 29480337 1.0 2020-03-18 23:21:31 UTC 2020-07-22 22:11:09 UTC CDB006141 Ethanol Ethanol, also known as ethyl alcohol or alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds having a primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Ethanol is a clear, colorless liquid rapidly absorbed from the gastrointestinal tract and distributed throughout the body. It has bactericidal activity and is used often as a topical disinfectant. It is widely used as a solvent and preservative in pharmaceutical preparations as well as serving as the primary ingredient in alcoholic beverages. Indeed, ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. Ethanol has a depressive effect on the central nervous system and because of its psychoactive effects, it is considered a drug. Ethanol has a complex mode of action and affects multiple systems in the brain, most notably it acts as an agonist to the GABA receptors. Death from ethanol consumption is possible when blood alcohol level reaches 0.4%. A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1% can cause intoxication, with unconsciousness often occurring at 0.3-0.4 %. Ethanol is metabolized by the body as an energy-providing carbohydrate nutrient, as it metabolizes into acetyl CoA, an intermediate common with glucose metabolism, that can be used for energy in the citric acid cycle or for biosynthesis. Ethanol within the human body is converted into acetaldehyde by alcohol dehydrogenase and then into acetic acid by acetaldehyde dehydrogenase. The product of the first step of this breakdown, acetaldehyde, is more toxic than ethanol. Acetaldehyde is linked to most of the adverse clinical effects of alcohol. Ethanol has been shown to increase the risk of developing cirrhosis of the liver, multiple forms of cancer, and alcoholism. Industrially, ethanol is produced both as a petrochemical, through the hydration of ethylene, and biologically, by fermenting sugars with yeast. Small amounts of ethanol are endogenously produced by gut microflora through anaerobic fermentation. However, most ethanol detected in biofluids and tissues likely comes from consumption of alcoholic beverages. Absolute ethanol or anhydrous alcohol generally refers to purified ethanol, containing no more than one percent water. Absolute alcohol is not intended for human consumption. It often contains trace amounts of toxic benzene (used to remove water by azeotropic distillation). Consumption of this form of ethanol can be fatal over a short time period. Generally absolute or pure ethanol is used as a solvent for lab and industrial settings where water will disrupt a desired reaction. Pure ethanol is classed as 200 proof in the USA and Canada, equivalent to 175 degrees proof in the UK system. Ethanol is a general biomarker for the consumption of alcohol. Ethanol is also a metabolite of Hansenula and Saccharomyces (PMID: 14613880). 1-Hydroxyethane [CH2Me(OH)] [OEtH] Alcohol Alcohol etilico Alcool ethylique Alkohol Aethanol Aethylalkohol C2H5OH Dehydrated ethanol Etanol Ethyl alcohol EtOH Hydroxyethane Methylcarbinol Spiritus vini Anhydrous ethanol Absolute alcohol Absolute ethanol Absolute ethyl alcohol Alcare hand degermer Alcohols Alcool etilico Algrain Alkoholu etylowego Anhydrol Anhydrous alcohol Cologne spirit Cologne spirits Dehydrated alcohol Denatured alcohol Denatured ethanol Desinfektol el Diluted alcohol Distilled spirits Ethanol 200 proof Ethanol solution Ethicap Ethyl alc Ethyl alcohol anhydrous Ethyl alcohol in alcoholic beverages Ethyl alcohol usp Ethyl hydrate Ethyl hydroxide Fermentation alcohol Grain alcohol Hinetoless Infinity pure Jaysol Jaysol S Lux Molasses alcohol Potato alcohol Punctilious ethyl alcohol Pyro Silent spirit Spirit Spirits OF wine Spirt Synasol Tecsol Tecsol C Thanol Undenatured ethanol Alcohol, absolute Alcohol, ethyl Alcohol, grain C2H6O 46.07 46.0419 ethanol ethyl alcohol 64-17-5 CCO InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 LFQSCWFLJHTTHZ-UHFFFAOYSA-N belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Primary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic acyclic compounds Hydrocarbon derivatives Aliphatic acyclic compound Hydrocarbon derivative Primary alcohol a primary alcohol a short-chain alcohol alkyl alcohol ethanols primary alcohol water_solubility 1000.0 mg/mL logp -0.31 HANSCH,C ET AL. (1995) melting_point -114.1 °C logp -0.40 ALOGPS logs 1.10 ALOGPS logp -0.16 ChemAxon pka_strongest_acidic 16.47 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac ethanol ChemAxon average_mass 46.07 ChemAxon mono_mass 46.0419 ChemAxon smiles CCO ChemAxon formula C2H6O ChemAxon inchi InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3 ChemAxon inchikey LFQSCWFLJHTTHZ-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 13.01 ChemAxon polarizability 5.3 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00469 DB00898 FDB000753 682 702 16236 C00019560 ETOH Ethanol 35062 3203 Ryabova OB, Chmil OM, Sibirny AA: Xylose and cellobiose fermentation to ethanol by the thermotolerant methylotrophic yeast Hansenula polymorpha. FEMS Yeast Res. 2003 Nov;4(2):157-64. doi: 10.1016/S1567-1356(03)00146-6. 14613880 1.0 2020-03-18 23:21:33 UTC 2020-07-24 23:30:15 UTC CDB006142 Glucosamine Glucosamine, also known as chitosamine, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moiety. Glucosamine is a moderately basic compound (based on its pKa). Glucosamine exists in all living organisms, ranging from bacteria to humans. It is naturally present in plants, the shells of shellfish, animal bones, bone marrow, and fungi. Glucosamine is produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate and is the biochemical precursor of all nitrogen-containing sugars (PMID:11553646). In humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine-fructose-6-phosphate transaminase as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids (PMID:11553646). In the United States, glucosamine is not approved by the Food and Drug Administration for medical use in humans. Since glucosamine is classified as a dietary supplement, evidence of safety and efficacy is not required as long as it is not advertised as a treatment for a medical condition. Nevertheless, glucosamine is a popular alternative medicine used by consumers for the treatment of osteoarthritis. Glucosamine is also extensively used in veterinary medicine as an unregulated but widely accepted supplement for the treatment of osteoarthritis in companion animals. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. However, there is little evidence that any clinical effect of glucosamine works this way. Its use as a therapy for osteoarthritis appears safe but there is conflicting evidence as to its effectiveness. a-D-Glucosamine Α-D-glucosamine C6H13NO5 179.17 179.0794 (2S,3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol α-D-glucosamine 6490-70-6 N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6+/m1/s1 MSWZFWKMSRAUBD-UKFBFLRUSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds 1,2-aminoalcohols Aminosaccharides Hemiacetals Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols 1,2-aminoalcohol Alcohol Aliphatic heteromonocyclic compound Amine Amino saccharide Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organic nitrogen compound Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Primary aliphatic amine Primary amine Secondary alcohol 2-amino-2-deoxy-D-glucopyranose logp -2.175 Wikipedia melting_point 150 °C Wikipedia logp -2.73 ALOGPS logs 0.49 ALOGPS logp -3 ChemAxon pka_strongest_acidic 11.73 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac (2S,3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol ChemAxon average_mass 179.17 ChemAxon mono_mass 179.0794 ChemAxon smiles N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ChemAxon formula C6H13NO5 ChemAxon inchi InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6+/m1/s1 ChemAxon inchikey MSWZFWKMSRAUBD-UKFBFLRUSA-N ChemAxon polar_surface_area 116.17 ChemAxon refractivity 37.58 ChemAxon polarizability 16.48 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 445621 44678 Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. doi: 10.1074/jbc.R100053200. Epub 2001 Sep 11. 11553646 1.0 2020-03-18 23:21:35 UTC 2020-07-24 23:30:05 UTC CDB006143 Sorbitol Sorbitol, also known as D-glucitol or L-gulitol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone from the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally in many plants and plant products and is also produced synthetically from glucose. As an industrial chemical, sorbitol is used in the manufacturing of sorbose, propylene glycol and ascorbic acid. It is also used as a plasticizer and stabilizer for vinyl resins, urethane resins and for other rigid foams. Sorbitol also has some pharmaceutical utility. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. Sorbitol is also used as a pharmaceutical or cosmetic aid. Sorbitol is used in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, gelatins and liquid pharmaceuticals. As a food additive sorbitol functions as a sweetener, humectant, emulsifier, thickener and anticaking agent. Sorbitol is also used as a softener for candy as it acts as a sugar crystallization inhibitor (Hawley's Condensed Chemical Dictionary). As a research chemical, sorbitol is used in photometric determination of Ru (VI) and Ru(VIII) and in acid-base titration of borate (Dictionary of Organic Compounds). Sorbitol occurs widely in nature and is found in simple plants such as algae to higher order plants. Fruits of the plant family Rosacea, which include apples, pears, cherries, apricots, contain appreciable amounts of sorbitol. Particularly rich sources of sorbitol are the fruits of the Sorbus and Crataegus species. C6H14O6 182.17 182.079 (3S,6S)-3,6-dimethyltridecane (3S,6S)-3,6-dimethyltridecane 8036-93-9 OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1 FBPFZTCFMRRESA-JGWLITMVSA-N water_solubility 2750.0 mg/mL logp -2.20 SANGSTER (1994) melting_point 11 °C logp 8.09 ALOGPS logs -6.81 ALOGPS logp 6.82 ChemAxon iupac (3S,6S)-3,6-dimethyltridecane ChemAxon average_mass 182.17 ChemAxon mono_mass 182.079 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ChemAxon formula C6H14O6 ChemAxon inchi InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1 ChemAxon inchikey FBPFZTCFMRRESA-JGWLITMVSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 70.71 ChemAxon polarizability 30.34 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-18 23:21:37 UTC 2020-07-24 23:30:05 UTC CDB006144 Isocitric acid Isocitric Acid, also known as isocitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is a structural isomer of citric acid and is mildly acidic (based on its pKa). Isocitric acid exists in all living species, ranging from bacteria to humans. It is formed from citrate with the help of the enzyme aconitase and is transformed to alpha-ketoglutarate by isocitrate dehydrogenase. Outside of the human body, isocitric acid has been detected, but not quantified in, several different foods, such as red currants, wild celeries, gooseberries, soursops, and apples. This could make isocitric acid a potential biomarker for the consumption of these foods. Salts and esters of isocitric acid are known as isocitrates. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. As a result, isocitric acid is commonly used as a marker to detect the authenticity and quality of fruit products, most often citrus juices. D-Erythro-isocitric acid D-Erythro-isocitrate Isocitrate C6H8O7 192.12 192.027 (1S,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid D-erythro-isocitric acid 30810-51-6 O[C@@H]([C@H](CC(O)=O)C(O)=O)C(O)=O InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4-/m0/s1 ODBLHEXUDAPZAU-OKKQSCSOSA-N belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Tricarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Tricarboxylic acids and derivatives Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monosaccharides Organic oxides Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Hydrocarbon derivative Hydroxy acid Monosaccharide Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Tricarboxylic acid or derivatives isocitric acid melting_point 105 °C Wikipedia logp -0.35 ALOGPS logs -0.56 ALOGPS logp -1.4 ChemAxon pka_strongest_acidic 3.07 ChemAxon pka_strongest_basic -4 ChemAxon iupac (1S,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid ChemAxon average_mass 192.12 ChemAxon mono_mass 192.027 ChemAxon smiles O[C@@H]([C@H](CC(O)=O)C(O)=O)C(O)=O ChemAxon formula C6H8O7 ChemAxon inchi InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4-/m0/s1 ChemAxon inchikey ODBLHEXUDAPZAU-OKKQSCSOSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 35.72 ChemAxon polarizability 15.5 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C04617 DB01727 447805 160 Isocitric acid 1.0 2020-03-18 23:21:38 UTC 2020-08-04 22:28:39 UTC CDB006145 Methylamine Methylamine, also known as aminomethane or methanamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Methylamine is a strong basic compound (based on its pKa). It has a strong odor similar to fish. Industrially, methylamine is used as a building block for the synthesis of many other commercially available compounds. Methylamine exists in all living organisms, ranging from bacteria to humans. Methylamine is found in relatively high concentrations in a number of plant foods such as wild carrots, carrots, and tea and in a lower concentration in cabbages, corns, and barley. Methylamine has also been detected, but not quantified in, several other plant foods, such as soybeans, wild celeries, french plantains, and common grapes. It has also been detected in cow‚Äôs milk. This could make methylamine a potential biomarker for the consumption of these foods. Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. In the human body methylamine and ammonia levels are reciprocally controlled by a semicarbazide-sensitive amine oxidase activity that deaminates methylamine to formaldehyde with the production of ammonia and hydrogen peroxide ( PMID: 18845121). Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s) ( PMID: 16049393). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. This kind of deamination has been shown capable of regulating glucose transport in adipose cells. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders, and Alzheimer's disease (PMID: 18691041). The SSAO-catalyzed deamination of endogenous substrates like methylamine is known to lead to the production of toxic formaldehyde. Chronic elevated methylamine increases the excretion of malondialdehyde and microalbuminuria. Amine oxidase substrates such as methylamine have been shown to stimulate glucose uptake by increasing the recruitment of the glucose transporter GLUT4 from vesicles within the cell to the cell surface. Methylamine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Aminomethane CH3-NH2 MeNH2 Methanamine MMA Monomethylamine Anhydrous methylamine Carbinamine Imizin Mercurialin Methyl group Methyl OF gamma-N-methylasparagine Methylamine anhydrous Methylamine aqueous solution Methylamine solution Methylamine solutions Methylaminen Metilamine Metyloamina N-Methylamine NMA NME Methylamine ion (1-) Methylamine nitrate Methylamine perchlorate Methylamine sulfate (1:1) Methylamine sulfate (2:1) Methylamine, 13C-labeled Methylamine, 14C-labeled Methylamine, 15N-labeled Methylamine hydrobromide Methylamine hydrochloride, 14C-labeled Methylamine, cesium salt Methylamine, monopotassium salt Methylammonium Methylammonium ion Methylamine hydroiodide Methylamine, monosodium salt Methylamine bisulfite Methylamine hydride Methylamine hydrochloride Methylamine hydrofluoride Methylamine hydrogen cyanide Monomethylammonium ion CH5N 31.06 31.0422 methanamine methylamine 74-89-5 CN InChI=1S/CH5N/c1-2/h2H2,1H3 BAVYZALUXZFZLV-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine a small molecule methylamines one-carbon compound primary aliphatic amine water_solubility 1080 mg/mL at 25 °C logp -0.57 HANSCH,C ET AL. (1995) melting_point -93.4 °C boiling_point −6.0 °C Wikipedia logp -1.06 ALOGPS logs 1.07 ALOGPS logp -0.63 ChemAxon pka_strongest_basic 10.08 ChemAxon iupac methanamine ChemAxon average_mass 31.06 ChemAxon mono_mass 31.0422 ChemAxon smiles CN ChemAxon formula CH5N ChemAxon inchi InChI=1S/CH5N/c1-2/h2H2,1H3 ChemAxon inchikey BAVYZALUXZFZLV-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 9.92 ChemAxon polarizability 3.86 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00218 DB01828 FDB003958 6089 6329 16830 METHYLAMINE Methylamine 1800349 3767 Xiao S, Yu PH: A fluorometric high-performance liquid chromatography procedure for simultaneous determination of methylamine and aminoacetone in blood and tissues. Anal Biochem. 2009 Jan 1;384(1):20-6. doi: 10.1016/j.ab.2008.09.029. Epub 2008 Sep 25. 18845121 Pirisino R, Ghelardini C, De Siena G, Malmberg P, Galeotti N, Cioni L, Banchelli G, Raimondi L: Methylamine: a new endogenous modulator of neuron firing? Med Sci Monit. 2005 Aug;11(8):RA257-61. Epub 2005 Jul 25. 16049393 Dunkel P, Gelain A, Barlocco D, Haider N, Gyires K, Sperlagh B, Magyar K, Maccioni E, Fadda A, Matyus P: Semicarbazide-sensitive amine oxidase/vascular adhesion protein 1: recent developments concerning substrates and inhibitors of a promising therapeutic target. Curr Med Chem. 2008;15(18):1827-39. doi: 10.2174/092986708785133022. 18691041 Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. 22626821 1.0 2020-03-18 23:21:41 UTC 2020-07-24 23:30:19 UTC CDB006146 Xylitol Xylitol belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Xylitol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white crystalline solid that is soluble in water. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33% fewer calories. Xylitol is naturally found in many fruits (strawberries, plums, raspberries) and vegetables (e.g. cauliflower). Because of fruit and vegetable consumption the human body naturally processes 15 grams of xylitol per day. Xylitol is not endogenously produced by humans. Xylitol can be produced industrially starting from plant materials rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in corn, almond hulls or tree bark (or the by-products of wood: shavings hard, paper pulp). Of all polyols, xylitol is the one that has the sweetest flavor (it borders that of saccharose). It gives a strong refreshing impression, making xylitol an ingredient of choice for the sugarless chewing gum industry. In addition to its widespread use in confectionery, xylitol is also used in the pharmaceutical industry for certain mouthwashes and toothpastes and in cosmetics (creams, soaps, etc.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic (cavity-causing) bacteria and gum chewing stimulates the flow of saliva; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of dental plaque. The reduction in the amount of plaque following xylitol gum chewing within 2 weeks may be a transient phenomenon. Chewing xylitol gum for 6 months reduced Mutans streptococci levels in saliva and plaque in adults (PMID: 17426399, 15964535). Studies have also shown xylitol chewing gum can help prevent acute otitis media (earaches and infections) as the act of chewing and swallowing assists with the disposal of earwax and clearing the middle ear, while the presence of xylitol prevents the growth of bacteria in the eustachian tubes. Xylitol is well established as a life-threatening toxin to dogs. The number of reported cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening. Altered levels of xylitol have been found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism. (2R,3R,4S)-Pentane-1,2,3,4,5-pentaol Xylit Xylite Xylo-pentitol Xylitol D-XYLITOL C5H12O5 152.15 152.0685 (2R,3r,4S)-pentane-1,2,3,4,5-pentol xylitol 87-99-0 OC[C@H](O)[C@@H](O)[C@H](O)CO InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ HEBKCHPVOIAQTA-SCDXWVJYSA-N belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Monosaccharides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Monosaccharide Polyol Primary alcohol Secondary alcohol Sugar alcohol pentitol water_solubility 642 mg/mL melting_point 93.5 °C boiling_point 345.39 °C Wikipedia logp -2.53 ALOGPS logs 0.64 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 12.76 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3r,4S)-pentane-1,2,3,4,5-pentol ChemAxon average_mass 152.15 ChemAxon mono_mass 152.0685 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@H](O)CO ChemAxon formula C5H12O5 ChemAxon inchi InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ ChemAxon inchikey HEBKCHPVOIAQTA-SCDXWVJYSA-N ChemAxon polar_surface_area 101.15 ChemAxon refractivity 32.44 ChemAxon polarizability 14.42 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB01904 FDB001134 6646 6912 C00379 17151 XYLITOL Xylitol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Haresaku S, Hanioka T, Tsutsui A, Yamamoto M, Chou T, Gunjishima Y: Long-term effect of xylitol gum use on mutans streptococci in adults. Caries Res. 2007;41(3):198-203. doi: 10.1159/000099318. 17426399 Grillaud M, Bandon D, Nancy J, Delbos Y, Vaysse F: [The polyols in pediatric dentistry: advantages of xylitol]. Arch Pediatr. 2005 Jul;12(7):1180-6. doi: 10.1016/j.arcped.2005.01.032. 15964535 1.0 2020-03-18 23:21:42 UTC 2020-07-24 23:30:05 UTC CDB006147 Pentanal Pentanal, also known as amyl aldehyde or N-valeraldehyde, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R) C(=O) H, where R is any organic group. Pentanal is considered to be a fatty aldehyde lipid molecule. These are compounds containing more than one aldehyde group. Pentanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is found in a number of plant-based foods including olive oil and several essential oils. It is also present in Bantu beer, plum brandy, cardamom, coriander leaf, rice, Bourbon vanilla, clary sage, cooked shrimps, scallops, apple, banana, sweet cherry, blackcurrant, black walnuts, carrots and in a lower concentration in corns, tortilla, and safflowers. Pentanal has also been detected, but not quantified in, evergreen blackberries, soybeans, and green beans. This could make pentanal a potential biomarker for the consumption of these foods.. Pentanal is an almond, berry, and bready tasting compound and is widely used in flavorings. Its aroma is described as fermented, bready, fruity, nutty, berry. Industrially, pentanal is used in resin production and as a rubber polymerization accelerator. Pentanal is produced in human tissues and cells through lipid peroxidation. Pentanal potentially inhibits tubulin polymerization. In particular, it has been shown that purified tubulin incubated with pentanal exhibits a tubulin-aldehyde interaction affecting its polymerization reaction and the colchicine-binding activity (PMID: 3608101). Amyl aldehyde Amylaldehyde N-Pentanal N-Valeraldehyde Pentyl aldehyde Valeral Valeric aldehyde Valeryl aldehyde Valerylaldehyde 1-Pentanal Butyl formal FEMA 3098 N-C4H9CHO N-Valeraldehyde, 8ci N-Valeric aldehyde Pentan-1-al Pentanal (valeraldehyde) PNO Valeraldehyde Valerianic aldehyde Valeric acid aldehyde Pentylaldehyde Pentanal C5H10O 86.13 86.0732 pentanal pentanal 110-62-3 CCCCC=O InChI=1S/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 HGBOYTHUEUWSSQ-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. Alpha-hydrogen aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Short-chain aldehydes Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Organic oxide Short-chain aldehyde Fatty aldehydes an <i>n</i>-alkanal fatty aldehyde water_solubility 11.7 mg/mL at 25 °C melting_point -92 °C boiling_point 103 °C Wikipedia logp 1.41 ALOGPS logs -0.76 ALOGPS logp 1.21 ChemAxon pka_strongest_acidic 17.82 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac pentanal ChemAxon average_mass 86.13 ChemAxon mono_mass 86.0732 ChemAxon smiles CCCCC=O ChemAxon formula C5H10O ChemAxon inchi InChI=1S/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 ChemAxon inchikey HGBOYTHUEUWSSQ-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 25.55 ChemAxon polarizability 10.32 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB01919 7772 8063 PTL FDB003228 84069 CPD-9053 Pentanal Miglietta A, Gabriel L, Gadoni E: Microtubular protein impairment by pentanal and hexanal. Cell Biochem Funct. 1987 Jul;5(3):189-94. doi: 10.1002/cbf.290050306. 3608101 1.0 2020-03-18 23:21:44 UTC 2020-11-04 16:20:29 UTC CDB006148 Vanillic acid Vanillic acid, also known as vanillate, belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Vanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. A√ßa√≠ oil is particularly rich in vanillic acid (1,616 ¬± 94 mg/kg). Vanillic acid is also found in wine and vinegar.Vanillic acid is a metabolic by-product of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'-nucleotidase activity (PMID: 16899266). Vanillic acid is also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072, 10543794, 11728709, 9579070). 4-HYDROXY-3-methoxybenzoATE 4-HYDROXY-3-methoxybenzoic acid Vanillate Vanillic acid C8H7O4 167.14 167.0344 4-hydroxy-3-methoxybenzoate 4-hydroxy-3-methoxybenzoate 6746-48-1 COC1=CC(=CC=C1O)C([O-])=O InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)/p-1 WKOLLVMJNQIZCI-UHFFFAOYSA-M belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. M-methoxybenzoic acids and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Hydroxybenzoic acid derivatives Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives Organic anions Organic oxides Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Hydroxybenzoic acid M-methoxybenzoic acid or derivatives Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound an aromatic carboxylate methoxybenzoate monohydroxybenzoate melting_point 210 - 213 °C Wikipedia logp 1.04 ALOGPS logs -1.00 ALOGPS logp 1.17 ChemAxon pka_strongest_acidic 4.16 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 4-hydroxy-3-methoxybenzoate ChemAxon average_mass 167.14 ChemAxon mono_mass 167.0344 ChemAxon smiles COC1=CC(=CC=C1O)C([O-])=O ChemAxon formula C8H7O4 ChemAxon inchi InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)/p-1 ChemAxon inchikey WKOLLVMJNQIZCI-UHFFFAOYSA-M ChemAxon polar_surface_area 69.59 ChemAxon refractivity 52.6 ChemAxon polarizability 15.34 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB02130 23199 16632 Vanillic acid Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. doi: 10.1016/j.toxicon.2006.06.017. Epub 2006 Jul 7. 16899266 Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. doi: 10.1007/s002530000431. 11152072 Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. 10543794 Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. 11728709 Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology. 1998 Apr;144 ( Pt 4):965-73. doi: 10.1099/00221287-144-4-965. 9579070 1.0 2020-03-18 23:21:46 UTC 2020-08-04 22:28:39 UTC CDB006149 Farnesol Farnesol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive (5-carbon) isoprene units. Thus, farnesol is considered to be an isoprenoid lipid molecule. Farnesol pyrophosphate (formed by the reaction of geranyl pyrophosphate reacts with isopentenyl pyrophosphate) is the building block of all acyclic sesquiterpenes. Two sesquiterpenes are paired to form squalene (a 30-carbon terpenoid), which is the precursor for all steroids in plants, animals, and fungi. Farnesol is a very hydrophobic molecule, practically insoluble in water but miscible with oil. Under standard conditions, it is a colorless liquid. Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam and tolu. It is widely used in perfumery to emphasize the odors of sweet floral perfumes. In addition to being a perfuming agent, farnesol is a natural pesticide for mites and is a pheromone for several other insects. It also exhibits anti-microbial activity. In fact, farnesol is used as a deodorant in cosmetic products because of its anti-bacterial activity (PMID: 18492144). Farnesol has also been shown to function as a chemopreventative and anti-tumor agent through the inhibition of phosphatidylcholine biosynthesis, the induction of apoptosis, inhibition of cell cycle progression and actin cytoskeletal disorganization (PMID: 19520495). These actions appear to be mediated through farnesol‚Äôs regulation/inhibition of 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase and CTP:phosphocholine cytidylyltransferase alpha (CCTalpha). HMG-CoA is the rate-limiting enzyme in the mevalonate pathway and CCTalpha is the rate limiting enzyme in phosphatidylcholine biosynthesis (PMID: 19520495). Farnesol has also been shown to activate the farnesoid receptor (FXR), a nuclear receptor that forms a functional heterodimer with RXR (Retinoic X receptor). The physiological ligand for FXR remains to be identified; farnesol, may simply mimic the unidentified natural ligand(s). A possible metabolic fate for farnesol is its conversion to farnesoic acid, and then to farnesol-derived dicarboxylic acids (FDDCAs), which would then be excreted in the urine. Farnesol can also be oxidized to a prenyl aldehyde, presumably by mitochondrial or peroxisomal alcohol dehydrogenases (ADH). Liver endoplasmic reticulum and peroxisomal fractions are able to phosphorylate farnesol to farnesyl diphosphate in a cytosine triphosphate (CTP) dependent fashion. (PMID: 9812197, 8636420, 9083051, 9015362). (2-cis,6-cis)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol (Z,Z)-Farnesol cis,cis-Farnesol FARNESOL C15H26O 222.37 222.1984 (2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol (Z,Z)-farnesol 16106-95-9 CC(C)=CCC\C(C)=C/CC\C(C)=C/CO InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9-,15-11- CRDAMVZIKSXKFV-FBXUGWQNSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Fatty alcohols Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Farsesane sesquiterpenoid Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Sesquiterpenoid Acyclic farnesane sesquiterpenoids farnesol boiling_point 283 - 284.00 °C Wikipedia logp 4.84 ALOGPS logs -3.58 ALOGPS logp 4.16 ChemAxon pka_strongest_acidic 16.33 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)=CCC\C(C)=C/CC\C(C)=C/CO ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9-,15-11- ChemAxon inchikey CRDAMVZIKSXKFV-FBXUGWQNSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 74.98 ChemAxon polarizability 28.64 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB02509 1549107 42680 Farnesol Kromidas L, Perrier E, Flanagan J, Rivero R, Bonnet I: Release of antimicrobial actives from microcapsules by the action of axillary bacteria. Int J Cosmet Sci. 2006 Apr;28(2):103-8. doi: 10.1111/j.1467-2494.2006.00283.x. 18492144 Joo JH, Jetten AM: Molecular mechanisms involved in farnesol-induced apoptosis. Cancer Lett. 2010 Jan 28;287(2):123-35. doi: 10.1016/j.canlet.2009.05.015. Epub 2009 Jun 10. 19520495 Edwards PA, Ericsson J: Signaling molecules derived from the cholesterol biosynthetic pathway: mechanisms of action and possible roles in human disease. Curr Opin Lipidol. 1998 Oct;9(5):433-40. doi: 10.1097/00041433-199810000-00007. 9812197 Roullet JB, Xue H, Chapman J, McDougal P, Roullet CM, McCarron DA: Farnesyl analogues inhibit vasoconstriction in animal and human arteries. J Clin Invest. 1996 May 15;97(10):2384-90. doi: 10.1172/JCI118682. 8636420 Bostedor RG, Karkas JD, Arison BH, Bansal VS, Vaidya S, Germershausen JI, Kurtz MM, Bergstrom JD: Farnesol-derived dicarboxylic acids in the urine of animals treated with zaragozic acid A or with farnesol. J Biol Chem. 1997 Apr 4;272(14):9197-203. doi: 10.1074/jbc.272.14.9197. 9083051 Westfall D, Aboushadi N, Shackelford JE, Krisans SK: Metabolism of farnesol: phosphorylation of farnesol by rat liver microsomal and peroxisomal fractions. Biochem Biophys Res Commun. 1997 Jan 23;230(3):562-8. doi: 10.1006/bbrc.1996.6014. 9015362 1.0 2020-03-18 23:21:47 UTC 2020-07-24 23:30:19 UTC CDB006150 Sucrose Sucrose or table sugar is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane (Saccharum officinarum), sugar beet (Beta vulgaris), and other plants and is used extensively as a food and a sweetener. Sucrose is derived by crushing and extracting sugarcane with water or by extracting sugar beet with water, evaporating, and purifying with lime, carbon, and various liquids. Sucrose is also obtainable from sorghum. Sucrose occurs in low percentages in honey and maple syrup. Sucrose is used as a sweetener in foods and soft drinks, in the manufacture of syrups, in invert sugar, confectionery, preserves and jams, demulcent, pharmaceutical products, and caramel. Sucrose is also a chemical intermediate for detergents, emulsifying agents, and other sucrose derivatives. Sucrose is widespread in the seeds, leaves, fruits, flowers, and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynthesis. The annual world production of sucrose is in excess of 90 million tons, mainly from the juice of sugar cane (20%) and sugar beet (17%). In addition to its use as a sweetener, sucrose is used in food products as a preservative, antioxidant, moisture control agent, stabilizer, and thickening agent. C12H22O11 342.3 342.1162 (2R,3S,4R,5R,6S)-2-{[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol sucrose 57-50-1 OC[C@@H]1O[C@](CO)(O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12+/m0/s1 CZMRCDWAGMRECN-MTNNYNCSSA-N This compound belongs to the class of chemical entities known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. O-glycosyl compounds Chemical entities Organic compounds Organic oxygen compounds Organooxygen compounds Aliphatic heteromonocyclic compounds C-glycosyl compounds Disaccharides Hydrocarbon derivatives Ketals Oxacyclic compounds Oxanes Oxolanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound C-glycosyl compound Disaccharide Hydrocarbon derivative Ketal O-glycosyl compound Organoheterocyclic compound Oxacycle Oxane Oxolane Polyol Primary alcohol Secondary alcohol water_solubility 200 g/dL Wikipedia logp 0.0 Wikipedia logp -2.63 ALOGPS logs 0.38 ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 11.84 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4R,5R,6S)-2-{[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol ChemAxon average_mass 342.3 ChemAxon mono_mass 342.1162 ChemAxon smiles OC[C@@H]1O[C@](CO)(O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O ChemAxon formula C12H22O11 ChemAxon inchi InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12+/m0/s1 ChemAxon inchikey CZMRCDWAGMRECN-MTNNYNCSSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.77 ChemAxon polarizability 31.74 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 46936484 DB02772 Sucrose 1.0 2020-03-18 23:21:50 UTC 2020-08-04 22:28:39 UTC CDB006151 Stearic acid Stearic acid, also known as stearate or¬†octadecanoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a waxy solid and is one of the most common saturated fatty acids found in nature (being a close second to palmitic acid). The triglyceride derived from three molecules of stearic acid is called stearin.¬†Stearic acid is obtained from fats and oils by the saponification of the triglycerides, like stearin, using hot water. Stearic acid exists in all living organisms, ranging from bacteria to humans. Stearic acid has been detected, but not quantified in, several different foods, such as sweet bay, rose hips, muscadine grapes, pummelo, and garland chrysanthemums. Fats and oils rich in stearic acid are more abundant in animal fat (up to 30%) than in vegetable fat (typically <5%). The important exceptions are the foods cocoa butter and shea butter, where the stearic acid content (as a triglyceride) is 28‚Äì45%. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks. Stearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shaving cream products.¬†Fatty acids are classic components of candle-making. Stearic acid is used along with simple sugar or corn syrup as a hardener in candies. In epidemiologic and clinical studies, stearic acid was found to be associated with lowered LDL cholesterol in comparison with other saturated fatty acids (PMID:19939984).¬†Stearic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C18H36O2 284.48 284.2715 2,2,5-trimethylhexane 2,2,5-trimethylhexane 609343-71-7 CCCCCCCCCCCCCCCCCC(O)=O InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) QIQXTHQIDYTFRH-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane water_solubility 0.000597 mg/mL logp 8.23 SANGSTER (1993) melting_point 68.8 °C logp 5.05 ALOGPS logs -4.60 ALOGPS logp 4.01 ChemAxon iupac 2,2,5-trimethylhexane ChemAxon average_mass 284.48 ChemAxon mono_mass 284.2715 ChemAxon smiles CCCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C18H36O2 ChemAxon inchi InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) ChemAxon inchikey QIQXTHQIDYTFRH-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 42.98 ChemAxon polarizability 17.71 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 19041 Hunter JE, Zhang J, Kris-Etherton PM: Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: a systematic review. Am J Clin Nutr. 2010 Jan;91(1):46-63. doi: 10.3945/ajcn.2009.27661. Epub 2009 Nov 25. 19939984 1.0 2020-03-18 23:21:51 UTC 2020-07-24 23:30:05 UTC CDB006152 Pectin Pectin is a heteropolysaccharide, mainly composed by galacturonic acid. It is an extremely weak basic (essentially neutral) compound (based on its pKa). Pectin is found in the primary cell walls of terrestrial plants. Pears, apples, guavas, quince, plums, gooseberries, and oranges and other citrus fruits contain large amounts of pectin, while soft fruits, like cherries, grapes, and strawberries, contain small amounts of pectin. Pectin is produced commercially as a white to light brown powder, mainly extracted from citrus fruits. Pectin is used in food as a gelling agent, particularly in confectionery jellies to give a good gel structure, a clean bite and to confer a good flavour release. It is also used in dessert fillings, medicines, sweets, as a stabilizer in fruit juices and milk drinks, and as a source of dietary fiber. The main use for pectin is as a gelling agent. It is also used as a thickening agent and stabilizer in food. In medicine, pectin increases the viscosity and volume of stools so that it is used to prevent constipation and diarrhea. Pectin is also used in wound healing preparations and specialty medical adhesives, such as colostomy devices. (+)-Xylose 2,3,4,5-Tetrahydroxypentanal D-Lyxose DL-Xylose L(+)-Xylose L-Lyxose Lyxose Pectin sugar Pectinose Pentose Trobicin Pectinic acid Calcium pectinate Methoxy pectin Methoxylpectin Methoxypectin Zinc pectinate Galacturonate b-D-Galacturonate b-D-Galacturonic acid beta-D-Galacturonate Β-D-galacturonate Β-D-galacturonic acid Pectin b-D-Galactopyranuronate b-D-Galactopyranuronic acid beta-D-Galactopyranuronate Β-D-galactopyranuronate Β-D-galactopyranuronic acid C6H10O7 194.14 194.0427 (2S,3R,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid β-D-galactopyranuronic acid 14982-50-4 O[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6+/m0/s1 AEMOLEFTQBMNLQ-DTEWXJGMSA-N belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucuronic acid derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Oxacyclic compounds Oxanes Polyols Pyrans Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Glucuronic acid or derivatives Hemiacetal Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Organoheterocyclic compound Oxacycle Oxane Polyol Pyran Secondary alcohol D-galactopyranuronic acid logp -2.30 ALOGPS logs 0.18 ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 3.21 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3R,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid ChemAxon average_mass 194.14 ChemAxon mono_mass 194.0427 ChemAxon smiles O[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C(O)=O ChemAxon formula C6H10O7 ChemAxon inchi InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6+/m0/s1 ChemAxon inchikey AEMOLEFTQBMNLQ-DTEWXJGMSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 35.79 ChemAxon polarizability 16.37 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 390200 441476 C08348 FDB023162 DB03652 47954 34162 Pectin 6916 PECTIN 1.0 2020-03-18 23:21:53 UTC 2020-08-04 22:28:39 UTC CDB006153 Palmitic acid Palmitic acid, also known as palmitate or C16, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). In humans and other mammals, excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major lipid component of animals. In humans, one analysis found it to make up 21‚Äì30% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid has been detected, but not quantified in, several different foods, such as sea-buckthornberries, avocado, star fruits, babassu palms, and acerola. Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil triglycerides, rendered from palm trees (species Elaeis guineensis), are treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the word‚Äôs naphthenic acid and palmitic acid. Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Palmitic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 1-Hexyldecanoic acid 1-Pentadecanecarboxylic acid 16:00 C16 C16 Fatty acid C16:0 Cetylic acid CH3-[CH2]14-COOH FA 16:0 Hexadecanoate Hexadecoic acid Hexadecylic acid Hexaectylic acid N-Hexadecanoic acid N-Hexadecoic acid Palmitate Palmitinic acid Palmitinsaeure Pentadecanecarboxylic acid 1-Hexyldecanoate 1-Pentadecanecarboxylate Cetylate Hexadecanoic acid Hexadecoate Hexadecylate Hexaectylate N-Hexadecanoate N-Hexadecoate Palmitinate Pentadecanecarboxylate Edenor C16 Emersol 140 Emersol 143 Glycon p-45 Hexadecanoate (N-C16:0) Hexadecanoic acid palmitic acid Hydrofol Hydrofol acid 1690 Hystrene 8016 Hystrene 9016 Industrene 4516 Kortacid 1698 Loxiol ep 278 Lunac p 95 Lunac p 95KC Lunac p 98 Palmitoate Palmitoic acid PAM PLM Prifac 2960 Prifrac 2960 Pristerene 4934 Univol u332 Acid, hexadecanoic Acid, palmitic FA(16:0) C16H32O2 256.42 256.2402 hexadecanoic acid palmitic acid 67701-02-4 CCCCCCCCCCCCCCCC(O)=O InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) IPCSVZSSVZVIGE-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Saturated fatty acids Straight chain fatty acids Straight chain fatty acids long-chain fatty acid straight-chain saturated fatty acid water_solubility 4e-05 mg/mL logp 7.17 SANGSTER (1993) melting_point 61.8 °C boiling_point 351–352 °C Wikipedia logp 7.23 ALOGPS logs -5.80 ALOGPS logp 6.26 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac hexadecanoic acid ChemAxon average_mass 256.42 ChemAxon mono_mass 256.2402 ChemAxon smiles CCCCCCCCCCCCCCCC(O)=O ChemAxon formula C16H32O2 ChemAxon inchi InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) ChemAxon inchikey IPCSVZSSVZVIGE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 77.08 ChemAxon polarizability 34.36 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00249 960 DB03796 15756 985 FDB031084 PALMITATE C00030479 Palmitic_acid 34386 187 KINGSBURY KJ, PAUL S, CROSSLEY A, MORGAN DM: The fatty acid composition of human depot fat. Biochem J. 1961 Mar;78:541-50. doi: 10.1042/bj0780541. 13756126 Jensen RG, Hagerty MM, McMahon KE: Lipids of human milk and infant formulas: a review. Am J Clin Nutr. 1978 Jun;31(6):990-1016. doi: 10.1093/ajcn/31.6.990. 352132 1.0 2020-03-18 23:21:55 UTC 2020-08-04 22:28:39 UTC CDB006154 Cadaverine Cadaverine, also known as 1,5-diaminopentane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Cadaverine is a strong basic compound (based on its pKa). Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal and/or plant tissue. However, cadaverine is not purely associated with putrefaction. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine has been shown to bind to mammalian trace amine associated receptors TAAR6 and TAAR8 ( PMID: 29324768) and to act as a ‚Äúnecromone‚Äù triggering avoidance or attractive responses, which are fundamental for the survival of a wide range of species. Cadaverine is toxic in large doses. In rats it has a low acute oral toxicity of more than 2000 mg/kg body weight ( PMID: 9207896). Cadaverine can be naturally found in some bacterial species including Corynebacterium (PMID: 27872963). In addition many plants have been found to synthesize it. For instance, plants from the Leguminosae family have been shown to produce cadaverine and use it as a precursor in the biosynthesis of quinolizidine alkaloids. Quinolizidine alkaloids are secondary metabolites that are involved in insect defense and also display therapeutic pharmacological properties. C5H14N2 102.18 102.1157 (3R,3aS,5S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene (1R,7S,8aS)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,5,6,7,8,8a-octahydroazulene 462-94-2 NCCCCCN InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 VHRGRCVQAFMJIZ-UHFFFAOYSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 0.0 Wikipedia melting_point 9 °C boiling_point 179.1 °C Wikipedia logp 5.61 ALOGPS logs -3.97 ALOGPS logp 4.46 ChemAxon iupac (3R,3aS,5S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene ChemAxon average_mass 102.18 ChemAxon mono_mass 102.1157 ChemAxon smiles NCCCCCN ChemAxon formula C5H14N2 ChemAxon inchi InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 ChemAxon inchikey VHRGRCVQAFMJIZ-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.26 ChemAxon polarizability 26.26 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 91753506 Izquierdo C, Gomez-Tamayo JC, Nebel JC, Pardo L, Gonzalez A: Identifying human diamine sensors for death related putrescine and cadaverine molecules. PLoS Comput Biol. 2018 Jan 11;14(1):e1005945. doi: 10.1371/journal.pcbi.1005945. eCollection 2018 Jan. 29324768 Til HP, Falke HE, Prinsen MK, Willems MI: Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats. Food Chem Toxicol. 1997 Mar-Apr;35(3-4):337-48. doi: 10.1016/s0278-6915(97)00121-x. 9207896 Wendisch VF: Microbial Production of Amino Acid-Related Compounds. Adv Biochem Eng Biotechnol. 2017;159:255-269. doi: 10.1007/10_2016_34. 27872963 1.0 2020-03-18 23:21:56 UTC 2020-07-24 23:30:05 UTC CDB006155 Ergosterol Ergosterol, also known as provitamin D2, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3-beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol can be extracted and converted to vitamin D to be used as a dietary supplement and food additive. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. Because many fungi and protozoa cannot survive without ergosterol, the enzymes that synthesize it have become important targets for drug discovery. Ergosterol powder is an irritant to skin, eyes, and the respiratory tract. Ingestion of large amounts can cause hypercalcemia, which (if prolonged) can lead to calcium salt deposits in the soft tissues and, in particular, the kidneys. C28H44O 396.66 396.3392 (1R,2R,5S,11R,14S,15S)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol (1R,2R,5S,11R,14S,15S)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol 57-87-4 CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1 DNVPQKQSNYMLRS-APGDWVJJSA-N water_solubility 16 mg/mL melting_point 170 °C boiling_point 250 °C Wikipedia logp 7.39 ALOGPS logs -6.41 ALOGPS logp 6.63 ChemAxon pka_strongest_acidic 18.27 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1R,2R,5S,11R,14S,15S)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol ChemAxon average_mass 396.66 ChemAxon mono_mass 396.3392 ChemAxon smiles CC(C)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C ChemAxon formula C28H44O ChemAxon inchi InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1 ChemAxon inchikey DNVPQKQSNYMLRS-APGDWVJJSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 127.13 ChemAxon polarizability 50.1 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 46936866 DB04038 Ergosterol Li X, Wu Q, Bu M, Hu L, Du WW, Jiao C, Pan H, Sdiri M, Wu N, Xie Y, Yang BB: Ergosterol peroxide activates Foxo3-mediated cell death signaling by inhibiting AKT and c-Myc in human hepatocellular carcinoma cells. Oncotarget. 2016 Jun 7;7(23):33948-59. doi: 10.18632/oncotarget.8608. 27058618 1.0 2020-03-18 23:21:58 UTC 2020-07-24 23:30:05 UTC CDB006156 Glycerol Glycerol, also known as glycerin or glycyl alcohol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Glycerol is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses, or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously. (+)-b-Irone (+)-Β-irone C3H8O3 92.09 92.0473 (3E)-4-[(5R)-2,5,6,6-tetramethylcyclohex-1-en-1-yl]but-3-en-2-one (3E)-4-[(5R)-2,5,6,6-tetramethylcyclohex-1-en-1-yl]but-3-en-2-one 8043-29-6 OCC(O)CO InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 PEDCQBHIVMGVHV-UHFFFAOYSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Acryloyl compounds Enones Hydrocarbon derivatives Ketones Organic oxides Acryloyl-group Aliphatic homomonocyclic compound Alpha,beta-unsaturated ketone Carbonyl group Cyclofarsesane sesquiterpenoid Enone Hydrocarbon derivative Ionone derivative Ketone Megastigmane sesquiterpenoid Organic oxide Organic oxygen compound Organooxygen compound Sesquiterpenoid water_solubility 1000.0 mg/mL logp -1.76 HANSCH,C ET AL. (1995) melting_point 20 °C boiling_point 290 °C Wikipedia logp 4.29 ALOGPS logs -3.48 ALOGPS logp 3.56 ChemAxon pka_strongest_acidic 19.71 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (3E)-4-[(5R)-2,5,6,6-tetramethylcyclohex-1-en-1-yl]but-3-en-2-one ChemAxon average_mass 92.09 ChemAxon mono_mass 92.0473 ChemAxon smiles OCC(O)CO ChemAxon formula C3H8O3 ChemAxon inchi InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 ChemAxon inchikey PEDCQBHIVMGVHV-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 66.37 ChemAxon polarizability 25.15 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10219919 1.0 2020-03-18 23:21:59 UTC 2020-07-24 23:30:05 UTC CDB006157 Undecanal Undecanal, also known as undecyl aldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are aldehydes with a chain length containing between 6 and 12 carbon atoms. Thus, undecanal is considered to be a fatty aldehyde lipid molecule. Undecanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Undecanal is a sweet, aldehydic, citrus-tasting compound. It is a colourless, oily liquid frequently used in perfumes. It is produced commercially by hydroformylation of decene. Undecanal is found in a number of food products including corianders and carrots, celery stalks, wild celeries, evergreen blackberries, corns, and sweet basils. This could make undecanal a potential biomarker for the consumption of these foods. Undecanal is also found in many essential oils including citrus orange essential oil and grapefruit essential oil.. Undecanal is also a male sex pheromone used by the greater wax moth, Galleria mellonella (PMID: 24692052). N-Undecanal Undecanaldehyde Undecyl aldehyde Undecylaldehyde Undecylic aldehyde 1-Undecanal Aldehyde C-11 C11 Aldehyde FEMA 3092 Hendecanal Hendecanaldehyde N-Indecyl aldehyde C11H22O 170.29 170.1671 undecanal undecanal 112-44-7 CCCCCCCCCCC=O InChI=1S/C11H22O/c1-2-3-4-5-6-7-8-9-10-11-12/h11H,2-10H2,1H3 KMPQYAYAQWNLME-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide Fatty aldehydes fatty aldehyde melting_point -4 °C boiling_point 120 - 122 °C Wikipedia logp 4.98 ALOGPS logs -4.93 ALOGPS logp 3.88 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac undecanal ChemAxon average_mass 170.29 ChemAxon mono_mass 170.1671 ChemAxon smiles CCCCCCCCCCC=O ChemAxon formula C11H22O ChemAxon inchi InChI=1S/C11H22O/c1-2-3-4-5-6-7-8-9-10-11-12/h11H,2-10H2,1H3 ChemAxon inchikey KMPQYAYAQWNLME-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 53.15 ChemAxon polarizability 22.77 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04093 8186 46202 FDB002916 Undecanal Svensson GP, Gunduz EA, Sjoberg N, Hedenstrom E, Lassance JM, Wang HL, Lofstedt C, Anderbrant O: Identification, synthesis, and behavioral activity of 5,11-dimethylpentacosane, a novel sex pheromone component of the greater wax moth, Galleria mellonella (L.). J Chem Ecol. 2014 Apr;40(4):387-95. doi: 10.1007/s10886-014-0410-8. Epub 2014 Apr 2. 24692052 1.0 2020-03-18 23:22:01 UTC 2020-07-24 23:30:15 UTC CDB006158 Fructose Fructose, or levulose or fruit sugar, is a levorotatory monosaccharide and an isomer of glucose. The chemical formula of fructose is (C6H12O6). . As is the case with all monosaccharides, fructose is a reducing sugar. Pure fructose has a sweet taste similar to cane sugar, but with a "fruity" aroma. Although fructose is a hexose (6-carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose). This structure is responsible for the long metabolic pathway and high reactivity compared to glucose. Fructose is found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. Fructose is found in many foods and is one of the three most important blood sugars along with glucose and galactose. Honey, tree fruits, berries, melons, and some root vegetables, such as beets, sweet potatoes, parsnips, and onions contain fructose, usually in combination with sucrose and glucose. The greatest dietary sources of fructose are high-fructose corn syrup, agave nectar, honey, molasses, maple syrup, fruit and fruit juices. Fructose is also derived from the digestion of sucrose, a disaccharide consisting of glucose and fructose that is broken down by enzymes during digestion. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose. It is used as a preservative and an intravenous infusion in parenteral feeding. Fructose is a reducing sugar, as are all monosaccharides. The spontaneous addition of single sugar molecules to proteins, known as glycation, is a significant cause of damage in diabetics. Excessive consumption of fructose (especially from sugar-sweetened beverages) may contribute to insulin resistance, obesity, elevated LDL cholesterol and triglycerides, leading to metabolic syndrome (PMID: 26429086). Fructose-sweetened food and beverage products cause less of a rise in blood glucose levels than do those manufactured with either sucrose or glucose. BETA-L-FRUCTO-furanose b-L-FRUCTO-furanose Β-L-fructo-furanose b-L-Fructofuranose Β-L-fructofuranose C6H12O6 180.16 180.0634 (2S,3R,4R,5S)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol β-L-fructofuranose 41579-20-8 OC[C@@H]1O[C@@](O)(CO)[C@H](O)[C@H]1O InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m0/s1 RFSUNEUAIZKAJO-AZGQCCRYSA-N belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. C-glycosyl compounds Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Pentoses Polyols Primary alcohols Secondary alcohols Tetrahydrofurans Alcohol Aliphatic heteromonocyclic compound C-glycosyl compound Hemiacetal Hydrocarbon derivative Monosaccharide Organoheterocyclic compound Oxacycle Pentose monosaccharide Polyol Primary alcohol Secondary alcohol Tetrahydrofuran L-fructofuranose water_solubility 4000 g/L Wikipedia melting_point 103 °C Wikipedia logp -2.45 ALOGPS logs 0.79 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 10.28 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R,4R,5S)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles OC[C@@H]1O[C@@](O)(CO)[C@H](O)[C@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m0/s1 ChemAxon inchikey RFSUNEUAIZKAJO-AZGQCCRYSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 36.36 ChemAxon polarizability 16.3 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04173 439553 43703 Fructose Malik VS, Hu FB: Fructose and Cardiometabolic Health: What the Evidence From Sugar-Sweetened Beverages Tells Us. J Am Coll Cardiol. 2015 Oct 6;66(14):1615-1624. doi: 10.1016/j.jacc.2015.08.025. 26429086 1.0 2020-03-18 23:22:03 UTC 2020-09-11 20:08:58 UTC CDB006159 Citric acid Citric acid (citrate) is a weak tricarboxylic acid that is formed in the tricarboxylic acid cycle. In humans citric acid is produced endogenously or it may be introduced with diet, with citrus fruits being a key source. Citrate is produced by all aerobic organisms, from microbes to humans. Citrate is formed in the TCA cycle via the enzyme known as citrate synthase, which catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate then acts as the substrate for aconitase and is converted into aconitic acid. Some bacteria (notably E. coli) can produce and consume citrate internally as part of their TCA cycle, but are unable to use it as food because they lack the enzymes required to import it into the cell. Citrate has a number of biological roles in humans. In particular, it can be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis. Citrate can also acts as a signalling molecule. High concentrations of cytosolic citrate can inhibit phosphofructokinase, the catalyst of a rate-limiting step of glycolysis. Inhibition of glycolysis has been shown to suppress tumor growth in a number of animal models ( PMID: 28674429). Citrate is also a vital component of bone, helping to regulate the size of apatite crystals. Urinary citrate levels can be used to identify a number of disorders. Indeed urinary citrate excretion is a common tool in the differential diagnosis of kidney stones, renal tubular acidosis and it plays also a role in characterizing bone diseases such as osteoporosis (PMID 12957820). The secretory epithelial cells of the prostate gland of humans and other animals possess a unique citrate-related metabolic pathway regulated by testosterone and prolactin. This specialized hormone-regulated metabolic activity is responsible for the major prostate function of the production and secretion of extraordinarily high levels of citrate. The key regulatory enzymes directly associated with citrate production in the prostate cells are mitochondrial aspartate aminotransferase, pyruvate dehydrogenase, and mitochondrial aconitase. Testosterone and prolactin are involved in the regulation of the corresponding genes associated with these enzymes (PMID 12198595). In addition to its biological roles and endogenous production, citrate is obtained from many other sources and used in many applications. Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit. The concentrations of citric acid in citrus fruits range from 5 mM for oranges and grapefruits to 300 mM in lemons and limes. However, these values vary within species depending upon the cultivar and the circumstances in which the fruit was grown. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. Citric acid is used as an excipient in pharmaceutical preparations due to its antioxidant properties. It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. Citric acid is also used as an acidulant in creams, gels, and liquids. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Altered levels of citric acid have been found to be associated with maple syrup urine disease, primary hypomagnesemia, propionic acidemia, and tyrosinemia I, which are inborn errors of metabolism. C6H8O7 192.12 192.027 (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 77-92-9 OC(=O)CC(O)(CC(O)=O)C(O)=O InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) KRKNYBCHXYNGOX-UHFFFAOYSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Pinane monoterpenoid Tertiary alcohol water_solubility 592.0 mg/mL logp -1.64 AVDEEF,A (1997) melting_point 153 °C boiling_point 310 °C Wikipedia logp 2.56 ALOGPS logs -2.27 ALOGPS logp 1.89 ChemAxon pka_strongest_acidic 19.91 ChemAxon pka_strongest_basic -0.65 ChemAxon iupac (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol ChemAxon average_mass 192.12 ChemAxon mono_mass 192.027 ChemAxon smiles OC(=O)CC(O)(CC(O)=O)C(O)=O ChemAxon formula C6H8O7 ChemAxon inchi InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12) ChemAxon inchikey KRKNYBCHXYNGOX-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.55 ChemAxon polarizability 18.54 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6428289 Ren JG, Seth P, Ye H, Guo K, Hanai JI, Husain Z, Sukhatme VP: Citrate Suppresses Tumor Growth in Multiple Models through Inhibition of Glycolysis, the Tricarboxylic Acid Cycle and the IGF-1R Pathway. Sci Rep. 2017 Jul 3;7(1):4537. doi: 10.1038/s41598-017-04626-4. 28674429 Caudarella R, Vescini F, Buffa A, Stefoni S: Citrate and mineral metabolism: kidney stones and bone disease. Front Biosci. 2003 Sep 1;8:s1084-106. doi: 10.2741/1119. 12957820 Costello LC, Franklin RB: Testosterone and prolactin regulation of metabolic genes and citrate metabolism of prostate epithelial cells. Horm Metab Res. 2002 Aug;34(8):417-24. doi: 10.1055/s-2002-33598. 12198595 1.0 2020-03-18 23:22:05 UTC 2020-08-04 22:28:39 UTC CDB006160 Erythritol Erythritol, also known as erythrite or phycite, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Erythritol is an extremely weak basic (essentially neutral) compound (based on its pKa). Erythritol occurs widely in nature and has been found to occur naturally in several foods including wine, sake, beer, watermelon, pear, grape, and soy sauce. Erythritol is 60‚Äì70% as sweet as sucrose (table sugar), yet it is almost noncaloric and does not affect blood sugar or cause tooth decay (PMID:20186409, PMID1468100). Evidence indicates that erythritol also exists endogenously in the tissues and body fluids of humans and animals. Erythritol is absorbed from the proximal intestine by passive diffusion in a manner similar to that of many low molecular weight organic molecules which do not have associated active transport systems. The rate of absorption is related to their molecular size; erythritol, a 4-carbon molecule, passes through the intestinal membranes at a faster rate than larger molecules such as mannitol or glucose. In diabetics, erythritol has also been shown to be rapidly absorbed and excreted unchanged in the urine. Following absorption, ingested erythritol is rapidly distributed throughout the body and has been reported to occur in hepatocytes, pancreatic cells, and vascular smooth muscle cells. Erythritol also has been reported to cross the human placenta and to pass slowly from the plasma into the brain and cerebrospinal fluid (PMID: 9862657). Altered levels of erythritol have been found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism. (2R,3S)-Butane-1,2,3,4-tetrol Erythrit Erythrite Erythro-tetritol Erythrol L-Erythritol MESO-erythritol Mesoerythritol Phycite Phycitol 1,2,3,4-Butanetetrol Antierythrite Butanetetrol C*Eridex Erythroglucin I-erythritol L-(-)-Threitol L-Threitol Lichen sugar Meso-eythritol Paycite Tetrahydroxybutane 1,2,3,4-Tetrahydroxybutane C4H10O4 122.12 122.0579 (2R,3S)-butane-1,2,3,4-tetrol erythritol 149-32-6 OC[C@H](O)[C@H](O)CO InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+ UNXHWFMMPAWVPI-ZXZARUISSA-N belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Polyol Primary alcohol Secondary alcohol Sugar alcohol butane-1,2,3,4-tetrol water_solubility 610 mg/mL at 22 °C logp -2.29 HANSCH,C ET AL. (1995) melting_point 121.5 °C boiling_point 329 - 331 °C Wikipedia logp -2.03 ALOGPS logs 0.98 ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 13.04 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S)-butane-1,2,3,4-tetrol ChemAxon average_mass 122.12 ChemAxon mono_mass 122.0579 ChemAxon smiles OC[C@H](O)[C@H](O)CO ChemAxon formula C4H10O4 ChemAxon inchi InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+ ChemAxon inchikey UNXHWFMMPAWVPI-ZXZARUISSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 26.48 ChemAxon polarizability 11.62 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000371 DB04481 192963 C00503 222285 MRY 17113 ERYTHRITOL C00001161 Erythritol 140 Moon HJ, Jeya M, Kim IW, Lee JK: Biotechnological production of erythritol and its applications. Appl Microbiol Biotechnol. 2010 Apr;86(4):1017-25. doi: 10.1007/s00253-010-2496-4. Epub 2010 Feb 26. 20186409 Kawanabe J, Hirasawa M, Takeuchi T, Oda T, Ikeda T: Noncariogenicity of erythritol as a substrate. Caries Res. 1992;26(5):358-62. doi: 10.1159/000261468. 1468100 Munro IC, Berndt WO, Borzelleca JF, Flamm G, Lynch BS, Kennepohl E, Bar EA, Modderman J: Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data. Food Chem Toxicol. 1998 Dec;36(12):1139-74. doi: 10.1016/s0278-6915(98)00091-x. 9862657 1.0 2020-03-18 23:22:07 UTC 2020-07-24 23:30:05 UTC CDB006161 Ammonia Ammonia, also known as NH3 or amoniaco, belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'. Ammonia is a colourless alkaline gas and is one of the most abundant nitrogen-containing compounds in the atmosphere. It is an irritant with a characteristic pungent odor that is widely used in industry. Inasmuch as ammonia is highly soluble in water and, upon inhalation, is deposited in the upper airways, occupational exposures to ammonia have commonly been associated with sinusitis, upper airway irritation, and eye irritation. Acute exposures to high levels of ammonia have also been associated with diseases of the lower airways and interstitial lung. Small amounts of ammonia are naturally formed in nearly all tissues and organs of the vertebrate organism. Ammonia is both a neurotoxin and a metabotoxin. In fact, it is the most common endogenous neurotoxin. A neurotoxin is a compound that causes damage to neural tissue and neural cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Ammonia is recognized to be central in the pathogenesis of a brain condition known as hepatic encephalopathy, which arises from various liver diseases and leads to a build-up ammonia in the blood (hyperammonemia). More than 40% of people with cirrhosis develop hepatic encephalopathy. Part of the neurotoxicity of ammonia arises from the fact that it easily crosses the blood-brain barrier and is absorbed and metabolized by the astrocytes, a population of cells in the brain that constitutes 30% of the cerebral cortex. Astrocytes use ammonia when synthesizing glutamine from glutamate. The increased levels of glutamine lead to an increase in osmotic pressure in the astrocytes, which become swollen. There is increased activity of the inhibitory gamma-aminobutyric acid (GABA) system, and the energy supply to other brain cells is decreased. This can be thought of as an example of brain edema. The source of the ammonia leading to hepatic encaphlopahy is not entirely clear. The gut produces ammonia, which is metabolized in the liver, and almost all organ systems are involved in ammonia metabolism. Colonic bacteria produce ammonia by splitting urea and other amino acids, however this does not fully explain hyperammonemia and hepatic encephalopathy. The alternative explanation is that hyperammonemia is the result of intestinal breakdown of amino acids, especially glutamine. The intestines have significant glutaminase activity, predominantly located in the enterocytes. On the other hand, intestinal tissues only have a little glutamine synthetase activity, making it a major glutamine-consuming organ. In addition to the intestine, the kidney is an important source of blood ammonia in patients with liver disease. Ammonia is also taken up by the muscle and brain in hepatic coma, and there is confirmation that ammonia is metabolized in muscle. Excessive formation of ammonia in the brains of Alzheimer's disease patients has also been demonstrated, and it has been shown that some Alzheimer's disease patients exhibit elevated blood ammonia concentrations. Ammonia is the most important natural modulator of lysosomal protein processing. Indeed, there is strong evidence for the involvement of aberrant lysosomal processing of beta-amyloid precursor protein (beta-APP) in the formation of amyloid deposits. Inflammatory processes and activation of microglia are widely believed to be implicated in the pathology of Alzheimer's disease. Ammonia is able to affect the characteristic functions of microglia, such as endocytosis, and cytokine production. Based on these facts, an ammonia-based hypothesis for Alzheimer's disease has been suggested (PMID: 17006913, 16167195, 15377862, 15369278). Chronically high levels of ammonia in the blood are associated with nearly twenty different inborn errors of metabolism including: 3-hydroxy-3-methylglutaryl-CoA lyase deficiency, 3-methyl-crotonylglycinuria, argininemia, argininosuccinic aciduria, beta-ketothiolase deficiency, biotinidase deficiency, carbamoyl phosphate synthetase deficiency, carnitine-acylcarnitine translocase deficiency, citrullinemia type I, hyperinsulinism-hyperammonemia syndrome, hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, isovaleric aciduria, lysinuric protein intolerance, malonic aciduria, methylmalonic aciduria, methylmalonic aciduria due to cobalamin-related disorders, propionic acidemia, pyruvate carboxylase deficiency, and short chain acyl CoA dehydrogenase deficiency (SCAD deficiency). Many of these inborn errors of metabolism are associated with urea cycle disorders or impairment to amino acid metabolism. High levels of ammonia in the blood (hyperammonemia) lead to the activation of NMDA receptors in the brain. This results in the depletion of brain ATP, which in turn leads to release of glutamate. Ammonia also leads to the impairment of mitochondrial function and calcium homeostasis, thereby decreasing ATP synthesis. Excess ammonia also increases the formation of nitric oxide (NO), which in turn reduces the activity of glutamine synthetase, and thereby decreases the elimination of ammonia in the brain (PMID: 12020609). As a neurotoxin, ammonia predominantly affects astrocytes. Disturbed mitochondrial function and oxidative stress, factors implicated in the induction of the mitochondrial permeability transition, appear to be involved in the mechanism of ammonia neurotoxicity. Ammonia can also affect the glutamatergic and GABAergic neuronal systems, the two prevailing neuronal systems of the cortical structures. All of these effects can lead to irreversible brain damage, coma, and/or death. Infants with urea cycle disorders and hyperammonia initially exhibit vomiting and increasing lethargy. If untreated, seizures, hypotonia (poor muscle tone, floppiness), respiratory distress (respiratory alkalosis), and coma can occur. Adults with urea cycle disorders and hyperammonia will exhibit episodes of disorientation, confusion, slurred speech, unusual and extreme combativeness or agitation, stroke-like symptoms, lethargy, and delirium. Ammonia also has toxic effects when an individual is exposed to ammonia solutions. Acute exposure to high levels of ammonia in air may be irritating to skin, eyes, throat, and lungs and cause coughing and burns. Lung damage and death may occur after exposure to very high concentrations of ammonia. Swallowing concentrated solutions of ammonia can cause burns in the mouth, throat, and stomach. Splashing ammonia into eyes can cause burns and even blindness. [NH3] Ammoniac Ammoniak Amoniaco NH3 R-717 Spirit OF hartshorn Ammonia anhydrous Ammonia inhalant Ammonia solution strong Ammonia water Liquid ammonia Am-fol Ammonia (CONC 20% or greater) Ammonia gas Ammonia solution Ammonia solution strong (NF) Ammonia water (JP15) Ammoniacum gummi Ammoniak kconzentrierter Ammoniakgas Ammonium ion Anhydrous ammonia Aromatic ammonia vaporole Azane NH(3) Nitro-sil Primaeres amin Sekundaeres amin Tertiaeres amin H3N 17.03 17.0265 ammonia ammonia 15194-15-7 N InChI=1S/H3N/h1H3 QGZKDVFQNNGYKY-UHFFFAOYSA-N belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'. Homogeneous other non-metal compounds Inorganic compounds Homogeneous non-metal compounds Homogeneous other non-metal compounds Homogeneous other non metal a small molecule azane mononuclear parent hydride water_solubility 482 mg/mL at 24 °C melting_point -77.7 °C boiling_point −33.34 °C Wikipedia logp -0.98 ChemAxon pka_strongest_basic 8.86 ChemAxon iupac ammonia ChemAxon average_mass 17.03 ChemAxon mono_mass 17.0265 ChemAxon smiles N ChemAxon formula H3N ChemAxon inchi InChI=1S/H3N/h1H3 ChemAxon inchikey QGZKDVFQNNGYKY-UHFFFAOYSA-N ChemAxon polar_surface_area 13.59 ChemAxon refractivity 15.51 ChemAxon polarizability 1.99 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00014 DBMET01482 FDB003908 217 222 16134 C00007267 Ammonia AMMONIA 3189 Albrecht J, Norenberg MD: Glutamine: a Trojan horse in ammonia neurotoxicity. Hepatology. 2006 Oct;44(4):788-94. doi: 10.1002/hep.21357. 17006913 Shawcross DL, Olde Damink SW, Butterworth RF, Jalan R: Ammonia and hepatic encephalopathy: the more things change, the more they remain the same. Metab Brain Dis. 2005 Sep;20(3):169-79. doi: 10.1007/s11011-005-7205-0. 16167195 Norenberg MD, Rama Rao KV, Jayakumar AR: Ammonia neurotoxicity and the mitochondrial permeability transition. J Bioenerg Biomembr. 2004 Aug;36(4):303-7. doi: 10.1023/B:JOBB.0000041758.20071.19. 15377862 Brautbar N, Wu MP, Richter ED: Chronic ammonia inhalation and interstitial pulmonary fibrosis: a case report and review of the literature. Arch Environ Health. 2003 Sep;58(9):592-6. doi: 10.3200/AEOH.58.9.592-596. 15369278 Monfort P, Kosenko E, Erceg S, Canales JJ, Felipo V: Molecular mechanism of acute ammonia toxicity: role of NMDA receptors. Neurochem Int. 2002 Aug-Sep;41(2-3):95-102. doi: 10.1016/s0197-0186(02)00029-3. 12020609 1.0 2020-03-18 23:22:09 UTC 2020-07-22 22:11:10 UTC CDB006162 Dimethylamine Dimethylamine, also known as DMA or (CH3)2NH, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dimethylamine is a very strong basic compound (based on its pKa). Dimethylamine (DMA) is also classified as a secondary amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is abundantly present in human urine. The main sources of urinary DMA have been reported to include trimethylamine N-oxide, a common food component found in cold-water fish, and asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide (NO) synthesis. ADMA is excreted in the urine in part unmetabolized and in part after hydrolysis to DMA by dimethylarginine dimethylaminohydrolase (DDAH). Statistically significant increases in urinary DMA have been found in individuals after the consumption of fish and seafoods. The highest values were obtained for individuals that consumed coley, squid, whitting, cod, haddock, sardine, skate and swordfish (PMID: 18282650). DMA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Industrially, DMA is used as dehairing agent in tanning, in dyes, in rubber polymerization accelerators, in soaps and cleaning compounds and as an agricultural fungicide. In the body, DMA also undergoes nitrosation under weak acid conditions to give dimethlynitrosamine. Recent studies have shown that DMA is a metabolite produced by several species of bacteria including Arthrobacter and Micrococcus (PMID: 11422368). Dimethylamine is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). DMA HNMe2 Me2nh N,N-Dimethylamine (CH3)2nh Dimethylamine anhydrous Dimethylamine anhydrous (dot) Dimethylamine aqueous solution Dimethylamine hydrobromide Dimethylamine solution N-Methyl-methanamine N-Methylmethanamine N-Methylmethanamine (acd/name 4.0) Dimethylamine nitrate Dimethylamine perchlorate Dimethylamine sulfate Dimethylamine hydrochloride Dimethylamine phosphate (3:1) Dimethylamine, conjugate acid Dimethylammonium chloride Dimethylamine sulfate (1:1) Dimethylammonium formate Dimethylamine monosulfate C2H7N 45.08 45.0578 dimethylamine dimethylamine 124-40-3 CNC InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 ROSDSFDQCJNGOL-UHFFFAOYSA-N belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dialkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Secondary aliphatic amine methylamines secondary aliphatic amine water_solubility 1630 mg/mL at 40 °C logp -0.38 HANSCH,C ET AL. (1995) melting_point -92.2 °C boiling_point 7 - 9 °C Wikipedia logp -0.53 ALOGPS logs 1.06 ALOGPS logp -0.19 ChemAxon pka_strongest_basic 10.52 ChemAxon iupac dimethylamine ChemAxon average_mass 45.08 ChemAxon mono_mass 45.0578 ChemAxon smiles CNC ChemAxon formula C2H7N ChemAxon inchi InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 ChemAxon inchikey ROSDSFDQCJNGOL-UHFFFAOYSA-N ChemAxon polar_surface_area 12.03 ChemAxon refractivity 14.69 ChemAxon polarizability 5.75 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00543 FDB012589 654 674 17170 DIMETHYLAMINE Dimethylamine 3758 Mitchell SC, Zhang AQ, Smith RL: Dimethylamine and diet. Food Chem Toxicol. 2008 May;46(5):1734-8. doi: 10.1016/j.fct.2008.01.010. Epub 2008 Jan 15. 18282650 Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. 22626821 Meskys R, Harris RJ, Casaite V, Basran J, Scrutton NS: Organization of the genes involved in dimethylglycine and sarcosine degradation in Arthrobacter spp.: implications for glycine betaine catabolism. Eur J Biochem. 2001 Jun;268(12):3390-8. doi: 10.1046/j.1432-1327.2001.02239.x. 11422368 1.0 2020-03-18 23:22:11 UTC 2020-07-22 22:11:10 UTC CDB006163 Galactitol Galactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. It is this galactose that is broken down to galactitol via a reaction catalyzed by aldose reductase. Galactitol has a slightly sweet taste. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individual's ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure. Outside of the human body, Galactitol has been detected, but not quantified in, several different foods, such as common buckwheats, winter squash, calabash, black walnuts, and peanuts. This could make galactitol a potential biomarker for the consumption of these foods. (2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexol D-Dulcitol D-Galactitol Dulcitol Dulcose Euonymit L-Galactitol Melampyrin Melampyrit Ambap5938 Dulcite Hexitol Melampyrite Melampyrum Meso-galactitol C6H14O6 182.17 182.079 (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol galactitol 608-66-2 OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- FBPFZTCFMRRESA-GUCUJZIJSA-N belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Monosaccharides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Monosaccharide Polyol Primary alcohol Secondary alcohol Sugar alcohol hexitol water_solubility 31,0 mg/mL at 15 °C YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -3.10 HANSCH,C ET AL. (1995) melting_point 189.5 °C boiling_point 275-280 °C Wikipedia logp -2.68 ALOGPS logs 0.10 ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 12.59 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol ChemAxon average_mass 182.17 ChemAxon mono_mass 182.079 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO ChemAxon formula C6H14O6 ChemAxon inchi InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- ChemAxon inchikey FBPFZTCFMRRESA-GUCUJZIJSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 38.4 ChemAxon polarizability 17.25 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01697 FDB006453 11357 11850 16813 C00001160 Galactitol 38183 5148 1.0 2020-03-18 23:22:13 UTC 2020-09-11 20:08:57 UTC CDB006164 Glyceric acid Glyceric acid is a colourless syrupy acid, obtained via the oxidation of glycerol. Glyceric acid is a weak 3-carbon sugar acid. Several phosphate derivatives of glyceric acid, including 2-phosphoglyceric acid, 3-phosphoglyceric acid, 2,3-bisphosphoglyceric acid, and 1,3-bisphosphoglyceric acid, are important biochemical intermediates in glycolysis. In particular, 3-phosphoglyceric acid is an important molecule for the biosynthesis of the amino acid serine, which in turn can be used in the synthesis of glycine and cysteine. Glyceric acid is not normally found in human biofluids, however high levels are secreted in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism. It is also elevated in the serum of individuals suffering from D-glycerate anemia. A deficiency of human glycerate kinase has been shown to lead to D-glycerate acidemia/D-glyceric aciduria ( PMID: 20949620). Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Abnormally high levels of organic acids (glyceric acid is an organic acid) in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Elevated values may also be due to microbial sources such as yeast (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). Glyceric acid can be isolated from various crop plants (e.g. brassicas and pulses) and has also been found in peanuts, artichokes, tomatoes, apples, bananas, broad beans and grapes (PMID: 19621222). alpha,beta-Hydroxypropionic acid D-GroA R-Glyceric acid Glycerate (R)-Glycerate a,b-Hydroxypropionate a,b-Hydroxypropionic acid alpha,beta-Hydroxypropionate R-Glycerate (R)-Glyceric acid D-Glycerate D-Glyceric acid (2R)-2,3-Dihydroxypropanoic acid (R)-2,3-Dihydroxypropanoic acid D-2,3-Dihydroxypropanoic acid C3H6O4 106.08 106.0266 (2R)-2,3-dihydroxypropanoic acid glycerate 6000-40-4 OC[C@@H](O)C(O)=O InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1 RBNPOMFGQQGHHO-UWTATZPHSA-N belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds 1,2-diols Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Primary alcohols Secondary alcohols 1,2-diol Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Glyceric_acid Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Primary alcohol Secondary alcohol Sugar acid glyceric acid water_solubility 1000.0 mg/mL logp -1.723 Wikipedia melting_point <25 °C Wikipedia boiling_point 412 °C Wikipedia logp -1.72 ALOGPS logs 0.78 ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 3.42 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-2,3-dihydroxypropanoic acid ChemAxon average_mass 106.08 ChemAxon mono_mass 106.0266 ChemAxon smiles OC[C@@H](O)C(O)=O ChemAxon formula C3H6O4 ChemAxon inchi InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1 ChemAxon inchikey RBNPOMFGQQGHHO-UWTATZPHSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 20.38 ChemAxon polarizability 8.96 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012242 C00258 439194 388334 32398 C00001185 GLYCERATE Glyceric acid 34424 280 Habe H, Fukuoka T, Kitamoto D, Sakaki K: Biotechnological production of D-glyceric acid and its application. Appl Microbiol Biotechnol. 2009 Sep;84(3):445-52. doi: 10.1007/s00253-009-2124-3. Epub 2009 Jul 21. 19621222 Sass JO, Fischer K, Wang R, Christensen E, Scholl-Burgi S, Chang R, Kapelari K, Walter M: D-glyceric aciduria is caused by genetic deficiency of D-glycerate kinase (GLYCTK). Hum Mutat. 2010 Dec;31(12):1280-5. doi: 10.1002/humu.21375. Epub 2010 Nov 9. 20949620 1.0 2020-03-18 23:22:15 UTC 2020-07-22 22:11:10 UTC CDB006165 Maltose D-Maltose, also known as malt sugar, maltobiose or alpha-malt sugar, is a disaccharide consisting of two glucose subunits joined via an alpha-1-4 bond. Carbohydrates are generally divided into different categories based on the number of sugar subunits; monosaccharides (1 sugar subunit), disaccharides (2 sugar subunits), oligosaccharides (3 or more sugar subunits) and polysaccharides (hundreds to thousands of subunits, including starch). Maltose is a common byproduct of starch. When beta-amylase breaks down starch, it removes two glucose units at a time, thereby producing maltose. Maltose can be broken down to glucose by the maltase enzyme, which catalyses the hydrolysis of the glycosidic bond. D-Maltose exists in all living species, ranging from bacteria to humans. Maltose was 'discovered' by Augustin-Pierre Dubrunfaut, although this discovery was not widely accepted until it was confirmed in 1872 by Irish chemist and brewer Cornelius O'Sullivan. Its name comes from malt, combined with the suffix '-ose' which is used in naming all sugars. Like glucose, maltose is a reducing sugar, because the ring of one of the two glucose units can open to present a free aldehyde group. Maltose, when placed in aqueous solution, exhibits mutarotation. This is because the α and β isomers that are formed by the different conformations of the anomeric carbon have different specific rotations. In aqueous solutions, these two forms are in equilibrium. Maltose has a sweet taste, but is only about 30-60% as sweet as sucrose. Within humans, D-maltose participates in a number of enzymatic reactions. In particular, D-maltose can be converted into Alpha-D-glucose; which is mediated by intestinal maltase-glucoamylase. In addition, D-maltose can be converted into Alpha-D-glucose through its interaction with the enzyme glycogen debranching enzyme. In humans, D-maltose is involved in the metabolic disorder called the sucrase-isomaltase deficiency. Outside of the human body, D-maltose is found in high concentrations a variety of foods such as fruit gums, marshmallows, and oriental wheats. It is found in lower concentrations in bread, bagels, breakfast cereals, crackers, cornmeal, wheat, barley, candies, honey, molasses, beer and wines. Maltose is found mainly in grains and cereals. Wheat, corn, barley and rye all contain varying amounts of maltose. For some foods, cooking can increase the maltose content. For example, raw sweet potatoes don't have any maltose, but cooked sweet potatoes contain maltose at varying amounts depending on the type of sweet potato. Maltose is a component of malt, a substance which is obtained in the process of allowing grain to soften in water and germinate. Maltose is also found in partially hydrolysed starch products like maltodextrin, corn syrup and acid-thinned starch. 4-O-alpha-D-Glucopyranosyl-alpha-D-mannopyranose 4-O-a-D-Glucopyranosyl-a-D-mannopyranose 4-O-Α-D-glucopyranosyl-α-D-mannopyranose 1-alpha-D-Glucopyranosyl-4-alpha-D-glucopyranose 1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose 4-(alpha-D-Glucopyranosido)-alpha-glucopyranose 4-(alpha-D-Glucosido)-D-glucose 4-(alpha-delta-Glucopyranosido)-alpha-glucopyranose 4-(alpha-delta-Glucosido)-delta-glucose 4-O-a-D-Glucopyranosyl-D-glucose 4-O-alpha-D-Glucopyranosyl-D-glucopyranose 4-O-alpha-D-Glucopyranosyl-D-glucose 4-O-alpha-delta-Glucopyranosyl-delta-glucopyranose 4-O-alpha-delta-Glucopyranosyl-delta-glucose Advantose 100 alpha-D-GLCP-(1->4)-D-GLCP alpha-D-Glucopyranosyl-(1->4)-D-glucopyranose alpha-D-Glucopyranosyl-(1->4)-D-glucose alpha-delta-GLCP-(1->4)-delta-GLCP alpha-delta-Glucopyranosyl-(1->4)-delta-glucopyranose alpha-delta-Glucopyranosyl-(1->4)-delta-glucose alpha-Malt sugar Cextromaltose D-(+)-Maltose delta-(+)-Maltose delta-Maltose Finetose Finetose F Madoros Malt sugar Maltobiose Maltodiose Maltos Maltose Maltose HH Maltose HHH Maltose solution Malzzucker Martos-10 Sunmalt Sunmalt S C12H22O11 342.3 342.1162 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol 69-79-4 OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1 GUBGYTABKSRVRQ-DKBJLJRDSA-N belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. O-glycosyl compounds Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Disaccharides Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound Disaccharide Hemiacetal Hydrocarbon derivative O-glycosyl compound Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol alpha-D-glucosyl-(1->4)-D-mannopyranose water_solubility 780.0 mg/mL melting_point 102 - 103 °C boiling_point 667.9 °C Wikipedia logp -3.01 ALOGPS logs 0.23 ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 11.25 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol ChemAxon average_mass 342.3 ChemAxon mono_mass 342.1162 ChemAxon smiles OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C12H22O11 ChemAxon inchi InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1 ChemAxon inchikey GUBGYTABKSRVRQ-DKBJLJRDSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.34 ChemAxon polarizability 31.43 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00208 FDB001193 9166684 10991489 47937 C00001140 Maltose 34261 413 1.0 2020-03-18 23:22:17 UTC 2020-07-22 22:11:10 UTC CDB006166 Oleic acid Oleic acid, also known as oleate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Oleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the plant oil that is predominantly composed of oleic acid. Oleic acid is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. Fatty acids such as oleic acid occur primarily esters (not as free acids), mostly in the form of triglycerides, which are the greasy materials in many natural oils. Oleic acid is an odorless, colourless oil, although commercial samples may be yellowish. Oleic acid is particularly abundant in plant oils e.g. olive oil (about 80%), almond oil (about 80%) 59–75% of pecan oil, 61% of canola oil, 36–67% of peanut oil, 60% of macadamia oil, 20–80% of sunflower oil, 15–20% of grape seed oil, 40% of sesame oil and 14% of poppyseed oil. Oleic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Oleic acid is the most abundant fatty acid in human adipose tissue and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is used in the manufacturing of surfactants, soaps, plasticizers and as an emulsifying agent in foods, lotions, cosmetics and pharmaceuticals. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil . Altered levels of oleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism. (9Z)-Octadecenoic acid (Z)-Octadec-9-enoic acid 18:1 N-9 18:1DElta9cis C18:1 N-9 cis-9-Octadecenoic acid cis-Delta(9)-Octadecenoic acid cis-Oleic acid FA 18:1 Octadec-9-enoic acid Oelsaeure Oleate (9Z)-Octadecenoate (Z)-Octadec-9-enoate cis-9-Octadecenoate cis-delta(9)-Octadecenoate cis-Δ(9)-octadecenoate cis-Δ(9)-octadecenoic acid cis-Oleate Octadec-9-enoate (9Z)-9-Octadecenoate (9Z)-9-Octadecenoic acid (Z)-9-Octadecanoate (Z)-9-Octadecanoic acid 9,10-Octadecenoate 9,10-Octadecenoic acid 9-(Z)-Octadecenoate 9-(Z)-Octadecenoic acid 9-Octadecenoate 9-Octadecenoic acid Century CD fatty acid cis-Octadec-9-enoate cis-Octadec-9-enoic acid Distoline Emersol 210 Emersol 211 Emersol 213 Emersol 220 white oleate Emersol 220 white oleic acid Emersol 221 low titer white oleate Emersol 221 low titer white oleic acid Emersol 233LL Emersol 6321 Emersol 6333 NF Emersol 7021 Glycon ro Glycon wo Groco 2 Groco 4 Groco 5l Groco 6 Industrene 104 Industrene 105 Industrene 205 Industrene 206 L'acide oleique Metaupon Oelsauere Oleic acid extra pure Oleinate Oleinic acid Pamolyn Pamolyn 100 Pamolyn 100 FG Pamolyn 100 FGK Pamolyn 125 Priolene 6900 Red oil Tego-oleic 130 Vopcolene 27 Wecoline oo Z-9-Octadecenoate Z-9-Octadecenoic acid Acid, 9-octadecenoic Acid, oleic 9 Octadecenoic acid Acid, cis-9-octadecenoic cis 9 Octadecenoic acid FA(18:1(9Z)) FA(18:1n9) C18H34O2 282.46 282.2559 (9Z)-octadec-9-enoic acid oleic acid 112-80-1 CCCCCCCC\C=C/CCCCCCCC(O)=O InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- ZQPPMHVWECSIRJ-KTKRTIGZSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Monounsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids octadec-9-enoic acid melting_point 13.4 °C boiling_point 360 °C Wikipedia logp 7.68 ALOGPS logs -6.37 ALOGPS logp 6.78 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9Z)-octadec-9-enoic acid ChemAxon average_mass 282.46 ChemAxon mono_mass 282.2559 ChemAxon smiles CCCCCCCC\C=C/CCCCCCCC(O)=O ChemAxon formula C18H34O2 ChemAxon inchi InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- ChemAxon inchikey ZQPPMHVWECSIRJ-KTKRTIGZSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 87.4 ChemAxon polarizability 37.09 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00712 FDB012858 393217 16196 445639 C00001232 OLEATE-CPD Oleic_acid 190 1.0 2020-03-18 23:22:19 UTC 2020-07-24 23:30:05 UTC CDB006167 Pyroglutamic acid Pyroglutamic acid (5-oxoproline) is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on gamma-glutamyl dipeptides. Elevated blood levels of pyroglutamate may be associated with problems of glutamine or glutathione metabolism. Pyroglutamate is found in substantial amounts in brain tissue and other tissues in bound form, especially skin. It is also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain. Pyroglutamate in the urine is a biomarker for the consumption of cheese. When present in sufficiently high levels, pyroglutamic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of pyroglutamic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria, 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia. Pyroglutamic acid is an organic acid. It is an extremely weak basic (essentially neutral) compound (based on its pKa). Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. It has been shown that pyroglutamic acid releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, pyroglutamic acid significantly shortens the plasma half-life of ethanol during acute intoxication. (-)-2-Pyrrolidone-5-carboxylic acid (S)-(-)-2-Pyrrolidone-5-carboxylic acid (S)-Pyroglutamic acid 5-Pyrrolidone-2-carboxylic acid L-5-Pyrrolidone-2-carboxylic acid L-Pyroglutamic acid Pidolic acid Pyroglutamate 5-oxo-L-Proline (-)-2-Pyrrolidone-5-carboxylate (S)-(-)-2-Pyrrolidone-5-carboxylate (S)-Pyroglutamate 5-Pyrrolidone-2-carboxylate L-5-Pyrrolidone-2-carboxylate L-Pyroglutamate Pidolate (-)-Pyroglutamate (-)-Pyroglutamic acid (5S)-2-Oxopyrrolidine-5-carboxylate (5S)-2-Oxopyrrolidine-5-carboxylic acid (S)-(-)-g-Butyrolactam-g-carboxylate (S)-(-)-g-Butyrolactam-g-carboxylic acid (S)-(-)-gamma-Butyrolactam-gamma-carboxylate (S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid (S)-2-Pyrrolidone-5-carboxylate (S)-2-Pyrrolidone-5-carboxylic acid (S)-5-oxo-2-Pyrrolidinecarboxylate (S)-5-oxo-2-Pyrrolidinecarboxylic acid 2-L-Pyrrolidone-5-carboxylate 2-L-Pyrrolidone-5-carboxylic acid 2-Oxopyrrolidine-5(S)-carboxylate 2-Oxopyrrolidine-5(S)-carboxylic acid 2-Pyrrolidinone-5-carboxylate 2-Pyrrolidinone-5-carboxylic acid 5-Carboxy-2-pyrrolidinone 5-L-Oxoproline 5-Oxoproline 5-Pyrrolidinone-2-carboxylate 5-Pyrrolidinone-2-carboxylic acid Ajidew a 100 Glutimate Glutimic acid Glutiminate Glutiminic acid L-2-Pyrrolidone-5-carboxylate L-2-Pyrrolidone-5-carboxylic acid L-5-Carboxy-2-pyrrolidinone L-5-oxo-2-Pyrrolidinecarboxylate L-5-oxo-2-Pyrrolidinecarboxylic acid L-5-Oxoproline L-Glutamic acid g-lactam L-Glutimate L-Glutimic acid L-Glutiminate L-Glutiminic acid L-Pyrrolidinonecarboxylate L-Pyrrolidinonecarboxylic acid L-Pyrrolidonecarboxylate L-Pyrrolidonecarboxylic acid Oxoproline Oxopyrrolidinecarboxylate Oxopyrrolidinecarboxylic acid Pidolidone Pyrrolidinonecarboxylate Pyrrolidinonecarboxylic acid Pyrrolidone-5-carboxylate Pyrrolidone-5-carboxylic acid Pyrrolidonecarboxylic acid 5-Ketoproline Pidolate, magnesium 5-Oxopyrrolidine-2-carboxylic acid Magnesium pidolate 2-Pyrrolidone-5-carboxylic acid 5-Oxoprolinate PCA C5H7NO3 129.11 129.0426 (2S)-5-oxopyrrolidine-2-carboxylic acid pyroglutamic acid 16891-48-8 OC(=O)[C@@H]1CCC(=O)N1 InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 ODHCTXKNWHHXJC-VKHMYHEASA-N belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Alpha amino acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic heteromonocyclic compounds Azacyclic compounds Carbonyl compounds Carboxylic acids Cyclic carboximidic acids Hydrocarbon derivatives Lactims Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Pyrroline carboxylic acids Aliphatic heteromonocyclic compound Alpha-amino acid or derivatives Azacycle Carbonyl group Carboxylic acid Cyclic carboximidic acid Hydrocarbon derivative Lactim Monocarboxylic acid or derivatives Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Pyrroline Pyrroline carboxylic acid Pyrroline carboxylic acid or derivatives 5-oxoproline L-proline derivative Other amino acids non-proteinogenic L-alpha-amino acid water_solubility 476.0 mg/mL at 13 °C logp -0.89 Wikipedia melting_point 184 °C Wikipedia logp -1.01 ALOGPS logs 0.07 ALOGPS logp -0.89 ChemAxon pka_strongest_acidic 3.61 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2S)-5-oxopyrrolidine-2-carboxylic acid ChemAxon average_mass 129.11 ChemAxon mono_mass 129.0426 ChemAxon smiles OC(=O)[C@@H]1CCC(=O)N1 ChemAxon formula C5H7NO3 ChemAxon inchi InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 ChemAxon inchikey ODHCTXKNWHHXJC-VKHMYHEASA-N ChemAxon polar_surface_area 66.4 ChemAxon refractivity 28.09 ChemAxon polarizability 11.56 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01879 DB03088 FDB014506 18183 7405 5-OXOPROLINE C00007403 Pyroglutamic_acid 1.0 2020-03-18 23:22:21 UTC 2020-09-11 20:08:57 UTC CDB006168 Tyramine Tyramine is a monoamine compound derived from the amino acid tyrosine. It is a very strong basic compound (based on its pKa). Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish (herring), chocolate, alcoholic beverages, cheese, yogurt, soy sauce, sauerkraut, and processed meat. Tyramine in the blood or urine is often considered as a biomarker for the consumption of cheese. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more and induce migraine headaches (PMID: 27424325). The tyramine connection to hypertensive episodes was discovered by a British pharmacist whose wife was taking an monoamine oxidase inhibitors (MAOI). He noticed that every time they had a meal with cheese, she would get a severe headache (PMID: 19742203). Tyramine acts as a neurotransmitter via a G protein-coupled receptor called TA1, which has a high affinity for tyramine. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. As an indirect sympathomimetic compound, tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase, so it prolongs the actions of adrenergic transmitters. Tyramine also provokes transmitter release from adrenergic terminals. 2-(p-Hydroxyphenyl)ethylamine 4-Hydroxy-beta-phenylethylamine 4-Hydroxyphenethylamine 4-Hydroxyphenylethylamine beta-(4-Hydroxyphenyl)ethylamine p-(2-Aminoethyl)phenol p-Hydroxyphenethylamine p-Hydroxyphenylethylamine p-Tyramine Tyramin 4-Hydroxy-b-phenylethylamine 4-Hydroxy-β-phenylethylamine b-(4-Hydroxyphenyl)ethylamine Β-(4-hydroxyphenyl)ethylamine 2-(4'-Hydroxyphenyl)ethylamine 2-(4-Hydroxyphenyl)ethylamine 4-(2-Aminoethyl)-phenol 4-(2-Aminoethyl)-phenol(thyramin) 4-(2-Aminoethyl)phenol 4-Hydroxy-benzeneethanamine a-(4-Hydroxyphenyl)-b-aminoethane alpha-(4-Hydroxyphenyl)-beta-aminoethane p-(2-Aminoethyl)-phenol p-beta-Aminoethylphenol p-Hydroxy-b-phenethylamine p-Hydroxy-b-phenylethylamine p-Hydroxy-beta-phenethylamine p-Hydroxy-beta-phenylethylamine Systogene Tenosin-wirkstoff Tocosine Tyramine base Tyrosamine Uteramine Para-tyramine 4 Hydroxyphenethylamine 2-(4-Hydroxyphenyl)ethanamine 2-(4’-hydroxyphenyl)ethylamine p-Hydroxy-β-phenylethylamine p-Β-aminoethylphenol Α-(4-hydroxyphenyl)-β-aminoethane C8H11NO 137.18 137.0841 4-(2-aminoethyl)phenol tyramine 51-67-2 NCCC1=CC=C(O)C=C1 InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 DZGWFCGJZKJUFP-UHFFFAOYSA-N belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Phenethylamines Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 2-arylethylamines Aralkylamines Hydrocarbon derivatives Monoalkylamines Organooxygen compounds Organopnictogen compounds 1-hydroxy-2-unsubstituted benzenoid 2-arylethylamine Amine Aralkylamine Aromatic homomonocyclic compound Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenethylamine Phenol Primary aliphatic amine Primary amine Biogenic amines Tyramine derivatives monoamine molecular messenger primary amino compound tyramines water_solubility 10.4 mg/mL at 15 °C melting_point 164 - 165 °C boiling_point 206 °C at 25 mmHg Wikipedia logp -0.14 ALOGPS logs -1.38 ALOGPS logp 0.68 ChemAxon pka_strongest_acidic 10.41 ChemAxon pka_strongest_basic 9.66 ChemAxon iupac 4-(2-aminoethyl)phenol ChemAxon average_mass 137.18 ChemAxon mono_mass 137.0841 ChemAxon smiles NCCC1=CC=C(O)C=C1 ChemAxon formula C8H11NO ChemAxon inchi InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2 ChemAxon inchikey DZGWFCGJZKJUFP-UHFFFAOYSA-N ChemAxon polar_surface_area 46.25 ChemAxon refractivity 41.27 ChemAxon polarizability 15.33 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00483 DB08841 FDB000433 5408 5610 15760 C00001435 Tyramine TYRAMINE 35110 60 Khan MZ, Nawaz W: The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed Pharmacother. 2016 Oct;83:439-449. doi: 10.1016/j.biopha.2016.07.002. Epub 2016 Jul 15. 27424325 Sathyanarayana Rao TS, Yeragani VK: Hypertensive crisis and cheese. Indian J Psychiatry. 2009 Jan;51(1):65-6. doi: 10.4103/0019-5545.44910. 19742203 1.0 2020-03-18 23:22:22 UTC 2020-08-04 22:28:39 UTC CDB006169 Ribitol Ribitol, also known as adonitol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Ribitol is formed by the reduction of the 5-carbon sugar ribose. Ribitol occurs naturally in some plants such as the pheasant‚Äôs eye (Adonis vernalis) and in the cell walls of some Gram-positive bacteria (in the form of ribitol phosphate). In humans, ribitol is a metabolic end product formed by the reduction of ribose in human fibroblasts and erythrocytes (pentitol, sugar alcohol, polyol). Industrially, tibitol can be used as a cryopreservative and has a strong protective effect on lactic acid bacteria during freeze-drying. Ribitol has been reported as one of the sugar alcohols present in cannabis plants (PMID: 4688907). (2R,3S,4S)-Pentane-1,2,3,4,5-pentol Adonitol D-Adonitol D-Ribitol L-Ribitol 1,2,3,4,5-Pentanepentol Adonit Adonite Pentitol C10H18 138.25 138.1409 (2R,3s,4S)-pentane-1,2,3,4,5-pentol ribitol 87-99-0 CC=C(C)CCC=C(C)C InChI=1S/C10H18/c1-5-10(4)8-6-7-9(2)3/h5,7H,6,8H2,1-4H3 MZPDTOMKQCMETI-UHFFFAOYSA-N belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Monosaccharides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Monosaccharide Polyol Primary alcohol Secondary alcohol Sugar alcohol ribitol melting_point 102 °C Wikipedia logp -2.53 ALOGPS logs 0.64 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 12.76 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3s,4S)-pentane-1,2,3,4,5-pentol ChemAxon average_mass 138.25 ChemAxon mono_mass 138.1409 ChemAxon smiles CC=C(C)CCC=C(C)C ChemAxon formula C10H18 ChemAxon inchi InChI=1S/C10H18/c1-5-10(4)8-6-7-9(2)3/h5,7H,6,8H2,1-4H3 ChemAxon inchikey MZPDTOMKQCMETI-UHFFFAOYSA-N ChemAxon polar_surface_area 101.15 ChemAxon refractivity 32.44 ChemAxon polarizability 14.38 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00474 FDB022083 10254628 15963 C00001171 Ribitol RIBITOL 35086 316 Groce JW, Jones LA: Carbohydrate and cyclitol content of cannabis. J Agric Food Chem. 1973 Mar-Apr;21(2):211-4. doi: 10.1021/jf60186a003. 4688907 1.0 2020-03-18 23:22:24 UTC 2020-08-04 22:28:39 UTC CDB006170 Gluconic acid Gluconic acid, also known as dextronic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Gluconic acid is an extremely weak acid (based on its pKa). Gluconic acid exists in all living species, ranging from bacteria to humans. Gluconic acid is produced in particularly high abundance by certain fungi, such as Aspergillus niger (PMID: 24039465). Gluconic acid occurs naturally in fruit, honey, kombucha tea, and cow‚Äôs milk. Gluconic acid and its lactone have also been found in some table wines. The source of gluconic acid is most likely mold metabolism. Industrially, gluconate is used as a concrete admixture (retarder) to slow down the cement hydration reactions and to delay the cement setting time. It is also used in cleaning products where it helps cleaning up mineral deposits. In this regard, gluconic acid has been found to chelate the anions of calcium, iron, aluminium, copper, various rare earths and other heavy metals. The salts of gluconic acid are known as "gluconates". Gluconic acid is also used to maintain the cation-anion balance on electrolyte solutions and is present in certain electrolye solutions, such as "plasmalyte A", which is used for intravenous fluid resuscitation. Gluconate is also used in a variety of pharmaceutical applications. For instance, calcium gluconate is used to treat burns arising from hydrofluoric acid while quinine gluconate is a salt of gluconic acid and quinine, which is used for intramuscular injection in the treatment of malaria. In humans, altered levels of gluconic acid have been found in the metabolic disorder called the transaldolase deficiency. (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid D-Gluco-hexonic acid D-Gluconsaeure D-Glukonsaeure Dextronic acid Glycogenic acid Hexonic acid Maltonic acid D-Gluconate (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoate D-Gluco-hexonate Dextronate Glycogenate Hexonate Maltonate D-Gluconic acid Gluconate 2,3,4,5,6-Pentahydroxy-hexanoate 2,3,4,5,6-Pentahydroxy-hexanoic acid 2,3,4,5,6-Pentahydroxyhexanoate 2,3,4,5,6-Pentahydroxyhexanoic acid GCO Glosanto Glyconate Glyconic acid Pentahydroxycaproate Pentahydroxycaproic acid Boron gluconate Gluconic acid, (113)indium-labeled Gluconic acid, calcium salt Gluconic acid, cesium(+3) salt Gluconic acid, lanthanum(+3) salt Gluconic acid, sodium salt Gluconic acid, strontium (2:1) salt Magnerot Manganese gluconate Sodium gluconate Zinc gluconate Gluconic acid, (159)dysprosium-labeled salt Gluconic acid, aluminum (3:1) salt Gluconic acid, ammonium salt Gluconic acid, magnesium (2:1) salt Gluconic acid, (14)C-labeled Gluconic acid, 1-(14)C-labeled Gluconic acid, 6-(14)C-labeled Gluconic acid, cobalt (2:1) salt Gluconic acid, copper salt Gluconic acid, manganese (2:1) salt Gluconic acid, potassium salt Gluconic acid, tin(+2) salt Gluconic acid, zinc salt Lithium gluconate Magnesium gluconate Gluconic acid, (99)technecium (5+) salt Gluconic acid, fe(+2) salt, dihydrate Gluconic acid, monolithium salt Gluconic acid, monopotassium salt Gluconic acid, monosodium salt C6H12O7 196.16 196.0583 (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid gluconate 526-95-4 OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 RGHNJXZEOKUKBD-SQOUGZDYSA-N belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Gluconic_acid Hydrocarbon derivative Hydroxy acid Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol Uronic acids gluconic acid water_solubility 316 mg/mL at 25 °C MERCK INDEX (1996) melting_point 113 - 118 °C boiling_point 417 °C Wikipedia logp -2.57 ALOGPS logs -0.09 ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid ChemAxon average_mass 196.16 ChemAxon mono_mass 196.0583 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O ChemAxon formula C6H12O7 ChemAxon inchi InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 ChemAxon inchikey RGHNJXZEOKUKBD-SQOUGZDYSA-N ChemAxon polar_surface_area 138.45 ChemAxon refractivity 38.27 ChemAxon polarizability 17.15 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001980 DB13180 C00257 10240 10690 33198 GLUCONATE C00007303 Gluconic_acid 345 Shindia AA, El-Sherbeny GA, El-Esawy AE, Sheriff YM: Production of gluconic Acid by some local fungi. Mycobiology. 2006 Mar;34(1):22-9. doi: 10.4489/MYCO.2006.34.1.022. Epub 2006 Mar 31. 24039465 1.0 2020-03-18 23:22:26 UTC 2020-08-04 22:28:39 UTC CDB006171 Glucaric acid Glucaric acid, also known as D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is very soluble in water, and relatively neutral. Glucaric acid exists in all living organisms, ranging from bacteria to humans. In mammals, D-glucaric acid is an end product of the D-glucuronic acid pathway. The glucuronic acid pathway catalyzes the conversion of glucose to glucuronic acid, ascorbic acid, and pentoses. Like the pentose phosphate pathway, this pathway provides biosynthetic precursors and inter-converts some less common sugars to ones that can be metabolized. D-glucaric acid is particularly abundant in fruits and vegetables, with the highest concentrations found in grapefruits, apples, oranges, and cruciferous vegetables. The D-glucaric acid content in fruits and vegetables ranges from about 0.1 g/kg in grapes and lettuce to about 3.5 g/kg in apples and broccoli. Glucaric acid is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 12747003; PMID: 18772850). Industrially, D-glucaric acid produced from oxidizing D-glucose has been successfully utilized to produce a hydroxylated nylon, resulting in a presumably biodegradable nylon fiber. Glucaric acid‚Äôs sodium salt is used in dishwasher detergents. The acid acts as a chelating agent that ties up the hard-water calcium and magnesium ions to make the detergents more efficient. Glucaric acid is also a powerful corrosion inhibitor and is used in many applications where water contacts metal surfaces. D-(+)-Saccharic acid D-Glucosaccharic acid D-Saccharic acid L-Gularic acid Saccharic acid D-Glucaric acid Glucarate D-(+)-Saccharate D-Glucosaccharate D-Saccharate L-Gularate Saccharate D-Glucarate (2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioate (2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acid D-Tetrahydroxyadipate D-Tetrahydroxyadipic acid DL-Glucaric acid GKR Glucosaccharic acid Tetrahydroxyadipic acid Acid, saccharic Anhydrous calcium glucarate Anhydrous calcium saccharate Calcium saccharate Glucarate, calcium Levo gularic acid Levo-gularic acid Tetrahydrate, calcium saccharate Calcium glucarate Calcium glucarate, anhydrous Calcium saccharate anhydrous Calcium saccharate, anhydrous D Glucaric acid Saccharate tetrahydrate, calcium Saccharate, calcium Calcium saccharate tetrahydrate D Saccharic acid Glucarate, anhydrous calcium L Gularic acid Saccharate, anhydrous calcium C6H10O8 210.14 210.0376 (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid saccharic acid 25525-21-7 O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1 DSLZVSRJTYRBFB-LLEIAEIESA-N belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucuronic acid derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monosaccharides Organic oxides Polyols Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Fatty acid Fatty acyl Glucuronic acid or derivatives Hydrocarbon derivative Hydroxy acid Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monosaccharide Organic oxide Polyol Secondary alcohol Dicarboxylic acids glucaric acid water_solubility 912 mg/mL logp 6.1 Wikipedia melting_point 125-126 °C Wikipedia logp -1.77 ALOGPS logs -0.52 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 2.83 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid ChemAxon average_mass 210.14 ChemAxon mono_mass 210.0376 ChemAxon smiles O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O ChemAxon formula C6H10O8 ChemAxon inchi InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1 ChemAxon inchikey DSLZVSRJTYRBFB-LLEIAEIESA-N ChemAxon polar_surface_area 155.52 ChemAxon refractivity 38.14 ChemAxon polarizability 16.8 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB022169 C00818 DB03603 30577 33037 16002 D-GLUCARATE C00034205 35926 Saccharic_acid 5633 Zoltaszek R, Hanausek M, Kilianska ZM, Walaszek Z: [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. Postepy Hig Med Dosw (Online). 2008 Sep 5;62:451-62. 18772850 Singh J, Gupta KP: Calcium glucarate prevents tumor formation in mouse skin. Biomed Environ Sci. 2003 Mar;16(1):9-16. 12747003 1.0 2020-03-18 23:22:28 UTC 2020-07-24 23:30:05 UTC CDB006172 Linoleic acid Linoleic acid is a doubly unsaturated fatty acid or polyunsaturated fatty acid (PUFA). It is also known as an omega-6 fatty acid, occurring widely in plant glycosides. In linoleic acid the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Linoleic acid is a colorless or white oil with a faint, fatty odor. Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and the lipids of cell membranes. Altered levels of linoleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Conjugated linoleic acids have been studied for their beneficial effects in the prevention and treatment of many diseases, including obesity, cancer, diabetes, and cardiovascular diseases (PMID: 27636835). Linoleic acid can be found in all living organisms, ranging from bacteria to humans, although it cannot be synthesized by mammals. In rats, a diet deficient in linoleate (the salt form of the acid) has been shown to cause mild skin scaling, hair loss, (PMID: 9144095) and poor wound healing (PMID: 10498749). Linoleic acid is abundant in many nuts, fatty seeds (flax seeds, hemp seeds, poppy seeds, sesame seeds, etc.) and their derived vegetable oils; comprising over half (by weight) of poppy seed, safflower, sunflower, corn, and soybean oils. Linoleic acid is used in making quick-drying oils, which are useful in oil paints and varnishes. Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. A number of reports have identified linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the skin (PMID: 9692305; PMID: 9749992). Linoleic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C18H32O2 280.45 280.2402 (2E)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-N,N'-bis[2-(4-hydroxyphenyl)ethyl]butanediimidic acid (2E)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-N,N'-bis[2-(4-hydroxyphenyl)ethyl]butanediimidic acid 2197-37-7 CCCCC\C=C/C\C=C/CCCCCCCC(O)=O InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- OYHQOLUKZRVURQ-HZJYTTRNSA-N belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Lignans, neolignans and related compounds Organic compounds Lignans, neolignans and related compounds Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Cinnamic acid amides Hydrocarbon derivatives Hydroxycinnamic acids and derivatives Methoxybenzenes Methoxyphenols N-acyl amines Organic oxides Organonitrogen compounds Phenoxy compounds Secondary carboxylic acid amides 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Cinnamic acid amide Cinnamic acid or derivatives Ether Fatty acyl Fatty amide Hydrocarbon derivative Hydroxycinnamic acid or derivatives Methoxybenzene Methoxyphenol Monocyclic benzene moiety N-acyl-amine Norlignan skeleton Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Secondary carboxylic acid amide water_solubility 0.139 mg/L Wikipedia logp 7.05 SANGSTER (1993) melting_point -8.5 °C boiling_point 229 °C at 16 mmHg Wikipedia logp 5.17 ALOGPS logs -5.71 ALOGPS logp 5.84 ChemAxon pka_strongest_acidic 3.43 ChemAxon pka_strongest_basic 5.46 ChemAxon iupac (2E)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-N,N'-bis[2-(4-hydroxyphenyl)ethyl]butanediimidic acid ChemAxon average_mass 280.45 ChemAxon mono_mass 280.2402 ChemAxon smiles CCCCC\C=C/C\C=C/CCCCCCCC(O)=O ChemAxon formula C18H32O2 ChemAxon inchi InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- ChemAxon inchikey OYHQOLUKZRVURQ-HZJYTTRNSA-N ChemAxon polar_surface_area 164.56 ChemAxon refractivity 177.9 ChemAxon polarizability 67.32 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C17911 10438919 Fuke G, Nornberg JL: Systematic evaluation on the effectiveness of conjugated linoleic acid in human health. Crit Rev Food Sci Nutr. 2017 Jan 2;57(1):1-7. doi: 10.1080/10408398.2012.716800. 27636835 Cunnane SC, Anderson MJ: Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and [1-14C]linoleate oxidation. J Lipid Res. 1997 Apr;38(4):805-12. 9144095 Ruthig DJ, Meckling-Gill KA: Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6. J Nutr. 1999 Oct;129(10):1791-8. doi: 10.1093/jn/129.10.1791. 10498749 Letawe C, Boone M, Pierard GE: Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones. Clin Exp Dermatol. 1998 Mar;23(2):56-8. doi: 10.1046/j.1365-2230.1998.00315.x. 9692305 Ando H, Ryu A, Hashimoto A, Oka M, Ichihashi M: Linoleic acid and alpha-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin. Arch Dermatol Res. 1998 Jul;290(7):375-81. doi: 10.1007/s004030050320. 9749992 1.0 2020-03-18 23:22:30 UTC 2020-09-11 20:08:58 UTC CDB006173 Malic acid Malic acid is odorless and a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. Apples contain malic acid, which contributes to the sourness of a green apple. Indeed, malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. In its ionized form, malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. Malic acid is an extremely weak acidic compound (based on its pKa). Malic acid exists in all living organisms, ranging from bacteria to humans. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats, it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production. Malic acid is abundant in many fruits and is the main acid found in apricots, blackberries, blueberries, cherries, mirabelles, peaches, pears, plums, and quince. Malic acid is also present in grapes and in most wines with concentrations as high as 5 g/l. The taste of malic acid is very clear and pure in rhubarb, a plant for which it is the primary flavor. It is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips. Therefore malic acid is a potential biomarker for the consumption of these foods. (+)-D-Malic acid (R)-2-Hydroxybutanedioic acid 2-HYDROXY-succinIC ACID D-Malate (+)-D-Malate (R)-2-Hydroxybutanedioate 2-HYDROXY-succinate (R)-Malate (R)-Hydroxybutanedioic acid D-(+)-Malic acid D-Hydroxybutanedioic acid Hydroxy-(R)-butanedioic acid R-Malic acid D-Malic acid C4H6O5 134.09 134.0215 (2R)-2-hydroxybutanedioic acid .+-.-malic acid 636-61-3 O[C@H](CC(O)=O)C(O)=O InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 BJEPYKJPYRNKOW-UWTATZPHSA-N belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Beta hydroxy acids and derivatives Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Beta hydroxy acids and derivatives Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives Organic oxides Secondary alcohols Short-chain hydroxy acids and derivatives Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Short-chain hydroxy acid malic acid water_solubility 364 mg/mL at 20 °C logp -1.26 melting_point 101 °C boiling_point 306.4 °C Wikipedia logp -0.87 ALOGPS logs 0.21 ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 3.2 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (2R)-2-hydroxybutanedioic acid ChemAxon average_mass 134.09 ChemAxon mono_mass 134.0215 ChemAxon smiles O[C@H](CC(O)=O)C(O)=O ChemAxon formula C4H6O5 ChemAxon inchi InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 ChemAxon inchikey BJEPYKJPYRNKOW-UWTATZPHSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 24.88 ChemAxon polarizability 10.93 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB03499 83793 DMR 92824 FDB008115 C00497 30796 Malic_acid CPD-660 Li D, Li W, Wang Q, Yang Z, Hou Z: Concise synthesis of Cannabisin G. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5095-8. doi: 10.1016/j.bmcl.2010.07.028. Epub 2010 Jul 11. 20667725 1.0 2020-03-18 23:22:32 UTC 2020-08-04 22:28:39 UTC CDB006174 Myristic acid Myristic acid, also known as tetradecanoic acid or C14:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.. Myristic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has a waxy, fatty or soapy odor and a fatty, creamy or cheesy taste. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid is a naturally occurring saturated fatty acid found in most animal and vegetable fats. Some of the highest levels of myristic acid are found in nutmeg. In particular, nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butterfat, 8‚Äì14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats. It also comprises 14.49% of the fats from the fruit of the Durian species. Industrially myristic acid is used as an ingredient in soaps and cosmetics (From Dorland, 28th ed). In many eukaryotes (including humans), myristic acid is commonly added to the N-terminal glycine residue in receptor-associated kinases to confer membrane localization of the enzyme. This is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell (Wikipedia). Some research has pointed to myristic acid's positive effects on regulating HDL cholesterol and hence improving the HDL (good cholesterol) to total cholesterol ratio (PMID: 7644455). Myristic acid is a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 1-Tetradecanecarboxylic acid 14 14:0 14:00 Acide tetradecanoique C14 CH3-[CH2]12-COOH Myristinsaeure N-Tetradecan-1-Oic acid N-Tetradecanoic acid N-Tetradecoic acid Tetradecoic acid Tetradecanoate 1-Tetradecanecarboxylate N-Tetradecan-1-Oate N-Tetradecanoate N-Tetradecoate Tetradecoate Tetradecanoic acid Myristate 1-Tridecanecarboxylate 1-Tridecanecarboxylic acid Crodacid Myristic acid pure Myristoate Myristoic acid Tetradecanoic (myristic) acid Acid, tetradecanoic Acid, myristic FA(14:0) C14H28O2 228.37 228.2089 tetradecanoic acid myristic acid 544-63-8 CCCCCCCCCCCCCC(O)=O InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) TUNFSRHWOTWDNC-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Saturated fatty acids Straight chain fatty acids Straight chain fatty acids long-chain fatty acid straight-chain saturated fatty acid water_solubility 0.00107 mg/mL logp 6.11 SANGSTER (1993) melting_point 53.9 °C boiling_point 326.2 °C at 760 mmHg Wikipedia logp 6.10 ALOGPS logs -5.12 ALOGPS logp 5.37 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac tetradecanoic acid ChemAxon average_mass 228.37 ChemAxon mono_mass 228.2089 ChemAxon smiles CCCCCCCCCCCCCC(O)=O ChemAxon formula C14H28O2 ChemAxon inchi InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16) ChemAxon inchikey TUNFSRHWOTWDNC-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 67.88 ChemAxon polarizability 30.1 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB08231 FDB031009 10539 C06424 11005 28875 CPD-7836 Myristic_acid C00001228 215851 196 Kromhout D, Menotti A, Bloemberg B, Aravanis C, Blackburn H, Buzina R, Dontas AS, Fidanza F, Giampaoli S, Jansen A, et al.: Dietary saturated and trans fatty acids and cholesterol and 25-year mortality from coronary heart disease: the Seven Countries Study. Prev Med. 1995 May;24(3):308-15. doi: 10.1006/pmed.1995.1049. 7644455 1.0 2020-03-18 23:22:34 UTC 2020-07-22 22:11:10 UTC CDB006175 trans-Cinnamic acid Trans-cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acid can exist in both the cis and trans form, with the trans-form being most common. Trans-cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Trans-cinnamic acid occurs naturally in a number of plants. It is a sweet, balsam, or cinnamon tasting compound. Trans-cinnamic acid is characterized by a honey-like odor. Trans-cinnamic acid is found in a number of foods with the highest concentration found in chinese cinnamons (cinnamon bark), olives, and lingonberries and in a lower concentration in redcurrants, red raspberries, and corianders. Trans-cinnamic acid has also been detected, but not quantified in common oregano, pepper (spice), fennels, pomegranates, and european cranberries. Trans-cinnamic acid has also been shown to be a microbial metabolite as it is produced by microbes belonging to the Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas families (PMID: 16349793). In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine (PMID:20035037). Cinnamic acid is used in flavorings, the production of synthetic indigo, and certain pharmaceuticals. A major use of trans-cinnamic acid is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry. (2E)-3-Phenyl-2-propenoic acid (2E)-3-Phenylacrylic acid (e)-3-Phenyl-2-propenoic acid (e)-Cinnamate (e)-Cinnamic acid Benzeneacrylic acid PHENYLETHYLENECARBOXYLIC ACID trans-3-Phenylacrylic acid trans-beta-Carboxystyrene trans-Cinnamate trans-Zimtsaeure (2E)-3-Phenyl-2-propenoate (2E)-3-Phenylacrylate (e)-3-Phenyl-2-propenoate Benzeneacrylate PHENYLETHYLENECARBOXYLate trans-3-Phenylacrylate trans-b-Carboxystyrene trans-Β-carboxystyrene (2E)-2-Phenyl-2-propenoate (2E)-2-Phenyl-2-propenoic acid (e)-3-Phenylacrylate (e)-3-Phenylacrylic acid (e)-3-Phenylprop-2-enoate (e)-3-Phenylprop-2-enoic acid trans-3-Phenyl-2-propenoate trans-3-Phenyl-2-propenoic acid Cinnamic acid, 14C-labeled CPD Cinnamic acid, 2-(14)C-labeled CPD Cinnamic acid, 3-(14)C-labeled CPD Cinnamic acid, (Z)-isomer Cinnamic acid, 2-(13)C-labeled CPD Cinnamic acid, 3H-labeled CPD (e)-isomer Cinnamic acid, 3H-labeled CPD (Z)-isomer Cinnamic acid, ion(1-)-(e)-isomer Cinnamic acid, sodium salt Cinnamic acid, sodium salt(e)-isomer Cinnamic acid, sodium salt(Z)-isomer Cinnamic acid, (trans)-(e)-isomer Cinnamic acid, 14C-labeled CPD (e)-isomer Cinnamic acid, ion(1-) Cinnamic acid, nickel (+2) salt Cinnamic acid, potassium salt Cinnamic acid, zinc salt(e)-isomer Cinnamic acid, 13C-labeled CPD Cinnamic acid (2E)-3-Phenylprop-2-enoic acid (2E)-Cinnamic acid 3-Phenyl-(e)-2-propenoic acid 3-Phenyl-2-propenoic acid 3-Phenylacrylic acid Phenylacrylic acid beta-Phenylacrylic acid Β-phenylacrylic acid trans-Cinnamic acid C9H8O2 148.16 148.0524 (2E)-3-phenylprop-2-enoic acid cinnamic acid 140-10-3 OC(=O)\C=C\C1=CC=CC=C1 InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ WBYWAXJHAXSJNI-VOTSOKGWSA-N belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Cinnamic acids Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Cinnamic acids Aromatic homomonocyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Styrenes Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Styrene Monolignols cinnamic acid water_solubility 0.546 mg/mL logp 2.13 HANSCH,C ET AL. (1995) melting_point 133 °C boiling_point 300 °C Wikipedia logp 2.38 ALOGPS logs -2.38 ALOGPS logp 2.14 ChemAxon pka_strongest_acidic 4.51 ChemAxon iupac (2E)-3-phenylprop-2-enoic acid ChemAxon average_mass 148.16 ChemAxon mono_mass 148.0524 ChemAxon smiles OC(=O)\C=C\C1=CC=CC=C1 ChemAxon formula C9H8O2 ChemAxon inchi InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ ChemAxon inchikey WBYWAXJHAXSJNI-VOTSOKGWSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 43.06 ChemAxon polarizability 15.43 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012052 444539 392447 C10438 35697 549 C00029961 Cinnamic_acid 5880 CPD-674 Douros JD, Frankenfeld JW: Effects of Culture Conditions on Production of trans-Cinnamic Acid from Alkylbenzenes by Soil Microorganisms. Appl Microbiol. 1968 Feb;16(2):320-5. 16349793 Vogt T: Phenylpropanoid biosynthesis. Mol Plant. 2010 Jan;3(1):2-20. doi: 10.1093/mp/ssp106. Epub 2009 Dec 24. 20035037 1.0 2020-03-18 23:22:36 UTC 2020-08-04 22:28:39 UTC CDB006176 Stigmasterol Stigmasterol, also known as poriferasterol or phytosterol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmasterol is a phytosterol, meaning it is steroid derived from plants. ,It is very hydrophobic, practically insoluble in water, and relatively neutral. Stigmasterol is among the most abundant of plant sterols with its major function being to maintain the structure and physiology of cell membranes. It is found in plant fats or oils associated with various vegetables, legumes, nuts, and seeds such as¬†soybean,¬†calabar bean, rape seed and various herbs. Stigmasterol is also a constituent of unpasteurized milk. Pasteurization is known to inactivate stigmasterol. Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Consumption of 2 grams per day of plant sterols is associated with a reduction in blood LDL cholesterol of 8-10% (PMID: 29267628). As the typical western diet contains only about 300 mg/day of phytosterols, foods enriched with phytosterols are usually used to achieve the recommended intake (PMID: 29267628). The mechanism behind phytosterols lowering cholesterol involves the inhibition of the incorporation of cholesterol into micelles in the gastrointestinal tract, which decreases the overall amount of cholesterol absorbed. This may in turn help to control body total plasma cholesterol levels, as well as modify HDL, LDL and TAG levels in blood. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people wishing to lower their cholesterol levels. More recently, stigmasterol has been identified as a potent and independent risk factor for cardiovascular disease. Accumulation of stigmasterol leads to left ventricle dysfunction, cardiac interstitial fibrosis and macrophage infiltration without atherosclerosis (PMID: 30675518). Stigmasterol has been found to be associated with phytosterolemia, a disease characterized by elevated levels of dietary plant sterols in the blood. (PMID: 30675518). (3beta,22E)-Stigmasta-5,22-dien-3-ol 5,22-Cholestadien-24-ethyl-3beta-ol beta-Stigmasterol Phytosterol Poriferasterol Stigmasta-5,22-dien-3beta-ol (3b,22E)-Stigmasta-5,22-dien-3-ol (3β,22E)-Stigmasta-5,22-dien-3-ol 5,22-Cholestadien-24-ethyl-3b-ol 5,22-Cholestadien-24-ethyl-3β-ol b-Stigmasterol β-Stigmasterol Stigmasta-5,22-dien-3b-ol Stigmasta-5,22-dien-3β-ol (24S)-5,22-Stigmastadien-3b-ol 17-(4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol Stigmasta-5,22-dien-3-b-ol Stigmasta-5,22-dien-3-beta-ol Stigmasterin (24S)-24-Ethylcholesta-5,22-dien-3beta-ol (24S)-24-Ethylcholesta-5,22-dien-3β-ol (24S)-5,22-Stigmastadien-3beta-ol (24S)-5,22-Stigmastadien-3β-ol (24S)-Stigmast-5,22-dien-3beta-ol (24S)-Stigmast-5,22-dien-3β-ol 24-Ethyl-5,22-cholestadien-3beta-ol 24-Ethyl-5,22-cholestadien-3β-ol 24beta-Ethyl-5,22-cholestadien-3beta-ol 24β-Ethyl-5,22-cholestadien-3β-ol Stigmasta-5,22(E)-dien-3beta-ol Stigmasta-5,22(E)-dien-3β-ol Stigmasterol delta5,22-Stigmastadien-3beta-ol delta5-Stigmasterol Δ5,22-Stigmastadien-3β-ol Δ5-Stigmasterol C29H48O 412.7 412.3705 (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol 83-48-7 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 HCXVJBMSMIARIN-PHZDYDNGSA-N belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmastanes and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Stigmastanes and derivatives Aliphatic homopolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids C24-propyl sterols and derivatives Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols Triterpenoids 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound C24-propyl-sterol-skeleton Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Stigmastane-skeleton Triterpenoid 3beta-sterol Stigmastane and derivatives Stigmasterols and C24-ethyl derivatives Stigmasterols and C24-ethyl derivatives phytosterols stigmastane melting_point 170 °C boiling_point 490.4 °C Wikipedia logp 6.95 ALOGPS logs -7.18 ALOGPS logp 7.48 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol ChemAxon average_mass 412.7 ChemAxon mono_mass 412.3705 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@@H](CC)C(C)C ChemAxon formula C29H48O ChemAxon inchi InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 ChemAxon inchikey HCXVJBMSMIARIN-PHZDYDNGSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 130.88 ChemAxon polarizability 53.55 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001936 4444352 5280794 C05442 28824 C00023774 CPD-4162 Stigmasterol 168 Cabral CE, Klein MRST: Phytosterols in the Treatment of Hypercholesterolemia and Prevention of Cardiovascular Diseases. Arq Bras Cardiol. 2017 Nov;109(5):475-482. doi: 10.5935/abc.20170158. 29267628 Tao C, Shkumatov AA, Alexander ST, Ason BL, Zhou M: Stigmasterol accumulation causes cardiac injury and promotes mortality. Commun Biol. 2019 Jan 16;2:20. doi: 10.1038/s42003-018-0245-x. eCollection 2019. 30675518 1.0 2020-03-18 23:22:39 UTC 2020-07-24 23:30:05 UTC CDB006177 Threonic acid Threonic acid also known as threonate, belongs to the class of organic compounds known as sugar acids. Sugar acids are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is a weak acid (based on its pKa). Threonic acid is derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). Threonic acid is probably derived from glycated proteins or from the degradation of ascorbic acid. It is a normal component is aqueous humour and blood (PMID: 10420182). One recent study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID: 21034532). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). Threonate has also been found to be a microbial metabolite (PMID: 20615997). Threonate (R*,s*)-2,3,4-trihydroxy-butanoate (R*,s*)-2,3,4-trihydroxy-butanoic acid Threo-2,3,4-trihydroxybutyrate Threo-2,3,4-trihydroxybutyric acid Magnesium threonate Calcium threonate Threonic acid, (R-(r*,s*))-isomer 2,3,4-Trihydroxy-(threo)-butanoic acid Calcium L-threonate Threonic acid, (r*,r*)-isomer ClariMem L-TAMS compound L-Threonic acid magnesium salt MMFS-01 D-Threonate Threonic acid C4H8O5 136.1 136.0372 (2S,3R)-2,3,4-trihydroxybutanoic acid threonic acid 3909-12-4 OC[C@@H](O)[C@H](O)C(O)=O InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1 JPIJQSOTBSSVTP-GBXIJSLDSA-N belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Polyols Primary alcohols Secondary alcohols Short-chain hydroxy acids and derivatives Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol Short-chain hydroxy acid Sugar acid threonic acid logp -2.11 ALOGPS logs 0.55 ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 3.4 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R)-2,3,4-trihydroxybutanoic acid ChemAxon average_mass 136.1 ChemAxon mono_mass 136.0372 ChemAxon smiles OC[C@@H](O)[C@H](O)C(O)=O ChemAxon formula C4H8O5 ChemAxon inchi InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1 ChemAxon inchikey JPIJQSOTBSSVTP-GBXIJSLDSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 26.35 ChemAxon polarizability 11.61 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB022331 133224 151152 C01620 49059 38497 Threonic acid 5891 Harding JJ, Hassett PC, Rixon KC, Bron AJ, Harvey DJ: Sugars including erythronic and threonic acids in human aqueous humour. Curr Eye Res. 1999 Aug;19(2):131-6. doi: 10.1076/ceyr.19.2.131.5334. 10420182 Kwack MH, Ahn JS, Kim MK, Kim JC, Sung YK: Preventable effect of L-threonate, an ascorbate metabolite, on androgen-driven balding via repression of dihydrotestosterone-induced dickkopf-1 expression in human hair dermal papilla cells. BMB Rep. 2010 Oct;43(10):688-92. doi: 10.5483/BMBRep.2010.43.10.688. 21034532 van Duynhoven J, Vaughan EE, Jacobs DM, Kemperman RA, van Velzen EJ, Gross G, Roger LC, Possemiers S, Smilde AK, Dore J, Westerhuis JA, Van de Wiele T: Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci U S A. 2011 Mar 15;108 Suppl 1:4531-8. doi: 10.1073/pnas.1000098107. Epub 2010 Jun 25. 20615997 1.0 2020-03-18 23:22:41 UTC 2020-08-04 22:28:39 UTC CDB006178 Behenic acid Behenic acid, also known as docosanoate, C22:0 or 1-docosanoic acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Behenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 ¬∞C and boiling point of 306 ¬∞C. It is a major component of Ben oil (or behen oil), which is extracted from the seeds of the Ben-oil tree (Moringa oleifera). Behenic acid is also found in canola oil and peanut oil. As a dietary oil, behenic acid is poorly absorbed. In spite of its low bioavailability compared with oleic acid, behenic acid is a cholesterol-raising (LDL) saturated fatty acid in humans and is therefore not a suitable substitute for palmitic acid in manufactured triacylglycerols (PMID: 11124748). Behenic acid is often used to give hair conditioners and moisturizers their smoothing properties. It is also used in lubricating oils, and as a solvent evaporation retarder in paint removers. Behenic acid amide is used as an anti-foaming agent in detergents, floor polishes and dripless candles. Behenic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 1-Docosanoic acid Behensaeure CH3-[CH2]20-COOH Docosanic acid Docosanoate Docosansaeure Docosoic acid Dokosansaeure N-Docosanoic acid 1-Docosanoate Docosanate Docosanoic acid Docosoate N-Docosanoate Behenate FA(22:0) Behenic acid C22H44O2 340.58 340.3341 docosanoic acid behenic acid 112-85-6 CCCCCCCCCCCCCCCCCCCCCC(O)=O InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24) UKMSUNONTOPOIO-UHFFFAOYSA-N belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Very long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Very long-chain fatty acid Saturated fatty acids Straight chain fatty acids Straight chain fatty acids long-chain fatty acid straight-chain saturated fatty acid water_solubility 1.6e-05 mg/mL melting_point 81 °C boiling_point 306 °C Wikipedia logp 9.19 ALOGPS logs -7.05 ALOGPS logp 8.92 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac docosanoic acid ChemAxon average_mass 340.58 ChemAxon mono_mass 340.3341 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C22H44O2 ChemAxon inchi InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24) ChemAxon inchikey UKMSUNONTOPOIO-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 104.69 ChemAxon polarizability 47.25 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB005830 7923 8215 C08281 28941 C00001211 Behenic acid 260 Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. doi: 10.1093/ajcn/73.1.41. 11124748 1.0 2020-03-18 23:22:43 UTC 2020-11-04 16:20:29 UTC CDB000044 Ferulic acid Ferulic acid, also known as (e)-ferulate or trans-ferulate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is a moderately weak acid (based on its pKa). Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. In humans it can be readily absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernels. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with a variety of plant proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), ferulic acid readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer‚Äôs disease (PMID: 17127365, 1398220, 15453708, 9878519). Ferulic acid can be produced by a number of microbes including Pseudomonas and Saccharomyces (PMID: 8395165). It possesses antioxidant, anti-aging and anti-inflammatory properties. It protects the skin from damage by UV light and is used in skin care, sun care, hair care and color cosmetics. (e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid (e)-4'-Hydroxy-3'-methoxycinnamic acid (e)-4-Hydroxy-3-methoxycinnamic acid (e)-Ferulic acid 3-(4-Hydroxy-3-methoxyphenyl)propenoic acid 3-Methoxy-4-hydroxy-trans-cinnamic acid 4-Hydroxy-3-methoxycinnamic acid trans-4-Hydroxy-3-methoxycinnamic acid trans-Ferulic acid 3-Methoxy-4-hydroxy-trans-cinnamate 4-Hydroxy-3-methoxycinnamate (e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate (e)-4'-Hydroxy-3'-methoxycinnamate (e)-4-Hydroxy-3-methoxycinnamate (e)-Ferulate 3-(4-Hydroxy-3-methoxyphenyl)propenoate trans-4-Hydroxy-3-methoxycinnamate trans-Ferulate Ferulate 8,8'-Diferulic acid Ferulic acid, (e)-isomer Ferulic acid, monosodium salt Sodium ferulate Ferulic acid, (Z)-isomer (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid (e)-4-Hydroxy-3-methoxy-cinnamate (e)-4-Hydroxy-3-methoxy-cinnamic acid (2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid (2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid (e)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid Fumalic acid 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid 3-Methoxy-4-hydroxycinnamic acid 4'-Hydroxy-3'-methoxycinnamic acid Coniferic acid Ferulaic acid Ferulic acid 4’-Hydroxy-3’-methoxycinnamic acid C10H10O4 194.18 194.0579 (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid ferulic acid 537-98-4 COC1=C(O)C=CC(\C=C\C(O)=O)=C1 InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ KSEBMYQBYZTDHS-HWKANZROSA-N belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Hydroxycinnamic acids Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acids Cinnamic acids Coumaric acids and derivatives Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives Organic oxides Phenoxy compounds Styrenes 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Coumaric acid or derivatives Ether Hydrocarbon derivative Hydroxycinnamic acid Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Styrene Coniferyl alcohol derivatives ferulic acids logp 1.51 HANSCH,C ET AL. (1995) melting_point 168 - 171 °C logp 1.58 ALOGPS logs -2.33 ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 3.77 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid ChemAxon average_mass 194.18 ChemAxon mono_mass 194.0579 ChemAxon smiles COC1=C(O)C=CC(\C=C\C(O)=O)=C1 ChemAxon formula C10H10O4 ChemAxon inchi InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ ChemAxon inchikey KSEBMYQBYZTDHS-HWKANZROSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 51.5 ChemAxon polarizability 19.18 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01494 FDB012802 393368 DB07767 17620 445858 499 C00002743 FERULIC-ACID Ferulic_Acid 4156 Mancuso C, Scapagini G, Curro D, Giuffrida Stella AM, De Marco C, Butterfield DA, Calabrese V: Mitochondrial dysfunction, free radical generation and cellular stress response in neurodegenerative disorders. Front Biosci. 2007 Jan 1;12:1107-23. doi: 10.2741/2130. 17127365 Graf E: Antioxidant potential of ferulic acid. Free Radic Biol Med. 1992 Oct;13(4):435-48. doi: 10.1016/0891-5849(92)90184-i. 1398220 Fukuoka K, Sawabe A, Sugimoto T, Koga M, Okuda H, Kitayama T, Shirai M, Komai K, Komemushi S, Matsuda K: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. J Agric Food Chem. 2004 Oct 6;52(20):6326-9. doi: 10.1021/jf0351164. 15453708 Bourne LC, Rice-Evans C: Bioavailability of ferulic acid. Biochem Biophys Res Commun. 1998 Dec 18;253(2):222-7. doi: 10.1006/bbrc.1998.9681. 9878519 Huang Z, Dostal L, Rosazza JP: Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens. Appl Environ Microbiol. 1993 Jul;59(7):2244-50. 8395165 1.0 2020-03-18 23:22:45 UTC 2020-07-07 00:34:49 UTC CDB000045 Acetaldehyde Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are aldehydes with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol; which is mediated by the enzyme alcohol dehydrogenase 1B. In addition, acetaldehyde can be converted into acetic acid; which is mediated by mitochondrial aldehyde dehydrogenases. Industrially, the main method of production of acetaldehyde is via the oxidation of ethylene via the Wacker process. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process for producing acetaldehyde exceeded 2 million tonnes annually. Acetaldehyde is found in a number of different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine), Acetaldehyde has also been detected, but not quantified in, several different foods, such as malabar plums, malus (crabapple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. As a food constituent, acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and Crohn's disease. Acetaldehyde has also been linked to several inborn metabolic disorders including aldehyde dehydrogenase deficiency (III). The level at which an average consumer can detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Plastics Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. Acetaldehyde is known to be the most abundant carcinogen in tobacco smoke; it is easily dissolved in saliva while smoking (PMID:17382522, PMID:21556207). Acetaldehyd Acetaldehydes Acetic aldehyde Azetaldehyd Ethanal Ethyl aldehyde Aldehyde C2H4O 44.05 44.0262 acetaldehyde acetaldehyde 75-07-0 CC=O InChI=1S/C2H4O/c1-2-3/h2H,1H3 IKHGUXGNUITLKF-UHFFFAOYSA-N belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Short-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Organic oxide Short-chain aldehyde aldehyde an <i>n</i>-alkanal water_solubility 1000.0 mg/mL logp -0.34 TSCATS melting_point -123 °C boiling_point 20.2 °C Wikipedia logp -0.01 ALOGPS logs 0.71 ALOGPS logp -0.38 ChemAxon pka_strongest_acidic 16.73 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac acetaldehyde ChemAxon average_mass 44.05 ChemAxon mono_mass 44.0262 ChemAxon smiles CC=O ChemAxon formula C2H4O ChemAxon inchi InChI=1S/C2H4O/c1-2-3/h2H,1H3 ChemAxon inchikey IKHGUXGNUITLKF-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 11.72 ChemAxon polarizability 4.48 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008297 C00084 172 177 15343 C00007392 33792 Acetaldehyde 3200 ACETALD Talhout R, Opperhuizen A, van Amsterdam JG: Role of acetaldehyde in tobacco smoke addiction. Eur Neuropsychopharmacol. 2007 Oct;17(10):627-36. doi: 10.1016/j.euroneuro.2007.02.013. Epub 2007 Mar 23. 17382522 Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A: Hazardous compounds in tobacco smoke. Int J Environ Res Public Health. 2011 Feb;8(2):613-28. doi: 10.3390/ijerph8020613. Epub 2011 Feb 23. 21556207 1.0 2020-03-18 23:22:49 UTC 2020-07-31 20:34:15 UTC CDB000047 Methanol Methanol, also known as methyl alcohol or wood alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Methanol is the simplest of alcohols, consisting of a methyl group coupled to a hydroxyl group. Methanol was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide. Methanol is a light, volatile, colorless, flammable liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (drinking alcohol). Methanol is, however, far more toxic than ethanol. The target of methanol toxicity in the eye is the retina, specifically the optic disk and optic nerve. Visual disturbances develop between 18h to 48h after ingestion and range from mild photophobia and blurred vision to markedly reduced visual acuity and complete blindness. The toxicity of methanol is due to the metabolic products of alcohol dehydrogenase (ADH) and aldehyde dehydrogenase. Methanol is metabolized to formaldehyde by alcohol dehydrogenase, then to formate by formaldehyde dehydrogenase, and then to carbon dioxide by limited H4 folate. Despite its toxicity, methanol exists in low concentrations in all living organisms, ranging from bacteria to humans. Outside of the human body, methanol has been detected in several different foods, such as prairie turnips, mountain yams, mentha (mint), watermelons, milk, sweet oranges and pasta. Carbinol CH3OH MeOH Methyl alcohol Methylalkohol Spirit OF wood Wood alcohol Wood naphtha Wood spirit Alcool methylique Alcool metilico Colonial spirit Columbian spirit Columbian spirits Hydroxymethane Metanolo Methanol-water mixture Methyl hydroxide Methylol Metylowy alkohol Monohydroxymethane Pyro alcohol Pyroxylic spirit Alcohol, methyl Methoxide, sodium Sodium methoxide Alcohol, wood CH4O 32.04 32.0262 methanol methanol 67-56-1 CO InChI=1S/CH4O/c1-2/h2H,1H3 OKKJLVBELUTLKV-UHFFFAOYSA-N belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Primary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic acyclic compounds Hydrocarbon derivatives Aliphatic acyclic compound Hydrocarbon derivative Primary alcohol a short-chain alcohol alkyl alcohol one-carbon compound primary alcohol water_solubility 1000 mg/mL at 25 °C logp -0.77 HANSCH,C ET AL. (1995) melting_point -97.6 °C boiling_point 64.7 °C Wikipedia logp -1.38 ALOGPS logs 1.21 ALOGPS logp -0.52 ChemAxon pka_strongest_acidic 15.78 ChemAxon pka_strongest_basic -2.5 ChemAxon iupac methanol ChemAxon average_mass 32.04 ChemAxon mono_mass 32.0262 ChemAxon smiles CO ChemAxon formula CH4O ChemAxon inchi InChI=1S/CH4O/c1-2/h2H,1H3 ChemAxon inchikey OKKJLVBELUTLKV-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 8.26 ChemAxon polarizability 3.38 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008124 C00132 864 887 17790 METOH 33974 Methanol 4201 1.0 2020-03-18 23:22:51 UTC 2020-08-04 22:24:09 UTC CDB000048 Phytol Phytol, also known as trans-phytol or (e)-phytol, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, phytol is considered to be an isoprenoid lipid molecule. Phytol is a very hydrophobic molecule, practically insoluble in water, but soluble in most organic solvents. It is a colorless clear liquid with a floral, balsamic or waxy odor and a green, berry, tropical or waxy taste. Phytol is a constituent of chlorophyll and is produced in all photosynthesizing plants. Phytol is found in animals that consume plants wherein gut fermentation of ingested plant materials liberates phytol. Phytol has been detected, but not quantified in, several different foods, such as parsnips, rosemaries, red raspberries, common chokecherries, and white cabbages. . Although humans cannot derive phytanic acid from chlorophyll, they can convert free phytol into phytanic acid which is then stored in fats. Refsum disease is an autosomal recessive disorder that results in the accumulation of large stores of phytanic acid in tissues. This disease manifests with peripheral polyneuropathy, cerebellar ataxia, retinitis pigmentosa, anosmia, and hearing loss (PMID:17956237). Phytol and/or its metabolites have been reported to bind to and/or activate the transcription factors PPAR-alpha and retinoid X receptor (RXR). Phytol is used in the fragrance industry and in cosmetics, shampoos, toilet soaps, household cleaners, and detergents. In one study (PMID: 6991645) phytol was the only diterpene reported to exist in the essential oil of cannabis. Phytol is also used in some Cannabis distillate vapes as a diluent (2E,7R,11R)-3,7,11,15-Tetramethyl-2-hexadecen-1-ol trans-Phytol 3,7,11,15-Tetramethylhexadec-2-en-1-ol (e)-Phytol (7R,11R,2E)-Phytol (E,R,R)-Phytol C20H40O 296.54 296.3079 (2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol phytol 150-86-7 CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1 BOTWFXYSPFMFNR-PYDDKJGSSA-N belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Acyclic diterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Diterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Long-chain fatty alcohols Primary alcohols Acyclic diterpenoid Alcohol Aliphatic acyclic compound Fatty acyl Fatty alcohol Hydrocarbon derivative Long chain fatty alcohol Organic oxygen compound Organooxygen compound Primary alcohol Acyclic diterpenoids Acyclic diterpenoids Linear diterpenes diterpenoid long-chain primary fatty alcohol melting_point < 25 °C boiling_point 203 - 204 °C at 10 mmHg Wikipedia logp 7.89 ALOGPS logs -6.43 ALOGPS logp 7.04 ChemAxon pka_strongest_acidic 16.33 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol ChemAxon average_mass 296.54 ChemAxon mono_mass 296.3079 ChemAxon smiles CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO ChemAxon formula C20H40O ChemAxon inchi InChI=1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1 ChemAxon inchikey BOTWFXYSPFMFNR-PYDDKJGSSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 96.24 ChemAxon polarizability 40.33 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01389 FDB031117 4444094 17327 5280435 C00003467 PHYTOL Phytol 391 Wierzbicki AS: Peroxisomal disorders affecting phytanic acid alpha-oxidation: a review. Biochem Soc Trans. 2007 Nov;35(Pt 5):881-6. doi: 10.1042/BST0350881. 17956237 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:22:54 UTC 2020-08-04 22:24:09 UTC CDB000049 Phosphoric acid Phosphoric acid or free phosphate, also known as H3PO4, belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion. Phosphate is a moderately acidic compound (based on its pKa). When phosphorous pentoxide is dissolved in water it produces phosphoric acid. Phosphoric acid is a colorless, odorless phosphorus-containing inorganic acid with a bland taste. Phosphate, in the form of phosphoric acid, phosphate ions (H2PO4 or HPO4 ‚Äì at neutral pH) or various salts of phosphate, exists in all living species, ranging from bacteria to plants to humans. Free orthophosphate anions can be released by the hydrolysis of the phosphoanhydride bonds in ATP or ADP. These phosphorylation and dephosphorylation reactions are the immediate storage and source of energy for many metabolic processes. ATP and ADP are often referred to as high-energy phosphates. An important occurrence of phosphates in biological systems is as the structural material of bone and teeth. These structures are made of crystalline calcium phosphate in the form of hydroxyapatite. Vitamin D, which helps stimulate bone growth and stability, stimulates phosphate absorption, an effect reported to precede its action on calcium ion transport. Phosphate supplementation of the diet of rodents has been shown to lead to reduction in the incidence of dental caries and different phosphates have different powers in reducing the cariogenic potential of the carbohydrates in a diet. Food-grade phosphoric acid (additive E338) is used to acidify foods and beverages such as various colas and jams, providing a tangy or sour taste. Soft drinks containing phosphoric acid, including Coca-Cola, are sometimes called phosphate sodas or phosphates. Phosphoric acid also has the potential to contribute to the formation of kidney stones, especially in those who have had kidney stones previously (PMID:25364887). Phosphate, in the form of phosphoric acid, is one of the simple acids found in cannabis plant (PMID: 6991645). [PO(OH)3] Acide phosphorique Acidum phosphoricum H3PO4 Orthophosphoric acid Phosphorsaeureloesungen Phosphorsaeure Phosphoric acid Orthophosphate Phosphate Diphosphate tetrasodium Marphos NFB ortho- Phosphoric acid Phosphoric acid (acd/name 4.0) Sodium pyrophosphate Sodium pyrophosphate decahydrate Sodium pyrophosphate decahydrate biochemica Sonac Tetra-sodium pyrophosphate Tetrasodium pyrophosphate 10-hydrate Tetrasodium pyrophosphate decahydrate White phosphoric acid K-Etchant Uni-etch Concise etchant Condact Hydrogen phosphoric acid Dihydrogen phosphate Hydrogen phosphate H3O4P 98.0 97.9769 phosphoric acid phosphoric acid 1339-32-8 OP(O)(O)=O InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4) NBIIXXVUZAFLBC-UHFFFAOYSA-N belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion. Non-metal phosphates Inorganic compounds Homogeneous non-metal compounds Non-metal oxoanionic compounds Non-metal phosphates Inorganic oxides Inorganic oxide Non-metal phosphate phosphoric acids water_solubility 1000 mg/mL MERCK INDEX (1996) logp 0.0 Wikipedia melting_point 40–42.4 °C Wikipedia boiling_point 212 °C Wikipedia logp -1 ChemAxon pka_strongest_acidic 1.8 ChemAxon iupac phosphoric acid ChemAxon average_mass 98.0 ChemAxon mono_mass 97.9769 ChemAxon smiles OP(O)(O)=O ChemAxon formula H3O4P ChemAxon inchi InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4) ChemAxon inchikey NBIIXXVUZAFLBC-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 14.65 ChemAxon polarizability 5.81 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00009 DB09394 FDB013380 1004 26078 C00007408 Phosphoric_Acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Qaseem A, Dallas P, Forciea MA, Starkey M, Denberg TD: Dietary and pharmacologic management to prevent recurrent nephrolithiasis in adults: a clinical practice guideline from the American College of Physicians. Ann Intern Med. 2014 Nov 4;161(9):659-67. doi: 10.7326/M13-2908. 25364887 1.0 2020-03-18 23:22:56 UTC 2020-08-04 22:24:09 UTC CDB000050 Arachidic acid Arachidic acid, also known as eicosanoic acid, is a saturated fatty acid with a 20-carbon chain. It belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Arachidic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a white crystalline solid.¬†Arachidic acid‚Äôs name derives from the Latin arachis‚Äîpeanut. It can be formed by the hydrogenation of arachidonic acid. Arachidic acid is a minor constituent of cupua√ßu butter (7%), perilla oil (0‚Äì1%), peanut oil (1.1‚Äì1.7%), corn oil (3%), Arabica coffee oil and cocoa butter (1%). It also constitutes 7.1% of the fats from the durian fruit. Arachidic acid is also found in cannabis (PMID:6991645). Arachidic acid occurs naturally in fish and vegetable oils. The salts and esters of arachidic acid are known as arachidates. Diets rich in saturated fats like arachidic acid are associated with increased levels of serum low density lipoproteins. In a study of arachidic acid on Arabica coffee oil (PMID: 29995918), the influence of high-temperature heating on composition and thermo-oxidative stability was studied. The investigated samples showed a stability to oxidation up to approx. 276.8 ÃäC -278.3 ÃäC and the heat treatment of the beans during the roasting process did not significantly affect the composition in fatty acids. Arabica coffee oil may be used in processes which require high-temperature heating, such as those employed by the food industry, or in the production of pastries. Arachidic acid is also used for the production of detergents, photographic materials and lubricants.¬†Arachidic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Arachic acid Arachidinic acid Arachinsaeure C20:0 CH3-[CH2]18-COOH Eicosanoic acid N-Eicosanoic acid Arachate Arachidinate Eicosanoate N-Eicosanoate Arachidate Eicosoic acid Icosanoic acid Eicosoate Icosanoate C 20 C20 Fatty acid FA(20:0) Peanut acid N-Eicosanic acid Arachidic acid C20H40O2 312.53 312.3028 icosanoic acid arachidic acid 506-30-9 CCCCCCCCCCCCCCCCCCCC(O)=O InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22) VKOBVWXKNCXXDE-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Saturated fatty acids Straight chain fatty acids Straight chain fatty acids long-chain fatty acid straight-chain saturated fatty acid logp 9.29 SANGSTER (1993) melting_point 75.4 °C boiling_point 328 °C Wikipedia logp 8.53 ALOGPS logs -6.80 ALOGPS logp 8.03 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac icosanoic acid ChemAxon average_mass 312.53 ChemAxon mono_mass 312.3028 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C20H40O2 ChemAxon inchi InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22) ChemAxon inchikey VKOBVWXKNCXXDE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 95.49 ChemAxon polarizability 42.91 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004028 10035 10467 C06425 28822 C00001209 48230 Arachidic_acid 401 ARACHIDIC_ACID Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Raba DN, Chambre DR, Copolovici DM, Moldovan C, Copolovici LO: The influence of high-temperature heating on composition and thermo-oxidative stability of the oil extracted from Arabica coffee beans. PLoS One. 2018 Jul 11;13(7):e0200314. doi: 10.1371/journal.pone.0200314. eCollection 2018. 29995918 1.0 2020-03-18 23:22:58 UTC 2020-08-04 22:24:09 UTC CDB000051 Raffinose Raffinose is a trisaccharide containing glucose, galactose, and fructose units. It belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Raffinose is an extremely weak basic (essentially neutral) compound (based on its pKa). Raffinose exists as a white crystalline powder and has a sweet taste approximately 10% that of sucrose. The raffinose family of oligosaccharides (RFOs) are alpha-galactosyl derivatives of sucrose, and the most common are the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous in the plant kingdom, being found in a large variety of seeds from many different families, and they rank second only to sucrose in abundance as soluble carbohydrates. Raffinose (and other RFOs) is non-digestible in humans and other monogastric animals (pigs and poultry) who do not possess the Œ±-GAL (alpha-galactosidase) enzyme to break down raffinose. In the lower intestine of most mammals, raffinose is fermented by gas-producing bacteria that possess the Œ±-GAL enzyme and make short-chain fatty acids (SCFA) (acetic, propionic, butyric acids) as well as the flatulence commonly associated with eating beans and other vegetables. Raffinose can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. In humans, raffinose is involved in galactose metabolism. Raffinose is one of at least 5 oligosaccharides that are found in cannabis plants (PMID: 6991645). Raffinose is used in skin moisturizers and smoothers, prebiotics (it allegedly promotes growth of lactobacilli and bifidobacteria), and as a food or drink additive. Either raffinose or sucrose can be used as a base substance for sucralose. 6g-alpha-D-Galactosylsucrose alpha-D-Galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranoside alpha-D-Galp-(1->6)-alpha-D-GLCP-(12)-beta-D-fruf Gossypose Melitose Melitriose Rafinose Raflinose 6g-a-D-Galactosylsucrose 6g-Α-D-galactosylsucrose a-D-Galactopyranosyl-(1->6)-a-D-glucopyranosyl b-D-fructofuranoside Α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl β-D-fructofuranoside a-D-Galp-(1->6)-a-D-GLCP-(12)-b-D-fruf Α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-fruf D-(+)-Raffinose D-Raffinose beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1→6)-alpha-D-glucopyranoside Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside Raffinose C18H32O16 504.44 504.169 (2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol raffinose 512-69-6 OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Oligosaccharides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds C-glycosyl compounds Hydrocarbon derivatives Ketals O-glycosyl compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Tetrahydrofurans Acetal Alcohol Aliphatic heteromonocyclic compound C-glycosyl compound Glycosyl compound Hydrocarbon derivative Ketal O-glycosyl compound Oligosaccharide Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Tetrahydrofuran raffinose family oligosaccharide trisaccharide water_solubility 203 mg/mL melting_point 80 °C logp -3.36 ALOGPS logs 0.12 ALOGPS logp -6.3 ChemAxon pka_strongest_acidic 11.7 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol ChemAxon average_mass 504.44 ChemAxon mono_mass 504.169 ChemAxon smiles OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O ChemAxon formula C18H32O16 ChemAxon inchi InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1 ChemAxon inchikey MUPFEKGTMRGPLJ-ZQSKZDJDSA-N ChemAxon polar_surface_area 268.68 ChemAxon refractivity 101.19 ChemAxon polarizability 46.17 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 16 ChemAxon donor_count 11 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00492 439242 16634 C00001145 Raffinose CPD-1099 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:23:00 UTC 2020-07-10 00:17:47 UTC CDB000052 Palmitoleic acid Palmitoleic acid, also known as palmitoleate or zoomaric acid or C16:1, is an omega-7 monounsaturated fatty acid that is found in plants (PMID: 11308350) such as cannabis plants (PMID:6991645) and marine sources (PMID: 19382347). It belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitoleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Palmitoleic acid exists in all living species, ranging from bacteria to humans. Macadamia nuts and buckthorn seed oil contain the cis isomer of palmitoleic acid. Palmitoleic acid is also found in mung beans, java plums, napa cabbages, cucurbita (gourd), and kiwis.. It is also a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Palmitoleic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and cirrhosis; palmitoleic acid has also been linked to the inborn metabolic disorder isovaleric acidemia. Palmitoleic acid has been reported to have beneficial effects on insulin sensitivity, cholesterol metabolism, and hemostasis. Other positive effects reported include lowering LDL cholesterol and increasing high-density lipoprotein cholesterol (HDL)(https://doi.org/10.1016/B978-1-78242-247-1.00004-1). Palmitoleic acid is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). (9Z)-Hexadecenoic acid (Z)-9-Hexadecenoic acid (Z)-Hexadec-9-enoic acid 16:1DElta9 9-cis-Hexadecenoic acid cis-9-Hexadecenoic acid cis-9-Palmitoleic acid cis-delta-9-Hexadecenoic acid cis-Delta(9)-Hexadecenoic acid cis-Palmitoleic acid Oleopalmitic acid Palmitolinoleic acid Zoomaric acid Zoomeric acid (9Z)-Hexadec-9-enoate (9Z)-Hexadecenoate (Z)-9-Hexadecenoate (Z)-Hexadec-9-enoate 9-cis-Hexadecenoate cis-9-Hexadecenoate cis-9-Palmitoleate cis-delta-9-Hexadecenoate cis-Δ-9-hexadecenoate cis-Δ-9-hexadecenoic acid cis-delta(9)-Hexadecenoate cis-Δ(9)-hexadecenoate cis-Δ(9)-hexadecenoic acid cis-Palmitoleate Oleopalmitate Palmitolinoleate Zoomarate Zoomerate (9Z)-Hexadec-9-enoic acid Palmitoleate 9-Hexadecenoate 9-Hexadecenoic acid Hexadecenoate Hexadecenoate (N-C16:1) Hexadecenoic acid Palmitoleic acid, (Z)-isomer Palmitoleic acid, (e)-isomer C16:1 trans-9 Palmitelaidic acid (9Z)-9-Hexadecenoic acid 9Z-Hexadecenoic acid C16:1 FA(16:1(9Z)) FA(16:1n7) cis-delta9-Hexadecenoic acid cis-Δ9-hexadecenoic acid Palmitoleic acid C16H30O2 254.41 254.2246 (9Z)-hexadec-9-enoic acid palmitoleic acid 373-49-9 CCCCCC\C=C/CCCCCCCC(O)=O InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- SECPZKHBENQXJG-FPLPWBNLSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Monounsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids hexadec-9-enoic acid melting_point -0.1 °C logp 6.71 ALOGPS logs -5.76 ALOGPS logp 5.89 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9Z)-hexadec-9-enoic acid ChemAxon average_mass 254.41 ChemAxon mono_mass 254.2246 ChemAxon smiles CCCCCC\C=C/CCCCCCCC(O)=O ChemAxon formula C16H30O2 ChemAxon inchi InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- ChemAxon inchikey SECPZKHBENQXJG-FPLPWBNLSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 78.2 ChemAxon polarizability 32.87 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04257 FDB031085 393216 445638 C08362 28716 C00029354 CPD-9245 246167 Palmitoleic acid 188 Yang B, Kallio HP: Fatty acid composition of lipids in sea buckthorn (Hippophae rhamnoides L.) berries of different origins. J Agric Food Chem. 2001 Apr;49(4):1939-47. doi: 10.1021/jf001059s. 11308350 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Polat S, Ozogul Y: Biochemical composition of some red and brown macro algae from the Northeastern Mediterranean Sea. Int J Food Sci Nutr. 2008 Nov-Dec;59(7-8):566-72. doi: 10.1080/09637480701446524. 19382347 1.0 2020-03-18 23:23:03 UTC 2020-08-04 22:24:09 UTC CDB000053 Hordenine Hordenine belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Hordenine, a strong basic compound, is a colorless solid that is soluble in organic solvents. Hordenine is biosynthesized by the stepwise¬†N-methylation of¬†tyramine, which is first converted to¬†N-methyltyramine by¬†tyramine N-methyltransferase and then is methylated to hordenine (PMID: 24257763). Hordenine exists in all living organisms, ranging from plants to humans. It is found in highest concentrations with barley (Hordeum species), from which its name is derived. Hordenine is also found in cannabis plants (PMID:6991645). Several varieties of plants in the family Cactacea (cacti) produce hordenine which, as a potent phenylethylamine alkaloid, has antibacterial and antibiotic properties (PMID: 30609368; PMID: 30128579). Hordenine has been found in several different foods, such as cereals and cereal products, corns, oats, sweet oranges, and tamarinds making it a potential biomarker for the consumption of these foods. People consuming beer brewed from barley will have higher levels of hordenine. However, hordenine in urine interferes with tests for morphine, heroin and other opioid drugs (PMID: 1618458). Hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the central nervous system and can promote weight loss by enhancing metabolism. 4-[2-(Dimethylamino)ethyl]phenol N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine N,N-Dimethyl-4-hydroxy-beta-phenethylamine N,N-Dimethyltyramine p-(2-Dimethylaminoethyl)phenol N,N-Dimethyl-4-hydroxy-b-phenethylamine N,N-Dimethyl-4-hydroxy-β-phenethylamine Hordenine hydrochloride Hordenine sulfate (2:1) Hordenine sulfate (1:1) 4-(2-Dimethylaminoethyl)phenol Anhalin Anhaline Cactine Eremursine Hordenin Hordetin N,N-Dimethyl-p-hydroxyphenethylamine Ordenina Ordenine p-Hydroxy-N,N-dimethylphenethylamine p-[2-(Dimethylamino)ethyl]phenol Peyocactine C10H15NO 165.23 165.1154 4-[2-(dimethylamino)ethyl]phenol hordenine 539-15-1 CN(C)CCC1=CC=C(O)C=C1 InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 KUBCEEMXQZUPDQ-UHFFFAOYSA-N belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Phenethylamines Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Hydrocarbon derivatives Organooxygen compounds Organopnictogen compounds Trialkylamines 1-hydroxy-2-unsubstituted benzenoid Amine Aralkylamine Aromatic homomonocyclic compound Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenethylamine Phenol Tertiary aliphatic amine Tertiary amine Tyramine derivatives phenethylamine alkaloid water_solubility 7 mg/mL melting_point 117.5 °C logp 1.76 ALOGPS logs -0.75 ALOGPS logp 1.63 ChemAxon pka_strongest_acidic 10.31 ChemAxon pka_strongest_basic 9.19 ChemAxon iupac 4-[2-(dimethylamino)ethyl]phenol ChemAxon average_mass 165.23 ChemAxon mono_mass 165.1154 ChemAxon smiles CN(C)CCC1=CC=C(O)C=C1 ChemAxon formula C10H15NO ChemAxon inchi InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 ChemAxon inchikey KUBCEEMXQZUPDQ-UHFFFAOYSA-N ChemAxon polar_surface_area 23.47 ChemAxon refractivity 51.34 ChemAxon polarizability 19.35 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 61609 FDB012750 68313 C06199 5764 C00001417 Hordenine 7055 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Meyer E: Separation of two distinct S-adenosylmethionine dependent N-methyltransferases involved in hordenine biosynthesis in Hordeum vulgare. Plant Cell Rep. 1982 Dec;1(6):236-9. doi: 10.1007/BF00272627. 24257763 Zhou JW, Ruan LY, Chen HJ, Luo HZ, Jiang H, Wang JS, Jia AQ: Inhibition of Quorum Sensing and Virulence in Serratia marcescens by Hordenine. J Agric Food Chem. 2019 Jan 23;67(3):784-795. doi: 10.1021/acs.jafc.8b05922. Epub 2019 Jan 14. 30609368 Zhou JW, Hou B, Liu GY, Jiang H, Sun B, Wang ZN, Shi RF, Xu Y, Wang R, Jia AQ: Attenuation of Pseudomonas aeruginosa biofilm by hordenine: a combinatorial study with aminoglycoside antibiotics. Appl Microbiol Biotechnol. 2018 Nov;102(22):9745-9758. doi: 10.1007/s00253-018-9315-8. Epub 2018 Aug 20. 30128579 Singh AK, Granley K, Misrha U, Naeem K, White T, Jiang Y: Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. Forensic Sci Int. 1992 Apr;54(1):9-22. doi: 10.1016/0379-0738(92)90076-9. 1618458 1.0 2020-03-18 23:23:05 UTC 2020-07-07 15:54:44 UTC CDB000054 p-Cymene p-Cymene, also known as p-cymol or isopropyltoluene, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. Thus, p-cymene is considered to be an isoprenoid lipid molecule. p-Cymene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.It has a role as a plant metabolite, a volatile oil component. p-Cymene 1-Isopropyl-4-methylbenzene 1-Methyl-4-(1-methylethyl)benzene 1-Methyl-4-(propan-2-yl)benzene 1-Methyl-4-isopropylbenzene 4-Cymene 4-Isopropyl-1-methylbenzene 4-Isopropyltoluene 4-Methyl-1-isopropylbenzene Cymene Isopropyltoluene p-Cimene p-Cymol p-Isopropyltoluene p-Methylcumene p-Methylisopropylbenzene Para-cymene 1-Isopropyl-4-methyl-benzene 1-Methyl-4-(1-methylethyl)-benzene 2-p-Tolylpropane 4-Isopropylbenzyl radical 4-Methyl-1-(propan-2-yl)benzene Camphogen Cymol Dolcymene p- Isopropylmethylbenzene p-Mentha-1,3,5-triene p-Methyl cumene p-Methyl-cumene Paracymene Paracymol 4-Methylisopropylbenzene C10H14 134.22 134.1096 1-methyl-4-(propan-2-yl)benzene cymene 99-87-6 CC(C)C1=CC=C(C)C=C1 InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 HFPZCAJZSCWRBC-UHFFFAOYSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds Aromatic hydrocarbons Cumenes Monocyclic monoterpenoids Phenylpropanes Toluenes Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Aromatic monoterpenoid Benzenoid Cumene Hydrocarbon Monocyclic benzene moiety Monocyclic monoterpenoid P-cymene Phenylpropane Toluene Unsaturated hydrocarbon Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids a monoterpenoid monoterpene toluenes water_solubility 0.0234 mg/mL at 25 °C logp 4.10 HANSCH,C ET AL. (1995) melting_point -68.9 °C logp 4.17 ALOGPS logs -3.90 ALOGPS logp 3.73 ChemAxon iupac 1-methyl-4-(propan-2-yl)benzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CC(C)C1=CC=C(C)C=C1 ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 ChemAxon inchikey HFPZCAJZSCWRBC-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 45.29 ChemAxon polarizability 17 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7183 FDB017358 7463 C06575 28768 C00003040 CPD-1001 P-cymene 1.0 2020-03-18 23:23:07 UTC 2020-08-04 22:24:11 UTC CDB000055 Eugenol Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from¬†guaiacol,¬†with an allyl chain substituted para to the¬†hydroxy¬†group. It is soluble in water, alcohol,¬†chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol exists in all eukaryotes, from yeast to humans. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. It is a noncannabinoid phenol compound found in cannabis plants (PMID: 6991645). Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the¬†liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID: 15089054; PMID: 935250) and acts as positive allosteric modulators of the GABAA¬†receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID: 27771920). 1,3,4-Eugenol 1-Allyl-3-methoxy-4-hydroxybenzene 1-Allyl-4-hydroxy-3-methoxybenzene 1-Hydroxy-2-methoxy-4-allylbenzene 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene 1-Hydroxy-2-methoxy-4-propenylbenzene 2-Hydroxy-5-allylanisole 2-Methoxy-1-hydroxy-4-allylbenzene 2-Methoxy-4-(2-propen-1-yl)phenol 2-Methoxy-4-(2-propenyl)phenol 2-Methoxy-4-allylphenol 2-Methoxy-4-prop-2-enylphenol 4-Allyl-1-hydroxy-2-methoxybenzene 4-Allyl-2-methoxyphenol 4-Allylcatechol-2-methyl ether 4-Allylguaiacol 4-Hydroxy-3-methoxy-1-allylbenzene Allylguaiacol Caryophyllic acid Eugenic acid p-Allylguaiacol p-Eugenol Caryophyllate Eugenate 2-Methoxy-4-(3-propenyl)phenol 2-Methoxy-4-(prop-2-en-1-yl)phenol 4-Allyl-2-methoxy-phenol 4-Allylcatechol 2-methyl ether 4-Hydroxy-3-methoxyallylbenzene 5-Allylguaiacol Engenol Eugenol (natural) Synthetic eugenol 2-Methoxy-4-(2'-propenyl)phenol 2-Methoxy-4-(2’-propenyl)phenol 2-Methoxy-4-[2-allyl]phenol 3-(3-Methoxy-4-hydroxyphenyl)propene 3-(4-Hydroxy-3-methoxyphenyl)-1-propene 4-Allenylguaiacol C10H12O2 164.2 164.0837 2-methoxy-4-(prop-2-en-1-yl)phenol eugenol 97-53-0 COC1=C(O)C=CC(CC=C)=C1 InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 RRAFCDWBNXTKKO-UHFFFAOYSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyphenols Organic compounds Benzenoids Phenols Methoxyphenols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Monolignols a monoterpenol a phenol monomethoxybenzene phenols phenylpropanoid melting_point −7.5 °C Wikipedia boiling_point 254 °C Wikipedia logp 2.66 ALOGPS logs -2.06 ALOGPS logp 2.61 ChemAxon pka_strongest_acidic 9.94 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxy-4-(prop-2-en-1-yl)phenol ChemAxon average_mass 164.2 ChemAxon mono_mass 164.0837 ChemAxon smiles COC1=C(O)C=CC(CC=C)=C1 ChemAxon formula C10H12O2 ChemAxon inchi InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3 ChemAxon inchikey RRAFCDWBNXTKKO-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 48.79 ChemAxon polarizability 17.9 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C10453 3314 FDB012171 13876103 EOL 4917 646 DB09086 C00000619 CPD-6481 Eugenol 4022 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS: Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases. Drug Dev Ind Pharm. 2004 Feb;30(2):195-203. doi: 10.1081/ddc-120028715. 15089054 Sell AB, Carlini EA: Anesthetic action of methyleugenol and other eugenol derivatives. Pharmacology. 1976;14(4):367-77. doi: 10.1159/000136617. 935250 Fujisawa S, Murakami Y: Eugenol and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:45-66. doi: 10.1007/978-3-319-41342-6_3. 27771920 1.0 2020-03-18 23:23:09 UTC 2020-08-04 22:24:12 UTC CDB000056 Nerol Nerol or (Z)-3,7-dimethyl-2,6-octadien-1-ol or cis-Geranial is formally classified as an alkylalcohol although it is biochemically a monoterpenoid synthesized from isoprene units. It is soluble in¬†water and very soluble in alcohol. Nerol is a naturally occurring organic compound found in the essential oils of many plants and was originally found in neroli oil, from which its name was derived. The largest natural source is palmarosa oil and it is the primary constituent of rose oil, palmarosa oil, and citronella oil (Java type) with in small quantities found in geranium, lemon, and many other essential oils. Different foods contain nerol with the highest concentration found in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. Nerol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals and in cannabis plants (PMID: 6991645) . Nerol has a sweet, citrus and floral flavor with a sweet rose-like odor. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. This alcohol is widely and frequently used in perfumery as it has a freshness to a rose base (PMID: 18640199). It is detected in small quantities in orange peel and together with other oils, was found to have antimicrobial properties (PMID: 27535797). (2Z)-3,7-Dimethyl-2,6-octadien-1-ol (Z)-3,7-Dimethyl-2,6-octadien-1-ol (Z)-3,7-Dimethylocta-2,6-dien-1-ol (Z)-Geraniol 2-cis-3,7-Dimethyl-2,6-octadien-1-ol cis-3,7-Dimethyl-2,6-octadien-1-ol cis-Geraniol Neryl alcohol (2E)3,7-Dimethyl-2,6-octadien-1-ol (2Z)3,7-Dimethyl-2,6-octadien-1-ol (cis)3,7-Dimethyl-2,6-octadien-1-ol (e)3,7-Dimethyl-2,6-octadien-1-ol (e)3,7-Dimethyl-octadien-1-ol (Z)3,7-Dimethyl-2,6-octadien-1-ol 2,6-Dimethyl-trans-2,6-octadien-8-ol 2-trans-3,7-Dimethyl-2,6-octadien-1-ol 2-trans-3,7-Dimethyl-2,6-octadiene-1-ol 2E-Geraniol 3,7-Dimethyl-2,6-octadien-1-ol 3,7-Dimethyl-octane-1-ol tetrahydro derivative 3,7-Dimethyl-trans-2, 6-octadien-1-ol 3,7-Dimethylocta-2,6-dien-1-ol beta-Geraniol Geraniol (natural) Geraniol alcohol Geranyl alcohol Guaniol Lemonol Nerol Nerol (natural) Nerolidyl diphosphate trans-3,7-Dimethyl-2,6-octadien-1-ol trans-Geraniol Vernol Geraniol, 2-(14)C-labeled, (e)-isomer Geraniol, titanium (4+) salt Geraniol, (Z)-isomer Geraniol, 1-(14)C-labeled, (e)-isomer Geraniol, (e)-isomer Geraniol (Z)-3,7-Dimethyl-2,6-octadienol (Z)-3,7-Dimethyloct-2,6-diene-1-ol (Z)-Nerol 3,7-Dimethyl-cis-2,6-octadien-1-ol cis-1-Hydroxy-3,7-dimethyl-2,6-octadiene beta-Nerol β-Nerol C10H18O 154.25 154.1358 (2Z)-3,7-dimethylocta-2,6-dien-1-ol nerol 106-25-2 CC(C)=CCC\C(C)=C/CO InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7- GLZPCOQZEFWAFX-YFHOEESVSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Fatty alcohols Hydrocarbon derivatives Primary alcohols Acyclic monoterpenoid Alcohol Aliphatic acyclic compound Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol 3,7-dimethylocta-2,6-dien-1-ol Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes water_solubility 0.531 mg/mL at 25 °C logp 3.47 GRIFFIN,S ET AL. (1999) melting_point < -15 °C boiling_point 224 - 225 °C at 745 mmHg Wikipedia logp 2.89 ALOGPS logs -2.05 ALOGPS logp 2.5 ChemAxon pka_strongest_acidic 16.33 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2Z)-3,7-dimethylocta-2,6-dien-1-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)=CCC\C(C)=C/CO ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7- ChemAxon inchikey GLZPCOQZEFWAFX-YFHOEESVSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 51.18 ChemAxon polarizability 19.29 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C09871 643820 FDB014945 558917 29452 C00000855 CPD-7978 Nerol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Lapczynski A, Foxenberg RJ, Bhatia SP, Letizia CS, Api AM: Fragrance material review on nerol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S241-4. doi: 10.1016/j.fct.2008.06.062. Epub 2008 Jul 2. 18640199 Geraci A, Di Stefano V, Di Martino E, Schillaci D, Schicchi R: Essential oil components of orange peels and antimicrobial activity. Nat Prod Res. 2017 Mar;31(6):653-659. doi: 10.1080/14786419.2016.1219860. Epub 2016 Aug 18. 27535797 1.0 2020-03-18 23:23:11 UTC 2020-08-04 22:24:13 UTC CDB000057 Hexanal Hexanal, 1-hexanal, n-hexanal, is also known as caproaldehyde or hexanaldehyde. It belongs to the class of organic compounds known as medium-chain aldehydes which have a chain length between 6 and 12 carbon atoms and therefore is considered a fatty aldehyde lipid molecule. Hexanal is a very hydrophobic molecule that is relatively neutral. It is a colorless clear liquid. It has a fresh green, fatty or grassy scent with a green, fatty, leafy or aldehydic taste. Hexanal exists in all eukaryotes, from yeast to humans. Hexanal is found in cannabis plants (PMID: 6991645). Different foods contain hexanal with the highest concentrations found in black walnuts, corns, and tea and with lower concentrations in common grapes, thornless blackberries, and tortilla. Hexanal has also been detected in palms, mentha (mint), wax gourds, grapes, and kiwis making hexanal a potential biomarker for the consumption of these foods. Hexanal has been used to increase post-harvest longevity and color of certain fruits ( https://doi.org/10.1016/B978-0-12-809807-3.00009-3). Hexanal was also detected in humans breastmilk samples. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal, together with higher levels of 2-hydroxyhexanal and 4-hydroxynonena, are associated with poorer patient prognosis (PMID: 17487452). Hexanal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group because its concentrations in uremic patients were found to exceed the normal general population concentrations (PMID: 22626821). Hexanal is a volatile compound that has been associated with the development of undesirable flavours and has been proposed as a potential marker of milk quality. Hexanal, a major breakdown product of linoleic acid (LA, n ‚Äì 6, an polyunsaturated fatty acid, PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products such as baby formulae and was correlated with the hexanal concentration (https://doi.org/10.1016/j.foodchem.2007.08.042). Caproaldehyde Caproic aldehyde Capronaldehyde Hexaldehyde Hexanaldehyde Hexylaldehyde n-Caproaldehyde n-Hexanal n-Hexylaldehyde 1-Hexanal Aldehyde C-6 C6 Aldehyde Hexan-1-al Hexoic aldehyde N-C5H11CHO N-Caproic aldehyde Hexanal n-Capronaldehyde C6H12O 100.16 100.0888 hexanal hexanal 66-25-1 CCCCCC=O InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3 JARKCYVAAOWBJS-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide Fatty aldehydes an <i>n</i>-alkanal water_solubility 5.64 mg/mL at 30 °C logp 1.78 HANSCH,C ET AL. (1995) melting_point -56 °C boiling_point 130 - 131 °C Wikipedia logp 2.37 ALOGPS logs -1.35 ALOGPS logp 1.65 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac hexanal ChemAxon average_mass 100.16 ChemAxon mono_mass 100.0888 ChemAxon smiles CCCCCC=O ChemAxon formula C6H12O ChemAxon inchi InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3 ChemAxon inchikey JARKCYVAAOWBJS-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 30.15 ChemAxon polarizability 12.32 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008068 5949 6184 C02373 121338 HEXANAL C00000357 Hexanal Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. 22626821 Zajdel A, Wilczok A, Slowinski J, Orchel J, Mazurek U: Aldehydic lipid peroxidation products in human brain astrocytomas. J Neurooncol. 2007 Sep;84(2):167-73. doi: 10.1007/s11060-007-9367-6. Epub 2007 May 9. 17487452 1.0 2020-03-18 23:23:13 UTC 2020-07-10 00:17:46 UTC CDB000058 Benzyl acetate Benzyl acetate, also known as benzyl ethanoate, is an organic ester formed from the condensation of benzyl alcohol and acetic acid. Benzyl acetate is a neutral compound with a sweet jasmine-like aroma and a sweet, apple, and apricot taste. Benzyl acetate is found in highest concentration in sweet basils and is detected in figs, fruits, pomes, tea, and alcoholic beverages making benzyl acetate a potential biomarker for the consumption of these foods. Benzyl acetate is used as a flavoring agent to impart jasmine or apple flavors to various cosmetics and personal care products like lotions, hair creams (https://doi.org/10.1016/B978-0-443-06241-4.00013-8). Benzyl alcohol was also found in cannabis plants (PMID: 6991645). Benzyl acetate is a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Acetic acid, benzyl ester Acetic acid, phenylmethyl ester Benzyl ethanoate Phenylmethyl ethanoate Acetate, benzyl ester Acetate, phenylmethyl ester Benzyl ethanoic acid Phenylmethyl ethanoic acid Benzyl acetic acid (Acetoxymethyl)benzene Acetato de bencilo Acetic acid benzyl ester Acetic acid phenylmethyl ester alpha-Acetoxytoluene Benzyl acetate + glycine combination Benzyl ester OF acetic acid Benzylester kyseliny octove FEMA 2135 Nchem.167-comp5 Phenylmethyl acetate Plastolin I (14C)Benzyl acetate Benzyl (1-14C)acetate Benzyl (2-14C)acetate C9H10O2 150.17 150.0681 benzyl acetate benzyl acetate 140-11-4 CC(=O)OCC1=CC=CC=C1 InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3 QUKGYYKBILRGFE-UHFFFAOYSA-N belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyloxycarbonyls Organic compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls Aromatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aromatic homomonocyclic compound Benzyloxycarbonyl Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound a small molecule acetate ester water_solubility 3.1 mg/mL at 25 °C logp 1.96 melting_point -51.3 °C boiling_point 212 °C Wikipedia logp 2.07 ALOGPS logs -2.46 ALOGPS logp 1.65 ChemAxon pka_strongest_basic -7 ChemAxon iupac benzyl acetate ChemAxon average_mass 150.17 ChemAxon mono_mass 150.0681 ChemAxon smiles CC(=O)OCC1=CC=CC=C1 ChemAxon formula C9H10O2 ChemAxon inchi InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3 ChemAxon inchikey QUKGYYKBILRGFE-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 42.03 ChemAxon polarizability 16.03 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003367 13850405 8785 C15513 52051 J0Z CPD-6501 C00035535 Benzyl acetate Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:23:15 UTC 2020-09-11 20:08:57 UTC CDB000059 Histidine Histidine, or l-histidine, abbreviated His or H, an alpha-amino acid, is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3. Histidine is an essential amino acid that is not synthesized de novo in humans and must be obtained though ingestion of histidine. L-Histidine is a strong basic compound. It is an odorless white crystalline powder with a bitter taste. In humans, L-histidine is involved in methylhistidine metabolism. Histidine biosynthesis has been well studied in E. coli and involves eight gene products (His1, 2, 3, 4, 5, 6, 7, and 8, from a single gene) and occurs in ten steps. This is possible because a single gene product can catalyze more than one reaction (PMID:8852895). L-Histidine is found in high concentrations in beluga whales, caseins, and bearded seals and in lower concentration in prairie turnips, puddings, and black walnuts. L-Histidine has also been detected in climbing beans, sago palms, vanilla, pitanga (cherry) and allspices making histidine a potential biomarker for the consumption of these foods. Histidine is an amino acid found in cannabis plants (PMID: 6991645). It is a favouring ingredient and dietary supplement. Histidine was shown to have anti-hypertensive effects, decreasing blood pressure, by modulating the histamine H3 receptor (PMID: 19566844). Histidine is a precursor of histamine, an inflammatory product associated with allergies ( https://doi.org/10.1016/B978-0-12-801238-3.66093-2). Histidine can be post-translationally modified to¬†3-methylhistidine, which is excreted in urine and is a¬†biomarker¬†of skeletal muscle damage (PMID: 16079625). (S)-4-(2-Amino-2-carboxyethyl)imidazole (S)-alpha-Amino-1H-imidazole-4-propanoic acid (S)-alpha-Amino-1H-imidazole-4-propionic acid H His HISTIDINE L-(-)-Histidine L-Histidin (S)-a-Amino-1H-imidazole-4-propanoate (S)-a-Amino-1H-imidazole-4-propanoic acid (S)-alpha-Amino-1H-imidazole-4-propanoate (S)-Α-amino-1H-imidazole-4-propanoate (S)-Α-amino-1H-imidazole-4-propanoic acid (S)-a-Amino-1H-imidazole-4-propionate (S)-a-Amino-1H-imidazole-4-propionic acid (S)-alpha-Amino-1H-imidazole-4-propionate (S)-Α-amino-1H-imidazole-4-propionate (S)-Α-amino-1H-imidazole-4-propionic acid (S)-1H-Imidazole-4-alanine (S)-2-Amino-3-(4-imidazolyl)propionsaeure (S)-Histidine (S)1H-Imidazole-4-alanine 3-(1H-Imidazol-4-yl)-L-alanine Amino-1H-imidazole-4-propanoate Amino-1H-imidazole-4-propanoic acid Amino-4-imidazoleproprionate Amino-4-imidazoleproprionic acid Glyoxaline-5-alanine Histidine, L isomer Histidine, L-isomer L-Isomer histidine L-Histidine C6H9N3O2 155.15 155.0695 (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid L-histidine 30641-68-0 N[C@@H](CC1=CN=CN1)C(O)=O InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1 HNDVDQJCIGZPNO-YFKPBYRVSA-N belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Histidine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteromonocyclic compounds Amino acids Aralkylamines Azacyclic compounds Carbonyl compounds Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Imidazolyl carboxylic acids and derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Alpha-amino acid Amine Amino acid Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Carbonyl group Carboxylic acid Heteroaromatic compound Histidine or derivatives Hydrocarbon derivative Imidazole Imidazolyl carboxylic acid derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Common amino acids L-alpha-amino acid histidine proteinogenic amino acid water_solubility 45.6 mg/mL logp -3.32 CHMELIK,J ET AL. (1991) melting_point 287 °C logp -2.67 ALOGPS logs -0.34 ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 1.85 ChemAxon pka_strongest_basic 9.44 ChemAxon iupac (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid ChemAxon average_mass 155.15 ChemAxon mono_mass 155.0695 ChemAxon smiles N[C@@H](CC1=CN=CN1)C(O)=O ChemAxon formula C6H9N3O2 ChemAxon inchi InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1 ChemAxon inchikey HNDVDQJCIGZPNO-YFKPBYRVSA-N ChemAxon polar_surface_area 92 ChemAxon refractivity 38.06 ChemAxon polarizability 14.67 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00135 DB00117 FDB011856 6038 6274 15971 HIS C00001363 33985 L-histidine 21 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Alifano P, Fani R, Lio P, Lazcano A, Bazzicalupo M, Carlomagno MS, Bruni CB: Histidine biosynthetic pathway and genes: structure, regulation, and evolution. Microbiol Rev. 1996 Mar;60(1):44-69. 8852895 Toba H, Nakamori A, Tanaka Y, Yukiya R, Tatsuoka K, Narutaki M, Tokitaka M, Hariu H, Kobara M, Nakata T: Oral L-histidine exerts antihypertensive effects via central histamine H3 receptors and decreases nitric oxide content in the rostral ventrolateral medulla in spontaneously hypertensive rats. Clin Exp Pharmacol Physiol. 2010 Jan;37(1):62-8. doi: 10.1111/j.1440-1681.2009.05227.x. 19566844 Chinkes DL: Methods for measuring tissue protein breakdown rate in vivo. Curr Opin Clin Nutr Metab Care. 2005 Sep;8(5):534-7. doi: 10.1097/01.mco.0000170754.25372.37. 16079625 1.0 2020-03-18 23:23:18 UTC 2020-09-11 20:08:57 UTC CDB000060 Methionine Methionine, l-methionine abbreviated Met or M, is one of 9 essential amino acids (meaning the body cannot synthesize it; it must be obtained from the diet) required for protein synthesis and for normal growth and development of humans, other mammals, and avian species. It is a white crystalline powder with a mild acidic and sulfurous taste. It is an intermediate in transmethylation reactions, serving as the major methyl group donor for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine where the sulfur atom from methionine is transferred to cysteine (PMID: 16702340). Methionine is an amino acid found in cannabis plants (PMID: 6991645). Methionine is one of 4 sulfur amino acids (SAA) that also include cysteine, taurine and homocysteine (with the latter two not incorporated into proteins). The WHO recommends that healthy adults consume 13 mg/kg per 24 h of normal SAA and roughly double this amount in artificial nutrition regimens. However, in disease or after trauma, SAA requirements may vary. SAA supplementation exceeding 2-3 times the minimum recommended daily intake can be considered safe except in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function where hypermethioninemia or hyperhomocysteinemia may occur. Apart from acetaminophen poisoning, the usefulness of SAA supplementation is not yet established (PMID: 16702341). When present in high levels, methionine can act as an atherogen which is a compound that causes atherosclerosis and cardiovascular disease. Methionine is a precursor of homocysteine. Acute doses of methionine can lead to acute increases in plasma homocysteine, which has been used as an indicator of susceptibility to cardiovascular disease. Longer-term studies in adults have indicated that methionine intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. Rodents fed high levels of methionine developed atherosclerotic plaques independently of homocysteine levels (PMID: 26647293). A similar study in Finnish men showed that high dietary methionine increased the risk of acute coronary events in middle-aged men (PMID: 16487911). These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346). Methionine is also a metabotoxin, which is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency (PMID: 16702350). Chronically elevated levels of methionine in infants can lead to intellectual disability and other neurological problems, delays in motor skills, sluggishness, muscle weakness, and liver problems. Many individuals with these metabolic disorders tend to develop cardiovascular disease later in life. Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, with no effects on healthy subjects. (2R)-2-Amino-4-(methylsulfanyl)butanoic acid (R)-2-Amino-4-(methylthio)butanoic acid (R)-Methionine D-2-Amino-4-(methylthio)butyric acid D-Methionin MED (2R)-2-Amino-4-(methylsulfanyl)butanoate (2R)-2-Amino-4-(methylsulphanyl)butanoate (2R)-2-Amino-4-(methylsulphanyl)butanoic acid (R)-2-Amino-4-(methylthio)butanoate D-2-Amino-4-(methylthio)butyrate L-Isomer methionine L-Methionine Pedameth Liquimeth Methionine, L isomer Methionine, L-isomer Methionine C5H11NO2S 149.21 149.051 (2R)-2-amino-4-(methylsulfanyl)butanoic acid D-methionine 348-67-4 CSCC[C@@H](N)C(O)=O InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1 FFEARJCKVFRZRR-SCSAIBSYSA-N belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Methionine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids D-alpha-amino acids Dialkylthioethers Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Sulfenyl compounds Thia fatty acids Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid D-alpha-amino acid Dialkylthioether Fatty acid Fatty acyl Hydrocarbon derivative Methionine or derivatives Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Sulfenyl compound Thia fatty acid Thioether D-alpha-amino acid Other amino acids methionine melting_point 281 °C Wikipedia logp -1.85 ALOGPS logs -0.80 ALOGPS logp -2.2 ChemAxon pka_strongest_acidic 2.53 ChemAxon pka_strongest_basic 9.5 ChemAxon iupac (2R)-2-amino-4-(methylsulfanyl)butanoic acid ChemAxon average_mass 149.21 ChemAxon mono_mass 149.051 ChemAxon smiles CSCC[C@@H](N)C(O)=O ChemAxon formula C5H11NO2S ChemAxon inchi InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1 ChemAxon inchikey FFEARJCKVFRZRR-SCSAIBSYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 37.59 ChemAxon polarizability 15.46 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00855 DB02893 16867 84815 CPD-218 Methionine Ball RO, Courtney-Martin G, Pencharz PB: The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans. J Nutr. 2006 Jun;136(6 Suppl):1682S-1693S. doi: 10.1093/jn/136.6.1682S. 16702340 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 van de Poll MC, Dejong CH, Soeters PB: Adequate range for sulfur-containing amino acids and biomarkers for their excess: lessons from enteral and parenteral nutrition. J Nutr. 2006 Jun;136(6 Suppl):1694S-1700S. doi: 10.1093/jn/136.6.1694S. 16702341 Selhub J, Troen AM: Sulfur amino acids and atherosclerosis: a role for excess dietary methionine. Ann N Y Acad Sci. 2016 Jan;1363:18-25. doi: 10.1111/nyas.12962. Epub 2015 Dec 8. 26647293 Virtanen JK, Voutilainen S, Rissanen TH, Happonen P, Mursu J, Laukkanen JA, Poulsen H, Lakka TA, Salonen JT: High dietary methionine intake increases the risk of acute coronary events in middle-aged men. Nutr Metab Cardiovasc Dis. 2006 Mar;16(2):113-20. doi: 10.1016/j.numecd.2005.05.005. Epub 2005 Nov 2. 16487911 Garlick PJ: Toxicity of methionine in humans. J Nutr. 2006 Jun;136(6 Suppl):1722S-1725S. doi: 10.1093/jn/136.6.1722S. 16702346 Finkelstein JD: Inborn errors of sulfur-containing amino acid metabolism. J Nutr. 2006 Jun;136(6 Suppl):1750S-1754S. doi: 10.1093/jn/136.6.1750S. 16702350 1.0 2020-03-18 23:23:20 UTC 2020-09-11 20:08:57 UTC CDB000061 Tryptophan Tryptophan, (¬±)-Tryptophan or L-tryptophan abbreviated Trp or W, an aromatic amino acid, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. It is an essential amino acid (meaning the body cannot synthesize it; it must be obtained from the diet) that is necessary for normal growth in infants and for nitrogen balance in adults. Tryptophan is a strong basic compound. It is a pale yellow to yellow crystalline powder. Tryptophan is found in highest concentrations in red bell peppers, caseins, and dried milks and in a lower concentrations in remoulades, clawed lobsters, and garden cress. (¬±)-Tryptophan has also been detected in snack foods, common lings, rapes, bamboo shoots, and other fish products making (¬±)-tryptophan a potential biomarker for the consumption of these foods. The minimum daily requirement for tryptophan for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ, 300 mg of tryptophan a cup of low-fat cottage cheese and up to 600 mg of tryptophan per pound in chicken and turkey (http://www. dcnutrition. com). It is an amino acid found in cannabis plants (PMID:6991645). Plants and microorganisms commonly synthesize tryptophan from shikimic acid or anthranilate. In the latter pathway, phosphoribosylphospho transferase condenses anthranilate with phosphoribosylpyrophosphate (PRPP), generating pyrophosphate and phosphoribosyl anthranilate. Phosphoribosyl anthranilate isomerase isomerizes phosphoribosyl anthranilate into carboyxphenylamino-deoxyribulose 5-phosphate which is then subjected to reductive decarboxylation by indole glycerol synthase, producing indole-3-glycerol phosphate; this, in turn, is transformed into indole. In the last step, tryptophan synthase catalyzes the formation of tryptophan from indole and the amino acid serine (PMID:7640526). Tryptophan is used as nutrient supplement and as an active ingredient in pharmaceutical products. It is a precursor of indole alkaloids and auxins (phytohormones; PMID: 18394986) in plants, In mammals, tryptophan is a precursor of serotonin (a neurotransmitter, a platelet clotting factor, and a neurohormone found in organs throughout the body; PMID: 26560523), melatonin (a neurohormone produced by the pineal gland in animals, which regulates sleep and wakefulness; PMID: 4391290) and niacin (also known as Vitamin B3, synthesized via¬†kynurenine¬†and quinolinic acids, which are products of tryptophan degradation; PMID: 14284754). Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into¬†serotonin¬†and the resulting¬†serotonin¬†is further metabolized into¬†melatonin¬†which promotes sleepiness. There are a few conditions or diseases that are characterized tryptophan deficiencies. For instance,¬†fructose¬†malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn or other tryptophan-deficient diets can cause pellagra, which is a¬†niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia (PMID: 16207585). Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's disease. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as¬†kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids¬†lysine,¬†hydroxylysine, and tryptophan. Babies with GA I are often born with unusually large heads (macrocephaly). Affected individuals may also have difficulty moving and may experience spasms, jerking, rigidity or decreased muscle tone, and muscle weakness. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: 1763543). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: 10721094). This pathological damage is further augmented by metabolites of the¬†kynurenine¬†pathway (a tryptophan degradation pathway).¬† (2R)-2-Amino-3-(1H-indol-3-yl)propanoic acid (R)-Tryptophan DTR (2R)-2-Amino-3-(1H-indol-3-yl)propanoate (+)-Tryptophan (R)-(+)-2-Amino-3-(3-indolyl)propionic acid (R)-2-Amino-3-(3-indolyl)propionic acid D-(+)-Tryptophan D-alpha-Amino-3-indolepropionic acid D-Tryptophane D-Trytophane delta-(+)-Tryptophan delta-alpha-Amino-3-indolepropionic acid delta-Tryptophane delta-Trytophane DL-Tryptophan H-D-TRP-OH H-delta-TRP-OH Tryptophan C11H12N2O2 204.23 204.0899 (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid D-tryptophan 153-94-6 N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1 QIVBCDIJIAJPQS-SECBINFHSA-N belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indolyl carboxylic acids and derivatives Organic compounds Organoheterocyclic compounds Indoles and derivatives Indolyl carboxylic acids and derivatives Aromatic heteropolycyclic compounds 3-alkylindoles Amino acids Aralkylamines Azacyclic compounds Benzenoids Carbonyl compounds Carboxylic acids D-alpha-amino acids Heteroaromatic compounds Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Substituted pyrroles 3-alkylindole Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative D-alpha-amino acid Heteroaromatic compound Hydrocarbon derivative Indole Indolyl carboxylic acid derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Pyrrole Substituted pyrrole D-alpha-amino acid Other amino acids tryptophan water_solubility 11.4 g/L at 25 °C Wikipedia melting_point 282 - 85 °C logp -1.10 ALOGPS logs -2.18 ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 2.54 ChemAxon pka_strongest_basic 9.4 ChemAxon iupac (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid ChemAxon average_mass 204.23 ChemAxon mono_mass 204.0899 ChemAxon smiles N[C@H](CC1=CNC2=CC=CC=C12)C(O)=O ChemAxon formula C11H12N2O2 ChemAxon inchi InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1 ChemAxon inchikey QIVBCDIJIAJPQS-SECBINFHSA-N ChemAxon polar_surface_area 79.11 ChemAxon refractivity 56.2 ChemAxon polarizability 21.17 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB03225 8707 9060 C00525 FDB029595 16296 D-TRYPTOPHAN Tryptophan Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Radwanski ER, Last RL: Tryptophan biosynthesis and metabolism: biochemical and molecular genetics. Plant Cell. 1995 Jul;7(7):921-34. doi: 10.1105/tpc.7.7.921. 7640526 Palme K, Nagy F: A new gene for auxin synthesis. Cell. 2008 Apr 4;133(1):31-2. doi: 10.1016/j.cell.2008.03.014. 18394986 Strasser B, Gostner JM, Fuchs D: Mood, food, and cognition: role of tryptophan and serotonin. Curr Opin Clin Nutr Metab Care. 2016 Jan;19(1):55-61. doi: 10.1097/MCO.0000000000000237. 26560523 Wurtman RJ, Anton-Tay F: The mammalian pineal as a neuroendocrine transducer. Recent Prog Horm Res. 1969;25:493-522. doi: 10.1016/b978-0-12-571125-8.50014-4. 4391290 IKEDA M, TSUJI H, NAKAMURA S, ICHIYAMA A, NISHIZUKA Y, HAYAISHI O: STUDIES ON THE BIOSYNTHESIS OF NICOTINAMIDE ADENINE DINUCLEOTIDE. II. A ROLE OF PICOLINIC CARBOXYLASE IN THE BIOSYNTHESIS OF NICOTINAMIDE ADENINE DINUCLEOTIDE FROM TRYPTOPHAN IN MAMMALS. J Biol Chem. 1965 Mar;240:1395-401. 14284754 Pitche PT: [Pellagra]. Sante. 2005 Jul-Sep;15(3):205-8. 16207585 Milburn DS, Myers CW: Tryptophan toxicity: a pharmacoepidemiologic review of eosinophilia-myalgia syndrome. DICP. 1991 Nov;25(11):1259-62. doi: 10.1177/106002809102501116. 1763543 Gross B, Ronen N, Honigman S, Livne E: Tryptophan toxicity--time and dose response in rats. Adv Exp Med Biol. 1999;467:507-16. 10721094 1.0 2020-03-18 23:23:22 UTC 2020-08-04 22:24:26 UTC CDB000062 Campesterol Campesterol belongs to the class of organic compounds known as ergosterols which are steroids containing ergosta-5,7,22-trien-3beta-ol on the 3-beta-hydroxylated ergostane skeleton. Thus, campesterol is a sterol lipid which is very hydrophobic, practically insoluble in water, and relatively neutral. Campesterol is a phytosterol, meaning it is a steroid derived from plants. Campesterol is found in highest concentrations in canola, corn and rapeseed and in a lower concentrations in banana, pomegranate, pepper, coffee, grapefruit, cucumber, onion, oat, potato, and lemon grass, making campesterol a potential biomarker for the consumption of these foods. Campesterol is also found in cannabis plants (PMID:6991645). As a food additive, phytosterols have cholesterol-lowering properties, by reducing cholesterol absorption in intestines. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols. These products are marketed towards people with high cholesterol, wanting to lower it though diet. and may act in cancer prevention. Phytosterols occur in small amounts in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols reduced cholesterol in human subjects by up to 15% (PMID: 12911045) by inhibiting the incorporation of cholesterol into micelles in the gastrointestinal tract, decreasing the overall amount of cholesterol absorbed. This helps to control the body‚Äôs total cholesterol levels, as well as modify HDL, LDL and TAG levels. It is also thought that phytosterols may contribute to the Transintestinal Cholesterol Excretion (TICE) pathway and may alter the conversion of bile acids into secondary bile acids, all pathways reducing cholesterol levels (PMID: 31438826). C28H48O 400.69 400.3705 (1R,2R,5S,10S,11R,14S,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol (1R,2R,5S,10S,11R,14S,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol 474-62-4 CC(C)[C@H](C)CC[C@@H](C)[C@@H]1CC[C@@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20-,22+,23+,24+,25-,26-,27+,28-/m1/s1 SGNBVLSWZMBQTH-NHCUBAMHSA-N logp 6.81 ALOGPS logs -7.26 ALOGPS logp 7.4 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1R,2R,5S,10S,11R,14S,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol ChemAxon average_mass 400.69 ChemAxon mono_mass 400.3705 ChemAxon smiles CC(C)[C@H](C)CC[C@@H](C)[C@@H]1CC[C@@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C ChemAxon formula C28H48O ChemAxon inchi InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20-,22+,23+,24+,25-,26-,27+,28-/m1/s1 ChemAxon inchikey SGNBVLSWZMBQTH-NHCUBAMHSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 125.17 ChemAxon polarizability 50.98 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Katan MB, Grundy SM, Jones P, Law M, Miettinen T, Paoletti R: Efficacy and safety of plant stanols and sterols in the management of blood cholesterol levels. Mayo Clin Proc. 2003 Aug;78(8):965-78. doi: 10.4065/78.8.965. 12911045 Cedo L, Farras M, Lee-Rueckert M, Escola-Gil JC: Molecular Insights into the Mechanisms Underlying the Cholesterol- Lowering Effects of Phytosterols. Curr Med Chem. 2019;26(37):6704-6723. doi: 10.2174/0929867326666190822154701. 31438826 1.0 2020-03-18 23:23:25 UTC 2020-09-11 20:08:29 UTC CDB000063 alpha-Copaene Alpha-copaene is formally classified as a homocyclic organic compound although it is biochemically a sesquiterpenoid synthesized from isoprene units. Alpha-copaene is an oily liquid hydrocarbon that is found in a number of essential oil-producing plants and whose name is derived from the¬†resin-producing tropical¬†copaiba¬†tree. Alpha-copaene was detected in the essential oils from the inner bark of the plant Kielmeyera coriacea Mart. & Zucc. (PMID: 25960759), the bark from Annona reticulate (PMID: 22007723) and was found in the leaves of Cedrelopsis grevei (PMID: 23459148), and Xylopia laevigata (PMID: 23307235). It is found in traces amount in cannabis plants (PMID: 6991645). Alpha-copaene is a colorless clear viscous liquid with a spicy and woody taste. It that can be found in several food items such as lime, mandarin orange (clementine, tangerine), safflower, and summer savoury, which makes alpha-copaene a potential biomarker for the consumption of these food products. Copaene has been found to increase the antioxidant capacity in human lymphocytes in vitro (PMID: 24287609). 1-(Phenylamino)-8-naphthalenesulfonic acid 1-ANILINO-8-naphthalene sulfonATE 1-Anilino-8-naphthalenesulfonate 1-Anilino-8-naphthalenesulfonic acid 8-Anilino-1-naphthalene sulfonic acid 8-Anilinonaphthalene-1-sulphonic acid ANS 1-(Phenylamino)-8-naphthalenesulfonate 1-(Phenylamino)-8-naphthalenesulphonate 1-(Phenylamino)-8-naphthalenesulphonic acid 1-ANILINO-8-naphthalene sulfonic acid 1-ANILINO-8-naphthalene sulphonate 1-ANILINO-8-naphthalene sulphonic acid 1-Anilino-8-naphthalenesulphonate 1-Anilino-8-naphthalenesulphonic acid 8-Anilino-1-naphthalene sulphonate 8-Anilino-1-naphthalene sulphonic acid 8-Anilinonaphthalene-1-sulfonate 8-Anilinonaphthalene-1-sulfonic acid 8-Anilinonaphthalene-1-sulphonate 1-Anilino-8-naphthalenesulfonate, monoammonium salt, hemihydrate 1-Anilino-8-naphthalenesulfonate, monosodium salt 1-Anilinonaphthalene-8-sulfonic acid 1-Anilino-8-naphthalenesulfonate, magnesium (2:1) 1,8-ANS 1-Anilino-8-naphthalenesulfonate, 3H-labeled 1-Anilino-8-naphthalenesulfonate, ion(1-) 1-Anilino-8-naphthalenesulfonate, monoammonium salt (1S,6S,7S,8S)-8-Isopropyl-1,3-dimethyltricyclo[4.4.0.0(2,7)]dec-3-ene 8-Isopropyl-1,3-dimethyltricyclo(4.4.0.02,7)dec-3-ene Copaene a-Copaene α-copaene C15H24 204.36 204.1878 (1S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene (1S,6S,7S,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene 3856-25-5 CC(C)[C@@H]1CC[C@@]2(C)[C@H]3CC=C(C)C2[C@@H]13 InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14?,15-/m0/s1 VLXDPFLIRFYIME-XIQJJJERSA-N belongs to the class of organic compounds known as 1-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. 1-naphthalene sulfonates Organic compounds Benzenoids Naphthalenes Naphthalene sulfonic acids and derivatives Aromatic homopolycyclic compounds 1-naphthalene sulfonic acids and derivatives 1-sulfo,2-unsubstituted aromatic compounds Aniline and substituted anilines Hydrocarbon derivatives Organic oxides Organopnictogen compounds Organosulfonic acids Secondary amines Sulfonyls 1-naphthalene sulfonate 1-naphthalene sulfonic acid or derivatives 1-sulfo,2-unsubstituted aromatic compound Amine Aniline or substituted anilines Aromatic homopolycyclic compound Arylsulfonic acid or derivatives Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfonic acid or derivatives Organonitrogen compound Organopnictogen compound Organosulfonic acid Organosulfonic acid or derivatives Organosulfur compound Secondary amine Sulfonyl aminonaphthalene naphthalenesulfonic acid logp 3.75 ALOGPS logs -5.05 ALOGPS logp 4.09 ChemAxon iupac (1S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@@H]1CC[C@@]2(C)[C@H]3CC=C(C)C2[C@@H]13 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14?,15-/m0/s1 ChemAxon inchikey VLXDPFLIRFYIME-XIQJJJERSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.77 ChemAxon polarizability 16.34 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1369 DB04474 39708 C11326 8-Anilinonaphthalene-1-sulfonic_acid Martins Cde M, do Nascimento EA, de Morais SA, de Oliveira A, Chang R, Cunha LC, Martins MM, Martins CH, Moraes Tda S, Rodrigues PV, da Silva CV, de Aquino FJ: Chemical Constituents and Evaluation of Antimicrobial and Cytotoxic Activities of Kielmeyera coriacea Mart. & Zucc. Essential Oils. Evid Based Complement Alternat Med. 2015;2015:842047. doi: 10.1155/2015/842047. Epub 2015 Apr 16. 25960759 Afoulous S, Ferhout H, Raoelison EG, Valentin A, Moukarzel B, Couderc F, Bouajila J: Chemical composition and anticancer, antiinflammatory, antioxidant and antimalarial activities of leaves essential oil of Cedrelopsis grevei. Food Chem Toxicol. 2013 Jun;56:352-62. doi: 10.1016/j.fct.2013.02.008. Epub 2013 Feb 28. 23459148 Quintans Jde S, Soares BM, Ferraz RP, Oliveira AC, da Silva TB, Menezes LR, Sampaio MF, Prata AP, Moraes MO, Pessoa C, Antoniolli AR, Costa EV, Bezerra DP: Chemical constituents and anticancer effects of the essential oil from leaves of Xylopia laevigata. Planta Med. 2013 Jan;79(2):123-30. doi: 10.1055/s-0032-1328091. Epub 2013 Jan 10. 23307235 Chavan MJ, Wakte PS, Shinde DB: Analgesic and anti-inflammatory activities of the sesquiterpene fraction from Annona reticulata L. bark. Nat Prod Res. 2012;26(16):1515-8. doi: 10.1080/14786419.2011.564583. Epub 2011 Oct 19. 22007723 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Turkez H, Celik K, Togar B: Effects of copaene, a tricyclic sesquiterpene, on human lymphocytes cells in vitro. Cytotechnology. 2014 Aug;66(4):597-603. doi: 10.1007/s10616-013-9611-1. Epub 2013 Nov 28. 24287609 1.0 2020-03-18 23:23:27 UTC 2020-08-04 22:24:27 UTC CDB000064 Dihydroresveratrol Dihydroresveratrol or 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol is a stilbenol where hydroxy groups at positions 1, 3 and 4' are added to 1,1'-ethane-1,2-diyldibenzene. Dihydroresveratrol is an aromatic polyketide, which contains alternating carbonyl groups and methylene groups. Dihydroresveratrol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Dihydroresveratrol is a non-cannabinoid estrogenic compound found in cannabis (PMID: 6991645). Dihydroresveratrol, a prominent polyphenol component of red wine (PMID: 20630177), has a profound proliferative effect on hormone-sensitive tumor cell lines at picomolar concentrations. Dihydroresveratol is a derivative of resveratol and one of the main metabolites of two stereoisomers of resveratol, trans resveratrol and cis resveratrol. Dihydroresveratrol is formed in the intestine by microbial hydrogenation of trans-resveratrol (PMID: 20509689). Trans-resveratrol is a common component of fruits and berries, particularly grapes (Vitis vinifera), where it is formed as a response to the stress of weather conditions, microbe infections, or direct sunlight. Cis resveratrol is as a minor component in some berries, grapes, and wines along with trans-resveratrol (PMID: 20813524). Resveratrol has received special attention due to its diverse and potentially beneficial biological properties. The compound is currently on the market as a popular dietary supplement and is under clinical trials for treatment of some types of cancers (PMID: 25446990), metabolic syndrome, Alzheimer‚Äôs disease, type 2 diabetes, obesity (PMID: 25790328), neurologic syndrome, and some symptoms of aging. 3,4',5-Trihydroxybibenzyl Dihydro-resveratrol C14H14O3 230.26 230.0943 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol dihydroresveratrol OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2 HITJFUSPLYBJPE-UHFFFAOYSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Hydrocarbon derivatives Organooxygen compounds Resorcinols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Resorcinol Stilbene Bibenzyls Diphenyl ethers, biphenyls, dibenzyls and stilbenes Diphenyl ethers, biphenyls, dibenzyls and stilbenes stilbenol logp 2.45 ALOGPS logs -3.45 ALOGPS logp 3.6 ChemAxon pka_strongest_acidic 9.3 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol ChemAxon average_mass 230.26 ChemAxon mono_mass 230.0943 ChemAxon smiles OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 ChemAxon formula C14H14O3 ChemAxon inchi InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2 ChemAxon inchikey HITJFUSPLYBJPE-UHFFFAOYSA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 66.34 ChemAxon polarizability 24.87 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB029989 185914 4582 DB08466 C10255 C00002879 Dihydro-resveratrol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Montes R, Garcia-Lopez M, Rodriguez I, Cela R: Mixed-mode solid-phase extraction followed by acetylation and gas chromatography mass spectrometry for the reliable determination of trans-resveratrol in wine samples. Anal Chim Acta. 2010 Jul 12;673(1):47-53. doi: 10.1016/j.aca.2010.05.021. Epub 2010 Jun 4. 20630177 Gakh AA, Anisimova NY, Kiselevsky MV, Sadovnikov SV, Stankov IN, Yudin MV, Rufanov KA, Krasavin MY, Sosnov AV: Dihydro-resveratrol--a potent dietary polyphenol. Bioorg Med Chem Lett. 2010 Oct 15;20(20):6149-51. doi: 10.1016/j.bmcl.2010.08.002. Epub 2010 Aug 5. 20813524 Juan ME, Alfaras I, Planas JM: Determination of dihydroresveratrol in rat plasma by HPLC. J Agric Food Chem. 2010 Jun 23;58(12):7472-5. doi: 10.1021/jf100836j. 20509689 Singh CK, Ndiaye MA, Ahmad N: Resveratrol and cancer: Challenges for clinical translation. Biochim Biophys Acta. 2015 Jun;1852(6):1178-85. doi: 10.1016/j.bbadis.2014.11.004. Epub 2014 Nov 8. 25446990 van der Made SM, Plat J, Mensink RP: Resveratrol does not influence metabolic risk markers related to cardiovascular health in overweight and slightly obese subjects: a randomized, placebo-controlled crossover trial. PLoS One. 2015 Mar 19;10(3):e0118393. doi: 10.1371/journal.pone.0118393. eCollection 2015. 25790328 1.0 2020-03-18 23:23:29 UTC 2020-07-07 15:54:51 UTC CDB000065 Hexyl acetate Hexyl acetate, also known as N-hexyl ethanoate or hexyl acetic acid, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Hexyl acetate is a very hydrophobic molecule, practically insoluble in water, very soluble in alcohols and relatively neutral. It is a naturally occurring organic compound found in many fruits such as apples and plums. Hexyl acetate is a sweet, apple, and banana tasting compound and has a fruity odor. Hexyl acetate is found in the highest concentrations in highbush blueberries and has been detected in alcoholic beverages, pears, oats, roman camomiles, and sweet cherries making it a potential biomarker for the consumption of these foods. Hexyl acetate is one of the simple esters that have been identified in cannabis plant (PMID: 6991645). Hexyl acetate is mainly used as a solvent for resins, polymers, fats and oils and as a paint additive to improve its dispersion on a surface ( https://doi.org/10.1002/14356007.a24_437). N-Hexyl ethanoate N-Hexyl ethanoic acid Hexyl acetic acid 1-Hexyl acetate 1-Octanamine, hydrochloride Acetate C6 Acetic acid N-hexyl ester Acetic acid, hexyl ester FEMA 2565 Hexyl alcohol, acetate Hexyl ester OF acetic acid Hexyl ethanoate Methylamyl acetate N-Hexyl acetate C8H16O2 144.21 144.115 hexyl acetate hexyl acetate 142-92-7 CCCCCCOC(C)=O InChI=1S/C8H16O2/c1-3-4-5-6-7-10-8(2)9/h3-7H2,1-2H3 AOGQPLXWSUTHQB-UHFFFAOYSA-N belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Carboxylic acid esters Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters acetate ester water_solubility 0.511 mg/mL at 25 °C melting_point -81 °C boiling_point 155–156 °C Wikipedia logp 3.02 ALOGPS logs -2.50 ALOGPS logp 2.14 ChemAxon pka_strongest_basic -7 ChemAxon iupac hexyl acetate ChemAxon average_mass 144.21 ChemAxon mono_mass 144.115 ChemAxon smiles CCCCCCOC(C)=O ChemAxon formula C8H16O2 ChemAxon inchi InChI=1S/C8H16O2/c1-3-4-5-6-7-10-8(2)9/h3-7H2,1-2H3 ChemAxon inchikey AOGQPLXWSUTHQB-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 40.49 ChemAxon polarizability 17.57 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001267 8568 8908 87510 C00035701 Hexyl_acetate Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:23:31 UTC 2020-08-04 22:24:28 UTC CDB000066 Pinocarveol Pinocarveol, also known as 2(10)-pinen-3-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing 2 rings, fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. Thus, pinocarveol is an isoprenoid lipid molecule. Pinocarveol is very hydrophobic, practically insoluble in water and relatively neutral. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 23746261). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pinocarveol is a clear viscous liquid with a balsam, camphor, and herbal taste. Pinocarveol is found, in highest concentrations in hyssops and rosemaries and has been detected in spearmints, sweet bay, wild celeries and cannabis (PMID: 6991645). C10H16O 152.24 152.1201 (1S,3S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol (1S,3S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol 19889-99-7 CC1(C)[C@H]2C[C@@H]1C(=C)[C@@H](O)C2 InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9-/m0/s1 LCYXQUJDODZYIJ-YIZRAAEISA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Pinane monoterpenoid Secondary alcohol logp 2.24 ALOGPS logs -1.94 ALOGPS logp 1.63 ChemAxon pka_strongest_acidic 17.94 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (1S,3S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles CC1(C)[C@H]2C[C@@H]1C(=C)[C@@H](O)C2 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9-/m0/s1 ChemAxon inchikey LCYXQUJDODZYIJ-YIZRAAEISA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.17 ChemAxon polarizability 17.88 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 88297 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:23:33 UTC 2020-08-04 22:24:28 UTC CDB000067 Pinocarvone Pinocarvone or (-)-Pinocarvone, also known as 2(10)-pinen-3-one, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing 2 rings, fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 23746261). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes (PMID: 23911730). GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Thus, (-)-pinocarvone is an isoprenoid lipid molecule. Pinocarvone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Pinocarvone is a volatile, minty tasting compound. Pinocarvone is found in higher concentrations in hyssops. It has also been detected in cauliflowers, spearmints, sweet bay and in cannabis plants (PMID: 6991645). C10H14O 150.22 150.1045 (1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one (1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one 19890-00-7 CC1(C)[C@H]2C[C@@H]1C(=C)C(=O)C2 InChI=1S/C10H14O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-8H,1,4-5H2,2-3H3/t7-,8+/m0/s1 TZDMGBLPGZXHJI-JGVFFNPUSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic ketones Hydrocarbon derivatives Organic oxides Aliphatic homopolycyclic compound Bicyclic monoterpenoid Carbonyl group Cyclic ketone Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Pinane monoterpenoid logp 2.28 ALOGPS logs -2.39 ALOGPS logp 2.19 ChemAxon pka_strongest_basic -5 ChemAxon iupac (1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC1(C)[C@H]2C[C@@H]1C(=C)C(=O)C2 ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-8H,1,4-5H2,2-3H3/t7-,8+/m0/s1 ChemAxon inchikey TZDMGBLPGZXHJI-JGVFFNPUSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 44.34 ChemAxon polarizability 17.26 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12314319 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 Kulkarni R, Pandit S, Chidley H, Nagel R, Schmidt A, Gershenzon J, Pujari K, Giri A, Gupta V: Characterization of three novel isoprenyl diphosphate synthases from the terpenoid rich mango fruit. Plant Physiol Biochem. 2013 Oct;71:121-31. doi: 10.1016/j.plaphy.2013.07.006. Epub 2013 Jul 16. 23911730 1.0 2020-03-18 23:23:35 UTC 2020-08-04 22:24:28 UTC CDB000068 Beta-Ionone Beta-ionone, also known as (e)-b-ionone or trans-beta-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Beta-ionone is a neutral compound. Beta-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil and found in cannabis plants (PMID:6991645). Beta-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Beta-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Beta-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Beta-ionone is used as a food flavoring in beverages,¬†ice¬†cream, baked goods and candies ( https://doi.org/10.1533/9780857095725.1.231). (e)-beta-Ionone beta-e-Ionone beta-Ionon trans-beta-Ionone (e)-b-Ionone (e)-Β-ionone b-e-Ionone Β-e-ionone b-Ionon Β-ionon trans-b-Ionone trans-Β-ionone b-Ionone Β-ionone (3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (3E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one (e)-beta -Ionone 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-(e)-3-buten-2-one beta -e-Ionone FEMA 2595 Ionone, beta trans-beta -Ionone [e]-4-[2,6,6-Trimethyl-1-cyclohexen-1-yl]-3-buten-2-one 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one beta-Ionone, (trans)-isomer C13H20O 192.3 192.1514 (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one β-ionone 79-77-6 CC(=O)\C=C\C1=C(C)CCCC1(C)C InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+ PSQYTAPXSHCGMF-BQYQJAHWSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Acryloyl compounds Enones Hydrocarbon derivatives Ketones Organic oxides Acryloyl-group Aliphatic homomonocyclic compound Alpha,beta-unsaturated ketone Carbonyl group Cyclofarsesane sesquiterpenoid Enone Hydrocarbon derivative Ionone derivative Ketone Megastigmane sesquiterpenoid Organic oxide Organic oxygen compound Organooxygen compound Sesquiterpenoid ionone logp 4.11 ALOGPS logs -3.27 ALOGPS logp 3.28 ChemAxon pka_strongest_acidic 19.71 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one ChemAxon average_mass 192.3 ChemAxon mono_mass 192.1514 ChemAxon smiles CC(=O)\C=C\C1=C(C)CCCC1(C)C ChemAxon formula C13H20O ChemAxon inchi InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+ ChemAxon inchikey PSQYTAPXSHCGMF-BQYQJAHWSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 61.82 ChemAxon polarizability 23.36 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015469 638014 C00029816 553581 C12287 CPD-7204 Ionone ID3 32325 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:23:38 UTC 2020-09-11 20:08:28 UTC CDB000069 Limonene Limonene or dipentene, belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. Para-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Limonene exists as a clear colourless liquid at room temperature. Industrially limonene is used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. Limonene is often marketed as a botanical (plant-derived) solvent of low toxicity. It is a chiral molecule, and biological sources produce only one enantiomer, the D-isomer. Limonene is one of the monoterpenes identified in Cannabis sativa (PMID: 6991645). It is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). D-Limonene is a major component of the aromatic scents and resins characteristic of numerous coniferous and broadleaved trees including red and silver maple, cottonwoods, aspens, spruce, various pines, Douglas fir, larches and cedars. D-Limonene is the major component in oil of oranges. Because of its pleasant odor, limonene is widely used as a flavour and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). As the main fragrance of citrus peels, D-limonene is used in food manufacturing and some medicines, such as a flavoring to mask the bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions, bath products, and other personal care products. Limonene is also used as a botanical insecticide. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization and may have irritative and bronchoconstrictive airway effects. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer (PMID: 16563357, 15499193, 15325315, 2024047 ). (-)-(S)-Limonene (-)-(4S)-Limonene (4S)-1-Methyl-4-isopropenylcyclohex-1-ene (4S)-4-Isopropenyl-1-methylcyclohexene (S)-(-)-p-Mentha-1,8-diene (S)-1-Methyl-4-(1-methylethenyl)cyclohexene (S)-p-Mentha-1,8-diene 4AlphaH-p-mentha-1,8-diene L-Limonen L-Limonene 4-Isopropenyl-1-methyl-1-cyclohexene Limonene (+)-Limonene AISA 5203-L (+)limonene Dipentene 1-Methyl-4-(1-methylethenyl)cyclohexene Limonene, (+-)-isomer (D)-Limonene 4-Mentha-1,8-diene Limonene, (S)-isomer Limonene, (R)-isomer (R)-(+)-Limonene (R)-4-Isopropenyl-1-methylcyclohexene (+)-(R)-4-Isopropenyl-1-methylcyclohexene (4R)-1-Methyl-4-(1-methylethenyl)cyclohexene D-Limonene 4 Mentha 1,8 diene D Limonene (-)-alpha-Limonene (-)-Α-limonene (4S)-1-Methyl-4-(1-methylethenyl)cyclohexene (4S)-Limonene (S)-(-)-Limonene (S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene (S)-4-Isopropenyl-1-methyl-1-cyclohexene (S)-Limonene beta-Limonene L-Carvene Β-limonene (-)-Limonene C10H16 136.23 136.1252 (4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene (-)-limonene 5989-54-8 CC(=C)[C@H]1CCC(C)=CC1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1 XMGQYMWWDOXHJM-SNVBAGLBSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids limonene water_solubility 0.0138 mg/mL at 25 °C logp 4.57 LI,J & PURDUE,EM (1995) melting_point -74.3 °C boiling_point 176 °C Wikipedia logp 4.50 ALOGPS logs -2.47 ALOGPS logp 3.22 ChemAxon iupac (4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(=C)[C@H]1CCC(C)=CC1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1 ChemAxon inchikey XMGQYMWWDOXHJM-SNVBAGLBSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.48 ChemAxon polarizability 17.23 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006329 388386 15383 439250 C00521 C00000803 47361 Limonene 6911 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Flamm WG, Lehman-McKeeman LD: The human relevance of the renal tumor-inducing potential of d-limonene in male rats: implications for risk assessment. Regul Toxicol Pharmacol. 1991 Feb;13(1):70-86. doi: 10.1016/0273-2300(91)90042-t. 2024047 Aggarwal BB, Shishodia S: Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol. 2006 May 14;71(10):1397-421. doi: 10.1016/j.bcp.2006.02.009. Epub 2006 Feb 23. 16563357 Tsuda H, Ohshima Y, Nomoto H, Fujita K, Matsuda E, Iigo M, Takasuka N, Moore MA: Cancer prevention by natural compounds. Drug Metab Pharmacokinet. 2004 Aug;19(4):245-63. doi: 10.2133/dmpk.19.245. 15499193 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 DeWitt C, Bebarta V: Botanical solvents. Clin Occup Environ Med. 2004 Aug;4(3):445-54, v-vi. doi: 10.1016/j.coem.2004.03.003. 15325315 1.0 2020-03-18 23:23:40 UTC 2020-07-24 23:30:05 UTC CDB000070 Fenchone Fenchone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, fenchone is an isoprenoid lipid molecule. Fenchone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Fenchone is a colorless oily liquid with a bitter, camphor, and cedar leaf taste. Fenchone occurs in fennels (https://doi.org/10.1111/j.2042-7158.1968.tb09783.x), rosemaries, and star anises making fenchone a potential biomarker for the consumption of these foods. Fenchone was detected in the fresh bud of the cannabis plant (PMID: 8984153). Fenchone is used as a flavor in foods such as candy and baked goods and to add scents to soaps, detergents, perfumes and lotions. It also an insect repellent. (-)-Fenchone (1R)-(-)-Fenchone (1R)-Fenchone (1R,4S)-(-)-Fenchone (1R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one (R)-(-)-Fenchone (R)-Fenchone L-(-)-Fenchone l-Fenchone 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-one (±)-Fenchone 1,3,3-Trimethyl-2-norbornanone 1,3,3-Trimethylnorcamphor dl-Fenchone C10H16O 152.24 152.1201 (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one fenchone, (+-)- 7787-20-4 CC1(C)[C@H]2CC[C@](C)(C2)C1=O InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1 LHXDLQBQYFFVNW-OIBJUYFYSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Hydrocarbon derivatives Ketones Organic oxides Aliphatic homopolycyclic compound Bicyclic monoterpenoid Carbonyl group Fenchane monoterpenoid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Bicyclic monoterpenoids fenchone melting_point 6.1 °C Wikipedia boiling_point 193.5 °C Wikipedia logp 2.54 ALOGPS logs -2.24 ALOGPS logp 3.06 ChemAxon pka_strongest_basic -7.6 ChemAxon iupac (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles CC1(C)[C@H]2CC[C@](C)(C2)C1=O ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1 ChemAxon inchikey LHXDLQBQYFFVNW-OIBJUYFYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 44.54 ChemAxon polarizability 17.85 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 36612 82229 Ross SA, ElSohly MA: The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J Nat Prod. 1996 Jan;59(1):49-51. doi: 10.1021/np960004a. 8984153 1.0 2020-03-18 23:23:42 UTC 2020-08-04 22:24:29 UTC CDB000071 L-Arabinose Arabinose or L-arabinose is an aldopentose, a monosaccharide with an aldehyde functional group. Although most saccharides have the D-form, arabinose is most abundant in the L-form. It is colorless with a prism or needle like crystal that is very soluble in water. It has a sweet taste. It is one of the most abundant components released after complete hydrolysis of non-starch polysaccharides (NSP) from vegetables. However, NSPs which include cellulose, hemi-cellulose, pectin, and oligosaccharides, are complicated compounds both in physical structure and chemical composition. The NSPs are resistant to the digestive enzymes and pass to the hindgut where microbial degradation takes place. When L-arabinose is ingested, it is absorbed from the intestinal tract at a lower rate than glucose with a portion excreted in the urine. Although widely present in nature, L-arabinose is rarely used, and its physiological effects in vivo have received little attention. L-arabinose selectively inhibits intestinal sucrase activity in a non-competitive manner and suppresses the plasma glucose increase after sucrose ingestion (PMID: 8931641). Because the intestinal absorption of sucrose is inhibited in the presence of L-arabinose, the absorption of sucrose should be reduced by arabinose ingestion. Most of the studies reported so far on the absorption and utilization of L-arabinose have been with non human omnivore animal (PMID:11238761; PMID: 1390604).. In a rare published case, two autistic brothers, with no known metabolic disease, had nearly six times greater L-arabinose(179 ¬µmol/mmol creatinine) in their urine compared to normal children (PMID: 7628083). L-Arabinose was elevated in the CSF and urine of patients with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism (PMID: 14988808). L-Arabinose is also a microbial metabolite found in Mycobacterium (PMID: 16232643). Arabinose is a major monosaccharide sugar found in cannabis plants (PMID: 6991645). (2S,3R,4R)-2,3,4,5-Tetrahydroxypentanal (+/-)-arabinose Aloe sugar Aloinose DL-Arabinose Pectinose D-Arabinose C5H10O5 150.13 150.0528 (2S,3R,4R)-2,3,4,5-tetrahydroxypentanal arabinose 147-81-9 OC[C@@H](O)[C@@H](O)[C@H](O)C=O InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1 PYMYPHUHKUWMLA-WDCZJNDASA-N belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Pentoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha-hydroxyaldehydes Beta-hydroxy aldehydes Hydrocarbon derivatives Organic oxides Polyols Primary alcohols Secondary alcohols Short-chain aldehydes Alcohol Aldehyde Aliphatic acyclic compound Alpha-hydroxyaldehyde Beta-hydroxy aldehyde Carbonyl group Hydrocarbon derivative Organic oxide Pentose monosaccharide Polyol Primary alcohol Secondary alcohol Short-chain aldehyde D-arabinose aldehydo-arabinose water_solubility 834 g/L at 25 °C Wikipedia melting_point 164 - 165 °C Wikipedia logp -2.28 ALOGPS logs 0.40 ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 12.33 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R,4R)-2,3,4,5-tetrahydroxypentanal ChemAxon average_mass 150.13 ChemAxon mono_mass 150.0528 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@H](O)C=O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1 ChemAxon inchikey PYMYPHUHKUWMLA-WDCZJNDASA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 31.38 ChemAxon polarizability 13.42 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001219 59687 66308 46983 Arabinose Seri K, Sanai K, Matsuo N, Kawakubo K, Xue C, Inoue S: L-arabinose selectively inhibits intestinal sucrase in an uncompetitive manner and suppresses glycemic response after sucrose ingestion in animals. Metabolism. 1996 Nov;45(11):1368-74. doi: 10.1016/s0026-0495(96)90117-1. 8931641 Osaki S, Kimura T, Sugimoto T, Hizukuri S, Iritani N: L-arabinose feeding prevents increases due to dietary sucrose in lipogenic enzymes and triacylglycerol levels in rats. J Nutr. 2001 Mar;131(3):796-9. doi: 10.1093/jn/131.3.796. 11238761 Schutte JB, de Jong J, van Weerden EJ, Tamminga S: Nutritional implications of L-arabinose in pigs. Br J Nutr. 1992 Jul;68(1):195-207. doi: 10.1079/bjn19920077. 1390604 Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. 7628083 Ahmed Z, Shimonishi T, Bhuiyan SH, Utamura M, Takada G, Izumori K: Biochemical preparation of L-ribose and L-arabinose from ribitol: a new approach. J Biosci Bioeng. 1999;88(4):444-8. doi: 10.1016/s1389-1723(99)80225-4. 16232643 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. doi: 10.1086/383204. Epub 2004 Feb 25. 14988808 1.0 2020-03-18 23:23:44 UTC 2020-08-04 22:24:29 UTC CDB000072 Heptanal Heptanal, also known as enanthal or N-heptaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, heptanal is a fatty aldehyde lipid molecule. It is an endogenous aldehyde resulting from membrane lipid oxidation. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor with an aldehydic, citrus, and fat taste. It is miscible with alcohols and practically insoluble in water. Heptanal is very hydrophobic and is relatively neutral. Heptanal exists in all eukaryotes, from yeast to humans. It is found in highest concentrations in corns, tea, and sweet oranges and in a lower concentrations in lemons, wild carrots, and carrots. Heptanal was detected in horned melons, common beets, dills, red bell peppers, and malus (crab apple) making it a potential biomarker for the consumption of these foods. Heptanal was distilled from castor oil and first described in 1878 ( https://pubs.rsc.org/en/content/articlelanding/1878/an/an878030329a#!divAbstract). Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus) ( https://www.routledge.com/Fenarolis-Handbook-of-Flavor-Ingredients/Burdock/p/book/9781420090772). ¬†Heptanal is a simple aldehyde found in cannabis plants (PMID: 6991645). Because of heptanal‚Äôs strong fruity odor, it is used as precursor to components in perfumes and lubricants ( https://doi.org/10.1002/14356007.a01_321.pub2). For example, heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%) to alpha-pentylcinnamaldehyde, which is also called jasmine aldehyde (because of the typical jasmine odor). This jasmine aldehyde has been used in fragrances. Heptanal may be a potential biomarker of lung cancer as it was found in the blood of lung cancer patients (PMID:28366212). Aldehyde C-7 Enanthal Enanthaldehyde Enanthic aldehyde Heptaldehyde Heptanaldehyde Heptyl aldehyde Heptylaldehyde N-C6H13CHO N-Heptaldehyde N-Heptanal N-Heptylaldehyde Oenanthal Oenanthaldehyde Oenanthic aldehyde Oenanthol 1-Heptaldehyde 1-Heptanal Aldehyde C7 Enanthole FEMA 2540 Heptan-1-al Oenanthole Heptanal C7H14O 114.19 114.1045 heptanal heptanal 111-71-7 CCCCCCC=O InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3 FXHGMKSSBGDXIY-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide Fatty aldehydes an <i>n</i>-alkanal fatty aldehyde water_solubility 1.25 mg/mL at 25 °C melting_point -43.3 °C boiling_point 152.8 °C Wikipedia logp 2.59 ALOGPS logs -1.93 ALOGPS logp 2.1 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac heptanal ChemAxon average_mass 114.19 ChemAxon mono_mass 114.1045 ChemAxon smiles CCCCCCC=O ChemAxon formula C7H14O ChemAxon inchi InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3 ChemAxon inchikey FXHGMKSSBGDXIY-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 34.75 ChemAxon polarizability 14.4 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008048 C14390 7838 8130 34787 C00034880 Heptanal Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Oenning AL, Mores L, Dias AN, Carasek E: A new configuration for bar adsorptive microextraction (BAmuE) for the quantification of biomarkers (hexanal and heptanal) in human urine by HPLC providing an alternative for early lung cancer diagnosis. Anal Chim Acta. 2017 May 1;965:54-62. doi: 10.1016/j.aca.2017.02.034. Epub 2017 Mar 6. 28366212 1.0 2020-03-18 23:23:46 UTC 2020-08-04 22:24:29 UTC CDB000073 Tridecanal Tridecanal belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain length of at least 12 carbon atoms. Thus, tridecanal is a fatty aldehyde lipid molecule. Tridecanal is a very hydrophobic molecule, practically insoluble in water, soluble in alcohol and relatively neutral. Tridecanal is a colorless clear liquid with a sweet, aldehydic, and citrus taste with a fresh clean aldehydic soapy odor (http://www.thegoodscentscompany.com/data/rw1005541.html). Tridecanal is found in highest concentrations in corianders (PMID: 25776008) and was detected in citrus, corns, evergreen blackberries, cucumbers, and herbs and spices making tridecanal a potential biomarker for the consumption of these foods. Tridecanal is a simple aldehyde found in cannabis plants (PMID: 6991645). 1-Tridecanal N-Tridecanal N-Tridecylaldehyde Tridecanaldehyde Tridecane aldehyde Tridecyl aldehyde C13H26O 198.34 198.1984 tridecanal tridecanal 10486-19-8 CCCCCCCCCCCCC=O InChI=1S/C13H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h13H,2-12H2,1H3 BGEHHAVMRVXCGR-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms. Fatty aldehydes Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty aldehydes Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aldehyde Aliphatic acyclic compound Alpha-hydrogen aldehyde Carbonyl group Fatty aldehyde Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Fatty aldehydes melting_point 14 °C logp 5.88 ALOGPS logs -5.71 ALOGPS logp 4.76 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac tridecanal ChemAxon average_mass 198.34 ChemAxon mono_mass 198.1984 ChemAxon smiles CCCCCCCCCCCCC=O ChemAxon formula C13H26O ChemAxon inchi InChI=1S/C13H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h13H,2-12H2,1H3 ChemAxon inchikey BGEHHAVMRVXCGR-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 62.36 ChemAxon polarizability 27.02 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB002897 25311 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Laribi B, Kouki K, M'Hamdi M, Bettaieb T: Coriander (Coriandrum sativum L.) and its bioactive constituents. Fitoterapia. 2015 Jun;103:9-26. doi: 10.1016/j.fitote.2015.03.012. Epub 2015 Mar 14. 25776008 1.0 2020-03-18 23:23:48 UTC 2020-08-04 22:24:29 UTC CDB000074 Methyl salicylate Methyl salicylate or methyl 2-hydroxybenzoate, belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Methyl 2-hydroxybenzoate, a methyl ester of salicylic acid, is a neutral compound. It is a colorless, viscous liquid with a sweet fruity odor reminiscent of a mint and with a peppermint, and wintergreen taste. It is a naturally occurring organic compound in many species of plants, particularly wintergreens and in cannabis plants (PMID: 6991645). Methyl 2-hydroxybenzoate is found in highest concentrations in hyssops and bilberries and was detected in sour cherries, tamarinds, garden tomato (var.), black elderberries, and mandarin orange (clementine, tangerine). This could make methyl 2-hydroxybenzoate a potential biomarker for the consumption of these foods. It is also present in wines (PMID: 31500198; PMID: 31500198), tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry ( PMID: 31608465), papaya and plum. It is an anti-herbivore used by some plants to recruit beneficial insects (PMID: 15537163). It used as a fragrance and is used in foods such as chewing gum and mints and in beverages. It is a topical analgesic added to liniments (such as Bengay) where it acts as a counter-irritant to relieve joint and muscle pain. As methyl salicyclate is metabolized to salicyclate, it is a potentially toxic compound, particularly to children or to adults who excessive overuse such liniments. 2-(Methoxycarbonyl)phenol 2-Carbomethoxyphenol 2-Hydroxybenzoic acid methyl ester Betula oil Gaultheria oil Methyl O-hydroxybenzoate Natural wintergreen oil Oil OF wintergreen Spicewood oil Sweet birch oil Teaberry oil 2-Hydroxybenzoate methyl ester Methyl O-hydroxybenzoic acid Methyl 2-hydroxybenzoic acid Benzoic acid, 2-hydroxy-, methyl ester FEMA 2745 Methyl ester 2-hydroxy-benzoic acid Methyl salicylate, 8ci O-Hydroxybenzoic acid, methyl ester Methylsalicylate Rheumabal Hewedolor Linsal Metsal liniment Methyl salicylate sodium salt Methyl salicylic acid Methyl ester 2-hydroxy benzoic acid Methyl ester OF 2-hydroxy benzoic acid Methyl salicylate O-Hydroxybenzoic acid methyl ester Methyl 2-hydroxybenzoate C8H8O3 152.15 152.0473 methyl 2-hydroxybenzoate methyl salicylate 119-36-8 COC(=O)C1=CC=CC=C1O InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3 OSWPMRLSEDHDFF-UHFFFAOYSA-N belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. o-Hydroxybenzoic acid esters Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzoyl derivatives Hydrocarbon derivatives Methyl esters Monocarboxylic acids and derivatives Organic oxides Organooxygen compounds Salicylic acid and derivatives Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzoyl Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Methyl ester Monocarboxylic acid or derivatives O-hydroxybenzoic acid ester Organic oxide Organic oxygen compound Organooxygen compound Phenol Salicylic acid or derivatives Vinylogous acid a small molecule benzoate ester salicylates water_solubility 0.7 mg/mL at 30 °C logp 2.55 melting_point -8.6 °C boiling_point 222 °C Wikipedia logp 2.07 ALOGPS logs -1.42 ALOGPS logp 2.32 ChemAxon pka_strongest_acidic 9.72 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac methyl 2-hydroxybenzoate ChemAxon average_mass 152.15 ChemAxon mono_mass 152.0473 ChemAxon smiles COC(=O)C1=CC=CC=C1O ChemAxon formula C8H8O3 ChemAxon inchi InChI=1S/C8H8O3/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5,9H,1H3 ChemAxon inchikey OSWPMRLSEDHDFF-UHFFFAOYSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 40.06 ChemAxon polarizability 14.98 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012459 DB09543 13848808 4133 C12305 31832 C00030767 CPD-6442 Methyl_salicylate Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Carlin S, Masuero D, Guella G, Vrhovsek U, Mattivi F: Methyl Salicylate Glycosides in Some Italian Varietal Wines. Molecules. 2019 Sep 6;24(18). pii: molecules24183260. doi: 10.3390/molecules24183260. 31500198 Yu AN, Yang YN, Yang Y, Zheng FP, Sun BG: Free and bound volatile compounds in the Rubus coreanus fruits of different ripening stages. J Food Biochem. 2019 Oct;43(10):e12964. doi: 10.1111/jfbc.12964. Epub 2019 Jun 26. 31608465 James DG, Price TS: Field-testing of methyl salicylate for recruitment and retention of beneficial insects in grapes and hops. J Chem Ecol. 2004 Aug;30(8):1613-28. doi: 10.1023/b:joec.0000042072.18151.6f. 15537163 1.0 2020-03-18 23:23:50 UTC 2020-08-04 22:24:31 UTC CDB000075 Piperidine Piperidine, named after the genus Piper, which is Latin for pepper, has the molecular formula (CH2)5NH. It is a heterocyclic amine which consists of a six-membered ring containing five methylene units and one nitrogen atom. Piperidine is a strong basic compound. It is a colorless fuming liquid with an ammoniacal and pepper-like odor. It is found in black pepper fruit, oil and seed (Piper nigrum), barley seeds, celery plant, bell pepper and tobacco ( http://www.thegoodscentscompany.com/data/rw1009201.html#tooccur). Piperidine is also a constituent of cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). In addition to cannabis plants (PMID: 6991645), piperidine was obtained from the plants¬†Psilocaulon absimile¬†(Aizoaceae) and in¬†Petrosimonia monandra ( https://en.wikipedia.org/wiki/Piperidine#cite_note-17). Piperidine is metabolized by microbes and is potentially used as an anti-bacterial agent controlling bacterial populations within rhizomes (http//doi.org/10.1101/499731). Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals such as vasodilators and antipsychotic medications (PMID: 25255204). Piperidine is a widely used secondary amine and used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction. Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents. Azacyclohexane Azinane Cyclopentimine Hexahydropyridine Pentamethyleneamine Pentamethyleneimine Pentamethylenimine pip Cypentil FEMA 2908 Hexahydro-pyridine Hexazane Perhydropyridine Piperidin Piperidine ON rasta resin C5H11N 85.15 85.0891 piperidine piperidine 110-89-4 C1CCNCC1 InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 NQRYJNQNLNOLGT-UHFFFAOYSA-N belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. Piperidines Organic compounds Organoheterocyclic compounds Piperidines Aliphatic heteromonocyclic compounds Azacyclic compounds Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Aliphatic heteromonocyclic compound Amine Azacycle Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Piperidine Secondary aliphatic amine Secondary amine azacycloalkane piperidines saturated organic heteromonocyclic parent secondary amine water_solubility 1000 mg/mL at 20 °C logp 0.84 melting_point -9 °C boiling_point 106 °C Wikipedia logp 0.97 ALOGPS logs 0.16 ALOGPS logp 0.66 ChemAxon pka_strongest_basic 10.4 ChemAxon iupac piperidine ChemAxon average_mass 85.15 ChemAxon mono_mass 85.0891 ChemAxon smiles C1CCNCC1 ChemAxon formula C5H11N ChemAxon inchi InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 ChemAxon inchikey NQRYJNQNLNOLGT-UHFFFAOYSA-N ChemAxon polar_surface_area 12.03 ChemAxon refractivity 26.84 ChemAxon polarizability 10.43 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012644 7791 8082 18049 C01746 PIPERIDINE Piperidine PIP Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Vitaku E, Smith DT, Njardarson JT: Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J Med Chem. 2014 Dec 26;57(24):10257-74. doi: 10.1021/jm501100b. Epub 2014 Oct 7. 25255204 1.0 2020-03-18 23:23:53 UTC 2020-08-04 22:24:31 UTC CDB000076 Nonanal Nonanal, also known as nonyl aldehyde or pelargonaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. It is a fatty aldehyde lipid molecule. Nonanal, a colourless, oily liquid, is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, from yeast to humans. Nonanal has an aldehydic, citrus, and fat taste. Nonanal is found in highest concentration in corns, tea, and gingers and in lower concentrations in sweet oranges, carrots, and limes. It has also been detected in olives, cereals and cereal products, Chinese cinnamons, common grapes, and oats, making nonanal a potential biomarker for the consumption of these foods. Nonanal is also a component of cannabis plants (PMID: 6991645). Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene (doi:10.1002/14356007.a01_321.pub2). Nonanal, an odorant of humans and birds, attracts Culex mosquitoes, which have extremely sensitive olfactory neurons in their antennae ( PMID: 19858490) for nonanal. Nonanal has been associated with several diseases such as pervasive developmental disorder not otherwise specified, autism (PMID: 24130822), Crohn's disease (PMID: 26071410), ulcerative colitis and non-alcoholic fatty liver disease (PMID: 23454028). N-Nonaldehyde Nonanoic aldehyde Nonyl aldehyde Nonylaldehyde Nonylic aldehyde Pelargonaldehyde Pelargonic aldehyde N-Nonylaldehyde Nonanal C9H18O 142.24 142.1358 nonanal nonanal CCCCCCCCC=O InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3 GYHFUZHODSMOHU-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide Fatty aldehydes an <i>n</i>-alkanal fatty aldehyde melting_point −18 °C Wikipedia boiling_point 191 °C Wikipedia logp 3.81 ALOGPS logs -3.37 ALOGPS logp 2.99 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac nonanal ChemAxon average_mass 142.24 ChemAxon mono_mass 142.1358 ChemAxon smiles CCCCCCCCC=O ChemAxon formula C9H18O ChemAxon inchi InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3 ChemAxon inchikey GYHFUZHODSMOHU-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 43.95 ChemAxon polarizability 18.54 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003303 29029 31289 84268 CPD-8491 C00030828 Nonanal Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Syed Z, Leal WS: Acute olfactory response of Culex mosquitoes to a human- and bird-derived attractant. Proc Natl Acad Sci U S A. 2009 Nov 3;106(44):18803-8. doi: 10.1073/pnas.0906932106. Epub 2009 Oct 26. 19858490 De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. 24130822 Hicks LC, Huang J, Kumar S, Powles ST, Orchard TR, Hanna GB, Williams HR: Analysis of Exhaled Breath Volatile Organic Compounds in Inflammatory Bowel Disease: A Pilot Study. J Crohns Colitis. 2015 Sep;9(9):731-7. doi: 10.1093/ecco-jcc/jjv102. Epub 2015 Jun 12. 26071410 Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. 23454028 1.0 2020-03-18 23:23:55 UTC 2020-08-04 22:24:33 UTC CDB000077 Methyl linoleate Methyl linoleate belongs to the class of organic compounds known as linoleic acids which are derivatives of linoleic acid. Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. Methyl linoleate is an essentially neutral compound that is almost insoluble in water and soluble in alcohol. It has a low oily, fatty, woody odor ( http://www.thegoodscentscompany.com/data/rw1260021.html). Linoleic acid is an essential fatty acid that humans do not synthesize and must obtain from diet. Methyl linoleate is a simple ester found in cannabis plant (PMID: 6991645) and is found in clove bud and fruit, garlic bulb, jasmin, white mustard, parsley leaf oil and witch hazel leaf oil ( http://www.thegoodscentscompany.com/data/rw1260021.html#tooccur) . It is part of a mixture with methyl linolenate (*FEMA 3411*) which is used as a flavouring ingredient in condiments and spices. Methyl linoleic acid (Z,Z)-9,12-Octadecadienoic acid methyl ester 9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester 9,12-Octadecadienoic acid (Z,Z)-, methyl ester 9,12-Octadecadienoic acid, methyl ester 9,12-Octadecadienoic acid, methyl ester, (Z,Z) cis-9,cis-12-Octadecadienoic acid, methyl ester cis-Linoleic acid methyl ester Linoleic acid methyl ester Linoleic acid, methyl ester Linoleic acid, methyl ester (8ci) Linoleic acid,methyl ester Methyl (9Z,12Z)-9,12-octadecadienoate Methyl (9Z,12Z)-octadeca-9,12-dienoate Methyl (Z,Z)-9,12-octadecadienoate Methyl (Z,Z)-9,12-octadienoate Methyl 9-cis,12-cis-octadecadienoate Methyl cis,cis-9, 12-octadecadienoate Methyl cis,cis-9,12-octadecadienoate Methyl ester(Z,Z)-9,12-octadecadienoic acid Methyl lineoleate Methyl linolate Methyl linoleate, native Methyl octadeca-9,12-dienoate Methyl octadecadienoate Natural methyl linoleate Methyl linoleate, (e,e)-isomer Methyl linoleate, (e,Z)-isomer Methyl linoleate, 1-(14)C-labeled, (Z,Z)-isomer Methyl linoleate, (Z,e)-isomer C19H34O2 294.47 294.2559 methyl (9E,12Z)-octadeca-9,12-dienoate methyl (9E,12Z)-octadeca-9,12-dienoate 112-63-0 CCCCC\C=C/C\C=C\CCCCCCCC(=O)OC InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10+ WTTJVINHCBCLGX-QEFCTBRHSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Fatty acid methyl esters Hydrocarbon derivatives Methyl esters Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acid methyl ester Hydrocarbon derivative Methyl ester Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound logp 6.95 ALOGPS logs -6.76 ALOGPS logp 6.57 ChemAxon pka_strongest_basic -7 ChemAxon iupac methyl (9E,12Z)-octadeca-9,12-dienoate ChemAxon average_mass 294.47 ChemAxon mono_mass 294.2559 ChemAxon smiles CCCCC\C=C/C\C=C\CCCCCCCC(=O)OC ChemAxon formula C19H34O2 ChemAxon inchi InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10+ ChemAxon inchikey WTTJVINHCBCLGX-QEFCTBRHSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 93.29 ChemAxon polarizability 37.45 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5462988 FDB012761 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:23:57 UTC 2020-08-04 22:27:17 UTC CDB000078 beta-Caryophyllene beta-Caryophyllene, also known as caryophyllene or (‚àí)-Œ≤-caryophyllene, is a natural bicyclic sesquiterpene. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and Œ±-humulene (obsolete name: Œ±-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature. It is barely soluble in water and soluble in alcohol and propylene glycol. beta-Caryophyllene, a promising precursor for the production of high density fuels, has been biosynthesized in E.coli from the common terpene precursors dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). First, single units of DMAPP and IPP are reacted via a substitution, nucleophilic (SN)1-type reaction with the loss of pyrophosphate, catalyzed by the enzyme geranyl diphosphate synthetase (GPPS2), to form geranyl pyrophosphate (GPP). This further reacts with a second unit of IPP, also via an SN1-type reaction catalyzed by the enzyme farnesyl diphospahe synthetase (IspA), to form farnesyl pyrophosphate (FPP). Finally, FPP undergoes beta-caryophyllene synthase -catalyzed intramolecular cyclization to form caryophyllene (https://doi.org/10.1016%2Fj.renene.2016.06.061). It is an abundant constituent of many essential oils including that of Syzygium aromaticum (clove bud, up to 19%; ), Cannabis sativa flower (up to 37%; http://www.internationalhempassociation.org/jiha/jiha4208.html; PMID: 6991645), rosemary, and hops. beta-Caryophyllene is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva. Beta-caryophyllene is a major sesquiterpene of¬†various plant essential oils that reportedly has antioxidant, anti-inflammatory (PMID: 24484210), anticancer (PMID: 27696789), cardioprotective (PMID: 30343038), hepatoprotective, gastroprotective, nephroprotective, antimicrobial, immune-modulatory activity and neuroprotective effects. It has a role in alleviating pain, anxiety, spasm, convulsion, depression, alcoholism, and Alzheimer's disease and may mediates these effects through interactions with the cannabinoid receptors (CR), especially CBR2 (PMID: 30281175; PMID: 18574142). C15H24 204.36 204.1878 (1S,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene (1S,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene 87-44-5 C\C1=C\CCC(=C)[C@H]2CC(C)(C)[C@H]2CC1 InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14+/m1/s1 NPNUFJAVOOONJE-FGHOCRGKSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Caryophyllane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.35 ALOGPS logs -4.83 ALOGPS logp 4.52 ChemAxon iupac (1S,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C\C1=C\CCC(=C)[C@H]2CC(C)(C)[C@H]2CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14+/m1/s1 ChemAxon inchikey NPNUFJAVOOONJE-FGHOCRGKSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.45 ChemAxon polarizability 25.96 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5498518 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Sain S, Naoghare PK, Devi SS, Daiwile A, Krishnamurthi K, Arrigo P, Chakrabarti T: Beta caryophyllene and caryophyllene oxide, isolated from Aegle marmelos, as the potent anti-inflammatory agents against lymphoma and neuroblastoma cells. Antiinflamm Antiallergy Agents Med Chem. 2014 Mar;13(1):45-55. doi: 10.2174/18715230113129990016. 24484210 Fidyt K, Fiedorowicz A, Strzadala L, Szumny A: beta-caryophyllene and beta-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med. 2016 Oct;5(10):3007-3017. doi: 10.1002/cam4.816. Epub 2016 Sep 30. 27696789 Youssef DA, El-Fayoumi HM, Mahmoud MF: Beta-caryophyllene protects against diet-induced dyslipidemia and vascular inflammation in rats: Involvement of CB2 and PPAR-gamma receptors. Chem Biol Interact. 2019 Jan 5;297:16-24. doi: 10.1016/j.cbi.2018.10.010. Epub 2018 Oct 19. 30343038 Machado KDC, Islam MT, Ali ES, Rouf R, Uddin SJ, Dev S, Shilpi JA, Shill MC, Reza HM, Das AK, Shaw S, Mubarak MS, Mishra SK, Melo-Cavalcante AAC: A systematic review on the neuroprotective perspectives of beta-caryophyllene. Phytother Res. 2018 Dec;32(12):2376-2388. doi: 10.1002/ptr.6199. Epub 2018 Oct 3. 30281175 Gertsch J, Leonti M, Raduner S, Racz I, Chen JZ, Xie XQ, Altmann KH, Karsak M, Zimmer A: Beta-caryophyllene is a dietary cannabinoid. Proc Natl Acad Sci U S A. 2008 Jul 1;105(26):9099-104. doi: 10.1073/pnas.0803601105. Epub 2008 Jun 23. 18574142 1.0 2020-03-18 23:23:59 UTC 2020-09-11 20:08:29 UTC CDB000079 Guaiol Guaiol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 17467679). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Guaiol is an essentially neutral compound with low solubility in water but soluble in alcohol. Guaiol is found in several plants, especially in the oil of guaiacum and cypress pine. Guaiol is one of many terpenes found in Cannabis and it has been associated with decreased anxiolytic activity (PMID: 30405331). (-)-Guaiol, a sesquiterpene alcohol with the guaiane skeleton, has been found in many Chinese medicinal plants and been reported to comprise various guaiane natural products that are well known for their antibacterial activities. (-)-Guaiol has anti-cancer properties inhibiting the proliferation of non small cell lung cancer (NSCLC) cells (PMID:29611762) and inducing autophagy ( PMID: 27566579), by specifically targeting mTOR signaling pathways, including both mTORC1 and mTORC2 signaling, possibly providing a better therapeutic substitution for rapamycin in the treatment of NSCLC patients. It has anti-leishmanial activity (PMID: 29352826) and is an insecticide that inhibits aphids ( PMID: 24354171) C15H26O 222.37 222.1984 2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol 2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol 489-86-1 C[C@H]1CCC2=C1C[C@H](CC[C@@H]2C)C(C)(C)O InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12-/m0/s1 TWVJWDMOZJXUID-SRVKXCTJSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol melting_point 92 °C Wikipedia logp 4.48 ALOGPS logs -3.45 ALOGPS logp 3.42 ChemAxon pka_strongest_acidic 19.37 ChemAxon pka_strongest_basic -0.89 ChemAxon iupac 2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles C[C@H]1CCC2=C1C[C@H](CC[C@@H]2C)C(C)(C)O ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12-/m0/s1 ChemAxon inchikey TWVJWDMOZJXUID-SRVKXCTJSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 69.24 ChemAxon polarizability 27.67 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 92245464 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Yang X, Zhu J, Wu J, Huang N, Cui Z, Luo Y, Sun F, Pan Q, Li Y, Yang Q: (-)-Guaiol regulates autophagic cell death depending on mTOR signaling in NSCLC. Cancer Biol Ther. 2018 Aug 3;19(8):706-714. doi: 10.1080/15384047.2018.1451277. Epub 2018 Apr 19. 29611762 Kamal BS, Kamal F, Lantela DE: Cannabis and the Anxiety of Fragmentation-A Systems Approach for Finding an Anxiolytic Cannabis Chemotype. Front Neurosci. 2018 Oct 22;12:730. doi: 10.3389/fnins.2018.00730. eCollection 2018. 30405331 Yang Q, Wu J, Luo Y, Huang N, Zhen N, Zhou Y, Sun F, Li Z, Pan Q, Li Y: (-)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer. Oncotarget. 2016 Sep 20;7(38):62585-62597. doi: 10.18632/oncotarget.11540. 27566579 Garcia MCF, Soares DC, Santana RC, Saraiva EM, Siani AC, Ramos MFS, Danelli MDGM, Souto-Padron TC, Pinto-da-Silva LH: The in vitro antileishmanial activity of essential oil from Aloysia gratissima and guaiol, its major sesquiterpene against Leishmania amazonensis. Parasitology. 2018 Aug;145(9):1219-1227. doi: 10.1017/S0031182017002335. Epub 2018 Jan 21. 29352826 Liu T, Wang CJ, Xie HQ, Mu Q: Guaiol--a naturally occurring insecticidal sesquiterpene. Nat Prod Commun. 2013 Oct;8(10):1353-4. 24354171 1.0 2020-03-18 23:24:02 UTC 2020-07-24 23:30:05 UTC CDB000080 Hexyl butyrate Butanoic acid-hexyl ester or hexyl butyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid consisting of 6 or more carbons. Hexyl butyrate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a clear, colorless liquid obtained by the formal condensation of hexanol with butyric acid. Hexyl butyrate has a sweet, slightly waxy, fruity, apple, and apple peel aroma, with a similar green/soapy taste. Hexyl butyrate occurs naturally in many fruits and has been detected, but not quantified in apples, yellow passion fruit, roman camomiles, pears, sweet cherries, and other fruits. This could make hexyl butyrate a potential biomarker for the consumption of these foods. Hexyl butyrate is one of the main volatile chemicals released by the Tarnished plant bugs, Lygus hesperus and Lygus lineolaris when they are attacked or disturbed ( PMID: 12775153). Hexyl butyrate has also been found in Cannabis sativa (PMID: 6991645, 26657499). Hexyl butyric acid 1-Hexyl butyrate Butanoic acid, hexyl ester Butyric acid, hexyl ester Hexyl butanoate N-Hexyl butanoate N-Hexyl butyrate N-Hexyl N-butanoate N-Hexyl N-butyrate C10H20O2 172.26 172.1463 hexyl butanoate butanoic acid, hexyl ester 2639-63-6 CCCCCCOC(=O)CCC InChI=1S/C10H20O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3-9H2,1-2H3 XAPCMTMQBXLDBB-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Fatty acid esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters fatty acid ester melting_point -78 °C logp 3.83 ALOGPS logs -3.21 ALOGPS logp 3.28 ChemAxon pka_strongest_basic -7 ChemAxon iupac hexyl butanoate ChemAxon average_mass 172.26 ChemAxon mono_mass 172.1463 ChemAxon smiles CCCCCCOC(=O)CCC ChemAxon formula C10H20O2 ChemAxon inchi InChI=1S/C10H20O2/c1-3-5-6-7-9-12-10(11)8-4-2/h3-9H2,1-2H3 ChemAxon inchikey XAPCMTMQBXLDBB-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 49.72 ChemAxon polarizability 21.52 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 16570 FDB011708 17525 87559 C00035702 Wardle AR, Borden JH, Pierce HD Jr, Gries R: Volatile compounds released by disturbed and calm adults of the tarnished plant bug, Lygus lineolaris. J Chem Ecol. 2003 Apr;29(4):931-44. doi: 10.1023/a:1022987901330. 12775153 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-18 23:24:04 UTC 2020-08-04 22:27:25 UTC CDB000081 Citronellol Citronellol is formally classified as alkylalcohol although it is biochemically a monoterpenoid as it is synthesized from isoprene units. Citronellol is a neutral compound. It is a naturally occurring organic compound found in cannabis plants (PMID: 6991645). Citronellol occurs in many essential oils as either ‚Äì or + enantiomers. -Citronellol is found in the oils of rose (18-55%) and Pelargonium geraniums while + citronellol is found in citronella oils extracted from the leaves and stems of Cymbopogon nardus or citronella grass. Citronellol has a citrus, floral, and geranium taste with a floral¬†leathery¬†waxy¬†rose¬†citrus odor ( http://www.thegoodscentscompany.com/data/rw1007032.html#tophyp). It is used in perfumery to add scents to soaps and incense. It is an insect repellent that repels mosquitos at short distances (PMID: 2862274). Citronellol is found in highest concentrations in gingers, sweet basils, and winter savories and in lower concentrations in highbush blueberries, bilberries, and cardamoms. Citronellol has also been detected in blackcurrants, fennels, evergreen blackberries, herbs and spices, and nutmegs making citronellol a potential biomarker for the consumption of these foods. Citronellol has promising pharmacological activities (PMID: 30453001) against human lung cancer (PMID: 31280209), against induced rat breast cancer (PMID: 31313341), has antifungal activity against Candida species (PMID: 32150884) and has anti-hypertensive properties (PMID: 26872991). (-)-3,7-Dimethyloct-6-en-1-ol (-)-Citronellol (S)-3,7-Dimethyl-6-octen-1-ol (-)-(S)-Citronellol (-)-beta-Citronellol (-)-Β-citronellol (3S)-3,7-Dimethyl-6-octen-1-ol (S)-(-)-Citronellol (S)-(-)-beta-Citronellol (S)-(-)-Β-citronellol (S)-Citronellol (S)-beta-Citronellol (S)-Β-citronellol L-Citronellol l-Citronellol (-)-3,7-Dimethyl-6-octen-1-ol 3,7-Dimethyl-6-octen-1-ol (±)-3,7-Dimethyl-6-octen-1-ol (±)-Citronellol (±)-beta-Citronellol (±)-β-Citronellol 1-Hydroxy-3,7-dimethyl-6-octene 2,3-Dihydrogeraniol 2,6-Dimethyl-2-octen-8-ol dl-Citronellol Dihydrogeraniol beta-Citronellol β-Citronellol C10H20O 156.27 156.1514 (3S)-3,7-dimethyloct-6-en-1-ol (-)-citronellol 7540-51-4 C[C@H](CCO)CCC=C(C)C InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m0/s1 QMVPMAAFGQKVCJ-JTQLQIEISA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Fatty alcohols Hydrocarbon derivatives Primary alcohols Acyclic monoterpenoid Alcohol Aliphatic acyclic compound Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes citronellol boiling_point 225 °C Wikipedia logp 3.48 ALOGPS logs -2.27 ALOGPS logp 2.75 ChemAxon pka_strongest_acidic 17.11 ChemAxon pka_strongest_basic -1.9 ChemAxon iupac (3S)-3,7-dimethyloct-6-en-1-ol ChemAxon average_mass 156.27 ChemAxon mono_mass 156.1514 ChemAxon smiles C[C@H](CCO)CCC=C(C)C ChemAxon formula C10H20O ChemAxon inchi InChI=1S/C10H20O/c1-9(2)5-4-6-10(3)7-8-11/h5,10-11H,4,6-8H2,1-3H3/t10-/m0/s1 ChemAxon inchikey QMVPMAAFGQKVCJ-JTQLQIEISA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 50.49 ChemAxon polarizability 20.1 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013723 7793 C11386 88 C00000844 Citronellol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Taylor WG, Schreck CE: Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol. J Pharm Sci. 1985 May;74(5):534-9. doi: 10.1002/jps.2600740508. 2862274 Santos PL, Matos JPSCF, Picot L, Almeida JRGS, Quintans JSS, Quintans-Junior LJ: Citronellol, a monoterpene alcohol with promising pharmacological activities - A systematic review. Food Chem Toxicol. 2019 Jan;123:459-469. doi: 10.1016/j.fct.2018.11.030. Epub 2018 Nov 16. 30453001 Yu WN, Lai YJ, Ma JW, Ho CT, Hung SW, Chen YH, Chen CT, Kao JY, Way TD: Citronellol Induces Necroptosis of Human Lung Cancer Cells via TNF-alpha Pathway and Reactive Oxygen Species Accumulation. In Vivo. 2019 Jul-Aug;33(4):1193-1201. doi: 10.21873/invivo.11590. 31280209 Rajendran J, Pachaiappan P, Subramaniyan S: Dose-dependent chemopreventive effects of citronellol in DMBA-induced breast cancer among rats. Drug Dev Res. 2019 Sep;80(6):867-876. doi: 10.1002/ddr.21570. Epub 2019 Jul 16. 31313341 Silva D, Diniz-Neto H, Cordeiro L, Silva-Neta M, Silva S, Andrade-Junior F, Leite M, Nobrega J, Morais M, Souza J, Rosa L, Melo T, Souza H, Sousa A, Rodrigues G, Oliveira-Filho A, Lima E: (R)-(+)-beta-Citronellol and (S)-(-)-beta-Citronellol in Combination with Amphotericin B against Candida Spp. Int J Mol Sci. 2020 Mar 5;21(5). pii: ijms21051785. doi: 10.3390/ijms21051785. 32150884 Ribeiro-Filho HV, de Souza Silva CM, de Siqueira RJ, Lahlou S, dos Santos AA, Magalhaes PJ: Biphasic cardiovascular and respiratory effects induced by beta-citronellol. Eur J Pharmacol. 2016 Mar 15;775:96-105. doi: 10.1016/j.ejphar.2016.02.025. Epub 2016 Feb 9. 26872991 1.0 2020-03-18 23:24:06 UTC 2020-09-11 20:08:31 UTC CDB000082 delta-Cadinene (+)-1(10),4-Cadinadiene, also known as delta-cadinene, one of the 4 isomers of Cadinene, belongs to the class of organic compounds known as sesquiterpenoids which are terpenes with three consecutive isoprene units. delta-Cadinene is an isoprenoid lipid molecule that is very hydrophobic, almost insoluble in water, soluble in alcohol and relatively neutral. Cadinene isomers were first isolated from oil of the wood of the Cade juniper, from which its name was derived. delta-Cadinene has a dry, thyme, herbal, and medicine taste (http://www.thegoodscentscompany.com/data/rw1054621.html). It is the trivial chemical name of several isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants such as cannabis plants (PMID:6991645). 4-Cadinadiene occurs in the essential oils of all-spice, ylang-ylang,¬†citronella, cubebs, and sweet flag. delta-Cadinadiene is found in highest concentrations in common oregano, hyssops, and lemon balms and in lower concentrations in sweet basils, spearmints, and winter savories. delta-Cadinene has also been detected in bread, macadamia nuts, common cabbages, moth beans, and half-highbush blueberries making delta-Cadinene a potential biomarker for the consumption of these foods. Delta-Cadinene has anti-cancer properties as it inhibited the growth of ovarian cancer cells (PMID: 26261482).¬† (1R,8AS)-4,7-dimethyl-1-isopropyl-1,2,3,5,6,8a-hexahydronaphthalene (1R,8AS)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene (-)-Δ-cadinene C15H24 204.36 204.1878 (1R,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene (-)-delta-cadinene 483-76-1 CC(C)[C@H]1CCC(C)=C2CCC(C)=C[C@H]12 InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13,15H,5-8H2,1-4H3/t13-,15-/m1/s1 FUCYIEXQVQJBKY-UKRRQHHQSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cadinane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon cadinene logp 4.92 ALOGPS logs -3.69 ALOGPS logp 4.4 ChemAxon iupac (1R,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@H]1CCC(C)=C2CCC(C)=C[C@H]12 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13,15H,5-8H2,1-4H3/t13-,15-/m1/s1 ChemAxon inchikey FUCYIEXQVQJBKY-UKRRQHHQSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.33 ChemAxon polarizability 26.62 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20182 63703 12306055 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Hui LM, Zhao GD, Zhao JJ: delta-Cadinene inhibits the growth of ovarian cancer cells via caspase-dependent apoptosis and cell cycle arrest. Int J Clin Exp Pathol. 2015 Jun 1;8(6):6046-56. eCollection 2015. 26261482 1.0 2020-03-18 23:24:08 UTC 2020-09-11 20:08:57 UTC CDB000083 Tyrosine Tyrosine or L-tyrosine, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tyrosine is a very strong basic compound (based on its pKa). Tyrosine is an odorless tasting compound. Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the body's sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the body's natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur, such as hawkinsinuria and tyrosinemia I. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinson's, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinson's. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa (http://www.dcnutrition.com). Outside of the human body, Tyrosine is found, on average, in the highest concentration within a few different foods, such as caseins, milk (cow), and other soy products and in a lower concentration in semolina, crayfish, and crabs. Tyrosine has also been detected, but not quantified in, several different foods, such as annual wild rices, lovages, corianders, lumpsuckers, and sugars. This could make Tyrosine a potential biomarker for the consumption of these foods. (2R)-2-Amino-3-(4-hydroxyphenyl)propanoic acid (R)-2-Amino-3-(p-hydroxyphenyl)propionic acid (R)-3-(p-Hydroxyphenyl)alanine D-Tyr D-Tyrosin DTY (2R)-2-Amino-3-(4-hydroxyphenyl)propanoate (R)-2-Amino-3-(p-hydroxyphenyl)propionate C9H11NO3 181.19 181.0739 (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid (.+-.)-tyrosine 556-02-5 N[C@H](CC1=CC=C(O)C=C1)C(O)=O InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1 OUYCCCASQSFEME-MRVPVSSYSA-N belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tyrosine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Amino acids Amphetamines and derivatives Aralkylamines Carbonyl compounds Carboxylic acids D-alpha-amino acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Phenylalanine and derivatives Phenylpropanoic acids 1-hydroxy-2-unsubstituted benzenoid 3-phenylpropanoic-acid Alpha-amino acid Amine Amino acid Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid D-alpha-amino acid Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenylalanine or derivatives Primary aliphatic amine Primary amine Tyrosine or derivatives D-alpha-amino acid Other amino acids tyrosine water_solubility 0.0453 g/100 mL Wikipedia logp -2.39 ALOGPS logs -1.37 ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 2 ChemAxon pka_strongest_basic 9.19 ChemAxon iupac (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid ChemAxon average_mass 181.19 ChemAxon mono_mass 181.0739 ChemAxon smiles N[C@H](CC1=CC=C(O)C=C1)C(O)=O ChemAxon formula C9H11NO3 ChemAxon inchi InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1 ChemAxon inchikey OUYCCCASQSFEME-MRVPVSSYSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 47.1 ChemAxon polarizability 18.06 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB03839 71098 C06420 28479 D-TYROSINE Tyrosine 1.0 2020-03-18 23:24:10 UTC 2020-08-04 22:27:32 UTC CDB000084 Safranal Safranal belongs to the class of organic compounds known as organic oxides which contain an oxide group. Safranal is a neutral compound. Safranal is a component of saffron (PMID: 28705037), the spice made from drying the stigmas and styles of crocus flowers (Crocus sativus). Safranal, the constituent primarily responsible for the aroma of saffron, has a sweet, fresh, and herbal taste and is a flavouring ingredient. Safranal has been detected in cauliflowers, cumin seeds, elderberry, figs, lemon, rooibos, saffrons, wolfberry, and tea leaf making safranal a potential biomarker for the consumption of these foods. Safranal is found in cannabis plants (PMID:6991645). Safranal is an effective anticonvulsant (PMID: 29609687) shown to act as an agonist at the¬†gamma aminobutyric acid (GABA)A-benzodiazepine receptor complex (PMID: 16707256). Safranal also exhibits high antioxidant and free radical scavenging activity (PMID: 16317646), along with cytotoxicity towards cancer cells in vitro (PMID: 8620447). It has also been shown to have antidepressant properties (PMID: 15341662). (2,6,6-Trimethylcyclohexa-1,3-dienyl)methanal 1,1,3-Trimethyl-2-formylcyclohexa-2,4-diene 2,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde 2,6,6-Trimethylcyclohexa-1,3-dienyl methanal Dehydro-beta-cyclocitral Dehydro-b-cyclocitral Dehydro-β-cyclocitral 1-Formyl-2,6,6-trimethyl-1,3-cyclohexadiene 2,3-Dihydro-2,2,6-trimethylbenzaldehyde 2,6,6-Trimethyl-1,3-cyclohexadienal 2,6,6-Trimethyl-1,3-cyclohexadiene-1-carbaldehyde 2,6,6-Trimethyl-1,3-cyclohexadienecarboxaldehyde, 9ci FEMA 3389 C10H14O 150.22 150.1045 2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde safranal 116-26-7 CC1=C(C=O)C(C)(C)CC=C1 InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 SGAWOGXMMPSZPB-UHFFFAOYSA-N belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. Organic oxides Organic compounds Organic oxygen compounds Organic oxides Aliphatic homomonocyclic compounds Aldehydes Hydrocarbon derivatives Aldehyde Aliphatic homomonocyclic compound Carbonyl group Hydrocarbon derivative Organic oxide Organooxygen compound an apocarotenoid monoterpenoid melting_point < 25 °C boiling_point 70 °C at 1 mmHg Wikipedia logp 2.93 ALOGPS logs -2.04 ALOGPS logp 2.05 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC1=C(C=O)C(C)(C)CC=C1 ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 ChemAxon inchikey SGAWOGXMMPSZPB-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 48.22 ChemAxon polarizability 17.32 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014884 61041 55000 C17062 53169 C00035737 CPD-8669 Safranal Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rameshrad M, Razavi BM, Hosseinzadeh H: Saffron and its derivatives, crocin, crocetin and safranal: a patent review. Expert Opin Ther Pat. 2018 Feb;28(2):147-165. doi: 10.1080/13543776.2017.1355909. Epub 2017 Jul 18. 28705037 Bo-Qiang L, Si-Tong Z, Zu-Yuan L, Wan-Yun N, Bin C, Yuan L, Xuyun L, Liangen M, You-Chao C, Xin-Zhen Y, Zhong C, Xiao-Ying Y, Wei-Wei H: Safranal carried by nanostructured lipid vehicles inhibits generalized epilepsy in mice. Pharmazie. 2018 Apr 2;73(4):207-212. doi: 10.1691/ph.2018.7310. 29609687 Hosseinzadeh H, Sadeghnia HR: Protective effect of safranal on pentylenetetrazol-induced seizures in the rat: involvement of GABAergic and opioids systems. Phytomedicine. 2007 Apr;14(4):256-62. doi: 10.1016/j.phymed.2006.03.007. Epub 2006 May 16. 16707256 Assimopoulou AN, Sinakos Z, Papageorgiou VP: Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents. Phytother Res. 2005 Nov;19(11):997-1000. doi: 10.1002/ptr.1749. 16317646 Escribano J, Alonso GL, Coca-Prados M, Fernandez JA: Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro. Cancer Lett. 1996 Feb 27;100(1-2):23-30. doi: 10.1016/0304-3835(95)04067-6. 8620447 Akhondzadeh S, Fallah-Pour H, Afkham K, Jamshidi AH, Khalighi-Cigaroudi F: Comparison of Crocus sativus L. and imipramine in the treatment of mild to moderate depression: a pilot double-blind randomized trial [ISRCTN45683816]. BMC Complement Altern Med. 2004 Sep 2;4:12. doi: 10.1186/1472-6882-4-12. 15341662 1.0 2020-03-18 23:24:12 UTC 2020-06-30 00:14:39 UTC CDB000085 Ethylamine Ethylamine, also known as 1-aminoethane or ethanamine, belongs to the class of organic compounds known as monoalkylamines which contain a primary aliphatic amine group. Ethylamine is a moderately basic compound with an ammonia and fishy taste and ammonia-like odor. Ethylamine exists in all living organisms, from bacteria to humans It is a simple amine found in cannabis plants (PMID: 6991645). Ethylamine is found in highest concentrations in barley, apples, and corns and in lower concentrations in white cabbages, wild carrots, and cabbages. Ethylamine was detected in black elderberries, common grapes, French plantains, soybeans, and spinachs making ethylamine a potential biomarker for the consumption of these foods. Ethylamine is precursor for herbicides and is found in rubber products (http//doi:10.1002/14356007.a02_001) 1-Aminoethane Aminoethane ETHANAMINE Aethylamine Ethyl amine Ethylamine solution Etilamina Etyloamina Monoethylamine Ethylamine hydrochloride Ethylamine hydrobromide Ethylamine, 14C-labeled C2H7N 45.08 45.0578 ethanamine ethylamine 75-04-7 CCN InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3 QUSNBJAOOMFDIB-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine a small molecule primary aliphatic amine logp -0.13 HANSCH,C ET AL. (1995) melting_point -81.2 °C boiling_point 16 - 20 °C Wikipedia logp -0.20 ALOGPS logs 0.90 ALOGPS logp -0.27 ChemAxon pka_strongest_basic 10.23 ChemAxon iupac ethanamine ChemAxon average_mass 45.08 ChemAxon mono_mass 45.0578 ChemAxon smiles CCN ChemAxon formula C2H7N ChemAxon inchi InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3 ChemAxon inchikey QUSNBJAOOMFDIB-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 14.67 ChemAxon polarizability 5.75 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003242 6341 6101 C00797 ETHANAMINE Ethylamine NEH 15862 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:24:15 UTC 2020-07-24 23:30:05 UTC CDB000086 Carvone Carvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID: 27427817). Carvone is a volatile terpenoid found in cannabis plants (PMID: 6991645). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID: 5556886, 2477620). Carvone may help in the management of diseases (PMID: 30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID: 30087792) and patients with epilepsy (PMID: 31239862). It also has been successfully used as a biopesticide (PMID: 30250476). (-)-(4R)-Carvone (-)-(R)-Carvone (-)-p-Mentha-6,8-dien-2-one (4R)-Carvone (5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (R)-(-)-Carvone (R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (R)-5-Isopropenyl-2-methylcyclohex-2-en-1-one L-1-Methyl-4-isopropenyl-6-cyclohexen-2-one L-Carvone L-p-Mentha-1(6),8-dien-2-one Levo-carvone (-)-Carvone (4R)-(-)-Carvone (R)-(-)-p-Mentha-6,8-dien-2-one 2-Methyl-5-(1-methylethenyl)-(R)-2-cyclohexen-1-one L(-)-Carvone C10H14O 150.22 150.1045 (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one (-)-carvone 6485-40-1 CC(=C)[C@@H]1CC=C(C)C(=O)C1 InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1 ULDHMXUKGWMISQ-SECBINFHSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Cyclohexenones Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Cyclohexenone Hydrocarbon derivative Ketone Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids carvone water_solubility 1.31 mg/mL at 25 °C logp 2.71 melting_point < 15 °C boiling_point 231 °C Wikipedia logp 2.77 ALOGPS logs -2.11 ALOGPS logp 2.55 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC(=C)[C@@H]1CC=C(C)C(=O)C1 ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1 ChemAxon inchikey ULDHMXUKGWMISQ-SECBINFHSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 47.17 ChemAxon polarizability 17.65 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013718 388655 C01767 439570 15400 C00000807 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. 5556886 Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. 2477620 1.0 2020-03-18 23:24:17 UTC 2020-09-11 20:08:27 UTC CDB000087 Sabinene Sabinene or 4(10)-thujene, belongs to the class of organic compounds known as bicyclic monoterpenoids which contain 2 rings fused to each other. Thus, sabinene is an isoprenoid lipid molecule. It is very hydrophobic, practically insoluble in water and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Sabinene has a citrus, pepper, and pine taste and is responsible for the spiciness of pepper. Sabinene is found in the essential oils of a variety of plants/trees including the holm oak, Norway spruce, bay laurel (Laurus nobilis). common sage, and true nutmeg (Myristica fragrans tree; PMID: 5615546). Sabinene is also found in trace amounts in cannabis plants (PMID: 6991645). Sabinene is found in highest concentrations in nutmegs, tarragons, and sweet bay and in lower concentrations in common sages, caraway, and star anises. Sabinene has also been detected in saffrons, sunflowers, yellow bell peppers, summer savories, and pepper (C. annuum). Sabinene can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. The microbial biosynthesis of sabinene has been well studied to facilitate the industrial production of this important compound (PMID: 29264773). Sabinene has some medicinal properties as it induced recovery of myotube shrinkage in fasting rats, suggesting that it may reverse muscle atrophy (PMID: 31597276). (1R,5R)-1-Isopropyl-4-methylenebicyclo[3.1.0]hexane (1R,5R)-Sabinene (+)-Sabinene (1R,5R)-(+)-4(10)-Thujene (1R,5R)-(+)-Sabinene (1R,5R)-4-Methylene-1-(1-methylethyl)bicyclo[3.1.0]hexane 1-Isopropyl-4-methylenebicyclo[3.1.0]hexane 4(10)-Thujene 4-Methylene-1-(1-methylethyl)bicyclo[3.1.0]hexane Sabenene Sabinen Sabinene (+)-4(10)-Thujene d-4(10)-Thujene d-Sabinene C10H16 136.24 136.1252 (1R,5R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane (+)-sabinene 2009-00-9 CC(C)[C@@]12C[C@@H]1C(=C)CC2 InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10-/m1/s1 NDVASEGYNIMXJL-NXEZZACHSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Thujane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bicyclic monoterpenoids sabinene boiling_point 163 - 164 °C Wikipedia logp 3.04 ALOGPS logs -3.33 ALOGPS logp 2.86 ChemAxon iupac (1R,5R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)[C@@]12C[C@@H]1C(=C)CC2 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10-/m1/s1 ChemAxon inchikey NDVASEGYNIMXJL-NXEZZACHSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.65 ChemAxon polarizability 17.24 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014908 9063235 10887971 50029 C20230 C00000857 CPD-14013 Sabinene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Shulgin AT, Sargent T, Naranjo C: The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. Psychopharmacol Bull. 1967 Dec;4(3):13. 5615546 Cao Y, Zhang H, Liu H, Liu W, Zhang R, Xian M, Liu H: Biosynthesis and production of sabinene: current state and perspectives. Appl Microbiol Biotechnol. 2018 Feb;102(4):1535-1544. doi: 10.1007/s00253-017-8695-5. Epub 2017 Dec 20. 29264773 Ryu Y, Lee D, Jung SH, Lee KJ, Jin H, Kim SJ, Lee HM, Kim B, Won KJ: Sabinene Prevents Skeletal Muscle Atrophy by Inhibiting the MAPK-MuRF-1 Pathway in Rats. Int J Mol Sci. 2019 Oct 8;20(19). pii: ijms20194955. doi: 10.3390/ijms20194955. 31597276 1.0 2020-03-18 23:24:19 UTC 2020-09-11 20:08:31 UTC CDB000088 beta-Bisabolene beta-Bisabolene is biochemically a sesquiterpenoid, comprised of three isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms. beta-Bisabolene is an isoprenoid lipid molecule which is very hydrophobic, practically insoluble in water, and relatively neutral. Bisabolene has three isomers (Œ±-, Œ≤-, and Œ≥-bisabolene) which differ by the positions of the double bonds. beta-Bisabolene has a balsamic odor. Bisabolenes are naturally occurring sesquiterpenoid found in the essential oils of bisabol from the shrub Commiphora guidottii, and in a wide variety of other plants including cubeb, lemon, oregano and in trace amounts in cannabis plants (PMID: 6991645). beta-Bisabolene is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Bisabolenes are also produced by different insects such as stink bugs, fruit flies (PMID:11673844) and by several fungi (PMID: 25957494). Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds, including hernandulcin, a natural sweetener (PMID: 22867794) which is approved as a food additive in Europe. beta-Bisabolene has some medicinal properties. It had synergistic antibacterial activity with ampicillin against Staphylococcus aureus (PMID: 17235483) and was cytotoxic to breast cancer cell lines (PMID: 26666387). (-)-beta-Bisabolene (S)-(-)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene (S)-1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene beta-Bisabolene L-beta-Bisabolene (-)-b-Bisabolene (-)-Β-bisabolene b-Bisabolene Β-bisabolene L-b-Bisabolene L-Β-bisabolene (S)-b-Bisabolene (S)-Β-bisabolene C15H24 204.36 204.1878 (4S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene (-)-β-bisabolene 495-61-4 CC(C)=CCCC(=C)[C@H]1CCC(C)=CC1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1 XZRVRYFILCSYSP-OAHLLOKOSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bisabolane sesquiterpenoids Bisabolane sesquiterpenoids Bisabolanes beta-bisabolene logp 6.01 ALOGPS logs -4.39 ALOGPS logp 4.88 ChemAxon iupac (4S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCCC(=C)[C@H]1CCC(C)=CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1 ChemAxon inchikey XZRVRYFILCSYSP-OAHLLOKOSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 70.28 ChemAxon polarizability 26.84 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 49263 10104370 Bisabolene C00007242 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Lu F, Teal PE: Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Arch Insect Biochem Physiol. 2001 Nov;48(3):144-54. doi: 10.1002/arch.1067. 11673844 Spakowicz DJ, Strobel SA: Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential. Appl Microbiol Biotechnol. 2015 Jun;99(12):4943-51. doi: 10.1007/s00253-015-6641-y. Epub 2015 May 10. 25957494 Attia M, Kim SU, Ro DK: Molecular cloning and characterization of (+)-epi-alpha-bisabolol synthase, catalyzing the first step in the biosynthesis of the natural sweetener, hernandulcin, in Lippia dulcis. Arch Biochem Biophys. 2012 Nov 1;527(1):37-44. doi: 10.1016/j.abb.2012.07.010. Epub 2012 Jul 31. 22867794 Nascimento AM, Brandao MG, Oliveira GB, Fortes IC, Chartone-Souza E: Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. Antonie Van Leeuwenhoek. 2007 Jul;92(1):95-100. doi: 10.1007/s10482-006-9139-x. Epub 2007 Jan 18. 17235483 Yeo SK, Ali AY, Hayward OA, Turnham D, Jackson T, Bowen ID, Clarkson R: beta-Bisabolene, a Sesquiterpene from the Essential Oil Extract of Opoponax (Commiphora guidottii), Exhibits Cytotoxicity in Breast Cancer Cell Lines. Phytother Res. 2016 Mar;30(3):418-25. doi: 10.1002/ptr.5543. Epub 2015 Dec 15. 26666387 1.0 2020-03-18 23:24:21 UTC 2020-09-11 20:08:26 UTC CDB000089 Linalool Beta-Linalool or 3,7-Dimethyl-1,6-octadien-3-ol, also known simply as linalool is a naturally occurring terpene alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalool has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. There are two stereoisomers of Linalool ‚Äö√Ñ√¨ (S)-linalool and (R)-linalool. Linalool is used as a scent in 60% to 80% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions. Linalool is also used by pest professionals as a flea, fruit fly, and cockroach insecticide. Linalool is found in more than 200 different species of plants, including many flowers and spice plants. (S)-linalool is found, for example, as a major constituent of the essential oils of coriander (Coriandrum sativum L.), cymbopogon (Cymbopogon martini var. martinii), and sweet orange (Citrus sinensis) flowers. (R)-linalool is present in lavender (Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others. Linalool is also found in plants from the Lamiaceae family (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), Cinnamomum tamala, Solidago Meyen, Artemisia vulgaris (mugwort), Humulus lupulus. Linalool is also one of several monoterpenes that are found in cannabis plants (PMID: 6991645). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Like the majority of monoterpenes, linalool starts with the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl pyrophosphate (GPP) (PMID: 7640522). Linalool is then synthesized with the aid of linalool synthase (LIS) (PMID: 12572612). Linalool has a citrus, floral, rose, woody aroma and a citrus, orange, waxy taste. Linalool is found in a few different foods and spices, such as spearmints, corianders, common thymes, limes, grapes, lemons, grapefruit, oranges, pineapples, blackcurrants, basil, and common oregano. This could make, Linalool a potential biomarker for the consumption of these foods. Linalool is also synthesized, de novo, by yeast (C. cerevisiae) and may contribute to the floral tones found in some wines (PMID: 15668008). (+)-Linalool (3S)-3,7-Dimethyl-1,6-octadien-3-ol (3S)-Linalool (S)-(+)-Linalool (S)-3,7-Dimethyl-1,6-octadien-3-ol (S)-Linalol (-)-3,7-Dimethyl-1,6-octadien-3-ol (-)-Linalool (-)-R-Linalool (3R)-3,7-Dimethyl-1,6-octadien-3-ol (3R)-3,7-Dimethylocta-1,6-dien-3-ol (3R)-Linalool (R)-(-)-3,7-Dimethyl-1,6-octadien-3-ol (R)-(-)-Linalool (R)-Linalol (R)-Linalool L-Linalool Licareol C10H18O 154.25 154.1358 (3S)-3,7-dimethylocta-1,6-dien-3-ol (+)-linalool 126-90-9 CC(C)=CCC[C@](C)(O)C=C InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m1/s1 CDOSHBSSFJOMGT-SNVBAGLBSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Tertiary alcohols Acyclic monoterpenoid Alcohol Aliphatic acyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol Acyclic monoterpenoids Linear monoterpenes linalool water_solubility 1.589 g/L Wikipedia melting_point < −20 °C Wikipedia boiling_point 198 - 199 °C Wikipedia logp 2.68 ALOGPS logs -2.51 ALOGPS logp 2.65 ChemAxon pka_strongest_acidic 18.46 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (3S)-3,7-dimethylocta-1,6-dien-3-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)=CCC[C@](C)(O)C=C ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m1/s1 ChemAxon inchikey CDOSHBSSFJOMGT-SNVBAGLBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 50.21 ChemAxon polarizability 18.97 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014941 391430 67179 C11389 98 C00010301 CPD-8997 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Cseke L, Dudareva N, Pichersky E: Structure and evolution of linalool synthase. Mol Biol Evol. 1998 Nov;15(11):1491-8. doi: 10.1093/oxfordjournals.molbev.a025876. 12572612 Carrau FM, Medina K, Boido E, Farina L, Gaggero C, Dellacassa E, Versini G, Henschke PA: De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts. FEMS Microbiol Lett. 2005 Feb 1;243(1):107-15. doi: 10.1016/j.femsle.2004.11.050. 15668008 1.0 2020-03-18 23:24:24 UTC 2020-08-04 22:27:48 UTC CDB000090 Pyrrolidine Pyrrolidine, also known as azolidine, belongs to the class of organic compounds known as pyrrolidines which contain a pyrrolidine ring, a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. The pyrrolidine ring is the central structure of the amino acids, proline and hydroxyproline. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine and is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). Pyrrolidine is a strong basic compound and is soluble in most organic solvents. Pyrrolidine is a clear liquid with an unpleasant ammoniacal, fishy, shellfish-like taste and seaweed-like odor ( http://www.thegoodscentscompany.com/data/rw1009391.html). Pyrrolidine is found naturally in the leaves of tobacco and carrot and in cannabis plants (PMID:6991645). Pyrrolidine is present in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar, and fatty fish. Pyrrolidine is a flavouring agent added in trace amounts to chewing gum, soft candy, and non-alcoholic beverages (RoutledgeHandbooks-9781439847503-chapter3.pdf). Pyrrolidine is widely distributed in foodstuffs in trace amounts, presumably as a bacterial decarboxylation product of proline Pyrrolidine is a metabolite of the gram-negative bacterium, Xenorhabdus (PMID: 19598185). Azolidine Tetrahydropyrrole Tetramethylenimine 1-Azacyclopentane Azacyclopentane FEMA 3523 Pyrrolidine hydrochloride C4H9N 71.12 71.0735 pyrrolidine pyrrolidine 123-75-1 C1CCNC1 InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 RWRDLPDLKQPQOW-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Pyrrolidines Organic compounds Organoheterocyclic compounds Pyrrolidines Aliphatic heteromonocyclic compounds Azacyclic compounds Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Aliphatic heteromonocyclic compound Amine Azacycle Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyrrolidine Secondary aliphatic amine Secondary amine azacycloalkane pyrrolidines saturated organic heteromonocyclic parent melting_point -63 °C boiling_point 87 °C Wikipedia logp 0.16 ALOGPS logs 0.61 ALOGPS logp 0.21 ChemAxon pka_strongest_basic 11.4 ChemAxon iupac pyrrolidine ChemAxon average_mass 71.12 ChemAxon mono_mass 71.0735 ChemAxon smiles C1CCNC1 ChemAxon formula C4H9N ChemAxon inchi InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 ChemAxon inchikey RWRDLPDLKQPQOW-UHFFFAOYSA-N ChemAxon polar_surface_area 12.03 ChemAxon refractivity 22.23 ChemAxon polarizability 8.58 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB007401 29008 33135 31268 VES Pyrrolidine Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Reimer D, Luxenburger E, Brachmann AO, Bode HB: A new type of pyrrolidine biosynthesis is involved in the late steps of xenocoumacin production in Xenorhabdus nematophila. Chembiochem. 2009 Aug 17;10(12):1997-2001. doi: 10.1002/cbic.200900187. 19598185 1.0 2020-03-18 23:24:26 UTC 2020-08-04 22:27:48 UTC CDB000091 Isobutyraldehyde 2-Methylpropanal, also known as isobutanal or isobutylaldehyde, belongs to the class of organic compounds known as short-chain aldehydes. These are aldehydes with a chain length containing between 2 and 5 carbon atoms. 2-Methylpropanal is a clear colorless liquid with an aldehydic, pungent, floral odor. Its odor is also described as that of wet cereal or straw. At very low dilutions it has a pleasant fuirty, banana-like odor. 2-Methylpropanal is found in a number of foods including carrots, coffee beans, maitakes, broad beans, agars, black chokeberries, mustard spinachs, greenthread tea, various wheats, common grapes and oxheart cabbages. 2-Methylpropanal has also been reported to be found in Cannabis sativa (PMID: 6991645, 26657499). 2-Methylpropionaldehyde alpha-Methylpropionaldehyde Isobutanal Isobutylaldehyde Isobutyric aldehyde a-Methylpropionaldehyde Α-methylpropionaldehyde 2-Methyl-1-propanal 2-METHYL-propanal 2-Methyl-propionaldehyde alpha -Methylpropionaldehyde Butyric iso aldehyde FEMA 2220 Iso-butyraldehyde Iso-C3H7CHO Isobutaldehyde Isobutyl aldehy de Isobutyl aldehyde Isobutyral Isobutyraldehyd Isobutyraldehyde Isobutyryl aldehyde Isopropyl aldehyde Isopropyl formaldehyde Isopropylaldehyde Isopropylformaldehyde Methyl propanal Methylpropanal So-butyl aldehyde Valine aldehyde 2-Methylpropanal C4H8O 72.11 72.0575 2-methylpropanal isobutyraldehyde 26140-46-5 CC(C)C=O InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 AMIMRNSIRUDHCM-UHFFFAOYSA-N belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Short-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Organic oxide Short-chain aldehyde an <i>n</i>-alkanal propanals water_solubility 89 mg/mL at 25 °C melting_point -65.9 °C boiling_point 63 °C Wikipedia logp 0.60 ALOGPS logs -0.13 ALOGPS logp 0.86 ChemAxon pka_strongest_acidic 17.85 ChemAxon pka_strongest_basic -7 ChemAxon iupac 2-methylpropanal ChemAxon average_mass 72.11 ChemAxon mono_mass 72.0575 ChemAxon smiles CC(C)C=O ChemAxon formula C4H8O ChemAxon inchi InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 ChemAxon inchikey AMIMRNSIRUDHCM-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 20.92 ChemAxon polarizability 8.24 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003271 C03219 6313 6561 48943 CPD-7000 Isobutyraldehyde Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-18 23:24:28 UTC 2020-08-04 22:27:49 UTC CDB000092 Carvacrol Carvacrol or 5-isopropyl-2-methylphenol is a naturally occurring organic compound classified as an alkylphenol (containing at least one aromatic ring) although biochemically, it is a monoterpenoid synthesized from isoprene units. Carvacrol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Carvacrol has a camphor, spice, and thymol taste with a characteristic pungent, warm odor of oregano. Carvacrol is also found in cannabis plants (PMID: 6991645), Carvacrol is found in highest concentrations in pot marjorams, common thymes, and black walnuts and in lower concentrations in rosemaries, common oregano, and sweet marjorams. Carvacrol was detected in pepper (spice), tamarinds, peppermints, lovages, and sweet basils making carvacrol a potential biomarker for the consumption of these foods. It has been added as a flavoring agent, preservative and fragrance in products. Its bioactivity and toxicological properties have been reviewed (PMID: 24915411). As a constituent of many essential oils, carvocrol was demonstrated to have anti-biofilm and anti-microbial properties (PMID: 30067078) and acts as an anti-viral against the norovirus (PMID: 24779581). 1-Hydroxy-2-methyl-5-isopropylbenzene 1-Methyl-2-hydroxy-4-isopropylbenzene 2-Hydroxy-p-cymene 2-Methyl-5-(1-methylethyl)phenol 2-Methyl-5-isopropylphenol 2-p-Cymenol 3-Isopropyl-6-methylphenol 5-Isopropyl-O-cresol 2-Hydroxy-4-isopropyl-1-methylbenzene 2-Hydroxycymene 2-Methyl-5-(1-methylethyl)-phenol 3-Isopropyl-6-methyl-phenol 5-Isopropyl-2-methyl-phenol 6-Methyl-3-isopropylphenol Antioxine BENZENE,2-hydroxy,4-isopropyl,1-methyl carvacrol Carvacrol Cymenol Cymophenol FEMA 2245 Hydroxy-p-cymene Isopropyl-O-cresol Isothymol Isothymol (=2-isopropyl-4-methyl phenol) Karvakrol Methyl-5-(1-methylethyl)phenol O-Thymol Oxycymol p-Cymen-2-ol p-Cymene-2-ol p-Mentha-1,3,5-trien-2-ol 5-Isopropyl-2-methylphenol C10H14O 150.22 150.1045 2-methyl-5-(propan-2-yl)phenol carvacrol 499-75-2 CC(C)C1=CC(O)=C(C)C=C1 InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 RECUKUPTGUEGMW-UHFFFAOYSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Cumenes Hydrocarbon derivatives Monocyclic monoterpenoids Organooxygen compounds Ortho cresols Phenylpropanes Toluenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Cumene Hydrocarbon derivative Monocyclic benzene moiety Monocyclic monoterpenoid O-cresol Organic oxygen compound Organooxygen compound P-cymene Phenol Phenylpropane Toluene Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids botanical anti-fungal agent p-menthane monoterpenoid phenols water_solubility 1.25 mg/mL at 25 °C logp 3.49 melting_point 3.5 °C boiling_point 237.7 °C Wikipedia logp 3.20 ALOGPS logs -2.50 ALOGPS logp 3.43 ChemAxon pka_strongest_acidic 10.42 ChemAxon pka_strongest_basic -5.5 ChemAxon iupac 2-methyl-5-(propan-2-yl)phenol ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC(C)C1=CC(O)=C(C)C=C1 ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 ChemAxon inchikey RECUKUPTGUEGMW-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 47.27 ChemAxon polarizability 17.88 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014512 10364 21105867 3440 C09840 672 C00000156 Carvacrol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Suntres ZE, Coccimiglio J, Alipour M: The bioactivity and toxicological actions of carvacrol. Crit Rev Food Sci Nutr. 2015;55(3):304-18. doi: 10.1080/10408398.2011.653458. 24915411 Marchese A, Arciola CR, Coppo E, Barbieri R, Barreca D, Chebaibi S, Sobarzo-Sanchez E, Nabavi SF, Nabavi SM, Daglia M: The natural plant compound carvacrol as an antimicrobial and anti-biofilm agent: mechanisms, synergies and bio-inspired anti-infective materials. Biofouling. 2018 Jul;34(6):630-656. doi: 10.1080/08927014.2018.1480756. Epub 2018 Aug 1. 30067078 Gilling DH, Kitajima M, Torrey JR, Bright KR: Antiviral efficacy and mechanisms of action of oregano essential oil and its primary component carvacrol against murine norovirus. J Appl Microbiol. 2014 May;116(5):1149-63. doi: 10.1111/jam.12453. Epub 2014 Feb 12. 24779581 1.0 2020-03-18 23:24:30 UTC 2020-07-07 15:55:10 UTC CDB000093 Piperitenone Piperitenone belongs to the class of organic compounds known as menthane monoterpenoids, with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, piperitenone is an isoprenoid lipid molecule. It is very hydrophobic, almost insoluble in water, and relatively neutral. Piperitenone is a minty, phenolic, and sharp-taste ( http://www.thegoodscentscompany.com/data/rw1031141.html). Piperitenone is found in highest concentrations in spearmints and rosemaries. It was detected in peppermints, herbs and spices, orange mints, citrus, and mentha (mint). This could make piperitenone a potential biomarker for the consumption of these foods. Piperitenone is also found in cannabis plants (PMID: 6991645). 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one 3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ci 3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-one 3-Terpinolenone 6-Isopropylidene-3-methyl-2-cyclohexenone FEMA 3560 Pulespenone C10H14O 150.22 150.1045 3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one piperitenone 491-09-8 CC(C)=C1CCC(C)=CC1=O InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3 HKZQJZIFODOLFR-UHFFFAOYSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Cyclohexenones Hydrocarbon derivatives Monocyclic monoterpenoids O-quinomethanes Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Cyclohexenone Hydrocarbon derivative Ketone Monocyclic monoterpenoid O-quinomethane Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Quinomethane Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids a small molecule p-menthadien-3-one logp 2.39 ALOGPS logs -1.86 ALOGPS logp 2.81 ChemAxon pka_strongest_acidic 18.6 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC(C)=C1CCC(C)=CC1=O ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3 ChemAxon inchikey HKZQJZIFODOLFR-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 47.96 ChemAxon polarizability 17.77 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015974 337757 C01951 17304 381152 C00010889 CPD-278 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:24:32 UTC 2020-08-04 22:27:50 UTC CDB000094 Secoisolariciresinol Secoisolariciresinol belongs to the class of organic compounds known as dibenzylbutanediol lignans, which contain a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is an essentially neutral compound. Its highest known food content (0.3%) is in flaxseed (Linum usitatƒ±ssimum) while the water extract of silver fir wood contains more than 5% secoisolariciresinol (PMID: 15877880). It is also present in nettle brew and cannabis plants (PMID: 6991645). Secoisolariciresinol has been detected in sourdoughs, lindens, savoy cabbages, sugar apples, and common grapes, making secoisolariciresinol a potential biomarker for the consumption of these foods. In the intestine, the gut microflora can form secoisolariciresinol from the secoisolariciresinol diglucoside (also in flaxseed) and it can then be further transformed into the enterolignan enterodiol. Epidemiological studies showed associations between secoisolariciresinol intake and decreased risk of cardiovascular disease (PMID: 29101172).. C20H26O6 362.42 362.1729 (2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol (2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol 29388-59-8 COC1=C(O)C=CC(CC(CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1 InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16+ PUETUDUXMCLALY-IYBDPMFKSA-N belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Dibenzylbutanediol lignans Organic compounds Lignans, neolignans and related compounds Dibenzylbutane lignans Dibenzylbutanediol lignans Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Phenoxy compounds Primary alcohols 1-hydroxy-2-unsubstituted benzenoid Alcohol Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Dibenzylbutanediol Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Primary alcohol logp 2.05 ALOGPS logs -4.48 ALOGPS logp 2.33 ChemAxon pka_strongest_acidic 9.96 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac (2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol ChemAxon average_mass 362.42 ChemAxon mono_mass 362.1729 ChemAxon smiles COC1=C(O)C=CC(CC(CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=C1 ChemAxon formula C20H26O6 ChemAxon inchi InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16+ ChemAxon inchikey PUETUDUXMCLALY-IYBDPMFKSA-N ChemAxon polar_surface_area 99.38 ChemAxon refractivity 99.29 ChemAxon polarizability 38.33 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11552274 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC: Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutr. 2005 Mar;93(3):393-402. doi: 10.1079/bjn20051371. 15877880 Parikh M, Netticadan T, Pierce GN: Flaxseed: its bioactive components and their cardiovascular benefits. Am J Physiol Heart Circ Physiol. 2018 Feb 1;314(2):H146-H159. doi: 10.1152/ajpheart.00400.2017. Epub 2017 Nov 3. 29101172 1.0 2020-03-18 23:24:35 UTC 2020-08-04 22:27:50 UTC CDB000095 Methyl acetate Acetic acid-methyl ester or methyl acetate, also known as devoton, methyl ethanoate or tereton, belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. It is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Specifically methyl acetate has a sweet, fruity, cognac or rum-like aroma and a green, fruity taste. Methyl acetate is a flavouring agent and can be found naturally in many fruits, some of which include apple, grape, banana, orange mint, and ginger. Methyl acetate has also been found in Cannabis sativa (PMID: 6991645, 26657499). It is also used as a perfuming agent in the cosmetic industry. Methyl acetate has characteristics very similar to its analog ethyl acetate. As a result, methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. As an extraction solvent, methyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperatures its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or acids. Methyl acetate is an ester that can be synthesized from acetic acid and methanol in the presence of strong acids such as sulfuric acid in an esterification reaction. In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature. Acetate de methyle Acetic acid methyl ester AcOMe CH3CO2CH3 CH3COOCH3 Devoton MeOAc Methyl ethanoate Methylacetat Tereton Acetic acid de methyle Acetate methyl ester Methyl ethanoic acid Methyl acetic acid Acetic acid, methyl ester Acetic acid,methyl ester Ethyl ester OF monoacetic acid FEMA 2676 HSDB 95 METHYL acetATE, 97% Methyl acetic ester Methyl ester OF acetic acid Methyl-acetate Methylacetaat Methyle (acetate de) Methylester kiseliny octove Metile Metile (acetato di) Octan metylu C3H6O2 74.08 74.0368 methyl acetate methyl acetate 79-20-9 COC(C)=O InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3 KXKVLQRXCPHEJC-UHFFFAOYSA-N belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group. Methyl esters Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Hydrocarbon derivative Methyl ester Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound a small molecule acetate ester methyl ester water_solubility 243 mg/mL at 20 °C logp 0.18 melting_point -98.7 °C boiling_point 56.9 °C Wikipedia logp 0.18 ALOGPS logs 0.54 ALOGPS logp -0.077 ChemAxon pka_strongest_basic -7 ChemAxon iupac methyl acetate ChemAxon average_mass 74.08 ChemAxon mono_mass 74.0368 ChemAxon smiles COC(C)=O ChemAxon formula C3H6O2 ChemAxon inchi InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3 ChemAxon inchikey KXKVLQRXCPHEJC-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 17.41 ChemAxon polarizability 7.36 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008125 C17530 6335 6584 77700 C00048479 METHYL-ACETATE Methyl_acetate Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-18 23:24:37 UTC 2020-08-04 22:27:50 UTC CDB000096 Dihydrocarvone Dihydrocarvone, also known as menth-8-en-2-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Dihydrocarvone is an essentially neutral compound. It has a warm herbal, minty taste with a spicy¬†minty¬†woody¬†camphoreous flavour ( http://www.thegoodscentscompany.com/data/rw1031221.html#toorgano). Dihydrocarvone is found in highest concentrations in spearmints, caraway, and wild celeries and was detected celery stalks, dills, pepper (spice), and peppermints. This could make dihydrocarvone a potential biomarker for the consumption of these foods. Dihydrocarvone is also found in cannabis plants (PMID: 6991645). (2S,5S)-2-Methyl-5-isopropenylcyclohexanone (2S,5S)-5-Isopropenyl-2-methylcyclohexanone (-)-Dihydrocarvone (-)-trans-Dihydrocarvone 1S,4S-Dihydrocarvone C10H16O 152.23 152.1201 (2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one (-)-dihydrocarvone 6909-25-7 C[C@H]1CC[C@@H](CC1=O)C(C)=C InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1 AZOCECCLWFDTAP-IUCAKERBSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Cyclic ketones Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Hydrocarbon derivative Ketone Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Menthane monoterpenoids Menthane monoterpenoids dihydrocarvone logp 2.39 ALOGPS logs -2.43 ALOGPS logp 2.7 ChemAxon pka_strongest_basic -7.4 ChemAxon iupac (2S,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one ChemAxon average_mass 152.23 ChemAxon mono_mass 152.1201 ChemAxon smiles C[C@H]1CC[C@@H](CC1=O)C(C)=C ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1 ChemAxon inchikey AZOCECCLWFDTAP-IUCAKERBSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 46.3 ChemAxon polarizability 18.27 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014916 391455 443183 168 C11415 C00010947 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-18 23:24:39 UTC 2020-06-30 00:14:40 UTC CDB000097 Diethylamine Diethylamine, also known as DEA, is a secondary amine with the molecular structure CH3CH2NHCH2CH3 and belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. It is a colorless liquid that is miscible with water and ethanol. Diethylamine is a strong basic compound. It is volatile with a strong unpleasant odor and an ammoniacal and fishy taste. Diethylamine is found in highest concentrations in barley and apples and has also been detected in common grapes, corn, and spinach leaves. This could make diethylamine a potential biomarker for the consumption of these foods. Diethylamine is also found in cannabis plants (PMID: 6991645). (C2H5)2nh DEA Diaethylamin Et2nh N,N-Diethylamine 5-oxo-L-Prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfO-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamiden-ethylethanamine (1/1) Caerulein diethylamine Ceruletide diethylamine Diethamine Diethylnitrosamine Dietilamina Dwuetyloamina N-Ethylethanamine NDEA Diethylamine hydrobromide Diethylamine acetate Diethylamine hydrochloride Diethylamine sulfate Diethylamine perchlorate Diethylamine sulfite (1:1) Diethylamine phosphate (1:1) C4H11N 73.14 73.0891 diethylamine diethylamine 71247-25-1 CCNCC InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 HPNMFZURTQLUMO-UHFFFAOYSA-N belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dialkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Secondary aliphatic amine secondary aliphatic amine logp 0.657 Wikipedia melting_point -50 °C boiling_point 54.8 - 56.4 °C Wikipedia logp 0.76 ALOGPS logs 0.54 ALOGPS logp 0.52 ChemAxon pka_strongest_basic 10.58 ChemAxon iupac diethylamine ChemAxon average_mass 73.14 ChemAxon mono_mass 73.0891 ChemAxon smiles CCNCC ChemAxon formula C4H11N ChemAxon inchi InChI=1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 ChemAxon inchikey HPNMFZURTQLUMO-UHFFFAOYSA-N ChemAxon polar_surface_area 12.03 ChemAxon refractivity 24.19 ChemAxon polarizability 9.72 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB005767 7730 8021 85259 C14422 DIETHYLAMINE Diethylamine Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:24:42 UTC 2020-08-04 22:27:50 UTC CDB000098 Longifolene Longifolene is a tricyclic sesquiterpene synthesized from isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID: 17467679), in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Longifolene is a colorless to yellow clear oily liquid found in the high-boiling fraction of certain pine resins. The name is derived from the pine species, Pinus longifolia, from which it was isolated. It has a woody,¬†medicinal,¬†pine,¬†ambergris flavor with a sweet¬†woody¬†rose¬†medicinal¬†fir needle odor ( http://www.thegoodscentscompany.com/data/rw1020031.html#toorgano). It is found in mandarin, artichoke, and star anise fruit and in oils from carrot seeds, hinoki leaf, root and wood and pine needle. Longifolene found in rosemary plants and cannabis plants (PMID: 6991645). C15H24 204.36 204.1878 (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0^{2,9}]undecane (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0^{2,9}]undecane 475-20-7 C[C@]12CCCC(C)(C)[C@H]3[C@H](CC[C@@H]13)C2=C InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1 PDSNLYSELAIEBU-GUIRCDHDSA-N boiling_point 254 °C at 706 mmHg Wikipedia logp 4.65 ALOGPS logs -5.21 ALOGPS logp 4.16 ChemAxon iupac (1R,2S,7S,9S)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0^{2,9}]undecane ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@]12CCCC(C)(C)[C@H]3[C@H](CC[C@@H]13)C2=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1 ChemAxon inchikey PDSNLYSELAIEBU-GUIRCDHDSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.62 ChemAxon polarizability 25.42 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 1.0 2020-03-18 23:24:44 UTC 2020-09-11 20:08:25 UTC CDB000099 Camphene Camphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID: 6991645). (+)-Comphene (1R)-2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane (1R,4S)-(+)-Camphene (1R,4S)-2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane (1R,4S)-Camphene D-Camphene (+)-Camphene (1R)-Camphene (±)-Camphene 2,2-Dimethyl-3-methylenenorbornane 2-Methylene-3,3-dimethylbicyclo[2.2.1]heptane 3,3-Dimethyl-2-methylenenorbornane 3,3-Dimethyl-2-methylenenorcamphane dl-Camphene C10H16 136.23 136.1252 (1R,4S)-2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane (+)-camphene 5794-03-6 CC1(C)[C@@H]2CC[C@@H](C2)C1=C InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9+/m0/s1 CRPUJAZIXJMDBK-DTWKUNHWSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bicyclic monoterpenoids Bicyclic monoterpenoids Cyclic monoterpenes camphene melting_point 51 - 52 °C Wikipedia boiling_point 159 °C Wikipedia logp 4.56 ALOGPS logs -3.34 ALOGPS logp 2.86 ChemAxon iupac (1R,4S)-2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC1(C)[C@@H]2CC[C@@H](C2)C1=C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9+/m0/s1 ChemAxon inchikey CRPUJAZIXJMDBK-DTWKUNHWSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.65 ChemAxon polarizability 16.95 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001453 92221 20 C06304 C00000818 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-18 23:24:46 UTC 2020-08-04 22:27:51 UTC CDB000100 Friedelin Friedelin or Friedooleanan-3-one belongs to the class of organic compounds known as triterpenoids. Triterpenoids are terpene molecules that contain 30 carbon atoms and are comprised of six isoprene units. Triterpenes are the most diverse class of secondary metabolites and can be found in all living organisms. The biosynthesis of triterpenes occurs through the mevalonic acid pathway (MVA; PMID: 17467679), mainly in the cytosol. A key intermediate in the biosynthesis of triterpenoids is 2,3-oxidosqualene, which undergoes several cyclization reactions to yield pentacyclic triterpenoids such as friedelin. Friedelin is a neutral compound that is barely soluble in water. It is found in pear and in the leaves of guazuma ulmifolia and apple custard. Friedelin is also found in the roots of the Cannabis plants (PMID: 28826544) and in chicory, apple heartwood, pomegranate stem bark and corn stalk ( http://www.thegoodscentscompany.com/data/rw1247531.html#tooccur). Friedelin, isolated from the leaves of Azima tetracantha Lam, exhibited anti-ulcer potential in an ethanol-induced gastric ulcer model (PMID: 25617794). Seven compounds, including friedelin, were isolated from crude extracts of leaves, stems and roots of Alchornea cordifolia (Schumach. and Thonn.) M√ºll. Arg. All compounds had antibacterial activity against pathogens of the gastrointestinal, skin, respiratory and urinary tract (PMID: 26724423). C30H50O 426.73 426.3862 (4S,4aR,6aS,6bS,8aS,12aS,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one (4S,4aR,6aS,6bS,8aS,12aS,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1H-picen-3-one 559-74-0 C[C@@H]1C(=O)CC[C@@H]2[C@@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@H]3CC(C)(C)CC[C@@]3(C)CC[C@@]12C InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22-,23+,24+,26+,27+,28+,29+,30+/m1/s1 OFMXGFHWLZPCFL-VVWBYUDUSA-N logp 6.66 ALOGPS logs -7.15 ALOGPS logp 8.12 ChemAxon pka_strongest_basic -7.4 ChemAxon iupac (4S,4aR,6aS,6bS,8aS,12aS,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-one ChemAxon average_mass 426.73 ChemAxon mono_mass 426.3862 ChemAxon smiles C[C@@H]1C(=O)CC[C@@H]2[C@@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@H]3CC(C)(C)CC[C@@]3(C)CC[C@@]12C ChemAxon formula C30H50O ChemAxon inchi InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22-,23+,24+,26+,27+,28+,29+,30+/m1/s1 ChemAxon inchikey OFMXGFHWLZPCFL-VVWBYUDUSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 130.21 ChemAxon polarizability 53.38 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Russo EB, Marcu J: Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads. Adv Pharmacol. 2017;80:67-134. doi: 10.1016/bs.apha.2017.03.004. Epub 2017 Jun 5. 28826544 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Antonisamy P, Duraipandiyan V, Aravinthan A, Al-Dhabi NA, Ignacimuthu S, Choi KC, Kim JH: Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms. Eur J Pharmacol. 2015 Mar 5;750:167-75. doi: 10.1016/j.ejphar.2015.01.015. Epub 2015 Jan 22. 25617794 Noundou XS, Krause RW, van Vuuren SF, Ndinteh DT, Olivier DK: Antibacterial effects of Alchornea cordifolia (Schumach. and Thonn.) Mull. Arg extracts and compounds on gastrointestinal, skin, respiratory and urinary tract pathogens. J Ethnopharmacol. 2016 Feb 17;179:76-82. doi: 10.1016/j.jep.2015.12.043. Epub 2015 Dec 24. 26724423 1.0 2020-03-18 23:24:48 UTC 2020-08-04 22:27:51 UTC CDB000101 Galactose Galactose, also known as galactopyranose, is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-galactose are important not only for the provision of these pathways but also for the prevention of D-galactose metabolite accumulation. The main source of D-galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-galactose-1-phosphate. In the presence of D-galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-galactose-1-phosphate. Classic galactosemia, a term that denotes the presence of D-galactose in the blood, is the rare inborn error of D-galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene (PMID: 15256214¬†, 11020650¬†, 10408771¬†). Galactose in the urine is a biomarker for the consumption of milk. Galactose is a monosaccharid found in cannabis plants (PMID: 6991645). (2R,3S,4S,5R)-2,3,4,5,6-Pentahydroxyhexanal Galactopyranose D Galactose D-Galactose Galactopyranoside C6H12O6 180.16 180.0634 (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal aldehydo-D-galactose 59-23-4 OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6-/m0/s1 GZCGUPFRVQAUEE-KCDKBNATSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha-hydroxyaldehydes Beta-hydroxy aldehydes Hydrocarbon derivatives Medium-chain aldehydes Organic oxides Polyols Primary alcohols Secondary alcohols Alcohol Aldehyde Aliphatic acyclic compound Alpha-hydroxyaldehyde Beta-hydroxy aldehyde Carbonyl group Hexose monosaccharide Hydrocarbon derivative Medium-chain aldehyde Organic oxide Polyol Primary alcohol Secondary alcohol D-galactose aldehydo-galactose water_solubility 650 g/L Wikipedia melting_point 168–170 °C Wikipedia logp -2.41 ALOGPS logs 0.16 ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 12.26 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6-/m0/s1 ChemAxon inchikey GZCGUPFRVQAUEE-KCDKBNATSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 37.35 ChemAxon polarizability 16.13 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 3037556 17118 C01582 DB11735 C00019681 Galactose Lai K, Klapa MI: Alternative pathways of galactose assimilation: could inverse metabolic engineering provide an alternative to galactosemic patients? Metab Eng. 2004 Jul;6(3):239-44. doi: 10.1016/j.ymben.2004.01.001. 15256214 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:24:51 UTC 2020-08-04 22:27:52 UTC CDB000102 Humulene alpha-humulene also known as Humulene or alpha-caryophyllene is a volatile organic compound that belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP; PMID:23746261) pathway in the cytoplasm. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Humulene is is a pale yellowish green clear liquid, soluble in alcohol that is barely soluble in water. It has a woody odor and adds a woody, oceanic-watery, spicy-clove note to perfumes ( http://www.thegoodscentscompany.com/data/rw1027221.html#tooccur). It contributes to the characteristic aroma of¬†Cannabis¬†(PMID: 6991645) and to the taste of the spice¬†Persicaria odorata¬†or¬†Vietnamese coriander. Humulene is found in hops (Humulus lupulus; doi:10.1055/s-2006-962205), from which its name was derived. It is often found together with its isomer beta-caryophyllene in many other aromatic plants such pine trees ( PMID: 17396639),¬†orange trees,¬†marsh elders,¬†tobacco,¬† sunflowers,¬†Salvia officinalis¬†(common sage, culinary sage),¬†Lindera strychnifolia¬†Uyaku (Japanese spicebush, ginseng¬†species and the Zingiberaceae (the ginger family). alpha-Humulene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). alpha-humulene, a very reactive volatile organic compound emitted by many organic plants, quickly combines with ozone in sunlight (photooxidation) to create secondary organic aerosols ( oi:10.1039/c0cp02379e). alpha-humulene has antibacterial and anti-biofilm properties against Bacteroides fragilis (PMID: 32073898) and demonstrated anti-inflammatory properties in an ovalbumin-induced model of airway allergic inflammation (PMID: 19438512).¬† a-Humulene Α-humulene (1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene (1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4,8-triene (1E,4E,8E)-alpha-Humulene (1E,4E,8E)-Humula-1(11),4,8-triene (e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-(1E,4E,8E)-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-(e,e,e)-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-cycloundeca-1,4,8-triene 3,7,10-Humulatriene a-Caryophyllene (obsol.) alpha -Humulen alpha -Humulene alpha -Humulene (alpha -caryophyllene) alpha -Humulenen alpha-Caryophyllene Humulene alpha-Humulene C15H24 204.35 204.1878 (1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene humulene 6753-98-6 C\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1 InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6-,13-7-,14-10- FAMPSKZZVDUYOS-KXWHQPPKSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Humulane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon melting_point < 25 °C boiling_point 106 - 107 °C at 5 mmHg Wikipedia logp 6.07 ALOGPS logs -4.28 ALOGPS logp 4.88 ChemAxon iupac (1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6-,13-7-,14-10- ChemAxon inchikey FAMPSKZZVDUYOS-KXWHQPPKSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.55 ChemAxon polarizability 26.18 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015360 5006149 6508206 C09684 C00003147 Humulene 5768 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 Helmig D, Ortega J, Duhl T, Tanner D, Guenther A, Harley P, Wiedinmyer C, Milford J, Sakulyanontvittaya T: Sesquiterpene emissions from pine trees--identifications, emission rates and flux estimates for the contiguous United States. Environ Sci Technol. 2007 Mar 1;41(5):1545-53. doi: 10.1021/es0618907. 17396639 Jang HI, Rhee KJ, Eom YB: Antibacterial and antibiofilm effects of alpha-humulene against Bacteroides fragilis. Can J Microbiol. 2020 Jun;66(6):389-399. doi: 10.1139/cjm-2020-0004. Epub 2020 Feb 19. 32073898 Rogerio AP, Andrade EL, Leite DF, Figueiredo CP, Calixto JB: Preventive and therapeutic anti-inflammatory properties of the sesquiterpene alpha-humulene in experimental airways allergic inflammation. Br J Pharmacol. 2009 Oct;158(4):1074-87. doi: 10.1111/j.1476-5381.2009.00177.x. Epub 2009 May 8. 19438512 1.0 2020-03-18 23:24:53 UTC 2020-08-04 22:27:54 UTC CDB000103 Sativic acid Sativic acid, also known as sativate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Fatty acid biosynthesis occurs through the acetate pathway and the process is catalyzed by the Fatty Acid Synthase (FAS; PMID: 12689621). Structurally, two types of FAS exist, with Type 1, a multifunctional large polypeptide found in animals and fungi and with Type 2, consisting of monofunctional enzymes found in archae and bacteria (PMID: 25360565). Sativic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Sativic acid is one of the fatty acids that are known to occur in Cannabis sativa (PMID: 6991645). Sativic acid can also be found in rice, which makes sativic acid a potential biomarker for the consumption of this food product. (9S,10S,12R,13R)-9,10,12,13-Tetrahydroxyoctadecanoate C18H36O6 348.48 348.2512 (9S,10S,12R,13R)-9,10,12,13-tetrahydroxyoctadecanoic acid (9S,10S,12R,13R)-9,10,12,13-tetrahydroxyoctadecanoic acid 541-82-2 CCCCC[C@@H](O)[C@H](O)C[C@H](O)[C@@H](O)CCCCCCCC(O)=O InChI=1S/C18H36O6/c1-2-3-7-10-14(19)16(21)13-17(22)15(20)11-8-5-4-6-9-12-18(23)24/h14-17,19-22H,2-13H2,1H3,(H,23,24)/t14-,15+,16-,17+/m1/s1 VJOGZGLNDROOFS-TWMKSMIVSA-N logp 2.45 ALOGPS logs -2.67 ALOGPS logp 2.15 ChemAxon pka_strongest_acidic 4.62 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (9S,10S,12R,13R)-9,10,12,13-tetrahydroxyoctadecanoic acid ChemAxon average_mass 348.48 ChemAxon mono_mass 348.2512 ChemAxon smiles CCCCC[C@@H](O)[C@H](O)C[C@H](O)[C@@H](O)CCCCCCCC(O)=O ChemAxon formula C18H36O6 ChemAxon inchi InChI=1S/C18H36O6/c1-2-3-7-10-14(19)16(21)13-17(22)15(20)11-8-5-4-6-9-12-18(23)24/h14-17,19-22H,2-13H2,1H3,(H,23,24)/t14-,15+,16-,17+/m1/s1 ChemAxon inchikey VJOGZGLNDROOFS-TWMKSMIVSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 92.3 ChemAxon polarizability 41.29 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Smith S, Witkowski A, Joshi AK: Structural and functional organization of the animal fatty acid synthase. Prog Lipid Res. 2003 Jul;42(4):289-317. doi: 10.1016/s0163-7827(02)00067-x. 12689621 Beld J, Lee DJ, Burkart MD: Fatty acid biosynthesis revisited: structure elucidation and metabolic engineering. Mol Biosyst. 2015 Jan;11(1):38-59. doi: 10.1039/c4mb00443d. Epub 2014 Oct 31. 25360565 1.0 2020-03-18 23:24:55 UTC 2020-08-04 22:27:55 UTC CDB000104 Orientin Orientin, also known as lutexin, is an 8-C-glycosilated derivative of the flavonoid luteolin, substituted by beta-D-glucopyranosyl. Flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C; also shared by the tocopherols), with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. 8-C-glycosilated flavonoids are compounds containing a carbohydrate moiety which is C-glycosidically linked to position 8 of a 2-phenylchromen-4-one flavonoid backbone. Orientin is a neutral compound. Orientin is a water-soluble flavonoid C-glycoside found in calcium tree, black bamboo, spelts, triticales, red rices, hard wheats, flaxseeds, wild apricot and cucumber; in barley, flax and tamarind leaves; in basil, blueberry, oregano plants; passion flower, the¬†A√ßa√≠ palm,¬†buckwheat¬†sprouts,¬†and in¬†millets. It is one of several dozen flavonoid glycosides that have been identified in low-THC Cannabis cultivars (PMID: 6991645). Flavonoids are polyphenolic compounds that are universally present as constituents of flowering plants, particularly of food plants. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. Orientin, extracted from different medicinal plants, exhibits antioxidant, anti-aging, anti-viral, anti-bacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, anti-adipogenesis, and anti-nociceptive effects that have been reviewed (PMID: 27298620). 8-beta-D-Glucosylluteolin Luteolin 8-C-glucoside Lutexin 8-b-D-Glucosylluteolin 8-Β-D-glucosylluteolin 8-C-beta-Glucopyranosyl-3',4',5,7-tetrahydroxyflav-2-en-3-one C21H20O11 448.38 448.1006 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one orientin 28608-75-5 OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1 InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1 PLAPMLGJVGLZOV-VPRICQMDSA-N belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Flavonoid 8-C-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives C-glycosyl compounds Catechols Chromones Dialkyl ethers Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran C-glycosyl compound Catechol Chromone Dialkyl ether Ether Flavone Flavonoid-8-c-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Monosaccharide Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid 3'-hydroxyflavonoid C-glycosyl compound Flavones and Flavonols flavones tetrahydroxyflavone logp 0.34 ALOGPS logs -2.31 ALOGPS logp -0.35 ChemAxon pka_strongest_acidic 6.17 ChemAxon pka_strongest_basic -3 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one ChemAxon average_mass 448.38 ChemAxon mono_mass 448.1006 ChemAxon smiles OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1 ChemAxon formula C21H20O11 ChemAxon inchi InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1 ChemAxon inchikey PLAPMLGJVGLZOV-VPRICQMDSA-N ChemAxon polar_surface_area 197.37 ChemAxon refractivity 108.01 ChemAxon polarizability 42.38 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C10114 5281675 7781 C00001078 Orientin Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Lam KY, Ling AP, Koh RY, Wong YP, Say YH: A Review on Medicinal Properties of Orientin. Adv Pharmacol Sci. 2016;2016:4104595. doi: 10.1155/2016/4104595. Epub 2016 May 19. 27298620 1.0 2020-03-18 23:24:57 UTC 2020-09-11 20:08:56 UTC CDB000105 Proline Proline or L-proline abbreviated Pro or is one of the twenty amino acids used in living organisms as the building blocks of proteins. Proline is sometimes called an imino acid, although the IUPAC definition of an imine requires a carbon-nitrogen double bond. Proline is a non-essential amino acid that is largely synthesized from glutamic acid. While proline biosynthetic pathways exist from eubacteria to eukaryotes, in the most prevalent pathway, proline is cyclized from glutamate. First glutamate is phosphorylated to gamma-glutamyl phosphate by gamma-glutamyl kinase, then second, reduced to gamma-glutamyl semialdehyde by gamma-glutamyl phosphate reductase, then third, cyclized spontaneously to delta(1)-pyrroline-5-carboxylate and fourth, reduced to proline by delta(1)-pyrroline-5-carboxylate reductase. In higher plants and animals, the first two steps are catalysed by a bi-functional delta(1) -pyrroline-5-carboxylate synthase. Alternative pathways of proline formation use the initial steps of the arginine biosynthetic pathway to ornithine, which can be converted to delta(1)-pyrroline-5-carboxylate by ornithine aminotransferase and then reduced to proline or converted directly to proline by ornithine cyclodeaminase (PMID: 25367752). Proline is an essential component of collagen and is important for proper functioning of joints and tendons. L-proline has acted as a weak agonist of the glycine receptor and of both NMDA and non-NMDA ionotropic glutamate receptors (PMID:1349155). It is a potential endogenous excitotoxin/neurotoxin, which causes damage to nerve cells and nerve tissues. Proline, when injected into the brains of rats, non-selectively destroyed pyramidal and granule cells (PMID: 3409032) suggesting that it can act as a neurotoxin. Proline can also be a metabotoxin which is an endogenously produced metabolite that causes adverse health effects at chronically high levels. At least five inborn errors of metabolism, including hyperprolinemia type I, hyperprolinemia type II, iminoglycinuria, prolinemia type II, and pyruvate carboxylase deficiency are associated with chronically high levels of proline (PMID: 18806117). While most people with hyperprolinemia type I often do not show any symptoms despite proline blood levels being between 3 and 10 times the normal level, some individuals have seizures, intellectual disability, or other neurological or psychiatric problems. Hyperprolinemia type II patients have proline blood levels between 10 and 15 times higher than normal, and high levels of a related compound called pyrroline-5-carboxylate. While Hyperprolinemia type II patients have signs and symptoms that vary in severity, they are more likely than type I patients to have seizures or intellectual disability. Hyperprolinemia I and II are caused by deficiencies in the enzymatic activities of proline dehydrogenase and Delta-1-pyrroline-5-carboxylate reductase, respectively. Proline is also found in Cannabis plants (PMID: 6991645). (-)-(S)-Proline (-)-2-Pyrrolidinecarboxylic acid (-)-Proline (2S)-Pyrrolidine-2-carboxylic acid (S)-2-Carboxypyrrolidine (S)-2-Pyrrolidinecarboxylic acid (S)-Pyrrolidine-2-carboxylic acid 2-Pyrrolidinecarboxylic acid L-(-)-Proline L-alpha-Pyrrolidinecarboxylic acid L-Prolin L-Pyrrolidine-2-carboxylic acid P Prolina PROLINE Prolinum (-)-2-Pyrrolidinecarboxylate (2S)-Pyrrolidine-2-carboxylate (S)-2-Pyrrolidinecarboxylate (S)-Pyrrolidine-2-carboxylate 2-Pyrrolidinecarboxylate L-a-Pyrrolidinecarboxylate L-a-Pyrrolidinecarboxylic acid L-alpha-Pyrrolidinecarboxylate L-Α-pyrrolidinecarboxylate L-Α-pyrrolidinecarboxylic acid L-Pyrrolidine-2-carboxylate (S)-(-)-Proline (S)-(-)-Pyrrolidine-2-carboxylate (S)-(-)-Pyrrolidine-2-carboxylic acid (S)-2-Pyrralidinecarboxylate (S)-2-Pyrralidinecarboxylic acid (S)-Proline L Proline C5H9NO2 115.13 115.0633 (2S)-pyrrolidine-2-carboxylic acid L-proline 147-85-3 OC(=O)[C@@H]1CCCN1 InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 ONIBWKKTOPOVIA-BYPYZUCNSA-N belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Proline and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic heteromonocyclic compounds Amino acids Azacyclic compounds Carbonyl compounds Carboxylic acids Dialkylamines Hydrocarbon derivatives L-alpha-amino acids Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Pyrrolidine carboxylic acids Aliphatic heteromonocyclic compound Alpha-amino acid Amine Amino acid Azacycle Carbonyl group Carboxylic acid Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Proline or derivatives Pyrrolidine Pyrrolidine carboxylic acid Pyrrolidine carboxylic acid or derivatives Secondary aliphatic amine Secondary amine Common amino acids L-alpha-amino acid glutamine family amino acid proline proteinogenic amino acid water_solubility 162.0 mg/mL logp -2.54 HANSCH,C ET AL. (1995) melting_point 221 °C logp -2.71 ALOGPS logs 0.50 ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 1.94 ChemAxon pka_strongest_basic 11.33 ChemAxon iupac (2S)-pyrrolidine-2-carboxylic acid ChemAxon average_mass 115.13 ChemAxon mono_mass 115.0633 ChemAxon smiles OC(=O)[C@@H]1CCCN1 ChemAxon formula C5H9NO2 ChemAxon inchi InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1 ChemAxon inchikey ONIBWKKTOPOVIA-BYPYZUCNSA-N ChemAxon polar_surface_area 49.33 ChemAxon refractivity 28.06 ChemAxon polarizability 11.5 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00148 DB00172 FDB000570 128566 145742 17203 PRO C00001388 L-proline 34042 29 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Henzi V, Reichling DB, Helm SW, MacDermott AB: L-proline activates glutamate and glycine receptors in cultured rat dorsal horn neurons. Mol Pharmacol. 1992 Apr;41(4):793-801. 1349155 Fichman Y, Gerdes SY, Kovacs H, Szabados L, Zilberstein A, Csonka LN: Evolution of proline biosynthesis: enzymology, bioinformatics, genetics, and transcriptional regulation. Biol Rev Camb Philos Soc. 2015 Nov;90(4):1065-99. doi: 10.1111/brv.12146. Epub 2014 Nov 4. 25367752 Nadler JV, Wang A, Hakim A: Toxicity of L-proline toward rat hippocampal neurons. Brain Res. 1988 Jul 19;456(1):168-72. doi: 10.1016/0006-8993(88)90358-7. 3409032 Mitsubuchi H, Nakamura K, Matsumoto S, Endo F: Inborn errors of proline metabolism. J Nutr. 2008 Oct;138(10):2016S-2020S. doi: 10.1093/jn/138.10.2016S. 18806117 1.0 2020-03-18 23:24:59 UTC 2020-08-04 22:27:56 UTC CDB000106 Hexatriacontane Hexatriacontane, also known as CH3-[CH2]34-CH3, belongs to the class of organic compounds known as alkanes and has 36 carbons in its unbranched acyclic structure. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Hexatriacontane is possibly neutral. Hexatracontane occurs in three polymorphic crystal forms. Form I melts at 76 ¬∞C with an enthalpy of fusion of 88.74 kJ¬∑mol‚àí1. Two solid phase transitions precede the melting point. At 72 ¬∞C the conversion of Form III to Form II takes place, at 74 ¬∞C the conversion from Form II to Form I. At room temperature, crystal form III is the thermodynamically stable form. The compound can occur in monoclinic crystal lattices for Forms II and III and an orthorhombic crystal lattice for Form I. Recently, the presence of hexatriacontane in methanolic extracts from Achyranthes aspera has been related to an increased antidepressant activity in a Forced Swim and Tail suspension test in mice (PMID: 29256630), by raising cortical and hippocampal monoamine levels. Hexatriacontane is also found in cannabis plants (PMID: 6991645). CH3-[CH2]34-CH3 N-Hexatriacontane C36H74 506.97 506.5791 hexatriacontane hexatriacontane 2040-92-8 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C36H74/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-36H2,1-2H3 YDLYQMBWCWFRAI-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane long-chain alkane logp 11.22 ALOGPS logs -8.03 ALOGPS logp 16.47 ChemAxon iupac hexatriacontane ChemAxon average_mass 506.97 ChemAxon mono_mass 506.5791 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C36H74 ChemAxon inchi InChI=1S/C36H74/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-36H2,1-2H3 ChemAxon inchikey YDLYQMBWCWFRAI-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 167.44 ChemAxon polarizability 76.3 ChemAxon rotatable_bond_count 33 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12412 72688 Higher alkanes Goel RK, Gawande DY, Lagunin AA, Poroikov VV: Pharmacological repositioning of Achyranthes aspera as an antidepressant using pharmacoinformatic tools PASS and PharmaExpert: a case study with wet lab validation. SAR QSAR Environ Res. 2018 Jan;29(1):69-81. doi: 10.1080/1062936X.2017.1408683. Epub 2017 Dec 19. 29256630 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:02 UTC 2020-08-04 22:27:56 UTC CDB000107 Quinic acid Quinic acid, also known as quinate, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3, 4, and 5, as well as a carboxylic acid at position 1. It is also a cyclic polyol and a sugar acid. Quinic acid is a colorless solid that is neutral. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. It contributes to the perceived acidity of coffee and therefore is found in coffee beans as well as in cinchona bark, tobacco leaves, carrot leaves, apples, peaches, pears, plums and vegetables. Quinic acid is one of the acids that have been identified in cannabis plant (PMID: 6991645). Chinic acid D-Quinic acid Kinic acid Quinic acid Chinate D-Quinate Kinate (-)-Quinic acid (-)-Quinate (1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid (1α,3R,4α,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid D-(-)-Quinic acid Hexahydro-1,3,4,5-tetrahydroxybenzoic acid C7H12O6 192.17 192.0634 (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid (-)-quinic acid 77-95-2 O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 AAWZDTNXLSGCEK-WYWMIBKRSA-N belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Quinic acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Alpha hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Cyclohexanols Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Polyols Tertiary alcohols Aliphatic homomonocyclic compound Alpha-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclohexanol Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Organic oxide Polyol Quinic acid Secondary alcohol Tertiary alcohol quinic acid water_solubility 290 mg/mL at 9 °C logp 1.19 RADZICKA,A & WOLFENDEN,R (1988) melting_point 162.5 °C logp -2.46 ALOGPS logs 0.60 ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 3.46 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid ChemAxon average_mass 192.17 ChemAxon mono_mass 192.0634 ChemAxon smiles O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O ChemAxon formula C7H12O6 ChemAxon inchi InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1 ChemAxon inchikey AAWZDTNXLSGCEK-WYWMIBKRSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 39.71 ChemAxon polarizability 17.02 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10246715 6508 C00296 17521 C00001201 QUINATE Quinic_acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:04 UTC 2020-08-04 22:27:56 UTC CDB000108 alpha-Curcumene Alpha-curcumene, or 2-methyl-6-p-tolyl-2-heptene, also known as ar-curcumene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytoplasm. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-curcumene is possibly neutral. It has an herbal ordor. Alpha-curcumene has been detected in anise and carrot seeds, ginger and turmeric rhizomes and rhizome oils, and black pepper fruit and seeds and oils ( http://www.thegoodscentscompany.com/data/rw1053941.html#touses). It is also a component of Cannabis sativa (PMID: 6991645). C15H22 202.34 202.1722 1-methyl-4-[(2S)-6-methylhept-5-en-2-yl]benzene α-curcumene 4176-06-1 C[C@@H](CCC=C(C)C)C1=CC=C(C)C=C1 InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m0/s1 VMYXUZSZMNBRCN-AWEZNQCLSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aromatic homomonocyclic compounds Aromatic hydrocarbons Aromatic monoterpenoids Branched unsaturated hydrocarbons Cyclic olefins Toluenes Aromatic homomonocyclic compound Aromatic hydrocarbon Benzenoid Bisabolane sesquiterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Monocyclic benzene moiety Olefin P-cymene Sesquiterpenoid Toluene Unsaturated hydrocarbon Bisabolane sesquiterpenoids logp 6.15 ALOGPS logs -5.31 ALOGPS logp 5.39 ChemAxon iupac 1-methyl-4-[(2S)-6-methylhept-5-en-2-yl]benzene ChemAxon average_mass 202.34 ChemAxon mono_mass 202.1722 ChemAxon smiles C[C@@H](CCC=C(C)C)C1=CC=C(C)C=C1 ChemAxon formula C15H22 ChemAxon inchi InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m0/s1 ChemAxon inchikey VMYXUZSZMNBRCN-AWEZNQCLSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 69.09 ChemAxon polarizability 26.11 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001523 3083834 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:25:06 UTC 2020-08-04 22:27:56 UTC CDB000109 alpha-Cubebene Alpha-cubebene, also known as cubebene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytoplasm. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements..Alpha-Cubebene is one of the two Cubebene isomers, Œ±- and Œ≤-cubebene, both with the molecular formula C15H24, but differ only in the position of a double bond which is endocyclic (part of the five-membered ring) in Œ±-cubebene and exocyclic in Œ≤-cubebene. It was first isolated from Piper cubeba berries, known as cubebs, from which the name was derived. The volatile oil distilled from cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor (consisting of both Œ±- and Œ≤-cubebene). In addition to cubeb berries, alpha-cubebene is also found in clove buds, fruit and seeds, cypress, lemon, lime, rosemary and tea tree oils and mandarins and oranges ( http://www.thegoodscentscompany.com/data/rw1054531.html#tooccur). Alpha-Cubebene is one of many terpenoids that are found in Cannabis plants (PMID: 6991645). alpha-Cubebene (-)-alpha-Cubebene (-)-α-Cubebene alpha-Cubenene α-Cubenene C15H24 204.36 204.1878 (1R,5S,6R,7S,10R)-4,10-dimethyl-7-(propan-2-yl)tricyclo[4.4.0.0^{1,5}]dec-3-ene (1R,5S,6R,7S,10R)-7-isopropyl-4,10-dimethyltricyclo[4.4.0.0^{1,5}]dec-3-ene 17699-14-8 CC(C)[C@@H]1CC[C@@H](C)[C@@]23CC=C(C)[C@@H]2[C@@H]13 InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h7,9,11-14H,5-6,8H2,1-4H3/t11-,12+,13-,14-,15+/m1/s1 XUEHVOLRMXNRKQ-KHMAMNHCSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cubebane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cubebane and ivaxillarane sesquiterpenoids Sesquiterpenoids (C15) sesquiterpenoid logp 3.88 ALOGPS logs -5.05 ALOGPS logp 4.09 ChemAxon iupac (1R,5S,6R,7S,10R)-4,10-dimethyl-7-(propan-2-yl)tricyclo[4.4.0.0^{1,5}]dec-3-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@@H]1CC[C@@H](C)[C@@]23CC=C(C)[C@@H]2[C@@H]13 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h7,9,11-14H,5-6,8H2,1-4H3/t11-,12+,13-,14-,15+/m1/s1 ChemAxon inchikey XUEHVOLRMXNRKQ-KHMAMNHCSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.77 ChemAxon polarizability 26.16 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 442359 C09647 C00003120 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:25:09 UTC 2020-08-04 22:27:56 UTC CDB000110 BORNYL acetATE Bornyl acetate¬†, also known as isobornyl acetate and pichtosin, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing two fused rings. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Bornyl acetate is the acetylated derivative of borneol. Bornyl acetate is a neutral compound. It is found in spike lavender, coriander, carrot, pine needle, rosemary, sage and valerian root ( http://www.thegoodscentscompany.com/data/rw1007342.html#tooccur). Borneol is used in traditional Chinese medicine. It is a component of several plant essential oils and it is considered a natural repellent against the storage insects Liposcelis bostrychophila and Tribolium castaneum (PMID: 30972667). Bornyl acetate is also present in trace amount in cannabis plants (PMID: 6991645). (1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl acetic acid Isobornyl acetate Pichtosin C12H20O2 196.29 196.1463 (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate 125-12-2 CC(=O)O[C@@H]1C[C@H]2CC[C@]1(C)C2(C)C InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10-,12+/m1/s1 KGEKLUUHTZCSIP-FOGDFJRCSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homopolycyclic compound Bicyclic monoterpenoid Bornane monoterpenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 3.50 ALOGPS logs -3.51 ALOGPS logp 2.43 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate ChemAxon average_mass 196.29 ChemAxon mono_mass 196.1463 ChemAxon smiles CC(=O)O[C@@H]1C[C@H]2CC[C@]1(C)C2(C)C ChemAxon formula C12H20O2 ChemAxon inchi InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10-,12+/m1/s1 ChemAxon inchikey KGEKLUUHTZCSIP-FOGDFJRCSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 54.47 ChemAxon polarizability 22.57 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 637531 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Feng YX, Wang Y, Chen ZY, Guo SS, You CX, Du SS: Efficacy of bornyl acetate and camphene from Valeriana officinalis essential oil against two storage insects. Environ Sci Pollut Res Int. 2019 Jun;26(16):16157-16165. doi: 10.1007/s11356-019-05035-y. Epub 2019 Apr 10. 30972667 1.0 2020-03-18 23:25:11 UTC 2020-08-04 22:27:57 UTC CDB000111 Stigmasta-4,22-dien-3-one Stigmasta-4,22-dien-3-one or 4,22-Cholestadien-24-ethyl-3-one belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. The biosynthesis of sterols shares several steps with that of triterpenes and it occurs through the mevalonic acid pathway (MVA; PMID:17467679), located mainly in the cytoplasm. A key intermediate in the biosynthesis of sterols is 2,3-oxidosqualene, which undergoes several cyclization reactions to yield the tetracyclic structure typical of the stigmastane skeleton. Stigmasta-4,22-dien-3-one is a neutral compound. Stigmasta-4,22-dien-3-one is one of a small number of phytosteroids (including sitosterol, campesterol, and stigmasterol) that are found in cannabis plants (PMID: 6991645). Seven compounds, including stigmasta-4,22-dien-3-one, were isolated from crude extracts of the leaves, stems and roots of Alchornea cordifolia (Schumach. and Thonn.) M√ºll. Arg. All compounds had antibacterial activity against pathogens of the gastrointestinal, skin, respiratory and urinary tract (PMID: 26724423). C29H46O 410.69 410.3549 (1R,2R,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1R,2R,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 20817-72-5 CC[C@H](C=C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,18-21,24-27H,7,10-17H2,1-6H3/t20-,21-,24+,25-,26+,27-,28+,29-/m1/s1 MKGZDUKUQPPHFM-MEVQFFCQSA-N logp 6.47 ALOGPS logs -7.35 ALOGPS logp 8.05 ChemAxon pka_strongest_acidic 19.09 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac (1R,2R,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one ChemAxon average_mass 410.69 ChemAxon mono_mass 410.3549 ChemAxon smiles CC[C@H](C=C[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C ChemAxon formula C29H46O ChemAxon inchi InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,18-21,24-27H,7,10-17H2,1-6H3/t20-,21-,24+,25-,26+,27-,28+,29-/m1/s1 ChemAxon inchikey MKGZDUKUQPPHFM-MEVQFFCQSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 129.83 ChemAxon polarizability 51.69 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 126969962 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Noundou XS, Krause RW, van Vuuren SF, Ndinteh DT, Olivier DK: Antibacterial effects of Alchornea cordifolia (Schumach. and Thonn.) Mull. Arg extracts and compounds on gastrointestinal, skin, respiratory and urinary tract pathogens. J Ethnopharmacol. 2016 Feb 17;179:76-82. doi: 10.1016/j.jep.2015.12.043. Epub 2015 Dec 24. 26724423 1.0 2020-03-18 23:25:13 UTC 2020-07-24 23:30:05 UTC CDB000112 3-[2-(3-Hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol Gigantol also known as 3,3'-dihydroxy-5,4'-dimethoxy bibenzyl, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenoids were first detected and isolated from the stems of cannabis plants in 1982, from cannabis leaves in 1978 and from cannabis resin in 1986 (https://doi.org/10.1007/s11101-008-9094-4). Gigantol is a hydrophobic, neutral compound that is insoluble in water. Gigantol is a derivative of bibenzyl bearing 2 hydroxy and 2 methoxy functional groups positioned on the benzene ring. Bibenzyl is a compound consisting to two benzene rings linked together via ethane. Bibenzyls typically form a white solid. Bibenzyl forms the central core of several natural products such as dihydrostilbenoids and isoquinoline alkaloids. Gigantol has been shown to inhibit cancer migration (PMID: 24844664). Gigantol also exhibits anti-inflammatory, antioxidant and antinociceptive activities. Gigantol is one of small number of bibenzyls including 3,4'-dihydroxy-5-methoxybibenzyl and 3,4'-dihydroxy-5,3'-dimethoxy-5'-isoprenyl bibenzyl found in Cannabis sativa (https://doi.org/10.1007/s11101-008-9094-4). C16H18O4 274.32 274.1205 3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol 3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol 67884-30-4 COC1=CC(CCC2=CC(O)=C(OC)C=C2)=CC(O)=C1 InChI=1S/C16H18O4/c1-19-14-8-12(7-13(17)10-14)4-3-11-5-6-16(20-2)15(18)9-11/h5-10,17-18H,3-4H2,1-2H3 SDXKZPQOVUDXIY-UHFFFAOYSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Stilbene logp 3.07 ALOGPS logs -3.79 ALOGPS logp 3.59 ChemAxon pka_strongest_acidic 9.45 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 3-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5-methoxyphenol ChemAxon average_mass 274.32 ChemAxon mono_mass 274.1205 ChemAxon smiles COC1=CC(CCC2=CC(O)=C(OC)C=C2)=CC(O)=C1 ChemAxon formula C16H18O4 ChemAxon inchi InChI=1S/C16H18O4/c1-19-14-8-12(7-13(17)10-14)4-3-11-5-6-16(20-2)15(18)9-11/h5-10,17-18H,3-4H2,1-2H3 ChemAxon inchikey SDXKZPQOVUDXIY-UHFFFAOYSA-N ChemAxon polar_surface_area 58.92 ChemAxon refractivity 77.28 ChemAxon polarizability 29.86 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 3085362 Chen H, Huang Y, Huang J, Lin L, Wei G: Gigantol attenuates the proliferation of human liver cancer HepG2 cells through the PI3K/Akt/NF-kappaB signaling pathway. Oncol Rep. 2017 Feb;37(2):865-870. doi: 10.3892/or.2016.5299. Epub 2016 Dec 7. 27959444 Yu S, Wang Z, Su Z, Song J, Zhou L, Sun Q, Liu S, Li S, Li Y, Wang M, Zhang GQ, Zhang X, Liu ZJ, Lu D: Gigantol inhibits Wnt/beta-catenin signaling and exhibits anticancer activity in breast cancer cells. BMC Complement Altern Med. 2018 Feb 14;18(1):59. doi: 10.1186/s12906-018-2108-x. 29444668 Losuwannarak N, Maiuthed A, Kitkumthorn N, Leelahavanichkul A, Roytrakul S, Chanvorachote P: Gigantol Targets Cancer Stem Cells and Destabilizes Tumors via the Suppression of the PI3K/AKT and JAK/STAT Pathways in Ectopic Lung Cancer Xenografts. Cancers (Basel). 2019 Dec 17;11(12). pii: cancers11122032. doi: 10.3390/cancers11122032. 31861050 Charoenrungruang S, Chanvorachote P, Sritularak B, Pongrakhananon V: Gigantol, a bibenzyl from Dendrobium draconis, inhibits the migratory behavior of non-small cell lung cancer cells. J Nat Prod. 2014 Jun 27;77(6):1359-66. doi: 10.1021/np500015v. Epub 2014 May 20. 24844664 1.0 2020-03-18 23:25:15 UTC 2020-08-04 22:27:57 UTC CDB000113 Nonatriacontane Nonatriacontane¬† (CH3-[CH2]37-CH3) belongs to the class of organic compounds known as alkanes, specifically long chain alkane, and has 39 carbon atoms in its unbranched, acyclic structure. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Nonatriacontane is possibly neutral. Nonatriacontane has been reported to be a part of the cuticle of some plant species (PMID: 7903139) in Melicope latifolia http://www.thegoodscentscompany.com/data/rw1591331.html#tooccur) and also found in Cannabis plants (PMID: 6991645). C39H80 549.07 548.626 nonatriacontane nonatriacontane 7194-86-7 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C39H80/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-39H2,1-2H3 SNXOSZZZNFRFNZ-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane logp 11.29 ALOGPS logs -8.04 ALOGPS logp 17.8 ChemAxon iupac nonatriacontane ChemAxon average_mass 549.07 ChemAxon mono_mass 548.626 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C39H80 ChemAxon inchi InChI=1S/C39H80/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-39H2,1-2H3 ChemAxon inchikey SNXOSZZZNFRFNZ-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 181.24 ChemAxon polarizability 82.85 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 114842 Alkane Estrada-Pena A, Guglielmone AA, Mangold AJ, Castella J: Patterns of cuticular hydrocarbon variation and genetic similarity between natural populations of Amblyomma cajennense (Acari: Ixodidae). Acta Trop. 1993 Oct;55(1-2):61-78. doi: 10.1016/0001-706x(93)90049-h. 7903139 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:18 UTC 2020-07-07 15:55:22 UTC CDB000114 beta-Humulene Beta-humulene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytoplasm (PMID:23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-humulene is possibly neutral. Beta-humulene is found in hops (Humulus lupulus) a member of the Cannabaceae family and in Cannabis plants (PMID: 6991645). It is also detected in allspice and guava fruit, celery seed, lemon oil and spearmint leaf ( http://www.thegoodscentscompany.com/data/rw1539551.html#tooccur ). b-Humulene Β-humulene (e,e)-1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene 1,4,4-Trimethyl-8-methylene-(e,e)-1,5-cycloundecadiene 1,4,4-Trimethyl-8-methylene-1,5-cycloundecadiene C15H24 204.35 204.1878 (1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene (1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene 116-04-1 C\C1=C\CC(C)(C)\C=C/CC(=C)CCC1 InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6,10-11H,1,5,7-9,12H2,2-4H3/b11-6-,14-10- HAVYZKHVTLAPDZ-PRUKLFJYSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Humulane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon melting_point < 25 °C logp 5.97 ALOGPS logs -4.93 ALOGPS logp 4.94 ChemAxon iupac (1Z,5Z)-1,4,4-trimethyl-8-methylidenecycloundeca-1,5-diene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C\C1=C\CC(C)(C)\C=C/CC(=C)CCC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6,10-11H,1,5,7-9,12H2,2-4H3/b11-6-,14-10- ChemAxon inchikey HAVYZKHVTLAPDZ-PRUKLFJYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 70.48 ChemAxon polarizability 26.04 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB017456 20120040 21159064 C00012455 49312 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:25:20 UTC 2020-07-24 23:30:06 UTC CDB000115 heptatriacontane Heptatriacontane (CH3-[CH2]35-CH3) belongs to the class of organic compounds known as alkanes, specifically long chain alkane, and has 37 carbon atoms in its unbranched, acyclic structure. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Heptatriacontane is possibly neutral and soluble in water. Heptatriacontane has been reported to be a part of the cuticle of some plant species (PMID: 7903139) and is also found in Cannabis plants (PMID: 6991645). It also occurs in the seeds of lentils, green beans and chickpeas ( http://www.thegoodscentscompany.com/data/rw1587821.html#tooccur). C37H76 521.02 520.5947 heptatriacontane N-heptatriacontane 7194-84-5 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C37H76/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-37H2,1-2H3 PXEZIKSRSYGOED-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane logp 11.23 ALOGPS logs -8.03 ALOGPS logp 16.91 ChemAxon iupac heptatriacontane ChemAxon average_mass 521.02 ChemAxon mono_mass 520.5947 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C37H76 ChemAxon inchi InChI=1S/C37H76/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-37H2,1-2H3 ChemAxon inchikey PXEZIKSRSYGOED-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 172.04 ChemAxon polarizability 78.45 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Estrada-Pena A, Guglielmone AA, Mangold AJ, Castella J: Patterns of cuticular hydrocarbon variation and genetic similarity between natural populations of Amblyomma cajennense (Acari: Ixodidae). Acta Trop. 1993 Oct;55(1-2):61-78. doi: 10.1016/0001-706x(93)90049-h. 7903139 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:23 UTC 2020-08-04 22:27:57 UTC CDB000116 Octatriacontane Octatriacontane is a long-chain hydrocarbon containing 38 carbons. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Pentatriacontane is a very hydrophobic molecule, completely insoluble in water, and fully neutral. Octatriacontane exists as a waxy solid. It is a naturally occurring compound that is found in several plant essential oils and in Candelilla wax. Candelilla wax is a wax derived from the leaves of the small Candelilla shrub native to northern Mexico and the southwestern United States. The Candelilla shrub is a member of the Euphorbia plant genus, from the family Euphorbiaceae. Candelilla wax is used as a food additive and a glazing agent. It also used in cosmetic industry, as a component of lip balms and lotion bars. One of its major uses is as a binder for chewing gums. Candelilla wax can be used as a substitute for carnauba wax and beeswax. It is also used for making varnish. Octatriacontane is one of many alkanes that are known in cannabis plants (PMID: 6991645). C38H78 535.04 534.6104 octatriacontane N-octatriacontane 7194-85-6 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C38H78/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-38H2,1-2H3 BVKCQBBZBGYNOP-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane logp 11.26 ALOGPS logs -8.03 ALOGPS logp 17.36 ChemAxon iupac octatriacontane ChemAxon average_mass 535.04 ChemAxon mono_mass 534.6104 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C38H78 ChemAxon inchi InChI=1S/C38H78/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-38H2,1-2H3 ChemAxon inchikey BVKCQBBZBGYNOP-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 176.64 ChemAxon polarizability 80.6 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:25 UTC 2020-09-11 20:08:57 UTC CDB000117 Arginine Arginine is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. Arginine can be considered to be a basic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing, and hydrophobic, whereas the end of the side chain is a complex guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is used to make compounds such as nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of the hormones growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502¬†). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355¬†). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein. Arginine is one of the amino acids that are known in cannabis plant (PMID: 6991645). (2R)-2-Amino-5-(carbamimidamido)pentanoic acid (2R)-2-Amino-5-guanidinopentanoic acid (R)-2-Amino-5-guanidinopentanoic acid D-2-Amino-5-guanidinovaleric acid D-Arginin DAR (2R)-2-Amino-5-(carbamimidamido)pentanoate (2R)-2-Amino-5-guanidinopentanoate (R)-2-Amino-5-guanidinopentanoate D-2-Amino-5-guanidinovalerate C6H14N4O2 174.2 174.1117 (2R)-2-amino-5-carbamimidamidopentanoic acid D-arginine 157-06-2 N[C@H](CCCNC(N)=N)C(O)=O InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1 ODKSFYDXXFIFQN-SCSAIBSYSA-N belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboximidamides Carboxylic acids Fatty acids and conjugates Guanidines Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Amine Amino acid Carbonyl group Carboximidamide Carboxylic acid D-alpha-amino acid Fatty acid Guanidine Hydrocarbon derivative Monocarboxylic acid or derivatives Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound D-alpha-amino acid Other amino acids arginine water_solubility 14.87 g/100 mL at 20 °C Wikipedia logp 0.0 Wikipedia melting_point 260 °C Wikipedia boiling_point 368 °C Wikipedia logp -3.49 ALOGPS logs -1.88 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 2.41 ChemAxon pka_strongest_basic 12.41 ChemAxon iupac (2R)-2-amino-5-carbamimidamidopentanoic acid ChemAxon average_mass 174.2 ChemAxon mono_mass 174.1117 ChemAxon smiles N[C@H](CCCNC(N)=N)C(O)=O ChemAxon formula C6H14N4O2 ChemAxon inchi InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1 ChemAxon inchikey ODKSFYDXXFIFQN-SCSAIBSYSA-N ChemAxon polar_surface_area 125.22 ChemAxon refractivity 53.92 ChemAxon polarizability 18.04 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 64224 C00792 DB04027 FDB023167 71070 15816 CPD-220 36012 Arginine 6924 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Bauchart-Thevret C, Cui L, Wu G, Burrin DG: Arginine-induced stimulation of protein synthesis and survival in IPEC-J2 cells is mediated by mTOR but not nitric oxide. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E899-909. doi: 10.1152/ajpendo.00068.2010. Epub 2010 Sep 14. 20841502 Linden KC, Wadley GD, Garnham AP, McConell GK: Effect of l-arginine infusion on glucose disposal during exercise in humans. Med Sci Sports Exerc. 2011 Sep;43(9):1626-34. doi: 10.1249/MSS.0b013e318212a317. 21311355 1.0 2020-03-18 23:25:27 UTC 2020-08-04 22:27:57 UTC CDB000118 beta-Curcumene Beta-curcumene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, in plants, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytoplasm (PMID:23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-curcumene is possibly neutral. Beta-curcumene has been detected in several plant species, as well as in Cannabis sativa (PMID: 6991645). It occurs in java ginger, turmeric, cedrala wood oil and sandal wood oil ( http://www.thegoodscentscompany.com/data/rw1701351.html#tooccur ). beta-Curcumene b-Curcumene Β-curcumene (-)-b-Curcumene (-)-Β-curcumene C15H24 204.36 204.1878 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,4-diene (-)-β-curcumene C[C@H](CCC=C(C)C)C1=CCC(C)=CC1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,11,14H,5,7,9-10H2,1-4H3/t14-/m1/s1 JXZQZARENYGJMK-CQSZACIVSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon beta-curcumene logp 6.03 ALOGPS logs -3.92 ALOGPS logp 4.82 ChemAxon iupac 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,4-diene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H](CCC=C(C)C)C1=CCC(C)=CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,11,14H,5,7,9-10H2,1-4H3/t14-/m1/s1 ChemAxon inchikey JXZQZARENYGJMK-CQSZACIVSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.36 ChemAxon polarizability 26.47 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 62760 14014430 CPD-11392 C00011630 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:25:29 UTC 2020-09-11 20:08:27 UTC CDB000119 alpha-Bisabolol Alpha-Bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406) Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Epi-Alpha-Bisabolol is an isomer of Bisabolol. Bisabolol or more formally Œ±-(‚àí)-bisabolol is a colorless viscous oil. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322), and of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645, 26657499). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/f11030290). Bisabolol has a weak sweet floral aroma and is used in various fragrances. Levomenol (-)-a-Bisabolol (-)-Α-bisabolol Bisabolol, (-)-isomer Bisabolol a-Bisabolol Α-bisabolol (-)-(1's,2S)-alpha-Bisabolol (-)-(1's,2S)-Α-bisabolol (-)-(1’S,2S)-α-bisabolol (-)-(4S,8S)-alpha-Bisabolol (-)-(4S,8S)-Α-bisabolol (AlphaS,1S)-alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol (ΑS,1S)-α,4-dimethyl-α-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol alpha-(-)-Bisabolol L-alpha-Bisabolol L-Α-bisabolol Α-(-)-bisabolol (-)-alpha-Bisabolol C15H26O 222.37 222.1984 (2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol bisabolol 23089-26-1 CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1 RGZSQWQPBWRIAQ-CABCVRRESA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol Bisabolane sesquiterpenoids Bisabolane sesquiterpenoids Bisabolanes sesquiterpenoid logp 4.76 ALOGPS logs -3.48 ALOGPS logp 3.91 ChemAxon pka_strongest_basic -0.47 ChemAxon iupac (2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1 ChemAxon inchikey RGZSQWQPBWRIAQ-CABCVRRESA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 72.19 ChemAxon polarizability 28.29 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 442343 DB13153 C09621 C00003103 C00011607 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Singh O, Khanam Z, Misra N, Srivastava MK: Chamomile (Matricaria chamomilla L.): An overview. Pharmacogn Rev. 2011 Jan;5(9):82-95. doi: 10.4103/0973-7847.79103. 22096322 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. 31659569 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:25:31 UTC 2020-09-11 20:08:57 UTC CDB000120 Lysine Lysine and its bioactive form L-lysine, abbreviated Lys or L, is an essential amino acid. Normal requirements for adults are between 8 g per day or 12 mg/kg. Children and infants need more: 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize these levels and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture and has helped to reduce the number and occurrence of cold sores in clinical studies. Beneficial clinical effects occurred with lysine doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes as excess arginine antagonizes lysine. Lysine also may be a useful adjunct in the treatment of osteoporosis because it reduces calcium losses in urine. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine is high in foods such as wheat germ, cottage cheese, chicken, wild game and pork. Less lysine is found in apple, apricot, bananas, avocados, guava, lime, brazil nuts, cashews, mung bean, fava bean and black bean as well as other seeds, nuts and fruits. Lysine is also found in cannabis plants (PMID: 6991645). Lysin is also a constituent of cannabis smok and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). (R)-2,6-Diaminohexanoic acid D-2,6-Diaminohexanoic acid D-Lysin DLY (R)-2,6-Diaminohexanoate D-2,6-Diaminohexanoate C6H14N2O2 146.19 146.1055 (2R)-2,6-diaminohexanoic acid D-lysine 923-27-3 NCCCC[C@@H](N)C(O)=O InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 KDXKERNSBIXSRK-RXMQYKEDSA-N belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid D-alpha-amino acid Fatty acid Fatty acyl Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine D-alpha-amino acid Other amino acids lysine water_solubility 1.5 kg/L Wikipedia logp -3.76 ALOGPS logs -0.14 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 2.74 ChemAxon pka_strongest_basic 10.29 ChemAxon iupac (2R)-2,6-diaminohexanoic acid ChemAxon average_mass 146.19 ChemAxon mono_mass 146.1055 ChemAxon smiles NCCCC[C@@H](N)C(O)=O ChemAxon formula C6H14N2O2 ChemAxon inchi InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 ChemAxon inchikey KDXKERNSBIXSRK-RXMQYKEDSA-N ChemAxon polar_surface_area 89.34 ChemAxon refractivity 37.81 ChemAxon polarizability 15.91 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 57449 C00739 FDB023163 DB03252 16855 Lysine CPD-219 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:34 UTC 2020-07-24 23:30:06 UTC CDB000121 N-Methylnicotinate N-Methylnicotinate or Trigonelline, also known as caffearin or gynesine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Trigonelline is a moderately acidic compound. Trigonelline exists in all living organisms, from bacteria to humans. It is a product of the metabolism of niacin (vitamin B3) and it is excreted in the urine. Trigonelline in urine is a biomarker for the consumption of coffee, legumes and soy products. Trigonelline is found in highest concentrations in arabica coffee, fenugreeks, and common pea and in lower concentrations in yellow bell peppers, orange bell peppers, and muskmelons. Trigonelline has also been detected in rices, triticales, alfalfa, cereals and cereal products, ryes fenugreek seeds, garden peas, hemp seed (Cannabis sativa; PMID: 6991645), oats and potatoes. Trigonelline may reduce dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. It also has shown anti-carcinogenic and anti-hyperglycemic effects in several studies (PMID: 22680628; PMID: 31896496; PMID: 31363374). 1-Methyl-3-pyridiniumcarboxylate 1-Methylnicotinate 1-Methylpyridinio-3-carboxylate 3-Carboxy-1-methylpyridinium hydroxide inner salt Betain nicotinate Betaine nicotinate Caffearin Caffearine Coffearin Gynesine N'-methylnicotinate N-Methyl-nicotinate Nicotinic acid N-methylbetaine Trigenelline Trigonellin 1-Methyl-3-pyridiniumcarboxylic acid 1-Methylnicotinic acid 1-Methylpyridinio-3-carboxylic acid Betain nicotinic acid Betaine nicotinic acid N'-methylnicotinic acid N-Methyl-nicotinic acid Nicotinate N-methylbetaine N-Methylnicotinic acid Trigonelline chloride Trigonelline iodide Trigonelline tosylate Trigonelline ion 3-Carboxy-1-methyl-pyridinium hydroxide inner salt Coffearine N-Methylnicotinate Trigenolline Trigonelline C7H7NO2 137.14 137.0477 1-methylpyridin-1-ium-3-carboxylate trigonelline 535-83-1 C[N+]1=CC=CC(=C1)C([O-])=O InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 WWNNZCOKKKDOPX-UHFFFAOYSA-N belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Alkaloids and derivatives Organic compounds Alkaloids and derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Carboxylic acid salts Carboxylic acids Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives N-methylpyridinium compounds Organic oxides Organic salts Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Pyridinecarboxylic acids Pyridinium derivatives Vinylogous amides Alkaloid or derivatives Aromatic heteromonocyclic compound Azacycle Carboxylic acid Carboxylic acid derivative Carboxylic acid salt Heteroaromatic compound Hydrocarbon derivative Monocarboxylic acid or derivatives N-methylpyridinium Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyridine Pyridine carboxylic acid Pyridine carboxylic acid or derivatives Pyridinium Vinylogous amide Pyridine alkaloids a small molecule alkaloid iminium betaine logp -3.30 ALOGPS logs -2.77 ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 2.78 ChemAxon iupac 1-methylpyridin-1-ium-3-carboxylate ChemAxon average_mass 137.14 ChemAxon mono_mass 137.0477 ChemAxon smiles C[N+]1=CC=CC(=C1)C([O-])=O ChemAxon formula C7H7NO2 ChemAxon inchi InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3 ChemAxon inchikey WWNNZCOKKKDOPX-UHFFFAOYSA-N ChemAxon polar_surface_area 44.01 ChemAxon refractivity 48.15 ChemAxon polarizability 13.4 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01004 FDB002237 5369 5570 18123 METHYLNICOTINATE Trigonelline C00001555 273 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zhou J, Chan L, Zhou S: Trigonelline: a plant alkaloid with therapeutic potential for diabetes and central nervous system disease. Curr Med Chem. 2012;19(21):3523-31. doi: 10.2174/092986712801323171. 22680628 Nugrahini AD, Ishida M, Nakagawa T, Nishi K, Sugahara T: Trigonelline: An alkaloid with anti-degranulation properties. Mol Immunol. 2020 Feb;118:201-209. doi: 10.1016/j.molimm.2019.12.020. Epub 2019 Dec 30. 31896496 Li Y, Li Q, Wang C, Lou Z, Li Q: Trigonelline reduced diabetic nephropathy and insulin resistance in type 2 diabetic rats through peroxisome proliferator-activated receptor-gamma. Exp Ther Med. 2019 Aug;18(2):1331-1337. doi: 10.3892/etm.2019.7698. Epub 2019 Jun 21. 31363374 1.0 2020-03-18 23:25:38 UTC 2020-08-04 22:27:58 UTC CDB000123 1-Propylamine 1-Propylamine, also known as 1-aminopropane or propylamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. 1-Propylamine is a weak base and a colorless volatile liquid with an ammoniacal taste. 1-Propylamine is found in higher concentrations in yellow bell peppers, red bell peppers, and pepper (Capsicum annuum) and in lower concentrations in orange bell peppers and green bell peppers. 1-Propylamine has also been detected in common grapes and wild celeries. This could make 1-propylamine a potential biomarker for the consumption of these foods. Propyl amine hydrochloride can be prepared by reacting 1-propanol with ammonium chloride at high temperature and pressure using a Lewis acid catalyst such as ferric chloride. Propylamine is also found in cannabis plants (PMID: 6991645). 1-Aminopropane 1-Propanamine mono-N-Propylamine N-Propylamine (C10-C16) Alkylalkoxypropyleneamine (C10-C16)Alkylalkoxypropyleneamine (C12-C18) Alkylalkoxypropyleneamine (C12-C18)Alkyl alkoxypropylene amine (C14-C18)Alkylalkoxypropyleneamine (C16-C22)Alkyl alkoxypropyleneamine (C6-C12) Alkylalkoxypropyleneamine (C6-C12)Alkylalkoxypropyleneamine 1-Propanamine, 3-(C10-16-alkyloxy) derivs. 1-Propanamine, 3-(C12-18-alkyloxy) derivs. 1-Propanamine, 3-(C14-18-alkyloxy) derivs. 1-Propanamine, 3-(C16-22-alkyloxy) derivs. 1-Propanamine, 3-(C6-12-alkyloxy) derivs. 3-AMINOPROPYL AYE Monopropylamine N-C3H7NH2 N-Propyl amine Propan-1-amine Propanamine Propanamine, 9ci Propyl amines Propylamine 1-Propylamine C3H9N 59.11 59.0735 propan-1-amine propylamine 107-10-8 CCCN InChI=1S/C3H9N/c1-2-3-4/h2-4H2,1H3 WGYKZJWCGVVSQN-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine a small molecule alkylamines water_solubility 1000 mg/mL at 20 °C logp 0.48 melting_point -83 °C boiling_point 47 - 51 °C Wikipedia logp 0.31 ALOGPS logs 0.59 ALOGPS logp 0.25 ChemAxon pka_strongest_basic 10.21 ChemAxon iupac propan-1-amine ChemAxon average_mass 59.11 ChemAxon mono_mass 59.0735 ChemAxon smiles CCCN ChemAxon formula C3H9N ChemAxon inchi InChI=1S/C3H9N/c1-2-3-4/h2-4H2,1H3 ChemAxon inchikey WGYKZJWCGVVSQN-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 19.19 ChemAxon polarizability 7.68 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012241 7852 7564 39870 3CN CPD-9379 Propylamine Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:40 UTC 2020-08-04 22:27:58 UTC CDB000124 Butan-1-amine 1-Butylamine, also known as 1-aminobutan or N-C4H9NH2, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. 1-Butylamine is a very strong basic compound (based on its pKa). Butylamine is a colourless liquid which acquires a yellow colour when exposed to air during storage. 1-Butylamine is an ammonia and fishy tasting compound. Outside of the human body, 1-Butylamine has been detected, but not quantified in several different foods, such as cocoa and cocoa products, brassicas, fishes, garden tomato, and milk and milk products. This could make 1-butylamine a potential biomarker for the consumption of these foods. It is one of the four isomeric amines of butane. It is known to have the fishy, ammonia-like odor common to amines. Also found in mulberry leaves, kale, swede, tomato, wheat bread, cheeses, caviar, raw fatty fish, cooked chicken or beef, beer, cocoa, and other foodstuffs. Butan-1-amine is also found in cannabis plants (PMID: 6991645). 1-Aminobutan 1-Aminobutane 1-Butanamine Butanamine Butylamine mono-N-Butylamine Monobutylamine N-Butylamin N-Butylamine N-C4H9NH2 1-Butanamine, 9ci Aminobutane FEMA 3130 Norralamine Norvalamine N-Butylamine hydrobromide N-Butylamine hydrochloride, 14C-labeled CPD N-Butylamine hydrochloride 1-Butylamine C4H11N 73.14 73.0891 butan-1-amine butylamine 109-73-9 CCCCN InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 HQABUPZFAYXKJW-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine a small molecule primary aliphatic amine water_solubility 1000 mg/mL at 20 °C logp 0.97 melting_point -50 °C logp 0.85 ALOGPS logs 0.04 ALOGPS logp 0.7 ChemAxon pka_strongest_basic 10.21 ChemAxon iupac butan-1-amine ChemAxon average_mass 73.14 ChemAxon mono_mass 73.0891 ChemAxon smiles CCCCN ChemAxon formula C4H11N ChemAxon inchi InChI=1S/C4H11N/c1-2-3-4-5/h2-5H2,1H3 ChemAxon inchikey HQABUPZFAYXKJW-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 23.79 ChemAxon polarizability 9.66 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB03659 8007 7716 FDB003380 LYT 43799 BUTYLAMINE N-Butylamine Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:42 UTC 2020-08-04 22:27:58 UTC CDB000125 2-Methylpropanamine 2-Methyl-1-propylamine, also known as isobutylamine or valamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. 2-Methyl-1-propylamine is a strong basic compound. 2-Methyl-1-propylamine is a clear, colorless liquid with a cheesy and fishy taste. 2-Methyl-1-propylamine exists in all living organisms, from bacteria to humans. 2-Methyl-1-propylamine has been detected in black elderberries, common grapes, and French plantains. This could make 2-methyl-1-propylamine a potential biomarker for the consumption of these foods. 2-Methyl-1-propylamine is also found in Cannabis plants (PMID: 6991645). 1-Amino-2-methylpropane 2-Methyl-1-aminopropane 2-Methyl-1-propanamine 2-Methylpropylamine 3-Methyl-2-propylamine I-butylamine IBA Iso-butylamine Iso-C4H9NH2 Isobutylamine Monoisobutylamine Valamine 2-Methylpropan-1-amine 2-Methyl-1-propanamine, 9ci 2-Methylpropanamine Isobutylamine, 8ci Valamine? Isobutylamine hydrochloride C4H11N 73.14 73.0891 2-methylpropan-1-amine isobutylamine 78-81-9 CC(C)CN InChI=1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3 KDSNLYIMUZNERS-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine a small molecule alkylamines water_solubility 1000 mg/mL at 25 °C logp 0.73 melting_point -84.6 °C logp 0.54 ALOGPS logs 0.07 ALOGPS logp 0.62 ChemAxon pka_strongest_basic 10.24 ChemAxon iupac 2-methylpropan-1-amine ChemAxon average_mass 73.14 ChemAxon mono_mass 73.0891 ChemAxon smiles CC(C)CN ChemAxon formula C4H11N ChemAxon inchi InChI=1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3 ChemAxon inchikey KDSNLYIMUZNERS-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 23.66 ChemAxon polarizability 9.51 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012495 6310 6558 C02787 CPD-630 Isobutylamine IBN 15997 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:44 UTC 2020-09-11 20:08:56 UTC CDB000126 Phenylethylamine Phenylethylamine (PEA) is an aromatic amine which has a constitutional isomer (+)-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. It is a strongly basic, colorless liquid at room temperature which is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenylethylamines can be biosynthesized in mammals from the amino acid phenylalanine by enzymatic decarboxylation. Phenylethylamine is produced after microbial fermentation and is a metabolite of Bacillus, Enterococcus, Pseudomanas and Lactobacillus (PMID: 22953951; PMID: 17307265; PMID: 16630269) and has anti-microbial properties against pathogenic strains of E. coli. It is found in many foods such as chocolate. However, trace amounts from food are quickly metabolized by the enzyme monoamine oxidase (MAO-B) into phenylacetic acid, preventing significant concentrations from reaching the brain. In the human brain, phenylethylamine is a central nervous system stimulant that binds to the human trace amine-associated receptor 1¬†(hTAAR1) as an¬†agonist (PMID: 27424325). It is a precursor to the neurotransmitter phenylethanolamine. High levels of PEA have been found in the urine of schizophrenics, but it is not significantly elevated in the serum or CSF of schizophrenics (PMID: 7906896, PMID: 7360842). Urinary levels of PEA are significantly lower in children with attention deficit hyperactivity disorder (ADHD) (PMID: 12205654). Phenylethylamine is also a skin irritant and possible sensitizer. PEA is the primary compound found in carnivore urine (especially cat) that repels mice and rats. Quantitative HPLC analysis across 38 mammalian species has shown that PEA production in urine is especially high in carnivores, with some producing >3,000-fold more than herbivores (PMID: 21690383). PEA is also found in Cannabis plants (PMID: 6991645). Benzeneethanamine beta-Aminoethylbenzene beta-Phenethylamine beta-Phenylethylamine Phenethylamine 2-Phenylethylamine b-Aminoethylbenzene Β-aminoethylbenzene b-Phenethylamine Β-phenethylamine b-Phenylethylamine Β-phenylethylamine (2-Aminoethyl)benzene (2-Aminoethyl)polystyrene 1-Amino-2-phenylethane 1-Phenethylamine 1-Phenyl-2-amino-athan 1-Phenyl-2-aminoethane 1TNJ 1Utm 1Uto 2-Amino-1-phenylethane 2-Amino-fenylethan 2-Fenylethylamin 2-Phenethylamine 2-Phenyl-ethanamine 2-Phenylethanamine 2-Phenylethanamine (acd/name 4.0) 2-Phenylethylamine (acd/name 4.0) b-Phenylaethylamin Benzeneethanamine hydrochloride beta Phenethylamine beta-Phenylaethylamin Omega-phenylethylamine PEA Phenethylamine hydrochloride Polystyrene a-NH2 Phenethylamine hydrobromide Phenethylamine tosylate Phenethylamine conjugate acid Phenethylamine sulfate Phenethylamine, monolithium salt 2-Phenylethylammonium chloride Phenethylamine sulfate (2:1) Phenethylamine, 15N-labeled CPD Phenethylamine mesylate Phenethylamine perchlorate Phenethylamine, beta-(14)C-labeled CPD Diphenethylamine sulfate C8H11N 121.18 121.0891 2-phenylethan-1-amine 2-phenylethylamine 64-04-0 NCCC1=CC=CC=C1 InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 BHHGXPLMPWCGHP-UHFFFAOYSA-N belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Phenethylamines Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic homomonocyclic compounds 2-arylethylamines Aralkylamines Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds 2-arylethylamine Amine Aralkylamine Aromatic homomonocyclic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Phenethylamine Primary aliphatic amine Primary amine Biogenic amines alkaloid aralkylamine phenylethylamine logp 1.41 ALOGPS logs -1.74 ALOGPS logp 1.39 ChemAxon pka_strongest_basic 9.79 ChemAxon iupac 2-phenylethan-1-amine ChemAxon average_mass 121.18 ChemAxon mono_mass 121.0891 ChemAxon smiles NCCC1=CC=CC=C1 ChemAxon formula C8H11N ChemAxon inchi InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 ChemAxon inchikey BHHGXPLMPWCGHP-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 39.29 ChemAxon polarizability 14.35 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04325 FDB010580 13856352 1001 C05332 18397 C00001426 2-phenylethylamine PHENYLETHYLAMINE Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kim B, Byun BY, Mah JH: Biogenic amine formation and bacterial contribution in Natto products. Food Chem. 2012 Dec 1;135(3):2005-11. doi: 10.1016/j.foodchem.2012.06.091. Epub 2012 Jul 3. 22953951 Landete JM, Pardo I, Ferrer S: Tyramine and phenylethylamine production among lactic acid bacteria isolated from wine. Int J Food Microbiol. 2007 Apr 20;115(3):364-8. doi: 10.1016/j.ijfoodmicro.2006.10.051. Epub 2007 Jan 18. 17307265 Marcobal A, de las Rivas B, Munoz R: First genetic characterization of a bacterial beta-phenylethylamine biosynthetic enzyme in Enterococcus faecium RM58. FEMS Microbiol Lett. 2006 May;258(1):144-9. doi: 10.1111/j.1574-6968.2006.00206.x. 16630269 Khan MZ, Nawaz W: The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed Pharmacother. 2016 Oct;83:439-449. doi: 10.1016/j.biopha.2016.07.002. Epub 2016 Jul 15. 27424325 O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75. doi: 10.1016/0278-5846(94)90024-8. 7906896 Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4. 7360842 Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. doi: 10.1002/ana.10302. 12205654 Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20. 21690383 1.0 2020-03-18 23:25:47 UTC 2020-07-24 23:30:06 UTC CDB000127 Pentylamine Pentylamine, or CH3(CH2)4NH2, also known as amylanine, 1-pentylamine or 1-aminopentane, is a member of the class of compounds known as monoalkylamines. Monoalkylamines are organic compounds containing a primary aliphatic amine group. Pentylamine is a strong basic compound that is soluble in water. Pentylamine is an ammoniacal and fishy taste and can be found in a number of food items such as yellow bell pepper, apple, pepper (Capsicum annuum), and cabbage, which makes pentylamine a potential biomarker for the consumption of these food products. It is used as a solvent, as a raw material in the manufacture of a variety of other compounds, including dyes, emulsifiers, and pharmaceutical products, and as a flavoring agent. Pentylamine is also found in Cannabis plants (PMID: 6991645). 1-Aminopentane 1-Pentanamine 1-Pentylamine CH3(CH2)4nh2 Me(CH2)4nh2 Monoamylamine N-AmNH2 N-Amylamine N-C5H11NH2 N-Pentylamine Norleucamine Pentylamine Amylamine hydrochloride N-Amylamine hydrochloride N-Amylamine sulfate (2:1) C5H13N 87.16 87.1048 pentan-1-amine amylamine 110-58-7 CCCCCN InChI=1S/C5H13N/c1-2-3-4-5-6/h2-6H2,1H3 DPBLXKKOBLCELK-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine an amine primary aliphatic amine melting_point −55 °C Wikipedia boiling_point 94 - 110 °C Wikipedia logp 1.39 ALOGPS logs -0.69 ALOGPS logp 1.14 ChemAxon pka_strongest_basic 10.21 ChemAxon iupac pentan-1-amine ChemAxon average_mass 87.16 ChemAxon mono_mass 87.1048 ChemAxon smiles CCCCCN ChemAxon formula C5H13N ChemAxon inchi InChI=1S/C5H13N/c1-2-3-4-5-6/h2-6H2,1H3 ChemAxon inchikey DPBLXKKOBLCELK-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 28.39 ChemAxon polarizability 11.68 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB02045 8060 FDB010039 74848 CPD-3681 Pentylamine Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:49 UTC 2020-09-11 20:08:56 UTC CDB000128 L-Alanine L-Alanine or Alanine, abbreviated Ala or A, is a non-essential amino acid made in the body from either the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. L-Alanine has been found to be associated with glucagon deficiency, which is an inborn error of metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. L-alanine is also found in Cannabis plants (PMID: 6991645). (2S)-2-Aminopropanoic acid (S)-2-Aminopropanoic acid (S)-Alanine A Ala ALANINE L-2-Aminopropionic acid L-Alanin L-alpha-Alanine (2S)-2-Aminopropanoate (S)-2-Aminopropanoate L-2-Aminopropionate L-a-Alanine L-Α-alanine (S)-(+)-Alanine (S)-2-Amino-propanoate (S)-2-Amino-propanoic acid 2-Aminopropanoate 2-Aminopropanoic acid 2-Aminopropionate 2-Aminopropionic acid 2-Ammoniopropanoate 2-Ammoniopropanoic acid a-Alanine a-Aminopropionate a-Aminopropionic acid alpha-Alanine alpha-Aminopropanoate alpha-Aminopropanoic acid alpha-Aminopropionate alpha-Aminopropionic acid L-(+)-Alanine L-2-Aminopropanoate L-2-Aminopropanoic acid L-a-Aminopropionate L-a-Aminopropionic acid L-alpha-Aminopropionate L-alpha-Aminopropionic acid Abufène Alanine doms-adrian brand Alanine, L-isomer Doms-adrian brand OF alanine Doms adrian brand OF alanine L-Isomer alanine Alanine, L isomer L Alanine C3H7NO2 89.09 89.0477 (2S)-2-aminopropanoic acid L-alanine 115967-49-2 C[C@H](N)C(O)=O InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1 QNAYBMKLOCPYGJ-REOHCLBHSA-N belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Alanine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Alanine or derivatives Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Common amino acids L-alpha-amino acid alanine proteinogenic amino acid pyruvate family amino acid water_solubility 204 mg/mL Human Metabolome Project logp -2.85 SANGSTER (1994) melting_point 300 °C logp -3.05 ALOGPS logs 0.70 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 2.47 ChemAxon pka_strongest_basic 9.48 ChemAxon iupac (2S)-2-aminopropanoic acid ChemAxon average_mass 89.09 ChemAxon mono_mass 89.0477 ChemAxon smiles C[C@H](N)C(O)=O ChemAxon formula C3H7NO2 ChemAxon inchi InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1 ChemAxon inchikey QNAYBMKLOCPYGJ-REOHCLBHSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 20.5 ChemAxon polarizability 8.49 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00041 5735 DB00160 FDB000556 5950 16977 L-ALPHA-ALANINE C00001332 Alanine 33629 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:51 UTC 2020-08-04 22:28:01 UTC CDB000129 L-Cystine Cystine is an oxidized dimeric form of cysteine, an amino acid. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. This organosulfur compound has the formula (SCH2CH(NH2) CO2H)2. It is a colorless solid that melts at 247-249 ¬∞C. It was discovered in 1810 by William Hyde Wollaston but was not recognized as being derived of proteins until it was isolated from the horn of a cow in 1899. Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Cystine also functions in redox reactions. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions, is partially responsible for the formation of the gluten matrix in bread. Cystine is found in high concentrations in the cells of the immune system, skeletal and connective tissues, skin, digestive enzymes, and in hair. It is found largely withing nonreducing organelles within cells such as the Golgi, ER, lysosomes and vesicles while cysteine is found in the reducing environment of the cytoplasm and the extracellular space. Cystine is the preferred form of cysteine for the synthesis of glutathione (a tripeptide consisting of cysteine, glutamate and glycine) in cells involved in the immune function including macrophages and astrocytes. Lymphocytes and neurons prefer cysteine for glutathione production. Optimizing glutathione levels in macrophages and astrocytes with cystine allows these cells to provide cysteine to lymphocytes and neurons directly upon demand. Cystine naturally occurs as a deposit in the urine and can form a calculus (hard mineral formation) when deposited in the kidney. Cystine is required for proper vitamin B6 utilization and is also helpful in the healing of burns and wounds, breaking down mucus deposits in illnesses such as bronchitis as well as cystic fibrosis. Cysteine also assists in the supply of insulin to the pancreas, which is needed for the assimilation of sugars and starches. It increases the level of glutathione in the lungs, liver, kidneys and bone marrow, and this may have an anti-aging effect on the body by reducing age-spots etc. Cystine is also found in Cannabis plants (PMID: 6991645). (R,R)-3,3'-Dithiobis(2-aminopropanoic acid) (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid) 3,3'-Dithiobis-L-alanine beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide beta,Beta'-dithiodialanine Bis(beta-amino-beta-carboxyethyl) disulfide e921 L-alpha-Diamino-beta-dithiolactic acid L-Dicysteine Oxidized L-cysteine (R,R)-3,3'-Dithiobis(2-aminopropanoate) (R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate) b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide b,Beta'-dithiodialanine Β,beta'-dithiodialanine Bis(b-amino-b-carboxyethyl) disulfide Bis(b-amino-b-carboxyethyl) disulphide Bis(beta-amino-beta-carboxyethyl) disulphide Bis(β-amino-β-carboxyethyl) disulfide Bis(β-amino-β-carboxyethyl) disulphide L-a-Diamino-b-dithiolactate L-a-Diamino-b-dithiolactic acid L-alpha-Diamino-beta-dithiolactate L-Α-diamino-β-dithiolactate L-Α-diamino-β-dithiolactic acid (-)-Cystine (R-(R*,r*))-3,3'-dithiobis 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate 2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate 2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid 3,3'-Dithiobis 3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoate 3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoic acid 3,3'-Dithiodialanine b,B'-diamino-b,b'-dicarboxydiethyl disulfide b,B'-dithiodialanine beta,Beta'-dithiobisalanine Bis(b-amino-beta-carboxyethyl) disulfide Cysteine disulfide Cystin Cystine Cystine acid D(+)-3,3'-Dithiobis(2-aminopropanoate D(+)-3,3'-Dithiobis(2-aminopropanoic acid Dicysteine Gelucystine L-(-)-Cystine L-Cysteine disulfide L-Cystin [R-(R*,r*)]-3,3'-dithiobis L Cystine Copper cystinate L-Cystine C6H12N2O4S2 240.3 240.0238 (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid L-cystine 56-89-3 N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 LEVWYRKDKASIDU-IMJSIDKUSA-N belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. L-cysteine-S-conjugates Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Dialkyldisulfides Dicarboxylic acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Sulfenyl compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Dialkyldisulfide Dicarboxylic acid or derivatives Hydrocarbon derivative L-alpha-amino acid L-cysteine-s-conjugate Organic disulfide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Sulfenyl compound L-cysteine derivative cystine non-proteinogenic L-alpha-amino acid water_solubility 0.19 mg/mL logp -5.08 CHMELIK,J ET AL. (1991) melting_point 260.5 °C logp -3.16 ALOGPS logs -1.16 ALOGPS logp -5.9 ChemAxon pka_strongest_acidic 1.56 ChemAxon pka_strongest_basic 9.34 ChemAxon iupac (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid ChemAxon average_mass 240.3 ChemAxon mono_mass 240.0238 ChemAxon smiles N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C6H12N2O4S2 ChemAxon inchi InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1 ChemAxon inchikey LEVWYRKDKASIDU-IMJSIDKUSA-N ChemAxon polar_surface_area 126.64 ChemAxon refractivity 54.87 ChemAxon polarizability 22.77 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00491 FDB012672 DB00138 67678 60997 16283 C00001352 Cystine 35134 5207 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:25:53 UTC 2020-09-11 20:08:57 UTC CDB000130 L-Glutamic acid L-glutamic acid (abbreviated Glu or E), also referred to as glutamate (the anion), is a non-essential amino acid, one of the 20 amino acids used in the biosynthesis of proteins. L-glutamic acid exists in all living species, from bacteria to humans. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is a component amino acid in many protein rich foods including the gluten protein in flour and is found as a free acid in cheeses and soya sauce. It is used as a flavor enhancer as a sodium salt known as monosodium glutamate. As a proteinogenic amino acid, L-glutamic acid is also found in Cannabis plants (PMID: 6991645). Glutamate is a key molecule in cellular metabolism. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the N-methyl-d-aspartate acid (NMDA) receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, glutamate can accumulate outside cells, causing glutamate excitotoxicity. Excitotoxicity¬†occurs when neurons are exposed to high levels of glutamate or other neurotransmitters, causing persistent activation of the and Œ±-amino-3-hydroxy-5-methylisoxazole propionic acid (AMPA) receptors and voltage-gated calcium channels. This results in a lethal influx of extracellular calcium leading to neuronal damage and eventual cell death. Cell death arises from damage to mitochondria by the excessively high intracellular calcium, which open mitochondrial pores, causing mitochondria to swell. Reactive oxygen species (ROS) may also be released by mitochondria into the intracellular space. Excess glutamate and calcium trigger apoptosis by further activating transcription factors for pro-apoptotic genes, or downregulating transcription factors for anti-apoptotic genes. Glutamate excitotoxicity causes other health consequences. In ischemic stroke and brain trauma, the severely reduced blood supply leads to flooding of glutamate and aspartate into the extra-neuronal space ( PMID: 16314180). Glutamate excitotoxicity is associated with diseases like amyotrophic lateral sclerosis, multiple sclerosis, lathyrism, and Alzheimer's disease (PMID: 20229265) and in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart which is like a paroxysmal depolarizing shift seen in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. Moreover, glutamic acid is associated with N-acetylglutamate synthetase deficiency, which is an inborn error of metabolism. (S)-2-Aminopentanedioic acid (S)-Glutamic acid Acide glutamique Acido glutamico Acidum glutamicum E Glu Glutamate GLUTAMIC ACID L-Glu L-Glutaminic acid L-Glutaminsaeure (S)-2-Aminopentanedioate (S)-Glutamate L-Glutaminate L-Glutamate (2S)-2-Aminopentanedioate (2S)-2-Aminopentanedioic acid (S)-(+)-Glutamate (S)-(+)-Glutamic acid 1-Amino-propane-1,3-dicarboxylate 1-Amino-propane-1,3-dicarboxylic acid 1-Aminopropane-1,3-dicarboxylate 1-Aminopropane-1,3-dicarboxylic acid 2-Aminoglutarate 2-Aminoglutaric acid 2-Aminopentanedioate 2-Aminopentanedioic acid a-Aminoglutarate a-Aminoglutaric acid a-Glutamate a-Glutamic acid Aciglut alpha-Aminoglutarate alpha-Aminoglutaric acid alpha-Glutamate alpha-Glutamic acid Aminoglutarate Aminoglutaric acid Glt Glusate Glut Glutacid Glutamicol Glutamidex Glutaminate Glutaminic acid Glutaminol Glutaton L-(+)-Glutamate L-(+)-Glutamic acid L-a-Aminoglutarate L-a-Aminoglutaric acid L-alpha-Aminoglutarate L-alpha-Aminoglutaric acid D Glutamate Glutamate, potassium Glutamic acid, (D)-isomer L Glutamic acid D-Glutamate L Glutamate Aluminum L glutamate Aluminum L-glutamate L-Glutamate, aluminum Potassium glutamate 2-Acetamido-2-deoxy-D-glucose D-GlcNAc N-Acetyl-D-glucosamine N-Acetylchitosamine N Acetyl D glucosamine 2 Acetamido 2 deoxy D glucose 2 Acetamido 2 deoxyglucose 2-Acetamido-2-deoxyglucose Acetylglucosamine 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycine N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine N-Choloylglycine 3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine 3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycine N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine Glycocholate Glycine cholate Glycocholic acid, sodium salt Cholylglycine Glycocholate sodium 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycine 3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide 3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycine 3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide Glycoreductodehydrocholic acid Glycylcholate Glycylcholic acid N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amide N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide N-Choloyl-glycine 3-Hydroxy-1,3,5(10)-estratrien-17-one Follicular hormone Folliculin Oestrone (+)-Estrone 1,3,5(10)-Estratrien-3-ol-17-one 3-Hydroxy-17-keto-estra-1,3,5-triene 3-Hydroxyestra-1,3,5(10)-trien-17-one 3-Hydroxyestra-1,3,5(10)-triene-17-one 3-Hydroxyoestra-1,3,5(10)-trien-17-one D1,3,5(10)-Estratrien-3-ol-17-one Estrone, (+-)-isomer Hyrex brand OF estrone Estrone, (9 beta)-isomer Estrovarin Kestrone Wehgen Estrone, (8 alpha)-isomer Hauck brand OF estrone Unigen Vortech brand OF estrone alpha,beta-Hydroxypropionic acid D-GroA R-Glyceric acid Glycerate (R)-Glycerate a,b-Hydroxypropionate a,b-Hydroxypropionic acid alpha,beta-Hydroxypropionate Α,β-hydroxypropionate Α,β-hydroxypropionic acid R-Glycerate (R)-Glyceric acid D-Glycerate D-Glyceric acid (2R)-2,3-Dihydroxypropanoic acid (R)-2,3-Dihydroxypropanoic acid D-2,3-Dihydroxypropanoic acid 1-Amino-2-hydroxyethane 2-Amino-1-ethanol 2-Amino-ethanol 2-Aminoethan-1-ol 2-Aminoethyl alcohol 2-Hydroxyethylamine Aethanolamin Aminoethanol beta-Aminoethanol beta-Aminoethyl alcohol beta-Ethanolamine beta-Hydroxyethylamine Colamine ETA Glycinol Hea MEA MONOETHANOLAMINE b-Aminoethanol Β-aminoethanol b-Aminoethyl alcohol Β-aminoethyl alcohol b-Ethanolamine Β-ethanolamine b-Hydroxyethylamine Β-hydroxyethylamine 2-Aminoethanol 2-Ethanolamine 2-Hydroxyethanamine Envision conditioner PDD 9020 Ethylolamine H-Glycinol Monoaethanolamin Olamine 2 Aminoethanol (3R,4S,5R)-5-[(1R)-1-Carboxy-2,2-difluoro-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylate (1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate (1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid (1S)-2-[(3-O-beta-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid (1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate (1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid C5H9NO4 147.13 147.0532 (2S)-2-aminopentanedioic acid L-glutamic acid 56-86-0 N[C@@H](CCC(O)=O)C(O)=O InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 WHUUTDBJXJRKMK-VKHMYHEASA-N belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Glutamic acid and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Glutamic acid or derivatives Hydrocarbon derivative L-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Amino acids Common amino acids L-alpha-amino acid glutamic acid glutamine family amino acid proteinogenic amino acid water_solubility 8.57 mg/mL logp -3.69 HANSCH,C ET AL. (1995) logp -3.54 ALOGPS logs -0.26 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2S)-2-aminopentanedioic acid ChemAxon average_mass 147.13 ChemAxon mono_mass 147.0532 ChemAxon smiles N[C@@H](CCC(O)=O)C(O)=O ChemAxon formula C5H9NO4 ChemAxon inchi InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 ChemAxon inchikey WHUUTDBJXJRKMK-VKHMYHEASA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 31.29 ChemAxon polarizability 13.32 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00025 DB00142 FDB012535 16015 33032 C00001358 GLT L-Glutamic_Acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Camacho A, Massieu L: Role of glutamate transporters in the clearance and release of glutamate during ischemia and its relation to neuronal death. Arch Med Res. 2006 Jan;37(1):11-8. doi: 10.1016/j.arcmed.2005.05.014. 16314180 Lau A, Tymianski M: Glutamate receptors, neurotoxicity and neurodegeneration. Pflugers Arch. 2010 Jul;460(2):525-42. doi: 10.1007/s00424-010-0809-1. Epub 2010 Mar 14. 20229265 1.0 2020-03-18 23:25:56 UTC 2020-09-11 20:08:56 UTC CDB000131 L-Serine Serine (or L-serine), abbreviated as Ser or S, is a nonessential amino acid derived from glycine. As all amino acid are building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Muscles have low-average concentration of serine compared to other amino acids. . In contrast, serine is highly concentrated in all cell membranes. L-Serine may be derived from four possible sources: dietary intake, biosynthesis from the glycolytic intermediate 3-phosphoglycerate, from glycine, and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of L-serine to serine homoeostasis. It is likely that the predominant source of L-serine varies in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted to serine by a three enzyme cascade. First, 3-phosphoglycerate is converted into phosphohydroxypyruvate by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Second, phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and third, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three biosynthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function (PMID: 12534373). L-serine is also found in Cannabis plants (PMID: 6991645). (2S)-2-Amino-3-hydroxypropanoic acid (S)-(-)-Serine (S)-2-Amino-3-hydroxypropanoic acid (S)-alpha-Amino-beta-hydroxypropionic acid (S)-Serine beta-Hydroxy-L-alanine beta-Hydroxyalanine L-(-)-Serine L-2-Amino-3-hydroxypropionic acid L-3-Hydroxy-2-aminopropionic acid L-3-Hydroxy-alanine L-Ser L-Serin S Ser SERINE (2S)-2-Amino-3-hydroxypropanoate (S)-2-Amino-3-hydroxypropanoate (S)-a-Amino-b-hydroxypropionate (S)-a-Amino-b-hydroxypropionic acid (S)-alpha-Amino-beta-hydroxypropionate (S)-Α-amino-β-hydroxypropionate (S)-Α-amino-β-hydroxypropionic acid b-Hydroxy-L-alanine Β-hydroxy-L-alanine b-Hydroxyalanine Β-hydroxyalanine L-2-Amino-3-hydroxypropionate L-3-Hydroxy-2-aminopropionate (-)-Serine (S)-2-Amino-3-hydroxy-propanoate (S)-2-Amino-3-hydroxy-propanoic acid (S)-b-Amino-3-hydroxypropionate (S)-b-Amino-3-hydroxypropionic acid (S)-beta-Amino-3-hydroxypropionate (S)-beta-Amino-3-hydroxypropionic acid 2-Amino-3-hydroxypropanoate 2-Amino-3-hydroxypropanoic acid 3-Hydroxy-L-alanine L Serine (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol Bo-xan e 161b Xanthophyll (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol C3H7NO3 105.09 105.0426 (2S)-2-amino-3-hydroxypropanoic acid L-serine 6898-95-9 N[C@@H](CO)C(O)=O InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 MTCFGRXMJLQNBG-REOHCLBHSA-N belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Serine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Primary alcohols Alcohol Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Beta-hydroxy acid Carbonyl group Carboxylic acid Hydrocarbon derivative Hydroxy acid L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary alcohol Primary aliphatic amine Primary amine Serine or derivatives Common amino acids L-alpha-amino acid proteinogenic amino acid serine serine family amino acid water_solubility 425.0 mg/mL logp -3.07 HANSCH,C ET AL. (1995) melting_point 228 °C logp -3.42 ALOGPS logs 0.66 ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 2.03 ChemAxon pka_strongest_basic 8.93 ChemAxon iupac (2S)-2-amino-3-hydroxypropanoic acid ChemAxon average_mass 105.09 ChemAxon mono_mass 105.0426 ChemAxon smiles N[C@@H](CO)C(O)=O ChemAxon formula C3H7NO3 ChemAxon inchi InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 ChemAxon inchikey MTCFGRXMJLQNBG-REOHCLBHSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 22.04 ChemAxon polarizability 9.39 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00065 DB00133 FDB012739 5736 5951 17115 SER C00001393 33717 L-serine 5203 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 de Koning TJ, Snell K, Duran M, Berger R, Poll-The BT, Surtees R: L-serine in disease and development. Biochem J. 2003 May 1;371(Pt 3):653-61. doi: 10.1042/BJ20021785. 12534373 1.0 2020-03-18 23:25:58 UTC 2020-09-11 20:08:56 UTC CDB000132 L-Isoleucine L-isoleucine or isoleucine, abbreviated as Ile or I, is one of the essential amino acids used in the biosynthesis of proteins. It contains an Œ±-amino group (which is in the protonated ‚àíNH3+ form under biological conditions), an Œ±-carboxylic acid group (which is in the deprotonated ‚àíCOO‚àí form under biological conditions), and a hydrocarbon side chain with a branch (a central carbon atom bound to three other carbon atoms). It is classified as a non-polar, uncharged (at physiological pH), branched-chain, aliphatic amino acid. In plants and microorganisms, it is synthesized via several steps, starting from pyruvate and alpha-ketobutyrate. Isoleucine is one of the three branched chain amino acids (BCAA), together with leucine and valine. Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. Isoleucine is less concentrated in foods compared to leucine and valine. A cup of milk contains 800 mg of leucine and only 500 mg of isoleucine and valine. A cup of wheat germ has about 1.6 g of leucine and 1 g of isoleucine and valine. Eggs and cheese have about equal amounts of the BCAA and contain about 400 mg of leucine and 400 mg of valine and isoleucine. Pork contains 7 to 8 g of leucine and 3 to 4 g of isoleucine and valine. L-isoleucine is also found in Cannabis plants (PMID: 6991645). These BCAA are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine, and isoleucine, respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; aromatic amino acids (AAA)-tyrosine, tryptophan and phenylalanine, as well as methionine-are increased in these conditions. Valine has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. The BCAA are not without side effects. Leucine alone, for example, exacerbates pellagra and can cause psychosis in pellagra patients by increasing excretion of niacin in the urine. Leucine may lower brain serotonin and dopamine whereas isoleucine may have potential as an antipsychotic treatment. A dose of 3 g of isoleucine added to the niacin regime cleared leucine-aggravated psychosis in schizophrenic patients. Moreover, L-isoleucine is associated with maple syrup urine disease (MSUD; PMID: 10234605), which is an inborn error of metabolism, so named for the sweet, maple syrup smell of urine. MSUD is an autosomal recessive disorder that affects the metabolism of the BCAA. Mutations occur in the 4 genes that comprise the branched-chain alpha-keto acid dehydrogenase complex, which breaks down the BCAA. (2S,3S)-2-Amino-3-methylpentanoic acid 2-Amino-3-methylvaleric acid alpha-Amino-beta-methylvaleric acid I Ile ISOLEUCINE (2S,3S)-2-Amino-3-methylpentanoate 2-Amino-3-methylvalerate a-Amino-b-methylvalerate a-Amino-b-methylvaleric acid alpha-Amino-beta-methylvalerate Α-amino-β-methylvalerate Α-amino-β-methylvaleric acid (2S,3S)-2-Amino-3-methyl-pentanoate (2S,3S)-2-Amino-3-methyl-pentanoic acid (2S,3S)-a-Amino-b-methyl-N-valerate (2S,3S)-a-Amino-b-methyl-N-valeric acid (2S,3S)-a-Amino-b-methylvalerate (2S,3S)-a-Amino-b-methylvaleric acid (2S,3S)-Alph-amino-beta-methylvalerate (2S,3S)-Alph-amino-beta-methylvaleric acid (2S,3S)-alpha-Amino-beta-merthyl-N-valerate (2S,3S)-alpha-Amino-beta-merthyl-N-valeric acid (2S,3S)-alpha-Amino-beta-merthylvalerate (2S,3S)-alpha-Amino-beta-merthylvaleric acid (2S,3S)-alpha-Amino-beta-methyl-N-valerate (2S,3S)-alpha-Amino-beta-methyl-N-valeric acid (2S,3S)-alpha-Amino-beta-methylvalerate (2S,3S)-alpha-Amino-beta-methylvaleric acid (S)-Isoleucine (S,S)-Isoleucine 2-Amino-3-methylpentanoate 2-Amino-3-methylpentanoic acid 2S,3S-Isoleucine Erythro-L-isoleucine Iso-leucine L-(+)-Isoleucine L-Ile [S-(R*,r*)]-2-amino-3-methylpentanoate [S-(R*,r*)]-2-amino-3-methylpentanoic acid Isoleucine, L-isomer Alloisoleucine Isoleucine, L isomer L-Isomer isoleucine 2S-Amino-3S-methylpentanoate L-Isoleucine C6H13NO2 131.17 131.0946 (2S,3S)-2-amino-3-methylpentanoic acid L-isoleucine 73-32-5 CC[C@H](C)[C@H](N)C(O)=O InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 AGPKZVBTJJNPAG-WHFBIAKZSA-N belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Isoleucine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Methyl-branched fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Branched fatty acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative Isoleucine or derivatives L-alpha-amino acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Amino fatty acids Common amino acids L-alpha-amino acid aspartate family amino acid isoleucine proteinogenic amino acid water_solubility 35 mg/mL Human Metabolome Project logp -1.70 HANSCH,C ET AL. (1995) melting_point 285.5 °C logp -1.73 ALOGPS logs -0.06 ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 2.79 ChemAxon pka_strongest_basic 9.59 ChemAxon iupac (2S,3S)-2-amino-3-methylpentanoic acid ChemAxon average_mass 131.17 ChemAxon mono_mass 131.0946 ChemAxon smiles CC[C@H](C)[C@H](N)C(O)=O ChemAxon formula C6H13NO2 ChemAxon inchi InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 ChemAxon inchikey AGPKZVBTJJNPAG-WHFBIAKZSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 34.09 ChemAxon polarizability 14.11 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00407 DB00167 FDB012397 6067 6306 17191 C00001374 ILE 34887 Isoleucine 5193 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Podebrad F, Heil M, Reichert S, Mosandl A, Sewell AC, Bohles H: 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease. J Inherit Metab Dis. 1999 Apr;22(2):107-14. doi: 10.1023/a:1005433516026. 10234605 1.0 2020-03-18 23:26:00 UTC 2020-09-11 20:08:56 UTC CDB000133 L-Leucine Leucine, abbreviated as Leu or L, l-leucine, is an essential amino acid (meaning the body cannot synthesize it and it must be obtained from the diet) that is used in the biosynthesis of proteins. It contains an Œ±-amino group (which is in the protonated ‚àíNH3+ form under biological conditions), an Œ±-carboxylic acid group (which is in the deprotonated ‚àíCOO‚àí form under biological conditions), and a side chain isobutyl group, making it a non-polar aliphatic amino acid. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, beans and legumes. L-Leucine is a branched-chain amino acid (BCAA). BCAAs are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy, and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats, and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg, and 16 mg/kg of valine, leucine, and isoleucine, respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist and are marked by various abnormalities. The most common form is the maple syrup urine disease (PMID: 10234605), marked by a characteristic sweet smell of urine. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting, and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are useful because they are metabolized primarily by muscle and particularly leucine, are most essential for muscle health. BCAA and other amino acids are frequently fed intravenously (TPN) to malnourished surgical patients and, in some cases, those with severe trauma. BCAA, particularly leucine, stimulate protein synthesis, increase reutilization of amino acids in many organs and reduce protein breakdown. Furthermore, leucine can be an important source of calories, and is superior as fuel to the ubiquitous intravenous glucose (dextrose). Leucine also stimulates insulin release, which in turn stimulates protein synthesis and inhibits protein breakdown. These effects are particularly useful in athletic training. BCAA should also replace the use of steroids by weightlifters. Huntington's chorea and anorexic disorders both are characterized by low serum BCAA. These diseases, as well as forms of Parkinson's, may respond to BCAA therapy. L-Leucine can be found in most biofluids, including blood, cerebrospinal fluid (CSF), feces, and sweat, as well as throughout most human tissues. L-Leucine exists in all living species, ranging from bacteria to humans. L-leucine is also found in Cannabis plants (PMID: 6991645). (2S)-2-Amino-4-methylpentanoic acid (2S)-alpha-2-Amino-4-methylvaleric acid (2S)-alpha-Leucine (S)-(+)-Leucine (S)-Leucine 2-Amino-4-methylvaleric acid L L-Leucin L-Leuzin Leu LEUCINE (2S)-2-Amino-4-methylpentanoate (2S)-a-2-Amino-4-methylvalerate (2S)-a-2-Amino-4-methylvaleric acid (2S)-alpha-2-Amino-4-methylvalerate (2S)-Α-2-amino-4-methylvalerate (2S)-Α-2-amino-4-methylvaleric acid (2S)-a-Leucine (2S)-Α-leucine 2-Amino-4-methylvalerate (S)-2-Amino-4-methylpentanoate (S)-2-Amino-4-methylpentanoic acid (S)-2-Amino-4-methylvalerate (S)-2-Amino-4-methylvaleric acid 4-Methyl-L-norvaline L-(+)-Leucine L-a-Aminoisocaproate L-a-Aminoisocaproic acid L-alpha-Aminoisocaproate L-alpha-Aminoisocaproic acid Leucine, L-isomer L-Isomer leucine Leucine, L isomer C6H13NO2 131.17 131.0946 (2S)-2-amino-4-methylpentanoic acid L-leucine 71000-80-1 CC(C)C[C@H](N)C(O)=O InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 ROHFNLRQFUQHCH-YFKPBYRVSA-N belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Leucine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Methyl-branched fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Branched fatty acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Leucine or derivatives Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Common amino acids L-alpha-amino acid leucine proteinogenic amino acid pyruvate family amino acid water_solubility 21.5 mg/mL logp -1.52 HANSCH,C ET AL. (1995) melting_point 268 - 288 °C logp -1.82 ALOGPS logs -0.27 ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 2.79 ChemAxon pka_strongest_basic 9.52 ChemAxon iupac (2S)-2-amino-4-methylpentanoic acid ChemAxon average_mass 131.17 ChemAxon mono_mass 131.0946 ChemAxon smiles CC(C)C[C@H](N)C(O)=O ChemAxon formula C6H13NO2 ChemAxon inchi InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 ChemAxon inchikey ROHFNLRQFUQHCH-YFKPBYRVSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 34.17 ChemAxon polarizability 14.16 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB00149 FDB000899 C00123 5880 15603 6106 LEU C00001377 33942 Leucine 24 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Podebrad F, Heil M, Reichert S, Mosandl A, Sewell AC, Bohles H: 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease. J Inherit Metab Dis. 1999 Apr;22(2):107-14. doi: 10.1023/a:1005433516026. 10234605 1.0 2020-03-18 23:26:03 UTC 2020-09-11 20:08:57 UTC CDB000134 L-Phenylalanine Phenylalanine, abbreviated Phe or F, is a neutral, nonpolar, hydrophobic, essential amino acid. It is the precursor of the amino acid tyrosine, a precursor of the skin pigment melanin and a precursor of catecholamines that include tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma and is found naturally in mammalian breast milk. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in several high protein foods, such as meat, cottage cheese, and wheat germ. Phenylalanine is also found in Cannabis plants (PMID: 6991645). An additional dietary source of phenylalanine is artificial sweeteners containing aspartame. Generally, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Untreated PKU can lead to intellectual disability, seizures, behavioural problems, and mental disorders. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with PKU. PKU patients have elevated serum plasma levels of phenylalanine, up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004). Phenylalanine has been found to interfere with different cerebral enzyme systems. PKU individuals may have a musty smell and lighter skin, likely related to altered conversion of phenylalanine to the skin pigment melanin. Mild phenylketonuria may be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimer's disease and Parkinson's disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200). Phenylalanine also has some potential benefits. Phenylalanine can act as an analgesic, providing relief for premenstrual syndrome and may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS) for Parkinson's patients. Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For some tumours that use more phenylalanine than others (such as melatonin-producing tumours called melanomas) may benefit from low phenylalanine diets. (S)-2-Amino-3-phenylpropionic acid (S)-alpha-Amino-beta-phenylpropionic acid 3-Phenyl-L-alanine beta-Phenyl-L-alanine F Phe PHENYLALANINE (S)-2-Amino-3-phenylpropionate (S)-a-Amino-b-phenylpropionate (S)-a-Amino-b-phenylpropionic acid (S)-alpha-Amino-beta-phenylpropionate (S)-Α-amino-β-phenylpropionate (S)-Α-amino-β-phenylpropionic acid b-Phenyl-L-alanine Β-phenyl-L-alanine (-)-beta-Phenylalanine (L)-Phenylalanine (S)-(-)-Phenylalanine (S)-2-Amino-3-phenylpropanoate (S)-2-Amino-3-phenylpropanoic acid (S)-alpha-Amino-benzenepropanoate (S)-alpha-Amino-benzenepropanoic acid (S)-alpha-Aminobenzenepropanoate (S)-alpha-Aminobenzenepropanoic acid (S)-alpha-Aminohydrocinnamate (S)-alpha-Aminohydrocinnamic acid (S)-Phenylalanine alpha-Aminohydrocinnamate alpha-Aminohydrocinnamic acid beta-Phenyl-alpha-alanine beta-Phenylalanine L-2-Amino-3-phenylpropionate L-2-Amino-3-phenylpropionic acid Phenyl-alanine Phenylalamine L-Isomer phenylalanine Phenylalanine, L isomer Phenylalanine, L-isomer Endorphenyl (6S)-Tetrahydrofolate (6S)-Tetrahydrofolic acid (6S)-THFA 5,6,7,8-Tetrahydrofolate Tetrahydrofolate THF 5,6,7,8-Tetrahydrofolic acid C9H11NO2 165.19 165.079 (2S)-2-amino-3-phenylpropanoic acid L-phenylalanine 5297-02-9 N[C@@H](CC1=CC=CC=C1)C(O)=O InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1 COLNVLDHVKWLRT-QMMMGPOBSA-N belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Phenylalanine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds Amino acids Amphetamines and derivatives Aralkylamines Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Phenylpropanoic acids 3-phenylpropanoic-acid Alpha-amino acid Amine Amino acid Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalanine or derivatives Primary aliphatic amine Primary amine Common amino acids L-alpha-amino acid erythrose 4-phosphate/phosphoenolpyruvate family amino acid phenylalanine proteinogenic amino acid water_solubility 26.9 mg/mL logp -1.38 AVDEEF,A (1997) melting_point 283 °C logp -1.35 ALOGPS logs -1.60 ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 2.47 ChemAxon pka_strongest_basic 9.45 ChemAxon iupac (2S)-2-amino-3-phenylpropanoic acid ChemAxon average_mass 165.19 ChemAxon mono_mass 165.079 ChemAxon smiles N[C@@H](CC1=CC=CC=C1)C(O)=O ChemAxon formula C9H11NO2 ChemAxon inchi InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1 ChemAxon inchikey COLNVLDHVKWLRT-QMMMGPOBSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 45.12 ChemAxon polarizability 17.03 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00079 5910 DB00120 FDB004940 6140 17295 PHE C00001386 Phenylalanine 33775 28 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 van Spronsen FJ, Hoeksma M, Reijngoud DJ: Brain dysfunction in phenylketonuria: is phenylalanine toxicity the only possible cause? J Inherit Metab Dis. 2009 Feb;32(1):46-51. doi: 10.1007/s10545-008-0946-2. Epub 2009 Jan 13. 19191004 Adler-Abramovich L, Vaks L, Carny O, Trudler D, Magno A, Caflisch A, Frenkel D, Gazit E: Phenylalanine assembly into toxic fibrils suggests amyloid etiology in phenylketonuria. Nat Chem Biol. 2012 Aug;8(8):701-6. doi: 10.1038/nchembio.1002. Epub 2012 Jun 17. 22706200 1.0 2020-03-18 23:26:05 UTC 2020-09-11 20:08:56 UTC CDB000135 L-Threonine Threonine, abbreviated Thr or T, is an essential amino acid in humans. It has a side chain containing a¬†hydroxyl group, making it a polar, uncharged amino acid Threonine is catabolized in mammals largely (70-80%) by threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate (which forms glycine and acetyl CoA), and much less by threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia. It is highly concentrated in meat products, cottage cheese and wheat germ. L-Threonine is also found in Cannabis plants (PMID: 6991645). It is abundant in human plasma, particularly in newborns. The threonine content of most infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Premature infants fed these formulas have twice the plasma threonine concentrations of breast-fed infants. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided (PMID: 9853925). Threonine is an immunostimulant which promotes the growth of thymus gland and probably promotes cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 g per day. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals (2S)-Threonine (2S,3R)-(-)-Threonine (2S,3R)-2-Amino-3-hydroxybutanoic acid 2-Amino-3-hydroxybutyric acid L-(-)-Threonine L-2-Amino-3-hydroxybutyric acid L-alpha-Amino-beta-hydroxybutyric acid L-Threonin T Thr THREONINE (2S,3R)-2-Amino-3-hydroxybutanoate 2-Amino-3-hydroxybutyrate L-2-Amino-3-hydroxybutyrate L-a-Amino-b-hydroxybutyrate L-a-Amino-b-hydroxybutyric acid L-alpha-Amino-beta-hydroxybutyrate L-Α-amino-β-hydroxybutyrate L-Α-amino-β-hydroxybutyric acid (2S,3R)-2-Amino-3-hydroxybutyrate (2S,3R)-2-Amino-3-hydroxybutyric acid (R-(R*,s*))-2-amino-3-hydroxybutanoate (R-(R*,s*))-2-amino-3-hydroxybutanoic acid (S)-Threonine 2-Amino-3-hydroxybutanoate 2-Amino-3-hydroxybutanoic acid Threonin [R-(R*,s*)]-2-amino-3-hydroxy-butanoate [R-(R*,s*)]-2-amino-3-hydroxy-butanoic acid [R-(R*,s*)]-2-amino-3-hydroxybutanoate [R-(R*,s*)]-2-amino-3-hydroxybutanoic acid L Threonine C4H9NO3 119.12 119.0582 (2S,3R)-2-amino-3-hydroxybutanoic acid L-threonine 72-19-5 C[C@@H](O)[C@H](N)C(O)=O InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 AYFVYJQAPQTCCC-GBXIJSLDSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Secondary alcohols Short-chain hydroxy acids and derivatives Alcohol Aliphatic acyclic compound Amine Amino acid Beta-hydroxy acid Carbonyl group Carboxylic acid Fatty acid Hydrocarbon derivative Hydroxy acid L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary alcohol Short-chain hydroxy acid Common amino acids L-alpha-amino acid aspartate family amino acid proteinogenic amino acid threonine water_solubility 97.0 mg/mL logp -2.94 HANSCH,C ET AL. (1995) melting_point 256 °C logp -3.01 ALOGPS logs 0.60 ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 2.21 ChemAxon pka_strongest_basic 9 ChemAxon iupac (2S,3R)-2-amino-3-hydroxybutanoic acid ChemAxon average_mass 119.12 ChemAxon mono_mass 119.0582 ChemAxon smiles C[C@@H](O)[C@H](N)C(O)=O ChemAxon formula C4H9NO3 ChemAxon inchi InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 ChemAxon inchikey AYFVYJQAPQTCCC-GBXIJSLDSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 26.46 ChemAxon polarizability 11.08 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00188 DB00156 FDB011999 6051 6288 16857 THR C00001394 Threonine 34186 32 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Boehm G, Cervantes H, Georgi G, Jelinek J, Sawatzki G, Wermuth B, Colombo JP: Effect of increasing dietary threonine intakes on amino acid metabolism of the central nervous system and peripheral tissues in growing rats. Pediatr Res. 1998 Dec;44(6):900-6. doi: 10.1203/00006450-199812000-00013. 9853925 1.0 2020-03-18 23:26:07 UTC 2020-09-11 20:08:56 UTC CDB000136 L-Valine Valine, abbreviated as Val or V, one of 20 proteinogenic amino acids, is a non-polar amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. Valine is an essential amino acid that humans do not synthesize and must acquire from diet, usually from protein sources. Along with leucine and isoleucine, valine is a branched-chain amino acid (BCAA), an amino acid whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine, and isoleucine, respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. Many types of inborn errors of BCAA metabolism exist and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a sweet urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; aromatic amino acids (AAA) tyrosine, tryptophan and phenylalanine, as well as methionine are increased in these conditions. Valine has been established as a useful supplemental therapy for an ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. In sickle-cell disease, the hydrophobic amino acid valine replaces the hydrophilic amino acid glutamic acid in beta-globin, causing it to misfold. The sickle cell hemoglobin is thus prone to aggregation. Hypervalinemia is another example of an inborn error of metabolism involving valine, not the other BCAA. It is caused by a deficiency in the valine transaminase gene (PMID: 6067402). As with most amino acids, L-valine is also found in Cannabis plants (PMID: 6991645). (2S)-2-Amino-3-methylbutanoic acid (S)-Valine 2-Amino-3-methylbutyric acid L-(+)-alpha-Aminoisovaleric acid L-alpha-Amino-beta-methylbutyric acid L-Valin V Val VALINE (2S)-2-Amino-3-methylbutanoate 2-Amino-3-methylbutyrate L-(+)-a-Aminoisovalerate L-(+)-a-Aminoisovaleric acid L-(+)-alpha-Aminoisovalerate L-(+)-Α-aminoisovalerate L-(+)-Α-aminoisovaleric acid L-a-Amino-b-methylbutyrate L-a-Amino-b-methylbutyric acid L-alpha-Amino-beta-methylbutyrate L-Α-amino-β-methylbutyrate L-Α-amino-β-methylbutyric acid (S)-2-Amino-3-methyl-butanoate (S)-2-Amino-3-methyl-butanoic acid (S)-2-Amino-3-methylbutanoate (S)-2-Amino-3-methylbutanoic acid (S)-2-Amino-3-methylbutyrate (S)-2-Amino-3-methylbutyric acid (S)-a-Amino-b-methylbutyrate (S)-a-Amino-b-methylbutyric acid (S)-alpha-Amino-beta-methylbutyrate (S)-alpha-Amino-beta-methylbutyric acid 2-Amino-3-methylbutanoate 2-Amino-3-methylbutanoic acid L Valine C5H11NO2 117.15 117.079 (2S)-2-amino-3-methylbutanoic acid L-valine 72-18-4 CC(C)[C@H](N)C(O)=O InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1 KZSNJWFQEVHDMF-BYPYZUCNSA-N belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Valine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives L-alpha-amino acids Methyl-branched fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Branched fatty acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Valine or derivatives Common amino acids L-alpha-amino acid proteinogenic amino acid pyruvate family amino acid valine water_solubility 58.5 mg/mL logp -2.26 HANSCH,C ET AL. (1995) melting_point 295 - 300 °C logp -2.29 ALOGPS logs 0.26 ALOGPS logp -2 ChemAxon pka_strongest_acidic 2.72 ChemAxon pka_strongest_basic 9.6 ChemAxon iupac (2S)-2-amino-3-methylbutanoic acid ChemAxon average_mass 117.15 ChemAxon mono_mass 117.079 ChemAxon smiles CC(C)[C@H](N)C(O)=O ChemAxon formula C5H11NO2 ChemAxon inchi InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1 ChemAxon inchikey KZSNJWFQEVHDMF-BYPYZUCNSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 29.49 ChemAxon polarizability 12.19 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004905 6050 6287 C00183 16414 DB00161 VAL C00001398 34167 L-valine 5842 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Dancis J, Hutzler J, Tada K, Wada Y, Morikawa T, Arakawa T: Hypervalinemia. A defect in valine transamination. Pediatrics. 1967 Jun;39(6):813-7. 6067402 1.0 2020-03-18 23:26:09 UTC 2020-08-04 22:28:04 UTC CDB000137 D-manno-2-Heptulose 1,3,4,5,6,7-Hexahydroxyheptan-2-one, D-manno-2-Heptulose or mannoheptulose belongs to the class of organic compounds known as heptoses. Heptoses are monosaccharides with seven carbon atoms in their structure. D-manno-2-heptulose is one of the few naturally occurring heptoses found primarily in alfalfa, avocados, and primrose (PMID: 31293606). D-manno-2-heptulose is also found in cannabis plants (PMID: 6991645). Though the carbohydrate is thought to be produced during photosynthesis, the precise biological pathway for the synthesis of mannoheptulose is still unknown. Like other sugars, it is transported in the plant through the phloem. Because it inhibits glycolysis in vitro, it has been investigated as a novel nutraceutical for weight management in dogs. However, while it is suggested that mannoheptulose affects the energy balance of adult dogs, research is still inconclusive regarding the significance of the alteration of energy expenditure in dogs (PMID: 26479244, PMID: 26656105, PMID: 28444793). C7H14O7 210.18 210.074 (3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one (3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5+,6-,7+/m0/s1 HSNZZMHEPUFJNZ-HTPUFBNKSA-N logp -2.38 ALOGPS logs 0.03 ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 8.91 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one ChemAxon average_mass 210.18 ChemAxon mono_mass 210.074 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO ChemAxon formula C7H14O7 ChemAxon inchi InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5+,6-,7+/m0/s1 ChemAxon inchikey HSNZZMHEPUFJNZ-HTPUFBNKSA-N ChemAxon polar_surface_area 138.45 ChemAxon refractivity 43.52 ChemAxon polarizability 18.99 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 25791640 Pedreschi R, Uarrota V, Fuentealba C, Alvaro JE, Olmedo P, Defilippi BG, Meneses C, Campos-Vargas R: Primary Metabolism in Avocado Fruit. Front Plant Sci. 2019 Jun 26;10:795. doi: 10.3389/fpls.2019.00795. eCollection 2019. 31293606 McKnight LL, Eyre R, Gooding MA, Davenport GM, Shoveller AK: Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs. Animals (Basel). 2015 Jun 16;5(2):442-54. doi: 10.3390/ani5020365. 26479244 McKnight LL, Root-McCaig J, Wright D, Davenport GM, France J, Shoveller AK: Dietary Mannoheptulose Does Not Significantly Alter Daily Energy Expenditure in Adult Labrador Retrievers. PLoS One. 2015 Dec 11;10(12):e0143324. doi: 10.1371/journal.pone.0143324. eCollection 2015. 26656105 McKnight LL, France J, Wright D, Davenport G, Shoveller AK: Dietary mannoheptulose does not alter glucose or lipid metabolism in adult Labrador Retrievers. J Anim Physiol Anim Nutr (Berl). 2018 Feb;102(1):e122-e131. doi: 10.1111/jpn.12713. Epub 2017 Apr 26. 28444793 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:12 UTC 2020-08-04 22:28:05 UTC CDB000138 D-Mannose Mannose or D-Mannose, also known as mannopyranose or carubinose, is a C-2 epimer of glucose. It belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a six-carbon containing moeity. Mannose contains an aldehyde group and is therefore referred to as an aldohexose. Mannose commonly exists with two different-sized rings, the pyranose (six-membered) form and the furanose (five-membered) form. Each ring closure can have either an alpha or beta configuration at the anomeric position. Therefore, mannose exists in four different forms. The Œ±‚Äêform of D‚ÄêMannose is mild and sweet, whereas the Œ≤‚Äêform is bitter. Hence, D‚Äêmannose is sweet with a bitter aftertaste. D-mannose is 0.6 times as sweet as sucrose. Sweetness is detected through the binding of sugars to the T1R3 and T1R2 proteins, to form a G-protein coupled receptor that is the sweetness receptor in mammals. D-Mannose is a hydrophilic, neutral molecule that is highly water soluble. It exists as a white crystalline powder. Mannose can be formed by the oxidation of mannitol. Because mannose is a glucose epimer, it can also be naturally produced in a wide range of organisms from glucose or fructose using D-mannose isomerases or D-xylose isomerases. The origin of the name mannose comes from the Hebrew word ‚Äúmanna‚Äù or food (https://doi.org/10.1111/1541-4337.12211). Several trees and shrubs can produce a substance called manna, such as the ‚Äúmanna tree‚Äù from whose secretions mannitol was originally isolated. Mannose is an important component of polysaccharides and glycoproteins. Mannose is the dominant monosaccharide in the N-linked glycosylation of proteins in both plants and animals. Several congenital disorders of glycosylation are associated with mutations in enzymes involved in mannose metabolism (PMID: 20363348). Normally in those mammalian proteins that are glycosylated, the mannose moieties are shielded by galactose, sialic acid or GlcNAc groups. This is important, as the innate immune system in mammals is geared to recognise exposed mannose residues. Many yeasts and viruses (including the AIDS virus) are decorated with exposed mannans or mannose residues, which generates a strong innate immune response. In particular, Mannose-binding lectin (MBL) is an important constituent of the innate immune system. This protein binds through multiple lectin domains to the repeating sugar arrays that decorate many microbial surfaces and is then able to activate the complement system through a specific protease called MBL-associated protease-2. The digestion of many polysaccharides and glycoproteins by humans and other organisms yields mannose, which is phosphorylated by hexokinase to generate mannose-6-phosphate. Mannose-6-phosphate is then converted to fructose-6-phosphate, by the enzyme phosphomannose isomerase, and then enters the glycolytic pathway. The primary pathway for the formation of L-fucose in prokaryotic and eukaryotic cells is from D-mannose via an internal oxidation-reduction and then epimerization of GDP-D-mannose to produce GDP-L-fucose (PMID: 9488699, 16154739, 11414367 ). D-Mannose or Mannose is found in many plants or plant foods where it occurs as a component of mannan, hemicellulose, or cellulose in various cell wall architectures. Individual D-Mannose units can be generated from the decomposition of hemicelluloses by extracellular xylanases. The content of D-mannose reaches up to 21.2% dry weight (DW) in spent coffee grounds. Likewise, jujube powder has up to 12.9% D-mannose. Other plants or plant components with high levels of Mannose include orange peel, litchi pericarp, cranberries, apples, mangoes and peaches. Soybean, kidney bean, sword bean, peanut, and other leguminous plants contain plenty of lectin, which is a glycoprotein containing 3.8% neutral carbohydrates including D-mannose. D-Mannose is also found in Cannabis plants (PMID: 6991645). Mannose (D-mannose) can be used as a nutritional supplement to prevent recurrent urinary tract infections. D-Mannose appears to stop certain bacteria from sticking to the bladder walls by blocking the interaction of the FimH protein on bacterial pili (PMID: 23633128). D-Mannose has been widely used in the food, pharmaceutical, and poultry industries, acting as the source of dietary supplements, starting material for the synthesis of drugs and blocking colonization in animal feeds ( https://doi.org/10.1111/1541-4337.12211). D-Mannose is able to stimulate insulin secretion. The Œ±‚Äêanomer of D‚Äêmannose is better able than the Œ≤‚Äêanomer to stimulate insulin release. D‚ÄêMannose is well metabolized in pancreatic islets of Langerhans and is known to penetrate the blood‚Äìbrain barrier. When mannan is incorporated into a diet, a number of interesting effects are observed, including a decrease in appetite and a reduction in S‚Äêglucose and cholesterol absorption (https://doi.org/10.1111/1541-4337.12211) alpha-D-Man a-D-Man α-D-Man a-D-Mannose α-D-Mannose alpha-D-Mannopyranose a-D-Mannopyranose α-D-Mannopyranose (+)-Mannose Carubinose D(+)-Mannose Mannose Seminose alpha-D-Mannose alpha-Mannose α-Mannose C6H12O6 180.16 180.0634 (2S,3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol α-D-mannose 29696-75-1 OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6+/m1/s1 WQZGKKKJIJFFOK-PQMKYFCFSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol D-mannopyranose water_solubility 713.0 mg/mL at 17 °C melting_point 132 °C logp -2.57 ALOGPS logs 0.64 ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6+/m1/s1 ChemAxon inchikey WQZGKKKJIJFFOK-PQMKYFCFSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.13 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001202 161434 C00936 185698 28729 MANNOSE C00001126 Mannose Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Ito Y, Hagihara S, Matsuo I, Totani K: Structural approaches to the study of oligosaccharides in glycoprotein quality control. Curr Opin Struct Biol. 2005 Oct;15(5):481-9. doi: 10.1016/j.sbi.2005.08.012. 16154739 Yoshida Y: Lectin-Type Ubiquitin Ligase Subunits: Fbs Proteins and Their Applications for Use. Methods Mol Biol. 2020;2132:215-224. doi: 10.1007/978-1-0716-0430-4_22. 32306330 Freeze HH, Sharma V: Metabolic manipulation of glycosylation disorders in humans and animal models. Semin Cell Dev Biol. 2010 Aug;21(6):655-62. doi: 10.1016/j.semcdb.2010.03.011. Epub 2010 Apr 2. 20363348 Park SH, Pastuszak I, Drake R, Elbein AD: Purification to apparent homogeneity and properties of pig kidney L-fucose kinase. J Biol Chem. 1998 Mar 6;273(10):5685-91. doi: 10.1074/jbc.273.10.5685. 9488699 Jack DL, Klein NJ, Turner MW: Mannose-binding lectin: targeting the microbial world for complement attack and opsonophagocytosis. Immunol Rev. 2001 Apr;180:86-99. doi: 10.1034/j.1600-065x.2001.1800108.x. 11414367 Kranjcec B, Papes D, Altarac S: D-mannose powder for prophylaxis of recurrent urinary tract infections in women: a randomized clinical trial. World J Urol. 2014 Feb;32(1):79-84. doi: 10.1007/s00345-013-1091-6. Epub 2013 Apr 30. 23633128 1.0 2020-03-18 23:26:14 UTC 2020-07-24 23:30:06 UTC CDB000139 Aldehydo-L-rhamnose Aldehydo-L-rhamnose belongs to the class of organic compounds known as hexoses. It is the open chain aldehyde form of D-rhamnose. Hexoses are monosaccharides in which the sugar unit is a six-carbon containing moiety. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Aldehydo-L-rhamnose is a neutral compound. It is an odorless white powder with a sweet taste ( http://www.thegoodscentscompany.com/data/rw1037731.html#tophyp ). Rhamnose (Rha, Rham) is a naturally occurring L-form deoxy sugar. This is unusual, since most of the naturally occurring sugars are in D-form. It is found in banana, guava, plum, onion, okra, olive and garlic bulb; in caraway, sunflower, flax and coconut seeds; in coffee beans and in fig and tarragon leaves ( http://www.thegoodscentscompany.com/data/rw1037731.html#tooccur). Rhamnose is methyl-pentose also found in Cannabis plants (PMID: 6991645). (2R,3R,4S,5S)-2,3,4,5-Tetrahydroxyhexanal L-Rha L-Rhamnose Deoxymannose Rhamnose Rhamnose, L isomer Rhamnose, L-isomer C6H12O5 164.16 164.0685 (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal 6-deoxy-L-mannose 4469-18-5 C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 PNNNRSAQSRJVSB-BXKVDMCESA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha-hydroxyaldehydes Beta-hydroxy aldehydes Hydrocarbon derivatives Medium-chain aldehydes Organic oxides Polyols Secondary alcohols Alcohol Aldehyde Aliphatic acyclic compound Alpha-hydroxyaldehyde Beta-hydroxy aldehyde Carbonyl group Hexose monosaccharide Hydrocarbon derivative Medium-chain aldehyde Organic oxide Polyol Secondary alcohol L-rhamnose aldehyde logp -2.02 ALOGPS logs 0.20 ALOGPS logp -2.5 ChemAxon pka_strongest_acidic 12.31 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal ChemAxon average_mass 164.16 ChemAxon mono_mass 164.0685 ChemAxon smiles C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O ChemAxon formula C6H12O5 ChemAxon inchi InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1 ChemAxon inchikey PNNNRSAQSRJVSB-BXKVDMCESA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 35.8 ChemAxon polarizability 15.24 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB02961 19233 16055 Rhamnose Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:16 UTC 2020-07-24 23:30:15 UTC CDB000140 Beta-D-Ribopyranose beta-D-Ribopyranose, also known as ribose or D-ribopyranose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. beta-D-Ribopyranose is neutral compound. Beta-D-Ribopyranose is one of five cyclic forms of D-ribose. D-Ribose, commonly referred to as simply ribose, is a five-carbon sugar found in all living cells. Ribose is not an essential nutrient because it can be synthesized by almost every tissue in the body from other substances, such as glucose. It is vital for life as a component of DNA, RNA, ATP, ADP, and AMP. In nature, small amounts of ribose can be found in ripe fruits and vegetables. Brewer's yeast, which has a high concentration of RNA, is another rich source of ribose. D-ribose is also a component of many so-called energy drinks and anti-aging products available on the market today. Ribose is a structural component of ATP, which is the primary energy source for exercising muscle. The adenosine component is an adenine base attached to the five-carbon sugar ribose. ATP provides energy to working muscles by releasing a phosphate group, hence becoming ADP, which in turn may release a phosphate group, then becoming AMP. During intense muscular activity, the total amount of ATP available is quickly depleted. To correct this imbalance, AMP is broken down in the muscle and secreted from the cell. Once the breakdown products of AMP are released from the cell, the energy potential (TAN pool) of the muscle is reduced and ATP must then be reformed using ribose. Ribose helps to restore the level of adenine nucleotides by bypassing the rate-limiting step in the de novo (oxidative pentose phosphate) pathway, which regenerates phosphoribosyl pyrophosphate (PRPP), the essential precursor for ATP. If ribose is not readily available to a cell, glucose may be converted to ribose. Ribose supplementation has been shown to increase the rate of ATP resynthesis following intense exercise. The use of ribose in men with severe coronary artery disease resulted in improved exercise tolerance. Hence, there is interest in the potential of ribose supplements to boost muscular performance in athletic activities (PMID: 17618002). beta-D-Ribopyranose is pentose also found in Cannabis plants (PMID: 6991645). Ribose RIBOSE(pyranose form) b-D-Ribopyranose Β-D-ribopyranose D-Ribose C5H10O5 150.13 150.0528 (2R,3R,4R,5R)-oxane-2,3,4,5-tetrol β-D-ribopyranose 7296-60-8 O[C@@H]1CO[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4-,5-/m1/s1 SRBFZHDQGSBBOR-TXICZTDVSA-N belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Pentoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Hemiacetal Hydrocarbon derivative Organoheterocyclic compound Oxacycle Oxane Pentose monosaccharide Polyol Secondary alcohol D-ribopyranose logp -2.57 ALOGPS logs 0.91 ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,3R,4R,5R)-oxane-2,3,4,5-tetrol ChemAxon average_mass 150.13 ChemAxon mono_mass 150.0528 ChemAxon smiles O[C@@H]1CO[C@@H](O)[C@H](O)[C@@H]1O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4-,5-/m1/s1 ChemAxon inchikey SRBFZHDQGSBBOR-TXICZTDVSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 29.96 ChemAxon polarizability 13.39 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04286 FDB028843 441481 27476 C08353 Dhanoa TS, Housner JA: Ribose: more than a simple sugar? Curr Sports Med Rep. 2007 Jul;6(4):254-7. doi: 10.1007/s11932-007-0041-8. 17618002 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:18 UTC 2020-08-04 22:28:05 UTC CDB000141 D-Xylose Xylose or wood sugar is an aldopentose, a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40% as sweet as sucrose. It is a white powder with a smoky odor and a smoky¬†sweet¬†salty¬†coffee taste ( http://www.thegoodscentscompany.com/data/rw1005221.html#tophyp). The polysaccharide xylan, a hemi-cellulose, consists almost entirely of D-xylose. Xylan is found in 30 % of most plants. Xylose, though, is pervasive as it is found in the embryos of most edible plants. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar as well as the plants of apple, apricot, caper, celery, fenugreek and wheat. It is found in apple, banana, grape, guava, orange, raspberry and plum ( http://www.thegoodscentscompany.com/data/rw1005221.html#tooccur). Xylose in the urine is a biomarker for the consumption of apples and other fruits. Xylose is also found in mucopolysaccharides of connective tissue. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore, xylose is involved in the biosynthetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate. In medicine, xylose is used to test for malabsorption by administering a xylose solution to the patient after fasting. If xylose is detected in the blood and/or urine within the next few hours, it has been absorbed by the intestines. Xylose is said to be one of eight sugars which are essential for human nutrition, the others including galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. Being part of the cell wall of most plants, xylan and xylose are also found in Cannabis sativa tissue (PMID: 6991645). C5H10O5 150.13 150.0528 (2R,3R,4S,5R)-oxane-2,3,4,5-tetrol β-D-xylose 2460-44-8 O[C@@H]1CO[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5-/m1/s1 SRBFZHDQGSBBOR-KKQCNMDGSA-N belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Pentoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Hemiacetal Hydrocarbon derivative Organoheterocyclic compound Oxacycle Oxane Pentose monosaccharide Polyol Secondary alcohol D-xylopyranose logp -2.57 ALOGPS logs 0.91 ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,3R,4S,5R)-oxane-2,3,4,5-tetrol ChemAxon average_mass 150.13 ChemAxon mono_mass 150.0528 ChemAxon smiles O[C@@H]1CO[C@@H](O)[C@H](O)[C@H]1O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5-/m1/s1 ChemAxon inchikey SRBFZHDQGSBBOR-KKQCNMDGSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 29.96 ChemAxon polarizability 13.43 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 125409 28161 C02096 FDB031294 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:21 UTC 2020-08-04 22:28:07 UTC CDB000142 D-arabitol D-Arabitol or D-arabinitol, also known as klinit or lyxitol, belongs to the class of organic compounds known as sugar alcohols, a type of polyols. These are hydrogenated forms of carbohydrates in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. A polyol is an organic compound containing many hydroxyls. D-Arabitol is neutral compound. D-Arabitol is one of the sugar alcohols and cyclitols found in cannabis plant (PMID: 6991645). Polyols, classified by the number of carbon atoms and include the sugar alcohols, are linked to the pentose phosphate pathway (PPP). The PPP generates¬†NADPH¬†and¬†pentoses¬†(5-carbon¬†sugars) as well as¬†ribose 5-phosphate, a precursor for the synthesis of¬†nucleotides. While the pentose phosphate pathway oxidizes¬†glucose, its primary role is¬†anabolic¬†rather than¬†catabolic. Polyols, including D-arabitol, accumulates in body fluids in individuals with two defects in PPP, involving the enzymes ribose-5-phosphate isomerase (RPI) and transaldolase (PMID: 18987987). A patient with leukoencephalopathy and peripheral neuropathy, with a strong brain-CSF-plasma gradient of C5 polyols such as D-arabitol, was identified as suffering from RPI deficiency. Another patient displaying mainly liver problems and increased concentrations of polyols, mainly D-arabitol, was diagnosed with transaldolase deficiency. However, the mechanism of pathophysiology of polyols in patients with defects in the PPP is poorly understood. It is thought that D-arabitol is a metabolic end-product in humans. The mechanisms of brain and neuronal damage in RPI deficiency may result from polyol accumulation, causing secondary brain dysfunction (PMID: 16435225). D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway. D-Arabitol accumulated in a Penicillium rubens strain deleted of four highly expressed biosynthetic gene clusters that produce penicillin, roquefortine, chrysogine and fungisporin. The transcriptome of the P. rubens strain had changed when the gene cluster was removed, resulting in increased expression of D-arabinitol 4-dehydrogenase (PMID: 32376967). D-Arabitol, a fungal metabolite, is used as a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861; PMID: 10647119). It is also a metabolite of Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659). D-Arabinol D-Lyxitol D-Arabinitol Arabitol, (D)-isomer Arabitol D-(+)-Arabitol (+--)-Arabitol DL-Arabitol Arabino-pentitol Lyxitol D-Arabitol C5H12O5 152.15 152.0685 (2R,4R)-pentane-1,2,3,4,5-pentol arabitol 488-81-3 OC[C@H](O)[C@H](O)[C@H](O)CO InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- HEBKCHPVOIAQTA-ZXFHETKHSA-N belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sugar alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Hydrocarbon derivatives Monosaccharides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Monosaccharide Polyol Primary alcohol Secondary alcohol Sugar alcohol arabinitol water_solubility 936 mg/mL melting_point 102 - 105 °C logp -2.53 ALOGPS logs 0.64 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 12.76 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,4R)-pentane-1,2,3,4,5-pentol ChemAxon average_mass 152.15 ChemAxon mono_mass 152.0685 ChemAxon smiles OC[C@H](O)[C@H](O)[C@H](O)CO ChemAxon formula C5H12O5 ChemAxon inchi InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- ChemAxon inchikey HEBKCHPVOIAQTA-ZXFHETKHSA-N ChemAxon polar_surface_area 101.15 ChemAxon refractivity 32.44 ChemAxon polarizability 14.28 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01904 94154 FDB001475 84971 18333 C00001156 D-arabinitol 5551 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Pohl C, Polli F, Schutze T, Viggiano A, Mozsik L, Jung S, de Vries M, Bovenberg RAL, Meyer V, Driessen AJM: A Penicillium rubens platform strain for secondary metabolite production. Sci Rep. 2020 May 6;10(1):7630. doi: 10.1038/s41598-020-64893-6. 32376967 Wamelink MM, Struys EA, Jakobs C: The biochemistry, metabolism and inherited defects of the pentose phosphate pathway: a review. J Inherit Metab Dis. 2008 Dec;31(6):703-17. doi: 10.1007/s10545-008-1015-6. Epub 2008 Nov 8. 18987987 Klusmann A, Fleischer W, Waldhaus A, Siebler M, Mayatepek E: Influence of D-arabitol and ribitol on neuronal network activity. J Inherit Metab Dis. 2005;28(6):1181-3. doi: 10.1007/s10545-005-0073-2. 16435225 Hui M, Cheung SW, Chin ML, Chu KC, Chan RC, Cheng AF: Development and application of a rapid diagnostic method for invasive Candidiasis by the detection of D-/L-arabinitol using gas chromatography/mass spectrometry. Diagn Microbiol Infect Dis. 2004 Jun;49(2):117-23. doi: 10.1016/j.diagmicrobio.2004.02.006. 15183861 Christensson B, Sigmundsdottir G, Larsson L: D-arabinitol--a marker for invasive candidiasis. Med Mycol. 1999 Dec;37(6):391-6. doi: 10.1046/j.1365-280x.1999.00249.x. 10647119 Kordowska-Wiater M: Production of arabitol by yeasts: current status and future prospects. J Appl Microbiol. 2015 Aug;119(2):303-14. doi: 10.1111/jam.12807. Epub 2015 Apr 8. 25809659 1.0 2020-03-18 23:26:23 UTC 2020-08-04 22:28:10 UTC CDB000143 Levoinositol Levoinositol (also known as 1L-chiro-Inositol or L-chiro-inositol, abbreviated LCI) is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, with the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. Levoinositol is found in dandelion and is widely distributed in higher plants predominantly as its monomethyl ether. Levoinositol is one of the sugar alcohols found in cannabis plant (PMID: 6991645). It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. Inositol phospholipids are important in signal transduction. A possible health effect of inositols, including chiro-inositol, was recently reviewed. The review concluded that myo-inositol, together with chiro-inositol, at a 40:1 ratio, were an important therapeutic strategy for the improvement of metabolic, hormonal, and reproductive aspects of polycystic ovarian syndrome (PMID: 29309199). (+)-Inositol (1R,2R,3S,4S,5S,6S)-Cyclohexane-1,2,3,4,5,6-hexol 1,2,4/3,5,6-cyclohexanehexol cis-1,2,4-trans-3,5,6-Cyclohexanehexol D-Inositol DCI 1,2,4/3,5,6-cyclohexane-1,2,3,4,5,6-hexol (+)-Chiro-inositol 1D-Chiro-inositol D-(+)-Chiro-inositol D-chiro-Inositol C6H12O6 180.16 180.0634 (1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol D-chiro-inositol 643-12-9 O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1 CDAISMWEOUEBRE-LKPKBOIGSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Hydrocarbon derivatives Polyols Sugar alcohols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Hydrocarbon derivative Polyol Sugar alcohol chiro-inositol logp -2.59 ALOGPS logs 0.43 ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 12.29 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexol ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1 ChemAxon inchikey CDAISMWEOUEBRE-LKPKBOIGSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 35.78 ChemAxon polarizability 16.1 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001138 10254647 27372 C19891 1D-chiro-Inositol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Gateva A, Unfer V, Kamenov Z: The use of inositol(s) isomers in the management of polycystic ovary syndrome: a comprehensive review. Gynecol Endocrinol. 2018 Jul;34(7):545-550. doi: 10.1080/09513590.2017.1421632. Epub 2018 Jan 8. 29309199 1.0 2020-03-18 23:26:25 UTC 2020-08-04 22:28:10 UTC CDB000144 Myoinositol Myo-Inositol is an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It also is known as a sugar alcohol, having the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol, and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. It is found in many foods, particularly in cereals with high bran content. Inositol is one of the sugar alcohols and cyclitols identified in Cannabis sativa plants (PMID: 6991645). It is an isomer of glucose that has traditionally been a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. Inositol phospholipids are important in signal transduction. A possible health effect of inositols, including myo-inositol, was recently reviewed. The review concluded that myo-inositol, together with chiro-inositol, at a 40:1 ratio, were an important therapeutic strategy for the improvement of metabolic, hormonal, and reproductive aspects of polycystic ovarian syndrome (PMID: 29309199). (1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexol 1,2,3,4,5,6-HEXAHYDROXY-cyclohexane 1,2,3,5/4,6-cyclohexanehexol 1D-Myo-inositol 1l-Myo-inositol Bios I cis-1,2,3,5-trans-4,6-Cyclohexanehexol Cyclohexitol D-Myo-inositol Dambose I-inositol Inosite Inositol Ins L-Myo-inositol Meat sugar Meso-inositol Myoinositol Inosital Iso-inositol MI Myoinosite Phaseomannite Rat antispectacled eye factor Myo inositol Vitamin b8 Myo-inositol C6H12O6 180.16 180.0634 (1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol L-inositol 87-89-8 O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6- CDAISMWEOUEBRE-GPIVLXJGSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Hydrocarbon derivatives Polyols Sugar alcohols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Hydrocarbon derivative Polyol Sugar alcohol inositol water_solubility 143 mg/mL at 19 °C Human Metabolome Project melting_point 225 °C logp -2.59 ALOGPS logs 0.43 ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 12.29 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6- ChemAxon inchikey CDAISMWEOUEBRE-GPIVLXJGSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 35.78 ChemAxon polarizability 16.14 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00137 FDB010547 DB13178 10239179 17268 C00001164 MYO-INOSITOL 33990 Inositol 5221 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Gateva A, Unfer V, Kamenov Z: The use of inositol(s) isomers in the management of polycystic ovary syndrome: a comprehensive review. Gynecol Endocrinol. 2018 Jul;34(7):545-550. doi: 10.1080/09513590.2017.1421632. Epub 2018 Jan 8. 29309199 1.0 2020-03-18 23:26:27 UTC 2020-07-31 20:34:11 UTC CDB000145 a-D-Galactosamine a-D-Galactosamine, also known as D-chondrosamine or 2-amino-2-deoxy-D-galactose, is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a six-carbon containing moeity. a-D-galactosamine is soluble in water and a very weakly acidic compound (based on its pKa). a-D-galactosamine can be found in a number of food items such as pepper (Capsicum annuum), orange bell pepper, green bell pepper, and yellow bell pepper, which makes a-D-galactosamine a potential biomarker for the consumption of these food products. a-D-galactosamine is a hexosamine derived from galactose with the molecular formula C6H13NO5. This amino sugar is a constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH). Other sugar constituents of FSH and LH include glucosamine, galactose and glucose. a-D-Galactosamine Α-D-galactosamine C6H13NO5 179.17 179.0794 (3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol galactosamine 14196-84-0 N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6+/m1/s1 MSWZFWKMSRAUBD-DVKNGEFBSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds 1,2-aminoalcohols Aminosaccharides Hemiacetals Hydrocarbon derivatives Monoalkylamines Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols 1,2-aminoalcohol Alcohol Aliphatic heteromonocyclic compound Amine Amino saccharide Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organic nitrogen compound Organoheterocyclic compound Organonitrogen compound Oxacycle Oxane Polyol Primary alcohol Primary aliphatic amine Primary amine Secondary alcohol logp -2.73 ALOGPS logs 0.49 ALOGPS logp -3 ChemAxon pka_strongest_acidic 11.73 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac (3R,4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol ChemAxon average_mass 179.17 ChemAxon mono_mass 179.0794 ChemAxon smiles N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O ChemAxon formula C6H13NO5 ChemAxon inchi InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6+/m1/s1 ChemAxon inchikey MSWZFWKMSRAUBD-DVKNGEFBSA-N ChemAxon polar_surface_area 116.17 ChemAxon refractivity 37.58 ChemAxon polarizability 16.52 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5317448 1.0 2020-03-18 23:26:29 UTC 2020-08-04 22:28:10 UTC CDB000146 n-Nonane Nonane, also known as n-Nonane or CH3-[CH2]7-CH3, is a straight-chain alkane with 9 carbon atoms. It belongs to the class of organic compounds known as alkanes. They are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Nonane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water and relatively neutral. It has a gasoline odor ( http://www.thegoodscentscompany.com/data/rw1269671.html#toorgano). Nonane can be found in higher concentrations in limes and common oregano. Nonane has also been detected in celeriac, sweet bay, sweet cherries, gingers, and garden tomato (http://www.thegoodscentscompany.com/data/rw1269671.html#tooccur). Nonane is a volatile oil component and a component of the cuticle of plants. It is also found in Cannabis plants (PMID: 6991645). CH3-[CH2]7-CH3 N-Nonane Nonan Nonane C9H20 128.26 128.1565 nonane nonane 111-84-2 CCCCCCCCC InChI=1S/C9H20/c1-3-5-7-9-8-6-4-2/h3-9H2,1-2H3 BKIMMITUMNQMOS-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons a small molecule alkane water_solubility 0.00022 mg/mL at 25 °C logp 5.65 melting_point -51 °C boiling_point 150.4 - 151.0 °C Wikipedia logp 5.24 ALOGPS logs -5.04 ALOGPS logp 4.46 ChemAxon iupac nonane ChemAxon average_mass 128.26 ChemAxon mono_mass 128.1565 ChemAxon smiles CCCCCCCCC ChemAxon formula C9H20 ChemAxon inchi InChI=1S/C9H20/c1-3-5-7-9-8-6-4-2/h3-9H2,1-2H3 ChemAxon inchikey BKIMMITUMNQMOS-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.21 ChemAxon polarizability 18.5 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7849 C02445 8141 FDB000757 DD9 32892 C00034882 Nonane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:31 UTC 2020-07-10 00:17:45 UTC CDB000147 Decane Decane, also known as n-Decane or CH3-[CH2]8-CH3, is a straight-chain alkane with 10 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. N-decane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. N-Decane is an alkane taste. N-Decane is found in highest concentrations in common oregano and safflowers and also in corns, sweet bay, and sweet cherries ( http://www.thegoodscentscompany.com/data/rw1353501.html#tooccur). Decane is also found in Cannabis plants (PMID: 6991645) and in cannabis smoke (https://doi.org/10.1007/978-1-59259-947-9_2). It is volatilized during the combustion of cannabis. CH3-[CH2]8-CH3 Dekan N-Dekan Decane N-Decane C10H22 142.28 142.1722 decane decane 124-18-5 CCCCCCCCCC InChI=1S/C10H22/c1-3-5-7-9-10-8-6-4-2/h3-10H2,1-2H3 DIOQZVSQGTUSAI-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons alkane an alkane logp 5.802 Wikipedia melting_point −30.5 - −29.2 °C Wikipedia boiling_point 173.8 - 174.4 °C Wikipedia logp 5.87 ALOGPS logs -5.30 ALOGPS logp 4.91 ChemAxon iupac decane ChemAxon average_mass 142.28 ChemAxon mono_mass 142.1722 ChemAxon smiles CCCCCCCCCC ChemAxon formula C10H22 ChemAxon inchi InChI=1S/C10H22/c1-3-5-7-9-10-8-6-4-2/h3-10H2,1-2H3 ChemAxon inchikey DIOQZVSQGTUSAI-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.81 ChemAxon polarizability 20.61 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 14840 15600 FDB005890 D10 41808 CPD-9287 Decane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:34 UTC 2020-08-04 22:28:10 UTC CDB000148 Undecane Undecane, also known as CH3-[CH2]9-CH3 or n-undecane, an 11-carbon molecule, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Undecane has 159 isomers. Undecane is a hydrocarbon lipid molecule. It is very hydrophobic, practically insoluble in water and relatively neutral. Undecane has been detected in lime, cardamoms, oregano and allspice plants, dill leaf, and oil from black walnut, carrot leaf and coriander leaf (http://www.thegoodscentscompany.com/data/rw1040461.html#tooccur). Undodecane is also found in Cannabis plants (PMID: 6991645). Undecane is a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Undecane may also be used as an internal standard in gas chromatography when working with other hydrocarbons. For example, when working with a 50 m crosslinked methyl silicone capillary column with an oven temperature increasing slowly, beginning around 60 ¬∞C, an 11-carbon molecule like undecane may be used as an internal standard to be compared with the retention times of other 10-, 11-, or 12- carbon molecules, depending on their structures. It is used as a mild sex attractant for various types of moths and cockroaches, and an alert signal for a variety of ants ( PMID: 29350346). CH3-[CH2]9-CH3 Hendecane Hendekan N-Undecane Undekan C11H24 156.31 156.1878 undecane undecane 1120-21-4 CCCCCCCCCCC InChI=1S/C11H24/c1-3-5-7-9-11-10-8-6-4-2/h3-11H2,1-2H3 RSJKGSCJYJTIGS-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons alkane an alkane logp 6.312 Wikipedia melting_point −26.6 - −25.0 °C Wikipedia boiling_point 193 to 197 °C Wikipedia logp 5.96 ALOGPS logs -5.65 ALOGPS logp 5.35 ChemAxon iupac undecane ChemAxon average_mass 156.31 ChemAxon mono_mass 156.1878 ChemAxon smiles CCCCCCCCCCC ChemAxon formula C11H24 ChemAxon inchi InChI=1S/C11H24/c1-3-5-7-9-11-10-8-6-4-2/h3-11H2,1-2H3 ChemAxon inchikey RSJKGSCJYJTIGS-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 52.41 ChemAxon polarizability 22.71 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB005363 13619 14257 UND 46342 CPD-9289 Undecane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Monnin T, Helft F, Leroy C, d'Ettorre P, Doums C: Chemical Characterization of Young Virgin Queens and Mated Egg-Laying Queens in the Ant Cataglyphis cursor: Random Forest Classification Analysis for Multivariate Datasets. J Chem Ecol. 2018 Feb;44(2):127-136. doi: 10.1007/s10886-018-0923-7. Epub 2018 Jan 19. 29350346 1.0 2020-03-18 23:26:36 UTC 2020-08-04 22:28:10 UTC CDB000149 n-Dodecane N-dodecane, also known as bihexyl or CH3-[CH2]10-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. N-dodecane is a hydrocarbon lipid molecule that is very hydrophobic molecule, practically insoluble in water, and relatively neutral. N-dodecane is found in higher concentrations in black walnuts and butter and lower amounts in lamb, cocoa, dill, wild strawberry, peas, tea and papaya ( http://www.thegoodscentscompany.com/data/rw1242151.html#tooccur). It was detected in garden tomatoes. Dodecane is also found in Cannabis plants (PMID: 6991645) and in cannabis smoke (https://doi.org/10.1007/978-1-59259-947-9_2). It is volatilized during the combustion of cannabis. Bihexyl CH3-[CH2]10-CH3 Dihexyl Dodekan Adakane 12 Dodecane Duodecane N-Dodecane C12H26 170.33 170.2035 dodecane dodecane 112-40-3 CCCCCCCCCCCC InChI=1S/C12H26/c1-3-5-7-9-11-12-10-8-6-4-2/h3-12H2,1-2H3 SNRUBQQJIBEYMU-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons Hydrocarbons alkane an alkane water_solubility 3.7e-06 mg/mL at 25 °C logp 6.10 melting_point -9.6 °C boiling_point 214 to 218 °C Wikipedia logp 6.42 ALOGPS logs -5.99 ALOGPS logp 5.8 ChemAxon iupac dodecane ChemAxon average_mass 170.33 ChemAxon mono_mass 170.2035 ChemAxon smiles CCCCCCCCCCCC ChemAxon formula C12H26 ChemAxon inchi InChI=1S/C12H26/c1-3-5-7-9-11-12-10-8-6-4-2/h3-12H2,1-2H3 ChemAxon inchikey SNRUBQQJIBEYMU-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 57.01 ChemAxon polarizability 24.83 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004726 7890 8182 D12 28817 C08374 CPD-9290 C00001248 Dodecane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:38 UTC 2020-08-04 22:28:10 UTC CDB000150 Tridecane Tridecane, also known as tridekan, is an alkane hydrocarbon with the chemical formula CH3(CH2)11CH3. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Tridecane has 802 constitutional isomers. Tridecane is a hydrocarbon lipid molecule. Tridecane is a light, combustible colourless liquid and a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a volatile oil component, and has been found in some plants, such as cannabis plants (PMID: 6991645), Abelmoschus esculentus (L.) Moench. and Abelmoschus moschatus Medik (PMID: 23768323), and Bidens pilosa var. radiate (PMID: 24010324). Tridecane is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). It is used in the manufacture of paraffin products, the paper processing industry, in jet fuel research and in the rubber industry; furthermore, tridecane is used as a solvent and distillation chaser. Tridecane is also one of the major chemicals secreted by some insects as a defense against predators. For example, the secretions of the earwig larvae Forficula Auricularia, which contained tridecane, inhibited the feeding of ant species Myrmica rubra (PMID: 24879968). CH3-[CH2]11-CH3 N-Tridecane Tridekan (2S,3S)-2-Hydroxytridecane-1,2,3-tricarboxylate Alkanes, C12-14 Lipid fragment TRD C13H28 184.36 184.2191 tridecane tridecane 629-50-5 CCCCCCCCCCCCC InChI=1S/C13H28/c1-3-5-7-9-11-13-12-10-8-6-4-2/h3-13H2,1-2H3 IIYFAKIEWZDVMP-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons Hydrocarbons an alkane long-chain alkane water_solubility 4.7e-06 mg/mL at 25 °C logp 7.331 Wikipedia melting_point -5.5 °C boiling_point 232 to 236 °C Wikipedia logp 6.85 ALOGPS logs -6.28 ALOGPS logp 6.24 ChemAxon iupac tridecane ChemAxon average_mass 184.36 ChemAxon mono_mass 184.2191 ChemAxon smiles CCCCCCCCCCCCC ChemAxon formula C13H28 ChemAxon inchi InChI=1S/C13H28/c1-3-5-7-9-11-13-12-10-8-6-4-2/h3-13H2,1-2H3 ChemAxon inchikey IIYFAKIEWZDVMP-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 61.62 ChemAxon polarizability 26.96 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012622 11882 12388 35998 TRD C13834 C00048561 Tridecane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Molfetta I, Ceccarini L, Macchia M, Flamini G, Cioni PL: Abelmoschus esculentus (L.) Moench. and Abelmoschus moschatus Medik: seeds production and analysis of the volatile compounds. Food Chem. 2013 Nov 1;141(1):34-40. doi: 10.1016/j.foodchem.2013.02.030. Epub 2013 Mar 1. 23768323 Chen J, Wei JH, Cai SF, Zhang HJ, Zhang XH, Liang WJ, Wu SG: [Chemical constituents in whole herb of Bidens pilosa var. radiata]. Zhong Yao Cai. 2013 Mar;36(3):410-3. 24010324 Gasch T, Vilcinskas A: The chemical defense in larvae of the earwig Forficula auricularia. J Insect Physiol. 2014 Aug;67:1-8. doi: 10.1016/j.jinsphys.2014.05.019. Epub 2014 May 29. 24879968 1.0 2020-03-18 23:26:40 UTC 2020-07-08 16:06:13 UTC CDB000151 Tetradecane Tetradecane, also known as n-tetradecane, belongs to the class of organic compounds known as with the chemical formula CH3-[CH2]12-CH3. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Tetradecane is a hydrocarbon lipid molecule. Tetradecane is very hydrophobic, practically insoluble in water, and relatively neutral. Tetradecane is a mild, alkane, and waxy taste. It is found in highest concentrations within black walnuts. Tetradecane has also been detected in lemon balms, common buckwheats, cucumbers, allspices, and green bell peppers. This could make tetradecane a potential biomarker for the consumption of these foods. Tetradecane is also found in cannabis plants (PMID: 6991645). CH3-[CH2]12-CH3 N-Tetradecane Tetradekan C14H30 198.39 198.2348 tetradecane tetradecane CCCCCCCCCCCCCC InChI=1S/C14H30/c1-3-5-7-9-11-13-14-12-10-8-6-4-2/h3-14H2,1-2H3 BGHCVCJVXZWKCC-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons long-chain alkane melting_point 4 to 6 °C Wikipedia boiling_point 253 to 257 °C Wikipedia logp 7.70 ALOGPS logs -6.55 ALOGPS logp 6.69 ChemAxon iupac tetradecane ChemAxon average_mass 198.39 ChemAxon mono_mass 198.2348 ChemAxon smiles CCCCCCCCCCCCCC ChemAxon formula C14H30 ChemAxon inchi InChI=1S/C14H30/c1-3-5-7-9-11-13-14-12-10-8-6-4-2/h3-14H2,1-2H3 ChemAxon inchikey BGHCVCJVXZWKCC-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 66.22 ChemAxon polarizability 29.08 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004731 11883 12389 41253 C00035879 Tetradecane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:43 UTC 2020-07-10 00:17:47 UTC CDB000152 Pentadecane Pentadecane, also known as CH3-[CH2]13-CH3, is a straight-chain alkane with 15 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Pentadecane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Pentadecane has an alkane and waxy taste. It has been detected in pepper (c. annuum), papaya, pepper (c. frutescens), green bell peppers, and lemons. This could make pentadecane a potential biomarker for the consumption of these foods. Pentadecane has also been found in many different plants and essential oils as a volatile (PMID: 23847066, 23973758), and in cannabis plant as well (PMID: 6991645). Pentadecane is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]13-CH3 N-Pentadecane Pentadekan C15H32 212.41 212.2504 pentadecane pentadecane CCCCCCCCCCCCCCC InChI=1S/C15H32/c1-3-5-7-9-11-13-15-14-12-10-8-6-4-2/h3-15H2,1-2H3 YCOZIPAWZNQLMR-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons Hydrocarbons an alkane long-chain alkane water_solubility 2.866 μg/L Wikipedia logp 7.13 Wikipedia melting_point 16.8 to 10.0 °C Wikipedia boiling_point 270.00 °C Wikipedia logp 8.17 ALOGPS logs -6.77 ALOGPS logp 7.13 ChemAxon iupac pentadecane ChemAxon average_mass 212.41 ChemAxon mono_mass 212.2504 ChemAxon smiles CCCCCCCCCCCCCCC ChemAxon formula C15H32 ChemAxon inchi InChI=1S/C15H32/c1-3-5-7-9-11-13-15-14-12-10-8-6-4-2/h3-15H2,1-2H3 ChemAxon inchikey YCOZIPAWZNQLMR-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 70.82 ChemAxon polarizability 31.21 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11885 12391 FDB011800 C00001265 C08388 CPD-7946 Pentadecane 28897 Radulovic NS, Mladenovic MZ, Blagojevic PD: A 'low-level' chemotaxonomic analysis of the plant family Apiaceae: the case of Scandix balansae Reut. ex Boiss. (tribe Scandiceae). Chem Biodivers. 2013 Jul;10(7):1202-19. doi: 10.1002/cbdv.201300106. 23847066 Li C, Xu F, Cao C, Shang MY, Zhang CY, Yu J, Liu GX, Wang X, Cai SQ: Comparative analysis of two species of Asari Radix et Rhizoma by electronic nose, headspace GC-MS and chemometrics. J Pharm Biomed Anal. 2013 Nov;85:231-8. doi: 10.1016/j.jpba.2013.07.034. Epub 2013 Aug 7. 23973758 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:45 UTC 2020-07-07 15:55:46 UTC CDB000153 Hexadecane Hexadecane, also known as cetan or CH3-[CH2]14-CH3, is a straight-chain alkane with 16 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Hexadecane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Hexadecane is an alkane taste. It is found in highest concentrations in black walnuts. Hexadecane has also been detected in allspices, cucumbers, tea, orange bell peppers, and herbs and spices. This could make hexadecane a potential biomarker for the consumption of these foods. Hexadecane has been associated with certain gastrointestinal diseases, such as ulcerative colitis, resulting from Clostridium difficile and Campylobacter jejuni infections (PMID: 17314143). Hexadecane has a role as a plant metabolite as a volatile oil component. Hexadecane is also found in cannabis plants (PMID: 6991645) Cetan Cetane CH3-[CH2]14-CH3 Hexadekan N-Cetane N-Hexadecane Zetan 1,2-Epoxyhexadecane CNS C16H34 226.44 226.2661 hexadecane cetane 544-76-3 CCCCCCCCCCCCCCCC InChI=1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 DCAYPVUWAIABOU-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane water_solubility 9e-07 mg/mL at 25 °C logp 8.859 Wikipedia melting_point 18.17 °C boiling_point 287 °C Wikipedia logp 8.63 ALOGPS logs -6.99 ALOGPS logp 7.58 ChemAxon iupac hexadecane ChemAxon average_mass 226.44 ChemAxon mono_mass 226.2661 ChemAxon smiles CCCCCCCCCCCCCCCC ChemAxon formula C16H34 ChemAxon inchi InChI=1S/C16H34/c1-3-5-7-9-11-13-15-16-14-12-10-8-6-4-2/h3-16H2,1-2H3 ChemAxon inchikey DCAYPVUWAIABOU-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 75.42 ChemAxon polarizability 33.34 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB011952 10540 11006 R16 C14499 45296 C00035639 Hexadecane Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. doi: 10.1096/fj.06-6927com. Epub 2007 Feb 21. 17314143 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:47 UTC 2020-07-07 15:55:46 UTC CDB000154 Heptadecane Heptadecane, also known as CH3-[CH2]15-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Heptadecane is a hydrocarbon lipid molecule that is volatile, very hydrophobic, practically insoluble in water, and relatively neutral. In the IUPAC nomenclature, the name of this compound is simply heptadecane, since the other isomers are viewed and named as alkyl-substituted versions of smaller alkanes. The unbranched isomer is normal or n-heptadecane. Indeed, it is believed to be the smallest "impossible" alkane. Heptadecane has been detected in lemon balms, coconuts, orange bell peppers, allspices, and pepper (c. annuum). This could make heptadecane a potential biomarker for the consumption of these foods. Heptadecane is also found in cannabis plants (PMID: 6991645). Heptadecane blocks the de novo synthesis of fatty acids and has an anti-inflammatory effect in aged kidneys (PMID: 23555655). CH3-[CH2]15-CH3 Heptadekan N-Heptadecane C17H36 240.47 240.2817 heptadecane heptadecane CCCCCCCCCCCCCCCCC InChI=1S/C17H36/c1-3-5-7-9-11-13-15-17-16-14-12-10-8-6-4-2/h3-17H2,1-2H3 NDJKXXJCMXVBJW-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons Hydrocarbons a small molecule long-chain alkane melting_point 21.1 to 22.9 °C Wikipedia boiling_point 301.9 °C Wikipedia logp 9.01 ALOGPS logs -7.23 ALOGPS logp 8.02 ChemAxon iupac heptadecane ChemAxon average_mass 240.47 ChemAxon mono_mass 240.2817 ChemAxon smiles CCCCCCCCCCCCCCCCC ChemAxon formula C17H36 ChemAxon inchi InChI=1S/C17H36/c1-3-5-7-9-11-13-15-17-16-14-12-10-8-6-4-2/h3-17H2,1-2H3 ChemAxon inchikey NDJKXXJCMXVBJW-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 80.02 ChemAxon polarizability 35.48 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01816 FDB004729 11892 C00030472 HEPTADECANE-CPD Heptadecane 12398 16148 Kim DH, Park MH, Choi YJ, Chung KW, Park CH, Jang EJ, An HJ, Yu BP, Chung HY: Molecular study of dietary heptadecane for the anti-inflammatory modulation of NF-kB in the aged kidney. PLoS One. 2013;8(3):e59316. doi: 10.1371/journal.pone.0059316. Epub 2013 Mar 26. 23555655 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:49 UTC 2020-08-04 22:28:11 UTC CDB000155 Octadecane Octadecane, also known as CH3-[CH2]16-CH3 or oktadekan, is a straight-chain alkane carrying 18 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons and therefore consist entirely of hydrogen atoms and saturated carbon atoms. Thus, octadecane is a hydrocarbon lipid molecule. Octadecane is an odorless white crystal or powder that is very hydrophobic, practically insoluble in water, and relatively neutral. Octadecane is an alkane taste. It has been detected in papaya, corianders, sunflowers, kohlrabis, and parsnips. This could make octadecane a potential biomarker for the consumption of these foods. Octadecane is also found in cannabis plants (PMID: 6991645). Octadecane, in addition to other flavonoids, alyloids and sugars, extracted from the root of Trichosanthes dioica, exhibited antimicrobial activity against Proteus mirabilis¬†and Bacillus subtilis http://www.phytojournal.com/archives/?year=2016&vol=5&issue=5&part=F&ArticleId=985) CH3-[CH2]16-CH3 N-Octadecane Oktadekan Octadecane, 1-(14)C-labeled CPD Octadecane, 14C-labeled CPD C18H38 254.49 254.2974 octadecane octadecane 593-45-3 CCCCCCCCCCCCCCCCCC InChI=1S/C18H38/c1-3-5-7-9-11-13-15-17-18-16-14-12-10-8-6-4-2/h3-18H2,1-2H3 RZJRJXONCZWCBN-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons long-chain alkane water_solubility 6e-06 mg/mL at 25 °C melting_point 28 °C boiling_point 317 °C Wikipedia logp 9.31 ALOGPS logs -7.38 ALOGPS logp 8.47 ChemAxon iupac octadecane ChemAxon average_mass 254.49 ChemAxon mono_mass 254.2974 ChemAxon smiles CCCCCCCCCCCCCCCCCC ChemAxon formula C18H38 ChemAxon inchi InChI=1S/C18H38/c1-3-5-7-9-11-13-15-17-18-16-14-12-10-8-6-4-2/h3-18H2,1-2H3 ChemAxon inchikey RZJRJXONCZWCBN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 84.62 ChemAxon polarizability 37.62 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11145 FDB011840 11635 32926 8K6 CPD-16902 C00030879 Octadecane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:52 UTC 2020-08-04 22:28:11 UTC CDB000156 Nonadecane Nonadecane, also known as CH3-[CH2]17-CH3 or nonadekan, is a straight-chain alkane with 19 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons that consist entirely of hydrogen atoms and saturated carbon atoms. Nonadecane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. It has an alkane and bland taste, and has been detected in pomes, watermelons, yellow bell peppers, allspices, and papaya. This could make nonadecane a potential biomarker for the consumption of these foods. Nonadecane is as a component of essential oils isolated from Artemisia armeniaca and rose essential oil from Rosa damascene (PMID: 24459472). Nonadecane is also found in cannabis plants (PMID: 6991645). CH3-[CH2]17-CH3 N-Nonadecane Nonadekan N-NONADECANE, 99% Unknown branched fragment OF phospholipid Unknown phospholipid fragment Perdeuterated nonadecance C19H40 268.52 268.313 nonadecane nonadecane 629-92-5 CCCCCCCCCCCCCCCCCCC InChI=1S/C19H40/c1-3-5-7-9-11-13-15-17-19-18-16-14-12-10-8-6-4-2/h3-19H2,1-2H3 LQERIDTXQFOHKA-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane melting_point 32 °C boiling_point 330 °C Wikipedia logp 9.55 ALOGPS logs -7.51 ALOGPS logp 8.91 ChemAxon iupac nonadecane ChemAxon average_mass 268.52 ChemAxon mono_mass 268.313 ChemAxon smiles CCCCCCCCCCCCCCCCCCC ChemAxon formula C19H40 ChemAxon inchi InChI=1S/C19H40/c1-3-5-7-9-11-13-15-17-19-18-16-14-12-10-8-6-4-2/h3-19H2,1-2H3 ChemAxon inchikey LQERIDTXQFOHKA-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 89.22 ChemAxon polarizability 39.76 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012627 11895 12401 C00030827 Nonadecane 32927 Sadraei H, Asghari G, Emami S: Inhibitory effect of Rosa damascena Mill flower essential oil, geraniol and citronellol on rat ileum contraction. Res Pharm Sci. 2013 Jan;8(1):17-23. 24459472 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:54 UTC 2020-07-24 23:30:06 UTC CDB000157 Eicosane Eicosane, also called icosane, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CH3-[CH2]18-CH3, and consist entirely of hydrogen atoms and saturated carbon atoms. Eeicosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Eicosane has an alkane, and a colorless and waxy taste. It is found in highest concentrations in lemon balms. Eicosane has also been detected in allspices, papaya, coconuts, lindens, and hyssops. This could make eicosane a potential biomarker for the consumption of these foods. Eicosane is also found in cannabis plants (PMID: 6991645). Eicosane was associated with Parkinson's disease (PMID: 31041379). CH3-[CH2]18-CH3 N-Eicosane Octyldodecane Icosane Eicosane C20H42 282.55 282.3287 icosane eicosane 112-95-8 CCCCCCCCCCCCCCCCCCCC InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3 CBFCDTFDPHXCNY-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons long-chain alkane logp 10.897 Wikipedia melting_point 36 to 38 °C Wikipedia boiling_point 343.1 °C Wikipedia logp 9.78 ALOGPS logs -7.61 ALOGPS logp 9.36 ChemAxon iupac icosane ChemAxon average_mass 282.55 ChemAxon mono_mass 282.3287 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC ChemAxon formula C20H42 ChemAxon inchi InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3 ChemAxon inchikey CBFCDTFDPHXCNY-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 93.82 ChemAxon polarizability 41.94 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004727 7929 8222 43619 LFA CPD-14231 Icosane Trivedi DK, Sinclair E, Xu Y, Sarkar D, Walton-Doyle C, Liscio C, Banks P, Milne J, Silverdale M, Kunath T, Goodacre R, Barran P: Discovery of Volatile Biomarkers of Parkinson's Disease from Sebum. ACS Cent Sci. 2019 Apr 24;5(4):599-606. doi: 10.1021/acscentsci.8b00879. Epub 2019 Mar 20. 31041379 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:26:56 UTC 2020-07-07 15:55:49 UTC CDB000158 Heneicosane Heneicosane, is a straight chain saturated hydrocarbon with 21 carbons that is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, heneicosane is considered to be a hydrocarbon lipid molecule. Henicosane is a neutral, hydrophobic molecule that is insoluble in water. It exists as a clear, waxy solid. Heneicosane is a naturally occurring, waxy tasting compound that can be found in a number of food items such as orange bell pepper, yellow bell pepper, lemon balm, and pepper (c. annuum). Henicosane is one of many alkanes that are known in cannabis plants (PMID: 6991645). Heneicosane is used as a pheromone by queen or king termites. It also attracts mosquitoes in the genus Aedes and can be used in mosquito baits (PMID: 24060842). CH3-[CH2]19-CH3 N-Heneicosane Heneicosane C21H44 296.57 296.3443 henicosane heneicosane 629-94-7 CCCCCCCCCCCCCCCCCCCCC InChI=1S/C21H44/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3 FNAZRRHPUDJQCJ-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane water_solubility 2.9e−11 g/L Wikipedia logp 10.65 Wikipedia melting_point 40.5 °C Wikipedia boiling_point 356.10 °C Wikipedia logp 9.98 ALOGPS logs -7.69 ALOGPS logp 9.8 ChemAxon iupac henicosane ChemAxon average_mass 296.57 ChemAxon mono_mass 296.3443 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCC ChemAxon formula C21H44 ChemAxon inchi InChI=1S/C21H44/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3 ChemAxon inchikey FNAZRRHPUDJQCJ-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 98.42 ChemAxon polarizability 44.09 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11897 12403 32931 FDB004728 CPD-7935 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kumar P, Lomash V, Jatav PC, Kumar A, Pant SC: Prenatal developmental toxicity study of n-heneicosane in Wistar rats. Toxicol Ind Health. 2016 Jan;32(1):118-25. doi: 10.1177/0748233713498438. Epub 2013 Sep 23. 24060842 1.0 2020-03-18 23:26:58 UTC 2020-07-10 00:17:45 UTC CDB000159 Docosane Docosane, also called n-docosane, is a straight-chain alkane with 22 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons, they have the general formula CH3-[CH2]20-CH3, and consist entirely of hydrogen atoms and saturated carbon atoms. Docosane is a hydrocarbon lipid molecule that is a hydrophobic, practically insoluble in water, and relatively neutral. Docosane is waxy taste. It is found in highest concentrations in lemon balms detected in allspices, lindens, papaya, and sunflowers. This could make docosane a potential biomarker for the consumption of these foods. Docosane has been found in the essential oils from plants, such as dill (PMID: 25154406) and Periploca laevigata Aiton subsp. angustifolia (Apocynaceae) (PMID: 22439883). Docosane is also found in cannabis plants (PMID: 6991645) and in cannabis smoke (https://doi.org/10.1007/978-1-59259-947-9_2). It is volatilized during the combustion of cannabis. CH3-[CH2]20-CH3 Dokosan N-Docosane C22H46 310.6 310.36 docosane docosane 629-97-0 CCCCCCCCCCCCCCCCCCCCCC InChI=1S/C22H46/c1-3-5-7-9-11-13-15-17-19-21-22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H3 HOWGUJZVBDQJKV-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons long-chain alkane logp 10.16 ALOGPS logs -7.76 ALOGPS logp 10.24 ChemAxon iupac docosane ChemAxon average_mass 310.6 ChemAxon mono_mass 310.36 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C22H46 ChemAxon inchi InChI=1S/C22H46/c1-3-5-7-9-11-13-15-17-19-21-22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H3 ChemAxon inchikey HOWGUJZVBDQJKV-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 103.02 ChemAxon polarizability 46.26 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004725 11899 TWT 46050 12405 C00035592 Higher alkanes Kazemi M: Phenolic profile, antioxidant capacity and anti-inflammatory activity of Anethum graveolens L. essential oil. Nat Prod Res. 2015;29(6):551-3. doi: 10.1080/14786419.2014.951934. Epub 2014 Aug 26. 25154406 Zito P, Sajeva M, Bruno M, Rosselli S, Maggio A, Senatore F: Essential oils composition of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae-Periplocoideae). Nat Prod Res. 2013;27(3):255-65. doi: 10.1080/14786419.2012.671319. Epub 2012 Mar 23. 22439883 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:00 UTC 2020-07-10 00:17:45 UTC CDB000160 Tricosane Tricosane, also called n-tricosane, is a straight chain alkane containing 23 carbon atoms. It belongs to the class of organic compounds known as acyclic alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2. It is a white waxy solid with an alkane taste. It has been detected in common hazelnuts, making tricosane a potential biomarker for this food. As a volatile compound, it has also been found in essential oils of plants, such as Periploca laevigata Aiton subsp. angustifolia (Apocynaceae) (PMID: 22439883) and Aerva javanica (Burm.f.) Juss. ex Schult. seed (PMID: 23811454). Tricosane is also found in cannabis plants (PMID: 6991645) and in cannabis smoke (https://doi.org/10.1007/978-1-59259-947-9_2). Tricosane is volatilized during the combustion of cannabis. CH3-[CH2]21-CH3 N-Tricosane C23H48 324.63 324.3756 tricosane tricosane 638-67-5 CCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C23H48/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h3-23H2,1-2H3 FIGVVZUWCLSUEI-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 10.30 ALOGPS logs -7.82 ALOGPS logp 10.69 ChemAxon iupac tricosane ChemAxon average_mass 324.63 ChemAxon mono_mass 324.3756 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C23H48 ChemAxon inchi InChI=1S/C23H48/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h3-23H2,1-2H3 ChemAxon inchikey FIGVVZUWCLSUEI-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 107.63 ChemAxon polarizability 48.38 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB005217 12017 32934 12534 C00032409 C17433 CPD-7947 Higher alkanes Zito P, Sajeva M, Bruno M, Rosselli S, Maggio A, Senatore F: Essential oils composition of Periploca laevigata Aiton subsp. angustifolia (Labill.) Markgraf (Apocynaceae-Periplocoideae). Nat Prod Res. 2013;27(3):255-65. doi: 10.1080/14786419.2012.671319. Epub 2012 Mar 23. 22439883 Samejo MQ, Memon S, Bhanger MI, Khan KM: Comparison of chemical composition of Aerva javanica seed essential oils obtained by different extraction methods. Pak J Pharm Sci. 2013 Jul;26(4):757-60. 23811454 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:03 UTC 2020-07-10 00:17:47 UTC CDB000161 Tetracosane Tetracosane, also called lignocerane or n-tetracosane, is a straight-chain alkane containing 24 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons with, they have the general formula CH3-[CH2]22-CH3, and consist entirely of hydrogen atoms and saturated carbon atoms. Tetracosane is a hydrocarbon lipid molecule. Tetracosane is a colourless and waxy crystal, that is very hydrophobic, practically insoluble in water, and relatively neutral. Tetracosane has been found in lindens, citrus, sunflowers, allspices, and papaya. This could make tetracosane a potential biomarker for the consumption of these foods. As a volatile oil component, tetracosane has been found in the essential oils from plants, such as dill (PMID: 25154406) and cannabis plants (PMID: 6991645). Tetracosane is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]22-CH3 N-Tetracosane C24H50 338.65 338.3913 tetracosane tetracosane 646-31-1 CCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C24H50/c1-3-5-7-9-11-13-15-17-19-21-23-24-22-20-18-16-14-12-10-8-6-4-2/h3-24H2,1-2H3 POOSGDOYLQNASK-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane melting_point 54 °C boiling_point 391.4 °C Wikipedia logp 10.43 ALOGPS logs -7.87 ALOGPS logp 11.13 ChemAxon iupac tetracosane ChemAxon average_mass 338.65 ChemAxon mono_mass 338.3913 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C24H50 ChemAxon inchi InChI=1S/C24H50/c1-3-5-7-9-11-13-15-17-19-21-23-24-22-20-18-16-14-12-10-8-6-4-2/h3-24H2,1-2H3 ChemAxon inchikey POOSGDOYLQNASK-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 112.23 ChemAxon polarizability 50.52 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012620 12072 12592 32936 C00032307 Tetracosane Kazemi M: Phenolic profile, antioxidant capacity and anti-inflammatory activity of Anethum graveolens L. essential oil. Nat Prod Res. 2015;29(6):551-3. doi: 10.1080/14786419.2014.951934. Epub 2014 Aug 26. 25154406 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:05 UTC 2020-07-24 23:30:06 UTC CDB000162 Pentacosane n-Pentacosane, also known as CH3-[CH2]23-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. n-pentacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. n-Pentacosane has been detected in coconuts, avocado, ginkgo nuts, cardamoms, and lindens. This could make n-pentacosane a potential biomarker for the consumption of these foods. Pentacosane is also present in the essential oil of cannbis obtained by extraction and steam distillation (PMID: 6991645). n-Pentacosane is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]23-CH3 N-Pentacosane C25H52 352.68 352.4069 pentacosane pentacosane 629-99-2 CCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C25H52/c1-3-5-7-9-11-13-15-17-19-21-23-25-24-22-20-18-16-14-12-10-8-6-4-2/h3-25H2,1-2H3 YKNWIILGEFFOPE-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 10.55 ALOGPS logs -7.90 ALOGPS logp 11.58 ChemAxon iupac pentacosane ChemAxon average_mass 352.68 ChemAxon mono_mass 352.4069 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C25H52 ChemAxon inchi InChI=1S/C25H52/c1-3-5-7-9-11-13-15-17-19-21-23-25-24-22-20-18-16-14-12-10-8-6-4-2/h3-25H2,1-2H3 ChemAxon inchikey YKNWIILGEFFOPE-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 116.83 ChemAxon polarizability 52.67 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004730 12406 32938 CPD-7944 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:07 UTC 2020-08-04 22:28:11 UTC CDB000163 Hexacosane Hexacosane, also known as CH3-[CH2]24-CH3, is straight-chain alkane comprised of 26 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms andsaturated carbon atoms. Hexacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Hexacosane has been detected in peachs, sunflowers, parsnips, coconuts, and papaya. This could make hexacosane a potential biomarker for the consumption of these foods. Hexacosane is an abundant alkane found in cannabis plants (PMID: 6991645). Hexacosane, isolated from Sansevieria liberica, exhibited antimicrobial activity against Klebsiela pnemoniae, Salmonela typhi, Mithecithinne staphaureus and Proteus vulgaris (¬†http://oaji.net/articles/2016/2853-1456142774.pdf).¬†Hexacosane is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]24-CH3 N-Hexacosane C26H54 366.71 366.4226 hexacosane hexacosane 630-01-3 CCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C26H54/c1-3-5-7-9-11-13-15-17-19-21-23-25-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-26H2,1-2H3 HMSWAIKSFDFLKN-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 10.66 ALOGPS logs -7.95 ALOGPS logp 12.02 ChemAxon iupac hexacosane ChemAxon average_mass 366.71 ChemAxon mono_mass 366.4226 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C26H54 ChemAxon inchi InChI=1S/C26H54/c1-3-5-7-9-11-13-15-17-19-21-23-25-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-26H2,1-2H3 ChemAxon inchikey HMSWAIKSFDFLKN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 121.43 ChemAxon polarizability 54.84 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001818 11901 32940 12407 C00030478 CPD-9763 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:10 UTC 2020-08-04 22:28:11 UTC CDB000164 2-Methylhexacosane 2-Methylhexacosane, also known as isoheptacosane, belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. 2-Methylhexacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. 2-methylhexacosane has been detected in alcoholic beverages and citrus. This could make 2-methylhexacosane a potential biomarker for the consumption of these foods. 2-Methylhexacosane is an abundant alkane found in cannabis plants (PMID: 6991645). 2-Methylhexacosane, in addition to other flavonoids, alkaloids and reducing sugars, extracted from the root of Trichosanthes dioica, exhibited antimicrobial activity against Proteus mirabilis¬†and Bacillus subtilis http://www.phytojournal.com/archives/?year=2016&vol=5&issue=5&part=F&ArticleId=985). 2-Methyl-hexacosane Isoheptacosane C27H56 380.73 380.4382 2-methylhexacosane 2-methylhexacosane 1561-02-0 CCCCCCCCCCCCCCCCCCCCCCCCC(C)C InChI=1S/C27H56/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27(2)3/h27H,4-26H2,1-3H3 BEBPORIYFVRVCP-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane Hydrocarbons melting_point 49 - 50.5 °C logp 10.73 ALOGPS logs -7.99 ALOGPS logp 12.31 ChemAxon iupac 2-methylhexacosane ChemAxon average_mass 380.73 ChemAxon mono_mass 380.4382 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCC(C)C ChemAxon formula C27H56 ChemAxon inchi InChI=1S/C27H56/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27(2)3/h27H,4-26H2,1-3H3 ChemAxon inchikey BEBPORIYFVRVCP-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 125.98 ChemAxon polarizability 56.68 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB010612 133028 150931 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:12 UTC 2020-08-04 22:28:11 UTC CDB000165 Heptacosane Heptacosane, also known as CH3-[CH2]25-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Thus, heptacosane is a hydrocarbon lipid molecule, is very hydrophobic, practically insoluble in water, and relatively neutral. Heptacosane has been detected in avocado, sunflowers, peachs, sweet cherries, and wild carrots. This could make heptacosane a potential biomarker for the consumption of these foods. Heptacosane as a volatile oil component found in the essential oils from plants such as cannabis (PMID: 6991645) and L. orientalis (PMID: 24708513). It is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Heptacosane, in addition to other flavonoids, alkaloids and sugars, extracted from the root of Trichosanthes dioica, exhibited antimicrobial activity against Proteus mirabilis¬†and Bacillus subtilis http://www.phytojournal.com/archives/?year=2016&vol=5&issue=5&part=F&ArticleId=985 CH3-[CH2]25-CH3 N-Heptacosane C27H56 380.73 380.4382 heptacosane heptacosane 593-49-7 CCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C27H56/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-27H2,1-2H3 BJQWYEJQWHSSCJ-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 10.74 ALOGPS logs -7.97 ALOGPS logp 12.47 ChemAxon iupac heptacosane ChemAxon average_mass 380.73 ChemAxon mono_mass 380.4382 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C27H56 ChemAxon inchi InChI=1S/C27H56/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-27H2,1-2H3 ChemAxon inchikey BJQWYEJQWHSSCJ-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 126.03 ChemAxon polarizability 56.96 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001817 11636 32941 C00030471 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Ertas A, Goren AC, Boga M, Yesil Y, Kolak U: Essential oil compositions and anticholinesterase activities of two edible plants Tragopogon latifolius var. angustifolius and Lycopsis orientalis. Nat Prod Res. 2014;28(17):1405-8. doi: 10.1080/14786419.2014.905558. Epub 2014 Apr 7. 24708513 1.0 2020-03-18 23:27:14 UTC 2020-08-04 22:28:11 UTC CDB000166 Octacosane Octacosane, also known as CH3-[CH2]26-CH3, is a straight-chain alkane containing 28 carbon atoms. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Thus, octacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Octacosane has been detected in peachs, coconuts, apples, sweet cherries, and lindens. This could make octacosane a potential biomarker for the consumption of these foods. Octacosane is an alkane found in cannabis plant (PMID: 6991645). Octacosane, extracted from the crude leaf of Moschosma polystachyum Linn (lamiaceae), exhibited mosquitocidal activitiy (PMID: 14698514). Octacosane, in addition to other flavonoids, alkaloids and sugars, extracted from the root of Trichosanthes dioica, exhibited antimicrobial activity against Proteus mirabilis¬†and Bacillus subtilis (http://www.phytojournal.com/archives/?year=2016&vol=5&issue=5&part=F&ArticleId=985). Octacosane is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]26-CH3 N-Octacosane C28H58 394.76 394.4539 octacosane octacosane 630-02-4 CCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C28H58/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-28H2,1-2H3 ZYURHZPYMFLWSH-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 10.83 ALOGPS logs -7.98 ALOGPS logp 12.91 ChemAxon iupac octacosane ChemAxon average_mass 394.76 ChemAxon mono_mass 394.4539 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C28H58 ChemAxon inchi InChI=1S/C28H58/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-28H2,1-2H3 ChemAxon inchikey ZYURHZPYMFLWSH-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 130.63 ChemAxon polarizability 59.11 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001869 11902 32943 12408 C00034614 CPD-9765 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rajkumar S, Jebanesan A: Mosquitocidal activities of octacosane from Moschosma polystachyum Linn (lamiaceae). J Ethnopharmacol. 2004 Jan;90(1):87-9. doi: 10.1016/j.jep.2003.09.030. 14698514 1.0 2020-03-18 23:27:16 UTC 2020-07-07 15:55:55 UTC CDB000167 2-Methyloctacosane 2-Methyloctacosane, also known as isononacosane, belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 2-methyloctacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. 2-Methyloctacosane has been detected in alcoholic beverages, cereals and cereal products, and citrus. This could make 2-methyloctacosane a potential biomarker for the consumption of these foods. 2-Methyloctacosane is one of several hydrocarbons found in cannabis plants (PMID: 6991645). In addition to plant, 2-Methyloctacosane is one of an epicuticular hydrocarbons found in Drosophila mojavensis cluster species (PMID: 11710615). 2-Methyl-octacosane Isononacosane C29H60 408.79 408.4695 2-methyloctacosane 2-methyloctacosane 1560-98-1 CCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C InChI=1S/C29H60/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29(2)3/h29H,4-28H2,1-3H3 YGCGPCUUTAKOEU-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane Hydrocarbons logp 10.89 ALOGPS logs -8.03 ALOGPS logp 13.2 ChemAxon iupac 2-methyloctacosane ChemAxon average_mass 408.79 ChemAxon mono_mass 408.4695 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C ChemAxon formula C29H60 ChemAxon inchi InChI=1S/C29H60/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29(2)3/h29H,4-28H2,1-3H3 ChemAxon inchikey YGCGPCUUTAKOEU-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 135.18 ChemAxon polarizability 61 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000891 452835 519147 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Etges WJ, Jackson LL: Epicuticular hydrocarbon variation in Drosophila mojavensis cluster species. J Chem Ecol. 2001 Oct;27(10):2125-49. doi: 10.1023/a:1012203222876. 11710615 1.0 2020-03-18 23:27:18 UTC 2020-07-10 00:17:47 UTC CDB000168 Nonacosane Nonacosane, also known as CH3-[CH2]27-CH3, with a molecular formula of C29H60, is a straight-chain hydrocarbon with 1,590,507,121 constitutional isomers. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Nonacosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. It can also be prepared synthetically. Nonacosane has been detected in peaches, ginkgo nuts, cauliflowers, arabica coffee, and lambs quarters. This could make nonacosane a potential biomarker for the consumption of these foods. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma. Evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito). Nonacosane has been identified within several essential oils from plants such as cannabis plants (PMID: 6991645). Nonacosane is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]27-CH3 N-Nonacosane C29H60 408.79 408.4695 nonacosane nonacosane 630-03-5 CCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C29H60/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-29H2,1-2H3 IGGUPRCHHJZPBS-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons Hydrocarbons an alkane long-chain alkane logp 15.482 Wikipedia melting_point 64 °C boiling_point 440.9 °C Wikipedia logp 10.90 ALOGPS logs -7.97 ALOGPS logp 13.36 ChemAxon iupac nonacosane ChemAxon average_mass 408.79 ChemAxon mono_mass 408.4695 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C29H60 ChemAxon inchi InChI=1S/C29H60/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-29H2,1-2H3 ChemAxon inchikey IGGUPRCHHJZPBS-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 135.23 ChemAxon polarizability 61.27 ChemAxon rotatable_bond_count 26 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006240 11903 12409 C00001260 C08384 CPD-7940 Nonacosane 7613 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:21 UTC 2020-07-31 20:34:16 UTC CDB000169 n-Triacontane n-Triacontane, also known as CH3-[CH2]28-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Thus, n-triacontane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. N-Triacontane has been detected in roman camomiles, black elderberries, coconuts, corianders, and german camomiles. This could make n-Triacontane a potential biomarker for the consumption of these foods. n-Triacontane is one of many hydrocarbons found in cannabis plants (PMID:6991645) and also found in two medical plants: Leptadenia reticulata and Pluchea lanceolata (https://doi.org/10.1155/2014/143948). n-Triacontane is a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). CH3-[CH2]28-CH3 N-Triacontane C30H62 422.81 422.4852 triacontane triacontane 638-68-6 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C30H62/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-30H2,1-2H3 JXTPJDDICSTXJX-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 10.95 ALOGPS logs -8.00 ALOGPS logp 13.8 ChemAxon iupac triacontane ChemAxon average_mass 422.81 ChemAxon mono_mass 422.4852 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C30H62 ChemAxon inchi InChI=1S/C30H62/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-30H2,1-2H3 ChemAxon inchikey JXTPJDDICSTXJX-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 139.83 ChemAxon polarizability 63.43 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004732 12535 31006 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:23 UTC 2020-08-04 22:28:11 UTC CDB000170 Dotriacontane Dotriacontane, also known as bicetyl or CH3-[CH2]30-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Thus, dotriacontane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Dotriacontane has been detected in coconuts, garden tomato (var.), papaya, and tea. This could make dotriacontane a potential biomarker for the consumption of these foods. Dotriacontane is also one of many hydrocarbons found in cannabis plants (PMID: 6991645). Alkanes have two main commercial sources: petroleum (crude oil) and natural gas. Alkanes from nonane to hexadecane (an alkane with sixteen carbon atoms) are liquids of higher viscosity, which are less suitable for use in gasoline. From this group on, the n-alkanes are generally solid (waxws) at standard conditions. Alkanes from hexadecane upwards form the most important components of fuel oil and lubricating oil. Alkanes with a chain length of approximately 35 or more carbon atoms are found in bitumen (asphalt), and are used in road surfacing. Mixtures of the normal alkanes are used as boiling point standards for simulated distillation by gas chromatography, a separation process used to improve the economics of oil and gas production. ¬† Bicetyl CH3-[CH2]30-CH3 N-Dotriacontane Dicetyl Lacceran C32H66 450.87 450.5165 dotriacontane dotriacontane 544-85-4 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C32H66/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-32H2,1-2H3 QHMGJGNTMQDRQA-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons long-chain alkane melting_point 74 - 75 °C logp 11.07 ALOGPS logs -8.01 ALOGPS logp 14.69 ChemAxon iupac dotriacontane ChemAxon average_mass 450.87 ChemAxon mono_mass 450.5165 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C32H66 ChemAxon inchi InChI=1S/C32H66/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-32H2,1-2H3 ChemAxon inchikey QHMGJGNTMQDRQA-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 149.03 ChemAxon polarizability 67.71 ChemAxon rotatable_bond_count 29 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012240 11008 10542 36020 C00034834 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:25 UTC 2020-07-24 23:30:06 UTC CDB000171 Tritriacontane Tritriacontane, also known as CH3-[CH2]31-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Thus, tritriacontane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Tritriacontane has been detected in cardamoms, garden tomato (var.), and papaya. This could make tritriacontane a potential biomarker for the consumption of these foods. Tritriacontane is one of several hydrocarbons found in cannabis plants (PMID: 6991645) and Medicago arabica (PMID: 17793563). CH3-[CH2]31-CH3 N-Tritriacontane C33H68 464.89 464.5321 tritriacontane tritriacontane 630-05-7 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C33H68/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-33H2,1-2H3 SUJUOAZFECLBOA-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane logp 11.10 ALOGPS logs -8.01 ALOGPS logp 15.13 ChemAxon iupac tritriacontane ChemAxon average_mass 464.89 ChemAxon mono_mass 464.5321 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C33H68 ChemAxon inchi InChI=1S/C33H68/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-33H2,1-2H3 ChemAxon inchikey SUJUOAZFECLBOA-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 153.64 ChemAxon polarizability 69.89 ChemAxon rotatable_bond_count 30 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C08393 12411 FDB001484 9751 C00001270 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Oro J, Nooner DW, Wikstrom SA: Paraffinic Hydrocarbons in Pasture Plants. Science. 1965 Feb 19;147(3660):870-3. doi: 10.1126/science.147.3660.870. 17793563 1.0 2020-03-18 23:27:27 UTC 2020-08-04 22:28:11 UTC CDB000172 Caprylaldehyde Caprylaldehyde also known as Octanal, or aldehyde C8, belongs to the class of organic compounds known as medium-chain aldehydes, which are aldehydes with a chain length between 6 and 12 carbon atoms. Octanal is a fatty aldehyde lipid molecule. It is produced by¬†hydroformylation¬†of¬†heptene¬†and the¬†dehydrogenation¬†of¬†1-octanol ( ¬†doi:10.1002/14356007.a01_321.pub2 ). Caprylaldehyde is very hydrophobic, practically insoluble in water, and relatively neutral. Octanal is colorless or lightly yellow tinged fragrant liquid with a fruit-like (green, orange, rose, coconut) odor and a waxy, citrus or fruity taste. It occurs naturally in citrus (such as blood orange, lime, mandarin, orange) and other oils from bergamot, blood orange, lime, lemon, grapefruit, orange peel and yuzu peel. Caprylaldehyde is one of the simple aldehydes found in cannabis plants (PMID:6991645) as well as carrot root, celery shoot and leaf, ceylon cinnamon leaf, rose and witch hazel leaf ( http://www.thegoodscentscompany.com/data/rw1000251.html#tooccur). It is used commercially as a component in perfumes and in flavor production for the food industry. It is also used as a raw material for surfactants, for conditioners, for disinfectants and for plasticizers. It is used as an oil base for lubricants of synthetic resin and for emulsifiers of emulsion polymerization. Octanal is also used as a material for creams and ointments. Additionally, octanal is used as a masking agent, a perfuming agent and a viscosity controlling agent in the food and cosmetic industry. 1-Caprylaldehyde 1-Octaldehyde 1-Octanal 1-Octylaldehyde Aldehyde C-8 C-8 Aldehyde Caprylaldehyd Caprylaldehyde Caprylic aldehyde Kaprylaldehyd N-Caprylaldehyde N-Octaldehyde N-Octanal N-Octyl aldehyde N-Octylal Octan-1-al Octanaldehyde Octanoic aldehyde Octylaldehyd Octylaldehyde Oktanal Oktylaldehyd Aldehyde C8 Antifoam-LF Octaldehyde Octanal C8H16O 128.21 128.1201 octanal octanal 124-13-0 CCCCCCCC=O InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3 NUJGJRNETVAIRJ-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide Fatty aldehydes Fatty aldehydes an <i>n</i>-alkanal fatty aldehyde water_solubility 0.56 mg/mL melting_point -23 °C boiling_point 171 °C Wikipedia logp 3.19 ALOGPS logs -2.65 ALOGPS logp 2.54 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac octanal ChemAxon average_mass 128.21 ChemAxon mono_mass 128.1201 ChemAxon smiles CCCCCCCC=O ChemAxon formula C8H16O ChemAxon inchi InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3 ChemAxon inchikey NUJGJRNETVAIRJ-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 39.35 ChemAxon polarizability 16.45 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01545 FDB003339 441 17935 454 C00030880 CPD-371 Octanal 6033 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:29 UTC 2020-07-24 23:30:19 UTC CDB000173 4-Methyl-2-nonyl-1,3-dioxolane Decanal propyleneglycol acetal, also known as decanal or 4-methyl-2-nonyl-1,3-dioxolane, belongs to the class of organic compounds known as 1,3-dioxolanes. These are organic compounds containing 1,3-dioxolane, an aliphatic five-member ring with two oxygen atoms in ring positions 1 and 3. Decanal propyleneglycol acetal is a neutral compound, a colorless clear liquid with a floral, green herbal odor ( http://www.thegoodscentscompany.com/data/rw1383421.html#toorgano). Decanal propyleneglycol acetal is found in cannabis plants (PMID:6991645). C13H26O2 214.35 214.1933 (2S,4R)-4-methyl-2-nonyl-1,3-dioxolane (2S,4R)-4-methyl-2-nonyl-1,3-dioxolane 5421-12-5 CCCCCCCCC[C@H]1OC[C@@H](C)O1 InChI=1S/C13H26O2/c1-3-4-5-6-7-8-9-10-13-14-11-12(2)15-13/h12-13H,3-11H2,1-2H3/t12-,13+/m1/s1 SJLDHKPBFAHHSI-OLZOCXBDSA-N belongs to the class of organic compounds known as 1,3-dioxolanes. These are organic compounds containing 1,3-dioxolane, an aliphatic five-member ring with two oxygen atoms in ring positions 1 and 3. 1,3-dioxolanes Organic compounds Organoheterocyclic compounds Dioxolanes 1,3-dioxolanes Aliphatic heteromonocyclic compounds Acetals Hydrocarbon derivatives Oxacyclic compounds Acetal Aliphatic heteromonocyclic compound Hydrocarbon derivative Meta-dioxolane Organic oxygen compound Organooxygen compound Oxacycle logp 4.22 ALOGPS logs -4.30 ALOGPS logp 4.41 ChemAxon pka_strongest_basic -4 ChemAxon iupac (2S,4R)-4-methyl-2-nonyl-1,3-dioxolane ChemAxon average_mass 214.35 ChemAxon mono_mass 214.1933 ChemAxon smiles CCCCCCCCC[C@H]1OC[C@@H](C)O1 ChemAxon formula C13H26O2 ChemAxon inchi InChI=1S/C13H26O2/c1-3-4-5-6-7-8-9-10-13-14-11-12(2)15-13/h12-13H,3-11H2,1-2H3/t12-,13+/m1/s1 ChemAxon inchikey SJLDHKPBFAHHSI-OLZOCXBDSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 62.83 ChemAxon polarizability 27.78 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 76959550 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:31 UTC 2020-08-04 22:28:12 UTC CDB000174 Laurylaldehyde Lauryl aldehyde also known as lauric aldehyde, belongs to the class of organic compounds known as medium-chain aldehydes, with a chain length between 6 and 12 carbon atoms. It has a dodecane backbone where the two hydrogens attached to a terminal carbon are replaced by an oxo group. Lauric aldehyde is a fatty aldehyde lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. It is a colorless to pale yellow clear liquid with an aldehydic, green, floral citrus, soapy, and waxy odor with a soapy, waxy, citrus, orange, mandarin flavor ( http://www.thegoodscentscompany.com/data/rw1000371.html#toorgano). Lauryl aldehyde is found in highest concentrations in corianders, sweet oranges, and lemons and in lower concentrations in mandarin orange (clementine, tangerine) and limes. Lauryl aldehyde has also been detected in fruits, mollusks, citrus, carrots, and wild celeries. This could make lauryl aldehyde a potential biomarker for the consumption of these foods. Lauryl aldehyde was found in cannabis plants (PMID:6991645). Dodecanaldehyde Dodecyl aldehyde Lauryl aldehyde Laurylaldehyde N-Dodecanal N-Dodecyl aldehyde N-Dodecylic aldehyde N-Lauraldehyde Dodecanal Lauraldehyde 1-Dodecanal 1-Dodecyl aldehyde Aldehyde C-12, lauric Aldehyde C12 C-12 Aldehyde, lauric C-12 Lauric aldehyde C12 Aldehyde Dodecylaldehyde Duodecylic aldehyde FEMA 2615 Lauraldehyde (8ci) Laurinaldehyde Lauric aldehyde C12H24O 184.32 184.1827 dodecanal dodecanal 112-54-9 CCCCCCCCCCCC=O InChI=1S/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h12H,2-11H2,1H3 HFJRKMMYBMWEAD-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide 2,3-saturated fatty aldehyde Fatty aldehydes Fatty aldehydes a fatty aldehyde long-chain fatty aldehyde melting_point 44.5 °C logp 5.46 ALOGPS logs -5.31 ALOGPS logp 4.32 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac dodecanal ChemAxon average_mass 184.32 ChemAxon mono_mass 184.1827 ChemAxon smiles CCCCCCCCCCCC=O ChemAxon formula C12H24O ChemAxon inchi InChI=1S/C12H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h12H,2-11H2,1H3 ChemAxon inchikey HFJRKMMYBMWEAD-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 57.75 ChemAxon polarizability 24.86 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012137 7902 8194 27836 C02278 CPD-7880 C00030644 Dodecanal Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:34 UTC 2020-07-08 16:06:14 UTC CDB000175 4-Ethylbenzaldehyde 4-Ethylbenzaldehyde, also known as benzaldehyde,4-ethyl or EBAL, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). 4-Ethylbenzaldehyde is a neutral compound. 4-Ethylbenzaldehyde is a colorless to pale yellow clear liquid with a bitter almond, sweet, anise, cherry odor (http://www.thegoodscentscompany.com/data/rw1038111.html#toorgano). 4-Ethylbenzaldehyde has been in alcoholic beverages, nuts, and tea. This could make 4-ethylbenzaldehyde a potential biomarker for the consumption of these foods. 4-Ethylbenzaldehye is a derivative of benzaldehyde. As a volatile component 4-ethylbenzaldehyde is found in plants such as cannabis (PMID: 6991645) and Z. mays (https://doi.org/10.1007/s11356-017-0140-x). 4-Ethyl-benzaldehyde BENZALDEHYDE,4-ethyl EBAL Ethyl benzaldehyde Ethyl-benzaldehyde FEMA 3756 p-Ethyl-benzaldehyde p-Ethylbenzaldehyde C9H10O 134.18 134.0732 4-ethylbenzaldehyde 4-ethylbenzaldehyde 4748-78-1 CCC1=CC=C(C=O)C=C1 InChI=1S/C9H10O/c1-2-8-3-5-9(7-10)6-4-8/h3-7H,2H2,1H3 QNGNSVIICDLXHT-UHFFFAOYSA-N belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Benzoyl derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives Aromatic homomonocyclic compounds Benzaldehydes Hydrocarbon derivatives Organic oxides Aldehyde Aromatic homomonocyclic compound Aryl-aldehyde Benzaldehyde Benzoyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound logp 2.71 ALOGPS logs -2.57 ALOGPS logp 2.64 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac 4-ethylbenzaldehyde ChemAxon average_mass 134.18 ChemAxon mono_mass 134.0732 ChemAxon smiles CCC1=CC=C(C=O)C=C1 ChemAxon formula C9H10O ChemAxon inchi InChI=1S/C9H10O/c1-2-8-3-5-9(7-10)6-4-8/h3-7H,2H2,1H3 ChemAxon inchikey QNGNSVIICDLXHT-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 42.28 ChemAxon polarizability 15.12 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008722 21105903 20861 4-Ethylbenzaldehyde Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:36 UTC 2020-08-04 22:28:12 UTC CDB000176 4-Hydroxybenzoic acid 4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl group. 4-Hydroxybenzoic acid is a neutral compound with a nutty and phenolic taste. 4-Hydroxybenzoic acid exists in all living species, from bacteria to humans. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. 4-Hydroxybenzoic acid is found in highest concentrations in red huckleberries, corianders, and garden onions and in lower concentrations in soybeans, rye bread, and almonds. 4-hydroxybenzoic acid has also been detected in sour cherries, common beans, wild carrots, common oregano, and soft-necked garlics. This could make 4-hydroxybenzoic acid a potential biomarker for the consumption of these foods. 4-Hydroxybenzoic acid is also found in cannabis plants (PMID:6991645). 4-Hydroxybenzoic acid esters, known as parabens, are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid. 4-Hydroxybenzoic acid has estrogenic activity and stimulated the growth of breast cancer cell lines (PMID: 16021681). It can be found in Escherichia coli as part of the ubiquinone pathway. In the first step of this pathway, chorismate lyase transforms chorismate into 4-hydroxybenzoate and pyruvate (PMID 1644758). In Pseudomonas sp., 4-hydroxybenzoate and chloride are produced when the enzyme 4-chlorobenzoate dehalogenase acts on the halide bond of 4-chlorobenzoate with H2O (PMID: 6497878). 4-Carboxyphenol p-HYDROXYBENZOIC ACID p-Salicylic acid Hydroxybenzoic acid Hydroxybenzenecarboxylic acid p-HYDROXYBENZOate p-Salicylate Hydroxybenzoate Hydroxybenzenecarboxylate 4-Hydroxybenzoate 4-Hydroxy-benzoate 4-Hydroxy-benzoesaeure 4-Hydroxy-benzoic acid p-Carboxyphenol p-Hydroxy-benzoate p-Hydroxy-benzoic acid Paraben-acid 4-Hydroxybenzoic acid, calcium salt 4-Hydroxybenzoic acid, dilithium salt 4-Hydroxybenzoic acid, disodium salt Para-hydroxybenzoic acid Sodium p-hydroxybenzoate tetrahydrate 4-Hydroxybenzoic acid, copper(2+)(1:1) salt 4-Hydroxybenzoic acid, dipotassium salt 4-Hydroxybenzoic acid, monopotassium salt 4-Hydroxybenzoic acid, monosodium salt 4-Hydroxybenzoic acid, monosodium salt, 11C-labeled 4-Hydroxybenzene carboxylic acid p-Hydroxyl benzoic acid C7H6O3 138.12 138.0317 4-hydroxybenzoic acid P-hydroxybenzoic acid 99-96-7 OC(=O)C1=CC=C(O)C=C1 InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) FJKROLUGYXJWQN-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Hydroxybenzoic acid derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organooxygen compounds 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Phenol monohydroxybenzoic acid water_solubility 5.0 mg/mL logp 1.58 HANSCH,C ET AL. (1995) logp 1.58 ALOGPS logs -1.06 ALOGPS logp 1.33 ChemAxon pka_strongest_acidic 4.38 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac 4-hydroxybenzoic acid ChemAxon average_mass 138.12 ChemAxon mono_mass 138.0317 ChemAxon smiles OC(=O)C1=CC=C(O)C=C1 ChemAxon formula C7H6O3 ChemAxon inchi InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) ChemAxon inchikey FJKROLUGYXJWQN-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 35.3 ChemAxon polarizability 12.94 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00156 132 FDB010508 DB04242 135 30763 418 C00000856 4-hydroxybenzoate 34069 4-Hydroxybenzoic_acid 5486 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Pugazhendhi D, Pope GS, Darbre PD: Oestrogenic activity of p-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines. J Appl Toxicol. 2005 Jul-Aug;25(4):301-9. doi: 10.1002/jat.1066. 16021681 Nichols BP, Green JM: Cloning and sequencing of Escherichia coli ubiC and purification of chorismate lyase. J Bacteriol. 1992 Aug;174(16):5309-16. doi: 10.1128/jb.174.16.5309-5316.1992. 1644758 Muller R, Thiele J, Klages U, Lingens F: Incorporation of [18O]water into 4-hydroxybenzoic acid in the reaction of 4-chlorobenzoate dehalogenase from pseudomonas spec. CBS 3. Biochem Biophys Res Commun. 1984 Oct 15;124(1):178-82. doi: 10.1016/0006-291x(84)90933-1. 6497878 1.0 2020-03-18 23:27:38 UTC 2020-11-04 16:20:29 UTC CDB000177 (E)-p-Coumaric acid trans-4-Coumaric acid or (e)-p-Coumaric acid, the trans-isomer of 4-coumaric acid, also known as 4-hydroxycinnamic acid, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing a cinnamic acid where the benzene ring is hydroxylated. 4-Hydroxycinnamic acid is a neutral compound. 4-Hydroxycinnamic acid exists in all living species, from bacteria to humans. 4-Hydroxycinnamic acid is found in highest concentrations in pepper (c. frutescens), pineapples, and sunflowers and in lower concentration in spinachs, kiwis, and sweet oranges. 4-Hydroxycinnamic acid has also been detected in wild rices, soursops, garden onions, hyssops, and avocado. This could make 4-hydroxycinnamic acid a potential biomarker for the consumption of these foods. 4-Hydroxycinnamic acid is also found in cannabis plants reported by Paris in 1973 ¬†(PMID: 6991645). (2E)-3-(4-Hydroxyphenyl)acrylic acid (e)-3-(4-Hydroxyphenyl)-2-propenoic acid (e)-p-Coumaric acid (e)-p-Hydroxycinnamic acid 4'-HYDROXYCINNAMIC ACID Naringeninic acid p-Coumaric acid trans-4-Hydroxycinnamic acid trans-p-Coumaric acid trans-p-Coumarinic acid trans-p-Hydroxycinnamate trans-p-Hydroxycinnamic acid trans-4-Hydroxycinnamate 4-Hydroxycinnamate (2E)-3-(4-Hydroxyphenyl)acrylate (e)-3-(4-Hydroxyphenyl)-2-propenoate (e)-p-Coumarate (e)-p-Hydroxycinnamate 4'-HYDROXYCINNAMate Naringeninate p-Coumarate trans-p-Coumarate trans-p-Coumarinate trans-4-Coumarate 3-(4-Hydroxyphenyl)-2-propenoate 3-(4-Hydroxyphenyl)-2-propenoic acid 3-(4-Hydroxyphenyl)acrylate 3-(4-Hydroxyphenyl)acrylic acid 4-Coumarate 4-Coumaric acid 4-Hydroxy cinnamate 4-Hydroxy cinnamic acid 4-Hydroxyphenylpropenoate 4-Hydroxyphenylpropenoic acid b-[4-Hydroxyphenyl]acrylate b-[4-Hydroxyphenyl]acrylic acid beta-[4-Hydroxyphenyl]acrylate beta-[4-Hydroxyphenyl]acrylic acid cis-p-Coumarate Hydroxycinnamate Hydroxycinnamic acid p-Cumarate p-Cumaric acid p-Hydroxycinnamate p-Hydroxycinnamic acid p-Hydroxyphenylacrylate p-Hydroxyphenylacrylic acid Para coumarate Para coumaric acid Para-coumarate Para-coumaric acid 4-Coumaric acid, (Z)-isomer 4-Coumaric acid, disodium salt 4-Coumaric acid, (e)-isomer p-Coumaryl alcohol trans-3-(4'-Hydroxyphenyl)-2-propenoic acid trans-HPPA (2E)-3-(4-Hydroxyphenyl)-2-propenoic acid (2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid (e)-3-(4-Hydroxyphenyl)acrylic acid (e)-4-Hydroxycinnamic acid 4’-hydroxycinnamic acid p-Hydroxy-trans-cinnamic acid p-trans-Coumaric acid trans-3-(4-Hydroxyphenyl)-2-propenoic acid trans-4-Coumaric acid Β-[4-hydroxyphenyl]acrylic acid 4-Hydroxycinnamic acid (4-Hydroxyphenyl)acrylic acid Coumaric acid C9H8O3 164.16 164.0473 (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid coumaric acid 501-98-4 OC(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ NGSWKAQJJWESNS-ZZXKWVIFSA-N belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Hydroxycinnamic acids Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Cinnamic acids Coumaric acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Styrenes 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Coumaric acid Coumaric acid or derivatives Hydrocarbon derivative Hydroxycinnamic acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Styrene 4-coumaric acid Paracoumaryl alcohol derivatives logp 1.79 SANGSTER (1994) melting_point 211.5 °C logp 1.74 ALOGPS logs -2.21 ALOGPS logp 1.83 ChemAxon pka_strongest_acidic 4 ChemAxon pka_strongest_basic -6 ChemAxon iupac (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 164.16 ChemAxon mono_mass 164.0473 ChemAxon smiles OC(=O)\C=C\C1=CC=C(O)C=C1 ChemAxon formula C9H8O3 ChemAxon inchi InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+ ChemAxon inchikey NGSWKAQJJWESNS-ZZXKWVIFSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 45.04 ChemAxon polarizability 16.43 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04066 FDB002593 637542 553148 32374 C00811 500 C00000580 COUMARATE 36077 P-Coumaric_acid 6450 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:40 UTC 2020-07-31 20:34:13 UTC CDB000178 alpha-Linolenic acid alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Omega-3 fatty acids get their name based on the location of one of their first double bonds. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are rich in alpha-linolenic acid. Linolenic acid is a fatty acid found in hemp seed oil of cannabis plants, first reported by Prior et al. in 1968 (PMID: 6991645). Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of several genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Patients with isovaleric acidemia have a defect in leucine catabolism resulting from a deficiency in the enzyme isovaleryl-CoA dehydrogenase. These patients do well on a low protein/low leucine diet but a low protein diet can lead to deficiencies in essential fatty acids, such as alpha-linolenic acid ( https://doi.org/10.1038/ejcn.2016.100). (9,12,15)-Linolenic acid (9Z,12Z,15Z)-Octadecatrienoic acid (Z,Z,Z)-9,12,15-Octadecatrienoic acid 9,12,15-Octadecatrienoic acid 9-cis,12-cis,15-cis-Octadecatrienoic acid ALA all-cis-9,12,15-Octadecatrienoic acid cis,cis,cis-9,12,15-Octadecatrienoic acid cis-Delta(9,12,15)-Octadecatrienoic acid Linolenic acid Linolenate alpha-Linolenate (9,12,15)-Linolenate (9Z,12Z,15Z)-Octadecatrienoate (Z,Z,Z)-9,12,15-Octadecatrienoate 9,12,15-Octadecatrienoate 9-cis,12-cis,15-cis-Octadecatrienoate all-cis-9,12,15-Octadecatrienoate cis,cis,cis-9,12,15-Octadecatrienoate cis-delta(9,12,15)-Octadecatrienoate cis-Δ(9,12,15)-octadecatrienoate cis-Δ(9,12,15)-octadecatrienoic acid a-Linolenate a-Linolenic acid Α-linolenate Α-linolenic acid alpha Linolenic acid cis-9,12,15-Octadecatrienoate cis-9,12,15-Octadecatrienoic acid Industrene 120 FA(18:3(9Z,12Z,15Z)) FA(18:3n3) C18H30O2 278.43 278.2246 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid α linolenic acid 463-40-1 CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- DTOSIQBPPRVQHS-PDBXOOCHSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Polyunsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids linolenic acid omega-3 fatty acid logp 6.46 SANGSTER (1993) melting_point -16.5 °C logp 6.62 ALOGPS logs -6.02 ALOGPS logp 6.06 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid ChemAxon average_mass 278.43 ChemAxon mono_mass 278.2246 ChemAxon smiles CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O ChemAxon formula C18H30O2 ChemAxon inchi InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- ChemAxon inchikey DTOSIQBPPRVQHS-PDBXOOCHSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 89.64 ChemAxon polarizability 34.98 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C06427 FDB012462 4444437 5280934 DB00132 27432 LINOLENIC_ACID C00007247 Alpha-Linolenic_acid 48237 6208 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:43 UTC 2020-07-07 15:56:03 UTC CDB000179 (Z)-3-Hexenyl hexanoate cis-3-Hexenyl hexanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. cis-3-Hexenyl hexanoate is very hydrophobic, practically insoluble in water, and relatively neutral. cis-3-Hexenyl hexanoate has a fruity, grassy, and green taste. cis-3-Hexenyl hexanoate has been detected in citrus, fruits, herbs and spices, and tea. This could make cis-3-hexenyl hexanoate a potential biomarker for the consumption of these foods. cis-3-Hexenyl hexanoate is the main volatile compound that gives passion fruit its distinctive aroma (https://doi.org/10.1590/S0101-20612011000200023). It is also found in cannabis plants (PMID:6991645) and in medical plants such as Chamomile (Matricaria recutita L. (https://doi: 10.1021/bk-1993-0525.ch020). cis-3-Hexenyl hexanoic acid (3Z)-3-Hexenyl hexanoate (Z)-3-Hexen-1-ol, hexanoate (Z)-3-Hexenyl hexanoate (Z)-Hex-3-enyl hexanoate 3-Hexen-1-ol hexanoate, cis 3-Hexenyl ester(Z)-hexanoic acid cis-3-Hexenyl caproate cis-3-Hexenyl caproate (hexanoate) cis-3-Hexenyl hexoate cis-3-Hexenyl N-hexanoate cis-beta -Hexenyl caproate cis-Hexanoic acid, 3-hexenyl ester FEMA 3403 Hexanoate(Z)-3-hexen-1-ol Hexanoic acid, (3Z)-3-hexen-1-yl ester Hexanoic acid, (3Z)-3-hexenyl ester Hexanoic acid, 3-hexenyl ester N-Caproic acid cis-3-hexenyl ester (Z)-3-Hexenyl hexanoic acid C12H22O2 198.3 198.162 (3Z)-hex-3-en-1-yl hexanoate (3Z)-hex-3-en-1-yl hexanoate 31501-11-8 CCCCCC(=O)OCC\C=C/CC InChI=1S/C12H22O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h5,7H,3-4,6,8-11H2,1-2H3/b7-5- RGACQXBDYBCJCY-ALCCZGGFSA-N belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Fatty acid esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters logp 4.41 ALOGPS logs -3.92 ALOGPS logp 3.81 ChemAxon pka_strongest_basic -7 ChemAxon iupac (3Z)-hex-3-en-1-yl hexanoate ChemAxon average_mass 198.3 ChemAxon mono_mass 198.162 ChemAxon smiles CCCCCC(=O)OCC\C=C/CC ChemAxon formula C12H22O2 ChemAxon inchi InChI=1S/C12H22O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h5,7H,3-4,6,8-11H2,1-2H3/b7-5- ChemAxon inchikey RGACQXBDYBCJCY-ALCCZGGFSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 60.03 ChemAxon polarizability 24.38 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB011408 4509415 5352543 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:45 UTC 2020-07-07 15:56:04 UTC CDB000180 Hexyl hexanoate Hexyl hexanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Hexyl hexanoate is very hydrophobic, practically insoluble in water, and relatively neutral. Hexyl hexanoate has an apple peel, cut grass, and fresh taste. Hexyl hexanoate is found in highest concentration in passion fruits. Hexyl hexanoate has also been detected in milk and milk products, pomes, citrus, asian pears, and apples. This could make hexyl hexanoate a potential biomarker for the consumption of these foods. Hexyl hexanoate is also found in cannabis plants (PMID:6991645). Hexyl hexanoic acid Capryl caproate FEMA 2572 Hexanoic acid, hexyl ester Hexyl caproate Hexyl hexoate Hexyl N-hexanoate N-Hexyl hexanoate N-Hexyl N-hexanoate C12H24O2 200.32 200.1776 hexyl hexanoate hexanoic acid, hexyl ester 6378-65-0 CCCCCCOC(=O)CCCCC InChI=1S/C12H24O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h3-11H2,1-2H3 NCDCLPBOMHPFCV-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Fatty acid esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters logp 4.71 ALOGPS logs -4.22 ALOGPS logp 4.17 ChemAxon pka_strongest_basic -7 ChemAxon iupac hexyl hexanoate ChemAxon average_mass 200.32 ChemAxon mono_mass 200.1776 ChemAxon smiles CCCCCCOC(=O)CCCCC ChemAxon formula C12H24O2 ChemAxon inchi InChI=1S/C12H24O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h3-11H2,1-2H3 ChemAxon inchikey NCDCLPBOMHPFCV-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 58.92 ChemAxon polarizability 25.67 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21430 FDB011707 22873 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:47 UTC 2020-07-07 15:56:04 UTC CDB000181 Hexyl 2-methylpropanoate Hexyl 2-methylpropanoate, also known as Hexyl isobutyrate, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Hexyl 2-methylpropanoate is neutral compound. Hexyl 2-methylpropanoate has a sweet, apple, and berry taste. Hexyl 2-methylpropanoate is found in highest concentrations in milk (cow). Hexyl 2-methylpropanoate has also been detected in evergreen blackberries. This could make hexyl 2-methylpropanoate a potential biomarker for the consumption of these foods. Hexyl 2-methylpropanoate is also found in cannabis plants (PMID:6991645) and in giant hogweed (Heracleum mantegazzianum) essential oil (PMID: 30682808). Hexyl 2-methylpropanoic acid (Phenylmethyl)-penicillin (Phenylmethyl)-penicillinic acid (Phenylmethyl)penicillin (Phenylmethyl)penicillinic acid 1-Hexyl isobutyrate Abbocillin Benzopenicillin Benzyl-6-aminopenicillinic acid Benzyl-penicillinic acid Benzylpenicillin Benzylpenicillin g Benzylpenicillinic acid Caproyl isobutyrate Cilloral Cilopen Compocillin g Cosmopen Dropcillin Free benzylpenicillin Free penicillin g Free penicillin II Galofak Gelacillin Hexyl isobutanoate Hexyl isobutyrate Isobutyric acid, hexyl ester Liquacillin N-Hexyl isobutanoate N-Hexyl isobutyrate Penicillin Penicillin g Penicillin g potassium salt Pentids Pharmacillin Phenylacetamidopenicillanic acid Pradupen Specilline g C10H20O2 172.26 172.1463 hexyl 2-methylpropanoate hexyl 2-methylpropanoate 2349-07-7 CCCCCCOC(=O)C(C)C InChI=1S/C10H20O2/c1-4-5-6-7-8-12-10(11)9(2)3/h9H,4-8H2,1-3H3 CYHBDKTZDLSRMY-UHFFFAOYSA-N belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Carboxylic acid esters Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 3.90 ALOGPS logs -3.11 ALOGPS logp 3.38 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac hexyl 2-methylpropanoate ChemAxon average_mass 172.26 ChemAxon mono_mass 172.1463 ChemAxon smiles CCCCCCOC(=O)C(C)C ChemAxon formula C10H20O2 ChemAxon inchi InChI=1S/C10H20O2/c1-4-5-6-7-8-12-10(11)9(2)3/h9H,4-8H2,1-3H3 ChemAxon inchikey CYHBDKTZDLSRMY-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 49.69 ChemAxon polarizability 21.56 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB017000 15988 16872 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Matouskova M, Jurova J, Grulova D, Wajs-Bonikowska A, Renco M, Sedlak V, Poracova J, Gogalova Z, Kalemba D: Phytotoxic Effect of Invasive Heracleum mantegazzianum Essential Oil on Dicot and Monocot Species. Molecules. 2019 Jan 24;24(3). pii: molecules24030425. doi: 10.3390/molecules24030425. 30682808 1.0 2020-03-18 23:27:49 UTC 2020-07-10 00:17:45 UTC CDB000182 Methyl hexadecanoic acid Methyl hexadecanoic acid, also known as palmitic acid methyl ester, belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O) OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Methyl hexadecanoic acid is very hydrophobic, practically insoluble in water, and relatively neutral. Methyl hexadecanoic acid has a fatty, oily, and waxy taste. Methyl hexadecanoic acid has been detected in cauliflowers, cloves, and evergreen blackberries. This could make methyl hexadecanoic acid a potential biomarker for the consumption of these foods. Methyl hexadecenoic acid is also found in cannabis plants (PMID:6991645) and in cannabis smoke (https://doi.org/10.1007/978-1-59259-947-9_2). Methyl hexadecanoic acid is volatilized during the combustion of cannabis. Methyl hexadecanoate Methyl palmitate Methyl palmitic acid Hexadecanoate methyl ester Hexadecanoic acid methyl ester Palmitic acid methyl ester Methyl hexadecanoic acid C17H34O2 270.45 270.2559 methyl hexadecanoate methyl hexadecanoate 112-39-0 CCCCCCCCCCCCCCCC(=O)OC InChI=1S/C17H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h3-16H2,1-2H3 FLIACVVOZYBSBS-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Fatty acid methyl esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Methyl esters Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid methyl ester Hydrocarbon derivative Methyl ester Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters fatty acid methyl ester logp 7.41 ALOGPS logs -6.56 ALOGPS logp 6.4 ChemAxon pka_strongest_basic -7 ChemAxon iupac methyl hexadecanoate ChemAxon average_mass 270.45 ChemAxon mono_mass 270.2559 ChemAxon smiles CCCCCCCCCCCCCCCC(=O)OC ChemAxon formula C17H34O2 ChemAxon inchi InChI=1S/C17H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h3-16H2,1-2H3 ChemAxon inchikey FLIACVVOZYBSBS-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 81.85 ChemAxon polarizability 36.41 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003050 8181 C16995 C00030755 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:51 UTC 2020-07-24 23:30:06 UTC CDB000183 Sitosterol Beta-sitosterol, also known as sitosterol or harzol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Beta-sitosterol is widely distributed in the plant kingdom and is a main dietary phytosterol (a plant sterol) found in vegetable oils, nuts, avocados and prepared foods, such as salad dressings. Beta-sitosterol is one of the phytosterols known to occur in Cannabis sativa (PMID: 6991645). Phytopharmacological extracts, commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea, contain mixtures of phytosterols, that includes Beta-sitosterol. However, these extracts also contain some sterols bonded with glucosides. While beta-sitosterol is the purported active constituent, beta-sitosterol-beta-D-glucoside is often detected. Thus, one or both metabolites may be the active components. Phytosterols, like cholesterol, contain double bonds that are susceptible to oxidation. Beta-sitosterol may have anti-carcinogenic and anti-atherogenic properties (PMID: 13129445, 11432711). Benign prostatic hyperplasia patients treated with beta-sitosterol, compared with placebo, had improved urinary symptom scores and flow measures (PMID: 10368239). Hyperandrogenic postmenopausal women, with higher risk of breast cancer because of their endocrine profiles, were placed on a plant food-based diet, to determine if eating a plant-based diet, rich in phytosterols, rather than animal-based diet, would have an increase in serum phytosterols. Compared to controls, women placed on the plant-based diet had increased serum phytosterols, particularly beta-sitosterol, suggesting that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID: 14652381). Beta-sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID: 12579296). Although the exact mechanism of action of beta-sitosterols in the above studies is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). (-)-beta-Sitosterol (24R)-Ethylcholest-5-en-3beta-ol (24R)-Stigmast-5-en-3beta-ol (3beta)-Stigmast-5-en-3-ol 22,23-Dihydrostigmasterol 24alpha-Ethylcholesterol alpha-Dihydrofucosterol Azuprostat beta-Sitosterin Cupreol Nimbosterol Triastonal (-)-b-Sitosterol (-)-β-Sitosterol b-Sitosterol β-Sitosterol (24R)-Ethylcholest-5-en-3b-ol (24R)-Ethylcholest-5-en-3β-ol (24R)-Stigmast-5-en-3b-ol (24R)-Stigmast-5-en-3β-ol (3b)-Stigmast-5-en-3-ol (3β)-Stigmast-5-en-3-ol 24a-Ethylcholesterol 24α-Ethylcholesterol a-Dihydrofucosterol α-Dihydrofucosterol b-Sitosterin β-Sitosterin 22,23-Dihydro-Stigmasterol a-Phytosterol alpha-Phytosterol Angelicin beta-Phytosterol Cinchol D5-Stigmasten-3b-ol Delta5-Stigmasten-3b-ol Harzol Phytosterol Prostasal Quebrachol Rhamnol sito-Lande Sitosterol Sobatum Stigmast-5-en-3-ol Stigmast-5-en-3b-ol 3beta-Sitosterol 24-Ethylcholest-5-en-3 beta-ol 24-Ethylcholesterol Clionasterol 3beta-Stigmast-5-en-3-ol Sitosterol, (3beta)-isomer beta-Sitosterol Stigmast-5-en-3beta-ol Stigmast-5-en-3β-ol delta5-Stigmasten-3beta-ol Δ5-Stigmasten-3β-ol α-Phytosterol Rhammol Δ5-Stigmasten-3beta-ol C29H50O 414.72 414.3862 (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol 83-46-5 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 KZJWDPNRJALLNS-VJSFXXLFSA-N belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmastanes and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Stigmastanes and derivatives Aliphatic homopolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids C24-propyl sterols and derivatives Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols Triterpenoids 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound C24-propyl-sterol-skeleton Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Stigmastane-skeleton Triterpenoid 3beta-sterol Stigmasterols and C24-ethyl derivatives Stigmasterols and C24-ethyl derivatives phytosterols stigmastane water_solubility 10 mg/mL melting_point 140 °C logp 7.27 ALOGPS logs -7.35 ALOGPS logp 7.84 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol ChemAxon average_mass 414.72 ChemAxon mono_mass 414.3862 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C ChemAxon formula C29H50O ChemAxon inchi InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 ChemAxon inchikey KZJWDPNRJALLNS-VJSFXXLFSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 129.77 ChemAxon polarizability 54.21 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012362 192962 C01753 222284 27693 CPD-4143 C00023770 Beta-Sitosterol 169 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75. doi: 10.1079/bjn2003956. 13129445 Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9. doi: 10.1097/00008469-200106000-00007. 11432711 Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83. doi: 10.1046/j.1464-410x.1999.00026.x. 10368239 Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5. doi: 10.1093/jn/133.12.4252. 14652381 Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500. 12579296 1.0 2020-03-18 23:27:54 UTC 2020-08-04 22:28:12 UTC CDB000184 (-)-Isoborneol (-)-Isoborneol, also known as borneol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Borneol can be synthesized by reducing camphor by the Meerwein‚ÄìPonndorf‚ÄìVerley reaction, a reversible, inexpensive process. The isomer isoborneol can be produced in the kinetically controlled reduction of camphor with sodium borohydride, which is fast and irreversible. (-)-Isoborneol is neutral compound, a white crystalline solid with a balsamic camphoreous herbal woody odor and camphoreous minty herbal earthy woody flavor ( http://www.thegoodscentscompany.com/data/rw1002092.html#toorgano). Borneol or isoborneol is a naturally occurring organic compound found in the essential oil of many plants such as camphorweed, mugwort, beautyberry, Ngai camphor, aromatic ginger and in cannabis plants (PMID:6991645). FEMA 2158 Borneol Isoborneol, (exo)-isomer Isoborneol, (1R-exo)-isomer Isoborneol, (endo)-isomer Isoborneol, (endo-(+-))-isomer Isoborneol, (1R-endo)-isomer Isoborneol (-)-(2R)-Isoborneol (-)-Bornan-2-exo-ol (1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol (R,R,R)-(-)-Isoborneol 2-exo-Bornyl alcohol Isobornyl alcohol exo-2-Hydroxy-1,7,7-trimethylnorbornane (-)-Isoborneol l-Isoborneol (±)-Isoborneol dl-Isoborneol NSC 26350 C10H18O 154.25 154.1358 (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 10334-13-1 CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2 InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 DTGKSKDOIYIVQL-MRTMQBJTSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Bornane monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol melting_point 212 °C logp 2.83 ALOGPS logs -2.28 ALOGPS logp 1.99 ChemAxon pka_strongest_acidic 19.6 ChemAxon pka_strongest_basic -0.78 ChemAxon iupac (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 ChemAxon inchikey DTGKSKDOIYIVQL-MRTMQBJTSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.31 ChemAxon polarizability 18.43 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014581 4882019 6321405 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-18 23:27:56 UTC 2020-07-07 15:56:07 UTC CDB000185 (R)-Camphor Camphor, also known as (+)-camphor or (+)-bornan-2-one, with the chemical formula C10H16O, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Camphor is a waxy, flammable, white or transparent solid with a strong aroma. Camphor is practically insoluble in water and a neutral compound. Within the cell, camphor is primarily located in the membrane. It is found in many plants, such as in the wood of the camphor laurel (Cinnamomum camphora), laurel (Ocotea usambarensis), Kapur tree, in the oil of rosemary leaves (Rosmarinus officinalis), the mint family (10 to 20% camphor), camphorweed (Heterotheca; 5%), camphor basil (the parent of African blue basil) and cannabis plants (PMID:6991645). Camphor can also be synthetically produced from oil of turpentine. Camphor is also used for its scent, as an ingredient in cooking (mainly in India), as an embalming fluid, for medicinal purposes, and in religious ceremonies. (+)-Bornan-2-one (+)-Camphor (1R)-(+)-Camphor (1R,4R)-Camphor (R)-(+)-Camphor Camphor(D) D-Camphor Camphora CAMPHOR (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one (1R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one (+)-(1R,4R)-Camphor (1R)-Camphor (1R,4R)-(+)-Camphor (R)-Camphor D-(+)-Camphor Alcanfor (+)-2-Bornanone (±)-Camphor 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one 1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone 1,7,7-Trimethylnorcamphor 2-Bornanone 2-Camphanone Alphanon Borneo camphor dl-Camphor C10H16O 152.23 152.1201 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (+)-camphor 464-49-3 CC1(C)[C@@H]2CC[C@@]1(C)C(=O)C2 InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m1/s1 DSSYKIVIOFKYAU-XCBNKYQSSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Hydrocarbon derivatives Ketones Organic oxides Aliphatic homopolycyclic compound Bicyclic monoterpenoid Bornane monoterpenoid Carbonyl group Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound camphor logp 2.85 ALOGPS logs -2.24 ALOGPS logp 2.55 ChemAxon pka_strongest_basic -7.5 ChemAxon iupac (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one ChemAxon average_mass 152.23 ChemAxon mono_mass 152.1201 ChemAxon smiles CC1(C)[C@@H]2CC[C@@]1(C)C(=O)C2 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m1/s1 ChemAxon inchikey DSSYKIVIOFKYAU-XCBNKYQSSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 44.49 ChemAxon polarizability 17.74 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB01744 159055 15396 CPD-862 C00000819 Camphor Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:27:58 UTC 2020-07-24 23:30:19 UTC CDB000186 Car-3-ene alpha-Carene, also known as 3-carene or Delta(3)-carene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. alpha-Carene is possibly neutral. alpha-Carene is a sweet, citrus, and lemon tasting compound. Outside of the human body, alpha-Carene is found, on average, in the highest concentration within a few different foods, such as common thymes, fennels, and cumins and in a lower concentration in pot marjorams, winter savories, and star anises. alpha-Carene has also been detected, but not quantified in, several different foods, such as sweet marjorams, yellow bell peppers, red bell peppers, tarragons, and pepper (c. frutescens). This could make alpha-carene a potential biomarker for the consumption of these foods. Delta(3)-carene is also found in cannabis plants (PMID: 6991645). 3-Carene is a colorless compound with a sweet, penetrating odor and is predominantly used in the perfume industry for producing essential oils. It is also an intermediate in perfume synthesis and a precursor for insecticides of the pyrethroid type (https://doi.org/10.1002%2F14356007.a26_205). C10H16 136.24 136.1252 (1R,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene (1R,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene 74806-04-5 CC1=CC[C@@H]2[C@@H](C1)C2(C)C InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 BQOFWKZOCNGFEC-RKDXNWHRSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Carane monoterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 3.64 ALOGPS logs -2.96 ALOGPS logp 2.8 ChemAxon iupac (1R,6R)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC1=CC[C@@H]2[C@@H](C1)C2(C)C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 ChemAxon inchikey BQOFWKZOCNGFEC-RKDXNWHRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.72 ChemAxon polarizability 17.5 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12302455 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:01 UTC 2020-08-04 22:28:12 UTC CDB000187 beta-Cyclocitral beta-Cyclocitral, also known as Œ≤-cyclocitral, belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. beta-Cyclocitral is neutral compound, colorless to pale yellow clear liquid with is a tropical, saffron, herbal, clean, rose, oxide, sweet, tobacco damascene, fruity odor and tropical saffron herbal tobacco medicinal phenolic leathery green flavor ( http://www.thegoodscentscompany.com/data/rw1037211.html#toorgano). beta-cyclocitral is found in highest concentrations in orange mints and safflowers and has also been detected in figs, herbs and spices, oats, and tea. This could make beta-cyclocitral a potential biomarker for the consumption of these foods. beta-Cyclocitral is also found in cannabis plants (PMID: 6991645). beta-Cyclocitral has been identified endogenously in dozens of plant species, including tomato, rice, parsley, grape, various trees, and moss. In one study, Œ≤-Cyclocitral, a small molecule derived from Œ≤-carotene, was identified as a regulator of root stem cell behavior in Arabidopsis as well as in rice and tomato (PMID: 31068462). 2,6,6-Trimethyl-1-cyclohexene-1-carboxaldehyde 2,6,6-Trimethyl-1-cyclohexene-1-carbaldehyde b-Cyclocitral Β-cyclocitral 1-Formyl-2,6,6-trimethyl-1-cyclohexene 2,6,6-Trimethyl-1-cyclohexen-1-carboxaldehyde 2,6,6-Trimethyl-cyclohexene-1-carboxaldehyde 2,6,6-Trimethyl-cyclohexenecarboxaldehyde 2,6,6-Trimethylcyclohex-1-ene-1-carbaldehyde 2,6,6-Trimethylcyclohexene-1-carbaldehyde 2,6,6-Trimethylcyclohexenecarbaldehyde alpha(beta)-Cyclocitral beta -Cyclocitral beta-Cyclocitrol C10H16O 152.23 152.1201 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde β-cyclocitral 432-25-7 CC1=C(C=O)C(C)(C)CCC1 InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3 MOQGCGNUWBPGTQ-UHFFFAOYSA-N belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. Organic oxides Organic compounds Organic oxygen compounds Organic oxides Aliphatic homomonocyclic compounds Aldehydes Hydrocarbon derivatives Aldehyde Aliphatic homomonocyclic compound Carbonyl group Hydrocarbon derivative Organic oxide Organooxygen compound monoterpenoid logp 2.96 ALOGPS logs -2.08 ALOGPS logp 2.41 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde ChemAxon average_mass 152.23 ChemAxon mono_mass 152.1201 ChemAxon smiles CC1=C(C=O)C(C)(C)CCC1 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3 ChemAxon inchikey MOQGCGNUWBPGTQ-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 47.1 ChemAxon polarizability 18.03 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB020874 9511 9895 C20425 53177 C00042278 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Dickinson AJ, Lehner K, Mi J, Jia KP, Mijar M, Dinneny J, Al-Babili S, Benfey PN: beta-Cyclocitral is a conserved root growth regulator. Proc Natl Acad Sci U S A. 2019 May 21;116(21):10563-10567. doi: 10.1073/pnas.1821445116. Epub 2019 May 8. 31068462 1.0 2020-03-18 23:28:03 UTC 2020-07-24 23:30:19 UTC CDB000188 1,4-Cineole 1,4-Cineole belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 1,4-Cineole is neutral compound. It is a colorless clear liquid with a minty, cooling piney, camphoraceous, eucalyptol-like odor and a flavor described as cooling, minty, menthol-like, green and herbal, with a terpy and camphoraceous nuance. 1,4-Cineole is found in highest concentrations in lavender spike water, juniper needle oil, cardamoms and limes. 1,4-Cineole has also been detected in evergreen grapes, grapefruit juice, lemon, orange, mandarins, blackberries, herbs and spices, roselles, and star anises (http://www.thegoodscentscompany.com/data/rw1029041.html#tooccur). This could make 1,4-cineole a potential biomarker for the consumption of these foods. 1,4-Cineole is also found in cannabis plants (PMID:6991645) and in the essential oil of Rhododendron anthopogonoides (PMID: 22143541). (1S,4S)-1-Methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane 1,4-Cineol 1,4-Epoxy-p-menthane 1-Isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptane 1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane Isocineole Isocineple C10H18O 154.25 154.1358 (1s,4s)-1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane (1s,4s)-1-isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptane 470-67-7 CC(C)[C@]12CC[C@](C)(CC1)O2 InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3/t9-,10+ RFFOTVCVTJUTAD-AOOOYVTPSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic heteropolycyclic compounds Dialkyl ethers Hydrocarbon derivatives Menthane monoterpenoids Oxacyclic compounds Tetrahydrofurans Aliphatic heteropolycyclic compound Bicyclic monoterpenoid Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle P-menthane monoterpenoid Tetrahydrofuran logp 2.31 ALOGPS logs -3.43 ALOGPS logp 2.5 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1s,4s)-1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)[C@]12CC[C@](C)(CC1)O2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3/t9-,10+ ChemAxon inchikey RFFOTVCVTJUTAD-AOOOYVTPSA-N ChemAxon polar_surface_area 9.23 ChemAxon refractivity 45.71 ChemAxon polarizability 18.9 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 80788 C00010825 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Yang K, Zhou YX, Wang CF, Du SS, Deng ZW, Liu QZ, Liu ZL: Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais. Molecules. 2011 Aug 25;16(9):7320-30. doi: 10.3390/molecules16097320. 22143541 1.0 2020-03-18 23:28:05 UTC 2020-09-11 20:08:26 UTC CDB000189 Eucalyptol 1,8-Cineole also known as Eucalyptol, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-membered saturated aliphatic heterocycle, composed of one oxygen atom and five carbon atoms. Eucalyptol is an organic compound that is a colourless liquid. It is a cyclic ether and a monoterpenoid. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fractions. Eucalyptus oil is the oil extracted from the leaves of various Eucalyptus species. Eucalyptol oil is used for its aromatic properties and as an ingredient in pharmaceutical and industrial applications. Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products, and beverages. Eucalyptol was given GRAS (Generally Recognized as Safe) status by the Flavor and Extract Manufacturer's Association FEMA in 1965 and is approved by the Food and Drug Administration for food use. 1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole, and 3-hydroxy-cineole are the main metabolites of eucalyptol. Toxicological data available on eucalyptol is rather limited. Following accidental exposure, death was reported in two cases after ingestion of 3.5-5 mL of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is added to improve the flavour (PMID: 12048025). Eucalyptol is found in many foods, some of which are common thyme, caraway, sunflower, and pot marjoram. Eucalyptol can also be found in the volatile fraction of Cannabis sativa (PMID: 26657499) and is likely a component of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 1,3,3-TRIMETHYL-2-oxabicyclo[2.2.2]octane 1,8-Cineol 1,8-Epoxy-p-menthane 1,8-Oxido-p-menthane Cajeputol Cineole Zineol 1,8-Cineole 1,8-Eucalyptol 2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane Eucaliptol Eucalyptole Eucalytol Eukalyptol p-Cineole Eucalyptol Cineol Eucapur Terpan C10H18O 154.25 154.1358 (1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane 1,8-cineole 470-82-6 C[C@@]12CC[C@@H](CC1)C(C)(C)O2 InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10+ WEEGYLXZBRQIMU-WAAGHKOSSA-N belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Oxanes Organic compounds Organoheterocyclic compounds Oxanes Aliphatic heteropolycyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteropolycyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Oxane cineole water_solubility 3.5 mg/mL at 21 °C logp 2.74 GRIFFIN,S ET AL. (1999) melting_point 1.5 °C boiling_point 176–177 °C Wikipedia logp 3.36 ALOGPS logs -3.84 ALOGPS logp 2.35 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles C[C@@]12CC[C@@H](CC1)C(C)(C)O2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10+ ChemAxon inchikey WEEGYLXZBRQIMU-WAAGHKOSSA-N ChemAxon polar_surface_area 9.23 ChemAxon refractivity 45.86 ChemAxon polarizability 18.54 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C09844 FDB014616 21111689 27961 DB03852 C00000136 Eucalyptol CPD-4261 De Vincenzi M, Silano M, De Vincenzi A, Maialetti F, Scazzocchio B: Constituents of aromatic plants: eucalyptol. Fitoterapia. 2002 Jun;73(3):269-75. doi: 10.1016/s0367-326x(02)00062-x. 12048025 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-18 23:28:07 UTC 2020-07-24 23:30:06 UTC CDB000190 Neral 3,7-dimethyl-2,6-octadienal or citral, also known as lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as geranial or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba, lemongrass (65-80%), lemon tea-tree (70-80%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has also been reported to be found in Cannabis sativa (PMID: 6991645, 26657499). Citral has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID: 28974979) and pheromonal effects in nematodes and insects (PMID: 26973536). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke). Citral b Lemonal Neral (Z)-Citral Citral (2Z)-3,7-Dimethyl-2,6-octadien-1-al (2Z)-3,7-Dimethyl-2,6-octadienal (Z)-3,7-Dimethyl-2,6-octadienal (Z)-Neral 2-cis-3,7-Dimethyl-2,6-octadienal 3,7-Dimethyl-2,6-octadien-1-al 3,7-Dimethyl-2,6-octadienal beta-Citral cis-3,7-Dimethyl-2,6-octadienal cis-Geranial Β-citral cis-Citral C10H16O 152.24 152.1201 (2Z)-3,7-dimethylocta-2,6-dienal neral 106-26-3 CC(C)=CCC\C(C)=C/C=O InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7- WTEVQBCEXWBHNA-YFHOEESVSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Enals Hydrocarbon derivatives Medium-chain aldehydes Organic oxides Acyclic monoterpenoid Aldehyde Aliphatic acyclic compound Alpha,beta-unsaturated aldehyde Carbonyl group Enal Hydrocarbon derivative Medium-chain aldehyde Organic oxide Organic oxygen compound Organooxygen compound Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes enal monoterpenoid boiling_point 229 °C Wikipedia logp 3.37 ALOGPS logs -2.58 ALOGPS logp 2.66 ChemAxon pka_strongest_basic -4.1 ChemAxon iupac (2Z)-3,7-dimethylocta-2,6-dienal ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles CC(C)=CCC\C(C)=C/C=O ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7- ChemAxon inchikey WTEVQBCEXWBHNA-YFHOEESVSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 50.12 ChemAxon polarizability 18.66 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013575 643779 C09847 29020 C00003036 CPD-9762 Neral Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Mokarizadeh M, Kafil HS, Ghanbarzadeh S, Alizadeh A, Hamishehkar H: Improvement of citral antimicrobial activity by incorporation into nanostructured lipid carriers: a potential application in food stuffs as a natural preservative. Res Pharm Sci. 2017 Oct;12(5):409-415. doi: 10.4103/1735-5362.213986. 28974979 Larsdotter-Mellstrom H, Eriksson K, Liblikas I I, Wiklund C, Borg-Karlson AK, Nylin S, Janz N, Carlsson MA: It's All in the Mix: Blend-Specific Behavioral Response to a Sexual Pheromone in a Butterfly. Front Physiol. 2016 Feb 29;7:68. doi: 10.3389/fphys.2016.00068. eCollection 2016. 26973536 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-18 23:28:09 UTC 2020-07-31 20:34:13 UTC CDB000191 2-(4-Methylphenyl)-2-propanol 2-(4-Methylphenyl)-2-propanol or 2-(4-Methylphenyl)propan-2-ol, also known as cymen-8-ol or 8-p-cymenol, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 2-(4-Methylphenyl)-2-propanol is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-(4-Methylphenyl)-2-propanol is a sweet, camphor, and cherry tasting compound. Outside of the human body, 2-(4-Methylphenyl)-2-propanol is found, on average, in the highest concentration within a few different foods, such as wild carrots, carrots, and star anises and in a lower concentration in sweet marjorams, rosemaries, and parsley. 2-(4-Methylphenyl)-2-propanol has also been detected, but not quantified in, several different foods, such as fruits, citrus, garden tomato, garden tomato (var.), and common oregano. This could make 2-(4-methylphenyl)-2-propanol a potential biomarker for the consumption of these foods. 1-Methyl-4-(1-hydroxy-1-methylethyl)benzene 1-Methyl-4-(alpha-hydroxyisopropyl)benzene 2-(4-Methylphenyl)propan-2-ol 2-(p-Methylphenyl)-2-propanol 2-p-Tolyl-2-propanol 8-Hydroxy-p-cymene 8-p-Cymenol a,a,4-Trimethylbenzenemethanol, 9ci a,a,4-Trimethylbenzyl alcohol, 8ci a-Hydroxy-p-cymene alpha,alpha,4-Trimethyl-benzenemethanol alpha,alpha,4-Trimethylbenzenemethanol alpha,alpha,4-Trimethylbenzyl alcohol Cimen-8-ol Cymen-8-ol Dimethyl-p-tolyl carbinol Dimethyl-p-tolylcarbinol FEMA 3242 Laquo rhoraquo -cymene-8-ol p,alpha,alpha-Trimethylbenzyl alcohol p-(Hydroxyisopropyl)toluene p-Cymen-8-ol p-Cymen-alpha-ol p-Cymene-8-ol p-Cymenol p-Cymenol-8 p-Mentha-1,3,5-trien-8-ol Para-cymen-8-ol 4-Cymen-8-ol C10H14O 150.22 150.1045 2-(4-methylphenyl)propan-2-ol terpineol 1197-01-9 CC1=CC=C(C=C1)C(C)(C)O InChI=1S/C10H14O/c1-8-4-6-9(7-5-8)10(2,3)11/h4-7,11H,1-3H3 XLPDVYGDNRIQFV-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenylpropanes Organic compounds Benzenoids Benzene and substituted derivatives Phenylpropanes Aromatic homomonocyclic compounds Aromatic alcohols Hydrocarbon derivatives Tertiary alcohols Toluenes Alcohol Aromatic alcohol Aromatic homomonocyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Phenylpropane Tertiary alcohol Toluene melting_point 9 °C logp 2.53 ALOGPS logs -2.09 ALOGPS logp 2.42 ChemAxon pka_strongest_acidic 14.63 ChemAxon pka_strongest_basic -3 ChemAxon iupac 2-(4-methylphenyl)propan-2-ol ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC1=CC=C(C=C1)C(C)(C)O ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-8-4-6-9(7-5-8)10(2,3)11/h4-7,11H,1-3H3 ChemAxon inchikey XLPDVYGDNRIQFV-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 46.97 ChemAxon polarizability 17.77 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 14529 FDB000826 13872 C00030933 1.0 2020-03-18 23:28:11 UTC 2020-07-24 23:30:19 UTC CDB000192 2-Methyl-5-(prop-1-en-2-yl)cyclohexyl acetate Dihydrocarveol acetate, also known as 8-p-menthen-2-yl acetate or carhydrine, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Dihydrocarveol acetate is neutral compound. Dihydrocarveol acetate has a sweet, camphor, and cuminseed taste. Dihydrocarveol acetate is found in highest concentrations in spearmints and caraway. Dihydrocarveol acetate has also been detected in anises, celery stalks, and wild celeries. This could make dihydrocarveol acetate a potential biomarker for the consumption of these foods. Dihydrocarveol acetate is also found in cannabis plants (PMID:6991645). C12H20O2 196.29 196.1463 (1S,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexyl acetate (1S,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexyl acetate 20405-60-1 C[C@@H]1CC[C@H](C[C@@H]1OC(C)=O)C(C)=C InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11-,12+/m1/s1 TUSIZTVSUSBSQI-JLLWLGSASA-N logp 3.46 ALOGPS logs -3.09 ALOGPS logp 2.76 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1S,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexyl acetate ChemAxon average_mass 196.29 ChemAxon mono_mass 196.1463 ChemAxon smiles C[C@@H]1CC[C@H](C[C@@H]1OC(C)=O)C(C)=C ChemAxon formula C12H20O2 ChemAxon inchi InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11-,12+/m1/s1 ChemAxon inchikey TUSIZTVSUSBSQI-JLLWLGSASA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 56.37 ChemAxon polarizability 22.91 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7058095 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:14 UTC 2020-07-24 23:30:06 UTC CDB000193 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol Fenchol or 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchol is a naturally occurring bicyclic monoterpenoid and an isomer of Borneol. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclation reactions to yield a diverse number of cyclic arrangements. Fenchol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white solid with a characteristic scent found in basil and Aster and cannabis plants (PMID:6991645). Fenchol is used extensively in perfumery. (1S,2-endo)-1,3,3-Trimethylnorbornan-2-ol (1S,2S,4R)-endo-Fenchol 1,3,3-Trimethyl-2-norbornanol 2-Fenchanol alpha-Fenchol alpha-Fenchyl alcohol endo-alpha-Fenchol endo-Fenchol Fenchyl alcohol (-)-alpha-Fenchyl alcohol a-Fenchol Α-fenchol a-Fenchyl alcohol Α-fenchyl alcohol endo-a-Fenchol endo-Α-fenchol (-)-a-Fenchyl alcohol (-)-Α-fenchyl alcohol a-Fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol Α-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol Fenchol, ((endo)-(+-))-isomer Fenchol, ((exo)-(+-))-isomer Fenchol, (endo)-isomer Fenchol, (1R-endo)-isomer Fenchol, (1S-exo)-isomer Fenchol Fenchol, (1S-endo)-isomer Fenchol, (exo)-isomer (1S,2S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol (-)-endo-Fenchol (-)-alpha-Fenchol (-)-α-Fenchol (1S-endo)-Fenchol l-alpha-Fenchyl alcohol l-α-Fenchyl alcohol rel-(1R,2R,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol (±)-alpha-Fenchol (±)-α-Fenchol dl-alpha-Fenchol dl-α-Fenchol 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol C10H18O 154.25 154.1358 (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol ((endo)-(+-))-fenchol 2217-02-9 CC1(C)[C@@H]2CC[C@@](C)(C2)[C@@H]1O InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 IAIHUHQCLTYTSF-MRTMQBJTSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Fenchane monoterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Bicyclic monoterpenoids carbobicyclic compound fenchane monoterpenoid logp 2.30 ALOGPS logs -2.25 ALOGPS logp 2.15 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac (1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@@H]2CC[C@@](C)(C2)[C@@H]1O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 ChemAxon inchikey IAIHUHQCLTYTSF-MRTMQBJTSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.16 ChemAxon polarizability 18.52 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB029688 439711 C02344 15405 C00035801 CPD-685 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:16 UTC 2020-07-07 15:56:12 UTC CDB000194 2E-Geraniol beta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Geraniol is a monoterpenoid and an alcohol found in cannabis plants (PMID:6991645). Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403) (2E)-3,7-Dimethyl-2,6-octadien-1-ol (e)-3,7-Dimethyl-2,6-octadien-1-ol (e)-Geraniol (e)-Nerol 2-trans-3,7-Dimethyl-2,6-octadien-1-ol 3,7-Dimethyl-trans-2,6-octadien-1-ol Geranyl alcohol Lemonol t-Geraniol trans-3,7-Dimethyl-2,6-octadien-1-ol trans-Geraniol b-Geraniol Β-geraniol (2E)-3,7-Dimethylocta-2,6-dien-1-ol 2-trans-3,7-Dimethyl-2,6-octadiene-1-ol 2E-Geraniol 3,7-Dimethyl-(2E)-2,6-octadien-1-ol 3,7-Dimethyl-(e)-2,6-octadien-1-ol FEMA 2507 Geraniol trans-2,6-Dimethyl-2,6-octadien-8-ol trans-3,7-Dimethy- octa-2,6-dien-1-ol Geraniol, (Z)-isomer Geraniol, 1-(14)C-labeled, (e)-isomer Nerol Geraniol, 2-(14)C-labeled, (e)-isomer Geraniol, titanium (4+) salt Geraniol, (e)-isomer (E)-3,7-Dimethyl-2,6-octadienol trans-1-Hydroxy-3,7-dimethyl-2,6-octadiene beta-Geraniol C10H18O 154.25 154.1358 (2E)-3,7-dimethylocta-2,6-dien-1-ol geraniol 106-24-1 CC(C)=CCC\C(C)=C\CO InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ GLZPCOQZEFWAFX-JXMROGBWSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Fatty alcohols Hydrocarbon derivatives Primary alcohols Acyclic monoterpenoid Alcohol Aliphatic acyclic compound Fatty acyl Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol 3,7-dimethylocta-2,6-dien-1-ol Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes monoterpenoid primary alcohol water_solubility 0.1 mg/mL at 25 °C logp 3.56 melting_point < -15 °C logp 2.89 ALOGPS logs -2.05 ALOGPS logp 2.5 ChemAxon pka_strongest_acidic 16.33 ChemAxon pka_strongest_basic -2.2 ChemAxon iupac (2E)-3,7-dimethylocta-2,6-dien-1-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)=CCC\C(C)=C\CO ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ ChemAxon inchikey GLZPCOQZEFWAFX-JXMROGBWSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 51.18 ChemAxon polarizability 19.67 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013792 13849989 637566 C01500 17447 C00000845 GERANIOL Geraniol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-18 23:28:18 UTC 2020-07-08 16:06:14 UTC CDB000195 (5Z)-6,10-Dimethylundeca-5,9-dien-2-one Geranylacetone or (5Z)-6,10-Dimethylundeca-5,9-dien-2-one, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Geranylacetone is neutral compound with . a citrus, earthy, and fatty taste. Geranylacetone is found in highest concentrations in wild carrots, carrots, and tortilla and in lower concentrations in corns. Geranylacetone has also been detected in figs, lemon grass, garden tomato (var.), tortilla chips, and papaya. This could make geranylacetone a potential biomarker for the consumption of these foods. Geranylacetone is found in cannabis plants (PMID:6991645) and is an industrial intermediate in the vitamin E synthesis (https://doi.org/10.1002%2F14356007.a26_205). (5E)-6,10-Dimethyl-5,9-undecadien-2-one (5E)-6,10-Dimethylundeca-5,9-dien-2-one (e)-6,10-Dimethyl-5,9- undecadien-2-one (e)-6,10-Dimethyl-5,9-undecadien-2-one (e)-6,10-Dimethylundeca-5,9-dien-2-one (e)-Geranyl acetone (e)-Geranylacetone 6,10-Dimethyl-(5E)-5,9-undecadien-2-one 6,10-Dimethyl-(e)-5,9-undecadien-2-one 6,10-Dimethyl-5,9-undecadien-2-one 6,10-Dimethyl-5,9-undecadien-2-one, (e) 6,10-Dimethyl-5,9-undecadiene-2-one 6,10-Dimethyl-undecadien-2-one 6,10-Dimethylundecadien-2-one Dihydropseudoionone FEMA 3542 Geranyl acetone Geranyl-acetone Geranylaceton Geranylgeranylacetone Teprenone trans-2,6-Dimethyl-2,6-undecadien-2-one trans-6,10-Dimethyl-5,9-undecadien-2-one trans-Geranylacetone Nerylacetone C13H22O 194.31 194.1671 (5Z)-6,10-dimethylundeca-5,9-dien-2-one (5Z)-6,10-dimethylundeca-5,9-dien-2-one 3796-70-1 CC(C)=CCC\C(C)=C/CCC(C)=O InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9- HNZUNIKWNYHEJJ-XFXZXTDPSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Ketones Organic oxides Acyclic monoterpenoid Aliphatic acyclic compound Carbonyl group Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound logp 4.59 ALOGPS logs -3.31 ALOGPS logp 3.68 ChemAxon pka_strongest_acidic 19.6 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac (5Z)-6,10-dimethylundeca-5,9-dien-2-one ChemAxon average_mass 194.31 ChemAxon mono_mass 194.1671 ChemAxon smiles CC(C)=CCC\C(C)=C/CCC(C)=O ChemAxon formula C13H22O ChemAxon inchi InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9- ChemAxon inchikey HNZUNIKWNYHEJJ-XFXZXTDPSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 63.83 ChemAxon polarizability 24.21 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008529 1362229 1713001 C00029336 C13297 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:22 UTC 2020-07-31 20:34:16 UTC CDB000197 (3R,6E)-Nerolidol (3R,6E)-Nerolidol or Nerolidol, also known as peruviol and penetrol , is a naturally occurring sesquiterpene alcohol found in the essential oils of many types of plants and flowers. It is formally classified as an alkylalcohol although it is biochemically an acyclic sesquiterpene as it synthesized via isoprene units. Acyclic sesequiterpenes do not contain a cycle. Nerolidol is an extremely weak basic (essentially neutral) compound (based on its pKa). There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. Nerolidol is present in neroli, ginger, jasmine, lavender, tea tree, Cannabis sativa, and lemon grass, and is a dominant scent compound in Brassavola nodosa. Nerolidol has a woody, floral, waxy or citrus odor and used in perfumery. It is also used in non-cosmetic products such as detergents and cleansers. It is known for various biological activities include antioxidant, anti fungal, anticancer, and antimicrobial activity. (3R)-(6E)-Nerolidol Nerolidol, (S-(Z))-isomer 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol Nerolidol, (e)-isomer Nerolidol Peruviol Nerolidol, (S-(e))-isomer Nerolidol, (Z)-isomer C15H26O 222.37 222.1984 (3R,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol (3R,6E)-nerolidol 17430-12-5 CC(C)=CCC\C(C)=C\CC[C@@](C)(O)C=C InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+/t15-/m0/s1 FQTLCLSUCSAZDY-GOFCXVBSSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic acyclic compound Farsesane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol nerolidol logp 4.55 ALOGPS logs -4.02 ALOGPS logp 4.31 ChemAxon pka_strongest_acidic 18.46 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (3R,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)=CCC\C(C)=C\CC[C@@](C)(O)C=C ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+/t15-/m0/s1 ChemAxon inchikey FQTLCLSUCSAZDY-GOFCXVBSSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 74.01 ChemAxon polarizability 28.2 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11241545 59959 C19746 C00029339 1.0 2020-03-18 23:28:25 UTC 2020-09-11 20:08:26 UTC CDB000198 (E)-beta-Ocimene (E)-Ocimene or trans-Ocimene, also known as beta-Ocimene, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522). (E)-Ocimene is also considered to be an isoprenoid lipid molecule. (E)-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. (E)-Ocimene exists as a clear, transparent liquid. It is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has a citrus, green woody aroma along with wth a green floral or woody taste. (E)-Ocimene is an approved food additive and is used in perfumery products. (E)-Ocimene occurs naturally in a number of plants and fruits, including basil, coriander, black currants mandarin oranges, kumquats, mangos, mint and oregano. It is also a constituent of the pheromones of several insects including Anastrepha suspensa, Euploea tulliolus koxinga, and Labidus species (CCD). (E)-Ocimene is one of several monoterpenes that are found in cannabis plants (PMID: 6991645). (e)-3,7-Dimethylocta-1,3,6-triene 3,7-Dimethyl-1,3E,6-octatriene trans-3,7-Dimethylocta-1,3,6-triene trans-beta-Ocimene beta-Ocimene trans-b-Ocimene trans-Β-ocimene b-Ocimene Β-ocimene (3E)-3,7-Dimethyl-1,3,6-octatriene (3E)-3,7-Dimethylocta-1,3,6-triene (e)-3,7-Dimethyloctatriene (e)-beta -Ocimene (e)-beta-Ocimene (e)-Ocimene 3,7-Dimethyl-(e)-1,3,6-octatriene 3,7-Dimethyl-(e)-octatriene beta -(e)-Ocimene beta -trans-Ocimene beta-trans-Ocimene e-3,7-Dimethyl-1,3,6-octatriene e-beta-Ocimene trans-3,7-Dimethyl-1,3,6-octatriene trans-beta -Ocimene trans-Ocimene (e)-b-Ocimene (E)-β-Ocimene (3E)-Ocimene (E)-3,7-Dimethyl-1,3,6-octatriene beta-(E)-Ocimene β-(E)-Ocimene β-trans-Ocimene 3,7-Dimethyl-1,3,6-octatriene C10H16 136.23 136.1252 (3E)-3,7-dimethylocta-1,3,6-triene β-ocimene 27400-72-2 CC(C)=CC\C=C(/C)C=C InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8+ IHPKGUQCSIINRJ-CSKARUKUSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Alkatrienes Branched unsaturated hydrocarbons Unsaturated aliphatic hydrocarbons Acyclic monoterpenoid Acyclic olefin Aliphatic acyclic compound Alkatriene Branched unsaturated hydrocarbon Hydrocarbon Olefin Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes monoterpene logp 4.30 ALOGPS logs -2.91 ALOGPS logp 3.48 ChemAxon iupac (3E)-3,7-dimethylocta-1,3,6-triene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)=CC\C=C(/C)C=C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8+ ChemAxon inchikey IHPKGUQCSIINRJ-CSKARUKUSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 49.45 ChemAxon polarizability 17.22 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001465 4444881 5281553 C09873 64280 C00029335 CPD-4889 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:27 UTC 2020-09-11 20:08:26 UTC CDB000199 alpha-Phellandrene alpha-Phellandrene, also known as menthadiene, is one of two known Phellandrene isomers, Œ±- and Œ≤-, which are double-bonded. In Œ±-phellandrene, both double bonds are endocyclic and in Œ≤-phellandrene, one of them is exocyclic. alpha-Phellandrene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Phellandrene is possibly neutral, insoluble in water, but miscible with ether. alpha-Phellandrene has a mint, spice, and turpentine taste. alpha-Phellandrene is found in highest concentrations in anises, common sages, and ceylon cinnamons and in lower concentrations in peppermints. alpha-Phellandrene has also been detected in dills, fennels, sweet basils, and tarragons. This could make alpha-phellandrene a potential biomarker for the consumption of these foods. The phellandrenes are used in fragrances because of their pleasing aromas. alpha-Phellandrene is one of the monoterpenes found in Cannabis (PMID:6991645), (4S)-p-Mentha-1(6),2-diene (5S)-5-Isopropyl-2-methylcyclohexa-1,3-diene (S)-(+)-alpha-Phellandrene (S)-(+)-a-Phellandrene (S)-(+)-Α-phellandrene (S)-a-Phellandrene (S)-Α-phellandrene (+)-alpha-Phellandrene (4S)-p-Mentha-1,5-diene (5S)-2-Methyl-5-(propan-2-yl)cyclohexa-1,3-diene D-alpha-Phellandrene (+)-a-Phellandrene (+)-Α-phellandrene C10H16 136.23 136.1252 (5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene (+)-α-phellandrene 2243-33-6 CC(C)[C@@H]1CC=C(C)C=C1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1 OGLDWXZKYODSOB-JTQLQIEISA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cyclic monoterpenes Menthane monoterpenoids alpha-phellandrene logp 4.29 ALOGPS logs -3.01 ALOGPS logp 3.21 ChemAxon iupac (5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)[C@@H]1CC=C(C)C=C1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1 ChemAxon inchikey OGLDWXZKYODSOB-JTQLQIEISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.82 ChemAxon polarizability 17.14 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013568 391432 443160 C11391 367 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:29 UTC 2020-08-04 22:28:12 UTC CDB000200 beta-Phellandrene Beta-Phellandrene, also known 2-p-menthadiene, is one of two known Phellandrene isomers, Œ±- and Œ≤-, which are double-bonded. In Œ±-phellandrene, both double bonds are endocyclic and in Œ≤-phellandrene, one of them is exocyclic. It belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Plants biosynthesize phellandrene through geranyl pyrophosphate (GPP) in the mevalonate pathway (MVA, PMID: 17467679). The MVA pathway yields the precursors dimethylallyl pyrophosphate and isopentenyl pyrophosphate which combine to produce GPP. This resultant monoterpene undergoes cyclization to form a menthyl cationic species. A hydride shift then forms an allylic carbocation followed by an elimination reaction that occurs at one of two positions, yielding either alpha-phellandrene or beta-phellandrene. Beta-phellandrene colorless to pale yellow clear liquid with a minty, terpenic odor ( http://www.thegoodscentscompany.com/data/rw1103551.html#tophyp). It is found in allspice and is widely distributed in essential oils from various plant families including Angelica, Eucalyptus, Lavandula, Mentha, Pinus species, water fennel, Canada balsam and Cannibis. It is also used as a perfuming agent or fragrance ingredient in cosmetics. Beta-phellandrene is found in, or is added to many foods including dairy products, confectionery, frozen dairy treats, soups and sauces. Beta-phellandrene is one of the monoterpenes found in cannabis plants (PMID: 6991645). It has also found use as a natural pesticide. It has recently been found to induce DNA damage at high doses (2850 mg/kg) (PMID: 28668705). (+)-p-Mentha-1(7),2-diene (S)-3-Isopropyl-6-methylenecyclohexene (-)-b-Phellandrene (-)-Β-phellandrene (-)-p-Mentha-1(7),2-diene (3R)-3-Isopropyl-6-methylenecyclohexene (4R)-p-Mentha-1(7),2-diene (6R)-3-Methylidene-6-(propan-2-yl)cyclohex-1-ene (R)-3-Isopropyl-6-methylenecyclohexene L-beta-Phellandrene (+)-b-Phellandrene (+)-Β-phellandrene C10H16 136.23 136.1252 (6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene (+)-β-phellandrene 6153-16-8 CC(C)[C@@H]1CCC(=C)C=C1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1 LFJQCDVYDGGFCH-JTQLQIEISA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids beta-phellandrene logp 3.98 ALOGPS logs -3.60 ALOGPS logp 3.26 ChemAxon iupac (6S)-3-methylidene-6-(propan-2-yl)cyclohex-1-ene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)[C@@H]1CCC(=C)C=C1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3/t10-/m0/s1 ChemAxon inchikey LFJQCDVYDGGFCH-JTQLQIEISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.75 ChemAxon polarizability 17.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 390916 FDB021861 442484 53 C09877 C00003052 CPD-8769 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Cheng Z, Jiang J, Yang X, Chu H, Jin M, Li Y, Tao X, Wang S, Huang Y, Shang L, Wu S, Hao W, Wei X: The research of genetic toxicity of beta-phellandrene. Environ Toxicol Pharmacol. 2017 Sep;54:28-33. doi: 10.1016/j.etap.2017.06.011. Epub 2017 Jun 20. 28668705 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 1.0 2020-03-18 23:28:31 UTC 2020-09-11 20:08:27 UTC CDB000201 beta-Pinene Œ≤-Pinene belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ≤-Pinene is a component of essential oils from many plants, including cannabis plants (PMID: 6991645, 26657499). Œ≤-Pinene is an isomer of pinene. There are two known isomers of pinene found in nature: Œ±-pinene and Œ≤-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). Both isomers are used by many insects in their chemical communication system. The two isomers of pinene constitute the major component of turpentine. (1R,5R)-beta-Pinene (1R,5R)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]hept-2-ene (1R,5R)-b-Pinene (1R,5R)-Β-pinene (+)-b-Pinene (+)-Β-pinene C10H16 136.24 136.1252 (1R,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane (+)-β-pinene 19902-08-0 CC1(C)[C@H]2C[C@@H]1C(=C)CC2 InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1 WTARULDDTDQWMU-RKDXNWHRSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Pinane monoterpenoid Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon beta-pinene logp 3.94 ALOGPS logs -3.33 ALOGPS logp 2.86 ChemAxon iupac (1R,5R)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC1(C)[C@H]2C[C@@H]1C(=C)CC2 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1 ChemAxon inchikey WTARULDDTDQWMU-RKDXNWHRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.65 ChemAxon polarizability 17.15 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20244 50026 10290825 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-18 23:28:34 UTC 2020-08-04 22:28:12 UTC CDB000202 alpha-Pinene oxide Alpha-pinene oxide has been exploited as an abundant and a cheap terpene substrate and precursor for the biosynthesis of desirable oxygenated terpene derivatives such as limonen. While these can be produced chemically, biosynthesis of oxygenated terpenes is the more desirable process since it proceeds under mild conditions, it does not generate toxic waste and the products can be labelled as ‚Äònatural‚Äô. Some Pseudomonads utilized alpha-terpene, beta-pinene and alpha-pinene oxide as their sole carbon source, suggesting that they have an active metabolic pathway to use it. Using alpha-pinene oxide as a substrate, resting cells of Pseudomonas fluorescens NCIMB 11671 produced isonovalal (cis-2-methyl-5-isopropylhexa-2,5-dienal), which is a fragrance. Another study demonstrated that alpha-pinene oxide was consumed by both Pseudomonas flueoescens and rhodesiae with P. rhodesiae being more efficient in converting alpha-pinene oxide to isonovalal (doi:10.1111/j.1365-2672.2008.03923.x). The enzyme alpha-pinene lyase metabolizes alpha-pine oxide to (Z)-2-methyl-5-isopropylhexa-2,5-dienal ( alpha-Cedrene (PMID: 3667522). Alpha-pinene oxide can also be metabolized to carveol then carvone, thujune and borneol. Alpha-pinene oxide was quantified in labdanum oil (0.23%) and detected in formosan juniper, lemon balm, lamb's lettuce, calabash nutmeg, ocotea floribunda and pepper (http://www.thegoodscentscompany.com/data/rw1218571.html#tooccur). Alpha-pinene oxide is also found in cannabis (PMID: 6991645). C10H16O 152.24 152.1201 (1R,2S,4R,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^{2,4}]octane (1R,2S,4R,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^{2,4}]octane 38301-46-1 C[C@@]12O[C@@H]1C[C@H]1C[C@@H]2C1(C)C InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3/t6-,7-,8-,10+/m1/s1 NQFUSWIGRKFAHK-DQUBFYRCSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic heteropolycyclic compounds Dialkyl ethers Epoxides Hydrocarbon derivatives Oxacyclic compounds Oxepanes Aliphatic heteropolycyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxepane Oxirane Pinane monoterpenoid logp 2.77 ALOGPS logs -3.25 ALOGPS logp 1.98 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1R,2S,4R,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^{2,4}]octane ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles C[C@@]12O[C@@H]1C[C@H]1C[C@@H]2C1(C)C ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3/t6-,7-,8-,10+/m1/s1 ChemAxon inchikey NQFUSWIGRKFAHK-DQUBFYRCSA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 43.41 ChemAxon polarizability 17.88 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 36690300 Griffiths ET, Harries PC, Jeffcoat R, Trudgill PW: Purification and properties of alpha-pinene oxide lyase from Nocardia sp. strain P18.3. J Bacteriol. 1987 Nov;169(11):4980-3. doi: 10.1128/jb.169.11.4980-4983.1987. 3667522 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:36 UTC 2020-08-04 22:28:12 UTC CDB000203 Rotundifolone Rotundifolone belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Rotundifolone is neutral compound. Rotundifolone has an herbal and minty taste. Rotundifolone is found in highest concentrations in spearmints and cornmints. Rotundifolone has also been detected in herbs and spices. This could make rotundifolone a potential biomarker for the consumption of these foods. Rotundifolone is the major chemical constituent (around 70%) of Mentha crispa essential oil which exibits several biological activities, including antinociceptive, spasmolytic, antimicrobial, larvicidal, trypanocidal, cytotoxic, and antitumoral (PMID: 30057673). C10H14O2 166.22 166.0994 (1R,6R)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one (1R,6R)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one CC(C)=C1CC[C@@]2(C)O[C@H]2C1=O InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3/t9-,10+/m0/s1 AKASWINDKIEEBO-VHSXEESVSA-N logp 1.61 ALOGPS logs -1.27 ALOGPS logp 2.07 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1R,6R)-6-methyl-3-(propan-2-ylidene)-7-oxabicyclo[4.1.0]heptan-2-one ChemAxon average_mass 166.22 ChemAxon mono_mass 166.0994 ChemAxon smiles CC(C)=C1CC[C@@]2(C)O[C@H]2C1=O ChemAxon formula C10H14O2 ChemAxon inchi InChI=1S/C10H14O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h9H,4-5H2,1-3H3/t9-,10+/m0/s1 ChemAxon inchikey AKASWINDKIEEBO-VHSXEESVSA-N ChemAxon polar_surface_area 29.6 ChemAxon refractivity 46.56 ChemAxon polarizability 18.31 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 124301339 Turkez H, Tozlu OO, Lima TC, de Brito AEM, de Sousa DP: A Comparative Evaluation of the Cytotoxic and Antioxidant Activity of Mentha crispa Essential Oil, Its Major Constituent Rotundifolone, and Analogues on Human Glioblastoma. Oxid Med Cell Longev. 2018 Jul 2;2018:2083923. doi: 10.1155/2018/2083923. eCollection 2018. 30057673 1.0 2020-03-18 23:28:38 UTC 2020-08-04 22:28:12 UTC CDB000204 p-Menth-8-en-3-one (-)-trans-Isopulegone or p-Menth-8-en-3-one, also known as isopulegone, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 23746261). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. (-)-trans-Isopulegone is neutral compound. (-)-trans-Isopulegone has been detected in fats and oils making it a potential biomarker for the consumption of these foods. It is found in cannabis plants (PMID:6991645). C10H16O 152.24 152.1201 (2S,5S)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one (2S,5S)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one 29606-79-9 C[C@H]1CC[C@@H](C(C)=C)C(=O)C1 InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1 RMIANEGNSBUGDJ-IUCAKERBSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Cyclic ketones Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Hydrocarbon derivative Ketone Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid logp 2.42 ALOGPS logs -2.45 ALOGPS logp 2.7 ChemAxon pka_strongest_acidic 17.88 ChemAxon pka_strongest_basic -7.5 ChemAxon iupac (2S,5S)-5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles C[C@H]1CC[C@@H](C(C)=C)C(=O)C1 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1 ChemAxon inchikey RMIANEGNSBUGDJ-IUCAKERBSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 46.3 ChemAxon polarizability 18.03 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 44163790 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:40 UTC 2020-07-24 23:30:06 UTC CDB000205 (+)-cis-Sabinol (+)-cis-Sabinol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-cis-sabinol is an isoprenoid lipid molecule. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 23746261). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. (+)-cis-Sabinol is very hydrophobic, practically insoluble in water, and relatively neutral. (+)-cis-Sabinol is found in cannabis plants (PMID:6991645) Artemisia annuaand (https://doi.org/10.1007/s11418-006-0112-9) and in herbal plant Dendranthema indicum (PMID: 29510531). (1S,3R,5S)-Sabinol Sabinol Sabinol, (1alpha,3alpha,5alpha)-isomer Sabinol, (1alpha,3beta,5alpha)-isomer C10H16O 152.23 152.1201 (1S,3R,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol (+)-sabinol 471-16-9 CC(C)[C@@]12C[C@@H]1C(=C)[C@H](O)C2 InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3/t8-,9-,10+/m1/s1 MDFQXBNVOAKNAY-BBBLOLIVSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Thujane monoterpenoid Bicyclic monoterpenoids Cyclic monoterpenes Cyclopropane and cyclobutane monoterpenoids Cyclopropane and cyclobutane monoterpenoids sabinol logp 1.90 ALOGPS logs -1.95 ALOGPS logp 1.63 ChemAxon pka_strongest_acidic 17.87 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac (1S,3R,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol ChemAxon average_mass 152.23 ChemAxon mono_mass 152.1201 ChemAxon smiles CC(C)[C@@]12C[C@@H]1C(=C)[C@H](O)C2 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3/t8-,9-,10+/m1/s1 ChemAxon inchikey MDFQXBNVOAKNAY-BBBLOLIVSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.17 ChemAxon polarizability 18.1 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006162 94147 C00000831 C02213 15387 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Fan S, Chang J, Zong Y, Hu G, Jia J: GC-MS Analysis of the Composition of the Essential Oil from Dendranthema indicum Var. Aromaticum Using Three Extraction Methods and Two Columns. Molecules. 2018 Mar 4;23(3). pii: molecules23030576. doi: 10.3390/molecules23030576. 29510531 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-18 23:28:42 UTC 2020-08-04 22:28:12 UTC CDB000206 alpha-Thujene (-)-3-Thujene, also known as alpha-Thujene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (-)-3-Thujene is possibly neutral. It has a green, herb, and woody taste and contributes pungency to the flavor of some herbs such as summer savory. (-)-3-Thujene is found in highest concentrations in cardamoms, sweet bay, and common sages and in lower concentrations in allspices, dills, and cumins. (-)-3-Thujene has also been detected in caraway, corianders, cornmints, spearmints, and pepper (c. annuum). This could make (-)-3-thujene a potential biomarker for the consumption of these foods. (-)-3-Thujene was isolated from Indian olibanum tree (Boswellia serrata), Eucalyptus species, juniper, and cannabis plants (PMID:6991645). (1R,5S)-5-Isopropyl-2-methylbicyclo[3.1.0]hex-2-ene (-)-a-Thujene (-)-Α-thujene (1R,5R)-(-)-3-Thujene (-)-alpha-Thujene 3-Thujene 2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hex-2-ene (±)-alpha-Thujene (±)-α-Thujene alpha-Thujene 2-Methyl-5-isopropylbicyclo[3.1.0]-2-hexene Origanene C10H16 136.24 136.1252 (1R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene (-)-α-thujene 3917-48-4 CC(C)[C@@]12C[C@@H]1C(C)=CC2 InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3/t9-,10-/m1/s1 KQAZVFVOEIRWHN-NXEZZACHSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Thujane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bicyclic monoterpenoids alpha-thujene logp 4.07 ALOGPS logs -2.92 ALOGPS logp 2.8 ChemAxon iupac (1R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hex-2-ene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)[C@@]12C[C@@H]1C(C)=CC2 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h4,7,9H,5-6H2,1-3H3/t9-,10-/m1/s1 ChemAxon inchikey KQAZVFVOEIRWHN-NXEZZACHSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.72 ChemAxon polarizability 17.32 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 50033 637518 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:44 UTC 2020-09-11 20:08:27 UTC CDB000207 alpha-Terpinene Alpha-Terpinene is one of four isomers of terpinene (the other three being beta terpinene, gamma terpenine, and delta terpinine or terpimolene) that differ in the position of carbon-carbon double bonds. Alpha-Terpinene belongs to the class of organic compounds known as menthane monoterpenes. These are monoterpenes with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Terpinene is a naturally occurring monoterpene found in allspice, cardamom, and marjoram. alpha-Terpinene is a constituent of many essential oils with oil from Litsea ceylanica being is a major source (20%) of it. alpha-Terpinene has been found in Citrus, Eucalyptus and Juniperus species, and cannabis plants (PMID:6991645). Œ±-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of Œ±-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids. 1-Isopropyl-4-methyl-1,3-cyclohexadiene 1-Methyl-4-(1-methylethyl)-1,3-cyclohexadiene p-Mentha-1,3-diene Terpilene a-Terpinene Α-terpinene 1-Isopropyl-4-methyl-cyclohexa-1,3-diene 1-Isopropyl-4-methylcyclohexa-1,3-diene 1-Methyl-4-(propan-2-yl)cyclohexa-1,3-diene 1-Methyl-4-isopropyl-1,3-cyclohexadiene 1-Methyl-4-isopropylcyclohexadiene-1,3 alpha -Terpinene FEMA 3558 1,4-p-Menthadiene beta-Terpinene gamma-Terpinene 4-Isopropyl-1-methyl-1,3-cyclohexadiene alpha-Terpinen α-Terpinen alpha-Terpinene C10H16 136.24 136.1252 1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene terpinene 99-86-5 CC(C)C1=CC=C(C)CC1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3 YHQGMYUVUMAZJR-UHFFFAOYSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids a monoterpenoid monoterpene logp 4.25 melting_point < 25 °C logp 4.51 ALOGPS logs -2.44 ALOGPS logp 3.16 ChemAxon iupac 1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)C1=CC=C(C)CC1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3 ChemAxon inchikey YHQGMYUVUMAZJR-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.55 ChemAxon polarizability 17.59 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB007475 7182 C09898 10334 7462 C00003060 CPD-8735 Terpinene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:47 UTC 2020-09-11 20:08:28 UTC CDB000208 gamma-Terpinene Œ≥-Terpinene belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthanes are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and an isopropyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Œ≥-Terpinene is one of 4 isomeric monoterpenes differing in the positions of their two double bonds (alpha- and beta-terpinene being the others). In gamma-terpinene the double bonds are at the 1- and 4-positions of the p-menthane skeleton. Œ≥-Terpinene has been detected as a volatile component in cannabis plant samples (PMID: 26657499). 1,4-p-Menthadiene 1-Isopropyl-4-methyl-1,4-cyclohexadiene 1-Isopropyl-4-methylcyclohexa-1,4-diene 1-Methyl-4-(1-methylethyl)-1,4-cyclohexadiene 1-Methyl-4-propan-2-ylcyclohexa-1,4-diene 4-Isopropyl-1-methyl-1,4-cyclohexadiene Crithmene Moslene p-Mentha-1,4-diene g-Terpinene Γ-terpinene 1-Methyl-4-(propan-2-yl)cyclohexa-1,4-diene alpha Terpinene gamma Terpinene gamma-Terpinen Terpinene 1-Methyl-4-isopropyl-1,4-cyclohexadiene gamma-Terpinene γ-Terpinen C10H16 136.24 136.1252 1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene α terpinene 99-85-4 CC(C)C1=CCC(C)=CC1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3 YKFLAYDHMOASIY-UHFFFAOYSA-N belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. Branched unsaturated hydrocarbons Organic compounds Hydrocarbons Unsaturated hydrocarbons Branched unsaturated hydrocarbons Aliphatic homomonocyclic compounds Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Olefin Unsaturated aliphatic hydrocarbon Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids a monoterpenoid monoterpene water_solubility 0.00868 mg/mL at 22 °C logp 4.50 LI,J & PERDUE,EM (1995) melting_point -10 °C logp 4.36 ALOGPS logs -2.41 ALOGPS logp 3.16 ChemAxon iupac 1-methyl-4-(propan-2-yl)cyclohexa-1,4-diene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)C1=CCC(C)=CC1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3 ChemAxon inchikey YKFLAYDHMOASIY-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.55 ChemAxon polarizability 17.61 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C09900 7461 FDB015968 7181 10577 C00003061 CPD-8736 Terpinene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-18 23:28:49 UTC 2020-09-11 20:08:28 UTC CDB000209 Terpinolene Terpinolene (TPO), also known as alpha-terpinolene or isoterpinene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, terpinolene is considered to be an isoprenoid lipid molecule. Terpinolene is a very hydrophobic monoterpenoid, practically insoluble in water, and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes in plants is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Terpinolene is one of the constituents of turpentine and an isomer of terpinene. It appears colourless to pale yellow liquid. Alpha-terpinolene has been identified as an abundant monoterpene in the essential oil of Cannabis sativa plants (PMID: 6991645). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Although common in cannabis cultivars, terpinolene is typically found in relatively low amounts. On the other hand, the concentration of terpinolene can be has high as 30% of the essential oil. It is thought that terpinolene offers a mildly sedative effect and can reduce anxiety (PMID: 28826544). In particular, terpinolene is a central nervous system depressant that has been shown to induce drowsiness (PMID: 23339024). Terpinolene has been demonstrated to prevent LDL oxidation and is of potential interest in the treatment of atherogenesis and coronary artery disease (PMID: 28826544). Terpinolene exhibits antifungal and larvicidal properties (PMID: 28826544). Terpinolene is also an effective anti-microbial agent, particularly against E coli and Staphylococcus bacteria (PMID: 16402540). Terpinolene is also employed as a fragrence ingredient in lotions, insect repellents (similar to other terpenes), perfumes, and soaps. Terpinolene is also a constituent of many other essential oils e. g. Citrus, Mentha, Juniperus, Myristica species. Parsnip oil (Pastinaca sativa) in particular, is a major source (40-70%). Terpinolene is a sweet, citrus, and fresh tasting compound. It produces a floral, woody or herbal aroma reminiscent of pine needles. In addition to being found in various plant essential oils, terpinolene is found in a few different foods and spices, such as allspice, apples, sage, rosemary, parsnips, nutmegs, and wild carrots and in a lower concentration in sweet bay, star anises, turmerics, apricots, cumins, evergreen blackberries, red bell peppers, and caraway. 1,4(8)-p-Menthadiene 1-Methyl-4-(1-methylethylidene)-1-cyclohexene 1-Methyl-4-(1-methylethylidene)cyclohexene 4-Isopropylidene-1-methylcyclohexene alpha-Terpinolene Isoterpinene Terpinolen a-Terpinolene Α-terpinolene 1,4(8)-Terpadiene 1-Methyl-4-(1-methylethylidene)-cyclohexene 1-Methyl-4-(1-methylethylidene)cyclohexene, 9ci 1-Methyl-4-(propan-2-ylidene)cyclohexene 1-Methyl-4-isopropylidene-1-cyclohexene 4-Isopropylidene-1-methyl-cyclohexene alpha -Terpinolene Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci) FEMA 3046 p-Mentha-1,4(8)-diene Terpinolene delta-Terpinene δ-Terpinene C10H16 136.24 136.1252 1-methyl-4-(propan-2-ylidene)cyclohex-1-ene terpinolene 69073-38-7 CC(C)=C1CCC(C)=CC1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3 MOYAFQVGZZPNRA-UHFFFAOYSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Menthane monoterpenoids Menthane monoterpenoids a monoterpenoid p-menthadiene water_solubility 0.0095 mg/mL at 23 °C logp 4.47 melting_point < 25 °C logp 3.82 ALOGPS logs -1.99 ALOGPS logp 3.12 ChemAxon iupac 1-methyl-4-(propan-2-ylidene)cyclohex-1-ene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)=C1CCC(C)=CC1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3 ChemAxon inchikey MOYAFQVGZZPNRA-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.29 ChemAxon polarizability 17.76 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015966 10979 C06075 9457 11463 C00000861 CPD-4890 Terpinene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Russo EB, Marcu J: Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads. Adv Pharmacol. 2017;80:67-134. doi: 10.1016/bs.apha.2017.03.004. Epub 2017 Jun 5. 28826544 Ito K, Ito M: The sedative effect of inhaled terpinolene in mice and its structure-activity relationships. J Nat Med. 2013 Oct;67(4):833-7. doi: 10.1007/s11418-012-0732-1. Epub 2013 Jan 22. 23339024 Eftekhar F, Yousefzadi M, Azizian D, Sonboli A, Salehi P: Essential oil composition and antimicrobial activity of Diplotaenia damavandica. Z Naturforsch C J Biosci. 2005 Nov-Dec;60(11-12):821-5. doi: 10.1515/znc-2005-11-1202. 16402540 1.0 2020-03-18 23:28:53 UTC 2020-08-04 22:28:13 UTC CDB000211 Syringin Syringin, also known as eleutheroside B or lilacin, was first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841, where its name likely was derived. It belongs to the class of organic compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Syringin results from the glycosidic bonding of sinapyl alcohol and glucose. Some examples of phenolic structures include lignans and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Syringin is neutral compound. Syringin is a naturally occurring organic compound found in many plants such as Eleutherococcus senticosus (Siberian ginseng), dandelion, coffee and cannabis (PMID:6991645). Syringin has also been detected in caraway, fennels, and lemons ( http://www.thegoodscentscompany.com/data/rw1466551.html#tooccur). Syringin have been reported to have immunomodulatory, anti-inflammatory, antinociceptive and hypoglucemic effects (PMID: 11578112; PMID: 15549657; PMID: 18203055). 4-O-(beta-D-Glucosyl)-trans-4-sinapoyl alcohol beta-Terpineol Eleutheroside b Ligustrin Lilacin MAGNOLENIN a Methoxyconiferine Syrigin Syringenin Syringoside 4-O-(b-D-Glucosyl)-trans-4-sinapoyl alcohol 4-O-(Β-D-glucosyl)-trans-4-sinapoyl alcohol b-Terpineol Β-terpineol Sinapyl alcohol 4-O-glucoside C17H24O9 372.37 372.142 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenoxy}oxane-3,4,5-triol syringin 118-34-3 COC1=CC(\C=C\CO)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1 QJVXKWHHAMZTBY-GCPOEHJPSA-N belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Phenolic glycosides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aromatic heteromonocyclic compounds Acetals Alkyl aryl ethers Anisoles Cinnamyl alcohols Dimethoxybenzenes Hydrocarbon derivatives Monosaccharides O-glycosyl compounds Oxacyclic compounds Oxanes Phenoxy compounds Polyols Primary alcohols Secondary alcohols Styrenes Acetal Alcohol Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Cinnamyl alcohol Dimethoxybenzene Ether Hydrocarbon derivative M-dimethoxybenzene Methoxybenzene Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organoheterocyclic compound Oxacycle Oxane Phenol ether Phenolic glycoside Phenoxy compound Polyol Primary alcohol Secondary alcohol Styrene Sinapate derivatives beta-D-glucoside dimethoxybenzene monosaccharide derivative primary alcohol boiling_point 192 °C Wikipedia logp -0.32 ALOGPS logs -2.02 ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 12.2 ChemAxon pka_strongest_basic -2.5 ChemAxon iupac (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenoxy}oxane-3,4,5-triol ChemAxon average_mass 372.37 ChemAxon mono_mass 372.142 ChemAxon smiles COC1=CC(\C=C\CO)=CC(OC)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ChemAxon formula C17H24O9 ChemAxon inchi InChI=1S/C17H24O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-4,6-7,12-15,17-22H,5,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1 ChemAxon inchikey QJVXKWHHAMZTBY-GCPOEHJPSA-N ChemAxon polar_surface_area 138.07 ChemAxon refractivity 90.24 ChemAxon polarizability 37.45 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB011657 5316860 C01533 9380 C00030167 CPD-63 Syringin Cho JY, Nam KH, Kim AR, Park J, Yoo ES, Baik KU, Yu YH, Park MH: In-vitro and in-vivo immunomodulatory effects of syringin. J Pharm Pharmacol. 2001 Sep;53(9):1287-94. doi: 10.1211/0022357011776577. 11578112 Choi J, Shin KM, Park HJ, Jung HJ, Kim HJ, Lee YS, Rew JH, Lee KT: Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin. Planta Med. 2004 Nov;70(11):1027-32. doi: 10.1055/s-2004-832642. 15549657 Niu HS, Liu IM, Cheng JT, Lin CL, Hsu FL: Hypoglycemic effect of syringin from Eleutherococcus senticosus in streptozotocin-induced diabetic rats. Planta Med. 2008 Feb;74(2):109-13. doi: 10.1055/s-2008-1034275. Epub 2008 Jan 17. 18203055 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-18 23:28:56 UTC 2020-07-31 20:34:08 UTC CDB000212 (E)-Calamene (E)-Calamene, also known as calamenene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (E)-Calamene is possibly neutral. (E)-Calamene is found in highest concentrations in allspices, common oregano, and rosemaries and in lower concentrations in lovages. (E)-Calamene has also been detected in cloves, guava, summer savories, sweet basils, and pepper (spice). This could make (E)-calamene a potential biomarker for the consumption of these foods. Calamene is a metabolite of plant Turnera diffusa (Damiana, Mexican holly, Old Woman's Broom), a small shrub of the family Tuneraceae. T. diffusa is native to both Central and South America and now commercially cultivated in Bolivia and Mexico. Calamene is one of the many sesquiterpenes found in cannabis plants and their essential oils (PMID:6991645). Calamenene (7R,10R)-Calamenene C15H22 202.34 202.1722 (1S,4S)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene (1S,4S)-4-isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene 483-77-2 CC(C)[C@@H]1CC[C@H](C)C2=C1C=C(C)C=C2 InChI=1S/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3/t12-,13-/m0/s1 PGTJIOWQJWHTJJ-STQMWFEESA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aromatic homopolycyclic compounds Aromatic hydrocarbons Polycyclic hydrocarbons Tetralins Unsaturated hydrocarbons Aromatic homopolycyclic compound Aromatic hydrocarbon Benzenoid Cadinane sesquiterpenoid Hydrocarbon Polycyclic hydrocarbon Sesquiterpenoid Tetralin Unsaturated hydrocarbon logp 5.60 ALOGPS logs -6.11 ALOGPS logp 5.24 ChemAxon iupac (1S,4S)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene ChemAxon average_mass 202.34 ChemAxon mono_mass 202.1722 ChemAxon smiles CC(C)[C@@H]1CC[C@H](C)C2=C1C=C(C)C=C2 ChemAxon formula C15H22 ChemAxon inchi InChI=1S/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3/t12-,13-/m0/s1 ChemAxon inchikey PGTJIOWQJWHTJJ-STQMWFEESA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 66.83 ChemAxon polarizability 25.71 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006899 6429077 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:24:49 UTC 2020-07-31 20:34:13 UTC CDB000213 beta-Caryophyllene alcohol beta-Caryophyllene alcohol, also known as caryolan-1-ol or caryophyllenol, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H). beta-Caryophyllene alcohol is a neutral compound. beta-Caryophyllene alcohol is a naturally occurring organic compound derived from Caryophyllene. beta-Caryophyllene alcohol has an earthy, moss, and spicy odor (http://www.thegoodscentscompany.com/data/rw1014751.html#toorgano). beta-Caryophyllene alcohol has been detected in grapefruit juice, black pepper cornmint, and oils from bergamot, hinoki root (2.61%), hinoki wood (1.49%), hop and palmarosa ( http://www.thegoodscentscompany.com/data/rw1014751.html#tooccur). This could make beta-caryophyllene alcohol a potential biomarker for the consumption of these foods. beta-Caryophyllene alcohol was a tertiary alcohol detected in cannabis (PMID: 6991645). C15H26O 222.37 222.1984 (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol 472-97-9 CC1(C)C[C@H]2[C@H]1CC[C@@]1(C)CCC[C@]2(O)C1 InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3/t11-,12+,14-,15+/m1/s1 FUQAYSQLAOJBBC-OSRDXIQISA-N belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Tertiary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Aliphatic homopolycyclic compound Cyclic alcohol Hydrocarbon derivative Tertiary alcohol logp 3.52 ALOGPS logs -4.38 ALOGPS logp 3.43 ChemAxon pka_strongest_basic -0.19 ChemAxon iupac (1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC1(C)C[C@H]2[C@H]1CC[C@@]1(C)CCC[C@]2(O)C1 ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3/t11-,12+,14-,15+/m1/s1 ChemAxon inchikey FUQAYSQLAOJBBC-OSRDXIQISA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 66.5 ChemAxon polarizability 27.39 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:24:54 UTC 2020-07-24 23:30:15 UTC CDB000214 (1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane Caryophyllene oxide belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Caryophyllene oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Caryophyllene oxide is a naturally occurring sesquiterpenederived from Cryophyllene. Caryophyllene oxide is one of the many sesquiterpenes found in cannabis plants and their essential oils (PMID: 6991645). Caryophyllene oxide is one of the major compounds found in the essential oil of Salvia spinosa (63.0%). Salvia spinosa essential oil exhibites antimicrobial, cytotoxicity, antioxidant and enzyme inhibitory activities (https://doi.org/10.1016/j.jff.2015.09.011). Caryophyllene oxide is a volatile compound found in different species of citrus fruits (https://doi.org/10.1016/j.foodchem.2017.03.040). Caryophyllene oxide beta-Caryophyllene oxide (-)-Caryophyllene oxide (-)-Epoxydihydrocaryophyllene (-)-beta-Caryophyllene epoxide (-)-β-Caryophyllene epoxide (-)-beta-Caryophyllene oxide (-)-β-Caryophyllene oxide 4beta,5alpha-Epoxycaryophyllene 4β,5α-Epoxycaryophyllene 6,7-Epoxy-3(15)-caryophyllene Caryophyllene 4beta,5alpha-epoxide Caryophyllene 4β,5α-epoxide Caryophyllene 4beta,5alpha-oxide Caryophyllene 4β,5α-oxide Caryophyllene epoxide trans-Caryophyllene oxide beta-Caryophyllene epoxide β-Caryophyllene epoxide β-Caryophyllene oxide beta-Caryophyllene-4beta,5alpha-epoxide beta-Caryophyllene-4β,5α-epoxide 4,5-Caryophyllene oxide C15H24O 220.36 220.1827 (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane 1139-30-6 C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2 InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1 NVEQFIOZRFFVFW-RGCMKSIDSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic heteropolycyclic compounds Dialkyl ethers Epoxides Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteropolycyclic compound Caryophyllane sesquiterpenoid Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Sesquiterpenoid Caryophyllane sesquiterpenoids epoxide logp 3.49 ALOGPS logs -4.50 ALOGPS logp 3.62 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane ChemAxon average_mass 220.36 ChemAxon mono_mass 220.1827 ChemAxon smiles C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2 ChemAxon formula C15H24O ChemAxon inchi InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1 ChemAxon inchikey NVEQFIOZRFFVFW-RGCMKSIDSA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 66.21 ChemAxon polarizability 26.46 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C16908 1742210 C00012483 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:24:57 UTC 2020-08-04 22:28:13 UTC CDB000215 Cedarwood oil terpenes alpha-Cedrene or Cedrene, also known as Cedarwood oil terpenes, belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Cedarwood oil terpenes is possibly neutral. Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known Cedrene isomers including Œ±- and Œ≤-Cedrene which differ in the position of a double bond. alpha-Cedrene is one of the many sesquiterpenes found in cannabis plants and their essential oils (PMID:6991645). Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclation reactions to yield a diverse number of cyclic arrangements. (-)-alpha-Cedrene (1S,2R,5S,7S)-2,6,6,8-Tetramethyltricyclo[5.3.1.0(1,5)]undec-8-ene [3R-(3alpha,3Abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene (-)-a-Cedrene (-)-Α-cedrene [3R-(3a,3Abeta,7b,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene [3R-(3Α,3abeta,7β,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene a-Cedrene Α-cedrene alpha-Cedrene beta-Cedrene Cedrone Cedrene C15H24 204.35 204.1878 (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene 469-61-4 C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC=C3C InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1 IRAQOCYXUMOFCW-OSFYFWSMSA-N belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Cedrane and isocedrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cedrane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cedrane and isocedrane sesquiterpenoids bridged compound polycyclic olefin sesquiterpene logp 5.18 ALOGPS logs -5.11 ALOGPS logp 4.1 ChemAxon iupac (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC=C3C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1 ChemAxon inchikey IRAQOCYXUMOFCW-OSFYFWSMSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.69 ChemAxon polarizability 25.63 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4936353 FDB003904 10216 6431015 C09630 C00003111 CPD-8776 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:00 UTC 2020-08-04 22:28:13 UTC CDB000216 (-)-gamma-Cadinene gamma-Cadinene or (-)-gamma-Cadinene is formally classified as a cyclic hydrocarbon. The name is derived from the Cade juniper (Juniperus oxycedrus L.) where cadinene isomers were first isolated. There are four known Cadinene isomers: Œ±-, Œ≤-, Œ≥-, and Œ¥-Cadinene. gamma-Cadinene is possibly neutral. Although it is classified as a cyclic hydrocarbon, gamma-Cadinene is biochemically a bicyclic sesquiterpene as it synthesized from isoprene units. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Gamma-Cadinene is one of the many sesquiterpenes found in cannabis plants and their essential oils (PMID:6991645). It is found in allspice fruit, allspice leaf, angelica seed oil, armoise oil from Morocco, ayou wood oil, basil leaf oil, basil oil, carrot seed oil from Spain, cascarilla bark oil, cedrela wood oil, ceylon cinnamon, cinnamon leaf and leaf oil, ceylon citronella oil, sweet orange peel oil, oregano oil from Mexico, oregano plant and shoot and oregano shoot oil ( http://www.thegoodscentscompany.com/data/rw1595501.html#tooccur). gamma-Cadinene g-Cadinene Γ-cadinene (-)-g-Cadinene (-)-Γ-cadinene gamma-Cadinene, (+)-gamma(1)-isomer gamma-Cadinene, (-)-isomer gamma-Cadinene, (+)-isomer 1beta,6alpha,7betaH-Cadina-4,10(15)-diene 1β,6α,7βH-Cadina-4,10(15)-diene 1beta,6alpha,7βH-Cadina-4,10(15)-diene (-)-gamma-Cadinene (±)-Cadina-4,10(15)-diene (±)-gamma-Cadinene (±)-γ-Cadinene gamma-Cardinene γ-Cardinene C15H24 204.36 204.1878 (1R,4aS,8aS)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene gamma-cadinene 39029-41-9 CC(C)[C@H]1CCC(=C)[C@H]2CCC(C)=C[C@H]12 InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m1/s1 WRHGORWNJGOVQY-RBSFLKMASA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cadinane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon cadinene logp 4.48 ALOGPS logs -4.54 ALOGPS logp 4.51 ChemAxon iupac (1R,4aS,8aS)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@H]1CCC(=C)[C@H]2CCC(C)=C[C@H]12 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14-,15-/m1/s1 ChemAxon inchikey WRHGORWNJGOVQY-RBSFLKMASA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.53 ChemAxon polarizability 26.38 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C19738 92313 63203 C00030345 C00036278 CPD-12881 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-19 00:25:06 UTC 2020-09-11 20:08:30 UTC CDB000218 (+)-beta-Selinene Œ≤-Selinene or (+)-Œ≤-Selinene, also known as beta-eudesmene or b-selinene, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. (+)-Œ≤-Selinene is a very hydrophobic molecule, practically insoluble in water, but readily soluble in organic solvents such as methanol and ethanol. The selinenes share the molecular formula C15H24 and they have been isolated from a variety of plant sources. Œ≤-Selinene has been detected in cannabis plants and their essential oils (PMID: 26836472, 26657499). There are four known selinene isomers including Œ±-, Œ≤-, Œ≥-, and Œ¥-Selinene. Œ±-Selinene and Œ≤-selinene are the most common and are two of the principal components of the oil from celery seeds. Œ≥-Selinene and Œ¥-selinene are less common. (4AR,7R,8as)-7-isopropenyl-4a-methyl-1-methylenedecahydronaphthalene [4AR-(4aalpha,7alpha,8abeta)]-decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-naphthalene beta-Eudesmene beta-Selinene [4AR-(4aalpha,7a,8abeta)]-decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-naphthalene [4AR-(4aalpha,7α,8abeta)]-decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-naphthalene b-Eudesmene Β-eudesmene b-Selinene Β-selinene (+)-b-Selinene (+)-Β-selinene beta-Selinene, (4ar-(4aalpha,7beta,8aalpha))-isomer beta-Selinene, ((4aalpha,7alpha,8abeta)-(+-))-isomer beta-Selinene, (4as-(4aalpha,7beta,8abeta))-isomer (+)-beta-Selinene Eudesma-4(14),11-diene Selina-4(14),11-diene C15H24 204.36 204.1878 (4aR,7R,8aS)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-decahydronaphthalene β-selinene 17066-67-0 CC(=C)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1 InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15-/m1/s1 YOVSPTNQHMDJAG-QLFBSQMISA-N belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bisabolanes Eudesmane sesquiterpenoids Eudesmane sesquiterpenoids Gymnomitrane sesquiterpenoids beta-selinene logp 5.26 ALOGPS logs -4.79 ALOGPS logp 4.58 ChemAxon iupac (4aR,7R,8aS)-4a-methyl-1-methylidene-7-(prop-1-en-2-yl)-decahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(=C)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15-/m1/s1 ChemAxon inchikey YOVSPTNQHMDJAG-QLFBSQMISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 66.38 ChemAxon polarizability 26.03 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 442393 C09723 10443 C00003186 Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. 26836472 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. 31816756 1.0 2020-03-19 00:25:10 UTC 2020-08-04 22:28:13 UTC CDB000219 3,7(11)-Eudesmadiene 3,7(11)-Eudesmadiene belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. 3,7(11)-Eudesmadiene has been reported with the highest concentration within gingers. 3,7(11)-Eudesmadiene has also been detected, but not quantified, in alcoholic beverages and fats and oils. Eudesma-3,7(11)- diene has also been reported as a component of cannabis plants (PMID: 26657499). C15H24 204.36 204.1878 (4aR,8aS)-4a,8-dimethyl-2-(propan-2-ylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (4aR,8aS)-1,4a-dimethyl-7-(propan-2-ylidene)-3,4,5,6,8,8a-hexahydronaphthalene 6813-21-4 CC(C)=C1CC[C@@]2(C)CCC=C(C)[C@H]2C1 InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,14H,5,7-10H2,1-4H3/t14-,15-/m1/s1 WNRBYZQFEBIUGD-HUUCEWRRSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.78 ALOGPS logs -3.84 ALOGPS logp 4.42 ChemAxon iupac (4aR,8aS)-4a,8-dimethyl-2-(propan-2-ylidene)-1,2,3,4,4a,5,6,8a-octahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=C1CC[C@@]2(C)CCC=C(C)[C@H]2C1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,14H,5,7-10H2,1-4H3/t14-,15-/m1/s1 ChemAxon inchikey WNRBYZQFEBIUGD-HUUCEWRRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.26 ChemAxon polarizability 26.13 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12442774 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:25:14 UTC 2020-08-04 22:28:13 UTC CDB000220 4a-Methyl-1-methylidene-7-(propan-2-ylidene)-decahydronaphthalene Œ≥-Selinene belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ≥-Selinene is a woody tasting compound. It can found in the higher yields within a few different foods, such as gingers, limes, and mandarin orange (clementine, tangerine). Œ≥-Selinene has also been detected, but not quantified, in a few different foods, such as alcoholic beverages, fats and oils, and wild celeries. The selinenes have been identified in a variety of plant sources, including Cannabis sativa (PMID: 26657499). There are four known selinene isomers, namely Œ±-, Œ≤-, Œ≥-, and Œ¥-selinene. Œ±-Selinene and Œ≤-selinene are the most common and are two of the principal components of the oil from celery seeds. Œ≥-Selinene and Œ¥-selinene are less common. C15H24 204.36 204.1878 (4aR,8aR)-4a-methyl-1-methylidene-7-(propan-2-ylidene)-decahydronaphthalene (4aR,8aR)-4a-methyl-1-methylidene-7-(propan-2-ylidene)-hexahydro-2H-naphthalene 515-17-3 CC(C)=C1CC[C@@]2(C)CCCC(=C)[C@H]2C1 InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h14H,3,5-10H2,1-2,4H3/t14-,15-/m1/s1 RMZHSBMIZBMVMN-HUUCEWRRSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.27 ALOGPS logs -4.09 ALOGPS logp 4.48 ChemAxon iupac (4aR,8aR)-4a-methyl-1-methylidene-7-(propan-2-ylidene)-decahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=C1CC[C@@]2(C)CCCC(=C)[C@H]2C1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h14H,3,5-10H2,1-2,4H3/t14-,15-/m1/s1 ChemAxon inchikey RMZHSBMIZBMVMN-HUUCEWRRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.19 ChemAxon polarizability 25.83 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:25:17 UTC 2020-07-24 23:30:19 UTC CDB000221 Friedelanol Friedelanol belongs to the class of organic compounds known as triterpenoids. Friedelanol is biochemically a triterpenoid and it is one of two triterpenes found in cannabis plants (PMID:6991645). Triterpenoids are molecules that contain 30 carbon atoms and are comprised of six isoprene units. Triterpenes are the most diverse class of secondary metabolites and can be found in all living organisms. The biosynthesis of triterpenes occurs through the mevalonic acid pathway (MVA), mainly in the cytosol. A key intermediate in the biosynthesis of triterpenoids is 2,3-oxidosqualene, which undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. C30H52O 428.75 428.4018 (3R,4R,4aS,6aR,6bS,8aS,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-ol (3R,4R,4aS,6aR,6bS,8aS,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-hexadecahydropicen-3-ol 5085-72-3 C[C@H]1[C@H](O)CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@@]3(C)CC[C@@]12C InChI=1S/C30H52O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21+,22+,23+,24+,26-,27+,28-,29-,30-/m0/s1 XCDQFROEGGNAER-OUJFBGHFSA-N logp 6.38 ALOGPS logs -7.02 ALOGPS logp 7.73 ChemAxon pka_strongest_acidic 19.22 ChemAxon pka_strongest_basic -0.96 ChemAxon iupac (3R,4R,4aS,6aR,6bS,8aS,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethyl-docosahydropicen-3-ol ChemAxon average_mass 428.75 ChemAxon mono_mass 428.4018 ChemAxon smiles C[C@H]1[C@H](O)CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@@]3(C)CC[C@@]12C ChemAxon formula C30H52O ChemAxon inchi InChI=1S/C30H52O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21+,22+,23+,24+,26-,27+,28-,29-,30-/m0/s1 ChemAxon inchikey XCDQFROEGGNAER-OUJFBGHFSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 131.13 ChemAxon polarizability 54.03 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:19 UTC 2020-07-24 23:30:06 UTC CDB000222 Blumenol a Blumenol A, also known as vomifoliol, is formally classified as a cyclic ketone although it is biochemically a terpenoid, as it is biosynthesized via isoprene units. Vomifoliol is structurally related to abscisic acid (ABA) but lacks the 2,4-pentadiene side chain. Vomifoliol is a naturally occurring organic compound found in a number of plants, including cannabis (PMID: 6991645) and kidney beans (https://doi.org/10.1246/cl.1973.245). Vomifoliol is a fruity tasting compound also found in common grape. It was first isolated from the leaves and stems of Dutch-grown hemp and identified as a cannabis constituent in 1976 (PMID: 6991645). In one particular study, Vomifoliol exhibited stomatal closure activity in plant epidermal strips (https://doi.org/10.1007/BF00385281). (4S)-4-Hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one (6S,9R)-6-Hydroxy-3-oxo-alpha-ionol Blumenol a Vomifoliol (6S,9R)-6-Hydroxy-3-oxo-a-ionol (6S,9R)-6-Hydroxy-3-oxo-α-ionol C13H20O3 224.3 224.1412 (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one (6S,9R)-vomifoliol 23526-45-6 C[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1 KPQMCAKZRXOZLB-KOIHBYQTSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Cyclohexenones Hydrocarbon derivatives Organic oxides Secondary alcohols Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Cyclofarsesane sesquiterpenoid Cyclohexenone Hydrocarbon derivative Ionone derivative Ketone Megastigmane sesquiterpenoid Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Sesquiterpenoid Tertiary alcohol (6S)-vomifoliol logp 1.24 ALOGPS logs -1.97 ALOGPS logp 1.42 ChemAxon pka_strongest_acidic 13.4 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one ChemAxon average_mass 224.3 ChemAxon mono_mass 224.1412 ChemAxon smiles C[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C ChemAxon formula C13H20O3 ChemAxon inchi InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1 ChemAxon inchikey KPQMCAKZRXOZLB-KOIHBYQTSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 64.93 ChemAxon polarizability 24.63 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01760 5280462 49164 --6-HYDROXY-3-OXO-ALPHA-IONOL C00029834 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:22 UTC 2020-08-04 22:28:13 UTC CDB000223 O-Methyleugenol Methyleugenol, also known as 4-allylveratrole, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying two methoxy groups. Methyleugenol is a sweet, anise, and apricot tasting compound. Outside of the human body, Methyleugenol is found in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified, in several different foods, such as soybeans, evergreen blackberries, muskmelons, citrus, and pomes. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and it is important in the plant-insect interaction and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol has been identified in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance. Methyleugenol has also been identified in cannabis plants (PMID: 6991645). 1,2-Dimethoxy-4-(2-propenyl)benzene Eugenol methyl ether Methyl eugenol O-Methyleugenol 1, 2-Dimethoxy-4-(2-propenyl)benzene 1-(3, 4-Dimethoxyphenyl)-2-propene 4-Allyl-1, 2-dimethoxybenzene 4-Allyl-1,2-dimethoxy-benzene 4-Allyl-1,2-dimethyoxybenzene 4-Allylveratrole Allyl-1,2-dimethoxybenzene Benzene, 4-(2-propenyl)-1,2-dimethoxy Eugenol methyl FEMA 2475 Methyleugenol 4-Allyl-1,2-dimethoxybenzene 1-Allyl-3,4-dimethoxybenzene 1,2-Dimethoxy-4-(2-propen-1-yl)benzene 1,2-Dimethoxy-4-allylbenzene 1,3,4-Eugenol methyl ether 1-(3,4-Dimethoxyphenyl)-2-propene 3,4-Dimethoxy-1-(2-propenyl)benzene 3,4-Dimethoxyallylbenzene 3-(3,4-Dimethoxyphenyl)-1-propene 3-(3,4-Dimethoxyphenyl)propene Chavibetol methyl ether Eugenyl methyl ether Methyl eugenol ether Methyl eugenyl ether Methylchavibetol Veratrole methyl ether C11H14O2 178.23 178.0994 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene methyl eugenol 93-15-2 COC1=C(OC)C=C(CC=C)C=C1 InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 ZYEMGPIYFIJGTP-UHFFFAOYSA-N belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. Dimethoxybenzenes Organic compounds Benzenoids Benzene and substituted derivatives Methoxybenzenes Aromatic homomonocyclic compounds Alkyl aryl ethers Anisoles Hydrocarbon derivatives Phenoxy compounds Alkyl aryl ether Anisole Aromatic homomonocyclic compound Dimethoxybenzene Ether Hydrocarbon derivative O-dimethoxybenzene Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound a small molecule phenylpropanoid water_solubility 0.5 mg/mL at 25 °C melting_point -4 °C logp 2.99 ALOGPS logs -2.98 ALOGPS logp 2.76 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene ChemAxon average_mass 178.23 ChemAxon mono_mass 178.0994 ChemAxon smiles COC1=C(OC)C=C(CC=C)C=C1 ChemAxon formula C11H14O2 ChemAxon inchi InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 ChemAxon inchikey ZYEMGPIYFIJGTP-UHFFFAOYSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 53.27 ChemAxon polarizability 19.89 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008548 21106140 7127 4918 C10454 CPD-6482 C00002741 Methyl eugenol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:24 UTC 2020-07-24 23:30:15 UTC CDB000224 Phylloquinone Phylloquinone or Phytonadione is often called vitamin K1. Vitamin K1 is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K is a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and synthetic naphthoquinone provitamins, and vitamin K3 (menadione) (PMID: 27337968). Vitamin K1 has only one double bond on the proximal isoprene unit. It possesses the same type and degree of activity as does naturally occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Rich sources of vitamin K1 include green plants, algae, and photosynthetic bacteria. Vitamin K1 has antihemorrhagic and prothrombogenic activity. Vitamin K1 is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. Phylloquinone is also an antidote for coumatetralyl. As in many plants, vitamin K is also found in Cannabis sativa (PMID: 6991645). C31H46O2 450.71 450.3498 2-methyl-3-[(2E,7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione 2-methyl-3-[(2E,7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione 79082-97-6 CC(C)CCC[C@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=O InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24+/m0/s1 MBWXNTAXLNYFJB-UDCSOKOMSA-N belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. Vitamin K compounds Organic compounds Lipids and lipid-like molecules Prenol lipids Quinone and hydroquinone lipids Aromatic homopolycyclic compounds Aryl ketones Diterpenoids Hydrocarbon derivatives Naphthoquinones Organic oxides Quinones Aromatic homopolycyclic compound Aryl ketone Benzenoid Diterpenoid Hydrocarbon derivative Ketone Naphthalene Naphthoquinone Organic oxide Organic oxygen compound Organooxygen compound Quinone logp 8.48 ALOGPS logs -6.88 ALOGPS logp 9.7 ChemAxon pka_strongest_basic -7.2 ChemAxon iupac 2-methyl-3-[(2E,7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione ChemAxon average_mass 450.71 ChemAxon mono_mass 450.3498 ChemAxon smiles CC(C)CCC[C@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=O ChemAxon formula C31H46O2 ChemAxon inchi InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24+/m0/s1 ChemAxon inchikey MBWXNTAXLNYFJB-UDCSOKOMSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 142.96 ChemAxon polarizability 56.78 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7048754 Basset GJ, Latimer S, Fatihi A, Soubeyrand E, Block A: Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions. Mini Rev Med Chem. 2017;17(12):1028-1038. doi: 10.2174/1389557516666160623082714. 27337968 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:28 UTC 2020-08-04 22:28:13 UTC CDB000225 (+)-lariciresinol (+)-Lariciresinol belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at positons 2, 3 and 4, respectively. (+)-Lariciresinol has been detected in several different foods, such as parsnips, white mustards, narrowleaf cattails, turnips, and common sages. This could make (+)-Lariciresinol a potential biomarker for the consumption of these foods. Lariciresinol is also found in sesame seeds, Brassica vegetables, in the bark and wood of white fir (Abies alba) and in Cannabis sativa plants (PMID: 26870049). Lariciresinol Larici-resinol Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanol (+)-Lariciresinol C20H24O6 360.4 360.1573 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol lariciresinol 27003-73-2 COC1=C(O)C=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(OC)=C(O)C=C2)=C1 InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1 MHXCIKYXNYCMHY-AUSJPIAWSA-N belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. 7,9'-epoxylignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Tetrahydrofuran lignans Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Dialkyl ethers Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Oxacyclic compounds Phenoxy compounds Primary alcohols Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid 7,9p-epoxylignan Alcohol Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Dialkyl ether Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Primary alcohol Tetrahydrofuran Lignans aromatic ether lignan oxolanes phenols primary alcohol logp 2.16 ALOGPS logs -4.24 ALOGPS logp 2.31 ChemAxon pka_strongest_acidic 9.75 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol ChemAxon average_mass 360.4 ChemAxon mono_mass 360.1573 ChemAxon smiles COC1=C(O)C=CC(C[C@H]2CO[C@@H]([C@H]2CO)C2=CC(OC)=C(O)C=C2)=C1 ChemAxon formula C20H24O6 ChemAxon inchi InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1 ChemAxon inchikey MHXCIKYXNYCMHY-AUSJPIAWSA-N ChemAxon polar_surface_area 88.38 ChemAxon refractivity 97.19 ChemAxon polarizability 38.04 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB030072 C10646 332427 67246 CPD-8907 C00000602 Lariciresinol Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 1.0 2020-03-19 00:25:31 UTC 2020-08-04 22:28:13 UTC CDB000226 (+)-Pinoresinol (+)-Pinoresinol or pinoresinol, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Pinoresinol is a naturally occurring lignan found in several different plant species, such as Styrax sp., Forsythia suspensa and in Cannabis sativa (PMID: 26870049). Pinoresinol is also found in sesame seeds, in brassica vegetables and in olive oil. Pinoresinol, along with other plant lignans, are converted into enterolignans by intestinal microflora in the human body (PMID:15877880). It has also been found in the caterpillar of the cabbage butterfly, Pieris rapae, where it serves as a defence against ants (PMID: 17030818). 4,4'-(1S,3AR,4S,6ar)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2-methoxyphenol) Pinoresinol Pino-resinol (+)-Pinoresinol d-Pinoresinol C20H22O6 358.39 358.1416 4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol pinoresinol 487-36-5 COC1=C(O)C=CC(=C1)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC(OC)=C(O)C=C1 InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1 HGXBRUKMWQGOIE-AFHBHXEDSA-N belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. Furanoid lignans Organic compounds Lignans, neolignans and related compounds Furanoid lignans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Dialkyl ethers Furofuran lignans Furofurans Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Oxacyclic compounds Phenoxy compounds Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Dialkyl ether Ether Furanoid lignan Furofuran Furofuran lignan skeleton Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Tetrahydrofuran Lignans pinoresinol logp 2.31 ALOGPS logs -4.06 ALOGPS logp 2.28 ChemAxon pka_strongest_acidic 9.61 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol ChemAxon average_mass 358.39 ChemAxon mono_mass 358.1416 ChemAxon smiles COC1=C(O)C=CC(=C1)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC(OC)=C(O)C=C1 ChemAxon formula C20H22O6 ChemAxon inchi InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1 ChemAxon inchikey HGXBRUKMWQGOIE-AFHBHXEDSA-N ChemAxon polar_surface_area 77.38 ChemAxon refractivity 95.1 ChemAxon polarizability 36.99 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 66116 73399 40 C05366 C00007190 CPD-8905 Pinoresinol Milder IE, Arts IC, van de Putte B, Venema DP, Hollman PC: Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutr. 2005 Mar;93(3):393-402. doi: 10.1079/bjn20051371. 15877880 Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 Schroeder FC, del Campo ML, Grant JB, Weibel DB, Smedley SR, Bolton KL, Meinwald J, Eisner T: Pinoresinol: A lignol of plant origin serving for defense in a caterpillar. Proc Natl Acad Sci U S A. 2006 Oct 17;103(42):15497-501. doi: 10.1073/pnas.0605921103. Epub 2006 Oct 9. 17030818 1.0 2020-03-19 00:25:36 UTC 2020-08-04 22:28:13 UTC CDB000227 l-(+)-Isoleucine betaine L-(+)-isoleucine betaine, also known as Isoleucine betaine, belongs to the class of compounds known as betaines. A betaine is any neutral chemical compound with a positively charged cationic functional group such as a quaternary ammonium cation that bears no hydrogen atom and with a negatively charged functional group such as a carboxylate group that may not be adjacent to the cationic site. Isoleucine betaine can also be classified as a quaternary ammonium salt with three methyl groups and one carboxyl group attached to the nitrogen atom via C-2. Isoleucine betaine is a naturally occurring organic compound first isolated from Cannabis seeds in 1973. The structure of isoleucine betaine was determined by spectroscopic methods and confirmed by synthesis (https://doi.org/10.1016/0031-9422(73)80454-6). Isoleucine betaine was first isolated and identified as a cannabis constituent in 1973 (PMID:6991645). (2R,3S)-3-Methyl-2-(trimethylazaniumyl)pentanoic acid C9H19NO2 173.26 173.1416 (2R,3S)-3-methyl-2-(trimethylazaniumyl)pentanoate (2R,3S)-3-methyl-2-(trimethylammonio)pentanoate CC[C@H](C)[C@H](C([O-])=O)[N+](C)(C)C InChI=1S/C9H19NO2/c1-6-7(2)8(9(11)12)10(3,4)5/h7-8H,6H2,1-5H3/t7-,8+/m0/s1 WEFWRGFGKPRQQC-JGVFFNPUSA-N logp -2.05 ALOGPS logs -3.72 ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 2.69 ChemAxon iupac (2R,3S)-3-methyl-2-(trimethylazaniumyl)pentanoate ChemAxon average_mass 173.26 ChemAxon mono_mass 173.1416 ChemAxon smiles CC[C@H](C)[C@H](C([O-])=O)[N+](C)(C)C ChemAxon formula C9H19NO2 ChemAxon inchi InChI=1S/C9H19NO2/c1-6-7(2)8(9(11)12)10(3,4)5/h7-8H,6H2,1-5H3/t7-,8+/m0/s1 ChemAxon inchikey WEFWRGFGKPRQQC-JGVFFNPUSA-N ChemAxon polar_surface_area 40.13 ChemAxon refractivity 70.91 ChemAxon polarizability 19.56 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:39 UTC 2020-07-31 20:34:16 UTC CDB000228 Neurine  N, N, N-Trimethylethenaminium hydroxide, also known as neurine, is an alkaloid found in egg yolk, brain, bile and in cadavers. It is formed during putrefaction of biological tissues by the dehydration of choline. It is a poisonous, syrupy liquid with a fishy odor. Neurine is a quaternary ammonium salt with three methyl groups and one vinyl group attached to the nitrogen atom. Synthetically, neurine can be prepared by the reaction of acetylene with trimethylamine. Neurine is unstable and decomposes readily to form trimethylamine. Neurine is a quartenary base found in the roots of a Mexican variant of cannabis plants (PMID: 6991645). Ammonium, trimethylvinyl-, hydroxide Ethenaminium, N,N,N-trimethyl-, hydroxide (9ci) N,N,N-Trimethylethenaminium hydroxide Neirin Neirine Neurin Trimethyl vinyl ammonium hydroxide Trimethyl(vinyl)ammonium hydroxide Vinyltrimethylammonium hydroxide Vitaloid C5H13NO 103.16 103.0997 ethenyltrimethylazanium hydroxide ethenyltrimethylazanium hydroxide 463-88-7 [OH-].C[N+](C)(C)C=C InChI=1S/C5H12N.H2O/c1-5-6(2,3)4;/h5H,1H2,2-4H3;1H2/q+1;/p-1 NIPLIJLVGZCKMP-UHFFFAOYSA-M belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Alkaloids and derivatives Organic compounds Alkaloids and derivatives Aliphatic acyclic compounds Allylamines Hydrocarbon derivatives Organic oxides Organic oxoanionic compounds Organic salts Organopnictogen compounds Quaternary ammonium salts Aliphatic acyclic compound Alkaloid or derivatives Allylamine Amine Hydrocarbon derivative Organic hydroxide Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organonitrogen compound Organopnictogen compound Quaternary ammonium salt logp -1.03 ALOGPS logs -1.02 ALOGPS logp -3.5 ChemAxon iupac ethenyltrimethylazanium hydroxide ChemAxon average_mass 103.16 ChemAxon mono_mass 103.0997 ChemAxon smiles [OH-].C[N+](C)(C)C=C ChemAxon formula C5H13NO ChemAxon inchi InChI=1S/C5H12N.H2O/c1-5-6(2,3)4;/h5H,1H2,2-4H3;1H2/q+1;/p-1 ChemAxon inchikey NIPLIJLVGZCKMP-UHFFFAOYSA-M ChemAxon polar_surface_area 0 ChemAxon refractivity 39.59 ChemAxon polarizability 10.9 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10042 FDB003299 Neurine Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:43 UTC 2020-07-24 23:30:06 UTC CDB000229 n-(p-hydroxy-β-phenylethyl)-p-hydroxy-(trans)-cinnamide N-Trans-Coumaroyltyramine or N-(p-Hydroxyphenyl)ethyl p-hydroxycinnamide is also known as paprazine, N-trans-paprazine or trans-N-p-coumaroyl tyramine. It belongs to the class of organic compounds known as coumaric acids and derivatives. It is also classified as a hydroxycoumaric acid. Coumaric acids are aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. There are two isomers of paprazine, N-trans-paprazine and N-cis-paprazine. Paprazine is a neutral, hydrophobic molecule that is largely insoluble in water. Paprazine is one of the compounds that have been identified in hempseed (Cannabis sativa) (https://doi.org/10.1007/978-1-59259-947-9_2). N-trans-Coumaroyltyramine trans-N-Hydroxycinnamoyltyramine N-p-Coumaroyltyramine N-p-trans-Coumaroyltyramine Paprazine 4-Coumaroyltyramine N-(4-Hydroxy-beta-phenethyl)-4-hydroxycinnamide p-Coumaroyltyramine N-(p-Hydroxy-beta-phenethyl)-p-hydroxy-trans-cinnamide N-HBPHTC (2E)-3-(4-Hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate trans-N-p-Coumaroyl tyramine C17H17NO3 283.32 283.1208 (Z,2E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (Z,2E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid 20375-37-5 O\C(\C=C\C1=CC=C(O)C=C1)=N/CCC1=CC=C(O)C=C1 InChI=1S/C17H17NO3/c19-15-6-1-13(2-7-15)5-10-17(21)18-12-11-14-3-8-16(20)9-4-14/h1-10,19-20H,11-12H2,(H,18,21)/b10-5+ RXGUTQNKCXHALN-BJMVGYQFSA-N belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Coumaric acids and derivatives Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Carbonyl compounds Cinnamic acid amides Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Styrenes 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Cinnamic acid amide Coumaric acid or derivatives Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Secondary carboxylic acid amide Styrene hydroxycinnamic acid melting_point 260 - 261 °C logp 2.58 ALOGPS logs -4.26 ALOGPS logp 3.19 ChemAxon pka_strongest_acidic 4.56 ChemAxon pka_strongest_basic 6.52 ChemAxon iupac (Z,2E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid ChemAxon average_mass 283.32 ChemAxon mono_mass 283.1208 ChemAxon smiles O\C(\C=C\C1=CC=C(O)C=C1)=N/CCC1=CC=C(O)C=C1 ChemAxon formula C17H17NO3 ChemAxon inchi InChI=1S/C17H17NO3/c19-15-6-1-13(2-7-15)5-10-17(21)18-12-11-14-3-8-16(20)9-4-14/h1-10,19-20H,11-12H2,(H,18,21)/b10-5+ ChemAxon inchikey RXGUTQNKCXHALN-BJMVGYQFSA-N ChemAxon polar_surface_area 73.05 ChemAxon refractivity 83.63 ChemAxon polarizability 31.67 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4523095 FDB019132 5372945 65665 C00027418 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:46 UTC 2020-08-04 22:28:13 UTC CDB000230 sec-Butylamine sec-Butylamine¬†is an organic chemical compound, specifically a secondary amine, with the formula CH3CH2CH(NH2)CH3. sec-Butylamine belongs to the class of organic compounds known as monoalkylamines. Together with n-butylamine, tert-butylamine, and isobutylamine, sec-butylamine is one of the isomeric amines of butane. The amine function on position two makes sec-butylamine a chiral compound and therefore exists as two enantiomers. sec-Butylamine is a weak basic compound (based on its pKa). It is a colorless to yellow clear liquid, with a strong fishy-ammonia odor. Sec-Butylamine has been used to control fungal infection in crops (PMID: 5464092) and is also industrially used in the production of some pesticides. sec-Butylamine is also an amine that has been detected in cannabis plants (PMID: 6991645). C4H11N 73.14 73.0891 (2R)-butan-2-amine (2R)-butan-2-amine 13250-12-9 CC[C@@H](C)N InChI=1S/C4H11N/c1-3-4(2)5/h4H,3,5H2,1-2H3/t4-/m1/s1 BHRZNVHARXXAHW-SCSAIBSYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine logp 0.79 ALOGPS logs 0.09 ALOGPS logp 0.67 ChemAxon pka_strongest_basic 10.44 ChemAxon iupac (2R)-butan-2-amine ChemAxon average_mass 73.14 ChemAxon mono_mass 73.0891 ChemAxon smiles CC[C@@H](C)N ChemAxon formula C4H11N ChemAxon inchi InChI=1S/C4H11N/c1-3-4(2)5/h4H,3,5H2,1-2H3/t4-/m1/s1 ChemAxon inchikey BHRZNVHARXXAHW-SCSAIBSYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 23.61 ChemAxon polarizability 9.52 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 2724537 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Graham DC, Hamilton GA: Control of potato gangrene and skin spot diseases by fumigation of tubers with sec-butylamine. Nature. 1970 Jul 18;227(5255):297-8. doi: 10.1038/227297a0. 5464092 1.0 2020-03-19 00:25:49 UTC 2020-08-04 22:28:13 UTC CDB000231 Isoamylamine 3-Methyl-1-butylamine, also known as isoamylamine or 3,3-dimethylpropylamine, belongs to the class of organic compounds known as monoalkylamines (specifically, a primary amine). These are organic compounds containing a primary aliphatic amine group. 3-Methyl-1-butylamine is a weak basic compound (based on its pKa). 3-Methyl-1-butylamine is an ammonia and unpleasant tasting compound. It has been detected, but not quantified, in several different foods, such as green vegetables, spinachs, alcoholic beverages, pomes, and french plantains. Isoamylamine is an amine found in Cannabis plants (PMID: 6991645). 1-Amino-3-methylbutane 3,3-Dimethylpropylamine 3-Methylbutanamine gamma-Isoamylamine Isoamylamine Isobutylcarbylamine Isovalerylamine Leucamine Isopentylamine g-Isoamylamine Γ-isoamylamine 1-Aminoisopentane 3,3-Dimethyl-propylamine 3-Methyl-1-butanamine 3-Methyl-1-butanamine, 9ci 3-Methyl-butylamine 3-METHYLBUTAN-1-amine 3-Methylbutylamine FEMA 3219 Isoamylamine, reag Laquo gammaraquo -isoamylamine LEN Monoisoamylamine Monoisopentylamine Isoamylamine hydrochloride Isoamylamine carbonate (1:1) C5H13N 87.16 87.1048 3-methylbutan-1-amine isoamylamine 107-85-7 CC(C)CCN InChI=1S/C5H13N/c1-5(2)3-4-6/h5H,3-4,6H2,1-2H3 BMFVGAAISNGQNM-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine primary aliphatic amine logp 1.15 ALOGPS logs -0.73 ALOGPS logp 0.99 ChemAxon pka_strongest_basic 10.2 ChemAxon iupac 3-methylbutan-1-amine ChemAxon average_mass 87.16 ChemAxon mono_mass 87.1048 ChemAxon smiles CC(C)CCN ChemAxon formula C5H13N ChemAxon inchi InChI=1S/C5H13N/c1-5(2)3-4-6/h5H,3-4,6H2,1-2H3 ChemAxon inchikey BMFVGAAISNGQNM-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 28.34 ChemAxon polarizability 11.48 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008319 7606 7894 C02640 LEN 43689 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:51 UTC 2020-07-24 23:30:06 UTC CDB000232 ethanolamine Ethanolamine, also known as aminoethanol or glycinol, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Ethanolamine is a weak basic compound (based on its pKa). Ethanolamine exists in all living species, ranging from bacteria to humans and it is also present in Cannabis sativa plants (PMID: 6991645). Ethanolamine can be converted into O-phosphoethanolamine through the action of the enzyme choline/ethanolamine kinase. In humans, ethanolamine is involved in phosphatidylcholine biosynthesis. Ethanolamine has been detected in several different foods, such as millets, chickpea, abalones, common salsifies, and oriental wheats. Like other amines, monoethanolamine is a weak base and this property is exploited in its use in gas scrubbing. The ratio of the products can be controlled by the stoichiometry of the reactants. Reacting ethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent EDTA. It is also used in messenger molecules such as palmitoylethanolamide, which has an effect on CB1 receptors. 1-Amino-2-hydroxyethane 2-Amino-1-ethanol 2-Amino-ethanol 2-Aminoethan-1-ol 2-Aminoethyl alcohol 2-Hydroxyethylamine Aethanolamin Aminoethanol beta-Aminoethanol beta-Aminoethyl alcohol beta-Ethanolamine beta-Hydroxyethylamine Colamine ETA Glycinol Hea MEA MONOETHANOLAMINE b-Aminoethanol Β-aminoethanol b-Aminoethyl alcohol Β-aminoethyl alcohol b-Ethanolamine Β-ethanolamine b-Hydroxyethylamine Β-hydroxyethylamine 2-Aminoethanol 2-Ethanolamine 2-Hydroxyethanamine Envision conditioner PDD 9020 Ethylolamine H-Glycinol Monoaethanolamin Olamine 2 Aminoethanol Ethanolamine Kolamin C2H7NO 61.08 61.0528 2-aminoethan-1-ol ethanolamine 9007-33-4 NCCO InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 HZAXFHJVJLSVMW-UHFFFAOYSA-N belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. 1,2-aminoalcohols Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Primary alcohols 1,2-aminoalcohol Alcohol Aliphatic acyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Organopnictogen compound Primary alcohol Primary aliphatic amine Primary amine Biogenic amines a small molecule ethanolamines primary alcohol primary amine water_solubility 1000.0 mg/mL logp -1.31 HANSCH,C ET AL. (1995) melting_point 10.5 °C boiling_point 170 °C Wikipedia logp -1.53 ALOGPS logs 1.14 ALOGPS logp -1.3 ChemAxon pka_strongest_acidic 15.61 ChemAxon pka_strongest_basic 9.55 ChemAxon iupac 2-aminoethan-1-ol ChemAxon average_mass 61.08 ChemAxon mono_mass 61.0528 ChemAxon smiles NCCO ChemAxon formula C2H7NO ChemAxon inchi InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 ChemAxon inchikey HZAXFHJVJLSVMW-UHFFFAOYSA-N ChemAxon polar_surface_area 46.25 ChemAxon refractivity 16.21 ChemAxon polarizability 6.63 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00189 13835336 DB03994 FDB030851 16000 700 C00007279 ETHANOL-AMINE Ethanolamine 34189 3207 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:25:54 UTC 2020-07-24 23:30:06 UTC CDB000233 cannabisativine Cannabisativine belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturations or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the nitrogen atom replacing the oxigen atom of the cyclic ester group) of the naturally occurring macrolides. Cannabisativine is an alkaloid isolated from the roots of Cannabis sativa L. and its structure was established by single crystal X-ray analysis (PMID: 957120). C21H39N3O3 381.56 381.2991 (1S,2R)-1-[(13S,16aS)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptane-1,2-diol cannabisativine 57682-64-1 CCCCC[C@@H](O)[C@@H](O)[C@@H]1C=CC[C@H]2C\C(O)=N/CCCCNCCCN12 InChI=1S/C21H39N3O3/c1-2-3-4-11-19(25)21(27)18-10-7-9-17-16-20(26)23-14-6-5-12-22-13-8-15-24(17)18/h7,10,17-19,21-22,25,27H,2-6,8-9,11-16H2,1H3,(H,23,26)/t17-,18-,19+,21-/m0/s1 KZZKPJBKEJKNAK-HUUJSLGLSA-N belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Macrolactams Organic compounds Phenylpropanoids and polyketides Macrolactams Aliphatic heteropolycyclic compounds 1,2-diols 1,3-aminoalcohols Amino acids and derivatives Azacyclic compounds Carbonyl compounds Dialkylamines Hydrocarbon derivatives Lactams Organic oxides Organopnictogen compounds Secondary alcohols Secondary carboxylic acid amides Trialkylamines 1,2-diol 1,3-aminoalcohol Alcohol Aliphatic heteropolycyclic compound Amine Amino acid or derivatives Azacycle Carbonyl group Carboxamide group Carboxylic acid derivative Hydrocarbon derivative Lactam Macrolactam Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Secondary aliphatic amine Secondary amine Secondary carboxylic acid amide Tertiary aliphatic amine Tertiary amine azamacrocycle keratan 6'-sulfate logp 1.64 ALOGPS logs -3.22 ALOGPS logp -0.55 ChemAxon pka_strongest_acidic 3.69 ChemAxon pka_strongest_basic 10.4 ChemAxon iupac (1S,2R)-1-[(13S,16aS)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptane-1,2-diol ChemAxon average_mass 381.56 ChemAxon mono_mass 381.2991 ChemAxon smiles CCCCC[C@@H](O)[C@@H](O)[C@@H]1C=CC[C@H]2C\C(O)=N/CCCCNCCCN12 ChemAxon formula C21H39N3O3 ChemAxon inchi InChI=1S/C21H39N3O3/c1-2-3-4-11-19(25)21(27)18-10-7-9-17-16-20(26)23-14-6-5-12-22-13-8-15-24(17)18/h7,10,17-19,21-22,25,27H,2-6,8-9,11-16H2,1H3,(H,23,26)/t17-,18-,19+,21-/m0/s1 ChemAxon inchikey KZZKPJBKEJKNAK-HUUJSLGLSA-N ChemAxon polar_surface_area 88.32 ChemAxon refractivity 110.59 ChemAxon polarizability 44.76 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C10576 3361 442846 C00002320 Turner CE, Hsu MH, Knapp JE, Schiff PL Jr, Slatkin DJ: Isolation of cannabisativine, an alkaloid, from Cannabis sativa L. root. J Pharm Sci. 1976 Jul;65(7):1084-5. doi: 10.1002/jps.2600650736. 957120 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Ryz NR, Remillard DJ, Russo EB: Cannabis Roots: A Traditional Therapy with Future Potential for Treating Inflammation and Pain. Cannabis Cannabinoid Res. 2017 Aug 1;2(1):210-216. doi: 10.1089/can.2017.0028. eCollection 2017. 29082318 1.0 2020-03-19 00:25:59 UTC 2020-07-31 20:34:13 UTC CDB000234 Anhydrocannabisativine Anhydrocannabisativine belongs to the class of organic compounds known as macrolactams, it is an alkaloid isolated from Cannabis sativa L. roots and leafs and its structure was established by spectral analysis and semisynthesis (PMID: 619102, PMID: 6991645). Anhydrocannabisativine is the dehydrated form of cannabisativine. The difference in their structures appears on the substituents on C2: anhydrocannabisativine has the alkyl-keto on C2 of the side chain (PMID: 619102). Although the biological activity of anhydrocannabisativine has yet to be investigated, it has been isolated from Cannabis root extracts which have been found to be useful in the treatment of inflammation, joint pain, gout, and other conditions (PMID: 29082318). C21H37N3O2 363.55 363.2886 1-[(13R,16aR)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptan-2-one 1-[(13R,16aR)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptan-2-one CCCCCC(=O)C[C@@H]1C=CC[C@@H]2CC(=O)NCCCCNCCCN12 InChI=1S/C21H37N3O2/c1-2-3-4-11-20(25)16-18-9-7-10-19-17-21(26)23-14-6-5-12-22-13-8-15-24(18)19/h7,9,18-19,22H,2-6,8,10-17H2,1H3,(H,23,26)/t18-,19+/m0/s1 RKTWGMYTKBSCLV-RBUKOAKNSA-N logp 2.92 ALOGPS logs -3.61 ALOGPS logp 0.59 ChemAxon pka_strongest_acidic 3.72 ChemAxon pka_strongest_basic 10.3 ChemAxon iupac 1-[(13R,16aR)-2-hydroxy-1H,4H,5H,6H,7H,8H,9H,10H,11H,13H,16H,16aH-pyrido[2,1-d]1,5,9-triazacyclotridecan-13-yl]heptan-2-one ChemAxon average_mass 363.55 ChemAxon mono_mass 363.2886 ChemAxon smiles CCCCCC(=O)C[C@@H]1C=CC[C@@H]2CC(=O)NCCCCNCCCN12 ChemAxon formula C21H37N3O2 ChemAxon inchi InChI=1S/C21H37N3O2/c1-2-3-4-11-20(25)16-18-9-7-10-19-17-21(26)23-14-6-5-12-22-13-8-15-24(18)19/h7,9,18-19,22H,2-6,8,10-17H2,1H3,(H,23,26)/t18-,19+/m0/s1 ChemAxon inchikey RKTWGMYTKBSCLV-RBUKOAKNSA-N ChemAxon polar_surface_area 64.93 ChemAxon refractivity 108.35 ChemAxon polarizability 42.9 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Elsohly MA, Turner CE, Phoebe CH Jr, Knapp JE, Schiff PL Jr, Slatkin DJ: Anhydrocannabisativine, a new alkaloid from Cannabis sativa L. J Pharm Sci. 1978 Jan;67(1):124. doi: 10.1002/jps.2600670135. 619102 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Ryz NR, Remillard DJ, Russo EB: Cannabis Roots: A Traditional Therapy with Future Potential for Treating Inflammation and Pain. Cannabis Cannabinoid Res. 2017 Aug 1;2(1):210-216. doi: 10.1089/can.2017.0028. eCollection 2017. 29082318 1.0 2020-03-19 00:26:05 UTC 2020-09-11 20:08:57 UTC CDB000235 Aspartic acid Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As such, it is also present in Cannabis sativa (PMID: 6991645). As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong. Aspartic acid is a nonessential amino acid, since it can be made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of the natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles. (S)-2-Aminobutanedioic acid (S)-2-Aminosuccinic acid 2-Aminosuccinic acid Asp ASPARTIC ACID D L-Asparaginsaeure L-Asp (S)-2-Aminobutanedioate (S)-2-Aminosuccinate 2-Aminosuccinate ASPARTate L-Aspartate (+)-Aspartate (+)-Aspartic acid (2S)-Aspartate (2S)-Aspartic acid (L)-Aspartate (L)-Aspartic acid (R)-2-Aminosuccinate (S)-(+)-Aspartate (S)-(+)-Aspartic acid (S)-Amino-butanedioate (S)-Amino-butanedioic acid (S)-Aminobutanedioate (S)-Aminobutanedioic acid (S)-Aspartate (S)-Aspartic acid 2-Amino-3-methylsuccinate 2-Amino-3-methylsuccinic acid alpha-Aminosuccinate alpha-Aminosuccinic acid Aminosuccinate Asparagate Asparagic acid Asparaginate Asparaginic acid Asparatate H-Asp-OH L-(+)-Aspartate L-(+)-Aspartic acid L-Aminosuccinate L-Aminosuccinic acid L-Asparagate L-Asparagic acid L-Asparaginate L-Asparaginic acid (+-)-Aspartic acid (R,S)-Aspartic acid Aspartate, disodium Aspartate, magnesium Aspartate, monopotassium Aspartic acid, dipotassium salt Aspartic acid, hydrobromide Aspartic acid, monopotassium salt Aspartic acid, monosodium salt Aspartic acid, potassium salt L Aspartate MG5Longoral Potassium aspartate Polysuccinimide Ammonium aspartate Aspartate, ammonium Aspartate, calcium Aspartate, monosodium Aspartic acid, calcium salt Aspartic acid, disodium salt Aspartic acid, magnesium (1:1) salt, hydrochloride, trihydrate Dipotassium aspartate Disodium aspartate Hydrochloride, aspartate magnesium Monopotassium aspartate Sodium aspartate Aspartate, dipotassium Aspartic acid, magnesium (2:1) salt Aspartic acid, sodium salt Hydrobromide aspartic acid Magnesium aspartate MG 5 Longoral Monosodium aspartate Aspartate magnesium hydrochloride Aspartate, potassium Aspartate, sodium Aspartic acid, ammonium salt Aspartic acid, hydrochloride Aspartic acid, magnesium-potassium (2:1:2) salt Calcium aspartate Hydrochloride aspartic acid L Aspartic acid Magnesiocard MG-5-Longoral Poly-DL-succinimide C4H7NO4 133.1 133.0375 (2S)-2-aminobutanedioic acid L-aspartic acid 56-84-8 N[C@@H](CC(O)=O)C(O)=O InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 CKLJMWTZIZZHCS-REOHCLBHSA-N belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Aspartic acid and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Aspartic acid or derivatives Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative L-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Amino acids Common amino acids L-alpha-amino acid aspartate family amino acid aspartic acid proteinogenic amino acid water_solubility 5.39 mg/mL YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -3.89 CHMELIK,J ET AL. (1991) melting_point 270 °C logp -3.52 ALOGPS logs 0.03 ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 1.7 ChemAxon pka_strongest_basic 9.61 ChemAxon iupac (2S)-2-aminobutanedioic acid ChemAxon average_mass 133.1 ChemAxon mono_mass 133.0375 ChemAxon smiles N[C@@H](CC(O)=O)C(O)=O ChemAxon formula C4H7NO4 ChemAxon inchi InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 ChemAxon inchikey CKLJMWTZIZZHCS-REOHCLBHSA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 26.53 ChemAxon polarizability 11.28 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00049 FDB012567 DB00128 5960 5745 17053 C00001342 L-ASPARTATE Aspartic acid 33663 5206 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:07 UTC 2020-07-07 15:56:37 UTC CDB000236 galacturonic acid Galacturonic acid, also known as D-galacturonate or sodium pectate, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 position oxidized to a carboxylic acid. Galacturonic acid exists in all living species, ranging from bacteria to humans. Galacturonic acid has been found in higher concentrations in flaxseeds. It has also been detected but not quantified in several different foods, such as common grapes, cocoa beans, roselles, milk (cow), and figs. Galacturonic acid has also been found in Cannabis sativa (PMID: 6991645). (2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoic acid D-Galacturonic acid (2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoate D-Galacturonate Galacturonate DL-Galacturonic acid D-Galactopyranuronic acid Galacturonic acid, (D)-isomer Galacturonic acid, (alpha-D)-isomer Galacturonic acid, calcium, sodium salt, (D)-isomer Galacturonic acid, monosodium salt, (D)-isomer Aldehydo-D-galacturonate Polygalacturonic acid, aluminum salt Sodium pectate Galacturonan Homogalacturonan Pectic acid Polygalacturonic acid homopolymer Polygalacturonic acid, sulfated Calcium polygalacturonate Pectate Polygalacturonic acid Polygalacturonic acid, calcium salt Polygalacturonic acid, homopolymer sodium salt Sodium polygalacturonate Anhydrogalacturonic acid Calcium pectate Polygalacturonic acid, homopolymer (D)-isomer Aldehydo-D-galacturonic acid (DL)-Galacturonic acid (D)-Galacturonic acid Galacturonic acid C6H10O7 194.14 194.0427 (2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid aldehydo-D-galacturonic acid 14982-50-4 O[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1 IAJILQKETJEXLJ-RSJOWCBRSA-N belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucuronic acid derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Alpha-hydroxyaldehydes Beta hydroxy acids and derivatives Beta-hydroxy aldehydes Carboxylic acids Hexoses Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols Alcohol Aldehyde Aliphatic acyclic compound Alpha-hydroxy acid Alpha-hydroxyaldehyde Beta-hydroxy acid Beta-hydroxy aldehyde Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Glucuronic acid or derivatives Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Polyol Secondary alcohol D-galacturonic acid melting_point 159 °C Wikipedia logp -2.32 ALOGPS logs -0.29 ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 3.24 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid ChemAxon average_mass 194.14 ChemAxon mono_mass 194.0427 ChemAxon smiles O[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O ChemAxon formula C6H10O7 ChemAxon inchi InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1 ChemAxon inchikey IAJILQKETJEXLJ-RSJOWCBRSA-N ChemAxon polar_surface_area 135.29 ChemAxon refractivity 37.21 ChemAxon polarizability 16.23 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001160 76444 84740 47962 C08348 C00001120 D-Galacturonic acid 6713 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:12 UTC 2020-08-04 22:28:14 UTC CDB000237 beta-D-Glucose Œ≤-D-Glucopyranose is one of the four cyclic isomers of D-glucose. Glucose (CAS: 50-99-7) is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is the most abundant monosaccharide, a subcategory of carbohydrates and it is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, as such it is also found in Cannabis sativa (PMID: 6991645). In plants and algae, it is used to make cellulose in cell walls, which is the most abundant carbohydrate polymer found in nature. Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals, glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. D-Glucose is found to be associated with 3-methyl-crotonyl-glycinuria, growth hormone deficiency, and primary hypomagnesemia, which are inborn errors of metabolism. Glucose is used therapeutically in fluid and nutrient replacement. Glucose b-D-Glucose β-D-glucose b-D-Glucopyranose b-Dextrose b-Glucose beta-D-Glucopyranose beta-Dextrose beta-Glucose D Glucose Glucose, (beta-D)-isomer Dextrose Glucose, (DL)-isomer D-Glucose D-Glucopyranose D-Glucopyranoside beta-D-Glucopyranoside beta-D-Glucose β-D-Glucopyranose β-D-Glucopyranoside β-D-Glucose β-Dextrose β-Glucose D-GLC D-GLCP GLC-OH C6H12O6 180.16 180.0634 (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol glucoside 108942-17-2 OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1 WQZGKKKJIJFFOK-VFUOTHLCSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol D-glucopyranose water_solubility 1200.0 mg/mL logp -3.24 SANGSTER (1994) melting_point 146 - 150 °C logp -2.57 ALOGPS logs 0.64 ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1 ChemAxon inchikey WQZGKKKJIJFFOK-VFUOTHLCSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.35 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB02379 C00221 58238 64689 FDB011824 15903 GLC C00001122 Glucose Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:15 UTC 2020-08-04 22:28:14 UTC CDB000238 alpha-d-Glucose Œ±-D-Glucopyranose is one of the four cyclic isomers of D-glucose. Glucose (CAS: 50-99-7) is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is the most abundant monosaccharide, a subcategory of carbohydrates and it is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, as such it is also found in Cannabis sativa (PMID: 6991645). In plants and algae, it is used to make cellulose in cell walls, which is the most abundant carbohydrate polymer found in nature. Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals, glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. D-Glucose is found to be associated with 3-methyl-crotonyl-glycinuria, growth hormone deficiency, and primary hypomagnesemia, which are inborn errors of metabolism. Glucose is used therapeutically in fluid and nutrient replacement. alpha-D-GLC alpha-Dextrose a-D-GLC Α-D-GLC a-Dextrose Α-dextrose a-D-Glucose Α-D-glucose a-D-Glucopyranose a-Glucose alpha-D-Glucopyranose alpha-delta-Glucopyranose alpha-delta-Glucose alpha-Glucose Hexopyranose Anhydrous dextrose D Glucose D-Glucose Dextrose Dextrose, anhydrous Glucose Glucose monohydrate Glucose, (DL)-isomer Glucose, (L)-isomer Glucose, (alpha-D)-isomer Glucose, (beta-D)-isomer L Glucose L-Glucose Monohydrate, glucose 1,3-alpha-D-Glucan alpha-1,3-Glucan alpha-D-Glucopyranoside C6H12O6 180.16 180.0634 (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol α-glucose 492-62-6 OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1 WQZGKKKJIJFFOK-DVKNGEFBSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol D-glucopyranose water_solubility 500 mg/mL at 20 °C melting_point 146 °C logp -2.57 ALOGPS logs 0.64 ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol ChemAxon average_mass 180.16 ChemAxon mono_mass 180.0634 ChemAxon smiles OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1 ChemAxon inchikey WQZGKKKJIJFFOK-DVKNGEFBSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 35.92 ChemAxon polarizability 16.09 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00267 FDB011829 71358 79025 17925 C00001122 ALPHA-GLUCOSE 6897 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:19 UTC 2020-06-30 19:05:20 UTC CDB000239 d-manno-heptulose D-Manno-Heptulose, D-manno-2-Heptulose 1,3,4,5,6,7-Hexahydroxyheptan-2-one or Mannoheptulose belongs to the class of organic compounds known as heptoses. Heptoses are monosaccharides with seven carbon atoms in their structure. D-manno-2-heptulose is one of the few naturally occurring heptoses. It has been found primarily in alfalfa, avocados, primrose (PMID: 31293606) and also in cannabis (PMID: 6991645). Though the carbohydrate is thought to be produced during photosynthesis the precise biological pathway for the synthesis of mannoheptulose is still unknown. Like other sugars it is transported in the plant through the phloem. Because of its in vitro inhibition of glycolysis, it has been investigated as a novel nutraceutical for weight management in dogs. However, while it is suggested that mannoheptulose affects the energy balance of adult dogs, research is still inconclusive regarding the significance of the alteration of energy expenditure (PMID: 26479244, PMID: 26656105, PMID: 28444793). alpha-D-Mannoheptulopyranose Mannoheptulose a-D-Mannoheptulopyranose Α-D-mannoheptulopyranose a-D-Manno-heptulopyranose Α-D-manno-heptulopyranose Mannoketoheptose (+)-Mannoheptulose D-Mannoheptulose D-Manno-heptulose alpha-D-Manno-2-heptulopyranose Α-D-manno-2-heptulopyranose C7H14O7 210.18 210.074 (2S,3S,4S,5S,6R)-2,6-bis(hydroxymethyl)oxane-2,3,4,5-tetrol mannoketoheptose 60426-75-7 OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C7H14O7/c8-1-3-4(10)5(11)6(12)7(13,2-9)14-3/h3-6,8-13H,1-2H2/t3-,4-,5+,6+,7+/m1/s1 HAIWUXASLYEWLM-VEIUFWFVSA-N belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. C-glycosyl compounds Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hexoses Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound C-glycosyl compound Hemiacetal Hexose monosaccharide Hydrocarbon derivative Monosaccharide Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol D-manno-heptulose melting_point 151 - 152 °C logp -2.60 ALOGPS logs 0.64 ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 10.28 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3S,4S,5S,6R)-2,6-bis(hydroxymethyl)oxane-2,3,4,5-tetrol ChemAxon average_mass 210.18 ChemAxon mono_mass 210.074 ChemAxon smiles OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C7H14O7 ChemAxon inchi InChI=1S/C7H14O7/c8-1-3-4(10)5(11)6(12)7(13,2-9)14-3/h3-6,8-13H,1-2H2/t3-,4-,5+,6+,7+/m1/s1 ChemAxon inchikey HAIWUXASLYEWLM-VEIUFWFVSA-N ChemAxon polar_surface_area 130.61 ChemAxon refractivity 42.32 ChemAxon polarizability 19.14 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001201 390153 441419 C08236 28657 Pedreschi R, Uarrota V, Fuentealba C, Alvaro JE, Olmedo P, Defilippi BG, Meneses C, Campos-Vargas R: Primary Metabolism in Avocado Fruit. Front Plant Sci. 2019 Jun 26;10:795. doi: 10.3389/fpls.2019.00795. eCollection 2019. 31293606 McKnight LL, Eyre R, Gooding MA, Davenport GM, Shoveller AK: Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs. Animals (Basel). 2015 Jun 16;5(2):442-54. doi: 10.3390/ani5020365. 26479244 McKnight LL, Root-McCaig J, Wright D, Davenport GM, France J, Shoveller AK: Dietary Mannoheptulose Does Not Significantly Alter Daily Energy Expenditure in Adult Labrador Retrievers. PLoS One. 2015 Dec 11;10(12):e0143324. doi: 10.1371/journal.pone.0143324. eCollection 2015. 26656105 McKnight LL, France J, Wright D, Davenport G, Shoveller AK: Dietary mannoheptulose does not alter glucose or lipid metabolism in adult Labrador Retrievers. J Anim Physiol Anim Nutr (Berl). 2018 Feb;102(1):e122-e131. doi: 10.1111/jpn.12713. Epub 2017 Apr 26. 28444793 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:22 UTC 2020-06-30 19:05:20 UTC CDB000240 d-glycero-d-manno-octulose D-glycero-d-manno-octulose belongs to the class of organic compounds known as octoses. These are monosaccharide compounds in which the sugar moiety is an octose. Octoses are monosaccharides with eight carbon atoms in their structure. Though the carbohydrate is thought to be produced during photosynthesis the precise biological pathway for its biosynthesis is still unknown. Like other sugars it is transported in the plant through the phloem. D-glycero-d-manno-octulose has been found in Cannabis plants (PMID: 6991645) as well as in other medical herbs such as alfalfa, Aloe vera and anise. C8H16O8 240.21 240.0845 (3S,4S,5R,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one (3S,4S,5R,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO InChI=1S/C8H16O8/c9-1-3(11)5(13)7(15)8(16)6(14)4(12)2-10/h3,5-11,13-16H,1-2H2/t3-,5-,6-,7-,8-/m1/s1 KSHYQYHHIKNYAY-PNAXYBNRSA-N belongs to the class of organic compounds known as octoses. These are monosaccharide compounds in which the sugar moiety is an octose (8 carbon atoms). Octoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Acyloins Alpha-hydroxy ketones Beta-hydroxy ketones Hydrocarbon derivatives Organic oxides Polyols Primary alcohols Secondary alcohols Acyloin Alcohol Aliphatic acyclic compound Alpha-hydroxy ketone Beta-hydroxy ketone Carbonyl group Hydrocarbon derivative Ketone Octose monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol logp -2.58 ALOGPS logs -0.13 ALOGPS logp -4.5 ChemAxon pka_strongest_acidic 8.97 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3S,4S,5R,6R,7R)-1,3,4,5,6,7,8-heptahydroxyoctan-2-one ChemAxon average_mass 240.21 ChemAxon mono_mass 240.0845 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO ChemAxon formula C8H16O8 ChemAxon inchi InChI=1S/C8H16O8/c9-1-3(11)5(13)7(15)8(16)6(14)4(12)2-10/h3,5-11,13-16H,1-2H2/t3-,5-,6-,7-,8-/m1/s1 ChemAxon inchikey KSHYQYHHIKNYAY-PNAXYBNRSA-N ChemAxon polar_surface_area 158.68 ChemAxon refractivity 49.49 ChemAxon polarizability 21.65 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 102060354 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:27 UTC 2020-08-04 22:28:14 UTC CDB000241 cellulose Cellulose is a polysaccharide and as such, belongs to the class of organic compounds known as O-glycosyl compounds. These are glycosides in which a sugar group is bonded to another sugar group via an O-glycosidic bond. Cellulose is the most abundant organic polymer on earth and therefore also the most common polysaccharide found in Cannabis sativa. As a reference, the cellulose content of cotton fiber is 90%, that of wood is 40‚Äì50%, and that of dried hemp is approximately 57%. The use of cellulose-rich, hemp-derived fibers has gained a lot of interest, especially due to its relative light weight and its reported mechanical and antibacterial properties (PMID: 26870049). 4-O-beta-D-Mannopyranosyl-alpha-D-mannopyranose 4-O-b-D-Mannopyranosyl-a-D-mannopyranose 4-O-Β-D-mannopyranosyl-α-D-mannopyranose a-Mannobiose Α-mannobiose C12H22O11 342.3 342.1162 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol α-mannobiose 9004-34-6 OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9+,10-,11+,12+/m1/s1 GUBGYTABKSRVRQ-TYAPZPMWSA-N belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. O-glycosyl compounds Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Disaccharides Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound Disaccharide Hemiacetal Hydrocarbon derivative O-glycosyl compound Organoheterocyclic compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol mannobiose melting_point 260–270 °C Wikipedia logp -3.01 ALOGPS logs 0.23 ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 11.25 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol ChemAxon average_mass 342.3 ChemAxon mono_mass 342.1162 ChemAxon smiles OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C12H22O11 ChemAxon inchi InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9+,10-,11+,12+/m1/s1 ChemAxon inchikey GUBGYTABKSRVRQ-TYAPZPMWSA-N ChemAxon polar_surface_area 189.53 ChemAxon refractivity 68.34 ChemAxon polarizability 31.32 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 36224 5288769 Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 1.0 2020-03-19 00:26:34 UTC 2020-06-30 19:05:20 UTC CDB000243 d -bornesitol D-Bornesitol or bornesitol is the methyl ether dervative of myo-Inositol. Myo-Inositol is a cyclitol and an inositol isoform. Inositol is a derivative of cyclohexane with six hydroxyl groups, making it a polyol. It is also known as a sugar alcohol, having exactly the same molecular formula as glucose or other hexoses. Inositol exists in nine possible stereoisomers, including scyllo-inositol, myo-inositol (the most abundant), muco-inositol, D-chiro-inositol, L-chiro-inositol, neo-inositol, allo-inositol, epi-inositol and cis-inositol. In humans, most inositol is synthesized in the kidneys, typically in amounts of a few grams per day. Levoinositol is found in dandelion and is widely distributed in higher plants predominantly as its monomethyl ether. Inositol is a cyclic polyalcohol that plays an important role as a second messenger in the cells, in the form of inositol phosphates. It is found in many foods, particularly in cereals with high bran content. It is an isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in humans. Inositol phospholipids are important in signal transduction. Inositol is one of the sugar alcohols and cyclitols identified in Cannabis sativa plants (PMID: 6991645). (1R,2R,3S,4S,5R,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol 1-O-Methyl-myo-inositol Bornesitol D-(-)-Bornesitol 1D-1-O-Methyl-myo-inositol D-1-O-Methyl-myo-inositol D-Bornesitol (-)-Bornesitol C7H14O6 194.18 194.079 (1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol (-)-bornesitol 484-71-9 CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4+,5-,6-,7-/m1/s1 DSCFFEYYQKSRSV-AGZHHQKVSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Dialkyl ethers Hydrocarbon derivatives Polyols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl ether Ether Hydrocarbon derivative Polyol methyl myo-inositols logp -2.67 ALOGPS logs 0.45 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 12.36 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1R,2R,3S,4S,5R,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol ChemAxon average_mass 194.18 ChemAxon mono_mass 194.079 ChemAxon smiles CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O ChemAxon formula C7H14O6 ChemAxon inchi InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4+,5-,6-,7-/m1/s1 ChemAxon inchikey DSCFFEYYQKSRSV-AGZHHQKVSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 40.53 ChemAxon polarizability 18.18 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004281 10254649 C03659 18427 1-METHYL-MYO-INOSITOL C00048928 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:36 UTC 2020-07-31 20:34:14 UTC CDB000244 L-Quebrachitol L-Quebrachitol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. L-Quebrachitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, L-Quebrachitol is found, on average, in the highest concentration within sea-buckthornberries. L-Quebrachitol has also been detected, but not quantified in, mugworts. This could make L-quebrachitol a potential biomarker for the consumption of these foods. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made. It shows a sweetening property half of that of sucrose but induces colic or diarrhoea at concentration used to render the food palatable. Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It was first isolated by Tanret in 1887 from the bark of Aspidosperma quebracho. The substance was tested as a sweetening agent for diabetics in 1933. Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. (-)-Quebrachitol 1l-2-O-Methyl-chiro-inositol 2-O-Methyl-L-chiro-inositol Quebrachitol C7H14O6 194.18 194.079 (1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentol (-)-quebrachitol 642-38-6 CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1 DSCFFEYYQKSRSV-FIZWYUIZSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Dialkyl ethers Hydrocarbon derivatives Polyols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl ether Ether Hydrocarbon derivative Polyol cyclitol melting_point 191 °C logp -2.67 ALOGPS logs 0.45 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 12.36 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentol ChemAxon average_mass 194.18 ChemAxon mono_mass 194.079 ChemAxon smiles CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O ChemAxon formula C7H14O6 ChemAxon inchi InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1 ChemAxon inchikey DSCFFEYYQKSRSV-FIZWYUIZSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 40.53 ChemAxon polarizability 17.96 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012526 10254652 C08257 111 C00001169 Quebrachitol 1.0 2020-03-19 00:26:41 UTC 2020-08-04 22:28:14 UTC CDB000245 3,6-Dimethyl-tridecane 3,6-dimethyl-tridecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. 3,6-dimethyl-tridecane is possibly neutral. 3,6-dimethyl-tridecane is a dimethylated derivative of tridecane. The name ‚Äútridecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C13H28, or to a mixture of them. This chemical formula allows for the existence of 802 constitutional isomers. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-tridecane, with a straight-chain CH3(CH2)11CH3. Tridecanes are combustible colourless liquids. They have no specific industrial value other than being a part of fuels and solvents. 3,6-dimethyl-tridecane is one of the abundant alkanes identified in Cannabis sativa (PMID: 6991645). C15H32 212.42 212.2504 (3S,6S)-3,6-dimethyltridecane (3S,6S)-3,6-dimethyltridecane CCCCCCC[C@H](C)CC[C@@H](C)CC InChI=1S/C15H32/c1-5-7-8-9-10-11-15(4)13-12-14(3)6-2/h14-15H,5-13H2,1-4H3/t14-,15-/m0/s1 CZZOBJTWKAKCID-GJZGRUSLSA-N logp 8.09 ALOGPS logs -6.81 ALOGPS logp 6.82 ChemAxon iupac (3S,6S)-3,6-dimethyltridecane ChemAxon average_mass 212.42 ChemAxon mono_mass 212.2504 ChemAxon smiles CCCCCCC[C@H](C)CC[C@@H](C)CC ChemAxon formula C15H32 ChemAxon inchi InChI=1S/C15H32/c1-5-7-8-9-10-11-15(4)13-12-14(3)6-2/h14-15H,5-13H2,1-4H3/t14-,15-/m0/s1 ChemAxon inchikey CZZOBJTWKAKCID-GJZGRUSLSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 70.71 ChemAxon polarizability 30.34 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:43 UTC 2020-08-04 22:28:14 UTC CDB000246 2,6-Dimethyl-tetradecane 2,6-dimethyl-tetradecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. 2,6-dimethyl-tetradecane is possibly neutral. 2,6-dimethyl-tetradecane is a dimethylated derivative of tetradecane. The name ‚Äútetradecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C14H30, or to a mixture of them. This chemical formula allows for the existence of 1858 constitutional isomers. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-tetradecane, with a straight-chain CH3(CH2)12CH3. Tetradecanes are combustible colourless liquids. They have no specific industrial value other than being a part of fuels and solvents. 2,6-dimethyl-tetradecane is one of the alkanes identified in Cannabis sativa (PMID: 6991645). C16H34 226.45 226.2661 (6R)-2,6-dimethyltetradecane (6R)-2,6-dimethyltetradecane CCCCCCCC[C@@H](C)CCCC(C)C InChI=1S/C16H34/c1-5-6-7-8-9-10-13-16(4)14-11-12-15(2)3/h15-16H,5-14H2,1-4H3/t16-/m1/s1 CHTMNBGVYWZUQQ-MRXNPFEDSA-N belongs to the class of organic compounds known as saturated hydrocarbons. These are hydrocarbons that contains only saturated carbon atoms, which are linked to one another through single bonds. These includes alkanes and cycloalkanes. Saturated hydrocarbons Organic compounds Hydrocarbons Saturated hydrocarbons Aliphatic acyclic compounds Aliphatic acyclic compound Saturated hydrocarbon logp 8.45 ALOGPS logs -7.04 ALOGPS logp 7.26 ChemAxon iupac (6R)-2,6-dimethyltetradecane ChemAxon average_mass 226.45 ChemAxon mono_mass 226.2661 ChemAxon smiles CCCCCCCC[C@@H](C)CCCC(C)C ChemAxon formula C16H34 ChemAxon inchi InChI=1S/C16H34/c1-5-6-7-8-9-10-13-16(4)14-11-12-15(2)3/h15-16H,5-14H2,1-4H3/t16-/m1/s1 ChemAxon inchikey CHTMNBGVYWZUQQ-MRXNPFEDSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 75.31 ChemAxon polarizability 32.51 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 102188589 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:47 UTC 2020-08-04 22:28:14 UTC CDB000247 2,6-Dimethyl-hexadecane 2,6-dimethyl-hexadecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. 2,6-dimethyl-hexadecane is possibly neutral. 2,6-dimethyl-hexadecane is a dimethylated derivative of hexadecane, also known as cetane. The name ‚Äúhexadecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C16H34, or to a mixture of them. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-tetradecane, with a straight-chain CH3(CH2)14CH3. Hexadecane is considered to be a hydrocarbon lipid molecule. Hexadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hexadecane is a fuel/ diesel tasting compound. Outside of the human body, hexadecane is found in black walnuts, among other natural sources. Hexadecanes are combustible colourless liquids. They have no specific industrial value other than being a part of fuels and solvents. 2,6-dimethyl-hexadecane is one of the alkanes identified in Cannabis sativa (PMID: 6991645). C18H38 254.5 254.2974 (6R)-2,6-dimethylhexadecane (6R)-2,6-dimethylhexadecane CCCCCCCCCCC(C)CCCC(C)C InChI=1S/C18H38/c1-5-6-7-8-9-10-11-12-15-18(4)16-13-14-17(2)3/h17-18H,5-16H2,1-4H3/t18-/m1/s1 MMHVNKBJGUZQKC-GOSISDBHSA-N belongs to the class of organic compounds known as saturated hydrocarbons. These are hydrocarbons that contains only saturated carbon atoms, which are linked to one another through single bonds. These includes alkanes and cycloalkanes. Saturated hydrocarbons Organic compounds Hydrocarbons Saturated hydrocarbons Aliphatic acyclic compounds Aliphatic acyclic compound Saturated hydrocarbon logp 9.07 ALOGPS logs -7.38 ALOGPS logp 8.15 ChemAxon iupac (6R)-2,6-dimethylhexadecane ChemAxon average_mass 254.5 ChemAxon mono_mass 254.2974 ChemAxon smiles CCCCCCCCCCC(C)CCCC(C)C ChemAxon formula C18H38 ChemAxon inchi InChI=1S/C18H38/c1-5-6-7-8-9-10-11-12-15-18(4)16-13-14-17(2)3/h17-18H,5-16H2,1-4H3/t18-/m1/s1 ChemAxon inchikey MMHVNKBJGUZQKC-GOSISDBHSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 84.52 ChemAxon polarizability 36.81 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:49 UTC 2020-08-04 22:28:14 UTC CDB000248 3,6-Dimethyl-heptadecane 3,6-dimethyl-heptadecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons have the general formula CnH2n+2. 3,6-dimethyl-heptadecane is possibly neutral. 3,6-dimethyl-heptadecane is a dimethylated derivative of heptadecane. The name ‚Äúheptadecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C17H36, or to a mixture of them. This chemical formula allows for the theoretical existence of 24894 constitutional isomers. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-heptadecane, with a straight-chain CH3(CH2)15CH3. Heptadecane is considered to be a hydrocarbon lipid molecule. Heptadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptadecane is a fuel/diesel tasting compound. Outside of the human body, heptadecane is found in black walnuts, among other natural sources. Heptadecanes are combustible colourless liquids. They have no specific industrial value other than being a part of fuels and solvents. 3,6-dimethyl-heptadecane is one of many alkanes that are known in Cannabis plants (PMID: 6991645). C19H40 268.53 268.313 (3S,6S)-3,6-dimethylheptadecane (3S,6S)-3,6-dimethylheptadecane CCCCCCCCCCC[C@H](C)CC[C@@H](C)CC InChI=1S/C19H40/c1-5-7-8-9-10-11-12-13-14-15-19(4)17-16-18(3)6-2/h18-19H,5-17H2,1-4H3/t18-,19-/m0/s1 BWZKZWFGUKHRDZ-OALUTQOASA-N logp 9.29 ALOGPS logs -7.53 ALOGPS logp 8.6 ChemAxon iupac (3S,6S)-3,6-dimethylheptadecane ChemAxon average_mass 268.53 ChemAxon mono_mass 268.313 ChemAxon smiles CCCCCCCCCCC[C@H](C)CC[C@@H](C)CC ChemAxon formula C19H40 ChemAxon inchi InChI=1S/C19H40/c1-5-7-8-9-10-11-12-13-14-15-19(4)17-16-18(3)6-2/h18-19H,5-17H2,1-4H3/t18-,19-/m0/s1 ChemAxon inchikey BWZKZWFGUKHRDZ-OALUTQOASA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 89.12 ChemAxon polarizability 38.86 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:54 UTC 2020-08-04 22:28:14 UTC CDB000249 3,7-Dimethyl-heptadecane 3,7-dimethyl-heptadecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons have the general formula CnH2n+2. 3,7-dimethyl-heptadecane is possibly neutral. 3,7-dimethyl-heptadecane is a dimethylated derivative of heptadecane. The name ‚Äúheptadecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C17H36, or to a mixture of them. This chemical formula allows for the theoretical existence of 24894 constitutional isomers. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-heptadecane, with a straight-chain CH3(CH2)15CH3. Heptadecane is considered to be a hydrocarbon lipid molecule. Heptadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptadecane is a fuel/diesel tasting compound. Outside of the human body, heptadecane is found in black walnuts, among other natural sources. Heptadecanes are combustible colourless liquids. They have no specific industrial value other than being a part of fuels and solvents. 3,7-dimethyl-heptadecane is one of many alkanes that are known in Cannabis plants (PMID: 6991645). C19H40 268.53 268.313 (3S,7R)-3,7-dimethylheptadecane (3S,7R)-3,7-dimethylheptadecane CCCCCCCCCC[C@@H](C)CCC[C@@H](C)CC InChI=1S/C19H40/c1-5-7-8-9-10-11-12-13-15-19(4)17-14-16-18(3)6-2/h18-19H,5-17H2,1-4H3/t18-,19+/m0/s1 WMISHWDRQHFGPU-RBUKOAKNSA-N logp 9.29 ALOGPS logs -7.53 ALOGPS logp 8.6 ChemAxon iupac (3S,7R)-3,7-dimethylheptadecane ChemAxon average_mass 268.53 ChemAxon mono_mass 268.313 ChemAxon smiles CCCCCCCCCC[C@@H](C)CCC[C@@H](C)CC ChemAxon formula C19H40 ChemAxon inchi InChI=1S/C19H40/c1-5-7-8-9-10-11-12-13-15-19(4)17-14-16-18(3)6-2/h18-19H,5-17H2,1-4H3/t18-,19+/m0/s1 ChemAxon inchikey WMISHWDRQHFGPU-RBUKOAKNSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 89.12 ChemAxon polarizability 38.8 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:26:57 UTC 2020-08-04 22:28:14 UTC CDB000250 3,6-Dimethyl-octadecane 3,6-dimethyl-octadecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons have the general formula CnH2n+2. 3,6-dimethyl-octadecane is possibly neutral. 3,6-dimethyl-octadecane is a dimethylated derivative of octadecane. The name ‚Äúoctadecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C18H36, or to a mixture of them. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-heptadecane, with a straight-chain CH3(CH2)16CH3. Octadecane is considered to be a hydrocarbon lipid molecule. Octadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Octadecane is a fuel/diesel tasting compound. Octadecane is the alkane with the lowest number of carbon atoms unambiguously considered to be solid at room temperature and it appears in the form of white cristals. 3,6-dimethyl-octadecane is one of many alkanes that are known in Cannabis plants (PMID: 6991645). C20H42 282.56 282.3287 (3S,6S)-3,6-dimethyloctadecane (3S,6S)-3,6-dimethyloctadecane CCCCCCCCCCCC[C@H](C)CC[C@@H](C)CC InChI=1S/C20H42/c1-5-7-8-9-10-11-12-13-14-15-16-20(4)18-17-19(3)6-2/h19-20H,5-18H2,1-4H3/t19-,20-/m0/s1 FDWLWHCXNVXAOA-PMACEKPBSA-N logp 9.54 ALOGPS logs -7.64 ALOGPS logp 9.04 ChemAxon iupac (3S,6S)-3,6-dimethyloctadecane ChemAxon average_mass 282.56 ChemAxon mono_mass 282.3287 ChemAxon smiles CCCCCCCCCCCC[C@H](C)CC[C@@H](C)CC ChemAxon formula C20H42 ChemAxon inchi InChI=1S/C20H42/c1-5-7-8-9-10-11-12-13-14-15-16-20(4)18-17-19(3)6-2/h19-20H,5-18H2,1-4H3/t19-,20-/m0/s1 ChemAxon inchikey FDWLWHCXNVXAOA-PMACEKPBSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 93.72 ChemAxon polarizability 40.91 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:00 UTC 2020-08-04 22:28:14 UTC CDB000251 3,7-Dimethyl-octadecane 3,7-dimethyl-octadecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons have the general formula CnH2n+2. 3,7-dimethyl-octadecane is possibly neutral. 3,7-dimethyl-octadecane is a dimethylated derivative of octadecane. The name ‚Äúoctadecane‚Äù can be applied to any alkane hydrocarbon with the chemical formula C18H36, or to a mixture of them. However, the IUPAC nomenclature refers exclusively to one isomer, the normal or n-heptadecane, with a straight-chain CH3(CH2)16CH3. Octadecane is considered to be a hydrocarbon lipid molecule. Octadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Octadecane is a fuel/diesel tasting compound. Octadecane is the alkane with the lowest number of carbon atoms unambiguously considered to be solid at room temperature and it appears in the form of white cristals. 3,7-dimethyl-octadecane is one of many alkanes found in Cannabis plants (PMID: 6991645). C20H42 282.56 282.3287 (3S,7R)-3,7-dimethyloctadecane (3S,7R)-3,7-dimethyloctadecane CCCCCCCCCCC[C@@H](C)CCC[C@@H](C)CC InChI=1S/C20H42/c1-5-7-8-9-10-11-12-13-14-16-20(4)18-15-17-19(3)6-2/h19-20H,5-18H2,1-4H3/t19-,20+/m0/s1 XUQWDIMBTSCPPM-VQTJNVASSA-N logp 9.54 ALOGPS logs -7.64 ALOGPS logp 9.04 ChemAxon iupac (3S,7R)-3,7-dimethyloctadecane ChemAxon average_mass 282.56 ChemAxon mono_mass 282.3287 ChemAxon smiles CCCCCCCCCCC[C@@H](C)CCC[C@@H](C)CC ChemAxon formula C20H42 ChemAxon inchi InChI=1S/C20H42/c1-5-7-8-9-10-11-12-13-14-16-20(4)18-15-17-19(3)6-2/h19-20H,5-18H2,1-4H3/t19-,20+/m0/s1 ChemAxon inchikey XUQWDIMBTSCPPM-VQTJNVASSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 93.72 ChemAxon polarizability 40.93 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:04 UTC 2020-08-04 22:28:14 UTC CDB000252 3-Methylheneicosane 3-Methylheneicosane is a methylated derivative of heneicosane (CH3-[CH2]19-CH3). Heneicosane belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Heneicosane is considered to be a hydrocarbon lipid molecule and, as such, a very hydrophobic molecule, practically insoluble in water and relatively neutral. It is an alkane and waxy tasting compound. Heneicosane is a pheromone used by the queen or king termites from the Reticulitermes flavipes species (PMID: 29555778). Heneicosane also acts as a mosquito attractant, especially for those in the genus¬†Aedes¬†and can be used in mosquito baits (PMID: 19018567). Heneicosane is one of the major components of the safflower flower essential oil (Carthamus tinctorius) (PMID: 23371463). Furthermore, 3-methylheneicosane is one of many hydrocarbons that are known in Cannabis plants (PMID: 6991645). C22H46 310.61 310.36 (3S)-3-methylhenicosane (3S)-3-methylhenicosane CCCCCCCCCCCCCCCCCC[C@@H](C)CC InChI=1S/C22H46/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(3)5-2/h22H,4-21H2,1-3H3/t22-/m0/s1 OSJUENOXPFOHLF-QFIPXVFZSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane logp 10.19 ALOGPS logs -7.77 ALOGPS logp 10.09 ChemAxon iupac (3S)-3-methylhenicosane ChemAxon average_mass 310.61 ChemAxon mono_mass 310.36 ChemAxon smiles CCCCCCCCCCCCCCCCCC[C@@H](C)CC ChemAxon formula C22H46 ChemAxon inchi InChI=1S/C22H46/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(3)5-2/h22H,4-21H2,1-3H3/t22-/m0/s1 ChemAxon inchikey OSJUENOXPFOHLF-QFIPXVFZSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 102.97 ChemAxon polarizability 45.89 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 124514334 Funaro CF, Boroczky K, Vargo EL, Schal C: Identification of a queen and king recognition pheromone in the subterranean termite Reticulitermes flavipes. Proc Natl Acad Sci U S A. 2018 Apr 10;115(15):3888-3893. doi: 10.1073/pnas.1721419115. Epub 2018 Mar 19. 29555778 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Seenivasagan T, Sharma KR, Sekhar K, Ganesan K, Prakash S, Vijayaraghavan R: Electroantennogram, flight orientation, and oviposition responses of Aedes aegypti to the oviposition pheromone n-heneicosane. Parasitol Res. 2009 Mar;104(4):827-33. doi: 10.1007/s00436-008-1263-2. Epub 2008 Nov 19. 19018567 Asgarpanah J, Kazemivash N: Phytochemistry, pharmacology and medicinal properties of Carthamus tinctorius L. Chin J Integr Med. 2013 Feb;19(2):153-9. doi: 10.1007/s11655-013-1354-5. Epub 2013 Jan 31. 23371463 1.0 2020-03-19 00:27:06 UTC 2020-07-31 20:34:13 UTC CDB000253 3-Methyl-tricosane 3-Methyl-tricosane is a methylated derivative of tricosane. Tricosane, also known as CH3-[CH2]21-CH3, belongs to the class of organic compounds known as alkanes and consists of a straight chain alkane containing 23 carbon atoms. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Tricosane is considered to be a hydrocarbon lipid molecule. It is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Tricosane is an odorless, alkane tasting compound, which is solid at room temperature. Tricosane has been detected, but not quantified in, common hazelnuts. This could make tricosane a potential biomarker for the consumption of these foods. 3-Methyl-tricosane is one of many hydrocarbons that are known in Cannabis plants (PMID: 6991645). C24H50 338.66 338.3913 (3S)-3-methyltricosane (3S)-3-methyltricosane CCCCCCCCCCCCCCCCCCCC[C@@H](C)CC InChI=1S/C24H50/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(3)5-2/h24H,4-23H2,1-3H3/t24-/m0/s1 WCAGWYVPTZQWEN-DEOSSOPVSA-N logp 10.48 ALOGPS logs -7.89 ALOGPS logp 10.98 ChemAxon iupac (3S)-3-methyltricosane ChemAxon average_mass 338.66 ChemAxon mono_mass 338.3913 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC[C@@H](C)CC ChemAxon formula C24H50 ChemAxon inchi InChI=1S/C24H50/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(3)5-2/h24H,4-23H2,1-3H3/t24-/m0/s1 ChemAxon inchikey WCAGWYVPTZQWEN-DEOSSOPVSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 112.17 ChemAxon polarizability 50.17 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:11 UTC 2020-08-04 22:28:14 UTC CDB000254 Isopentacosane 2-methylTetracosane or Isopentacosane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, Isopentacosane is considered to be a hydrocarbon lipid molecule. Isopentacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Isopentacosane is the methylated derivative in position two of tetracosane. Tetracosane is an unbranched alkane hydrocarbon with the structural formula H3C(CH2)22CH3. Tetracosane has 14,490,245 thoeretical constitutional isomers and 252,260,276 possible stereoisomers. Isopentacosane has been detected, but not quantified in hop (Humulus lupus) and orange (Citrus sinensis) oil. Isopentacosane is also one of the hydrocarbons known to occur in Cannabis sativa plants (PMID: 6991645). Tetracosane, 2-methyl C25H52 352.68 352.4069 2-methyltetracosane 2-methyltetracosane 1560-78-7 CCCCCCCCCCCCCCCCCCCCCCC(C)C InChI=1S/C25H52/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25(2)3/h25H,4-24H2,1-3H3 YNQOGIZOCQEUJR-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane Hydrocarbons melting_point 56 °C logp 10.57 ALOGPS logs -7.92 ALOGPS logp 11.42 ChemAxon iupac 2-methyltetracosane ChemAxon average_mass 352.68 ChemAxon mono_mass 352.4069 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCC(C)C ChemAxon formula C25H52 ChemAxon inchi InChI=1S/C25H52/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25(2)3/h25H,4-24H2,1-3H3 ChemAxon inchikey YNQOGIZOCQEUJR-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 116.77 ChemAxon polarizability 52.39 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003071 459700 527459 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:13 UTC 2020-08-04 22:28:14 UTC CDB000255 3-Methyl-pentacosane 3-methyl-Pentacosane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. The straight chain in 3-methyl-Pentacosane consists of 25 carbon atoms with an additional methyl group in position 3. 3-methyl-pentacosane is considered to be a hydrocarbon lipid molecule. 3-Methyl-Pentacosane is a very hydrophobic molecule, practically insoluble in water and relatively neutral. 3-methyl-Pentacosane is one of the hydrocarbons that are known to occur in Cannabis sativa plants (PMID: 6991645). 3-methyl-Pentacosane is the methylated derivative pentacosane. Pentacosane is released into its surrounding atmosphere by worker bees (Appis mellifera) during their waggle dance, announcing a new food source and to recruit additional workers (PMID: 17713987). C26H54 366.72 366.4226 (3R)-3-methylpentacosane (3R)-3-methylpentacosane CCCCCCCCCCCCCCCCCCCCCC[C@H](C)CC InChI=1S/C26H54/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26(3)5-2/h26H,4-25H2,1-3H3/t26-/m1/s1 VNSJCJLDAGMPAO-AREMUKBSSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane logp 10.75 ALOGPS logs -7.96 ALOGPS logp 11.86 ChemAxon iupac (3R)-3-methylpentacosane ChemAxon average_mass 366.72 ChemAxon mono_mass 366.4226 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCC[C@H](C)CC ChemAxon formula C26H54 ChemAxon inchi InChI=1S/C26H54/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26(3)5-2/h26H,4-25H2,1-3H3/t26-/m1/s1 ChemAxon inchikey VNSJCJLDAGMPAO-AREMUKBSSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 121.38 ChemAxon polarizability 54.4 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12052908 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Thom C, Gilley DC, Hooper J, Esch HE: The scent of the waggle dance. PLoS Biol. 2007 Sep;5(9):e228. doi: 10.1371/journal.pbio.0050228. 17713987 1.0 2020-03-19 00:27:16 UTC 2020-08-04 22:28:14 UTC CDB000256 3-Methyl-heptacosane 3-methyl-Heptacosane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 3-methyl-Heptacosane is considered to be a hydrocarbon lipid molecule. 3-Methyl- heptacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 3-methyl-heptacosane is one of the hydrocarbons that known to occur in Cannabis sativa plants (PMID: 6991645). 3-methyl-heptacosane is a methylated derivative of heptacosane. Heptacosane can be found in a number of food items such as wild carrot, linden, sweet cherry, and papaya, which makes heptacosane a potential biomarker for the consumption of these food products. C28H58 394.77 394.4539 (3R)-3-methylheptacosane (3R)-3-methylheptacosane CCCCCCCCCCCCCCCCCCCCCCCC[C@H](C)CC InChI=1S/C28H58/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28(3)5-2/h28H,4-27H2,1-3H3/t28-/m1/s1 NTRHFQVDDLHZMZ-MUUNZHRXSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane logp 10.94 ALOGPS logs -8.02 ALOGPS logp 12.75 ChemAxon iupac (3R)-3-methylheptacosane ChemAxon average_mass 394.77 ChemAxon mono_mass 394.4539 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCC[C@H](C)CC ChemAxon formula C28H58 ChemAxon inchi InChI=1S/C28H58/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28(3)5-2/h28H,4-27H2,1-3H3/t28-/m1/s1 ChemAxon inchikey NTRHFQVDDLHZMZ-MUUNZHRXSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 130.58 ChemAxon polarizability 58.71 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12052909 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:19 UTC 2020-08-04 22:28:14 UTC CDB000257 9-Methyl-octacosane 9-Methyl-Octacosane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 9-methyl-Octacosane is considered to be a hydrocarbon lipid molecule. 3-Methyl- heptacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 9-methyl-Octacosane is a methylated derivative of Octacosane. Octacosane has been detected, but not quantified in, several different foods, such as peachs, coconuts, apples, sweet cherries, and lindens. 9-methyl-Octacosane is one of the hydrocarbons that are known to occur in Cannabis sativa plants (PMID: 6991645). C29H60 408.8 408.4695 (9R)-9-methyloctacosane (9R)-9-methyloctacosane CCCCCCCCCCCCCCCCCCC[C@H](C)CCCCCCCC InChI=1S/C29H60/c1-4-6-8-10-12-13-14-15-16-17-18-19-20-21-22-24-26-28-29(3)27-25-23-11-9-7-5-2/h29H,4-28H2,1-3H3/t29-/m1/s1 HGHNLISXMMUYAJ-GDLZYMKVSA-N logp 11.00 ALOGPS logs -8.02 ALOGPS logp 13.2 ChemAxon iupac (9R)-9-methyloctacosane ChemAxon average_mass 408.8 ChemAxon mono_mass 408.4695 ChemAxon smiles CCCCCCCCCCCCCCCCCCC[C@H](C)CCCCCCCC ChemAxon formula C29H60 ChemAxon inchi InChI=1S/C29H60/c1-4-6-8-10-12-13-14-15-16-17-18-19-20-21-22-24-26-28-29(3)27-25-23-11-9-7-5-2/h29H,4-28H2,1-3H3/t29-/m1/s1 ChemAxon inchikey HGHNLISXMMUYAJ-GDLZYMKVSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 135.18 ChemAxon polarizability 60.64 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:22 UTC 2020-08-04 22:28:15 UTC CDB000258 3-Methyl-triacontane 3-Methyl-Triacontane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 3-methyl-Triacontane is considered to be a hydrocarbon lipid molecule. 3-Methyl-Triacontane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 3-methyl-Triacontane is a methylated derivative of Triacontane. Triacontane is a straight-chain alkane with 30 carbon atoms. It appears as a waxy solid at room temperature. 3-Methyl-Triacontane is one of the hydrocarbons that are known to occur in Cannabis sativa plants (PMID: 6991645). C31H64 436.85 436.5008 (3S)-3-methyltriacontane (3S)-3-methyltriacontane CCCCCCCCCCCCCCCCCCCCCCCCCCC[C@@H](C)CC InChI=1S/C31H64/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31(3)5-2/h31H,4-30H2,1-3H3/t31-/m0/s1 NXCMTLDSKYDELZ-HKBQPEDESA-N logp 11.11 ALOGPS logs -8.01 ALOGPS logp 14.09 ChemAxon iupac (3S)-3-methyltriacontane ChemAxon average_mass 436.85 ChemAxon mono_mass 436.5008 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCC[C@@H](C)CC ChemAxon formula C31H64 ChemAxon inchi InChI=1S/C31H64/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31(3)5-2/h31H,4-30H2,1-3H3/t31-/m0/s1 ChemAxon inchikey NXCMTLDSKYDELZ-HKBQPEDESA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 144.38 ChemAxon polarizability 65.19 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:26 UTC 2020-08-04 22:28:15 UTC CDB000259 2-Methyl-hentriacontane 2-Methyl-Hentriacontane belongs to the class of organic compounds known as saturated hydrocarbons. These are acyclic branched hydrocarbons that contains only saturated carbon atoms, which are linked to one another through single bonds. These includes alkanes and cycloalkanes. Thus, 2-Methyl-Hentriacontane is considered to be a hydrocarbon lipid molecule. 2-Methyl-Hentriacontane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Methyl-Hentriacontane is a methylated derivative of Hentriacontane. Hentriacontane is found, on average, in the highest concentration within common pea. 2-Methyl-Hentriacontane is one of many alkanes that are found in cannabis plants (PMID: 6991645). C32H66 450.88 450.5165 2-methylhentriacontane 2-methylhentriacontane 1720-12-3 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C InChI=1S/C32H66/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32(2)3/h32H,4-31H2,1-3H3 XRBHKBOAKDZICV-UHFFFAOYSA-N belongs to the class of organic compounds known as saturated hydrocarbons. These are hydrocarbons that contains only saturated carbon atoms, which are linked to one another through single bonds. These includes alkanes and cycloalkanes. Saturated hydrocarbons Organic compounds Hydrocarbons Saturated hydrocarbons Aliphatic acyclic compounds Aliphatic acyclic compound Saturated hydrocarbon Hydrocarbons logp 11.01 ALOGPS logs -8.02 ALOGPS logp 14.53 ChemAxon iupac 2-methylhentriacontane ChemAxon average_mass 450.88 ChemAxon mono_mass 450.5165 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C ChemAxon formula C32H66 ChemAxon inchi InChI=1S/C32H66/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32(2)3/h32H,4-31H2,1-3H3 ChemAxon inchikey XRBHKBOAKDZICV-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 148.98 ChemAxon polarizability 67.42 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 14923238 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:30 UTC 2020-08-04 22:28:15 UTC CDB000260 2-Methyl-Dotriacontane 2-Methyl-Dotriacontane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 2-Methyl-Dotriacontane is considered to be a hydrocarbon lipid molecule. 2-MethylDotriacontane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Methyl-Dotriacontane is a methylated derivative of Dotriacontane. Dotriacontane exists as a solid under natural conditions. Dotriacontane has been detected, but not quantified in, several different foods, such as coconuts, garden tomato, papaya, and tea. 2-MethylDotriacontane is one of many hydrocarbons that are found in cannabis plants (PMID: 6991645). C33H68 464.91 464.5321 2-methyldotriacontane 2-methyldotriacontane 1720-11-2 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C InChI=1S/C33H68/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33(2)3/h33H,4-32H2,1-3H3 ZMRQKNNNZMSHKH-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane Hydrocarbons logp 11.08 ALOGPS logs -8.04 ALOGPS logp 14.98 ChemAxon iupac 2-methyldotriacontane ChemAxon average_mass 464.91 ChemAxon mono_mass 464.5321 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C ChemAxon formula C33H68 ChemAxon inchi InChI=1S/C33H68/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-32-33(2)3/h33H,4-32H2,1-3H3 ChemAxon inchikey ZMRQKNNNZMSHKH-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 153.58 ChemAxon polarizability 69.58 ChemAxon rotatable_bond_count 29 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 74399 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:32 UTC 2020-07-24 23:30:06 UTC CDB000261 tetra-triacontane Tetratriacontane is a long-chain hydrocarbon containing 34 carbons. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, Tetratriacontane is considered to be a hydrocarbon lipid molecule. Tetratriacontane is a very hydrophobic molecule, insoluble in water, and completely neutral. Tetratriacontane exists as a waxy solid. It is a naturally occurring compound that is found in several plant essential oils and in Candelilla wax. Candelilla wax is a wax derived from the leaves of the small Candelilla shrub native to northern Mexico and the southwestern United States. The Candelilla shrub is a member of the Euphorbia plant genus, from the family Euphorbiaceae. Candelilla wax is used as a food additive and as a glazing agent. It also used in cosmetic industry, as a component of lip balms and lotion bars. One of its major uses is as a binder for chewing gums. Candelilla wax can be used as a substitute for carnauba wax and beeswax. It is also used for making varnish. Tetratriacontane is one of the abundant alkanes are known in cannabis plant. (PMID: 6991645) N-Tetratriacontane C34H70 478.92 478.5478 tetratriacontane N-tetratriacontane 14167-59-0 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C34H70/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-34H2,1-2H3 GWVDBZWVFGFBCN-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons logp 11.15 ALOGPS logs -8.02 ALOGPS logp 15.58 ChemAxon iupac tetratriacontane ChemAxon average_mass 478.92 ChemAxon mono_mass 478.5478 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C34H70 ChemAxon inchi InChI=1S/C34H70/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-34H2,1-2H3 ChemAxon inchikey GWVDBZWVFGFBCN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 158.24 ChemAxon polarizability 72.07 ChemAxon rotatable_bond_count 31 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 26519 87443 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:36 UTC 2020-07-24 23:30:06 UTC CDB000262 pentatriacontane Pentatriacontane is a long-chain hydrocarbon containing 35 carbons. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, pentatriacontane is considered to be a hydrocarbon lipid molecule. Pentatriacontane is a very hydrophobic molecule, totally insoluble in water, and completely neutral. Pentatriacontane exists as a waxy solid. It is a naturally occurring compound that is found in parsley, several plant essential oils and in Candelilla wax. Candelilla wax is a wax derived from the leaves of the small Candelilla shrub native to northern Mexico and the southwestern United States. The Candelilla shrub is a member of the Euphorbia plant genus, from the family Euphorbiaceae. Candelilla wax is used as a food additive and a glazing agent. It also used in cosmetic industry, as a component of lip balms and lotion bars. One of its major uses is as a binder for chewing gums. Candelilla wax can be used as a substitute for carnauba wax and beeswax. It is also used for making varnish. Pentatriacontane is one of many alkanes that are known in cannabis plants (PMID: 6991645). C35H72 492.95 492.5634 pentatriacontane N-pentatriacontane 630-07-9 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C35H72/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-35H2,1-2H3 VHQQPFLOGSTQPC-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons logp 11.19 ALOGPS logs -8.02 ALOGPS logp 16.02 ChemAxon iupac pentatriacontane ChemAxon average_mass 492.95 ChemAxon mono_mass 492.5634 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C35H72 ChemAxon inchi InChI=1S/C35H72/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-35H2,1-2H3 ChemAxon inchikey VHQQPFLOGSTQPC-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 162.84 ChemAxon polarizability 74.22 ChemAxon rotatable_bond_count 32 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12413 FDB006490 Higher alkanes Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:39 UTC 2020-08-04 22:28:15 UTC CDB000263 (R)-1-Octen-3-ol (R)-1-Octen-3-ol, also known as octenol, 1-vinylhexanol or mushroom alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. (R)-1-Octen-3-ol is a neutral compound. (R)-1-Octen-3-ol is an alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-1-C-2. It has been isolated from a few essential oils such as those from lavender, leek, mint and mushrooms. Octenol is named ‚Äúmushroom alcohol‚Äù because is the main flavour component of¬†mushrooms. (R)-1-Octen-3-ol is a naturally occurring organic compound found in several plants including cannabis plants (PMID: 6991645). Octenol is formed during the oxidative breakdown of¬†linoleic acid. Octenol attracts biting insects, including mosquitoes. It is believed that some repellents, such as DEET, act by blocking the electrophysiological responses of octenol to the olfactory co-receptor (OR83b or ORCO), an olfactory receptor complex found in highly divergent insect populations (PMID: 18339904, PMID: 18711137). 1-OCTEN-3-ol C8H16O 128.21 128.1201 (3R)-oct-1-en-3-ol 1-octen-3-ol 3687-48-7 CCCCC[C@@H](O)C=C InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m0/s1 VSMOENVRRABVKN-QMMMGPOBSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Fatty alcohols oct-1-en-3-ol logp 2.43 ALOGPS logs -1.99 ALOGPS logp 2.49 ChemAxon pka_strongest_acidic 17.49 ChemAxon pka_strongest_basic -1.7 ChemAxon iupac (3R)-oct-1-en-3-ol ChemAxon average_mass 128.21 ChemAxon mono_mass 128.1201 ChemAxon smiles CCCCC[C@@H](O)C=C ChemAxon formula C8H16O ChemAxon inchi InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m0/s1 ChemAxon inchikey VSMOENVRRABVKN-QMMMGPOBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 40.17 ChemAxon polarizability 16.37 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6992244 39932 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Ditzen M, Pellegrino M, Vosshall LB: Insect odorant receptors are molecular targets of the insect repellent DEET. Science. 2008 Mar 28;319(5871):1838-42. doi: 10.1126/science.1153121. Epub 2008 Mar 13. 18339904 Syed Z, Leal WS: Mosquitoes smell and avoid the insect repellent DEET. Proc Natl Acad Sci U S A. 2008 Sep 9;105(36):13598-603. doi: 10.1073/pnas.0805312105. Epub 2008 Aug 18. 18711137 1.0 2020-03-19 00:27:44 UTC 2020-08-04 22:28:15 UTC CDB000265 (S)-3-Octanol (S)-3-Octanol, also known as 1-ethylhexanol or 3-octanol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, (S)-3-octanol is considered to be a fatty alcohol lipid molecule (S)-3-Octanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral (S)-3-Octanol is a citrus, earthy, and herbal tasting compound. (S)-3-Octanol is found in the highest concentration within a few different foods, such as cornmints, spearmints, and orange mints and in a lower concentration in hyssops, rosemaries, and common oregano. (S)-3-Octanol has also been detected, but not quantified, in several different foods, such as asparagus, summer savories, herbs and spices, soy beans, and alcoholic beverages. This could make (S)-3-octanol a potential biomarker for the consumption of these foods. (S)-3-octanol is one of several alcohols that have been found in cannabis plants (PMID: 6991645). C8H18O 130.23 130.1358 (3R)-octan-3-ol (3R)-octan-3-ol 589-98-0 CCCCC[C@H](O)CC InChI=1S/C8H18O/c1-3-5-6-7-8(9)4-2/h8-9H,3-7H2,1-2H3/t8-/m1/s1 NMRPBPVERJPACX-MRVPVSSYSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Fatty alcohols logp 2.84 ALOGPS logs -1.91 ALOGPS logp 2.63 ChemAxon pka_strongest_acidic 18.25 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (3R)-octan-3-ol ChemAxon average_mass 130.23 ChemAxon mono_mass 130.1358 ChemAxon smiles CCCCC[C@H](O)CC ChemAxon formula C8H18O ChemAxon inchi InChI=1S/C8H18O/c1-3-5-6-7-8(9)4-2/h8-9H,3-7H2,1-2H3/t8-/m1/s1 ChemAxon inchikey NMRPBPVERJPACX-MRVPVSSYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 40.28 ChemAxon polarizability 17.16 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 445789 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:47 UTC 2020-08-04 22:28:15 UTC CDB000266 1-Nonanol 1-Nonanol, also known as N-nonyl alcohol or 1-hydroxynonane, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. 1-Nonanol is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless to slightly yellow liquid with a citrus odor similar to citronella oil. 1-Nonanol is a very hydrophobic molecule, practically insoluble in water. 1-Nonanol is a bitter, clean, and dusty tasting compound. 1-Nonanol is widespread in nature and it is found in the highest concentration within a few different foods, such as corns, winter savories, and sweet oranges and in a lower concentration in mandarin orange (clementine, tangerine), limes, and peppermints. 1-Nonanol has also been detected, but not quantified in, gingers, rocket salad, muskmelons, mung beans, and evergreen blackberries. It also occurs in oils of orange, citronella and lemon and it is also found in cheese, prickly pears and bread. 1-Nonanol is one of several alcohols that are found in cannabis plants (PMID: 6991645). 1-Hydroxynonane N-Nonanol N-Nonyl alcohol Nonalol Nonyl alcohol Nonylalkohol Octyl carbinol Pelargonalkohol Pelargonic alcohol Acovenoside c Alcohol C9 FEMA 2789 N-Nonan-1-ol Nonan-1-ol Nonanol Nonyl alcohol, 8ci 1-Nonanol C9H20O 144.25 144.1514 nonan-1-ol nonanol 143-08-8 CCCCCCCCCO InChI=1S/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3 ZWRUINPWMLAQRD-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Fatty alcohols fatty alcohol water_solubility 0.14 mg/mL at 25 °C logp 3.77 melting_point -5 °C logp 3.76 ALOGPS logs -2.98 ALOGPS logp 3.03 ChemAxon pka_strongest_acidic 16.84 ChemAxon pka_strongest_basic -2 ChemAxon iupac nonan-1-ol ChemAxon average_mass 144.25 ChemAxon mono_mass 144.1514 ChemAxon smiles CCCCCCCCCO ChemAxon formula C9H20O ChemAxon inchi InChI=1S/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3 ChemAxon inchikey ZWRUINPWMLAQRD-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.14 ChemAxon polarizability 19.52 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB03143 FDB003307 C14696 8574 8914 F09 35986 C00030830 1-Nonanol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:27:52 UTC 2020-08-04 22:28:15 UTC CDB000267 hexadecanol-1 Cetyl alcohol, also known as 1-hexadecanol and palmityl alcohol, is a solid organic compound and a member of the alcohol class of compounds. Its chemical formula is CH3(CH2)15OH. At room temperature, Cetyl alcohol takes the form of a waxy white solid or flakes. It belongs to the group of fatty alcohols. With the demise of commercial whaling, cetyl alcohol is no longer primarily produced from whale oil, but instead either as an end-product of the petroleum industry or produced from vegetable oils such as palm oil and coconut oil. Production of cetyl alcohol from palm oil gives rise to one of its alternative names, palmityl alcohol. 1-Hexadecanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Hexadecanol is one of the simple alcohols found in cannabis (PMID: 6991645). It has a waxy or oily aroma and a ‚Äúclean cloth‚Äù waxy or oily taste. It is used in the food and cosmetic industry as an emollient, an emulsifying agent, a foam boosting agent, a masking agent, a surfactant, a viscosity controlling agent and a pacifying agent. Hexadecanol is found in, or is added to, shampoos, conditioners, toothpaste, inks, paints, pharmaceuticals, skin creams and lotions. It is also added to certain hard candies and frozen treats. People who suffer from eczema can be sensitive to hexadecanol as it is sometimes included in medications used for the treatment of eczema (PMID: 15059111). Cetyl alcohol is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 1-Cetanol 1-Hexadecyl alcohol 16-Hexadecanol Cetanol Cetyl alcohol Cetylalkohol Hexadecanol N-1-Hexadecanol N-Hexadecyl alcohol Palmityl alcohol 1-Hexadecyl alc 1-Hexanedecanol 1-Hydroxyhexadecane Adol Adol 52 Adol 52 NF Adol 52nf Adol 54 Alcohol C-16 Aldol 54 Alfol 16 Atalco C C16 Alcohol Cachalot C-50 Cachalot C-50 NF Cachalot C-51 Cachalot C-52 Ceraphyl ica Cetaffine Cetal Cetalol ca Cetostearyl alcohol Cetyl alcohol NF Cetylic alcohol Cetylol Crodacol C Crodacol C70 Crodacol C95NF Crodacol-cas Crodacol-cat Cyclal cetyl alcohol Dehydag wax 16 Dytol F-11 Elfacos C Epal 16nf Ethal Ethol Eutanol g16 Exxal 16 Fancol ca Fatty alcohol Hexadecan-1-ol Hexadecanol NF Hexadecyl alcohol Hyfatol Hyfatol 16 Isocetyl alcohol Isohexadecanol Isohexadecyl alcohol Lanette 16 Lanol C Lipocol C Lorol 24 Lorol C16 LorolL 24 Loxanol K Loxanol K extra Loxanwachs SK Loxiol VPG 1743 Michel xo-150-16 Myristyl alcohol N-Cetyl alcohol N-Hexadecan-1-ol N-Hexadecanol Normal primary hexadecyl alcohol Philcohol 1600 Product 308 Rita ca Siponol CC Siponol wax-a SSD SSD RP Cetyl alcohol, 14C-labeled Cetyl alcohol, aluminum salt 1-Hexadecanol C16H34O 242.44 242.261 hexadecan-1-ol cetyl alcohol 36311-34-9 CCCCCCCCCCCCCCCCO InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3 BXWNKGSJHAJOGX-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Long-chain fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Hydrocarbon derivative Long chain fatty alcohol Organic oxygen compound Organooxygen compound Primary alcohol Fatty alcohols Fatty alcohols a small molecule fatty alcohol 16:0 long-chain primary fatty alcohol water_solubility 1.34e-05 mg/mL at 25 °C melting_point 49.3 °C logp 7.17 ALOGPS logs -6.13 ALOGPS logp 6.14 ChemAxon pka_strongest_acidic 16.84 ChemAxon pka_strongest_basic -2 ChemAxon iupac hexadecan-1-ol ChemAxon average_mass 242.44 ChemAxon mono_mass 242.261 ChemAxon smiles CCCCCCCCCCCCCCCCO ChemAxon formula C16H34O ChemAxon inchi InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3 ChemAxon inchikey BXWNKGSJHAJOGX-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 77.35 ChemAxon polarizability 34.38 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 2581 FDB003051 DB09494 2682 C00823 16125 CPD-348 Cetyl_Alcohol 6927 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Soga F, Katoh N, Kishimoto S: Contact dermatitis due to lanoconazole, cetyl alcohol and diethyl sebacate in lanoconazole cream. Contact Dermatitis. 2004 Jan;50(1):49-50. doi: 10.1111/j.0105-1873.2004.00271j.x. 15059111 1.0 2020-03-19 00:27:59 UTC 2020-08-04 22:28:15 UTC CDB000269 2-Methyl-2-heptene-6-one 2-METHYL-2-HEPTENE belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. 2-METHYL-2-HEPTENE is possibly neutral. 2-methyl-2-heptene-6-one is one of the 13 ketones that have been identified in cannabis plant.(PMID: 6991645) C8H16 112.22 112.1252 2-methylhept-2-ene 2-methyl-2-heptene 627-97-4 CCCCC=C(C)C InChI=1S/C8H16/c1-4-5-6-7-8(2)3/h7H,4-6H2,1-3H3 WEPNJTDVIIKRIK-UHFFFAOYSA-N belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. Branched unsaturated hydrocarbons Organic compounds Hydrocarbons Unsaturated hydrocarbons Branched unsaturated hydrocarbons Aliphatic acyclic compounds Alkenes Unsaturated aliphatic hydrocarbons Acyclic olefin Aliphatic acyclic compound Alkene Branched unsaturated hydrocarbon Olefin Unsaturated aliphatic hydrocarbon logp 3.95 ALOGPS logs -2.47 ALOGPS logp 3.46 ChemAxon iupac 2-methylhept-2-ene ChemAxon average_mass 112.22 ChemAxon mono_mass 112.1252 ChemAxon smiles CCCCC=C(C)C ChemAxon formula C8H16 ChemAxon inchi InChI=1S/C8H16/c1-4-5-6-7-8(2)3/h7H,4-6H2,1-3H3 ChemAxon inchikey WEPNJTDVIIKRIK-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 39.41 ChemAxon polarizability 15.58 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12330 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:02 UTC 2020-08-04 22:28:15 UTC CDB000270 Decanone-2 2-Decanone, also known as N-C8H17COCH3 or decan-2-one, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). A methyl ketone that is decane in which the methylene hydrogens at position 2 are replaced by an oxo group. 2-Decanone is a very hydrophobic molecule, practically insoluble in water. It is a colorless water-like liquid with a floral, fatty and peach-like odor. It has a fermented cheesy taste. 2-Decanone is one of several ketones that are found in cannabis plants (PMID: 6991645). Outside of the human body, 2-Decanone is found, on average, in the highest concentration within kohlrabis. Methyl N-octyl ketone Methyl octyl ketone N-C8H17COCH3 Octyl methyl ketone Decan-2-one Decanedioic acid, monoethyl ester 2-Decanone C10H20O 156.27 156.1514 decan-2-one 2-decanone 693-54-9 CCCCCCCCC(C)=O InChI=1S/C10H20O/c1-3-4-5-6-7-8-9-10(2)11/h3-9H2,1-2H3 ZAJNGDIORYACQU-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons methyl ketone water_solubility 0.0768 mg/mL at 25 °C logp 3.73 melting_point 14 °C logp 3.63 ALOGPS logs -3.61 ALOGPS logp 3.47 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac decan-2-one ChemAxon average_mass 156.27 ChemAxon mono_mass 156.1514 ChemAxon smiles CCCCCCCCC(C)=O ChemAxon formula C10H20O ChemAxon inchi InChI=1S/C10H20O/c1-3-4-5-6-7-8-9-10(2)11/h3-9H2,1-2H3 ChemAxon inchikey ZAJNGDIORYACQU-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 48.43 ChemAxon polarizability 20.55 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004314 12218 12741 77929 C00034760 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:05 UTC 2020-08-04 22:28:15 UTC CDB000271 2-Undecanone 2-Undecanone, also known as undecan-2-one or rue ketone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). 2-Undecanone is a ketone, also known as methyl nonyl ketone (MNK). Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a base. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide. 2-Undecanone is a very hydrophobic molecule, practically insoluble in water but it is soluble in ethanol, benzene, chloroform, and acetone. 2-Undecanone is found in cloves and one of several ketones that are known in cannabis plants (PMID: 6991645). 2-Undecanone is found in palm kernel oil and soya bean oil. 2-Undecanone is an important constituent of rue oil (Ruta graveolens) and found in many other essential oils. Also found in black currant buds, raspberry, black berry peach and other fruits. 2-Undecanone is used in flavourings It is found naturally in bananas, cloves, ginger, guava, strawberries, and wild-grown tomatoes. 2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect repellent or animal repellent. 2-Hendecanone Methyl nonyl ketone Rue ketone Undecan-2-one 2-Oxoundecane Enodyl FEMA 3093 Ketone, methyl nonyl Luparone Methyl N-nonyl ketone Methyl-N-nonylketone Methylnonylketone MGK Dog AMP MNK Nonyl methyl ketone Undecanone Undecanone-(2) BioUD 2-Undecanone C11H22O 170.29 170.1671 undecan-2-one undecan-2-one 112-12-9 CCCCCCCCCC(C)=O InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 KYWIYKKSMDLRDC-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons Oxygenated hydrocarbons a small molecule dialkyl ketone methyl ketone logp 4.09 melting_point 15 °C logp 4.25 ALOGPS logs -4.16 ALOGPS logp 3.92 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac undecan-2-one ChemAxon average_mass 170.29 ChemAxon mono_mass 170.1671 ChemAxon smiles CCCCCCCCCC(C)=O ChemAxon formula C11H22O ChemAxon inchi InChI=1S/C11H22O/c1-3-4-5-6-7-8-9-10-11(2)12/h3-10H2,1-2H3 ChemAxon inchikey KYWIYKKSMDLRDC-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 53.03 ChemAxon polarizability 22.66 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7871 FDB011831 8163 17700 C01875 DB08688 UOC 2-UNDECANONE C00030758 2-Undecanone Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:09 UTC 2020-08-04 22:28:15 UTC CDB000272 Dodecanone-2 2-Dodecanone, also known as dodecan-2-one or dodecanone-(2), belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more Œ±-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-dodecanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Dodecanone is a very hydrophobic molecule, practically insoluble in water. 2-Dodecanone is a citrus, floral, and fruity tasting compound. 2-Dodecanone has been detected, but not quantified, in several different foods, such as alcoholic beverages, fats and oils, garden tomato, and herbs and spices. 2-Dodecanone is one of several ketones that are known to occur in cannabis plants (PMID: 6991645). 12-(2,3-Dihydroxycyclopentyl)-2-dodecanone 2,3-Epoxypropyl methanesulphonate Decyl methyl ketone Dodecan-2-one Dodecanone-(2) Methyl decyl ketone N-Decyl methyl ketone C12H24O 184.32 184.1827 dodecan-2-one methyl decyl ketone 6175-49-1 CCCCCCCCCCC(C)=O InChI=1S/C12H24O/c1-3-4-5-6-7-8-9-10-11-12(2)13/h3-11H2,1-2H3 LSKONYYRONEBKA-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons melting_point 21 °C logp 4.74 ALOGPS logs -4.84 ALOGPS logp 4.36 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac dodecan-2-one ChemAxon average_mass 184.32 ChemAxon mono_mass 184.1827 ChemAxon smiles CCCCCCCCCCC(C)=O ChemAxon formula C12H24O ChemAxon inchi InChI=1S/C12H24O/c1-3-4-5-6-7-8-9-10-11-12(2)13/h3-11H2,1-2H3 ChemAxon inchikey LSKONYYRONEBKA-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 57.63 ChemAxon polarizability 24.77 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003012 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:12 UTC 2020-08-04 22:28:15 UTC CDB000273 pentadecanone-2 2-Pentadecanone, also known as fema 3724, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more Œ±-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 2-Pentadecanone is a very hydrophobic molecule, practically insoluble in water. 2-Pentadecanone is a celery, fresh, and jasmin tasting compound. It has been detected, but not quantified, in several different foods, such as milk and milk products, cauliflowers, cereals and cereal products, asparagus, and fruits. It has been isolated from hop (Humulus lupulus), coconut (Cocos nucifera) and other oils and it is also found in American cranberry, feijoa fruit, quince, asparagus, ginger, wheat bread, soybean, cooked rice and cheeses. Pentadecanone-2 is also one of several ketones known to occur in cannabis plants (PMID: 6991645). 2-Pentandecanone FEMA 3724 Methyl tridecyl ketone Pentadecan-2-one C15H30O 226.4 226.2297 pentadecan-2-one 2-pentadecanone 2345-28-0 CCCCCCCCCCCCCC(C)=O InChI=1S/C15H30O/c1-3-4-5-6-7-8-9-10-11-12-13-14-15(2)16/h3-14H2,1-2H3 CJPNOLIZCWDHJK-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons a ketone melting_point 39 °C logp 6.26 ALOGPS logs -6.08 ALOGPS logp 5.7 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac pentadecan-2-one ChemAxon average_mass 226.4 ChemAxon mono_mass 226.2297 ChemAxon smiles CCCCCCCCCCCCCC(C)=O ChemAxon formula C15H30O ChemAxon inchi InChI=1S/C15H30O/c1-3-4-5-6-7-8-9-10-11-12-13-14-15(2)16/h3-14H2,1-2H3 ChemAxon inchikey CJPNOLIZCWDHJK-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 71.43 ChemAxon polarizability 31.16 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003086 55242 61303 C00036262 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:16 UTC 2020-08-04 22:28:15 UTC CDB000274 octanone-3 Ethyl pentyl ketone, also known as octan-3-one or 3-octanon, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more Œ±-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, ethyl pentyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. Ethyl pentyl ketone is a very hydrophobic molecule, practically insoluble in water. Ethyl pentyl ketone has been detected, but not quantified, in cardamoms and lemons. 3-Octanone is one of several ketones that are known to occur in cannabis plants (PMID: 6991645). 3-Oxooctane Amyl ethyl ketone EAK Ethyl amyl ketone Ethyl N-amyl ketone Ethyl N-pentyl ketone N-Amyl ethyl ketone Octan-3-one 3-Octanon 3-Octanone Ethyl N-amylketone FEMA 2803 N-Octanone-3 Ethyl pentyl ketone C8H16O 128.21 128.1201 octan-3-one 3-octanone 106-68-3 CCCCCC(=O)CC InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3 RHLVCLIPMVJYKS-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons ketone water_solubility 2.6 mg/mL at 20 °C logp 2.61 ALOGPS logs -1.94 ALOGPS logp 2.84 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac octan-3-one ChemAxon average_mass 128.21 ChemAxon mono_mass 128.1201 ChemAxon smiles CCCCCC(=O)CC ChemAxon formula C8H16O ChemAxon inchi InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3 ChemAxon inchikey RHLVCLIPMVJYKS-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 39.25 ChemAxon polarizability 16.28 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB005050 215929 246728 80946 C17145 C00034765 3-Octanone Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:19 UTC 2020-08-04 22:28:15 UTC CDB000275 (±)-2,2,6-Trimethylcyclohexanone (¬±)-2,2,6-Trimethylcyclohexanone belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety (¬±)-2,2,6- It is a trimethylated derivative of Cyclohexanone. (¬±)-2,2,6-Trimethylcyclohexanone is a cistus, honey, and labdanum tasting compound. Outside of the human body, (¬±)-2,2,6-Trimethylcyclohexanone has been detected in cauliflowers and oats. 2,2,6-Trimethylcyclohexanone is one of several ketones that are known to occur in cannabis plants (PMID: 6991645). C9H16O 140.23 140.1201 (6R)-2,2,6-trimethylcyclohexan-1-one (6R)-2,2,6-trimethylcyclohexan-1-one 2408-37-9 C[C@@H]1CCCC(C)(C)C1=O InChI=1S/C9H16O/c1-7-5-4-6-9(2,3)8(7)10/h7H,4-6H2,1-3H3/t7-/m1/s1 ZPVOLGVTNLDBFI-SSDOTTSWSA-N belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Cyclic ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic homomonocyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic homomonocyclic compound Cyclic ketone Hydrocarbon derivative Organic oxide logp 2.47 ALOGPS logs -1.93 ALOGPS logp 3.13 ChemAxon pka_strongest_basic -7.5 ChemAxon iupac (6R)-2,2,6-trimethylcyclohexan-1-one ChemAxon average_mass 140.23 ChemAxon mono_mass 140.1201 ChemAxon smiles C[C@@H]1CCCC(C)(C)C1=O ChemAxon formula C9H16O ChemAxon inchi InChI=1S/C9H16O/c1-7-5-4-6-9(2,3)8(7)10/h7H,4-6H2,1-3H3/t7-/m1/s1 ChemAxon inchikey ZPVOLGVTNLDBFI-SSDOTTSWSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 41.9 ChemAxon polarizability 16.84 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6999893 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:21 UTC 2020-08-04 22:28:15 UTC CDB000276 3-Decen-5-one 3-Decen-5-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. These are unbranched acyclic ketones with a (C=C) double bond. An enone, also called an Œ±, Œ≤-unsaturated carbonyl, is a type of organic compound consisting of an alkene conjugated to a ketone. Enones are typically produced using an aldol condensation or Knoevenagel condensation. Some commercially significant enones produced by condensations of acetone are mesityl oxide (dimer of acetone) and phorone and isophorone (trimers) (https://doi.org/10.1002/14356007.a15_077). 3-Decen-5-one is one of several ketones that are found in cannabis plants (PMID: 6991645). C10H18O 154.25 154.1358 dec-3-en-5-one dec-3-en-5-one 32064-73-6 CCCCCC(=O)C=CCC InChI=1S/C10H18O/c1-3-5-7-9-10(11)8-6-4-2/h6,8H,3-5,7,9H2,1-2H3 IWQQYVVAYYANSF-UHFFFAOYSA-N belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Enones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Acryloyl compounds Hydrocarbon derivatives Ketones Organic oxides Acryloyl-group Aliphatic acyclic compound Enone Hydrocarbon derivative Ketone Organic oxide logp 3.38 ALOGPS logs -2.96 ALOGPS logp 3.73 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac dec-3-en-5-one ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CCCCCC(=O)C=CCC ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-3-5-7-9-10(11)8-6-4-2/h6,8H,3-5,7,9H2,1-2H3 ChemAxon inchikey IWQQYVVAYYANSF-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 49.55 ChemAxon polarizability 19.72 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 557934 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:24 UTC 2020-08-04 22:28:15 UTC CDB000277 6,10-Dimethyl-2-undecanone 6,10-Dimethyl-2-undecanone belongs to the class of organic compounds known as branched ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 6,10-dimethylundecan-2-one is practically insoluble in water and an extremely weak acidic compound (based on its pKa). 6,10-Dimethyl-2-undecanone is a dimethylated derivative of 2-Undecanone. 6,10-Dimethyl-2-Undecanone is one of several ketones that are known to occur in cannabis plants (PMID: 6991645). 6,10-dimethyl-2-undecanone can also be found in tea. C13H26O 198.35 198.1984 (6R)-6,10-dimethylundecan-2-one (6R)-6,10-dimethylundecan-2-one CC(C)CCC[C@@H](C)CCCC(C)=O InChI=1S/C13H26O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h11-12H,5-10H2,1-4H3/t12-/m1/s1 RBGLEUBCAJNCTR-GFCCVEGCSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide logp 4.96 ALOGPS logs -5.26 ALOGPS logp 4.49 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac (6R)-6,10-dimethylundecan-2-one ChemAxon average_mass 198.35 ChemAxon mono_mass 198.1984 ChemAxon smiles CC(C)CCC[C@@H](C)CCCC(C)=O ChemAxon formula C13H26O ChemAxon inchi InChI=1S/C13H26O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h11-12H,5-10H2,1-4H3/t12-/m1/s1 ChemAxon inchikey RBGLEUBCAJNCTR-GFCCVEGCSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 62.13 ChemAxon polarizability 26.11 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1715160 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:28 UTC 2020-08-04 22:28:15 UTC CDB000278 6,10,14-Trimethyl-pentadecan-2-one 6,10,14-trimethyl-Pentadecan-2-one, also known as hexahydrofarnesylacetone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms with three consecutive isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). 6,10,14-trimethyl-Pentadecan-2-one is one of several ketones that are known in cannabis plants (PMID: 6991645). 6,10,14-trimethyl-pentadecan-2-one is a celery, fat, and herbal tasting compound and can be found in a number of food items such as sweet basil, common oregano, roselle, and wild celery. (6R,10R)-6,10,14-Trimethyl-2-pentadecanone (+)-(R,R)-Phytone (+)-Phytone (6R,10R)-6,10,14-Trimethylpentadecan-2-one (R,R)-Phytone Phytol ketone Phytone 6,10,14-Trimethyl-2-pentadecanone (±)-Phytone Hexahydrofarnesyl acetone Perhydrofarnesyl acetone C18H36O 268.49 268.2766 (6R,10R)-6,10,14-trimethylpentadecan-2-one (6R,10R)-6,10,14-trimethylpentadecan-2-one CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)=O InChI=1S/C18H36O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h15-17H,6-14H2,1-5H3/t16-,17-/m1/s1 WHWDWIHXSPCOKZ-IAGOWNOFSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Ketones Organic oxides Aliphatic acyclic compound Carbonyl group Farsesane sesquiterpenoid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Sesquiterpenoid logp 7.48 ALOGPS logs -6.83 ALOGPS logp 6.56 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac (6R,10R)-6,10,14-trimethylpentadecan-2-one ChemAxon average_mass 268.49 ChemAxon mono_mass 268.2766 ChemAxon smiles CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)=O ChemAxon formula C18H36O ChemAxon inchi InChI=1S/C18H36O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h15-17H,6-14H2,1-5H3/t16-,17-/m1/s1 ChemAxon inchikey WHWDWIHXSPCOKZ-IAGOWNOFSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 85.08 ChemAxon polarizability 36.16 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1810793 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:28:33 UTC 2020-07-31 20:34:13 UTC CDB000279 Arabinonic acid Arabinonic acid or arabinic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Arabinonic acid is an organic compound with molecular formula of C5H10O6. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Arabinonic acid is an acidic monosaccharide containing arabinose unit and which is obtained from gum arabic, in which it is present as salts. Arabinonic acid is one several acids that are known in cannabis plants (PMID: 6991645). L-Xylonate L-Xylonic acid ​L-xylonate 2,3,4,5-Tetrahydroxypentanoic acid Xylonate Xylonic acid D-Xylonic acid C5H10O6 166.13 166.0477 (2S,3R,4S)-2,3,4,5-tetrahydroxypentanoic acid L-xylonic acid 4172-44-5 OC[C@H](O)[C@@H](O)[C@H](O)C(O)=O InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3+,4-/m0/s1 QXKAIJAYHKCRRA-NUNKFHFFSA-N belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Pentoses Polyols Primary alcohols Secondary alcohols Short-chain hydroxy acids and derivatives Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Pentose monosaccharide Polyol Primary alcohol Secondary alcohol Short-chain hydroxy acid Sugar acid xylonic acid logp -2.48 ALOGPS logs 0.19 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S,3R,4S)-2,3,4,5-tetrahydroxypentanoic acid ChemAxon average_mass 166.13 ChemAxon mono_mass 166.0477 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@H](O)C(O)=O ChemAxon formula C5H10O6 ChemAxon inchi InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3+,4-/m0/s1 ChemAxon inchikey QXKAIJAYHKCRRA-NUNKFHFFSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 32.31 ChemAxon polarizability 14.26 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6971043 C05411 Xylonic acid 48092 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:39 UTC 2020-07-31 20:34:15 UTC CDB000280 Malonic acid Malonic acid, also known as malonate or H2MALO, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing two carboxylic acid groups. Malonic acid is a very hydrophobic molecule, practically insoluble in water. Malonic acid exists in all living species, ranging from bacteria to humans. In humans, malonic acid is involved in fatty acid biosynthesis. Malonic acid has also been detected, but not quantified, in several different foods, such as red beetroots, corns, scarlet beans, common beets, and cow milks. Malonic acid is also one of several organic acids that are known to occur in cannabis plants (PMID: 6991645). Industrially, it is used in a number of manufacturing processes as a high value specialty chemical, including the electronics industry, flavors and fragrances industry, specialty solvents, polymer crosslinking, and pharmaceutical industry. H2Malo HOOC-CH2-COOH Propanedioic acid Propanedioate Malonate alpha,Omega-dicarboxylic acid Carboxyacetic acid Dicarboxylate Dicarboxylic acid Dicarboxymethane Kyselina malonova Malonate dicarboxylic acid Metahnedicarboxylic acid Methanedicarbonic acid Methanedicarboxylic acid Propanedioic acid dithallium salt Propanediolic acid Thallium malonate Malonic acid, 2-(14)C-labeled Malonic acid, monocalcium salt Malonic acid, 1,3-(14)C2-labeled Malonic acid, diammonium salt Malonic acid, disodium salt Malonic acid, dithallium salt Malonic acid, dipotassium salt Malonic acid, disodium salt, 1-(14)C-labeled Malonic acid, monosodium salt Malonic acid, potassium salt Malonic acid, sodium salt Thallous malonate Dithallium malonate Monosodium malonate Malonic acid C3H4O4 104.06 104.011 propanedioic acid malonic acid 141-82-2 OC(=O)CC(O)=O InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) OFOBLEOULBTSOW-UHFFFAOYSA-N belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Dicarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives Aliphatic acyclic compounds 1,3-dicarbonyl compounds Carboxylic acids Hydrocarbon derivatives Organic oxides 1,3-dicarbonyl compound Aliphatic acyclic compound Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Dicarboxylic acids alpha,omega-dicarboxylic acid water_solubility 763.0 mg/mL logp -0.81 HANSCH,C ET AL. (1995) melting_point 135 °C logp -0.60 ALOGPS logs 0.28 ALOGPS logp -0.33 ChemAxon pka_strongest_acidic 2.43 ChemAxon iupac propanedioic acid ChemAxon average_mass 104.06 ChemAxon mono_mass 104.011 ChemAxon smiles OC(=O)CC(O)=O ChemAxon formula C3H4O4 ChemAxon inchi InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) ChemAxon inchikey OFOBLEOULBTSOW-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 18.99 ChemAxon polarizability 8.13 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C04025 DB02175 FDB008117 844 30794 867 MALONATE C00001193 Malonic_acid 3237 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:42 UTC 2020-08-04 22:28:15 UTC CDB000281 2-C-Methylaldotetronic acid 2-C-Methylaldotetronic acid, belongs to the class of organic compounds known as branched acids. 2-C-Methylaldotetronic acid is a naturally occurring organic compound found in plants such as cannabis and peyote. It is a lactone-forming acid (probably the erythro form) present in considerable amounts in cannabis plants (PMID: 6991645). There are two known 2-C-Methylaldotetronic acid isomers including L- and D- configurations. 2-C Methylaldotetronic acid is the open acid form of 2-c-methyl-Aldotetronolactone. 2-Methyl-L-threonate C5H10O5 150.13 150.0528 (2R,3S)-2,3,4-trihydroxy-2-methylbutanoic acid (2R,3S)-2,3,4-trihydroxy-2-methylbutanoic acid C[C@@](O)([C@@H](O)CO)C(O)=O InChI=1S/C5H10O5/c1-5(10,4(8)9)3(7)2-6/h3,6-7,10H,2H2,1H3,(H,8,9)/t3-,5+/m0/s1 UXJDESUVPBNUTB-WVZVXSGGSA-N belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Monosaccharides Organic oxides Polyols Primary alcohols Secondary alcohols Short-chain hydroxy acids and derivatives Tertiary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy acid Hydroxy fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol Short-chain hydroxy acid Sugar acid Tertiary alcohol logp -1.71 ALOGPS logs 0.58 ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 3.53 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S)-2,3,4-trihydroxy-2-methylbutanoic acid ChemAxon average_mass 150.13 ChemAxon mono_mass 150.0528 ChemAxon smiles C[C@@](O)([C@@H](O)CO)C(O)=O ChemAxon formula C5H10O5 ChemAxon inchi InChI=1S/C5H10O5/c1-5(10,4(8)9)3(7)2-6/h3,6-7,10H,2H2,1H3,(H,8,9)/t3-,5+/m0/s1 ChemAxon inchikey UXJDESUVPBNUTB-WVZVXSGGSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 31.06 ChemAxon polarizability 13.51 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 102150672 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:46 UTC 2020-07-07 15:57:01 UTC CDB000282 eicosadienic acid Eicosadienic acid, also known as eicosadienate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Eicosadienic acid is a weakly acidic compound (based on its pKa). Eicosadienic acid is one of the fatty acids that have are known in the hemp (cannabis) seed oil. (PMID: 28448475) Eicosadienate Icosa-2,4-dienoate C20H36O2 308.51 308.2715 icosa-2,4-dienoic acid icosa-2,4-dienoic acid CCCCCCCCCCCCCCCC=CC=CC(O)=O InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h16-19H,2-15H2,1H3,(H,21,22) LNAVIIOBBICBIS-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid logp 8.49 ALOGPS logs -6.94 ALOGPS logp 7.67 ChemAxon pka_strongest_acidic 4.94 ChemAxon iupac icosa-2,4-dienoic acid ChemAxon average_mass 308.51 ChemAxon mono_mass 308.2715 ChemAxon smiles CCCCCCCCCCCCCCCC=CC=CC(O)=O ChemAxon formula C20H36O2 ChemAxon inchi InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h16-19H,2-15H2,1H3,(H,21,22) ChemAxon inchikey LNAVIIOBBICBIS-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 97.7 ChemAxon polarizability 41.2 ChemAxon rotatable_bond_count 16 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 54042050 1.0 2020-03-19 00:28:48 UTC 2020-08-04 22:28:15 UTC CDB000283 p-Ethyl benzyl acetate p-Ethylbenzyl acetate, also known as Styralyl acetate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxy group. p-Ethylbenzyl acetate is also classified as an ester and is an ethylated derivative of benzyl acetate. p-Ethylbenzyl acetate has a sweet, floral, slightly fruity odour of Jasmine-Gardenia. Industrially, it is produced via the esterification of ethylbenzyl alcohol with acetic acid. p-Ethylbenzyl acetate is found in the essential oils of various plants such as ylang-ylang and flowers like jasmine. p-Ethylbenzyl acetate exists as a colorless, clear, oily liquid. It is a neutral, hydrophobic molecule that is essentially insoluble in water. p-Ethylbenzyl acetate is an ester found in the essential oil of cannabis plants (PMID: 6991645). p-Ethylbenzyl acetic acid C11H14O2 178.23 178.0994 (4-ethylphenyl)methyl acetate (4-ethylphenyl)methyl acetate CCC1=CC=C(COC(C)=O)C=C1 InChI=1S/C11H14O2/c1-3-10-4-6-11(7-5-10)8-13-9(2)12/h4-7H,3,8H2,1-2H3 IMQVSQQYENMRCT-UHFFFAOYSA-N belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyloxycarbonyls Organic compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls Aromatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aromatic homomonocyclic compound Benzyloxycarbonyl Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 3.02 ALOGPS logs -3.48 ALOGPS logp 2.61 ChemAxon pka_strongest_basic -7 ChemAxon iupac (4-ethylphenyl)methyl acetate ChemAxon average_mass 178.23 ChemAxon mono_mass 178.0994 ChemAxon smiles CCC1=CC=C(COC(C)=O)C=C1 ChemAxon formula C11H14O2 ChemAxon inchi InChI=1S/C11H14O2/c1-3-10-4-6-11(7-5-10)8-13-9(2)12/h4-7H,3,8H2,1-2H3 ChemAxon inchikey IMQVSQQYENMRCT-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 51.67 ChemAxon polarizability 20.24 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12732713 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:51 UTC 2020-08-04 22:28:15 UTC CDB000284 2-C-Methyl-aldotetronolactone 2-C-Methyl-1,4-erythrono-D-lactone, 2-C-methyl-D-erythrono-1,4-lactone (MDEL) or 2-C-Methyl-Aldotetronolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-membered ring with four carbon atoms, one oxygen atom, forming part of a carboxyl functional group. 2-C-Methyl-1,4-erythrono-D-lactone is a neutral, hydrophobic molecule that is not soluble in water. 2-C-Methyl-1,4-erythrono-D-lactone is a known constituent of Trifolium incarnatum (crimson clover) and Phaseolus vulgaris (kidney bean). It has also been detected, but not quantified in several different foods, such as green beans, pulses, tea, and yellow wax beans. It has been identified as an insect pheromone that acts as an oviposition stimulant for the Swallowtail butterfly (PMID: 11055405). 2-C-Methyl-1,4-erythrono-D-lactone is synthesized in plants via the terpenoid precursor 1‚Äêdeoxy‚ÄêD‚Äêxylulose, which is phosphorylated to 1‚Äêdeoxy‚ÄêD‚Äêxylulose‚Äê5‚Äêphosphate, which is then transformed by the enzyme 1‚Äêdeoxy‚ÄêD‚Äêxylulose‚Äê5‚Äêphosphate reducto isomerase to 2C‚ÄêMethyl‚ÄêD‚Äêerythritol‚Äê4‚Äêphosphate. This compound is then oxidized at the alcoholic group at C‚Äê1 to 2-Methyl-2,3,4-trihydroxybutanoic acid-4-phosphate by an uncharacterized dehydrogenase. Dephosphorylation yields the free acid which spontaneously forms the lactone. 2-C-Methyl-1,4-erythrono-D-lactone is one of a small number of lactones found in cannabis plants (PMID: 6991645). C5H8O4 132.12 132.0423 (3R,4R)-3,4-dihydroxy-3-methyloxolan-2-one (3R,4R)-3,4-dihydroxy-3-methyloxolan-2-one 18465-71-9 C[C@@]1(O)[C@H](O)COC1=O InChI=1S/C5H8O4/c1-5(8)3(6)2-9-4(5)7/h3,6,8H,2H2,1H3/t3-,5-/m1/s1 OHTGZAWPVDWARE-NQXXGFSBSA-N belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Gamma butyrolactones Organic compounds Organoheterocyclic compounds Lactones Gamma butyrolactones Aliphatic heteromonocyclic compounds 1,2-diols Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Oxolanes Secondary alcohols Tertiary alcohols 1,2-diol Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Gamma butyrolactone Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Oxolane Secondary alcohol Tertiary alcohol logp -1.46 ALOGPS logs 0.80 ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 11.57 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (3R,4R)-3,4-dihydroxy-3-methyloxolan-2-one ChemAxon average_mass 132.12 ChemAxon mono_mass 132.0423 ChemAxon smiles C[C@@]1(O)[C@H](O)COC1=O ChemAxon formula C5H8O4 ChemAxon inchi InChI=1S/C5H8O4/c1-5(8)3(6)2-9-4(5)7/h3,6,8H,2H2,1H3/t3-,5-/m1/s1 ChemAxon inchikey OHTGZAWPVDWARE-NQXXGFSBSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 27.57 ChemAxon polarizability 11.7 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11126294 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Ono H, Nishida R, Kuwahara Y: A dihydroxy-gamma-lactone as an oviposition stimulant for the swallowtail butterfly, Papilio bianor, from the rutaceous plant, Orixa japonica. Biosci Biotechnol Biochem. 2000 Sep;64(9):1970-3. doi: 10.1271/bbb.64.1970. 11055405 1.0 2020-03-19 00:28:53 UTC 2020-08-04 22:28:15 UTC CDB000285 Octyl caproate Octyl caproate or Octyl hexanoate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of an alcohol with a medium to long chain aliphatic group. Octyl caproate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It exists as a clear liquid and has a bland, fruity, mildly herbaceous odor. Octyl caproate is found naturally in a number of plants including muskmelon and parsnip. Fatty esters, such as octyl caproate, are often found in the cuticle of plant‚Äôs aerial parts. The hydrophobic properties of these molecules allow the cuticle to serve as a barrier for dehydration. Octyl caproate is one of several esters that are found in cannabis plants (PMID: 6991645). Octyl hexanoic acid C14H28O2 228.38 228.2089 octyl hexanoate octyl caproate 4887-30-3 CCCCCCCCOC(=O)CCCCC InChI=1S/C14H28O2/c1-3-5-7-8-9-11-13-16-14(15)12-10-6-4-2/h3-13H2,1-2H3 CMNMHJVRZHGAAK-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Fatty alcohol esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohol esters Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty alcohol ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters logp 5.65 ALOGPS logs -5.24 ALOGPS logp 5.06 ChemAxon pka_strongest_basic -7 ChemAxon iupac octyl hexanoate ChemAxon average_mass 228.38 ChemAxon mono_mass 228.2089 ChemAxon smiles CCCCCCCCOC(=O)CCCCC ChemAxon formula C14H28O2 ChemAxon inchi InChI=1S/C14H28O2/c1-3-5-7-8-9-11-13-16-14(15)12-10-6-4-2/h3-13H2,1-2H3 ChemAxon inchikey CMNMHJVRZHGAAK-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 68.12 ChemAxon polarizability 29.89 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21006 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:28:57 UTC 2020-08-04 22:28:15 UTC CDB000286 campest-5-en-3β-ol-7-one Campest-5-en-3Œ≤-ol-7-one or Campest-5-en-3beta-ol-7-one is an oxidized derivative of Campesterol (Campest-5-en-3-beta-ol) that has C=O double bond on the C-7 carbon. Campest-5-en-3Œ≤-ol-7-one is a neutral, hydrophobic molecule that is insoluble in water. Campest-5-en-3Œ≤-ol-7-one is a phytosterol, meaning it is a steroid derived from plants. Phytosterols have a cholesterol-like structure consisting of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or the presence or absence of a double bond. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. Phytosterols play a similar role to cholesterol in stabilizing membrane lipids in plants. In humans the intake of naturally occurring phytosterols ranges between ~200‚Äì300 mg/day depending on eating habits (PMID: 28702423). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423). They may also have a role in cancer prevention and treatment (PMID: 26086253). Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. Campest-5-en-3Œ≤-ol-7-one is one of the several phytosterols found in the roots and leaves of cannabis plants (PMID: 6991645). C28H46O2 414.67 414.3498 (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h16-19,21-24,26,29H,7-15H2,1-6H3/t18-,19-,21+,22-,23+,24+,26+,27+,28-/m1/s1 LTLKHSBYMNKWPF-KANLMKGOSA-N belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Ergosterols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Ergostane steroids Aliphatic homopolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids 7-oxosteroids Cyclic alcohols and derivatives Cyclohexenones Delta-5-steroids Hydrocarbon derivatives Organic oxides Secondary alcohols 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid 7-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Cyclohexenone Delta-5-steroid Ergosterol-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol logp 5.82 ALOGPS logs -6.42 ALOGPS logp 6.84 ChemAxon pka_strongest_acidic 17.39 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one ChemAxon average_mass 414.67 ChemAxon mono_mass 414.3498 ChemAxon smiles CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O ChemAxon formula C28H46O2 ChemAxon inchi InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h16-19,21-24,26,29H,7-15H2,1-6H3/t18-,19-,21+,22-,23+,24+,26+,27+,28-/m1/s1 ChemAxon inchikey LTLKHSBYMNKWPF-KANLMKGOSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 125.81 ChemAxon polarizability 52.59 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 101704474 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. 28702423 Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. 26086253 1.0 2020-03-19 00:29:00 UTC 2020-08-04 22:28:15 UTC CDB000287 5α-Stigmasta-7,24(28)-dien-3β-ol 5Œ±-Stigmasta-7,24(28)-dien-3Œ≤-ol is a steroid derivative characterized by a hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 7-8 the B ring, and position 24-25 in the alkyl substituent. It belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. 5Œ±-Stigmasta-7,24(28)-dien-3Œ≤-ol is a neutral, hydrophobic molecule that is insoluble in water. 5Œ±-Stigmasta-7,24(28)-dien-3Œ≤-ol is a naturally occurring phytosterol found in plants. Phytosterols have a cholesterol-like structure consisting of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or the presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200‚Äì300 mg/day depending on eating habits (PMID: 28702423). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423). They may also have a role in cancer prevention and treatment (PMID: 26086253). Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. 5Œ±-Stigmasta-7,24(28)-dien-3Œ≤-ol is one of the phytosterols found in cannabis plants and oils (PMID: 6991645). 7-Dehydroavenasterol Δ7-Avenasterol (24Z)-24-Ethyl-5alpha-cholesta-7,24(28)-dien-3beta-ol (24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol (Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-ol 24Z-Ethylidenelathosterol 3beta-Hydroxy-5alpha-stigmasta-7,24(28)Z-diene 5alpha-Stigmasta-7,24(28)-dien-3-ol 5alpha-Stigmasta-7,24(28)-dien-3beta-ol 5alpha-Stigmasta-7,Z-24(28)-diene-3.beta-ol Avenasterol Z-24-Ethylidene-5alpha-cholest-7-en-3beta-ol (24Z)-24-Ethyl-5α-cholesta-7,24(28)-dien-3β-ol (24Z)-5α-Stigmasta-7,24(28)-dien-3β-ol (3beta,5alpha,24Z)-Stigmasta-7,24(28)-dien-3-ol (3β,5α,24Z)-Stigmasta-7,24(28)-dien-3-ol (Z)-5α-Stigmasta-7,24(28)-dien-3β-ol 3β-Hydroxy-5α-stigmasta-7,24(28)Z-diene 5alpha-Stigmasta-7,Z-24(28)-diene-3beta-ol 5α-Stigmasta-7,24(28)-dien-3-ol 5α-Stigmasta-7,Z-24(28)-diene-3β-ol Z-24-Ethylidene-5α-cholest-7-en-3β-ol delta7-Avenasterol C29H48O 412.7 412.3705 (1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol (1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol 23290-26-8 C\C=C(\CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-/t20-,22+,23+,25-,26+,27+,28+,29-/m1/s1 MCWVPSBQQXUCTB-OQTIOYDCSA-N belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmastanes and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Stigmastanes and derivatives Aliphatic homopolycyclic compounds 3-beta-hydroxysteroids 3-hydroxy delta-7-steroids Cyclic alcohols and derivatives Delta-7-steroids Hydrocarbon derivatives Secondary alcohols Triterpenoids 3-beta-hydroxysteroid 3-hydroxy-delta-7-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Delta-7-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Stigmastane-skeleton Triterpenoid Stigmasterols and C24-ethyl derivatives logp 7.62 ALOGPS logs -6.65 ALOGPS logp 7.44 ChemAxon pka_strongest_acidic 18.36 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol ChemAxon average_mass 412.7 ChemAxon mono_mass 412.3705 ChemAxon smiles C\C=C(\CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C ChemAxon formula C29H48O ChemAxon inchi InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-/t20-,22+,23+,25-,26+,27+,28+,29-/m1/s1 ChemAxon inchikey MCWVPSBQQXUCTB-OQTIOYDCSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 130.62 ChemAxon polarizability 53.66 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB030685 24850097 12795736 C15782 C00007322 CPD-4125 Avenasterol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. 28702423 Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. 26086253 1.0 2020-03-19 00:29:04 UTC 2020-08-04 22:28:15 UTC CDB000288 Stigmasta-5,22-dien-3β-ol-7-one Stigmasta-5,22-dien-3Œ≤-ol-7-one is a derivative of stigmasterol (stigmasta-5,22-dien-3Œ≤-ol) that has C=O double bond positioned on the C-7 carbon. It belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. Stigmasta-5,22-dien-3Œ≤-ol-7-one is a neutral, hydrophobic molecule that is insoluble in water. It is a phytosterol, meaning it is steroid derived from plants. Phytosterols have a cholesterol-like structure consisting of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or the presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200‚Äì300 mg/day depending on eating habits (PMID: 28702423). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423). They may also have a role in cancer prevention and treatment (PMID: 26086253). Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Stigmasta-5,22-dien-3Œ≤-ol-7-one is one of several phytosterols that are found in cannabis plants (https://doi.org/10.1007/978-1-59259-947-9_2), (PMID: 6991645). C29H46O2 426.69 426.3498 (1S,2R,5S,10R,11R,14R,15R)-14-[(2R,3Z,5R)-5-ethyl-6-methylhept-3-en-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one (1S,2R,5S,10R,11R,14R,15R)-14-[(2R,3Z,5R)-5-ethyl-6-methylhept-3-en-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one CC[C@@H](\C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O)C(C)C InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h8-9,17-20,22-25,27,30H,7,10-16H2,1-6H3/b9-8-/t19-,20+,22+,23-,24-,25+,27-,28+,29-/m1/s1 UKMCCFHULJHJNS-RBXNOROVSA-N logp 5.80 ALOGPS logs -6.41 ALOGPS logp 6.92 ChemAxon pka_strongest_acidic 17.39 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1S,2R,5S,10R,11R,14R,15R)-14-[(2R,3Z,5R)-5-ethyl-6-methylhept-3-en-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one ChemAxon average_mass 426.69 ChemAxon mono_mass 426.3498 ChemAxon smiles CC[C@@H](\C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O)C(C)C ChemAxon formula C29H46O2 ChemAxon inchi InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h8-9,17-20,22-25,27,30H,7,10-16H2,1-6H3/b9-8-/t19-,20+,22+,23-,24-,25+,27-,28+,29-/m1/s1 ChemAxon inchikey UKMCCFHULJHJNS-RBXNOROVSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 131.53 ChemAxon polarizability 52.41 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. 28702423 Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. 26086253 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:29:08 UTC 2020-08-04 22:28:15 UTC CDB000289 7-keto-β-Sitosterol 7-keto-Œ≤-Sitosterol or 3-Hydroxystigmast-5-en-7-one is a derivative of Beta-sitosterol that has C=O double bond positioning on C-7. It belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. 7-keto-Œ≤-Sitosterol is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol. Phytosterols consist of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200‚Äì300 mg/day depending on eating habits (PMID: 28702423). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423). They may also have a role in cancer prevention and treatment (PMID: 26086253). Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. 7-keto-Œ≤-Sitosterol or 3-Hydroxystigmast-5-en-7-one is found in plants belonging to the Brassica family and can be isolated after saponification from Brassica napus (rapeseed) and Glycine max (soyabean) oil. 7-keto-Œ≤-Sitosterol is one of several phytosterols found in cannabis plants (PMID: 6991645). C29H48O2 428.7 428.3654 (1R,2R,5S,10S,11R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one (1R,2R,5S,10S,11R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one CC[C@@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3[C@@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O)C(C)C InChI=1S/C29H48O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h17-20,22-25,27,30H,7-16H2,1-6H3/t19-,20+,22+,23-,24-,25-,27+,28+,29-/m1/s1 ICFXJOAKQGDRCT-MURBDQLESA-N logp 6.25 ALOGPS logs -6.64 ALOGPS logp 7.28 ChemAxon pka_strongest_acidic 17.39 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1R,2R,5S,10S,11R,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one ChemAxon average_mass 428.7 ChemAxon mono_mass 428.3654 ChemAxon smiles CC[C@@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@H]3[C@@H](CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O)C(C)C ChemAxon formula C29H48O2 ChemAxon inchi InChI=1S/C29H48O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h17-20,22-25,27,30H,7-16H2,1-6H3/t19-,20+,22+,23-,24-,25-,27+,28+,29-/m1/s1 ChemAxon inchikey ICFXJOAKQGDRCT-MURBDQLESA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 130.41 ChemAxon polarizability 52.98 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. 28702423 Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. 26086253 1.0 2020-03-19 00:29:12 UTC 2020-08-04 22:28:15 UTC CDB000290 Stigmast-4-en-3-one Stigmast-4-en-3-one belongs to the class of organic compounds known as stigmastanes and derivatives. These are steroid-like molecules with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 and a trans double bond in position C22. Stigmast-4-en-3-one is a naturally occurring phytosterol found in plants. Phytosterols consist of four fused rings as a core structure and an acyclic side chain. Phytosterols differ only in carbon side chains and/or presence or absence of a double bond. They play a similar role to cholesterol in stabilizing membrane lipids in plants. Phytosterols derive from the same biosynthetic precursor as the triterpenoids (2,3-oxidosqualene) and their biosynthesis also proceeds via the mevalonic acid pathway (MVA), mainly in the cytosol. In humans the intake of naturally occurring phytosterols ranges between ~200‚Äì300 mg/day depending on eating habits (PMID: 28702423). Phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines) and can reduce cholesterol in human subjects by up to 15% (PMID: 28702423). They may also have a role in cancer prevention and treatment (PMID: 26086253). Stigmast-4-en-3-one is one of several phytosterols found in cannabis plants (PMID: 6991645). Stigmast-4-en-3-one (24R)-24-Ethylcholest-4-en-3-one (24R)-Stigmast-4-en-3-one 4-En-3-stigmastone Sitostenone delta4-Sitosterol-3-one Δ4-Sitosterol-3-one delta4-Stigmasten-3-one Δ4-Stigmasten-3-one beta-Rosasterol oxide β-Rosasterol oxide beta-Sitost-4-en-3-one β-Sitost-4-en-3-one beta-Sitostenone C29H48O 412.7 412.3705 (1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 67392-96-5 CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1 RUVUHIUYGJBLGI-XJZKHKOHSA-N belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmastanes and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Stigmastanes and derivatives Aliphatic homopolycyclic compounds 3-oxo delta-4-steroids Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides Triterpenoids 3-oxo-delta-4-steroid 3-oxosteroid Aliphatic homopolycyclic compound Carbonyl group Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Stigmastane-skeleton Triterpenoid steroid logp 6.95 ALOGPS logs -7.40 ALOGPS logp 8.41 ChemAxon pka_strongest_acidic 19.09 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac (1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one ChemAxon average_mass 412.7 ChemAxon mono_mass 412.3705 ChemAxon smiles CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C ChemAxon formula C29H48O ChemAxon inchi InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1 ChemAxon inchikey RUVUHIUYGJBLGI-XJZKHKOHSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 128.71 ChemAxon polarizability 53.53 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5484202 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Jesch ED, Carr TP: Food Ingredients That Inhibit Cholesterol Absorption. Prev Nutr Food Sci. 2017 Jun;22(2):67-80. doi: 10.3746/pnf.2017.22.2.67. Epub 2017 Jun 30. 28702423 Ramprasath VR, Awad AB: Role of Phytosterols in Cancer Prevention and Treatment. J AOAC Int. 2015 May-Jun;98(3):735-738. doi: 10.5740/jaoacint.SGERamprasath. 26086253 1.0 2020-03-19 00:29:14 UTC 2020-07-07 15:57:07 UTC CDB000291 camphenehydrate Camphene-hydrate, also known as 3-Methylcamphenilol, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene-hydrate is a neutral, hydrophobic molecule that is practically insoluble in water. It is a colorless solid with a musty camphoreous odor. Camphene-hydrate can be found in ginger and is one of many monoterpenes that are found in cannabis plants (PMID: 6991645). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. C10H18O 154.25 154.1358 (1S,2S,4R)-2,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (1S,2S,4R)-2,3,3-trimethylbicyclo[2.2.1]heptan-2-ol CC1(C)[C@@H]2CC[C@@H](C2)[C@]1(C)O InChI=1S/C10H18O/c1-9(2)7-4-5-8(6-7)10(9,3)11/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1 PXRCIOIWVGAZEP-WEDXCCLWSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol logp 2.87 ALOGPS logs -2.29 ALOGPS logp 2.05 ChemAxon pka_strongest_basic -0.4 ChemAxon iupac (1S,2S,4R)-2,3,3-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@@H]2CC[C@@H](C2)[C@]1(C)O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-8(6-7)10(9,3)11/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1 ChemAxon inchikey PXRCIOIWVGAZEP-WEDXCCLWSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.4 ChemAxon polarizability 18.35 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21631093 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:29:18 UTC 2020-07-07 15:57:07 UTC CDB000292 delta4-carene Delta-4-Carene or (+)-4-Carene, or simply 4-Carene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Delta4-Carene is also classified as a cycloalkene (with molecular formula of C10H16) although it is biochemically a monoterpenoid as it synthesized via multiple isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are several isomers of Carene, including Delta-2-Carene, Delta-3-Carene and Delta-4-Carene. Delta-4-Carene is a hydrophobic, neutral molecule that is insoluble in water. Delta-4-Carene has been detected, but not quantified in rosemary, black currants and as a volatile component in tomatoes (PMID: 24096821). It exhibits larvicidal activities and appears to be active against the third stage larvae of mosquitoes that carry malaria, Dengue and filariasis (PMID: 27151483). It is one of many terpenes that are found in cannabis plants (PMID: 6991645). Delta-4-Carene is one of more than 140 terpenes in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. C10H16 136.24 136.1252 (1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene (1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene C[C@H]1C[C@H]2[C@H](C=C1)C2(C)C InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3/t7-,8+,9+/m1/s1 LGNSZMLHOYDATP-VGMNWLOBSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Carane monoterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 3.46 ALOGPS logs -4.29 ALOGPS logp 2.85 ChemAxon iupac (1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles C[C@H]1C[C@H]2[C@H](C=C1)C2(C)C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3/t7-,8+,9+/m1/s1 ChemAxon inchikey LGNSZMLHOYDATP-VGMNWLOBSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.99 ChemAxon polarizability 17.31 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 90473900 Fang Y, Jiao X, Xie W, Wang S, Wu Q, Shi X, Chen G, Su Q, Yang X, Pan H, Zhang Y: Tomato yellow leaf curl virus alters the host preferences of its vector Bemisia tabaci. Sci Rep. 2013 Oct 7;3:2876. doi: 10.1038/srep02876. 24096821 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Govindarajan M, Rajeswary M, Benelli G: delta-Cadinene, Calarene and .delta-4-Carene from Kadsura heteroclita Essential Oil as Novel Larvicides Against Malaria, Dengue and Filariasis Mosquitoes. Comb Chem High Throughput Screen. 2016;19(7):565-71. doi: 10.2174/1386207319666160506123520. 27151483 1.0 2020-03-19 00:29:22 UTC 2020-08-04 22:28:15 UTC CDB000293 (±)-cis-Linalyl oxide (¬±)-cis-Linalyl oxide, also known as cis-Linalool-oxide or Linalool oxide B, is an oxidized derivative of Linalool which is a terpene alcohol common in various flowers and spice plants. It belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Biochemically, cis-Linalool-oxide is a monoterpenoid as it synthesized via multiple isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Linalool oxide occurs in two distinctly different structural guises in nature. The most common structural form is based on a five member, furan-like ring structure. The less common form is based on a six member, pyran-like structure. Both types of linalool oxide exist as cis- and trans- isomers. Despite the differences in structure, the aromas of the different forms of linalool oxide have a strong family resemblance. The furan-based linalool oxide has a floral character, somewhat reminiscent of lavender, but this is dominated by the profile of black tea. The pyran-based linalool oxide is more obviously floral, with less resemblance to tea. More specifically, cis-Linalool-oxide has a sweet, earthy, and floral aroma and is used as a perfuming agent and a flavoring agent. cis-Linalool-oxide exists as a clear or slightly yellow oil. It is a neutral, hydrophobic molecule that is insoluble in water. cis-Linalool-oxide is found in black and green tea leaves has also been detected, but not quantified in, several different foods, spices or oils, such as sweet basils, black elderberries, coriander, common oregano, garden tomato (var.), peppermint oil and papaya. cis-Linalool oxide is also found in Lavender (https://doi.org/10.4028/www.scientific.net/KEM.688.31). Cis-Linalool oxide is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. C10H18O2 170.25 170.1307 2-[(2S,5R)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol 2-[(2S,5R)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol 11063-77-7 CC(C)(O)[C@@H]1CC[C@@](C)(O1)C=C InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10-/m0/s1 BRHDDEIRQPDPMG-WPRPVWTQSA-N belongs to the class of organic compounds known as oxolanes. These are organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms. Oxolanes Organic compounds Organoheterocyclic compounds Oxolanes Aliphatic heteromonocyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Tertiary alcohols Alcohol Aliphatic heteromonocyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Oxolane Tertiary alcohol logp 1.51 ALOGPS logs -2.05 ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 14.32 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 2-[(2S,5R)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol ChemAxon average_mass 170.25 ChemAxon mono_mass 170.1307 ChemAxon smiles CC(C)(O)[C@@H]1CC[C@@](C)(O1)C=C ChemAxon formula C10H18O2 ChemAxon inchi InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10-/m0/s1 ChemAxon inchikey BRHDDEIRQPDPMG-WPRPVWTQSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 49.04 ChemAxon polarizability 19.47 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11116492 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:24 UTC 2020-08-04 22:28:15 UTC CDB000294 (±)-trans-Linalyl oxide (¬±)-trans-Linalyl oxide, also known as (E)-linalool oxide or trans-Linalool oxide is an oxidized derivative of Linalool which is a terpene alcohol common in various flowers and spice plants. It belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. From a biosynthetic point of view, trans-Linalool oxide is a monoterpenoid. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Linalool oxide occurs in two distinctly different structural guises in nature. The most common structural form is based on a five member, furan-like ring structure. The less common form is based on a six member, pyran-like structure. Both types of linalool oxide exist as cis- and trans- isomers. Despite the differences in structure, the aromas of the different forms of linalool oxide have a strong family resemblance. The furan-based linalool oxide has a floral character, somewhat reminiscent of lavender, but this is dominated by the profile of black tea. The pyran-based linalool oxide is more obviously floral, with less resemblance to tea. It is used as a perfuming agent and a flavoring agent. trans-Linalool oxide exists as a clear or slightly yellow oil. It is a neutral, hydrophobic molecule that is insoluble in water. (¬±)-trans-Linalyl oxide is found within tea and ceylon cinnamons and has also been detected, but not quantified in, several different foods, such as common oregano, sweet basils, garden tomatoes, gingers, and tarragons. trans-Linalool oxide is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita (e)-Linalool oxide a 5-Ethenyltetrahydro-a,a,5-trimethyl-(2R,5R)-rel-2-furanmethanol e-Linalool oxide (furanoid) Linalool oxide a Linalool oxide II trans-Furanoid linalool oxide trans-Linalool 3,6-oxide trans-Linalool oxide (furanoid) C10H18O2 170.25 170.1307 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol 34995-77-2 CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1 BRHDDEIRQPDPMG-WCBMZHEXSA-N belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Tetrahydrofurans Organic compounds Organoheterocyclic compounds Tetrahydrofurans Aliphatic heteromonocyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Tertiary alcohols Alcohol Aliphatic heteromonocyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Tertiary alcohol Tetrahydrofuran logp 1.51 ALOGPS logs -2.05 ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 14.32 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 2-[(2S,5S)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol ChemAxon average_mass 170.25 ChemAxon mono_mass 170.1307 ChemAxon smiles CC(C)(O)[C@@H]1CC[C@](C)(O1)C=C ChemAxon formula C10H18O2 ChemAxon inchi InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m0/s1 ChemAxon inchikey BRHDDEIRQPDPMG-WCBMZHEXSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 49.04 ChemAxon polarizability 19.52 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB020535 4937513 6432254 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:27 UTC 2020-08-04 22:28:15 UTC CDB000295 m-Mentha-1,8(9)-dien-5-ol m-Mentha-1,8(9)-dien-5-ol or meta-Mentha-1,8(9)-dien-5-ol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. M-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 3 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. M-mentha-1,8(9)-dien-5-ol is formally classified as an alcohol although it is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. M-mentha-1,8(9)-dien-5-ol is one of 140 terpenes that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. M-mentha-1,8(9)-dien-5-ol is a unique terpenoid found only in Cannabis. C10H16O 152.24 152.1201 (1R,5R)-3-methyl-5-(prop-1-en-2-yl)cyclohex-3-en-1-ol (1R,5R)-3-methyl-5-(prop-1-en-2-yl)cyclohex-3-en-1-ol CC(=C)[C@@H]1C[C@@H](O)CC(C)=C1 InChI=1S/C10H16O/c1-7(2)9-4-8(3)5-10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m0/s1 SFULVKXOLMZBEC-UWVGGRQHSA-N logp 2.42 ALOGPS logs -1.71 ALOGPS logp 1.83 ChemAxon pka_strongest_acidic 18.61 ChemAxon pka_strongest_basic -1.2 ChemAxon iupac (1R,5R)-3-methyl-5-(prop-1-en-2-yl)cyclohex-3-en-1-ol ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles CC(=C)[C@@H]1C[C@@H](O)CC(C)=C1 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-7(2)9-4-8(3)5-10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m0/s1 ChemAxon inchikey SFULVKXOLMZBEC-UWVGGRQHSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 48.15 ChemAxon polarizability 18.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:29:29 UTC 2020-08-04 22:28:16 UTC CDB000296 Dehydro-p-cymene para-Mentha-1,3,5,8-tetraene, also known as Dehydro-p-cymene, p-alpha-dimethyl-styrene, Habanene or p-Cymenene, belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. Dehydro-p-cymene is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Dehydro-p-cymene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Dehydro-p-cymene has a herbaceous, leathery, peppery odor with notes of elemi oil and thyme, as well as a touch of citrus. It has an oregano, clove, basalmic, spicy taste. Dehydro-p-cymene is used as a flavoring agent for Italian dishes and for enhancing habanero spices. Dehydro-p-cymene is found in the highest concentration within star anises but it has also been detected in several different foods, such as lemons, coffee, dill, evergreen blackberries, parsley, citrus, sage, spearmint and pepper. Dehydro-p-cymene is one of more than 140 terpenes that are found in cannabis plants (PMID:6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. 1-Isopropenyl-4-methylbenzene 1-Methyl-4-(1-methylethenyl)-benzene 1-Methyl-4-(1-methylethenyl)benzene 1-Methyl-4-(1-methylethenyl)benzene, 9ci 1-Methyl-4-isopropenylbenzene 1-Methyl-4alpha-methylstyrene 2-(4-Methylphenyl)propene 2-(p-Methylphenyl)propene 2-p-Tolylpropene 4-Isopropenyltoluene 4-Methyl-alpha-methylstyrene 4-Methylisopropenylbenzene alpha,4-Dimethylstyrene alpha,p-Dimethylstyrene alpha-Dimethyl-p-styrene alpha-Methyl-p-methylstyrene alpha-p Dimethylstyrene Cymenene Dehydro-p-cymene FEMA 3144 Ghl.PD_Mitscher_leg0.317 Isopropenyl toluene c Methyl-4-(1-methylethenyl)-benzene Methyl-p-isopropenylbenzene p,a-Dimethylstyrene, 8ci p,alpha-Dimethyl-styrene p,alpha-Dimethylstyrene p,alpha-Dimethylstyrol p-alpha-Dimethyl-styrene p-alpha-Dimethylstyrene p-Cymenene p-Isopropenyl toluene p-Isopropenyltoluene p-Methyl-alpha-methylstyrene Para- alpha-dimethylstyrene C10H12 132.2 132.0939 1-methyl-4-(prop-1-en-2-yl)benzene 1-methyl-4-(prop-1-en-2-yl)benzene 1195-32-0 CC(=C)C1=CC=C(C)C=C1 InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3 MMSLOZQEMPDGPI-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. Phenylpropenes Organic compounds Benzenoids Benzene and substituted derivatives Phenylpropenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Branched unsaturated hydrocarbons Cyclic olefins Styrenes Toluenes Aromatic homomonocyclic compound Aromatic hydrocarbon Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Phenylpropene Styrene Toluene Unsaturated hydrocarbon melting_point -20 °C logp 3.79 ALOGPS logs -2.92 ALOGPS logp 3.52 ChemAxon iupac 1-methyl-4-(prop-1-en-2-yl)benzene ChemAxon average_mass 132.2 ChemAxon mono_mass 132.0939 ChemAxon smiles CC(=C)C1=CC=C(C)C=C1 ChemAxon formula C10H12 ChemAxon inchi InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3 ChemAxon inchikey MMSLOZQEMPDGPI-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 45.07 ChemAxon polarizability 16.35 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000812 56173 62385 C00010905 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:32 UTC 2020-09-11 20:08:26 UTC CDB000297 cis-β-ocimene Cis-Œ≤-Ocimene or cis-Beta-Ocimene is a naturally occurring organic compound found within a variety of plants and fruits. It is formally classified as an alkatriene although it is biochemically an acyclic monoterpene as it synthesized via multiple isoprene units. Acyclic monoterpens do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). There are three known Ocimene isomers including Alpha-, cis-Beta and trans-Beta-Ocimene. Alpha-Ocimene is known as 3,7-dimethyl-1,3,7-octatriene. Beta-Ocimene is known as 3,7-dimethyl-1,3,6-octatriene. Beta-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. Ocimenes are believed to act as plant defense chemicals and have anti-fungal properties. Cis-Œ≤-Ocimene is a neutral, very hydrophobic molecule, practically insoluble in water. It exists as a pale, colorless oil. cis-Beta-Ocimene has a warm, floral, sweet odor and has a spicy, green, metallic taste. It is found naturally in a number of plants and foods including allspice, anise, basil, bay leaf, caraway seed, celery, cinnamon, coriander, dill, fennel, grapefruit, guava, lavender, lemons, limes, mandarin oranges, papaya and parsley. Cis-Œ≤-Ocimene is one of more than 140 monoterpenes that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. beta-cis-Ocimene cis-3,7-Dimethyl-1,3,6-octatriene b-cis-Ocimene Β-cis-ocimene cis-&beta;-ocimene (3Z)-3,7-Dimethyl-1,3,6-octatriene (Z)-3,7-Dimethyl-1,3,6-octatriene (Z)-3,7-Dimethylocta-1,3,6,-triene (Z)-beta-Ocimene 3,7-Dimethyl-(3Z)-1,3,6-octatriene 3,7-Dimethyl-(Z)-1,3,6-octatriene beta -(Z)-Ocimene beta -cis-Ocimene cis-beta -Ocimene cis-beta-Ocimene Z-beta -Ocimene Z-Ocimene (Z)-b-Ocimene (Z)-Β-ocimene cis-b-Ocimene cis-Β-ocimene C10H16 136.23 136.1252 (3Z)-3,7-dimethylocta-1,3,6-triene (Z)-β-ocimene 3338-55-4 CC(C)=CC\C=C(\C)C=C InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8- IHPKGUQCSIINRJ-NTMALXAHSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Alkatrienes Branched unsaturated hydrocarbons Unsaturated aliphatic hydrocarbons Acyclic monoterpenoid Acyclic olefin Aliphatic acyclic compound Alkatriene Branched unsaturated hydrocarbon Hydrocarbon Olefin Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Acyclic monoterpenoids monoterpene melting_point 50 °C Wikipedia boiling_point 100 °C at 70 mmHg Wikipedia logp 4.30 ALOGPS logs -2.91 ALOGPS logp 3.48 ChemAxon iupac (3Z)-3,7-dimethylocta-1,3,6-triene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)=CC\C=C(\C)C=C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7-8H,1,6H2,2-4H3/b10-8- ChemAxon inchikey IHPKGUQCSIINRJ-NTMALXAHSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 49.45 ChemAxon polarizability 17.18 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001462 4478390 5320250 C00000843 CPD-4903 87574 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:29:35 UTC 2020-07-24 23:30:06 UTC CDB000298 perillene Perillene, also known as perillen, belongs to the class of organic compounds known as monoterpenes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Perillene also belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Perillene is a neutral, hydrophobic molecule that is insoluble in water. Perillene exists as a clear, colorless oil and has a woody, flowery, citrus aroma or taste. Perillene has been found in several plants and spices including ginger and oregano. It has also been found in the essential oils of other plants, such as Perilla ocimoides (PMID: 17269047), Kenyan Valencia (Citrus sinensis), Australian finger lime (Citrus australasica) peel oil, Neroli (Citrus aurantium) (PMID: 30723488) and Boswellia sacra (PMID: 18830149). Perillene is one of more than 140 monoterpenes that are known in cannabis plants (PMID: 6991645), and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. 3-(4-Methyl-3-pentenyl)furan Perillen C10H14O 150.22 150.1045 3-(4-methylpent-3-en-1-yl)furan 3-(4-methylpent-3-en-1-yl)furan 539-52-6 CC(C)=CCCC1=COC=C1 InChI=1S/C10H14O/c1-9(2)4-3-5-10-6-7-11-8-10/h4,6-8H,3,5H2,1-2H3 XNGKCOFXDHYSGR-UHFFFAOYSA-N belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Heteroaromatic compounds Organic compounds Organoheterocyclic compounds Heteroaromatic compounds Aromatic heteromonocyclic compounds Furans Hydrocarbon derivatives Organooxygen compounds Oxacyclic compounds Aromatic heteromonocyclic compound Furan Heteroaromatic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle furans monoterpenoid boiling_point 186 °C Wikipedia logp 3.78 ALOGPS logs -3.13 ALOGPS logp 3.29 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac 3-(4-methylpent-3-en-1-yl)furan ChemAxon average_mass 150.22 ChemAxon mono_mass 150.1045 ChemAxon smiles CC(C)=CCCC1=COC=C1 ChemAxon formula C10H14O ChemAxon inchi InChI=1S/C10H14O/c1-9(2)4-3-5-10-6-7-11-8-10/h4,6-8H,3,5H2,1-2H3 ChemAxon inchikey XNGKCOFXDHYSGR-UHFFFAOYSA-N ChemAxon polar_surface_area 13.14 ChemAxon refractivity 47.42 ChemAxon polarizability 18.01 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB007821 68316 74039 Perillene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Misra LN, Husain A: The Essential Oil of Perilla ocimoides: A Rich Source of Rosefuran. Planta Med. 1987 Aug;53(4):379-80. doi: 10.1055/s-2006-962743. 17269047 Dala-Paula BM, Plotto A, Bai J, Manthey JA, Baldwin EA, Ferrarezi RS, Gloria MBA: Effect of Huanglongbing or Greening Disease on Orange Juice Quality, a Review. Front Plant Sci. 2019 Jan 22;9:1976. doi: 10.3389/fpls.2018.01976. eCollection 2018. 30723488 Al-Harrasi A, Al-Saidi S: Phytochemical analysis of the essential oil from botanically certified oleogum resin of Boswellia sacra (Omani Luban). Molecules. 2008 Sep 16;13(9):2181-9. doi: 10.3390/molecules13092181. 18830149 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:38 UTC 2020-08-04 22:28:16 UTC CDB000299 Methallylbenzene 3-phenyl-2-mehtyl-prop-1-ene, also known as Methallylbenzene, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety, which consists of a propene substituent bound to a phenyl group. Biochemically, Methallylbenzene is a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Methallylbenzene is a hydrophobic, neutral molecule that is insoluble in water. It is one of more than 140 naturally occurring terpenes found in cannabis plants (PMID:6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita C10H12 132.21 132.0939 (2-methylprop-2-en-1-yl)benzene (2-methylprop-2-en-1-yl)benzene 3290-53-7 CC(=C)CC1=CC=CC=C1 InChI=1S/C10H12/c1-9(2)8-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3 MXTNFIYGTWARIN-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenylpropanes Organic compounds Benzenoids Benzene and substituted derivatives Phenylpropanes Aromatic homomonocyclic compounds Aromatic hydrocarbons Branched unsaturated hydrocarbons Cyclic olefins Aromatic homomonocyclic compound Aromatic hydrocarbon Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Phenylpropane Unsaturated hydrocarbon logp 3.60 ALOGPS logs -2.82 ALOGPS logp 3.32 ChemAxon iupac (2-methylprop-2-en-1-yl)benzene ChemAxon average_mass 132.21 ChemAxon mono_mass 132.0939 ChemAxon smiles CC(=C)CC1=CC=CC=C1 ChemAxon formula C10H12 ChemAxon inchi InChI=1S/C10H12/c1-9(2)8-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3 ChemAxon inchikey MXTNFIYGTWARIN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.63 ChemAxon polarizability 15.84 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 18687 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:40 UTC 2020-08-04 22:28:16 UTC CDB000300 α-pinene Alpha-Pinene, also known as 2-pinene or acintene A, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-pinene is considered to be an isoprenoid lipid molecule. There are two isomers of alpha-Pinene: (‚àí)-Œ±-pinene and (+)-Œ±-pinene. The (‚àí)-Œ±-pinene isomer is more common in European pines, whereas the (+)-Œ±-isomer is more common in North America. alpha-Pinene is a neutral, hydrophobic molecule, practically insoluble in water. It exists as a clear, colorless oil. Alpha-pinene has a woody, camphoreous, piney or turpentine-like odor and a spicy, woody or herbal taste. It is widely used as a flavor and a fragrance additive and has one of the lowest boiling points of all monoterpenes. Industrially, Œ±-pinene is largely used as starting material for the synthesis of terpineol, camphor, borneol and terpene resin, synthetic perfumes and resins, medicines and other synthetic organic chemicals. Alpha-pinene is found naturally in the essential oils and resins of many coniferous tree species, notably the pine (where it gets its name) as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). It is also found in the essential oil of rosemary, eucalyptus oil and orange peel oil. Œ±-Pinene is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. Œ±-Pinene, in particular, contributes significantly to many of the varied, distinct, and unique odor profiles of different¬†cannabis strains, varieties and¬†cultivars. Monoterpenes, of which Œ±-pinene is one of the principal species, are emitted in substantial amounts by vegetation. In the atmosphere Œ±-pinene undergoes reactions with ozone, hydroxyl radicals and NO3 radicals to produce several compounds including: pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid (PMID: 20017184). Œ±-Pinene exhibits a wide range of physiological or drug like effects. There are well-substantiated claims that has anticoagulant, antitumor, antimicrobial, antimalarial, antioxidant, anti-inflammatory, anti-Leishmania, analgesic, gastroprotective, anxiolytic, cytoprotective, anticonvulsant, and neuroprotective effects (PMID: 31739596). Œ±-Pinene exhibits activity as an acetylcholinesterase inhibitor, which may aid in memory retention. Œ±-Pinene, in particular, is thought to reduce the memory deficits commonly reported as a side-effect of THC consumption (PMID: 31739596). Œ±-Pinene is a positive modulator of GABAA receptors and binds to the benzodiazepine binding site of the GABAA receptor (PMID: 31739596). (+)-Œ±-Pinene also binds to Cytochrome P450 2B6 and is a potent inhibitor of this enzyme (PMID: 23786449). (+)-3,6,6-TRIMETHYLBICYCLO[3.1.1]hept-2-ene (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene (1R,5R)-alpha-Pinene alpha-Pinene(dextro) (1R,5R)-a-Pinene (1R,5R)-Α-pinene a-Pinene(dextro) Α-pinene(dextro) (+)-a-Pinene (+)-Α-pinene (+)-(1R)-alpha-Pinene (+)-(1R)-Α-pinene (+)-(1R,5R)-alpha-Pinene (+)-(1R,5R)-Α-pinene (+)-2-Pinene (1R)-(+)-alpha-Pinene (1R)-(+)-Α-pinene (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene (1R)-alpha-Pinene (1R)-Α-pinene (1R,5R)-(+)-alpha-Pinene (1R,5R)-(+)-Α-pinene (R)-(+)-alpha-Pinene (R)-(+)-Α-pinene (±)-2-pinene (±)-alpha-pinene (±)-α-pinene 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene 2-Pinene alpha-Pinene Α-pinene (+)-alpha-Pinene (1R,5R)-(+)-2-Pinene d-alpha-Pinene d-α-Pinene C10H16 136.23 136.1252 (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene (+)-α-pinene 7785-70-8 CC1=CC[C@@H]2C[C@H]1C2(C)C InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 GRWFGVWFFZKLTI-RKDXNWHRSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Pinane monoterpenoid Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bicyclic monoterpenoids Bicyclic monoterpenoids Cyclic monoterpenes alpha-pinene logp 4.44 GRIFFIN,S ET AL. (1999) melting_point -62 °C boiling_point 155 to 156 °C Wikipedia logp 3.66 ALOGPS logs -2.94 ALOGPS logp 2.8 ChemAxon iupac (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC1=CC[C@@H]2C[C@H]1C2(C)C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 ChemAxon inchikey GRWFGVWFFZKLTI-RKDXNWHRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.72 ChemAxon polarizability 17.22 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013765 82227 74205 C06306 28261 CPD-8754 C00034999 Alpha-Pinene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Neuenschwander U, Guignard F, Hermans I: Mechanism of the aerobic oxidation of alpha-pinene. ChemSusChem. 2010;3(1):75-84. doi: 10.1002/cssc.200900228. 20017184 Salehi B, Upadhyay S, Erdogan Orhan I, Kumar Jugran A, L D Jayaweera S, A Dias D, Sharopov F, Taheri Y, Martins N, Baghalpour N, Cho WC, Sharifi-Rad J: Therapeutic Potential of alpha- and beta-Pinene: A Miracle Gift of Nature. Biomolecules. 2019 Nov 14;9(11). pii: biom9110738. doi: 10.3390/biom9110738. 31739596 Wilderman PR, Shah MB, Jang HH, Stout CD, Halpert JR: Structural and thermodynamic basis of (+)-alpha-pinene binding to human cytochrome P450 2B6. J Am Chem Soc. 2013 Jul 17;135(28):10433-40. doi: 10.1021/ja403042k. Epub 2013 Jul 3. 23786449 1.0 2020-03-19 00:29:45 UTC 2020-08-04 22:28:16 UTC CDB000301 piperitone oxide Piperitone oxide is an oxidized derivative of Piperitone. It belongs to the class of organic compounds known cyclic monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Piperitone oxide exists as two isomers, cis-Piperitone oxide and trans-Piperitone oxide. It is a colorless to pale yellow clear liquid that is neutral, hydrophobic and essentially insoluble in water. Piperitone oxide can be found in cornmint, orange mint, peppermint, and spearmint, which makes piperitone oxide a potential biomarker for the consumption of these food products. It has also been detected in the essential oils of other mint species, such as apple mint (Mentha suaveolens) (PMID: 25985361). Piperitone oxide has also been detected in Cannabis sativa plants (PMID: 6991645). It is one of more than 140 terpenoids found in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. C10H16O2 168.24 168.115 (1S,3R,6S)-6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one (1S,3R,6S)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-2-one 4713-38-6 CC(C)[C@H]1CC[C@]2(C)O[C@@H]2C1=O InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1 IAFONZHDZMCORS-QNSHHTMESA-N belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Oxepanes Organic compounds Organoheterocyclic compounds Oxepanes Aliphatic heteropolycyclic compounds Aldehydes Dialkyl ethers Epoxides Hydrocarbon derivatives Ketones Organic oxides Oxacyclic compounds Aldehyde Aliphatic heteropolycyclic compound Carbonyl group Dialkyl ether Ether Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Oxepane Oxirane logp 1.96 ALOGPS logs -1.93 ALOGPS logp 2.26 ChemAxon pka_strongest_acidic 19.7 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac (1S,3R,6S)-6-methyl-3-(propan-2-yl)-7-oxabicyclo[4.1.0]heptan-2-one ChemAxon average_mass 168.24 ChemAxon mono_mass 168.115 ChemAxon smiles CC(C)[C@H]1CC[C@]2(C)O[C@@H]2C1=O ChemAxon formula C10H16O2 ChemAxon inchi InChI=1S/C10H16O2/c1-6(2)7-4-5-10(3)9(12-10)8(7)11/h6-7,9H,4-5H2,1-3H3/t7-,9-,10+/m1/s1 ChemAxon inchikey IAFONZHDZMCORS-QNSHHTMESA-N ChemAxon polar_surface_area 29.6 ChemAxon refractivity 45.95 ChemAxon polarizability 18.97 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6430800 Bozovic M, Pirolli A, Ragno R: Mentha suaveolens Ehrh. (Lamiaceae) Essential Oil and Its Main Constituent Piperitenone Oxide: Biological Activities and Chemistry. Molecules. 2015 May 13;20(5):8605-33. doi: 10.3390/molecules20058605. 25985361 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:49 UTC 2020-08-04 22:28:16 UTC CDB000302 trans-Sabinene hydrate Trans-Sabinene hydrate, also known as trans-4-thujanol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Trans-Sabinene hydrate is a neutral, hydrophobic molecule that is practically insoluble in water. It has a woody, balsamic odor. It occurs naturally in a wide number of plants and plant oils including lemon, lime, grapefruit, blood orange, mandarin orange, orange peel, rosemary, nutmeg, pot marjoram, common oregano, and mentha (mint), which makes (+)-trans-sabinene hydrate a potential biomarker for the consumption of these food products. Trans-Sabinene hydrate is one of the terpenoids that has been identified in cannabis plants only in trace amounts (PMID: 6991645). It is one of more than 140 terpenoids found in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. (+)-trans-Sabinene hydric acid C10H18O 154.25 154.1358 (1S,2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol (1S,2S,5R)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol CC(C)[C@@]12C[C@@H]1[C@@](C)(O)CC2 InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1 KXSDPILWMGFJMM-KXUCPTDWSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol Thujane monoterpenoid logp 2.12 ALOGPS logs -2.28 ALOGPS logp 1.89 ChemAxon pka_strongest_acidic 19.13 ChemAxon pka_strongest_basic -0.99 ChemAxon iupac (1S,2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)[C@@]12C[C@@H]1[C@@](C)(O)CC2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1 ChemAxon inchikey KXSDPILWMGFJMM-KXUCPTDWSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.55 ChemAxon polarizability 18.66 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001454 11228920 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:53 UTC 2020-08-04 22:28:16 UTC CDB000303 alpha-Terpinene-4-ol Œ±-Terpinene-4-ol, also known as terpinen-4-ol, 1-para-menthen-4-ol or p-Menth-1-en-4-ol or 4-carvomenthenol, is an isomer of terpineol. It belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Œ±-Terpinene-4-ol is a hydrophobic, largely neutral molecule that is essentially insoluble in water. It has a peppery, spicy, musty, citrus odor and a cooling woody or spicy taste. Œ±-Terpinene-4-ol is widely used as a flavoring agent and as a masking agent in cosmetics. Œ±-Terpinene-4-ol is a natural product that can be found in a number of plants, such as allspice, anise, apple, basil, cardamom, cinnamon and Melaleuca alternifolia (also called tea tree) and is the main bioactive component of tea tree oil (PMID 22083482). Œ±-Terpinene-4-ol is also one of the monoterpenes found in cannabis plants (PMID: 6991645). Terpinen-4-ol is a potent bactericidal agent that also possess antifungal properties. In particular, it has shown in vitro activity against Staphylococcus aureus and C. albicans (PMID: 27275783). It has also been shown that combining this natural substance and conventional drugs may help treat resistant yeast and bacterial infections. Several studies have suggested that terpinen-4-ol induces antitumor effects by selectively causing necrotic cell death and cell-cycle arrest in melanoma cell lines, or by triggering caspase-dependent apoptosis in human melanoma cells (PMID: 27275783). (+)-Terpinen-4-ol (S)-(+)-p-Menth-1-en-4-ol (S)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol S-4-Carvomenthenol S-Origanol C10H18O 154.25 154.1358 (1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol (1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol 2438-10-0 CC(C)[C@]1(O)CCC(C)=CC1 InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1 WRYLYDPHFGVWKC-SNVBAGLBSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Monocyclic monoterpenoids Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Hydrocarbon derivative Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Tertiary alcohol logp 2.81 ALOGPS logs -1.79 ALOGPS logp 2.33 ChemAxon pka_strongest_acidic 20 ChemAxon pka_strongest_basic -0.61 ChemAxon iupac (1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)[C@]1(O)CCC(C)=CC1 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1 ChemAxon inchikey WRYLYDPHFGVWKC-SNVBAGLBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 48.31 ChemAxon polarizability 18.7 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014586 2006320 2724161 C00010928 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Hammer KA, Carson CF, Riley TV: Effects of Melaleuca alternifolia (tea tree) essential oil and the major monoterpene component terpinen-4-ol on the development of single- and multistep antibiotic resistance and antimicrobial susceptibility. Antimicrob Agents Chemother. 2012 Feb;56(2):909-15. doi: 10.1128/AAC.05741-11. Epub 2011 Nov 14. 22083482 Shapira S, Pleban S, Kazanov D, Tirosh P, Arber N: Terpinen-4-ol: A Novel and Promising Therapeutic Agent for Human Gastrointestinal Cancers. PLoS One. 2016 Jun 8;11(6):e0156540. doi: 10.1371/journal.pone.0156540. eCollection 2016. 27275783 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Su CW, Tighe S, Sheha H, Cheng AMS, Tseng SCG: Safety and efficacy of 4-terpineol against microorganisms associated with blepharitis and common ocular diseases. BMJ Open Ophthalmol. 2018 Jun 4;3(1):e000094. doi: 10.1136/bmjophth-2017-000094. eCollection 2018. 30123842 Ramage G, Milligan S, Lappin DF, Sherry L, Sweeney P, Williams C, Bagg J, Culshaw S: Antifungal, cytotoxic, and immunomodulatory properties of tea tree oil and its derivative components: potential role in management of oral candidosis in cancer patients. Front Microbiol. 2012 Jun 18;3:220. doi: 10.3389/fmicb.2012.00220. eCollection 2012. 22719736 Tighe S, Gao YY, Tseng SC: Terpinen-4-ol is the Most Active Ingredient of Tea Tree Oil to Kill Demodex Mites. Transl Vis Sci Technol. 2013 Nov;2(7):2. doi: 10.1167/tvst.2.7.2. Epub 2013 Nov 13. 24349880 1.0 2020-03-19 00:29:55 UTC 2020-08-04 22:28:16 UTC CDB000304 Thujyl alcohol Thujyl alcohol, also known as 3-thujol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Thujyl alcohol can also be formally classified as a bicyclic alcohol. Thujyl alcohol is a neutral, hydrophobic molecule that is poorly soluble in water. Thujyl alcohol has a camphoreous, minty odor. It is found naturally in a number of plants including ginger, cedar and wormowood. Thujyl alcohol is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. C10H18O 154.25 154.1358 (1S,3R,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol (1S,3R,4S,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-ol 513-23-5 CC(C)[C@@]12C[C@@H]1[C@H](C)[C@H](O)C2 InChI=1S/C10H18O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-9,11H,4-5H2,1-3H3/t7-,8+,9+,10-/m0/s1 DZVXRFMREAADPP-JLIMGVALSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Thujane monoterpenoid logp 1.59 ALOGPS logs -2.25 ALOGPS logp 1.9 ChemAxon pka_strongest_acidic 18.66 ChemAxon pka_strongest_basic -1.2 ChemAxon iupac (1S,3R,4S,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC(C)[C@@]12C[C@@H]1[C@H](C)[C@H](O)C2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-9,11H,4-5H2,1-3H3/t7-,8+,9+,10-/m0/s1 ChemAxon inchikey DZVXRFMREAADPP-JLIMGVALSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.46 ChemAxon polarizability 18.74 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12304605 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:29:59 UTC 2020-08-04 22:28:16 UTC CDB000305 allo-Aromadendrene Alloaromadendrene or Aromadendrene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpe. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Aromadendrene is possibly neutral Aromadendrene is a woody tasting compound. Alloaromadendrene is a sesquiterpene found in cannabis plants only in trace amounts (PMID: 6991645). In one particular study, Alloaromadendrene is found in the essential oil of indigenous cinnamon. It exhibits antioxidant activity (PMID: 24918691). C15H24 204.36 204.1878 (1aS,4aS,7R,7aR,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene (1aS,4aS,7R,7aR,7bS)-1,1,7-trimethyl-4-methylidene-octahydro-1aH-cyclopropa[e]azulene C[C@@H]1CC[C@H]2[C@@H]1[C@H]1[C@H](CCC2=C)C1(C)C InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12+,13-,14-/m1/s1 ITYNGVSTWVVPIC-RKQHYHRCSA-N belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5,10-cycloaromadendrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Guaianes Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons 5,10-cycloaromadendrane sesquiterpenoid Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Guaiane sesquiterpenoid Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 3.70 ALOGPS logs -4.94 ALOGPS logp 4.15 ChemAxon iupac (1aS,4aS,7R,7aR,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CC[C@H]2[C@@H]1[C@H]1[C@H](CCC2=C)C1(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12+,13-,14-/m1/s1 ChemAxon inchikey ITYNGVSTWVVPIC-RKQHYHRCSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.7 ChemAxon polarizability 25.75 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 94249463 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Yu CW, Li WH, Hsu FL, Yen PL, Chang ST, Liao VH: Essential oil alloaromadendrene from mixed-type Cinnamomum osmophloeum leaves prolongs the lifespan in Caenorhabditis elegans. J Agric Food Chem. 2014 Jul 2;62(26):6159-65. doi: 10.1021/jf500417y. Epub 2014 Jun 23. 24918691 1.0 2020-03-19 00:30:03 UTC 2020-09-11 20:08:30 UTC CDB000306 α-trans-bergamotene Œ±-Trans-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. Œ±-Trans-bergamotene is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it synthesized via multiple isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are four known Bergamotene isomers including Œ±-cis-, Œ±-trans-, Œ≤-cis- and Œ≤-trans-bergamotene. Œ±-trans-bergamotene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a clear, greenish oil that has a woody or warm tea-like odor. It is found in the fruits and essential oils of anise, basil, cumin, carrot, bergamot, lime, lemon, cottonseed, nutmeg, black pepper and kumquat. Œ±-trans-bergamotene is also found in the essential oils of plants such as tobacco (PMID:28434859) and cannabis (PMID:6991645). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the insect herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295). More specifically, the tobacco plant emits Œ±-trans-bergamotene from its flowers at night to attract the tobacco hawk moth (Manduca sexta) as a pollinator; however, during the day the leaves produce Œ±-trans-bergamotene to lure predatory insects to feed on any larvae and eggs that the pollinator may have produced (PMID: 28434859). (-)-trans-alpha-Bergamotene (-)-trans-a-Bergamotene (-)-trans-Α-bergamotene (-)-exo-a-Bergamotene (-)-exo-Α-bergamotene alpha-Bergamotene cis-alpha-Bergamotene C15H24 204.36 204.1878 (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene (-)-trans-α-bergamotene 13474-59-4 CC(C)=CCC[C@]1(C)[C@@H]2C[C@H]1C(C)=CC2 InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m0/s1 YMBFCQPIMVLNIU-SOUVJXGZSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Pinane monoterpenoid Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon alpha-bergamotene logp 5.91 ALOGPS logs -4.48 ALOGPS logp 4.46 ChemAxon iupac (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC[C@]1(C)[C@@H]2C[C@H]1C(C)=CC2 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m0/s1 ChemAxon inchikey YMBFCQPIMVLNIU-SOUVJXGZSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.52 ChemAxon polarizability 26.45 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 62756 6429302 Zhou W, Kugler A, McGale E, Haverkamp A, Knaden M, Guo H, Beran F, Yon F, Li R, Lackus N, Kollner TG, Bing J, Schuman MC, Hansson BS, Kessler D, Baldwin IT, Xu S: Tissue-Specific Emission of (E)-alpha-Bergamotene Helps Resolve the Dilemma When Pollinators Are Also Herbivores. Curr Biol. 2017 May 8;27(9):1336-1341. doi: 10.1016/j.cub.2017.03.017. Epub 2017 Apr 20. 28434859 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schnee C, Kollner TG, Held M, Turlings TC, Gershenzon J, Degenhardt J: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc Natl Acad Sci U S A. 2006 Jan 24;103(4):1129-34. doi: 10.1073/pnas.0508027103. Epub 2006 Jan 17. 16418295 1.0 2020-03-19 00:30:08 UTC 2020-07-31 20:34:13 UTC CDB000308 alpha-Caryophyllene alcohol Alpha-Caryophyllene alcohol also called alpha-Caryophyllenol is a derivative of alpha-Caryophyllene. It belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a bicyclic sesquiterpenoid as it is synthesized via multiple isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Caryophyllene alcohol exists as a white, crystalline powder. It is a neutral, hydrophobic molecule that is insoluble in water. Alpha-Caryophyllene is an approved food additive and has a woody, spicy or earthy aroma. It is a naturally occurring substance found in a number of foods or plants including black pepper, allspice and guava fruit. It was first synthesized by E.J. Corey in 1964 ( https://doi.org/10.1021/ja00952a036). Alpha-Caryophyllene alcohol is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. C15H26O 222.37 222.1984 (1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol (1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol 4586-22-5 CC1(C)C[C@H]2[C@@H](C1)[C@]1(C)CCC[C@@]2(C)[C@@H]1O InChI=1S/C15H26O/c1-13(2)8-10-11(9-13)15(4)7-5-6-14(10,3)12(15)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14+,15- MJYUBUQHKCAJQR-LYOXDTQASA-N belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Cyclic alcohols and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homopolycyclic compounds Hydrocarbon derivatives Secondary alcohols Aliphatic homopolycyclic compound Cyclic alcohol Hydrocarbon derivative Secondary alcohol logp 3.47 ALOGPS logs -4.04 ALOGPS logp 3.44 ChemAxon pka_strongest_basic -0.3 ChemAxon iupac (1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC1(C)C[C@H]2[C@@H](C1)[C@]1(C)CCC[C@@]2(C)[C@@H]1O ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-13(2)8-10-11(9-13)15(4)7-5-6-14(10,3)12(15)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14+,15- ChemAxon inchikey MJYUBUQHKCAJQR-LYOXDTQASA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 66.13 ChemAxon polarizability 27.13 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:30:12 UTC 2020-09-11 20:08:29 UTC CDB000309 gamma-elemene Gamma-Elemene, also known as g-elemene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. More formally, gamma-elemene is a cyclohexane substituted at positions 1, 1, 2, and 4 by methyl, vinyl, isopropenyl and isopropylidene groups, respectively. There are four known elemene isomers including Œ±-, Œ≤-, Œ≥-, and Œ¥-elemene. The elemenes contribute to the floral aromas of some plants and are used as pheromones by some insects. Gamma-elemene is found in many essential plant oils including wormwood leaf oil, peppermint oil, pepper tree leaf oil, parsley leaf oil, orange peel oil, lime oil, juniper berry oil, hinoki leaf oil, angelica root oil, and angelica seed oil. Gamma-elemene is also one of the many sesquiterpenes found in cannabis plants (PMID: 6991645). Gamma-elemene has been shown to exhibit good insecticidal activity against the crop pest Spodoptera litura (tobacco cutworm or cotton leafworm) and could be useful as an eco-friendly biopesticide (PMID:28634795). (+)-gamma-Elemene (+)-g-Elemene (+)-Γ-elemene g-Elemene Γ-elemene C15H24 204.36 204.1878 (1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane (1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1 BQSLMQNYHVFRDT-LSDHHAIUSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.09 ALOGPS logs -4.35 ALOGPS logp 4.64 ChemAxon iupac (1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1 ChemAxon inchikey BQSLMQNYHVFRDT-LSDHHAIUSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 69.03 ChemAxon polarizability 25.8 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004787 6432312 132656 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Benelli G, Govindarajan M, AlSalhi MS, Devanesan S, Maggi F: High toxicity of camphene and gamma-elemene from Wedelia prostrata essential oil against larvae of Spodoptera litura (Lepidoptera: Noctuidae). Environ Sci Pollut Res Int. 2018 Apr;25(11):10383-10391. doi: 10.1007/s11356-017-9490-7. Epub 2017 Jun 20. 28634795 1.0 2020-03-19 00:30:16 UTC 2020-08-04 22:28:16 UTC CDB000310 (z)-beta-Farnesen Œ≤-Farnesene, also known as (Z)-Œ≤-farnesene or Œ≤-cis-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ≤-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. beta-Farnesene exists as two stereoisomers about the geometry of its central double bond. Œ≤-Farnesene has one naturally occurring isomer. The E isomer is a constituent of various essential oils. It is also released by aphids as an alarm pheremone upon death to warn away other aphids. Several plants, including potato species, have been shown to emit this terpenoid as a natural insect repellent. Œ≤-Farnesene is a sweet, citrus, and green tasting compound. Œ≤-Farnesene has been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645; PMID: 26657499). It is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). (6Z)-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene (Z)-beta-Farnesene beta-(Z)-Farnesene beta-cis-Farnesene (Z)-b-Farnesene (Z)-Β-farnesene b-(Z)-Farnesene Β-(Z)-farnesene b-cis-Farnesene Β-cis-farnesene b-Farnesene Β-farnesene 7,11-Dimethyl-3-methylene-1,6,10-dodecatriene cis-b-Farnesene cis-Β-farnesene beta-Farnesene C15H24 204.35 204.1878 (6Z)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene (Z)-β-farnesene 28973-97-9 CC(C)=CCC\C(C)=C/CCC(=C)C=C InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12- JSNRRGGBADWTMC-QINSGFPZSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Alkatetraenes Branched unsaturated hydrocarbons Unsaturated aliphatic hydrocarbons Acyclic olefin Aliphatic acyclic compound Alkatetraene Branched unsaturated hydrocarbon Farsesane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon beta-farnesene logp 5.70 ALOGPS logs -4.78 ALOGPS logp 5.2 ChemAxon iupac (6Z)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC\C(C)=C/CCC(=C)C=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12- ChemAxon inchikey JSNRRGGBADWTMC-QINSGFPZSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 72.18 ChemAxon polarizability 26.75 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4476201 FDB014702 5317319 39242 C00003131 Farnesene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:30:18 UTC 2020-08-04 22:28:16 UTC CDB000311 trans-trans-alpha-Farnesene Trans-trans-alpha-Farnesene, also known as (3E,6E)-alpha-Farnesene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. Œ±-Farnesene and Œ≤-Farnesene are isomers, differing by the location of one double bond. Œ≤-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while¬†Œ±-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. There are four known Alpha-farnesene stereoisomers which differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). (3E,6E)-alpha-Farnesene is one of the 4 isomers of Alpha-farnesene and is the most common isomer, Trans-trans-alpha-Farnesene is a hydrophobic, neutral molecule that is not water soluble. It has a woody, bergamot, green and citrus like aroma and a fresh, green, fruity taste. Trans-trans-alpha-Farnesene is used as a flavoring and perfuming agent. It is found in the coating of apples, and other fruits, and it is responsible for the characteristic green apple odour (doi:10.1038/2101260a0). (3E,6E)-alpha-Farnesene is found within a few different foods, such as gingers, cottonseeds, common oregano and sweet oranges. (3E,6E)-alpha-Farnesene has also been detected, but not quantified in, several different foods, such as apples, pears, spearmints, guava, and carrots. Trans-trans-alpha-farnesene is one of several sesquiterpenes that are found in cannabis plants (PMID: 6991645).¬†It is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). (E,E)-Farnesene trans-Farnesene 3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraene alpha-trans,trans-Farnesene trans,trans-alpha-Farnesene (3E,6E)-a-Farnesene (3E,6E)-α-Farnesene alpha-Farnesene (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene (3E,6E)-alpha-Farnesene (E,E)-alpha-Farnesene (E,E)-α-Farnesene 3,7,11-Trimethyl-1,3,6,10-dodecatetraene Farnesene trans,trans-α-Farnesene trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene trans-alpha-Farnesene trans-α-Farnesene α-Farnesene C15H24 204.35 204.1878 (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene farnesene 502-61-4 CC(C)=CCC\C(C)=C\C\C=C(/C)C=C InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+ CXENHBSYCFFKJS-VDQVFBMKSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Alkatetraenes Branched unsaturated hydrocarbons Unsaturated aliphatic hydrocarbons Acyclic olefin Aliphatic acyclic compound Alkatetraene Branched unsaturated hydrocarbon Farsesane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Farnesenes alpha-farnesene logp 5.70 ALOGPS logs -4.60 ALOGPS logp 5.14 ChemAxon iupac (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC\C(C)=C\C\C=C(/C)C=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+ ChemAxon inchikey CXENHBSYCFFKJS-VDQVFBMKSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 73.25 ChemAxon polarizability 26.86 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014895 5281516 4444849 C09665 10280 C00003130 CPD-8764 Farnesene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:30:21 UTC 2020-07-24 23:30:15 UTC CDB000312 farnesyl acetone Farnesylacetone or (5E,9E)-Farnesylacetone, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. It is formally classified as an acyclic ketone although it is biochemically a diterpenoid as it is synthesized via isoprene units. Diterpenoids are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Four different Farnesylacetone isomers exist ((5E,9E)-Farnesylacetone, (5E,9Z)-Farnesylacetone, (5Z,9E)-Farnesylacetone, and (5Z,9Z)-Farnesylacetone) with the most common being (5E,9E)-Farnesylacetone. Farnesylacetone is a hydrophobic, neutral molecule that insoluble in water. It is used as a food additive and a cosmetic/perfuming agent. It has a fruity, floral, wine-like odor and is often used as a floral base for fruit and floral fragrances. Farnesylacetone is found naturally in a number of foods and plants including tomatoes, watermelon, yarrow and mushrooms. Farnesylacetone is also one of more than 140 terpenes that are found in cannabis plants (PMID: 6991645). Farnesylacetone, (e,e)-isomer C18H30O 262.44 262.2297 6,10,14-trimethylpentadeca-5,9,13-trien-2-one 6,10,14-trimethylpentadeca-5,9,13-trien-2-one 762-29-8 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O InChI=1S/C18H30O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h9,11,13H,6-8,10,12,14H2,1-5H3 LTUMRKDLVGQMJU-UHFFFAOYSA-N belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Acyclic diterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Diterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Ketones Organic oxides Acyclic diterpenoid Aliphatic acyclic compound Carbonyl group Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound a terpenoid derivative logp 6.20 ALOGPS logs -4.46 ALOGPS logp 5.34 ChemAxon pka_strongest_acidic 19.6 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac 6,10,14-trimethylpentadeca-5,9,13-trien-2-one ChemAxon average_mass 262.44 ChemAxon mono_mass 262.2297 ChemAxon smiles CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O ChemAxon formula C18H30O ChemAxon inchi InChI=1S/C18H30O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h9,11,13H,6-8,10,12,14H2,1-5H3 ChemAxon inchikey LTUMRKDLVGQMJU-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 87.63 ChemAxon polarizability 33.59 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 61206 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:30:25 UTC 2020-08-04 22:28:16 UTC CDB000313 alpha-Gurjunene Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil. Alpha-gurjunene is also one of more than 140 terpenes that are found in cannabis plants (PMID: 6991645). (-)-a-Gurjunene (-)-Α-gurjunene a-Gurjunene Α-gurjunene C15H24 204.36 204.1878 (1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,4H,4aH,5H,6H,7bH-cyclopropa[e]azulene (-)-α-gurjunene 489-40-7 C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1 SPCXZDDGSGTVAW-XIDUGBJDSA-N belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5,10-cycloaromadendrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons 5,10-cycloaromadendrane sesquiterpenoid Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon carbotricyclic compound sesquiterpene logp 4.45 ALOGPS logs -4.22 ALOGPS logp 4.04 ChemAxon iupac (1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,4H,4aH,5H,6H,7bH-cyclopropa[e]azulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1 ChemAxon inchikey SPCXZDDGSGTVAW-XIDUGBJDSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.5 ChemAxon polarizability 26.22 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 15560276 61699 C19734 CPD-12891 C00021227 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:30:28 UTC 2020-07-31 20:34:13 UTC CDB000314 alpha-Humulene epoxide I alpha-Humulene epoxide I, also known as alpha-humulene oxide I or humulene epoxide I, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms (one oxygen and two carbon atoms). alpha-Humulene epoxide I is an extremely weak basic (essentially neutral) compound (based on its pKa). alpha-Humulene epoxide I is also biochemically classified as a terpenoid. alpha-Humulene epoxide I is typically found in alcoholic beverages, especially beer. alpha-Humulene epoxide I is a constituent of hops, cannabis and wild ginger (Zingiber zerumbet) and has a characteristic herbal or “hoppy” fragrance. alpha-Humulene epoxide I is an oxidation product of humulene. Humulene is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds. Humulene is found in the flowering cone of the hops plant, Humulus lupulus, from which it derives its name as well as in the flowers of related plants such as cannabis. The concentration of humulene varies among different varieties of hops and cannabis but can be up to 40% of the essential oil. Multiple epoxides of humulene (such as alpha-humulene epoxide I and alpha-humulene epoxide II) are produced in the brewing process of beer or in the extraction of cannabis oils.  C15H24O 220.36 220.1827 (1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene (1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene C\C1=C\CC[C@]2(C)O[C@H]2CC(C)(C)\C=C\C1 InChI=1S/C15H24O/c1-12-7-5-9-14(2,3)11-13-15(4,16-13)10-6-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8-/t13-,15-/m0/s1 RKQDKXOBRXTSFS-MQTWWMRFSA-N belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Epoxides Organic compounds Organoheterocyclic compounds Epoxides Aliphatic heteropolycyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteropolycyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Oxirane logp 5.02 ALOGPS logs -4.45 ALOGPS logp 3.98 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1S,4Z,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-diene ChemAxon average_mass 220.36 ChemAxon mono_mass 220.1827 ChemAxon smiles C\C1=C\CC[C@]2(C)O[C@H]2CC(C)(C)\C=C\C1 ChemAxon formula C15H24O ChemAxon inchi InChI=1S/C15H24O/c1-12-7-5-9-14(2,3)11-13-15(4,16-13)10-6-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8-/t13-,15-/m0/s1 ChemAxon inchikey RKQDKXOBRXTSFS-MQTWWMRFSA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 70.31 ChemAxon polarizability 26.57 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-19 00:30:30 UTC 2020-08-04 22:28:16 UTC CDB000315 alpha-Humulene epoxide II Humulene epoxide II or humulene oxide II is an oxidized or epoxide form of alpha-humulene. Humulene is found in the flowering cone of the hops plant, Humulus lupulus, from which it derives its name as well as in the flowers of related plants such as cannabis. The concentration of humulene varies among different varieties of hops and cannabis but can be up to 40% of the essential oil. Humulene epoxide II belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms (one oxygen and two carbon atoms). Humulene epoxide II is also biochemically classified as a terpenoid or a monocyclic sesquiterpene (C15H24), which includes an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds. Humulene epoxide II exists as a clear, colorless liquid and essentially insoluble in water. Humulene epoxide II is found naturally in a number of plants and foods including allspice, hops, ginger, rosemary, and sage. Multiple epoxides of humulene (such as humulene epoxide I and humulene epoxide II) are produced in the brewing process of beer or in the extraction of cannabis oils. Humulene epoxide II is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645). Humulene epoxide II and other caryophyllene sesquiterpeines exhibit larvacidal activities against mosquito larvae (PMID: 20724962). C15H24O 220.36 220.1827 (1R,3Z,7Z,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (1R,3Z,7Z,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene C\C1=C\CC(C)(C)\C=C/C[C@@]2(C)O[C@@H]2CC1 InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5-,12-8-/t13-,15-/m1/s1 QTGAEXCCAPTGLB-SGRRRNBRSA-N belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Epoxides Organic compounds Organoheterocyclic compounds Epoxides Aliphatic heteropolycyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteropolycyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Oxirane logp 5.03 ALOGPS logs -4.43 ALOGPS logp 3.98 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1R,3Z,7Z,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene ChemAxon average_mass 220.36 ChemAxon mono_mass 220.1827 ChemAxon smiles C\C1=C\CC(C)(C)\C=C/C[C@@]2(C)O[C@@H]2CC1 ChemAxon formula C15H24O ChemAxon inchi InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5-,12-8-/t13-,15-/m1/s1 ChemAxon inchikey QTGAEXCCAPTGLB-SGRRRNBRSA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 70.31 ChemAxon polarizability 26.71 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 92476330 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Magalhaes LA, Lima Mda P, Marques MO, Facanali R, Pinto AC, Tadei WP: Chemical composition and larvicidal activity against Aedes aegypti larvae of essential oils from four Guarea species. Molecules. 2010 Aug 19;15(8):5734-41. doi: 10.3390/molecules15085734. 20724962 1.0 2020-03-19 00:30:34 UTC 2020-07-31 20:34:14 UTC CDB000316 Ledol Ledol belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a cyclic alcohol although it is biochemically a sesquiterpenoid as it is synthesized via isoprene units. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Ledol is a neutral, hydrophobic molecule that is essentially insoluble in water. Ledol is a naturally occurring sesquiterpene found in plants such as cannabis (PMID: 6991645), labrador tea (an herbal tea), eucalyptus, cloves, guava, peppermint, sage, thyme and in flowering plants (https://dx.doi.org/10.15482/USDA.ADC/1239279). It is known to have some toxic effects and if consumed in sufficiently high quantities can cause cramps, paralysis, and delirium (PMID: 25156477). Ledol also appears to have insecticidal or larvicidal activities (PMID: 25156477). C15H26O 222.37 222.1984 (1aS,1bS,2R,4aS,5R,7aR)-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-5-ol (+)-ledol 577-27-5 C[C@@H]1CC[C@H]2[C@@H]1[C@H]1[C@@H](CC[C@@]2(C)O)C1(C)C InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10+,11-,12-,13-,15-/m1/s1 AYXPYQRXGNDJFU-AOWZIMASSA-N belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5,10-cycloaromadendrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Guaianes Hydrocarbon derivatives Tertiary alcohols 5,10-cycloaromadendrane sesquiterpenoid Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Guaiane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol Sesquiterpenoids (C15) sesquiterpenoid logp 3.15 ALOGPS logs -4.72 ALOGPS logp 3.18 ChemAxon pka_strongest_basic -0.51 ChemAxon iupac (1aS,1bS,2R,4aS,5R,7aR)-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-5-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles C[C@@H]1CC[C@H]2[C@@H]1[C@H]1[C@@H](CC[C@@]2(C)O)C1(C)C ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10+,11-,12-,13-,15-/m1/s1 ChemAxon inchikey AYXPYQRXGNDJFU-AOWZIMASSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 66.6 ChemAxon polarizability 27.28 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015569 92812 C09698 C00003161 C00040741 Ledol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Dampc A, Luczkiewicz M: Labrador tea--the aromatic beverage and spice: a review of origin, processing and safety. J Sci Food Agric. 2015 Jun;95(8):1577-83. doi: 10.1002/jsfa.6889. Epub 2014 Sep 29. 25156477 1.0 2020-03-19 00:30:36 UTC 2020-07-07 15:57:23 UTC CDB000317 epi-beta-santalene Epi-beta-Santalene, also known as epi-santalene, belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Technically Epi-beta-santalene is a carbobicyclic compound that is bicyclo[2.2.1]heptane in which the hydrogens at position 3 are substituted by a methylidene group, while the 2-exo- and 2-endo- hydrogens are subsitituted by 2-methylpent-2-en-5-yl and methyl groups, respectively (the 1S,2R,4R enantiomer). Epi-beta-Santalene is a hydrophobic, neutral molecule that is insoluble in water. Epi-beta-Santalene is one of many terpenes that are found in cannabis plants (PMID: 6991645). It is also found in the essential oil of sandalwood which is a tropical tree (PMID: 24324844). Epi-b-santalene Epi-β-santalene C15H24 204.36 204.1878 (1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane (1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane CC(C)=CCC[C@@]1(C)[C@H]2CC[C@H](C2)C1=C InChI=1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14+,15-/m1/s1 PGBNIHXXFQBCPU-QLFBSQMISA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.56 ALOGPS logs -4.92 ALOGPS logp 4.52 ChemAxon iupac (1S,2S,4R)-2-methyl-3-methylidene-2-(4-methylpent-3-en-1-yl)bicyclo[2.2.1]heptane ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC[C@@]1(C)[C@H]2CC[C@H](C2)C1=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)6-5-9-15(4)12(3)13-7-8-14(15)10-13/h6,13-14H,3,5,7-10H2,1-2,4H3/t13-,14+,15-/m1/s1 ChemAxon inchikey PGBNIHXXFQBCPU-QLFBSQMISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.45 ChemAxon polarizability 26.12 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11106484 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Diaz-Chavez ML, Moniodis J, Madilao LL, Jancsik S, Keeling CI, Barbour EL, Ghisalberti EL, Plummer JA, Jones CG, Bohlmann J: Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol. PLoS One. 2013 Sep 18;8(9):e75053. doi: 10.1371/journal.pone.0075053. eCollection 2013. 24324844 1.0 2020-03-19 00:30:39 UTC 2020-09-11 20:08:31 UTC CDB000318 aplha-selinene Alpha-Selinene (Œ±-selinene) also known as selinene, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ±-Selinene is one of many terpenes that can be found in cannabis plants ( PMID: 31816756), together with the other three known Selinene isomers, Œ≤-, Œ≥-, and Œ¥- selinene. Selinenes have been detected in a variety of plant species, with Œ±- and Œ≤-selinene being the most frequent, while Œ≥-Selinene and Œ¥-selinene are less common. (2R-(2alpha,4Aalpha,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)naphthalene 2-Isopropenyl-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene Eudesma-3,11-diene (2R-(2a,4Aalpha,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)naphthalene (2R-(2Α,4aalpha,8abeta))-1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)naphthalene a-Selinene Α-selinene C15H24 204.36 204.1878 (2R,4aR,8aR)-4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene α-selinene 473-13-2 CC(=C)[C@@H]1CC[C@@]2(C)CCC=C(C)[C@@H]2C1 InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,13-14H,1,5,7-10H2,2-4H3/t13-,14+,15-/m1/s1 OZQAPQSEYFAMCY-QLFBSQMISA-N belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon selinene logp 5.86 ALOGPS logs -4.93 ALOGPS logp 4.52 ChemAxon iupac (2R,4aR,8aR)-4a,8-dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(=C)[C@@H]1CC[C@@]2(C)CCC=C(C)[C@@H]2C1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,13-14H,1,5,7-10H2,2-4H3/t13-,14+,15-/m1/s1 ChemAxon inchikey OZQAPQSEYFAMCY-QLFBSQMISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.45 ChemAxon polarizability 26.1 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59961 10856614 Alpha-selinene Selinene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. 31816756 1.0 2020-03-19 00:30:42 UTC 2020-07-07 15:57:25 UTC CDB000319 dihydrovomifoliol Dihydrovomifoliol, also known as 4,5-dihydrovomifoliol, belongs to the class of organic compounds known as sesquiterpenoids. While it is chemically classified as a cyclic alcohol it is biochemically a sesquiterpenoid as it is synthesized via multiple isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are several isomers of dihydrovomifoliol, including 4,5-Dihydrovomifoliol, 1,8-Dihydrovomifoliol and 7,8-Dihydrovomifoliol. 4,5-Dihydrovomifoliol appears to be the more common isomer in nature. 4,5-Dihydrovomifoliol is a neutral, hydrophobic molecule that is insoluble in water. It has been identified as an aroma constituent in nectarines (PMID: 14518956). It was first isolated from the leaves and stems of Dutch-grown hemp and identified as a cannabis constituent in 1976 (PMID: 6991645). C13H22O3 226.32 226.1569 (4S,5R)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,3,5-trimethylcyclohexan-1-one (4S,5R)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,3,5-trimethylcyclohexan-1-one C[C@@H](O)\C=C\[C@@]1(O)[C@H](C)CC(=O)CC1(C)C InChI=1S/C13H22O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-6,9-10,14,16H,7-8H2,1-4H3/b6-5+/t9-,10-,13-/m1/s1 IHDJYDVWNNFPHR-CHESLIBASA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Cyclic alcohols and derivatives Cyclic ketones Hydrocarbon derivatives Organic oxides Secondary alcohols Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Cyclofarsesane sesquiterpenoid Hydrocarbon derivative Ionone derivative Ketone Megastigmane sesquiterpenoid Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Sesquiterpenoid Tertiary alcohol logp 1.21 ALOGPS logs -1.87 ALOGPS logp 1.39 ChemAxon pka_strongest_acidic 13.77 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac (4S,5R)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,3,5-trimethylcyclohexan-1-one ChemAxon average_mass 226.32 ChemAxon mono_mass 226.1569 ChemAxon smiles C[C@@H](O)\C=C\[C@@]1(O)[C@H](C)CC(=O)CC1(C)C ChemAxon formula C13H22O3 ChemAxon inchi InChI=1S/C13H22O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-6,9-10,14,16H,7-8H2,1-4H3/b6-5+/t9-,10-,13-/m1/s1 ChemAxon inchikey IHDJYDVWNNFPHR-CHESLIBASA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 64.18 ChemAxon polarizability 25.3 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21630916 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Aubert C, Ambid C, Baumes R, Gunata Z: Investigation of bound aroma constituents of yellow-fleshed nectarines (Prunus persica L. Cv. Springbright). changes in bound aroma profile during maturation. J Agric Food Chem. 2003 Oct 8;51(21):6280-6. doi: 10.1021/jf034613h. 14518956 1.0 2020-03-19 00:30:45 UTC 2020-07-24 23:30:15 UTC CDB000320 dihydroactinidiolide Dihydroactinidiolide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Biochemically is a bicyclic monoterpenoid. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Dihydroactinidiolide is a neutral, hydrophobic compound that is not soluble in water. It exists as a yellow to brown solid or oil. It used as a food flavoring agent and has fruity, ripe apricot and woody aroma. Dihydroactinidiolide is a naturally occurring volatile terpene found in black tea, coffee, raspberries, strawberries, tomatoes, fenugreek, mangos, silver vine (Actinidia polygama), and tobacco. Dihydroactinidiolide is one of many terpenoids that are found in cannabis plants (PMID: 6991645). Dihydroactinidiolide also acts as a pheromone for a variety of insects, including the fire ant. In particular, it is one of the three components of the pheromone for queen recognition of red fire ant workers (J. Bricout et al., Helv. Chim. Acta 50, 1517 (1967)). It can be produced by photo-oxidation of carotenoid flavor compounds. C11H16O2 180.25 180.115 (7aR)-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one dihydroactinidiolide 17092-92-1 C[C@@]12CCCC(C)(C)C1=CC(=O)O2 InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3/t11-/m1/s1 IMKHDCBNRDRUEB-LLVKDONJSA-N belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Benzofurans Organic compounds Organoheterocyclic compounds Benzofurans Aliphatic heteropolycyclic compounds Butenolides Carbonyl compounds Enoate esters Hydrocarbon derivatives Lactones Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds 2-furanone Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Benzofuran Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dihydrofuran Enoate ester Hydrocarbon derivative Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle logp 3.28 ALOGPS logs -2.47 ALOGPS logp 2.57 ChemAxon pka_strongest_basic -6.8 ChemAxon iupac (7aR)-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one ChemAxon average_mass 180.25 ChemAxon mono_mass 180.115 ChemAxon smiles C[C@@]12CCCC(C)(C)C1=CC(=O)O2 ChemAxon formula C11H16O2 ChemAxon inchi InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3/t11-/m1/s1 ChemAxon inchikey IMKHDCBNRDRUEB-LLVKDONJSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 50.93 ChemAxon polarizability 19.89 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6432173 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:30:48 UTC 2020-08-04 22:28:16 UTC CDB000321 acetylcannabispirol Acetylcannabispirol is an acetylated derivative of cannabispiranol, which is derived from cannabispirone and cannabispirenone. It belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Acetylcannabispirol is also classified as a spiroindane compound. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. Spiroindane compounds are indane compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Acetylcannabispirol is neutral, hydrophobic molecule that is insoluble in water. Acetylcannabispirol is one of several spiroindane, noncannabinoid compounds that are known in cannabis plants (PMID: 6991645). It was first isolated from the Japanese Kumamoto cannabis strain (DOI:10.1248/cpb.26.3641) and the Œ≤ form was later identified in a Mexican variant of the cannabis plant (PMID: 18774146). The biogenetic relationship of spiro-compounds with cannabinoid acids was proposed (DOI:10.1248/cpb.26.3641). (1S,4R)-7'-Hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetic acid C17H22O4 290.36 290.1518 (1s,4r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetate (1s,4r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetate COC1=CC2=C(C(O)=C1)[C@]1(CC2)CC[C@@H](CC1)OC(C)=O InChI=1S/C17H22O4/c1-11(18)21-13-4-7-17(8-5-13)6-3-12-9-14(20-2)10-15(19)16(12)17/h9-10,13,19H,3-8H2,1-2H3/t13-,17+ MNFMEFPMUGWNCI-XFHMXUHZSA-N belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indan-1-spirocyclohexanes Organic compounds Benzenoids Indanes Indan-1-spirocyclohexanes Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homopolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Ether Hydrocarbon derivative Indan-1-spirocyclohexane Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 3.28 ALOGPS logs -4.06 ALOGPS logp 3.03 ChemAxon pka_strongest_acidic 10.11 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac (1s,4r)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-yl acetate ChemAxon average_mass 290.36 ChemAxon mono_mass 290.1518 ChemAxon smiles COC1=CC2=C(C(O)=C1)[C@]1(CC2)CC[C@@H](CC1)OC(C)=O ChemAxon formula C17H22O4 ChemAxon inchi InChI=1S/C17H22O4/c1-11(18)21-13-4-7-17(8-5-13)6-3-12-9-14(20-2)10-15(19)16(12)17/h9-10,13,19H,3-8H2,1-2H3/t13-,17+ ChemAxon inchikey MNFMEFPMUGWNCI-XFHMXUHZSA-N ChemAxon polar_surface_area 55.76 ChemAxon refractivity 79.23 ChemAxon polarizability 31.83 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Radwan MM, Elsohly MA, Slade D, Ahmed SA, Wilson L, El-Alfy AT, Khan IA, Ross SA: Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry. 2008 Oct;69(14):2627-33. doi: 10.1016/j.phytochem.2008.07.010. Epub 2008 Sep 4. 18774146 1.0 2020-03-19 00:30:51 UTC 2020-08-04 22:28:16 UTC CDB000322 cannabispiradienone Cannabispiradienone belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Cannabispiradienone is also classified as a spiroindane compound. Spiroindane compounds were first isolated and identified as cannabis constituents in 1976. Spiroindane compounds are indane compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Cannabispiradienone is a neutral, hydrophobic molecule that is insoluble in water. Cannabispiradienone is one of several spiroindane compounds that have been found in Cannabis sativa (DOI: 10.1039/P19820001477). Caanabispiradienone was first isolated in the 1970s and synthesized in 1982. Cannabispiradienone can be glycosylated in several ways (PMID: 6991645). It is a non-psychoactive compound but it does appear to have anti-inflammatory effects (PMID: 26101147).¬† C15H14O3 242.27 242.0943 7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-2,5-dien-4-one 7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-2,5-dien-4-one COC1=CC2=C(C(O)=C1)C1(CC2)C=CC(=O)C=C1 InChI=1S/C15H14O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3-4,6-9,17H,2,5H2,1H3 LYSXDJPKAGMDNO-UHFFFAOYSA-N belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Indanes Organic compounds Benzenoids Indanes Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Cyclic ketones Hydrocarbon derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homopolycyclic compound Carbonyl group Cyclic ketone Ether Hydrocarbon derivative Indane Ketone Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenol ether logp 2.54 ALOGPS logs -3.39 ALOGPS logp 2.79 ChemAxon pka_strongest_acidic 9.3 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-2,5-dien-4-one ChemAxon average_mass 242.27 ChemAxon mono_mass 242.0943 ChemAxon smiles COC1=CC2=C(C(O)=C1)C1(CC2)C=CC(=O)C=C1 ChemAxon formula C15H14O3 ChemAxon inchi InChI=1S/C15H14O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3-4,6-9,17H,2,5H2,1H3 ChemAxon inchikey LYSXDJPKAGMDNO-UHFFFAOYSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 71.24 ChemAxon polarizability 25.38 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 90475437 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Granica S, Piwowarski JP, Randazzo A, Schneider P, Zyzynska-Granica B, Zidorn C: Novel stilbenoids, including cannabispiradienone glycosides, from Tragopogon tommasinii (Asteraceae, Cichorieae) and their potential anti-inflammatory activity. Phytochemistry. 2015 Sep;117:254-266. doi: 10.1016/j.phytochem.2015.06.018. Epub 2015 Jun 19. 26101147 Pavlovic R, Panseri S, Giupponi L, Leoni V, Citti C, Cattaneo C, Cavaletto M, Giorgi A: Phytochemical and Ecological Analysis of Two Varieties of Hemp (Cannabis sativa L.) Grown in a Mountain Environment of Italian Alps. Front Plant Sci. 2019 Oct 15;10:1265. doi: 10.3389/fpls.2019.01265. eCollection 2019. 31708938 1.0 2020-03-19 00:30:58 UTC 2020-08-04 22:28:16 UTC CDB000324 dehydrocannabispiran Dehydrocannabispiran or (R)-2‚Ä≤,3‚Ä≤-Dihydro-7‚Ä≤-hydroxy-5‚Ä≤-methoxyspiro[2-cyclohexene-1,1‚Ä≤-[1H]inden]-4-one belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Dehydrocannabispiran is also classified as a spiroindane compound. Spiroindanes were first isolated and identified as cannabis constituents in 1976. Spiroindane compounds are indane compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. Dehydrocannabispiran is neutral, hydrophobic molecule that is insoluble in water. Dehydrocannabispiran is one of several spiroindane, non-cannabinoid phenols that are known in cannabis plants. It was first identified from the dried leaves of a South African C. savita variant grown in France in 1976 (DOI: 10.1016/0040-4020(76)80149-4). A year later it was isolated from the South African cannabis variant grown in Mississippi and was named as dehydrocannabispiran (DOI: 10.1016/0040-4020(77)80249-4). Dehydrocannabispiran was also identified in the Japanese Kumamoto strain (DOI:10.1248/cpb.26.3641). Its structure resembles a synthetic compound which was found to potentiate the estrogenic activity of Stilbestrol (DOI: 10.1016/0040-4020(77)80249-4, PMID: 1255671). C15H16O3 244.29 244.1099 (1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one (1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one COC1=CC2=C(C(O)=C1)[C@@]1(CC2)CCC(=O)C=C1 InChI=1S/C15H16O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3,6,8-9,17H,2,4-5,7H2,1H3/t15-/m1/s1 MVYJADZNMQXLJB-OAHLLOKOSA-N belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Indanes Organic compounds Benzenoids Indanes Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Cyclohexenones Hydrocarbon derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homopolycyclic compound Carbonyl group Cyclic ketone Cyclohexenone Ether Hydrocarbon derivative Indane Ketone Organic oxide Organic oxygen compound Organooxygen compound logp 2.85 ALOGPS logs -3.72 ALOGPS logp 2.8 ChemAxon pka_strongest_acidic 9.33 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (1S)-7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-inden]-2-en-4-one ChemAxon average_mass 244.29 ChemAxon mono_mass 244.1099 ChemAxon smiles COC1=CC2=C(C(O)=C1)[C@@]1(CC2)CCC(=O)C=C1 ChemAxon formula C15H16O3 ChemAxon inchi InChI=1S/C15H16O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h3,6,8-9,17H,2,4-5,7H2,1H3/t15-/m1/s1 ChemAxon inchikey MVYJADZNMQXLJB-OAHLLOKOSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 70.14 ChemAxon polarizability 26.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 134714927 Bailey DJ, Doggett NS, Ng LY, Qazi T: Potentiation of the estrogenic activity of stilbestrol by spiro (cyclohexane-1,2'-indan)-1',4-dione. J Med Chem. 1976 Mar;19(3):438-9. doi: 10.1021/jm00225a024. 1255671 1.0 2020-03-19 00:31:04 UTC 2020-07-24 23:30:06 UTC CDB000326 cannabispirone Cannabispiran also known as Cannabispirone, belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Cannabispiran is formally classified as a phenol an it is one of thirty-four noncannabinoid phenols and one of the nine spiro-indan-type compounds that are found in cannabis plants (https://doi.org/10.1016/S0031-9422(00)81194-2). Spiro compounds are cyclic compounds that include two rings which share a single atom, usually a carbon. The simplest example of this type of compound is Spiro[2.2]pentane. The structure of Cannabispiran is similar to Iso-cannabispiran except the positions of hydroxy and methoxy groups on the benzene ring. C15H18O3 246.31 246.1256 7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-one 7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-one 61262-81-5 COC1=CC2=C(C(O)=C1)C1(CC2)CCC(=O)CC1 InChI=1S/C15H18O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h8-9,17H,2-7H2,1H3 WSWHSHJDUZRVPR-UHFFFAOYSA-N belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indan-1-spirocyclohexanes Organic compounds Benzenoids Indanes Indan-1-spirocyclohexanes Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Cyclic ketones Hydrocarbon derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homopolycyclic compound Carbonyl group Cyclic ketone Ether Hydrocarbon derivative Indan-1-spirocyclohexane Ketone Organic oxide Organic oxygen compound Organooxygen compound logp 2.66 ALOGPS logs -3.46 ALOGPS logp 2.8 ChemAxon pka_strongest_acidic 9.37 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 7'-hydroxy-5'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-one ChemAxon average_mass 246.31 ChemAxon mono_mass 246.1256 ChemAxon smiles COC1=CC2=C(C(O)=C1)C1(CC2)CCC(=O)CC1 ChemAxon formula C15H18O3 ChemAxon inchi InChI=1S/C15H18O3/c1-18-12-8-10-2-5-15(14(10)13(17)9-12)6-3-11(16)4-7-15/h8-9,17H,2-7H2,1H3 ChemAxon inchikey WSWHSHJDUZRVPR-UHFFFAOYSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 69.05 ChemAxon polarizability 26.87 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 162936 1.0 2020-03-19 00:31:08 UTC 2020-08-04 22:28:17 UTC CDB000327 3-[2-(4-Hydroxyphenyl)ethyl]-5-methoxyphenol 3-[2-(4-hydroxyphenyl)ethyl]-5-methoxyphenol, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenoids can be produced by plants and bacteria. Stilbenoids are secondary metabolites present in Cannabis sativa. 3-[2-(4-hydroxyphenyl)ethyl]-5-methoxyphenol is a neutral, hydrophobic compound that is insoluble in water. 3-[2-(4-hydroxyphenyl)ethyl]-5-methoxyphenol is one of several dihydrostilbene or non-cannabinoid stilbenoids that are found in cannabis plants. It was first reported by Bosch and Salemink to be present in the methylene chloride extract of Mexican cannabis and identified as a cannabis constituent in 1978 (PMID: 6991645). C15H16O3 244.29 244.1099 3-[2-(4-hydroxyphenyl)ethyl]-5-methoxyphenol 3-[2-(4-hydroxyphenyl)ethyl]-5-methoxyphenol 67884-29-1 COC1=CC(CCC2=CC=C(O)C=C2)=CC(O)=C1 InChI=1S/C15H16O3/c1-18-15-9-12(8-14(17)10-15)3-2-11-4-6-13(16)7-5-11/h4-10,16-17H,2-3H2,1H3 NSBYGUHECONSDC-UHFFFAOYSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Stilbene logp 3.05 ALOGPS logs -3.72 ALOGPS logp 3.74 ChemAxon pka_strongest_acidic 9.5 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 3-[2-(4-hydroxyphenyl)ethyl]-5-methoxyphenol ChemAxon average_mass 244.29 ChemAxon mono_mass 244.1099 ChemAxon smiles COC1=CC(CCC2=CC=C(O)C=C2)=CC(O)=C1 ChemAxon formula C15H16O3 ChemAxon inchi InChI=1S/C15H16O3/c1-18-15-9-12(8-14(17)10-15)3-2-11-4-6-13(16)7-5-11/h4-10,16-17H,2-3H2,1H3 ChemAxon inchikey NSBYGUHECONSDC-UHFFFAOYSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 70.82 ChemAxon polarizability 26.83 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zhou XM, Zheng CJ, Gan LS, Chen GY, Zhang XP, Song XP, Li GN, Sun CG: Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile. J Nat Prod. 2016 Jul 22;79(7):1791-7. doi: 10.1021/acs.jnatprod.6b00252. Epub 2016 Jun 16. 27310249 1.0 2020-03-19 00:31:11 UTC 2020-08-04 22:28:17 UTC CDB000328 3-[2-(3-Isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol 3-[2-(3-isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenoids can be produced by plants and bacteria. Stilbenoids are secondary metabolites present in Cannabis sativa. 3-[2-(3-isoprenyl-4-hydroxy-5-methoxy-phenyl)ethyl]-5-methoxyphenol is one of several dihydrostilbene or noncannabinoid stilbenoids found in the cannabis plant. It was first reported by Bosch and Salemink to be present in the methylene chloride extract of Mexican cannabis and identified as a cannabis constituent in 1978 (PMID: 6991645). C21H26O4 342.44 342.1831 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-6-(3-methylbut-2-en-1-yl)phenol 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-6-(3-methylbut-2-en-1-yl)phenol COC1=CC(CCC2=CC(CC=C(C)C)=C(O)C(OC)=C2)=CC(O)=C1 InChI=1S/C21H26O4/c1-14(2)5-8-17-9-15(12-20(25-4)21(17)23)6-7-16-10-18(22)13-19(11-16)24-3/h5,9-13,22-23H,6-8H2,1-4H3 MTPFJBMNZHSOND-UHFFFAOYSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Stilbene logp 4.53 ALOGPS logs -4.97 ALOGPS logp 5.32 ChemAxon pka_strongest_acidic 9.46 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-6-(3-methylbut-2-en-1-yl)phenol ChemAxon average_mass 342.44 ChemAxon mono_mass 342.1831 ChemAxon smiles COC1=CC(CCC2=CC(CC=C(C)C)=C(O)C(OC)=C2)=CC(O)=C1 ChemAxon formula C21H26O4 ChemAxon inchi InChI=1S/C21H26O4/c1-14(2)5-8-17-9-15(12-20(25-4)21(17)23)6-7-16-10-18(22)13-19(11-16)24-3/h5,9-13,22-23H,6-8H2,1-4H3 ChemAxon inchikey MTPFJBMNZHSOND-UHFFFAOYSA-N ChemAxon polar_surface_area 58.92 ChemAxon refractivity 101.53 ChemAxon polarizability 39.35 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10427486 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:18 UTC 2020-07-24 23:30:15 UTC CDB000330 cannabidihydrophenanthrene Cannabidihydrophenanthrene, belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivatives where at least one ring C-C bond is substituted by hydrogenation. Cannabidihydrophenanthrene is neutral, hydrophobic molecule that is insoluble in water. Cannabidihydrophenanthrene is the only compound of its type isolated from cannabis. The isolation and identification of cannabidihydrophenanthrene was first reported from Thailand cannabis in 1979. In that same report the authors proposed that cannabidihydrophenanthrene could be biosynthetically derived from the spiro-compound cannabispiradienone, through a dienone-phenol rearrangement (https://doi.org/10.1016/S0040-4039(01)86030-5). Cannabidihydrophenanthrene is one of the non-cannabinoid phenols that have been isolated from cannabis plants (PMID: 6991645). C15H14O3 242.27 242.0943 7-methoxy-9,10-dihydrophenanthrene-3,5-diol 7-methoxy-9,10-dihydrophenanthrene-3,5-diol 71135-80-3 COC1=CC2=C(C(O)=C1)C1=CC(O)=CC=C1CC2 InChI=1S/C15H14O3/c1-18-12-6-10-3-2-9-4-5-11(16)7-13(9)15(10)14(17)8-12/h4-8,16-17H,2-3H2,1H3 PLHFLFWGPBWZHL-UHFFFAOYSA-N belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. Hydrophenanthrenes Organic compounds Benzenoids Phenanthrenes and derivatives Hydrophenanthrenes Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Naphthols and derivatives 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 1-naphthol 2-naphthol Alkyl aryl ether Anisole Aromatic homopolycyclic compound Ether Hydrocarbon derivative Hydrophenanthrene Naphthalene Organic oxygen compound Organooxygen compound Phenol Phenol ether logp 2.72 ALOGPS logs -3.54 ALOGPS logp 3.42 ChemAxon pka_strongest_acidic 9.13 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 7-methoxy-9,10-dihydrophenanthrene-3,5-diol ChemAxon average_mass 242.27 ChemAxon mono_mass 242.0943 ChemAxon smiles COC1=CC2=C(C(O)=C1)C1=CC(O)=CC=C1CC2 ChemAxon formula C15H14O3 ChemAxon inchi InChI=1S/C15H14O3/c1-18-12-6-10-3-2-9-4-5-11(16)7-13(9)15(10)14(17)8-12/h4-8,16-17H,2-3H2,1H3 ChemAxon inchikey PLHFLFWGPBWZHL-UHFFFAOYSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 69.9 ChemAxon polarizability 26.17 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 53438738 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. 28799497 1.0 2020-03-19 00:31:27 UTC 2020-08-04 22:28:17 UTC CDB000333 trans-Anethol Trans-Anethole, also known as E-Anethole, Anise camphor or simply Anethole belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. It is also classified as a phenylpropene. There are two known Anethole isomers including Trans- and Cis-anethole. The more abundant isomer, and the one preferred for use, is the trans or E isomer. Trans-Anethole is a neutral, hydrophobic molecule that is not water soluble. Anethole has a sweet, anise, licorice aroma. Anethole is distinctly sweet, measuring 13 times sweeter than sugar. It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinks ouzo, rakƒ±, anisette and absinthe, among others. It is also used in seasoning and confectionery applications, oral hygiene products, and in small quantities in natural berry flavors. It is a widely used food additive and fragrance agent. Anethole is found in a number of different foods and spices such as anises, star anises, fennels sweet basils, dills, and sweet marjorams. Anethole has also been detected, but not quantified in, common oregano, cumins, white mustards, pepper (spice), and caraway. Trans-Anethole is also one of many non-cannabinoid phenols that are found in cannabis plants (PMID: 6991645). Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977, 17078111, 18944489). (e)-1-(4-Methoxyphenyl)propene (e)-1-Methoxy-4-(1-propenyl)benzene (e)-Anethole (e)-p-Propenylanisole trans-4-(1-Propenyl)anisole trans-p-Methoxy-beta-methylstyrene t-Anethole trans-Anethole trans-p-Methoxy-b-methylstyrene trans-p-Methoxy-β-methylstyrene Anethole, (Z)-isomer 1-Methoxy-4-(1-propenyl)benzene Anethole, (e)-isomer p-Propenylanisole 1-(4-Methoxyphenyl)propene 1-Methoxy-4-(1E)-1-propen-1-ylbenzene (E)-1-p-Methoxyphenylpropene (E)-Anethol 1-Methoxy-4-[(1E)-1-propenyl]benzene trans-1-(4-Methoxyphenyl)-1-propene trans-1-(p-Methoxyphenyl)-1-propene trans-1-(p-Methoxyphenyl)propene trans-1-p-Anisylpropene trans-Anethol trans-p-Anethole 1-Methoxy-4-(1-propen-1-yl)benzene 1-Methoxy-4-propenylbenzene 1-Propene, 1-(4-methoxyphenyl)- 4-(1-Propenyl)anisole 4-(Propen-1-yl)anisole 4-Methoxy-1-propenylbenzene 4-Methoxypropenylbenzene 4-Propenylanisole Anethol Anethole Anise camphor Isoestragole p-1-Propenylanisole p-Anethole p-Methoxy-beta-methylstyrene p-Methoxy-β-methylstyrene p-Propenylphenyl methyl ether C10H12O 148.21 148.0888 1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene anethole 12002-40-3 COC1=CC=C(\C=C\C)C=C1 InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+ RUVINXPYWBROJD-ONEGZZNKSA-N belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anisoles Organic compounds Benzenoids Phenol ethers Anisoles Aromatic homomonocyclic compounds Alkyl aryl ethers Hydrocarbon derivatives Methoxybenzenes Phenoxy compounds Styrenes Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenoxy compound Styrene Monolignols anethole logp 3.40 ALOGPS logs -2.92 ALOGPS logp 2.94 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene ChemAxon average_mass 148.21 ChemAxon mono_mass 148.0888 ChemAxon smiles COC1=CC=C(\C=C\C)C=C1 ChemAxon formula C10H12O ChemAxon inchi InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+ ChemAxon inchikey RUVINXPYWBROJD-ONEGZZNKSA-N ChemAxon polar_surface_area 9.23 ChemAxon refractivity 47.88 ChemAxon polarizability 17.46 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C10428 35616 637563 Anethole C00002713 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 De M, De AK, Sen P, Banerjee AB: Antimicrobial properties of star anise (Illicium verum Hook f). Phytother Res. 2002 Feb;16(1):94-5. doi: 10.1002/ptr.989. 11807977 Fujita K, Fujita T, Kubo I: Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent. Phytother Res. 2007 Jan;21(1):47-51. doi: 10.1002/ptr.2016. 17078111 Oka Y, Nacar S, Putievsky E, Ravid U, Yaniv Z, Spiegel Y: Nematicidal activity of essential oils and their components against the root-knot nematode. Phytopathology. 2000 Jul;90(7):710-5. doi: 10.1094/PHYTO.2000.90.7.710. 18944489 1.0 2020-03-19 00:31:30 UTC 2020-07-31 20:34:13 UTC CDB000334 Apigenin-7-o-p-coumarylglucoside Apigenin-7-O-p-coumarylglucoside belongs to the class of organic compounds known as flavonoid O-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2- or 7-position of the phenylchromen-4-one flavonoid backbone. Apigenin-7-O-p-coumarylglucoside is a derivative of Apigenin in which both a glucose has been attached to the 7-position of the phenylchormen-4-one backbone and a coumaryl alcohol group has been attached to the glucose. The base flavonoid, Apigenin, is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources. Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of total flavonoids (PMID:26487830). Apigenin exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. Apigenin is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). [(2R,3S,4S,5S,6S)-3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid C30H26O12 578.53 578.1424 [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@@H](O)[C@H]1O InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29+,30-/m1/s1 WPQRDUGBKUNFJW-SLUROAMNSA-N belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Flavonoid-7-O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Carbonyl compounds Chromones Cinnamic acid esters Coumaric acid esters Coumaric acids and derivatives Enoate esters Fatty acid esters Flavones Heteroaromatic compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Pyranones and derivatives Secondary alcohols Styrenes Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Alpha,beta-unsaturated carboxylic ester Aromatic heteropolycyclic compound Benzenoid Benzopyran Carbonyl group Carboxylic acid derivative Carboxylic acid ester Chromone Cinnamic acid ester Cinnamic acid or derivatives Coumaric acid ester Coumaric acid or derivatives Enoate ester Fatty acid ester Fatty acyl Flavone Flavonoid-7-o-glycoside Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydroxycinnamic acid or derivatives Hydroxyflavonoid Monocarboxylic acid or derivatives Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Pyran Pyranone Secondary alcohol Styrene Vinylogous acid logp 2.91 ALOGPS logs -3.85 ALOGPS logp 3.17 ChemAxon pka_strongest_acidic 7.29 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate ChemAxon average_mass 578.53 ChemAxon mono_mass 578.1424 ChemAxon smiles O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@@H](O)[C@H]1O ChemAxon formula C30H26O12 ChemAxon inchi InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29+,30-/m1/s1 ChemAxon inchikey WPQRDUGBKUNFJW-SLUROAMNSA-N ChemAxon polar_surface_area 192.44 ChemAxon refractivity 146.61 ChemAxon polarizability 56.52 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Venigalla M, Gyengesi E, Munch G: Curcumin and Apigenin - novel and promising therapeutics against chronic neuroinflammation in Alzheimer's disease. Neural Regen Res. 2015 Aug;10(8):1181-5. doi: 10.4103/1673-5374.162686. 26487830 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:33 UTC 2020-07-31 20:34:13 UTC CDB000335 Apigenin-7-o-glucoside Apigenin-7-O-glucoside, also known as cosmosiin or apigetrin, belongs to the class of organic compounds known as flavonoid 7-O-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2- or 7-position of the phenylchromen-4-one flavonoid backbone. Thus, apigenin 7-O-glucoside consists of the apigenin flavanoid ring linked to glucose at the 7-position. Because of the conjugation of glucose, Apigenin 7-O-glucoside is a moderately water-soluble compound. Apigenin-7-O-glucoside can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Apigenin-7-O-glucoside can also be found in dandelion coffee and in plants such as wild celery and anise. Apigenin-7-O-glucoside has been shown to exhibit anti-platelet function (PMID: 21834233). Apigenin-7-O-glucoside is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside 7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 7-O-beta-D-Glucosyl-5,7,4'-trihydroxyflavone Apigenin 7-O-glucoside Apigetrin Cosmetin Cosmosioside 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl b-D-glucopyranoside 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl β-D-glucopyranoside 7-(b-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 7-(Β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 7-O-b-D-Glucosyl-5,7,4'-trihydroxyflavone 7-O-Β-D-glucosyl-5,7,4'-trihydroxyflavone 4',5,7-Trihydroxyflavone 7-beta-D-glucoside 4',5,7-Trihydroxyflavone 7-β-D-glucoside 7-O-beta-D-Glucopyranosylapigenin 7-O-beta-D-Glucosylapigenin 7-O-Β-D-glucopyranosylapigenin 7-O-Β-D-glucosylapigenin Apigenin 7-beta-D-glucoside Apigenin 7-beta-glucopyranoside Apigenin 7-glucoside Apigenin 7-O-beta-D-glucopyranoside Apigenin 7-O-beta-D-glucoside Apigenin 7-O-beta-glucopyranoside Apigenin 7-O-beta-glucoside Apigenin 7-O-β-D-glucopyranoside Apigenin 7-O-β-D-glucoside Apigenin 7-O-β-glucopyranoside Apigenin 7-O-β-glucoside Apigenin 7-β-D-glucoside Apigenin 7-β-glucopyranoside Apigenin-7-glucoside Cosmociin Cosmoside Cosmosiine Apigenin-7-D-glucoside Apigenin-7-O-beta-D-glucopyranoside Cosmosiin Apigenin 7-O-b-D-glucoside 4’,5,7-Trihydroxyflavone 7-β-D-glucoside Apigenin-7-O-4C1-beta-D-glucoside Apigenin-7-O-4C1-β-D-glucoside C21H20O10 432.38 432.1056 5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one apigenin 7-o-β-glucoside 578-74-5 OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1 KMOUJOKENFFTPU-QNDFHXLGSA-N belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Flavonoid-7-O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Benzene and substituted derivatives Chromones Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Flavone Flavonoid-7-o-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid Flavones and Flavonols beta-D-glucoside dihydroxyflavone flavones glycosyloxyflavone monosaccharide derivative logp 0.68 ALOGPS logs -2.65 ALOGPS logp 0.44 ChemAxon pka_strongest_acidic 7.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 432.38 ChemAxon mono_mass 432.1056 ChemAxon smiles OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C21H20O10 ChemAxon inchi InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1 ChemAxon inchikey KMOUJOKENFFTPU-QNDFHXLGSA-N ChemAxon polar_surface_area 166.14 ChemAxon refractivity 105.06 ChemAxon polarizability 42.1 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003911 5280704 4532607 C00001017 C04608 APIGENIN-7-O-BETA-D-GLUCOSIDE Apigetrin 16778 Chaves DS, Frattani FS, Assafim M, de Almeida AP, de Zingali RB, Costa SS: Phenolic chemical composition of Petroselinum crispum extract and its effect on haemostasis. Nat Prod Commun. 2011 Jul;6(7):961-4. 21834233 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:37 UTC 2020-07-31 20:34:11 UTC CDB000336 Apigenin 7-o-glucoside Apigenin 7-o-glucoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, apigenin 7-O-glucoside is considered to be a flavonoid lipid molecule. Apigenin 7-o-glucoside is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Apigenin 7-o-glucoside is one of the major flavonoid glycosides present in low-THC Cannabis cultivars. (PMID: 6991645) C21H20O10 432.38 432.1056 5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one 5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one OC[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18+,19-,20+,21+/m0/s1 KMOUJOKENFFTPU-JOZSIVFUSA-N belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Flavonoid-7-O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Benzene and substituted derivatives Chromones Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Flavone Flavonoid-7-o-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid logp 0.68 ALOGPS logs -2.65 ALOGPS logp 0.44 ChemAxon pka_strongest_acidic 7.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 432.38 ChemAxon mono_mass 432.1056 ChemAxon smiles OC[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C21H20O10 ChemAxon inchi InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18+,19-,20+,21+/m0/s1 ChemAxon inchikey KMOUJOKENFFTPU-JOZSIVFUSA-N ChemAxon polar_surface_area 166.14 ChemAxon refractivity 105.06 ChemAxon polarizability 42.05 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-19 00:31:40 UTC 2020-08-04 22:28:17 UTC CDB000337 Isovitexin 7-O-glucoside 2''-O-arabinoside Isovitexin 7-O-glucoside 2''-O-arabinoside belongs to the class of organic compounds known as flavonoid O-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2- or 7-position of the phenylchromen-4-one flavonoid backbone. Thus, Isovitexin-7-O-glucoside 2''-O-arabinoside consists of the apigenin flavanoid with a 1,5-anhydro-D-glucitol group at the C-6 position of apigenin linked to glucose at the O-7 position of apigenin and arabinose linked to glucose at its 2‚Äù-position. Isovitexin-7-O-glucoside 2''-O-arabinoside is a derivative of isovitexin. Isovitexin is a C-glycosylated polyphenol that can be found in the passionflower, Cannabis, and the a√ßa√≠ palm. Isovitexin can have a number of sugar moieties attached to it, including glucose (leading to Isovitexin 7-O-glucoside, Isovitexin 7,2"-di-O-glucoside, Isovitexin C-glucoside), rhamnose (leading to Isovitexin 7-rhamnoglucoside) and glucose and arabinoside (leading to Isovitexin 7-O-glucoside 2''-O-arabinoside). Isovitexin-7-O-glucoside 2''-O-arabinoside is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). C32H38O19 726.64 726.2007 6-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one 6-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one OC[C@H]1O[C@@H](OC2=CC3=C(C(=O)C=C(O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C32H38O19/c33-7-17-23(40)26(43)30(51-31-27(44)21(38)13(37)9-46-31)29(48-17)20-16(49-32-28(45)25(42)22(39)18(8-34)50-32)6-15-19(24(20)41)12(36)5-14(47-15)10-1-3-11(35)4-2-10/h1-6,13,17-18,21-23,25-35,37-45H,7-9H2/t13-,17+,18+,21-,22+,23+,25-,26-,27+,28-,29-,30-,31-,32+/m0/s1 XGYOBHDFARGUCG-WILIUIQXSA-N logp -1.03 ALOGPS logs -1.73 ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 6.87 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 6-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 726.64 ChemAxon mono_mass 726.2007 ChemAxon smiles OC[C@H]1O[C@@H](OC2=CC3=C(C(=O)C=C(O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@@H]2OC[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C32H38O19 ChemAxon inchi InChI=1S/C32H38O19/c33-7-17-23(40)26(43)30(51-31-27(44)21(38)13(37)9-46-31)29(48-17)20-16(49-32-28(45)25(42)22(39)18(8-34)50-32)6-15-19(24(20)41)12(36)5-14(47-15)10-1-3-11(35)4-2-10/h1-6,13,17-18,21-23,25-35,37-45H,7-9H2/t13-,17+,18+,21-,22+,23+,25-,26-,27+,28-,29-,30-,31-,32+/m0/s1 ChemAxon inchikey XGYOBHDFARGUCG-WILIUIQXSA-N ChemAxon polar_surface_area 315.21 ChemAxon refractivity 164.63 ChemAxon polarizability 69.53 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 19 ChemAxon donor_count 12 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 6 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:43 UTC 2020-08-04 22:28:17 UTC CDB000338 Isovitexin- 4'-o-glucoside isovitexin- o-glucoside belongs to the class of organic compounds known as flavonoid C-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. isovitexin-4'- o-glucoside was found in the cannabis plant. It is a derivative of isovitexin that the glucoside moiety positionong on C-4'. Isovitexin (or homovitexin, saponaretin) is a flavone. It can be found in the passion flower, Cannabis, and the a√ßa√≠ palm. In fact, isovitexin-o-glucoside is one of the flavonoid glycosides that were identified in the cannabis plant and the glucose moiety can be attached either to 4 position of the flavonoid or on the sugar moiety). If the Glucoside attach on the sugar moiety, there are 5 possible isomer for that.(PMID: 6991645) C27H30O15 594.52 594.1585 5,7-dihydroxy-6-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one 5,7-dihydroxy-6-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C([C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(41-15)18-12(31)6-14-17(21(18)34)11(30)5-13(40-14)9-1-3-10(4-2-9)39-27-25(38)23(36)20(33)16(8-29)42-27/h1-6,15-16,19-20,22-29,31-38H,7-8H2/t15-,16+,19-,20+,22+,23-,24-,25+,26+,27+/m0/s1 SFNFQCXADNWOCI-FWWRQVNSSA-N logp -0.75 ALOGPS logs -2.36 ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 6.14 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 5,7-dihydroxy-6-[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one ChemAxon average_mass 594.52 ChemAxon mono_mass 594.1585 ChemAxon smiles OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C([C@H]4O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]4O)=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C27H30O15 ChemAxon inchi InChI=1S/C27H30O15/c28-7-15-19(32)22(35)24(37)26(41-15)18-12(31)6-14-17(21(18)34)11(30)5-13(40-14)9-1-3-10(4-2-9)39-27-25(38)23(36)20(33)16(8-29)42-27/h1-6,15-16,19-20,22-29,31-38H,7-8H2/t15-,16+,19-,20+,22+,23-,24-,25+,26+,27+/m0/s1 ChemAxon inchikey SFNFQCXADNWOCI-FWWRQVNSSA-N ChemAxon polar_surface_area 256.29 ChemAxon refractivity 138.18 ChemAxon polarizability 58.45 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:46 UTC 2020-08-04 22:28:17 UTC CDB000339 Isovitexin-7-o-rhamnoglucoside Isovitexin-7-O-rhamnoglucoside belongs to the class of organic compounds known as flavonoid O-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2- or 7-position of the phenylchromen-4-one flavonoid backbone. Thus, Isovitexin-7-O-glucoside consists of the apigenin flavanoid with a 1,5-anhydro-D-glucitol group at the C-6 position of apigenin linked to rhamnose at the O-7 position of apigenin. Isovitexin-7-O-rhamnoglucoside is a derivative of isovitexin. Isovitexin is a C-glycosylated polyphenol that can be found in the passionflower, Cannabis, and the a√ßa√≠ palm. Isovitexin can have a number of sugar moieties attached to it, including glucose (leading to Isovitexin 7-O-glucoside, Isovitexin 7,2"-di-O-glucoside, Isovitexin C-glucoside) and rhamnose (leading to Isovitexin 7-rhamnoglucoside). Isovitexin-7-O-rhamnoglucoside is one of everal dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). C33H40O19 740.66 740.2164 7-{[(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one 7-{[(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one C[C@H]1O[C@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](CO)O[C@@H]2OC2=CC3=C(C(=O)C=C(O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C33H40O19/c1-10-21(38)25(42)29(46)32(47-10)52-31-27(44)23(40)18(9-35)51-33(31)50-16-7-15-19(13(37)6-14(48-15)11-2-4-12(36)5-3-11)24(41)20(16)30-28(45)26(43)22(39)17(8-34)49-30/h2-7,10,17-18,21-23,25-36,38-46H,8-9H2,1H3/t10-,17-,18+,21-,22-,23+,25-,26+,27+,28+,29+,30+,31+,32-,33+/m1/s1 PSNRLITVALDHGL-CWJBGNNISA-N logp -0.71 ALOGPS logs -1.79 ALOGPS logp -3 ChemAxon pka_strongest_acidic 6.87 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 7-{[(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one ChemAxon average_mass 740.66 ChemAxon mono_mass 740.2164 ChemAxon smiles C[C@H]1O[C@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](CO)O[C@@H]2OC2=CC3=C(C(=O)C=C(O3)C3=CC=C(O)C=C3)C(O)=C2[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O ChemAxon formula C33H40O19 ChemAxon inchi InChI=1S/C33H40O19/c1-10-21(38)25(42)29(46)32(47-10)52-31-27(44)23(40)18(9-35)51-33(31)50-16-7-15-19(13(37)6-14(48-15)11-2-4-12(36)5-3-11)24(41)20(16)30-28(45)26(43)22(39)17(8-34)49-30/h2-7,10,17-18,21-23,25-36,38-46H,8-9H2,1H3/t10-,17-,18+,21-,22-,23+,25-,26+,27+,28+,29+,30+,31+,32-,33+/m1/s1 ChemAxon inchikey PSNRLITVALDHGL-CWJBGNNISA-N ChemAxon polar_surface_area 315.21 ChemAxon refractivity 169.05 ChemAxon polarizability 71.7 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 19 ChemAxon donor_count 12 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 6 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:50 UTC 2020-08-04 22:28:17 UTC CDB000340 Cynaroside Luteolin-7-O-glucoside, also known as 7-O-glucoluteolin or cinaroside, belongs to the class of organic compounds known as flavonoid O-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. glucoside. Because of the conjugation of glucose, Luteolin 7-O-glucoside is a moderately water-soluble compound. Luteolin 7-O-glucoside is found, on average, in a few different plants, spices and foods, such as Mexican oregano, anises, and wild celeries and in a lower concentration in lentils, and wild carrots. common buckwheats, corns, globe artichokes, roman camomiles, and orange mints. Luteolin 7-O-glucoside is one of veral dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside 2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one 7-Glucoluteolin 7-Glucosylluteolin 7-O-beta-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone Cinaroside Cynaroside Luteolin 7-monoglucoside Luteolin 7-O-glucopyranoside Luteolin 7-O-glucoside Luteolin-7-glucoside Luteoloside 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl b-D-glucopyranoside 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl β-D-glucopyranoside 2-(3,4-Dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one 2-(3,4-Dihydroxyphenyl)-7-(β-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one 7-O-b-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone 7-O-Β-D-glucosyl-5,7,3',4'-tetrahydroxyflavone Daphneflavonoloside Flavopurposide Glucoluteolin Luteolin 7-O-beta-D-glucoside Luteolin 7-glucoside Luteolin 7-O-b-D-glucoside Luteolin 7-O-β-D-glucoside Nephrocizin Luteolin-7-O-monoglucoside Luteolin-7-O-beta-D-glucopyranoside Luteolin-7-beta-D-glucoside 3',4',5,7-Tetrahydroxyflavone 7-beta-D-glucopyranoside 3',4',5,7-Tetrahydroxyflavone 7-β-D-glucopyranoside 3’,4’,5,7-Tetrahydroxyflavone 7-β-D-glucopyranoside 3',4',5-Trihydroxyflavone 7-O-beta-D-glucopyranoside 3',4',5-Trihydroxyflavone 7-O-β-D-glucopyranoside 3’,4’,5-Trihydroxyflavone 7-O-β-D-glucopyranoside 7-(beta-D-Glucosyloxy)-3',4',5-trihydroxyflavone 7-(β-D-Glucosyloxy)-3',4',5-trihydroxyflavone 7-(β-D-Glucosyloxy)-3’,4’,5-trihydroxyflavone 7-O-beta-D-Glucosylluteolin 7-O-β-D-Glucosylluteolin Luteolin 7-O-beta-D-glucopyranoside Luteolin 7-O-β-D-glucopyranoside Luteolin 7-O-beta-glucopyranoside Luteolin 7-O-β-glucopyranoside Luteolin 7-O-beta-glucoside Luteolin 7-O-β-glucoside Luteolin 7-beta-D-glucoside Luteolin 7-β-D-glucoside C21H20O11 448.38 448.1006 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one luteolin 7-O-glucoside 5373-11-5 OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 PEFNSGRTCBGNAN-QNDFHXLGSA-N belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Flavonoid-7-O-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Benzene and substituted derivatives Catechols Chromones Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Flavone Flavonoid-7-o-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid Flavones and Flavonols beta-D-glucoside flavones glycosyloxyflavone monosaccharide derivative trihydroxyflavone melting_point 256 - 258 °C logp 0.58 ALOGPS logs -2.62 ALOGPS logp 0.14 ChemAxon pka_strongest_acidic 7.3 ChemAxon pka_strongest_basic -3 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 448.38 ChemAxon mono_mass 448.1006 ChemAxon smiles OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C21H20O11 ChemAxon inchi InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 ChemAxon inchikey PEFNSGRTCBGNAN-QNDFHXLGSA-N ChemAxon polar_surface_area 186.37 ChemAxon refractivity 107.04 ChemAxon polarizability 42.98 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014280 4444241 5280637 C03951 27994 245 LUTEOLIN-7-O-BETA-D-GLUCOSIDE C00004266 Cynaroside Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:53 UTC 2020-08-04 22:28:17 UTC CDB000341 Orientin-7-o-glucoside Orientin-7-O-glucoside or Orientin-7-glucoside is a derivative of the flavone known as Orientin. It belongs to the class of organic compounds known as flavonoid 7-O-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, orientin 7-O-glucoside consists of a luteolin flavonoid backbone with a glucose ring attached at the 8-C position and glucose attached at the O-7 position. Orientin-7-O-glucoside is quite water soluble due to the attachment of several sugar moieties. Orientin-7-O-glucoside Orientin is a water-soluble flavonoid C-glycoside found in calcium tree and black bamboo. Orientin has been detected, but not quantified in, several different foods, such as spelts, triticales, red rices, hard wheats, and flaxseeds. Orientin is also found in the passionflower, the A√ßa√≠ palm, buckwheat sprouts, and in millets. Orientin exhibits antioxidant, antiaging, antiviral, antibacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, antiadipogenesis, and antinociceptive activities (https://doi.org/10.1155/2016/4104595). Orientin can have a number of sugar moieties attached to it, including rhamnose (leading to Orientin-7-O-rhamnoglucoside) and glucose (leading to Orientin-7-O-glucoside). Orientin-7-O-glucoside is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). C27H30O16 610.52 610.1534 2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one 2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C27H30O16/c28-6-15-19(34)21(36)23(38)26(41-15)18-14(42-27-24(39)22(37)20(35)16(7-29)43-27)5-12(33)17-11(32)4-13(40-25(17)18)8-1-2-9(30)10(31)3-8/h1-5,15-16,19-24,26-31,33-39H,6-7H2/t15-,16+,19+,20+,21-,22-,23+,24+,26-,27+/m0/s1 SPAHGZOYBCREJA-XJHXITLBSA-N logp -0.99 ALOGPS logs -1.94 ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 7.24 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 610.52 ChemAxon mono_mass 610.1534 ChemAxon smiles OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C27H30O16 ChemAxon inchi InChI=1S/C27H30O16/c28-6-15-19(34)21(36)23(38)26(41-15)18-14(42-27-24(39)22(37)20(35)16(7-29)43-27)5-12(33)17-11(32)4-13(40-25(17)18)8-1-2-9(30)10(31)3-8/h1-5,15-16,19-24,26-31,33-39H,6-7H2/t15-,16+,19+,20+,21-,22-,23+,24+,26-,27+/m0/s1 ChemAxon inchikey SPAHGZOYBCREJA-XJHXITLBSA-N ChemAxon polar_surface_area 276.52 ChemAxon refractivity 140.16 ChemAxon polarizability 58.18 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 16 ChemAxon donor_count 11 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:31:56 UTC 2020-08-04 22:28:17 UTC CDB000342 Orientin-7-o-rhamnoglucoside Orientin-7-O-rhamnoglucoside is a derivative of the flavone known as orientin. It belongs to the class of organic compounds known as flavonoid 7-O-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, Orientin-7-O-rhamnoglucoside consists of a luteolin flavonoid backbone with a glucose moiety attached at the 8-C position of luteiolin and a rhamnose group attached the 7-O position. Orientin can have a number of sugar moieties attached to it, including glucose (leading to Orientin-7-O-glucoside) and rhamnose (leading to Orientin-7-O-rhamnoglucoside). Orientin-7-O-rhamnoglucoside is a very water soluble flavonoid C-glycoside found in calcium tree and black bamboo. Orientin has been detected, but not quantified in, several different foods including spelts, triticales, red rices, hard wheats, and flaxseeds. Orientin is also found in the passionflower, the A√ßa√≠ palm, buckwheat sprouts, and in millets. Orientin exhibits antioxidant, antiaging, antiviral, antibacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, antiadipogenesis, and antinociceptive activities (https://doi.org/10.1155/2016/4104595). Orientin-7-O-rhamnoglucoside is one of several dozen flavonoid glycosides that are known in cannabis plants. It was first isolated and identified as a cannabis constituent in 1973 (PMID: 6991645). C33H40O20 756.66 756.2113 7-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one 7-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@H]2O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]2O)C2=CC(O)=C(O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C33H40O20/c1-9-21(40)24(43)28(47)32(48-9)53-31-26(45)23(42)18(8-35)52-33(31)51-16-6-14(39)19-13(38)5-15(10-2-3-11(36)12(37)4-10)49-29(19)20(16)30-27(46)25(44)22(41)17(7-34)50-30/h2-6,9,17-18,21-28,30-37,39-47H,7-8H2,1H3/t9-,17+,18-,21-,22+,23+,24+,25+,26+,27+,28+,30-,31-,32-,33+/m1/s1 JDOFHNMFDMQLAO-MVXLWSPJSA-N logp -0.92 ALOGPS logs -1.70 ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 7.24 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 7-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-8-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one ChemAxon average_mass 756.66 ChemAxon mono_mass 756.2113 ChemAxon smiles C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@H]2O[C@@H](CO)[C@H](O)[C@H](O)[C@@H]2O)C2=CC(O)=C(O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C33H40O20 ChemAxon inchi InChI=1S/C33H40O20/c1-9-21(40)24(43)28(47)32(48-9)53-31-26(45)23(42)18(8-35)52-33(31)51-16-6-14(39)19-13(38)5-15(10-2-3-11(36)12(37)4-10)49-29(19)20(16)30-27(46)25(44)22(41)17(7-34)50-30/h2-6,9,17-18,21-28,30-37,39-47H,7-8H2,1H3/t9-,17+,18-,21-,22+,23+,24+,25+,26+,27+,28+,30-,31-,32-,33+/m1/s1 ChemAxon inchikey JDOFHNMFDMQLAO-MVXLWSPJSA-N ChemAxon polar_surface_area 335.44 ChemAxon refractivity 171.03 ChemAxon polarizability 72.26 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 20 ChemAxon donor_count 13 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 6 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:32:00 UTC 2020-07-31 20:34:19 UTC CDB000343 Vitexin-7-o-(6'-glucoside) vitexin-7-o-(6'-glucoside) belongs to the class of organic compounds known as flavonoid c-glycosides. vitexin-7-o-(6'-glucoside) is a derivative of vitexin. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn. vitexin-7-o-(6'-glucoside) is one of the flavonoids that have been identified in the cannabis plant. (PMID: 6991645) C27H30O15 594.52 594.1585 5-hydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one 5-hydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one OC[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=C(O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C27H30O15/c28-7-15-19(33)21(35)23(37)26(40-15)18-14(41-27-24(38)22(36)20(34)16(8-29)42-27)6-12(32)17-11(31)5-13(39-25(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-24,26-30,32-38H,7-8H2/t15-,16-,19+,20+,21-,22-,23+,24-,26-,27+/m0/s1 HHRPSKAYQPDDGQ-MYGKGALCSA-N logp -0.85 ALOGPS logs -1.99 ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 7.24 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 5-hydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-{[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 594.52 ChemAxon mono_mass 594.1585 ChemAxon smiles OC[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2[C@@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=C(O)C=C2)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C27H30O15 ChemAxon inchi InChI=1S/C27H30O15/c28-7-15-19(33)21(35)23(37)26(40-15)18-14(41-27-24(38)22(36)20(34)16(8-29)42-27)6-12(32)17-11(31)5-13(39-25(17)18)9-1-3-10(30)4-2-9/h1-6,15-16,19-24,26-30,32-38H,7-8H2/t15-,16-,19+,20+,21-,22-,23+,24-,26-,27+/m0/s1 ChemAxon inchikey HHRPSKAYQPDDGQ-MYGKGALCSA-N ChemAxon polar_surface_area 256.29 ChemAxon refractivity 138.18 ChemAxon polarizability 56.78 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-19 00:32:02 UTC 2020-08-04 22:28:17 UTC CDB000344 Vitexin-4'-o-rhamnoglucoside  vitexin-o-rhamnoglucoside belongs to the class of organic compounds known as flavonoid c-glycosides. vitexin-o-rhamnoglucoside is a derivative of Vitexin. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn. vitexin-4'-o-rhamnoglucoside is one of the flavonoids that have been identified in the cannabis plant. In vitexin-o-glucoside, with rhamnose and glucose either on 4 position of flavonoid or on the sugar moiety. If the Glucose attach on the sugar moiety, there are 5 possible isomer for that.(PMID: 6991645) C33H40O19 740.66 740.2164 5,7-dihydroxy-8-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one 5,7-dihydroxy-8-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)chromen-4-one C[C@H]1O[C@@H](OC[C@@H]2O[C@H](OC3=CC=C(C=C3)C3=CC(=O)C4=C(O)C=C(O)C([C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=C4O3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C33H40O19/c1-10-21(38)24(41)28(45)32(48-10)47-9-18-23(40)26(43)29(46)33(52-18)49-12-4-2-11(3-5-12)16-7-15(37)19-13(35)6-14(36)20(30(19)50-16)31-27(44)25(42)22(39)17(8-34)51-31/h2-7,10,17-18,21-29,31-36,38-46H,8-9H2,1H3/t10-,17-,18+,21-,22-,23-,24+,25+,26+,27-,28-,29-,31-,32-,33+/m1/s1 MHROQFYVRYVXRY-MGTKCHPPSA-N logp -0.75 ALOGPS logs -2.16 ALOGPS logp -3 ChemAxon pka_strongest_acidic 6.17 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 5,7-dihydroxy-8-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-(4-{[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)-4H-chromen-4-one ChemAxon average_mass 740.66 ChemAxon mono_mass 740.2164 ChemAxon smiles C[C@H]1O[C@@H](OC[C@@H]2O[C@H](OC3=CC=C(C=C3)C3=CC(=O)C4=C(O)C=C(O)C([C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=C4O3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C33H40O19 ChemAxon inchi InChI=1S/C33H40O19/c1-10-21(38)24(41)28(45)32(48-10)47-9-18-23(40)26(43)29(46)33(52-18)49-12-4-2-11(3-5-12)16-7-15(37)19-13(35)6-14(36)20(30(19)50-16)31-27(44)25(42)22(39)17(8-34)51-31/h2-7,10,17-18,21-29,31-36,38-46H,8-9H2,1H3/t10-,17-,18+,21-,22-,23-,24+,25+,26+,27-,28-,29-,31-,32-,33+/m1/s1 ChemAxon inchikey MHROQFYVRYVXRY-MGTKCHPPSA-N ChemAxon polar_surface_area 315.21 ChemAxon refractivity 169.05 ChemAxon polarizability 70.57 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 19 ChemAxon donor_count 12 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 6 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:32:05 UTC 2020-08-04 22:28:17 UTC CDB000345 Carotene Alpha carotene belongs to the group of compounds known as carotenoids. More specifically carotenoids are classified as tetraterpenoids, being built from four terpene units (8 isoprene units) each containing 10 carbon atoms. As a result, carotenoids typically have a total of 40 carbon atoms. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long-branched alkyl chain. There are more than 1100 known carotenoids. Carotenoids can be further categorized into two classes, xanthophylls (which contain oxygen) and carotenes (which are purely hydrocarbons and contain no oxygen). Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. Alpha-carotene is one of the primary isomers of carotene, although Beta-carotene is the most abundant. There are six known carotene isomers including Œ±-, Œ≤-, Œ≥-, Œ¥-, Œµ-, and Œ∂-carotene. These carotene isomers contain unsubstituted beta-ionone rings, which means they can be readily converted to retinol and vitamin A. In other words, they have pro-vitamin A activity. Alpha-carotene has less vitamin A activity than Beta-Carotene. This is because of its structure, as Alpha-carotene it is converted to just one molecule of biologically active retinol after central cleavage, while Beta-carotene is converted to two molecules after cleavage. Plants, fungi, and photosynthetic bacteria synthesize carotenes, while animals must obtain them as a dietary nutrient. In plants carotenes contribute to photosynthesis by transmitting the light energy they absorb to chlorophyll. They also protect plant tissues by helping to absorb the energy from singlet oxygen, an excited form of the oxygen molecule O2 which is formed during photosynthesis. Alpha-carotene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Alpha-carotene is found in many common orange-, yellow-, and green-colored fruits and vegetables such as carrots, pumpkins, squash, apricots, sweet potatoes, and beans. The concentration of Œ±-Carotene is especially high in orange carrots and high serum concentrations are associated with high carrot intake. Other plants and foods that have high levels of alpha-carotene include cloves, shallots, cumin, wolfberries, cantaloupes, papaya, spinach, broccoli, turnip, avocado, green peas, orange and red peppers, and tomatoes. Alpha-carotene (along with beta-carotene) exhibits numerous beneficial health or pharmacological properties including antioxidant, anti-obesity, anti-cancer, anti-aging, anti-atherosclerotic and anti-sunburn properties as well as hepatoprotective, neuroprotective and improved vision and night blindness prevention ( PMID: 27047317). Alpha-carotene is one of a small number of pigments including (beta-carotene and xanthophylls) found in cannabis plants. It was first isolated from hemp leaves and identified as a cannabis constituent in 1969 (PMID: 6991645). (+)-alpha-Carotene alpha-Carotene (natural) (+)-a-Carotene (+)-α-Carotene a-Carotene α-Carotene a-Carotene (natural) α-carotene (natural) Carotenes Carotenoids alpha-Carotene, (6'R)-isomer alpha-Carotene (6'R)-alpha-Carotene (6'R)-beta,epsilon-Carotene (6'R)-α-Carotene (6'R)-β,ε-Carotene (6’R)-α-Carotene (6’R)-β,ε-Carotene all-trans-alpha-Carotene all-trans-α-Carotene α-Carotene, (6’R)-isomer C40H56 536.87 536.4382 (6R)-1,5,5-trimethyl-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene hi-α C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1 ANVAOWXLWRTKGA-NTXLUARGSA-N belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Carotenes Organic compounds Lipids and lipid-like molecules Prenol lipids Tetraterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Carotene Cyclic olefin Cycloalkene Hydrocarbon Olefin Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon C40 isoprenoids (tetraterpenes) alpha-carotene melting_point 187.5 °C logp 9.79 ALOGPS logs -6.24 ALOGPS logp 11.17 ChemAxon iupac (6R)-1,5,5-trimethyl-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene ChemAxon average_mass 536.87 ChemAxon mono_mass 536.4382 ChemAxon smiles C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C ChemAxon formula C40H56 ChemAxon inchi InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1 ChemAxon inchikey ANVAOWXLWRTKGA-NTXLUARGSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 191.88 ChemAxon polarizability 71.41 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4925358 6419725 FDB013716 C05433 35147 C00003765 CPD1F-118 Alpha-Carotene 6998 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kim JK: An update on the potential health benefits of carotenes. EXCLI J. 2016 Jan 6;15:1-4. doi: 10.17179/excli2015-664. eCollection 2016. 27047317 During A, Smith MK, Piper JB, Smith JC: beta-Carotene 15,15'-Dioxygenase activity in human tissues and cells: evidence of an iron dependency. J Nutr Biochem. 2001 Nov;12(11):640-647. doi: 10.1016/s0955-2863(01)00184-x. 12031257 dela Sena C, Narayanasamy S, Riedl KM, Curley RW Jr, Schwartz SJ, Harrison EH: Substrate specificity of purified recombinant human beta-carotene 15,15'-oxygenase (BCO1). J Biol Chem. 2013 Dec 27;288(52):37094-103. doi: 10.1074/jbc.M113.507160. Epub 2013 Nov 1. 24187135 Fraser PD, Bramley PM: The biosynthesis and nutritional uses of carotenoids. Prog Lipid Res. 2004 May;43(3):228-65. doi: 10.1016/j.plipres.2003.10.002. 15003396 1.0 2020-03-19 00:32:08 UTC 2020-07-24 23:30:19 UTC CDB000346 Xanthophyll Xanthophyll is an organic compound, also known as Lutein (LOO-teen) is a oxygenated carotenoid found in vegetables and fruits. Xanthophylls (originally phylloxanthins) are yellow pigments that occur widely in nature and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. The name is from Greek xanthos, and phyllon, due to their formation of the yellow band seen in early chromatography of leaf pigments. Xanthophylls along with Carotene are known as pigments in the cannabis plant. (PMID: 6991645) (3R,3'r,6'r,9'-cis)-b,epsilon-Carotene-3,3'-diol (3R,3'r,6'r,9'-cis)-Β,epsilon-carotene-3,3'-diol Lutein Lutein g Lutein, gamma gamma Lutein C40H56O2 568.87 568.428 (1R,4S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol lutein F 127-40-2 C\C(\C=C\C=C(/C)\C=C\[C@@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37+/m0/s1 KBPHJBAIARWVSC-WTAPCXIZSA-N belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Xanthophylls Organic compounds Lipids and lipid-like molecules Prenol lipids Tetraterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homomonocyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Xanthophyll C40 isoprenoids (tetraterpenes) logp 8.29 ALOGPS logs -5.89 ALOGPS logp 8.55 ChemAxon pka_strongest_acidic 18.22 ChemAxon pka_strongest_basic -0.91 ChemAxon iupac (1R,4S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol ChemAxon average_mass 568.87 ChemAxon mono_mass 568.428 ChemAxon smiles C\C(\C=C\C=C(/C)\C=C\[C@@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C ChemAxon formula C40H56O2 ChemAxon inchi InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37+/m0/s1 ChemAxon inchikey KBPHJBAIARWVSC-WTAPCXIZSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 195.06 ChemAxon polarizability 72.98 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB023085 16061195 1.0 2020-03-19 00:32:11 UTC 2020-08-04 22:28:17 UTC CDB000347 cannabisin d Cannabisin D, is a dimethylated derivative of cannabisin B. It is a lignanamide and belongs to the class of organic compounds known as lignans, neolignans and related compounds. Lignanamides are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9‚àö√ᬨ¬• and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Cannabisin D has been isolated from the roots, fruits and seeds of cannabis plants (PMID: 28799497). It is a neutral, hydrophobic molecule that is largely insoluble in water. Even though relatively little information exists regarding the biological function of cannabisin D, it has been established that its analog cannabisin B functions predominantly as an antioxidant in hemp seed (PMID: 23411211). It has also been established that cannabisin B has considerable antiproliferative potential by inducing the autphagic cell death of HepG2 cells, turning it into a promising agent against hepatoblastoma disease (PMID: 23411211). Cannabisins and other lignanamides exhibit interesting and diverse biological activities, including feeding deterrent activity and insecticidal effects (that protect the plant) as well as anti-inflammatory, antioxidant and anti-acetylcholinesterase activity, which may have beneficial health effects (PMID: 26585089). Cannibasins have been found to suppress the production and lower the levels of mRNA of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor Œ± (TNF-Œ±) in a concentration-dependent manner in LPS-stimulated BV2 microglia cells (PMID: 30691004). C36H36N2O8 624.69 624.2472 (1R,2S)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid (1R,2S)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid COC1=C(O)C=CC(=C1)[C@H]1[C@H](C(O)=NCCC2=CC=C(O)C=C2)C(=CC2=CC(OC)=C(O)C=C12)C(=O)NCCC1=CC=C(O)C=C1 InChI=1S/C36H36N2O8/c1-45-31-18-23(7-12-29(31)41)33-27-20-30(42)32(46-2)19-24(27)17-28(35(43)37-15-13-21-3-8-25(39)9-4-21)34(33)36(44)38-16-14-22-5-10-26(40)11-6-22/h3-12,17-20,33-34,39-42H,13-16H2,1-2H3,(H,37,43)(H,38,44)/t33-,34-/m1/s1 XYTYRVFKBJENPE-KKLWWLSJSA-N belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. Aryltetralin lignans Organic compounds Lignans, neolignans and related compounds Aryltetralin lignans Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Naphthalenecarboxylic acids and derivatives Organic oxides Organonitrogen compounds Phenoxy compounds Secondary carboxylic acid amides 1-aryltetralin lignan 1-hydroxy-2-unsubstituted benzenoid 2-naphthalenecarboxylic acid or derivatives Alkyl aryl ether Anisole Aromatic homopolycyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Naphthalene Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Secondary carboxylic acid amide logp 4.72 ALOGPS logs -5.44 ALOGPS logp 4.32 ChemAxon pka_strongest_acidic 3.08 ChemAxon pka_strongest_basic 5.59 ChemAxon iupac (1R,2S)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-3-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}-6-methoxy-1,2-dihydronaphthalene-2-carboximidic acid ChemAxon average_mass 624.69 ChemAxon mono_mass 624.2472 ChemAxon smiles COC1=C(O)C=CC(=C1)[C@H]1[C@H](C(O)=NCCC2=CC=C(O)C=C2)C(=CC2=CC(OC)=C(O)C=C12)C(=O)NCCC1=CC=C(O)C=C1 ChemAxon formula C36H36N2O8 ChemAxon inchi InChI=1S/C36H36N2O8/c1-45-31-18-23(7-12-29(31)41)33-27-20-30(42)32(46-2)19-24(27)17-28(35(43)37-15-13-21-3-8-25(39)9-4-21)34(33)36(44)38-16-14-22-5-10-26(40)11-6-22/h3-12,17-20,33-34,39-42H,13-16H2,1-2H3,(H,37,43)(H,38,44)/t33-,34-/m1/s1 ChemAxon inchikey XYTYRVFKBJENPE-KKLWWLSJSA-N ChemAxon polar_surface_area 161.07 ChemAxon refractivity 175.08 ChemAxon polarizability 66.83 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 44584134 Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. 28799497 Chen T, Hao J, He J, Zhang J, Li Y, Liu R, Li L: Cannabisin B induces autophagic cell death by inhibiting the AKT/mTOR pathway and S phase cell cycle arrest in HepG2 cells. Food Chem. 2013 Jun 1;138(2-3):1034-41. doi: 10.1016/j.foodchem.2012.11.102. Epub 2012 Dec 5. 23411211 Yan X, Tang J, dos Santos Passos C, Nurisso A, Simoes-Pires CA, Ji M, Lou H, Fan P: Characterization of Lignanamides from Hemp (Cannabis sativa L.) Seed and Their Antioxidant and Acetylcholinesterase Inhibitory Activities. J Agric Food Chem. 2015 Dec 16;63(49):10611-9. doi: 10.1021/acs.jafc.5b05282. Epub 2015 Dec 2. 26585089 Wang S, Luo Q, Fan P: Cannabisin F from Hemp (Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator. Int J Mol Sci. 2019 Jan 25;20(3). pii: ijms20030507. doi: 10.3390/ijms20030507. 30691004 1.0 2020-03-19 00:32:15 UTC 2020-08-04 22:28:17 UTC CDB000348 Pulegone Pulegone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID: 6991645). (+)-(R)-Pulegone (1R)-(+)-p-Menth-4(8)-en-3-one (5R)-2-Isopropylidene-5-methylcyclohexanone (R)-Pulegone D-Pulegone (+)-Pulegone Pulegone, (R)-isomer (R)-(+)-p-Menth-4(8)-en-3-one (R)-p-Menth-4(8)-en-3-one p-Menth-4(8)-en-3-one (R)-5-Methyl-2-(1-methylethylidene)cyclohexanone (R)-(+)-Pulegone (1R)-Pulegone L-Pulegone NSC 15334 Pulegon FEMA 2963 (+)-4(8)-Para-menthen-3-one 5-Methyl-2-(1-methylethylidene)cyclohexanone Pulegone (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone C10H16O 152.23 152.1201 (5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one (+)-pulegone 89-82-7 C[C@@H]1CCC(=C(C)C)C(=O)C1 InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 NZGWDASTMWDZIW-MRVPVSSYSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Cyclic ketones Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Aliphatic homomonocyclic compound Carbonyl group Cyclic ketone Hydrocarbon derivative Ketone Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids p-menth-4(8)-en-3-one logp 3.08 melting_point < 25 °C boiling_point 224 °C Wikipedia logp 2.36 ALOGPS logs -1.82 ALOGPS logp 2.86 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac (5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one ChemAxon average_mass 152.23 ChemAxon mono_mass 152.1201 ChemAxon smiles C[C@@H]1CCC(=C(C)C)C(=O)C1 ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 ChemAxon inchikey NZGWDASTMWDZIW-MRVPVSSYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 47.13 ChemAxon polarizability 18.33 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB030074 442495 C09893 35596 C00000827 Pulegone McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:32:19 UTC 2020-08-04 22:28:17 UTC CDB000349 Viridiflorene Viridiflorene also known as leden, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol (PMID: 7640522). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Viridiflorene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Viridiflorene can be found in a number of plant foods and spices such as allspice, sweet basil, sweet marjoram, eucalyptus, common oregano, sage, thyme and rosemary, which makes viridiflorene a potential biomarker for the consumption of these food products. Viridiflorene is one of more than 140 terpenoids found in cannabis plants (PMID: 6991645). Leden Ledene (+)-Ledene (+)-Viridiflorene C15H24 204.35 204.1878 (1aR,7R,7aS,7bR)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[e]azulene leden 21747-46-6 C[C@@H]1CCC2=C(C)CC[C@@H]3[C@H]([C@H]12)C3(C)C InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10,12-14H,5-8H2,1-4H3/t10-,12-,13-,14-/m1/s1 WGTRJVCFDUCKCM-FMKGYKFTSA-N belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5,10-cycloaromadendrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons 5,10-cycloaromadendrane sesquiterpenoid Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon carbotricyclic compound sesquiterpene logp 3.39 ALOGPS logs -4.24 ALOGPS logp 4.04 ChemAxon iupac (1aR,7R,7aS,7bR)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[e]azulene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CCC2=C(C)CC[C@@H]3[C@H]([C@H]12)C3(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10,12-14H,5-8H2,1-4H3/t10-,12-,13-,14-/m1/s1 ChemAxon inchikey WGTRJVCFDUCKCM-FMKGYKFTSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.5 ChemAxon polarizability 26.12 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10910653 C20162 63444 C00021220 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 1.0 2020-03-19 00:32:22 UTC 2020-08-04 22:28:17 UTC CDB000350 beta-Bisabolol Beta-bisabolol, also known as B-bisabolol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 7640522). However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are two known Bisabolol isomers including Alpha and Beta-bisabolol, which differ in the position of the tertiary alcohol functional group. Beta-bisabolol is a neutral, hydrophobic molecule that is insoluble in water. Beta-bisabolol has a sweet, citrus, floral aroma and a lemon or grapefruit like taste. Industrially, it is used in various fragrances. It has also been used for hundreds of years in cosmetics because of its perceived skin healing properties. Beta-bisabolol is found in a number of plant foods, essential oils and spices including ginger, lemon, black pepper, lavender, and curcumin. Bisabolol has been shown to sensitize pathogenic bacteria to the effects of conventional antibiotics by enhancing the permeability of the bacterial membrane (PMID: 14506058).Beta-bisabolol is one of more than 140 terpenoids found in cannabis plants (PMID: 6991645). b-Bisabolol Β-bisabolol 1-[(1S)-1,5-Dimethyl-4-hexen-1-yl]-4-methyl-(1S)-3-cyclohexen-1-ol 3-Cyclohexen-1-ol, 1-(1,5-dimethyl-4-hexenyl)-4-methyl- (8ci) beta -Bisabolol C15H26O 222.37 222.1984 (1S)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol (1S)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol 15352-77-9 C[C@@H](CCC=C(C)C)[C@]1(O)CCC(C)=CC1 InChI=1S/C15H26O/c1-12(2)6-5-7-14(4)15(16)10-8-13(3)9-11-15/h6,8,14,16H,5,7,9-11H2,1-4H3/t14-,15+/m0/s1 WTVHAMTYZJGJLJ-LSDHHAIUSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol logp 4.77 ALOGPS logs -3.46 ALOGPS logp 3.99 ChemAxon pka_strongest_basic -0.49 ChemAxon iupac (1S)-4-methyl-1-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-en-1-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles C[C@@H](CCC=C(C)C)[C@]1(O)CCC(C)=CC1 ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-12(2)6-5-7-14(4)15(16)10-8-13(3)9-11-15/h6,8,14,16H,5,7,9-11H2,1-4H3/t14-,15+/m0/s1 ChemAxon inchikey WTVHAMTYZJGJLJ-LSDHHAIUSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 72.11 ChemAxon polarizability 27.96 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014957 12300146 C00011606 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Brehm-Stecher BF, Johnson EA: Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone. Antimicrob Agents Chemother. 2003 Oct;47(10):3357-60. doi: 10.1128/aac.47.10.3357-3360.2003. 14506058 1.0 2020-03-19 00:32:25 UTC 2020-09-11 20:08:28 UTC CDB000351 (±)-trans-Nerolidol (¬±)-Trans-nerolidol, also known simply as Trans-nerolidol or penetrol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 7640522). However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. With regard to the production of nerolidol, (E)-nerolidol synthase was recently found to be responsible for the conversion of farnesyl diphosphate (FDP), the universal precursor of sesquiterpenes to (3S)-(E)-nerolidol. Trans-nerolidol is a also member of the class of compounds known as acyclic sesquiterpenoids. Acyclic sesquiterpenoids are sesquiterpenes that do not contain a cycle. There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. (¬±)-Trans-nerolidol is a neutral, hydrophobic molecule that is practically insoluble in water. It exists as a pale, yellow liquid oil. (¬±)-Trans-nerolidol has a woody, fruity citrus aroma reminiscent of citrus, apples and roses. Industrially is used as a food flavoring agen and, a perfuming agent (in shampoos and perfumes). It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520). Statistics have shown that the global usage of nerolidol per annum ranges from 10 to 100 metric tonnes. Trans-nerolidol is being tested as a skin penetration enhancer for the transdermal delivery of therapeutic drugs (PMID: 15855481, 27136520). Trans-nerolidol is a naturally occurring compound found in many plants, foods and spices including ginger, hyssop, lemongrass, jasmine, tea tree, ginger and neroli (an essential oil distilled from bitter orange flowers). As with many terpenoids, it plays a very active role in the defense system of some plants. Trans-nerolidol has been traditionally used for its relaxing, slightly sedative effects. It appears to have anti-parasitic, antifungal and anti-bacterial properties (PMID: 15855481, 27136520). These findings are consistent with the traditional use of orange oil as a natural disinfectant. Trans-nerolidol has been shown to sensitize pathogenic bacteria to the effects of conventional antibiotics by enhancing the permeability of the bacterial membrane (PMID: 14506058). It has also been shown to reduce Leishmaniasis infection by 95% (PMID: 15855481). Trans-nerolidol has also been shown to have anti-ulcer and anti-cancer activity (PMID: 27136520). Trans-Nerolidol is one of more than 140 terpenoids that are known in cannabis plants (PMID: 6991645). (S-(e))-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol Nerolidol Nerolidol, (e)-isomer Nerolidol, (S-(e))-isomer 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol Nerolidol, (S-(Z))-isomer Peruviol Nerolidol, (Z)-isomer (+)-trans-Nerolidol (3S)-(E)-Nerolidol (3S)-trans-Nerolidol (3S,6E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol (3S,6E)-Nerolidol (3S,E)-Nerolidol (S)-(+)-trans-Nerolidol (S)-trans-Nerolidol (S,E)-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol (S,E)-Nerolidol trans-(+)-Nerolidol C15H26O 222.37 222.1984 (3S,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol nerolidol 1119-38-6 CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+/t15-/m1/s1 FQTLCLSUCSAZDY-ATGUSINASA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic acyclic compound Farsesane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol Acyclic farnesane sesquiterpenoids Acyclic farnesane sesquiterpenoids Farnesenes nerolidol logp 4.55 ALOGPS logs -4.02 ALOGPS logp 4.31 ChemAxon pka_strongest_acidic 18.46 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (3S,6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+/t15-/m1/s1 ChemAxon inchikey FQTLCLSUCSAZDY-ATGUSINASA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 74.01 ChemAxon polarizability 28.71 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C09704 59958 4444858 5281525 FDB021837 CPD-12568 C00003166 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. 7640522 Chan WK, Tan LT, Chan KG, Lee LH, Goh BH: Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities. Molecules. 2016 Apr 28;21(5). pii: molecules21050529. doi: 10.3390/molecules21050529. 27136520 Arruda DC, D'Alexandri FL, Katzin AM, Uliana SR: Antileishmanial activity of the terpene nerolidol. Antimicrob Agents Chemother. 2005 May;49(5):1679-87. doi: 10.1128/AAC.49.5.1679-1687.2005. 15855481 Brehm-Stecher BF, Johnson EA: Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone. Antimicrob Agents Chemother. 2003 Oct;47(10):3357-60. doi: 10.1128/aac.47.10.3357-3360.2003. 14506058 1.0 2020-03-19 00:32:28 UTC 2020-09-11 20:08:26 UTC CDB000352 trans-beta-Farnesene (E)-Beta-Farnesene, also known as EBF or trans-beta-Farnesene¬†, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. Œ±-Farnesene and Œ≤-Farnesene are isomers, differing by the location of one double bond. Œ≤-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while¬†Œ±-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. The beta isomer exists as two stereoisomers (cis and trans) about the geometry of its central double bond. However, only the trans isomer exists in nature. Beta-Farnesene exists as a clear colorless liquid and is a hydrophobic, neutral compound that is insoluble in water. It has a woody, sweet, citrus aroma and is used as a masking or perfuming agent. Beta-Farnesene is found naturally in many plants and plant essential oils including basil, blood orange, carrots, celery, ginger, grapefruit, lavender, mint, orange peel, parsley, peppermint, pine, rosemary and thyme. It is one of several sesquiterpenes that are found in cannabis plants (PMID: 6991645).¬†It is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2).¬†Beta-Farnesene is also released by aphids as an alarm pheremone upon death to warn away other aphids (PMID: 21092302) (6E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene (e)-7,11-Dimethyl-3-methylenedodeca-1,6,10-triene beta-Farnesene beta-trans-Farnesene trans-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene b-Farnesene Β-farnesene b-trans-Farnesene Β-trans-farnesene (e)-b-Farnesene (e)-Β-farnesene (E)-beta-Farnesene trans-b-Farnesene trans-β-Farnesene (E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene trans-beta-Farnesene C15H24 204.36 204.1878 (6E)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene β-farnesene 18452-58-9 CC(C)=CCC\C(C)=C\CCC(=C)C=C InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12+ JSNRRGGBADWTMC-NTCAYCPXSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Alkatetraenes Branched unsaturated hydrocarbons Unsaturated aliphatic hydrocarbons Acyclic olefin Aliphatic acyclic compound Alkatetraene Branched unsaturated hydrocarbon Farsesane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Farnesenes Hydrocarbons beta-farnesene water_solubility 3.38e-03 g/l ALOGPS logp 5.70 ALOGPS logp 5.70 ALOGPS logs -4.78 ALOGPS logp 5.2 ChemAxon iupac (6E)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC\C(C)=C\CCC(=C)C=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9,12H,1,4,7-8,10-11H2,2-3,5H3/b15-12+ ChemAxon inchikey JSNRRGGBADWTMC-NTCAYCPXSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 72.18 ChemAxon polarizability 26.89 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C09666 5281517 10418 C00003131 CPD-8239 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kunert G, Reinhold C, Gershenzon J: Constitutive emission of the aphid alarm pheromone, (E)-beta-farnesene, from plants does not serve as a direct defense against aphids. BMC Ecol. 2010 Nov 23;10:23. doi: 10.1186/1472-6785-10-23. 21092302 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:32:34 UTC 2020-07-24 23:30:19 UTC CDB000354 Henicosane Heneicosane, also known as cH3-[cH2]19-cH3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, heneicosane is considered to be a hydrocarbon lipid molecule. Heneicosane is an alkane and waxy tasting compound and can be found in a number of food items such as orange bell pepper, yellow bell pepper, lemon balm, and pepper (c. annuum), which makes heneicosane a potential biomarker for the consumption of these food products. The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions . Henicosane is possibly neutral. Henicosane is one of many hydrocarbons that are known in cannabis plants (PMID: 6991645). C41H86 579.14 578.673 henicosane; icosane eicosane; heneicosane 629-94-7 CCCCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCCCC InChI=1S/C21H44.C20H42/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2;1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3;3-20H2,1-2H3 SWXDIPSJIVFXHL-UHFFFAOYSA-N logp 9.98 ALOGPS logs -7.69 ALOGPS logp 9.8 ChemAxon iupac henicosane; icosane ChemAxon average_mass 579.14 ChemAxon mono_mass 578.673 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCCCC ChemAxon formula C41H86 ChemAxon inchi InChI=1S/C21H44.C20H42/c1-3-5-7-9-11-13-15-17-19-21-20-18-16-14-12-10-8-6-4-2;1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-21H2,1-2H3;3-20H2,1-2H3 ChemAxon inchikey SWXDIPSJIVFXHL-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 98.42 ChemAxon polarizability 44.09 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 129818893 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:32:37 UTC 2020-08-04 22:28:17 UTC CDB000355 Hentriacontane Hentriacontane, also known as untriacontane, is a long-chain hydrocarbon containing 31 carbons. It belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, hentriacontane is considered to be a hydrocarbon lipid molecule. Hentriacontane is a very hydrophobic molecule, insoluble in water, and fully neutral. It exists as a clear, waxy solid. Hentriacontane is found naturally in a number of common plants and foods including the common pea, gum arabic (acacia senegal), grapes, watermelons, papaya, coconuts, and sunflowers. It also comprises about 8-9% of beeswax.¬†Hentriacontane has also been found to be a major component of Candelilla wax. Candelilla wax is a wax derived from the leaves of the small Candelilla shrub native to northern Mexico and the southwestern United States. The Candelilla shrub is a member of the Euphorbia plant genus, from the family Euphorbiaceae. Candelilla wax is used as a food additive and is used as a glazing agent. It also used in cosmetic industry, as a component of lip balms and lotion bars. One of its major uses is as a binder for chewing gums. Candelilla wax can be used as a substitute for carnauba wax and beeswax. It is also used for making varnish. Hentriacontane is one of many alkanes that are known in cannabis plants (PMID: 6991645). Hentriacontane is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Hentriacontane has been shown to have anti-inflammatory effects. In particular, hentriacontane ameliorates the expression of inflammatory mediators (TNF-Œ±, IL-6, PGE(2), COX-2 and iNOS) and the activation of NF-Œ∫B and caspase-1 in LPS-stimulated peritoneal macrophages (PMID: 21394806). Hentriacontane is also thought to have antitumor and antimicrobial activities (PMID: 28549290). CH3-[CH2]29-CH3 Hentriacontan N-Hentriacontane C31H64 436.84 436.5008 hentriacontane hentriacontane 630-04-6 CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C31H64/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-31H2,1-2H3 IUJAMGNYPWYUPM-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane Hydrocarbons an alkane long-chain alkane melting_point 67.9 °C boiling_point 458 °C Wikipedia logp 11.01 ALOGPS logs -8.02 ALOGPS logp 14.25 ChemAxon iupac hentriacontane ChemAxon average_mass 436.84 ChemAxon mono_mass 436.5008 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC ChemAxon formula C31H64 ChemAxon inchi InChI=1S/C31H64/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-31H2,1-2H3 ChemAxon inchikey IUJAMGNYPWYUPM-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 144.43 ChemAxon polarizability 65.61 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB001480 11904 12410 C08376 5659 C00001250 CPD-7937 Hentriacontane Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kim SJ, Chung WS, Kim SS, Ko SG, Um JY: Antiinflammatory effect of Oldenlandia diffusa and its constituent, hentriacontane, through suppression of caspase-1 activation in mouse peritoneal macrophages. Phytother Res. 2011 Oct;25(10):1537-46. doi: 10.1002/ptr.3443. Epub 2011 Mar 11. 21394806 Khajuria V, Gupta S, Sharma N, Kumar A, Lone NA, Khullar M, Dutt P, Sharma PR, Bhagat A, Ahmed Z: Anti-inflammatory potential of hentriacontane in LPS stimulated RAW 264.7 cells and mice model. Biomed Pharmacother. 2017 Aug;92:175-186. doi: 10.1016/j.biopha.2017.05.063. Epub 2017 May 23. 28549290 1.0 2020-03-19 00:32:49 UTC 2020-08-04 22:28:17 UTC CDB000359 Muscarine Muscarine or (2S,4R,5S)-Muscarine, L-(+)-muscarine, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Muscarine is also a quaternary ammonium salt that is soluble in water. Muscarine is also a proto alkaloid, a class of nitrogenous organic compounds of plant origin¬†with pronounced effects on humans. It is a natural product of some mushroom species, particularly in the genera Inocybe and Clitocybe (PMID: 27714029). Muscarine is also found in cannabis plants (PMID: 6991645). Muscarine can cause profound activation of the¬†peripheral¬†parasympathetic nervous system¬†that may end in circulatory collapse and death. Muscarine is a nonselective agonist of the muscarinic acetylcholine receptors. Muscarine and muscarine agonists are used for the treatment of glaucoma, urinary retention, postoperative ileus, xerostomia and congenital megacolon. However, muscarine and its agonists are contraindicated for those who are sensitive to parasympathetic stimulation such as people with asthma, Chronic Obstructive Pulmonary disease (COPD), peptic ulcer disease or those with obstructions to the gastrointestinal tract or urinary tract. Muscarine is not metabolized by the body and is removed by renal clearance. Muscarin L-(+)-Muscarine C9H20NO2 174.26 174.1489 {[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium (+)-muscarine 300-54-9 C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1 UQOFGTXDASPNLL-XHNCKOQMSA-N belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Pentoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Amines Dialkyl ethers Hydrocarbon derivatives Organic cations Organic salts Organopnictogen compounds Oxacyclic compounds Secondary alcohols Tetraalkylammonium salts Tetrahydrofurans Alcohol Aliphatic heteromonocyclic compound Amine Dialkyl ether Ether Hydrocarbon derivative Organic cation Organic nitrogen compound Organic salt Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Pentose monosaccharide Quaternary ammonium salt Secondary alcohol Tetraalkylammonium salt Tetrahydrofuran Alkaloids monosaccharide logp -2.98 ALOGPS logs -2.51 ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 14.11 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac {[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium ChemAxon average_mass 174.26 ChemAxon mono_mass 174.1489 ChemAxon smiles C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O ChemAxon formula C9H20NO2 ChemAxon inchi InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1 ChemAxon inchikey UQOFGTXDASPNLL-XHNCKOQMSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 59.89 ChemAxon polarizability 20.1 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 9308 C07473 C00001422 Jin Z: Muscarine, imidazole, oxazole and thiazole alkaloids. Nat Prod Rep. 2016 Oct 26;33(11):1268-1317. doi: 10.1039/c6np00067c. 27714029 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:32:52 UTC 2020-06-19 18:40:59 UTC CDB000360 Isoleucine betaine Isoleucine betaine is a naturally occurring organic compound isolated from the ethanol extract of cannabis seeds. It is classified as a quaternary base. The structure was determined by spectroscopic methods and confirmed by synthesis (https://doi.org/10.1016/0031-9422(73)80454-6). Isoleucine betaine is a quaternary ammonium salt with three methyl groups and one carboxyl group attached to the nitrogen atom via C-2. Isoleucine betaine is a betaine base compound was first isolated and identified as a cannabis constituent in 1973 (PMID:6991645). (2R)-2-(Trimethylazaniumyl)butanoic acid C7H15NO2 145.2 145.1103 (2R)-2-(trimethylazaniumyl)butanoate (2R)-2-(trimethylammonio)butanoate CC[C@H](C([O-])=O)[N+](C)(C)C InChI=1S/C7H15NO2/c1-5-6(7(9)10)8(2,3)4/h6H,5H2,1-4H3/t6-/m1/s1 JWNWCEAWZGLYTE-ZCFIWIBFSA-N logp -2.20 ALOGPS logs -2.94 ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 2.5 ChemAxon iupac (2R)-2-(trimethylazaniumyl)butanoate ChemAxon average_mass 145.2 ChemAxon mono_mass 145.1103 ChemAxon smiles CC[C@H](C([O-])=O)[N+](C)(C)C ChemAxon formula C7H15NO2 ChemAxon inchi InChI=1S/C7H15NO2/c1-5-6(7(9)10)8(2,3)4/h6H,5H2,1-4H3/t6-/m1/s1 ChemAxon inchikey JWNWCEAWZGLYTE-ZCFIWIBFSA-N ChemAxon polar_surface_area 40.13 ChemAxon refractivity 61.84 ChemAxon polarizability 15.85 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:32:55 UTC 2020-08-04 22:28:17 UTC CDB000361 Moupinamide Moupinamide, also known as Alfrutamide or N-feruloyltyramine or N-trans-feruloyltyramine (NTF), belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is also classified as a phenylpropanoid amide. Phenylpropanoids consist of a six-carbon, aromatic phenyl group and a three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. A phenylpropanoid amide has an amide group incorporated into its propanoid chain. There are two known isomers of N-Feruloyltyramine, N-trans-Feruloyltyramine and N-cis-Feruloyltyramine. Moupinamide is a largely neutral molecule, that is somewhat insoluble in water. It exists as a pale yellow oil. Moupinamide or N-trans-Feruloyltyramine is found in black and white peppers. N-cis-Feruloyltyramine has been identified in yellow bell peppers, red bell peppers and in a lower concentration in orange bell peppers, green bell peppers, celery leaves, hyssops, quinoa, agars, and oxheart cabbages. N-trans-feruloyltyramine (Moupinamide) is one of the major phenylpropanoid amides that have been identified in the cannabis plant (PMID:6991645). Moupinamide is an inhibitor of COX 1 and COX 2 and has potential antioxidant properties (PMID: 19807156) N-[(e)-Feruloyl]tyramine trans-N-Feruloyltyramine (2,3)trans-N-(p-Hydroxyphenethyl)ferulamide Feruloyltyramine N-Feruloyltyramine N-trans-Feruloyltyramine Feruloyltyramine, (Z)-isomer Feruloyltyramine, (e)-isomer Moupinamide C18H19NO4 313.35 313.1314 (Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid 66648-43-9 COC1=C(O)C=CC(\C=C\C(\O)=N\CCC2=CC=C(O)C=C2)=C1 InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+ NPNNKDMSXVRADT-WEVVVXLNSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyphenols Organic compounds Benzenoids Phenols Methoxyphenols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carboximidic acids Hydrocarbon derivatives Methoxybenzenes Organonitrogen compounds Organopnictogen compounds Phenoxy compounds Propargyl-type 1,3-dipolar organic compounds Styrenes 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Carboximidic acid Carboximidic acid derivative Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic 1,3-dipolar compound Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol ether Phenoxy compound Propargyl-type 1,3-dipolar organic compound Styrene tyramines melting_point 144.5 - 145 °C logp 2.46 ALOGPS logs -4.37 ALOGPS logp 3.05 ChemAxon pka_strongest_acidic 4.41 ChemAxon pka_strongest_basic 6.38 ChemAxon iupac (Z,2E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid ChemAxon average_mass 313.35 ChemAxon mono_mass 313.1314 ChemAxon smiles COC1=C(O)C=CC(\C=C\C(\O)=N\CCC2=CC=C(O)C=C2)=C1 ChemAxon formula C18H19NO4 ChemAxon inchi InChI=1S/C18H19NO4/c1-23-17-12-14(4-8-16(17)21)5-9-18(22)19-11-10-13-2-6-15(20)7-3-13/h2-9,12,20-21H,10-11H2,1H3,(H,19,22)/b9-5+ ChemAxon inchikey NPNNKDMSXVRADT-WEVVVXLNSA-N ChemAxon polar_surface_area 82.28 ChemAxon refractivity 90.09 ChemAxon polarizability 34.56 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000432 4444168 C02717 17818 5280537 C00000660 CPD-440 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Park JB: Isolation and characterization of N-feruloyltyramine as the P-selectin expression suppressor from garlic (Allium sativum). J Agric Food Chem. 2009 Oct 14;57(19):8868-72. doi: 10.1021/jf9018382. 19807156 1.0 2020-03-19 00:33:02 UTC 2020-08-04 22:28:17 UTC CDB000363 N-trans-Caffeoyltyramine N-Trans-Caffeoyltyramine also known as trans-N-Caffeoyltyramine or TNC, belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing a cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. It is also classified as a phenylpropanoid amide. Phenylpropanoids consist of a six-carbon, aromatic phenyl group and a three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. A phenylpropanoid amide has an amide group incorporated into its propanoid chain. There are two known isomers of N-Caffeoyltyramine, N-trans-Caffeoyltyramine and N-cis-Caffeoyltyramine. N-Trans-Caffeoyltyramine is a largely neutral molecule, that is somewhat insoluble in water. N-trans-caffeoyltyramine is one of the major phenylpropanoid amides that have been identified in the cannabis plant (PMID:6991645). N-trans-Caffeoyltyramine has both arginase inhibitory properties and a strong antioxidant capacity (DOI: 10.1055/s-0042-119400). These properties may make it useful for the design and development of new drugs for the treatment of endothelial dysfunction associated with cardiovascular diseases. N-Caffeoyltyramine has exhibited anti-cancer activities and appears to inhibit the epidermal growth factor receptor (EGFR) and its protein tyrosine kinase activity. In addition, N-Caffeoyltyramine appears to activate caspase 3 activity (PMID: 14643446) trans-N-Caffeoyltyramine (2E)-3-(3,4-Dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidate N-Caffeoyltyramine C17H17NO4 299.32 299.1158 (E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid 219773-48-5 O\C(\C=C\C1=CC(O)=C(O)C=C1)=N\CCC1=CC=C(O)C=C1 InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+ VSHUQLRHTJOKTA-XBXARRHUSA-N belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. Hydroxycinnamic acids and derivatives Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Carbonyl compounds Catechols Cinnamic acid amides Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid derivative Catechol Cinnamic acid amide Hydrocarbon derivative Hydroxycinnamic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Secondary carboxylic acid amide Styrene logp 2.26 ALOGPS logs -3.90 ALOGPS logp 2.92 ChemAxon pka_strongest_acidic 4.36 ChemAxon pka_strongest_basic 6.32 ChemAxon iupac (E,2E)-3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid ChemAxon average_mass 299.32 ChemAxon mono_mass 299.1158 ChemAxon smiles O\C(\C=C\C1=CC(O)=C(O)C=C1)=N\CCC1=CC=C(O)C=C1 ChemAxon formula C17H17NO4 ChemAxon inchi InChI=1S/C17H17NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-8,11,19-21H,9-10H2,(H,18,22)/b8-4+ ChemAxon inchikey VSHUQLRHTJOKTA-XBXARRHUSA-N ChemAxon polar_surface_area 93.28 ChemAxon refractivity 85.61 ChemAxon polarizability 31.73 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 8170478 FDB011018 9994897 DB08754 Y13 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Park JB, Schoene N: N-Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3. Cancer Lett. 2003 Dec 30;202(2):161-71. doi: 10.1016/j.canlet.2003.08.010. 14643446 1.0 2020-03-19 00:33:10 UTC 2020-08-04 22:28:17 UTC CDB000366 Rhamnose Rhamnose (Rham) is a naturally occurring deoxy sugar that is structurally derived from mannose. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. It is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moiety. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose exists in two anomeric forms, alpha-L-rhamnose and beta-L- Rhamnose. Rhamnose is often bound to other sugars in nature. It is a common glycone component of many glycosides (such as phenolic glycosides) from many plants. In particular, rhamnose can be isolated from a number of plants including Buckthorn (Rhamnus), poison sumac, and various plants in the genus Uncaria. Rhamnose is moderately sweet, having a sweetness rating of about 33% of sucrose. Sweetness is detected through the binding of sugars to the T1R3 and T1R2 proteins, to form a G-protein coupled receptor that is the sweetness receptor in mammals. In addition to being found in plants, rhamnose is also a component of the outer cell membrane (especially of the lipopolysaccharides) of certain gram-negative bacteria including Klebsiella and Pseudomonas (https://link.springer.com/article/10.1007/BF00369505) as well as certain strains of Mycobacteria. L-rhamnose is metabolized to L-lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. Rhamnose is also one of many sugars that are found in cannabis plants (PMID: 6991645). alpha-6-Deoxy-L-mannose alpha-L-Mannomethylose alpha-L-Rha alpha-L-Rhamnose alpha-L-Rhap alpha-L-Rhamnopyranose a-6-Deoxy-L-mannose Α-6-deoxy-L-mannose a-L-Mannomethylose Α-L-mannomethylose a-L-Rha Α-L-rha a-L-Rhamnose Α-L-rhamnose a-L-Rhap Α-L-rhap a-L-Rhamnopyranose C6H12O5 164.16 164.0685 (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol α-L-rhamnopyranose 10030-85-0 C[C@@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6+/m0/s1 SHZGCJCMOBCMKK-HGVZOGFYSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Oxanes Polyols Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Hemiacetal Hexose monosaccharide Hydrocarbon derivative Organoheterocyclic compound Oxacycle Oxane Polyol Secondary alcohol L-rhamnopyranose melting_point 91 to 93 °C Wikipedia logp -2.39 ALOGPS logs 0.70 ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 11.3 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol ChemAxon average_mass 164.16 ChemAxon mono_mass 164.0685 ChemAxon smiles C[C@@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@H]1O ChemAxon formula C6H12O5 ChemAxon inchi InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6+/m0/s1 ChemAxon inchikey SHZGCJCMOBCMKK-HGVZOGFYSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 34.38 ChemAxon polarizability 15.26 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C02476 439710 27907 C00001129 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:33:19 UTC 2020-08-04 22:28:17 UTC CDB000368 Quebrachitol Quebrachitol or L-Quebrachitol or QCT, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Quebrachitol can also be classified as a cyclitol (a cyclic polyol). L-Quebrachitol is an optically active, hydrophilic, neutral molecule that is very water soluble. It exists as a white powder. It was first isolated in 1887 from the bark of Aspidosperma quebracho (a South American rubber tree species), from whence it received its name. Quebrachitol along with sucrose is one of the main sugars in the latex of rubber trees. Quebrachitol is a natural product that is found in a number of plants and plant foods, with the highest concentration being found in sea-buckthorn berries. L-Quebrachitol has also been detected, but not quantified in litchi, mugworts and in Cannabis sativa (PMID: 6991645). It shows a sweetening property half of that of sucrose but induces colic or diarrhea at concentration used to render the food palatable. Quebrachito has been shown to have gastroprotective effects against acute gastric lesions caused by NSAIDs (PMID: 28132388). It also acts as a platelet activating factor (PAF) inhibitor and binds to the platelet activating factor receptor (PAFR) at micromolar concentrations (PMID: 21060292). Quebrachito also appears to bind to a number of other proteins or protein targets including the IP3 receptor, Œ≤-glucosidase, PAFR, COX2, nitric oxide synthase, and K+ATP channels (PMID: 28132388). C7H14O6 194.18 194.079 (1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol (1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol 642-38-6 CO[C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3+,4-,5-,6-,7-/m0/s1 DSCFFEYYQKSRSV-OUIVRQFQSA-N belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Cyclohexanols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic homomonocyclic compounds Cyclitols and derivatives Dialkyl ethers Hydrocarbon derivatives Polyols Aliphatic homomonocyclic compound Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl ether Ether Hydrocarbon derivative Polyol melting_point 190 to 198 °C Wikipedia logp -2.67 ALOGPS logs 0.45 ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 12.36 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (1S,2R,3S,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol ChemAxon average_mass 194.18 ChemAxon mono_mass 194.079 ChemAxon smiles CO[C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C7H14O6 ChemAxon inchi InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3+,4-,5-,6-,7-/m0/s1 ChemAxon inchikey DSCFFEYYQKSRSV-OUIVRQFQSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 40.53 ChemAxon polarizability 18.03 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Wang D, Zhang S, Chang Z, Kong DX, Zuo Z: Quebrachitol: Global Status and Basic Research. Nat Prod Bioprospect. 2017 Feb;7(1):113-122. doi: 10.1007/s13659-017-0120-3. Epub 2017 Jan 28. 28132388 Moharam BA, Jantan I, Jalil J, Shaari K: Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation. Molecules. 2010 Nov 3;15(11):7840-8. doi: 10.3390/molecules15117840. 21060292 1.0 2020-03-19 00:33:21 UTC 2020-08-04 22:28:17 UTC CDB000369 Galactosamine Galactosamine or D-galactosamine, also known as D-chondrosamine or 2-amino-2-deoxy-D-galactose, is a hexosamine derived from galactose. It is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-galactosamine is soluble in water and a relatively strong base (based on its pKa). Galactosamine is a ubiquitous compound found in bacteria, plants and animals. Galactosamine is one of several aminosugars found in cannabis plants (PMID: 6991645). Evidently Cannabis sativa is one of only a handful of higher plants that synthesizes galactosamine. In humans, galactosamine is an asparagine-linked constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH). An important derivative of galactosamine is N-acetyl-galactosamine, which is a major component of chondroitin and chondroitin sulfate (cartilage). Galactosamine is also used in the synthesis of bacterial cell walls (especially in the synthesis of the lipopolysaccharide or O-antigen) in streptococci bacteria (PMID: 4629249). Galactosamine is a hepatotoxin and is sometimes used either alone or in combination with lipopolysaccharide (LPS) in rodent models to induce liver failure (PMID: 12625810). Galactosamine induces depletion of UTP, UDP and UMP selectively, which is essential for RNA and protein synthesis. RNA and protein synthesis is especially high in metabolically actives tissues such as the liver, which partly explains the toxicity of galactosamine to these tissues (PMID: 11051199). Galactosamine is metabolized via the Leloir pathway of galactose metabolism, which generates dead-end uridine derivatives of galactosamine. UDP-galactosamine (and by inference, galactosamine) is an inhibitor of UDP-galactose-4‚Ä≤ epimerase. D-Chondrosamine D-Galactosamine D-GalN Galactosamine C6H13NO5 179.17 179.0794 (2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal D-galactosamine 7535-00-4 N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)CO InChI=1S/C6H13NO5/c7-3(1-8)5(11)6(12)4(10)2-9/h1,3-6,9-12H,2,7H2/t3-,4+,5+,6-/m0/s1 FZHXIRIBWMQPQF-KCDKBNATSA-N belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Hexoses Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds 1,3-aminoalcohols Aminosaccharides Beta-hydroxy aldehydes Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Polyols Primary alcohols Secondary alcohols 1,3-aminoalcohol Alcohol Aldehyde Aliphatic acyclic compound Amine Amino saccharide Beta-hydroxy aldehyde Carbonyl group Hexose monosaccharide Hydrocarbon derivative Organic nitrogen compound Organic oxide Organonitrogen compound Organopnictogen compound Polyol Primary alcohol Primary aliphatic amine Primary amine Secondary alcohol D-galactosamine melting_point 180 °C Wikipedia logp -2.63 ALOGPS logs 0.04 ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 12.77 ChemAxon pka_strongest_basic 6.86 ChemAxon iupac (2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal ChemAxon average_mass 179.17 ChemAxon mono_mass 179.0794 ChemAxon smiles N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)CO ChemAxon formula C6H13NO5 ChemAxon inchi InChI=1S/C6H13NO5/c7-3(1-8)5(11)6(12)4(10)2-9/h1,3-6,9-12H,2,7H2/t3-,4+,5+,6-/m0/s1 ChemAxon inchikey FZHXIRIBWMQPQF-KCDKBNATSA-N ChemAxon polar_surface_area 124.01 ChemAxon refractivity 39 ChemAxon polarizability 16.57 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 2794221 60313 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Mukasa H, Slade HD: Chemical composition and immunological specificity of the streptococcal group O cell wall polysaccharide antigen. Infect Immun. 1972 May;5(5):707-14. 4629249 Ferencikova R, Cervinkova Z, Drahota Z: Hepatotoxic effect of D-galactosamine and protective role of lipid emulsion. Physiol Res. 2003;52(1):73-8. 12625810 Kmiec Z, Smolenski RT, Zych M, Mysliwski A: The effects of galactosamine on UTP levels in the livers of young, adult and old rats. Acta Biochim Pol. 2000;47(2):349-53. 11051199 1.0 2020-03-19 00:33:25 UTC 2020-11-04 16:20:30 UTC CDB000370 Apigenin Apigenin, also known as chamomile or versulin, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Apigenin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It exists as a yellow crystalline solid that has been used to dye wool. Apigenin is abundantly found in fruits and vegetables including parsley, celery and chamomile tea. Apigenin is also one of 23 flavonoids that are found in cannabis plants (PMID: 6991645). It exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. Apigenin has shown significant promise as a skin cancer chemopreventive agent. In particular, apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311 (PMID: 16982614). Apigenin provides selective activity to promote caspase-dependent-apoptosis of leukemia cells (PMID: 16844095). Apigenin induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells (PMID: 16648565). Apigenin is biosynthetically derived from the general phenylpropanoid pathway. The phenylpropanoid pathway starts from the aromatic amino acids L-phenylalanine or L-tyrosine, both products of the Shikimate pathway. L-phenylalanine is deaminated by phenylalanine ammonia lyase (PAL) to make cinnamate, followed by oxidation at the para position by cinnamate 4-hydroxylase (C4H) to produce p-coumarate. 4-coumarate CoA ligase (4CL) then substitutes coenzyme A (CoA) at the carboxy group of p-coumarate. Later chalcone synthase (CHS) uses consecutive condensations of three equivalents of malonyl CoA followed by aromatization to convert p-coumaroyl-CoA to chalcone. Chalcone isomerase (CHI) then isomerizes the product to close the pyrone ring to make naringenin. Finally, a flavanone synthase (FNS) enzyme oxidizes naringenin to apigenin (PMID: 12636085, 11524111) 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone 4',5,7-Trihydroxyflavone 5,7,4'-Trihydroxyflavone 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one C.I. natural yellow 1 Chamomile Spigenin Versulin 4',5,7-Trihydroxy-flavone 4,5, 7-Trihydroxyflavone 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one Apigenol 4’,5,7-Trihydroxyflavone 5,7,4’-Trihydroxyflavone 5,7-Dihydroxy-2-(4-Hydroxyphenyl)chromen-4-one 5,7-Dihydroxy-2-p-hydroxyphenyl-4-chromenone Apegenin Apigenin Apigenine C15H10O5 270.24 270.0528 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one chamomile 461015-54-3 OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H KZNIFHPLKGYRTM-UHFFFAOYSA-N belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Flavones Organic compounds Phenylpropanoids and polyketides Flavonoids Flavones Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives Chromones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organooxygen compounds Oxacyclic compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Flavone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Pyran Pyranone Vinylogous acid Flavones and Flavonols Flavones and Flavonols flavones trihydroxyflavone logp 3.02 PERRISSOUD,D & TESTA,B (1986) melting_point 347.5 °C logp 3.07 ALOGPS logs -3.36 ALOGPS logp 2.71 ChemAxon pka_strongest_acidic 6.57 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one ChemAxon average_mass 270.24 ChemAxon mono_mass 270.0528 ChemAxon smiles OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1 ChemAxon formula C15H10O5 ChemAxon inchi InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H ChemAxon inchikey KZNIFHPLKGYRTM-UHFFFAOYSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 72.91 ChemAxon polarizability 26.78 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB07352 FDB002798 4444100 C01477 5280443 18388 228 C00003817 CPD-431 Apigenin 3397 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Balasubramanian S, Zhu L, Eckert RL: Apigenin inhibition of involucrin gene expression is associated with a specific reduction in phosphorylation of protein kinase Cdelta Tyr311. J Biol Chem. 2006 Nov 24;281(47):36162-72. doi: 10.1074/jbc.M605368200. Epub 2006 Sep 18. 16982614 Vargo MA, Voss OH, Poustka F, Cardounel AJ, Grotewold E, Doseff AI: Apigenin-induced-apoptosis is mediated by the activation of PKCdelta and caspases in leukemia cells. Biochem Pharmacol. 2006 Sep 14;72(6):681-92. doi: 10.1016/j.bcp.2006.06.010. Epub 2006 Jul 17. 16844095 Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Sakai T: The dietary flavonoid apigenin sensitizes malignant tumor cells to tumor necrosis factor-related apoptosis-inducing ligand. Mol Cancer Ther. 2006 Apr;5(4):945-51. doi: 10.1158/1535-7163.MCT-05-0431. 16648565 Austin MB, Noel JP: The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep. 2003 Feb;20(1):79-110. doi: 10.1039/b100917f. 12636085 Martens S, Forkmann G, Matern U, Lukacin R: Cloning of parsley flavone synthase I. Phytochemistry. 2001 Sep;58(1):43-6. doi: 10.1016/s0031-9422(01)00191-1. 11524111 1.0 2020-03-19 00:33:29 UTC 2020-07-08 16:06:16 UTC CDB000371 Luteolin Luteolin, also known as digitoflavone or flacitran, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, luteolin is considered to be a flavonoid lipid molecule. Luteolin is a naturally occurring flavonoid. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. Luteolin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Luteolin is one of the Flavonoids that have been found in the cannabis plant. (PMID: 6991645) 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one 3',4',5,7-Tetrahydroxyflavone 5,7,3',4'-Tetrahydroxyflavone Digitoflavone Flacitran Luteolol Salifazide 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyrone-4-one 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one Luteoline 3',4',5,7-Tetrahydroxy-flavone 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-benzopyran-4-one 3’,4’,5,7-Tetrahydroxyflavone 5,7,3’,4’-Tetrahydroxyflavone Cyanidenon C15H10O6 286.24 286.0477 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one luteolin 491-70-3 OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1 InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H IQPNAANSBPBGFQ-UHFFFAOYSA-N belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Flavones Organic compounds Phenylpropanoids and polyketides Flavonoids Flavones Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives Catechols Chromones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Organooxygen compounds Oxacyclic compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Flavone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Pyran Pyranone Vinylogous acid 3'-hydroxyflavonoid Flavones and Flavonols Flavones and Flavonols flavones tetrahydroxyflavone logp 2.53 PERRISSOUD,D & TESTA,B (1986) melting_point 329.5 °C logp 2.73 ALOGPS logs -3.32 ALOGPS logp 2.4 ChemAxon pka_strongest_acidic 6.57 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one ChemAxon average_mass 286.24 ChemAxon mono_mass 286.0477 ChemAxon smiles OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1 ChemAxon formula C15H10O6 ChemAxon inchi InChI=1S/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H ChemAxon inchikey IQPNAANSBPBGFQ-UHFFFAOYSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 74.89 ChemAxon polarizability 27.73 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4444102 FDB013255 5280445 C01514 LU2 15864 229 C00000674 5734-TETRAHYDROXYFLAVONE Luteolin 1.0 2020-03-19 00:33:33 UTC 2020-11-04 16:20:30 UTC CDB000372 Quercetin Quercetin, also known as sophoretin or xanthaurine, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Quercetin is an antioxidant, like many other phenolic heterocyclic compounds. Quercetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Quercetin is one of 23 flavonoids found in cannabis plants (PMID: 6991645). Quercetin is a widely distributed flavonoid found in many other plants and fruits including red grapes, citrus fruit, tomatoes, broccoli, red onions, kale, various leafy green vegetables, and a number of berries, including raspberries and cranberries. In plants quercetin functions as a naturally occurring polar auxin transport inhibitor (PMID: 12237347). Quercetin has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods. Quercetin itself (the aglycone), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. In the human body quercetin functions as a non-specific protein kinase enzyme inhibitor (PMID: 15019969). It also acts as a phytoestrogen and has been reported to have estrogenic activities by activating both estrogen receptor alpha (ER alpha) and estrogen beta (ER beta) (PMID: 17724002). In human breast cancer cell lines, quercetin has been found to act as an agonist of the G protein-coupled estrogen receptor (GPER) (PMID: 15090535). Despite these many known interactions with human proteins, quercetin has not been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. In particular, the U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, there is a clear inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions. (PMID: 17015250). 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one 3,3',4',5,7-Pentahydroxyflavone 3,5,7,3',4'-Pentahydroxyflavone Sophoretin Xanthaurine 3,3',4,5,7-Pentahydroxyflavone 2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one 3',4',5,7-Tetrahydroxyflavan-3-ol 3',4',5,7-Tetrahydroxyflavon-3-ol 3,4',5,5',7-Pentahydroxy-flavone 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-ON Flavin meletin Meletin Quercetin dihydrate Quercetol Quertin Dikvertin 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one 3,3’,4’,5,7-Pentahydroxyflavone 3,5,7,3’,4’-Pentahydroxyflavone 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one 3'-Hydroxykaempferol 3’-Hydroxykaempferol Quercetine Quertine C15H10O7 302.24 302.0427 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one quercetin 73123-10-1 OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1 InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H REFJWTPEDVJJIY-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Flavonols Organic compounds Phenylpropanoids and polyketides Flavonoids Flavones Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives Catechols Chromones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Oxacyclic compounds Polyols Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3'-hydroxyflavonoid 3-hydroxyflavone 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Catechol Chromone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Pyran Pyranone Vinylogous acid 7-hydroxyflavonol Flavones and Flavonols Flavones and Flavonols flavonols pentahydroxyflavone water_solubility 0.06 mg/mL at 16 °C melting_point 316 - 318 °C logp 1.81 ALOGPS logs -3.06 ALOGPS logp 2.16 ChemAxon pka_strongest_acidic 6.38 ChemAxon pka_strongest_basic -4 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one ChemAxon average_mass 302.24 ChemAxon mono_mass 302.0427 ChemAxon smiles OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1 ChemAxon formula C15H10O7 ChemAxon inchi InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H ChemAxon inchikey REFJWTPEDVJJIY-UHFFFAOYSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 76.86 ChemAxon polarizability 28.54 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB011904 DB04216 291 4444051 5280343 QUE 16243 C00389 CPD-520 C00004631 Quercetin Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Fischer C, Speth V, Fleig-Eberenz S, Neuhaus G: Induction of Zygotic Polyembryos in Wheat: Influence of Auxin Polar Transport. Plant Cell. 1997 Oct;9(10):1767-1780. doi: 10.1105/tpc.9.10.1767. 12237347 Williams RJ, Spencer JP, Rice-Evans C: Flavonoids: antioxidants or signalling molecules? Free Radic Biol Med. 2004 Apr 1;36(7):838-49. doi: 10.1016/j.freeradbiomed.2004.01.001. 15019969 Moutsatsou P: The spectrum of phytoestrogens in nature: our knowledge is expanding. Hormones (Athens). 2007 Jul-Sep;6(3):173-93. 17724002 Maggiolini M, Vivacqua A, Fasanella G, Recchia AG, Sisci D, Pezzi V, Montanaro D, Musti AM, Picard D, Ando S: The G protein-coupled receptor GPR30 mediates c-fos up-regulation by 17beta-estradiol and phytoestrogens in breast cancer cells. J Biol Chem. 2004 Jun 25;279(26):27008-16. doi: 10.1074/jbc.M403588200. Epub 2004 Apr 16. 15090535 Perez-Vizcaino F, Duarte J, Andriantsitohaina R: Endothelial function and cardiovascular disease: effects of quercetin and wine polyphenols. Free Radic Res. 2006 Oct;40(10):1054-65. doi: 10.1080/10715760600823128. 17015250 1.0 2020-03-19 00:33:39 UTC 2020-11-04 16:20:30 UTC CDB000373 Kaempferol Kaempferol, also known as rhamnolutein or c.i. 75640, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferol is a flavonoid lipid molecule. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol is a bitter tasting compound. It is very widespread in the plant world and is found in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae and Leguminosae. It is detected in apples, tomatoes, green tea, potatoes, onions, brussels sprouts, squash, cucumbers, lettuce, green beans, peaches, blackberries, raspberries, spinach, grapes, broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon (PMID: 21428901). Kaempferol is also one of several flavonoids that are found in cannabis plants (PMID: 6991645). Kaempferol is a biomarker for the consumption of dried and cooked beans. Many glycosides of kaempferol, such as kaempferitrin and astragalin, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. Kaempferol has numerous protective properties and has been used to treat intervertebral disc degeneration and colitis, post-menopausal bone loss, acute lung injury and has beneficial effects against cancer, liver injury, obesity and diabetes, and inhibits vascular endothelial inflammation. These treatments and protective properties of kaempferol and the potential mechanisms that kaempferol exerts these effects are part of this review ( PMID: 31572524). 3,4',5,7-Tetrahydroxyflavone 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-5,7,4'-trihydroxyflavonol 5,7,4'-Trihydroxyflavonol C.I. 75640 Campherol Indigo yellow Kaempherol Kampherol Kempferol Nimbecetin Pelargidenolon Populnetin Rhamnolutein Rhamnolutin Robigenin Swartziol Trifolitin 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 3,4',5,7-Tetrahydroxy-flavone (7ci,8ci) 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one Kampferol 3,4’,5,7-Tetrahydroxyflavone 3,5,7,4'-Tetrahydroxyflavone 3,5,7,4’-Tetrahydroxyflavone 3'-Deoxyquercetin 3’-Deoxyquercetin 5,7,4’-Trihydroxyflavonol Kaemferol Kaempferol Kampcetin Pelargidenon C15H10O6 286.24 286.0477 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one kaempferol 520-18-3 OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H IYRMWMYZSQPJKC-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Flavonols Organic compounds Phenylpropanoids and polyketides Flavonoids Flavones Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives Chromones Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Oxacyclic compounds Polyols Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3-hydroxyflavone 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Heteroaromatic compound Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Polyol Pyran Pyranone Vinylogous acid 7-hydroxyflavonol Flavones and Flavonols Flavones and Flavonols flavonols flavonols tetrahydroxyflavone melting_point 285 - 287 °C logp 1.99 ALOGPS logs -3.21 ALOGPS logp 2.46 ChemAxon pka_strongest_acidic 6.38 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one ChemAxon average_mass 286.24 ChemAxon mono_mass 286.0477 ChemAxon smiles OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 ChemAxon formula C15H10O6 ChemAxon inchi InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H ChemAxon inchikey IYRMWMYZSQPJKC-UHFFFAOYSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 74.88 ChemAxon polarizability 27.59 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4444395 DB01852 FDB000633 5280863 C05903 KMP 28499 290 C00004565 CPD1F-90 kaempferol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Calderon-Montano JM, Burgos-Moron E, Perez-Guerrero C, Lopez-Lazaro M: A review on the dietary flavonoid kaempferol. Mini Rev Med Chem. 2011 Apr;11(4):298-344. doi: 10.2174/138955711795305335. 21428901 Ren J, Lu Y, Qian Y, Chen B, Wu T, Ji G: Recent progress regarding kaempferol for the treatment of various diseases. Exp Ther Med. 2019 Oct;18(4):2759-2776. doi: 10.3892/etm.2019.7886. Epub 2019 Aug 13. 31572524 1.0 2020-03-19 00:33:41 UTC 2020-07-07 15:57:47 UTC CDB000374 Gamma-linolenic acid Gamma-Linolenic acid is also known as 18:3 (N-6), gamolenic acid or gamma-linolensaeure. It is an omega-6 polyunsaturated fatty acid (PUFA) also referred to as 9,12-octadecatrienoic acid (cis-6, cis-9, cis-12- octadecatrienoic acid). It belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. gamma-Linolenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is found largely in human milk and other botanical sources. Gamma-Linolenic acid is found in varying amounts in edible hemp seeds, oats, barley and spirulina. Gamma-linolenic acid is one of the unsaturated fatty acids found in the oil of cannabis seeds (PMID: 6991645). Gamolenic acid is also found in some fungal sources and is present naturally in the form of triglycerides. Gamolenic acid may be found in over-the-counter dietary supplements. Gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted into dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as Prostaglandin E1(PGE1). Evening primrose oil, containing 7-14% gamma-linolenic acid, has been investigated for clinical use in menopausal syndrome, diabetic neuropathy, breast pain (PMID: 27083549) and eczema. It has been questioned if evening primrose oil, containing gamma-linolenic acid, helped alleviate atopic eczema (PMID: 14670851). However, its effectiveness in treating eczema was demonstrated in a study where the topical application of borage seed oil (with higher concentrations of gamma linolenic acid than evening primrose oil) reduced symptoms of atopic dermatitis in a double-blind, placebo-controlled clinical trial (PMID: 18078406).Various clinical indications of gamolenic acid have been studied, including rheumatoid arthritis, atopic eczema, acute respiratory distress syndrome, asthma, premenstrual syndrome, cardiovascular disease, ulcerative colitis, ADHD, cancer, osteoporosis, diabetic neuropathy, and insomnia ( PMID: 27083549; PMID: 27083549). (6,9,12)-Linolenic acid (6Z,9Z,12Z)-Octadecatrienoic acid (Z,Z,Z)-6,9,12-Octadecatrienoic acid 18:3 (N-6) 6,9,12-Octadecatrienoic acid 6-cis,9-cis,12-cis-Octadecatrienoic acid all-cis-6,9,12-Octadecatrienoic acid C18:3 (N-6) C18:3, N-6,9,12 all-cis cis-Delta(6,9,12)-Octadecatrienoic acid gamma-Linolensaeure Gamoleic acid Gamolenic acid GLA Octadeca-6,9,12-triensaeure (6,9,12)-Linolenate (6Z,9Z,12Z)-Octadecatrienoate (Z,Z,Z)-6,9,12-Octadecatrienoate 6,9,12-Octadecatrienoate 6-cis,9-cis,12-cis-Octadecatrienoate all-cis-6,9,12-Octadecatrienoate cis-delta(6,9,12)-Octadecatrienoate cis-Δ(6,9,12)-octadecatrienoate cis-Δ(6,9,12)-octadecatrienoic acid g-Linolensaeure Γ-linolensaeure Gamoleate Gamolenate g-Linolenate g-Linolenic acid gamma-Linolenate Γ-linolenate Γ-linolenic acid 6(Z),9(Z),12(Z)-Octadecatrienoate 6(Z),9(Z),12(Z)-Octadecatrienoic acid 6,9,12-all-cis-Octadecatrienoate 6,9,12-all-cis-Octadecatrienoic acid 6Z,9Z,12Z-Octadecatrienoate 6Z,9Z,12Z-Octadecatrienoic acid gamma-Llnolenic acid Ligla Acid, gamma-linolenic Acid, gamolenic gamma Linolenic acid FA(18:3(6Z,9Z,12Z)) FA(18:3n6) Linolenate gamma-Linolenic acid (6Z,9Z,12Z)-6,9,12-Octadecatrienoic acid (Z,Z,Z)-6,9,12-Octatrienoic acid cis,cis,cis-6,9,12-Octadecatrienoic acid cis-6,cis-9,cis-12-Octadecatrienoic acid C18H30O2 278.43 278.2246 (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid gamma linolenic acid 506-26-3 CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- VZCCETWTMQHEPK-QNEBEIHSSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Polyunsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids linolenic acid omega-6 fatty acid logp 6.59 ALOGPS logs -6.04 ALOGPS logp 6.06 ChemAxon pka_strongest_acidic 4.92 ChemAxon iupac (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid ChemAxon average_mass 278.43 ChemAxon mono_mass 278.2246 ChemAxon smiles CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O ChemAxon formula C18H30O2 ChemAxon inchi InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12- ChemAxon inchikey VZCCETWTMQHEPK-QNEBEIHSSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 89.64 ChemAxon polarizability 33.8 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C06426 DB13854 4444436 FDB002943 5280933 28661 CPD-8117 C00001226 48234 Gamma-Linolenic_acid 386 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Sergeant S, Rahbar E, Chilton FH: Gamma-linolenic acid, Dihommo-gamma linolenic, Eicosanoids and Inflammatory Processes. Eur J Pharmacol. 2016 Aug 15;785:77-86. doi: 10.1016/j.ejphar.2016.04.020. Epub 2016 Apr 12. 27083549 Williams HC: Evening primrose oil for atopic dermatitis. BMJ. 2003 Dec 13;327(7428):1358-9. doi: 10.1136/bmj.327.7428.1358. 14670851 Kanehara S, Ohtani T, Uede K, Furukawa F: Clinical effects of undershirts coated with borage oil on children with atopic dermatitis: a double-blind, placebo-controlled clinical trial. J Dermatol. 2007 Dec;34(12):811-5. doi: 10.1111/j.1346-8138.2007.00391.x. 18078406 1.0 2020-03-19 00:33:44 UTC 2020-08-04 22:28:18 UTC CDB000375 Stearidonic acid Stearidonic acid, also known as SDA or stearidonate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Stearidonic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is biosynthesized from linolenic acid by the enzyme delta-6-desaturase. Natural sources of this fatty acid are the seed oils of hemp, blackcurrant and echium, and the cyanobacterium spirulina (a rich source of vitamins and minerals). Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) polyunsaturated fatty acids (PUFA). These oils appear to possess hypotriglyceridemic properties typically associated with fish oils (PMID: 15173404). Stearidonic acid may be used as a precursor to increase the eicosapentaenoic acid (EPA) content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition to influence cellular responses and functions in desirable ways (PMID: 15120716). (6Z,9Z,12Z,15Z)-Octadecatetraenoic acid 6,9,12,15-Octadecatetraenoic acid SDA 6Z,9Z,12Z,15Z-Octadecatetraenoic acid (6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid (6Z,9Z,12Z,15Z)-Octadecatetraenoate 6,9,12,15-Octadecatetraenoate 6Z,9Z,12Z,15Z-Octadecatetraenoate (6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoate Stearidonate Stearidonic acid C18:4 FA(18:4(6Z,9Z,12Z,15Z)) FA(18:4n3) Moroctic acid C18H28O2 276.41 276.2089 (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid stearidonic acid 20290-75-9 CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12- JIWBIWFOSCKQMA-LTKCOYKYSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Polyunsaturated fatty acids Unsaturated fatty acids long-chain fatty acid octadecatetraenoic acid omega-3 fatty acid logp 6.19 ALOGPS logs -5.74 ALOGPS logp 5.7 ChemAxon pka_strongest_acidic 4.92 ChemAxon iupac (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid ChemAxon average_mass 276.41 ChemAxon mono_mass 276.2089 ChemAxon smiles CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O ChemAxon formula C18H28O2 ChemAxon inchi InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12- ChemAxon inchikey JIWBIWFOSCKQMA-LTKCOYKYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 90.75 ChemAxon polarizability 33.11 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004293 4471933 5312508 C16300 32389 C00000405 CPD-12653 2218006 Stearidonic_acid Surette ME, Edens M, Chilton FH, Tramposch KM: Dietary echium oil increases plasma and neutrophil long-chain (n-3) fatty acids and lowers serum triacylglycerols in hypertriglyceridemic humans. J Nutr. 2004 Jun;134(6):1406-11. doi: 10.1093/jn/134.6.1406. 15173404 Miles EA, Banerjee T, Calder PC: The influence of different combinations of gamma-linolenic, stearidonic and eicosapentaenoic acids on the fatty acid composition of blood lipids and mononuclear cells in human volunteers. Prostaglandins Leukot Essent Fatty Acids. 2004 Jun;70(6):529-38. doi: 10.1016/j.plefa.2003.11.008. 15120716 1.0 2020-03-19 00:33:47 UTC 2020-07-24 23:30:19 UTC CDB000376 Eicosanoic acid Arachidic acid, also known as eicosanoic acid or eicosanoate, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, arachidic acid is considered to be a fatty acid lipid molecule. Eicosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Eicosanoic acid can be found in a number of food items such as chinese cinnamon, strawberry, winged bean, and thistle. Eicosanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Eicosanoic acid is one of several unsaturated fatty acids that have been identified in cannabis plants (PMID: 28448475). Arachidic acid is used for the production of detergents, photographic materials and lubricants (1S,2R,5S,10R,11S,14R,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl icosanoic acid C47H84O2 681.19 680.6471 (1S,2R,5S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl icosanoate (1S,2R,5S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl icosanoate 506-30-9 CCCCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@H]3CC=C2C1)[C@H](C)CCCC(C)C InChI=1S/C47H84O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h28,37-38,40-44H,7-27,29-36H2,1-6H3/t38-,40+,41-,42-,43+,44+,46+,47-/m1/s1 SUOVMGLZSOAHJY-LJQWFZDRSA-N melting_point 75.4 °C Wikipedia boiling_point 328 °C Wikipedia logp 10.96 ALOGPS logs -7.96 ALOGPS logp 15.81 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1S,2R,5S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl icosanoate ChemAxon average_mass 681.19 ChemAxon mono_mass 680.6471 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@H]3CC=C2C1)[C@H](C)CCCC(C)C ChemAxon formula C47H84O2 ChemAxon inchi InChI=1S/C47H84O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h28,37-38,40-44H,7-27,29-36H2,1-6H3/t38-,40+,41-,42-,43+,44+,46+,47-/m1/s1 ChemAxon inchikey SUOVMGLZSOAHJY-LJQWFZDRSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 212.61 ChemAxon polarizability 93.78 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Mikulcova V, Kasparkova V, Humpolicek P, Bunkova L: Formulation, Characterization and Properties of Hemp Seed Oil and Its Emulsions. Molecules. 2017 Apr 27;22(5). pii: molecules22050700. doi: 10.3390/molecules22050700. 28448475 1.0 2020-03-19 00:33:50 UTC 2020-07-07 15:57:49 UTC CDB000377 Cis-Vaccenic acid Cis-Vaccenic acid, (11Z)-11-octadecenoic acid, 18:1 cis-11, also known as vaccenate or asclepic acid, is an isomer of vaccenic acid. It belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Cis-Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-Vaccenic acid, an omega-7 fatty acid, is a naturally occurring trans fatty acid found in Sea Buckthorn (Hippophae rhamnoides) oil. Vaccenic acid was first discovered in 1928 in animal fats and butter. Mammals convert it into rumenic acid, a conjugated linoleic acid. In a study of chemically induced mammary carcinogenesis in rats, vaccenic acid, when converted to cis-9, trans-11 conjugated linoleic acid (CLA) by delta 9-desaturase, had anticarcinogenic properties (PMID: 15465769). Cis-Vaccenic acid is one of several unsaturated fatty acid that are found in the essential oil of cannabis seed (PMID: 6991645). (Z)-11-Octadecenoic acid (Z)-Octadec-11-enoic acid Asclepic acid cis-11-Octadecenoic acid cis-Octadec-11-enoic acid VACCENIC ACID (Z)-11-Octadecenoate (Z)-Octadec-11-enoate Asclepate cis-11-Octadecenoate cis-Octadec-11-enoate VACCENate cis-Vaccenate (11Z)-Octadecenoate (11Z)-Octadecenoic acid 11-Octadecenoate 11-Octadecenoic acid 11Z-Octadecenoate 11Z-Octadecenoic acid C18H34O2 282.46 282.2559 (11Z)-octadec-11-enoic acid cis-vaccenic acid 506-17-2 CCCCCC\C=C/CCCCCCCCCC(O)=O InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7- UWHZIFQPPBDJPM-FPLPWBNLSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Unsaturated fatty acids vaccenic acid logp 7.67 ALOGPS logs -6.36 ALOGPS logp 6.78 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac (11Z)-octadec-11-enoic acid ChemAxon average_mass 282.46 ChemAxon mono_mass 282.2559 ChemAxon smiles CCCCCC\C=C/CCCCCCCCCC(O)=O ChemAxon formula C18H34O2 ChemAxon inchi InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7- ChemAxon inchikey UWHZIFQPPBDJPM-FPLPWBNLSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 87.4 ChemAxon polarizability 37.1 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04801 5282761 50464 FDB002952 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C: The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats. J Nutr. 2004 Oct;134(10):2698-704. doi: 10.1093/jn/134.10.2698. 15465769 1.0 2020-03-19 00:33:53 UTC 2020-08-04 22:28:18 UTC CDB000378 Isolinolenic acid 9E,11E-Octadecadienoic acid, also known as (e,e)-isolinoleic acid or (9E,11E)-9,11-octadecadienoate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Conjugated linoleic acid (CLA) is an integral term for the mixture of positional and geometrical isomers of the octadecadienoic acids, whose two double-bonds are separated with one single-bond. The most common isomers are cis-9, trans-11, and trans-10, cis-12. 9E,11E-Octadecadienoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 9E,11E-Octadecadienoic acid has been detected in milk and dairy products (from cow) and red meat. This could make 9E,11E-octadecadienoic acid a potential biomarker for the consumption of these foods. Isolinolenic acid is one of many unsaturated fatty acids that have been identified in the oil of cannabis seeds (PMID: 6991645). Much attention has focused on the therapeutic potential of conjugated linoleic acid. Initial animal studies associated conjugated linoleic acid with beneficial health properties, such as reducing the risk of cancer, diabetes, atherosclerosis, inflammation, and obesity. More recent human CLA-supplementation studies have often shown conflicting and less convincing health benefits. The marked variation between studies may reflect the isomer-specific effect of the individual conjugated linoleic acid isomers, which can often have opposing effects. Detrimental effects have been observed in some studies, after supplementation with the trans-10, cis-12 conjugated linoleic acid isomer. Diet composition may modulate CLA effects on body fat accumulation. Contemporary dietary recommendations tend to limit red meat and dairy products and the possible CLA deficiencies must be compensated with dietary supplements. However, with human studies, a specific dietary pattern that controls and includes CLA has not been established. As a result, differences among studies and among subjects in the same study are likely. In rodents, the effects of CLA vary with genotype, suggesting that genetic predisposition to fat accumulation can play an important role in the effectiveness of CLA. Human volunteers with different body mass index have participated in the published studies and even in the same experiment. So, differences in lipid metabolism among subjects could help to explain the discrepancies observed in the literature. Age and maturity of the participants may also impact these studies (PMID: 17053429, 17217167, 17554969, 16477173). 9,11-Linoleic acid CLA 80 Conjugated linoleic acid delta9,11-Octadecadienoate Nouracid de 554 Ricineic acid Ricinenic acid Selin cla 9,11-Linoleic acid, (E,E)-isomer 9,11-Isolinoleic acid Octadeca-9,11-dienoic acid 9,11-Octadecadienoate (9E,11E)-9,11-Octadecadienoic acid (9E,11E)-Octadecadienoic acid 9,11-Conjugated linoleic acid 9-trans,11-trans-Linoleic acid 9-trans,11-trans-Octadecadienoic acid 9E,11E-Octadecadienoic acid FA(18:2(9E,11E)) delta9,11-Octadecadienoic acid trans-11-trans-9-Octadecadienoic acid trans-9,trans-11 Conjugated linoleic acid trans-9,trans-11-Octadecadienoic acid Δ9,11-Octadecadienoic acid 9E,11E-Octadecadienoate 10E,12Z-Octadecadienoate (E,E)-9,11-Octadecadienoic acid (E,E)-Isolinoleic acid 9-trans, 11-trans-CLA 9-trans,11-trans-Conjugated linoleic acid 9E,11E-CLA 9t,11t-CLA Conjugated (9E,11E)-linoleic acid Isolinoleic acid Mangold's acid trans,trans-9,11-Octadecadienoic acid trans-9, trans-11-Octadecadienoic acid (9E,11E)-9,11-Octadecadienoate (E,E)-9,11-Octadecadienoate (E,E)-Isolinoleate 9-trans,11-trans-Conjugated linoleate 9-trans,11-trans-Octadecadienoate Conjugated (9E,11E)-linoleate Isolinoleate trans,trans-9,11-Octadecadienoate trans-9, trans-11-Octadecadienoate C18H32O2 280.45 280.2402 (9E,11E)-octadeca-9,11-dienoic acid 9E,11E-octadecadienoic acid 1839-11-8 CCCCCC\C=C\C=C\CCCCCCCC(O)=O InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+ JBYXPOFIGCOSSB-XBLVEGMJSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Unsaturated fatty acids logp 7.11 ALOGPS logs -6.28 ALOGPS logp 6.42 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9E,11E)-octadeca-9,11-dienoic acid ChemAxon average_mass 280.45 ChemAxon mono_mass 280.2402 ChemAxon smiles CCCCCC\C=C\C=C\CCCCCCCC(O)=O ChemAxon formula C18H32O2 ChemAxon inchi InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7+,10-9+ ChemAxon inchikey JBYXPOFIGCOSSB-XBLVEGMJSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 88.52 ChemAxon polarizability 37.12 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4445923 FDB023610 36025 5282796 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Toomey S, McMonagle J, Roche HM: Conjugated linoleic acid: a functional nutrient in the different pathophysiological components of the metabolic syndrome? Curr Opin Clin Nutr Metab Care. 2006 Nov;9(6):740-7. doi: 10.1097/01.mco.0000247465.34037.05. 17053429 Navarro V, Fernandez-Quintela A, Churruca I, Portillo MP: The body fat-lowering effect of conjugated linoleic acid: a comparison between animal and human studies. J Physiol Biochem. 2006 Jun;62(2):137-47. doi: 10.1007/BF03174074. 17217167 Tvrzicka E, Vecka M, Zak A: [Conjugated linoleic acid--the dietary supplement in the prevention of cardiovascular diseases]. Cas Lek Cesk. 2007;146(5):459-65. 17554969 Tricon S, Yaqoob P: Conjugated linoleic acid and human health: a critical evaluation of the evidence. Curr Opin Clin Nutr Metab Care. 2006 Mar;9(2):105-10. doi: 10.1097/01.mco.0000214567.44568.fb. 16477173 1.0 2020-03-19 00:33:55 UTC 2020-08-04 22:28:18 UTC CDB000379 Lignoceric acid Lignoceric acid or tetracosanoate, also known as lignocerat, with formula C23H47COOH, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Lignoceric acid is a fatty acid lipid molecule. Lignoceric acid is practically insoluble in water and a weakly acidic compound. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain 1.1% ‚Äì 2.2% of lignoceric acid. This fatty acid is also a by product of lignin production. Lignoceric acid is one of the saturated fatty acids identified in the oil of cannabis seed (PMID: 6991645). In humans, Lignoceric acid, one of the very long chain fatty acids, is associate with the X-chromosome linked disease, adrenoleukodystrophy (ALD), marked by a deficiency in peroxisomal fatty acid beta oxidation. ALD is caused by mutations in ABCD1, a gene that encodes for ALD, a peroxisomal membrane transporter protein. Those with ALD build-up long chain fatty acids, affecting myelin in the central nervous system, the adrenal cortex, and the Leydig cells in the testes. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. CH3-[CH2]22-COO(-) Lignocerat Lignocerate N-Tetracosanoate Tetracosanate Tetracosanoat Tetracosoate Tetraeicosanoate Lignoceric acid N-Tetracosanoic acid Tetracosanic acid Tetracosoic acid Tetraeicosanoic acid Tetracosanoic acid Tetracosanoate C24H47O2 367.63 367.3576 tetracosanoate lignocerate 46927-71-3 CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)/p-1 QZZGJDVWLFXDLK-UHFFFAOYSA-M belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Very long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Very long-chain fatty acid a saturated fatty acid a very long chain fatty acid fatty acid anion 24:0 straight-chain saturated fatty acid anion very long-chain fatty acid anion melting_point 84.2 °C Wikipedia logp 9.89 ALOGPS logs -7.48 ALOGPS logp 9.81 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac tetracosanoate ChemAxon average_mass 367.63 ChemAxon mono_mass 367.3576 ChemAxon smiles CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O ChemAxon formula C24H47O2 ChemAxon inchi InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)/p-1 ChemAxon inchikey QZZGJDVWLFXDLK-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 124.73 ChemAxon polarizability 51.07 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5461021 31014 TETRACOSANOATE Lignoceric acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:34:00 UTC 2020-07-24 23:30:07 UTC CDB000380 Caproic acid Caproic acid, also known as hexanoate or caproate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Caproic acid is a medium chain triglyceride (MCT). Caproic acid is a medium chain triglycerides (MCT). Caproic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It is a conjugate acid of a hexanoate. Caproic acid is found naturally in various plant and animal fats and oils. Caproic acid is one of the saturated fatty acids that are known in cannabis plant. (PMID: 6991645) 1-Hexanoic acid 1-Pentanecarboxylic acid 6:0 Butylacetic acid C6:0 Capronic acid CH3-[CH2]4-COOH Hexanoate Hexoic acid Hexylic acid N-Caproic acid N-Hexanoic acid N-Hexoic acid N-Hexylic acid Pentanecarboxylic acid Pentiformic acid Pentylformic acid 1-Hexanoate 1-Pentanecarboxylate Butylacetate Capronate Hexanoic acid Hexoate Hexylate N-Caproate N-Hexanoate N-Hexoate N-Hexylate Pentanecarboxylate Pentiformate Pentylformate Caproate Hexanoic acid, calcium salt Hexanoic acid, sodium salt, 1-(11)C-labeled Hexanoic acid, nickel (2+) salt Hexanoic acid, sodium salt Bismuth(III)hexanoate Hexanoic acid, copper (2+) salt Hexanoic acid, manganese (2+) salt Bi(ohex)3 Hexanoic acid, barium salt Hexanoic acid, potassium salt Hexanoic acid, rhodium (2+) salt FA(6:0) Calcium N-hexanoate Hexanoic acid, sodium salt (1:1) Sodium capronate Calcium hexanoate Caproic acid sodium salt Sodium caproate Sodium hexanoate C6H12O2 116.16 116.0837 hexanoic acid hexanoic acid 142-62-1 CCCCCC(O)=O InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) FUZZWVXGSFPDMH-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Saturated fatty acids Straight chain fatty acids Straight chain fatty acids medium-chain fatty acid straight-chain saturated fatty acid water_solubility 10.3 mg/mL logp 1.92 HANSCH,C ET AL. (1995) melting_point −3.4 °C Wikipedia boiling_point 205.8 °C Wikipedia logp 1.88 ALOGPS logs -1.08 ALOGPS logp 1.81 ChemAxon pka_strongest_acidic 5.09 ChemAxon iupac hexanoic acid ChemAxon average_mass 116.16 ChemAxon mono_mass 116.0837 ChemAxon smiles CCCCCC(O)=O ChemAxon formula C6H12O2 ChemAxon inchi InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) ChemAxon inchikey FUZZWVXGSFPDMH-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 31.07 ChemAxon polarizability 13.27 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013897 8552 30776 8892 C01585 C00001218 Hexanoic_acid 5520 HEXANOATE Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:34:04 UTC 2020-07-24 23:30:07 UTC CDB000381 Heptanoic acid Heptanoic acid or heptanoate, also known as enanthylic acid, or enanthic acid, is an organic compound composed of a seven-carbon chain terminating in a carboxylic acid. It belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Heptanoate is a very weakly acidic compound, is slightly soluble in water, but very soluble in ethanol and ether. It is an oily liquid with an unpleasant, rancid odor that contributes to the odor of some rancid oils. Present in essential oils, such as violet leaf oil, palm oil, it is also found in apple, feijoa fruit, clove bud, ginger, black tea, morello cherry, grapes, rice bran, scallops, leek and other foodstuffs such as strawberry jam, soups and sauces. Heptanoic acid is one of several saturated fatty acids isolated from the oil of cannabis seeds (PMID: 6991645). Heptanoic acid is used in the preparation of esters, such as ethyl heptanoate, which are used in fragrances and as artificial flavors. It is one of many additives in cigarettes. Heptanoic acid is used to esterify steroids in the preparation of drugs such as testosterone enanthate, trenbolone enanthate, drostanolone enanthate, and methenolone enanthate (Primobolan). It is used as one of the components in washing solutions and used to assist lye peeling (by immersion into a lye solution) of fruit and vegetables. (7:0) 1-Hexanecarboxylate CH3-[CH2]5-COO(-) Enanthate Enanthylate Heptanoic acid, ion(1-) Heptoate Heptylate N-Heptanoate N-Heptoate N-Heptylate Oenanthate Oenanthylate 1-Hexanecarboxylic acid Enanthic acid Enanthylic acid Heptanoate, ion(1-) Heptoic acid Heptylic acid N-Heptanoic acid N-Heptoic acid N-Heptylic acid Oenanthic acid Oenanthylic acid Heptanoic acid C7H13O2 129.18 129.0921 heptanoate enanthate 7563-37-3 CCCCCCC([O-])=O InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)/p-1 MNWFXJYAOYHMED-UHFFFAOYSA-M belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid a medium chain fatty acid a saturated fatty acid medium-chain fatty acid anion straight-chain saturated fatty acid anion water_solubility 0.2419 g/100 mL at 15 °C Wikipedia melting_point −7.5 °C Wikipedia boiling_point 223 °C Wikipedia logp 2.45 ALOGPS logs -1.65 ALOGPS logp 2.26 ChemAxon pka_strongest_acidic 5.15 ChemAxon iupac heptanoate ChemAxon average_mass 129.18 ChemAxon mono_mass 129.0921 ChemAxon smiles CCCCCCC([O-])=O ChemAxon formula C7H13O2 ChemAxon inchi InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)/p-1 ChemAxon inchikey MNWFXJYAOYHMED-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 46.51 ChemAxon polarizability 14.89 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB030902 32362 93052 CPD-7619 Heptanoic acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:34:06 UTC 2020-07-24 23:30:07 UTC CDB000382 Caprylic acid Caprylic acid, or octanoic acid, with the structural formula CH3(CH2)6CO2H, is an eight-carbon straight-chain fatty acid and a carboxylic acid. It is an oily liquid with a slightly unpleasant rancid taste and odor. It is minimally soluble in water. Caprylic acid can be found in numerous foods such as Prunus (Cherry, Plum), pineapple sages, black raspberries, shallots, coconuts and breast milk. Caprylic acid is straight-chain fatty acids found in cannabis (PMID: 6991645). Caprylic acid is taken as a dietary supplement. Caprylic acid is used commercially in the production of esters used in perfumery and in the manufacture of dyes. Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, industrial facilities, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in greenhouses and garden centers. Caprylic acid, and other fatty acids, affect the hunger hormone ghrelin. Ghrelin must be acylated, where it acquires an -OH group, before it can stimulate the hunger receptors in the hypothalamus. Caprylic acid becomes linked post-translationally to serine at the 3-position by the enzyme ghrelin O-acyltransferase (GOAT), located on the cell membrane of ghrelin cells in the stomach and pancreas (PMID 19896496). Caprylic acid affects those with medium-chain acyl-CoA dehydrogenase deficiency (MCAD), which is an inborn error of metabolism, marked by mutations of the gene ACADM. Those affected with MCAD have difficulties converting fatty acids to energy, especially during fasting. As a result, fatty acids build up and cause damage to liver and brain (PMID: 27536022). 1-Heptanecarboxylate Caprilate Caprylate CH3-[CH2]6-COO(-) N-Caprylate N-Octanoate N-Octoate N-Octylate Octanoic acid, ion(1-) Octylate 1-Heptanecarboxylic acid Caprilic acid Caprylic acid N-Caprylic acid N-Octanoic acid N-Octoic acid N-Octylic acid Octanoate, ion(1-) Octylic acid Octanoic acid C8H15O2 143.2 143.1072 octanoate octanoate 74-81-7 CCCCCCCC([O-])=O InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1 WWZKQHOCKIZLMA-UHFFFAOYSA-M belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid a medium chain fatty acid a saturated fatty acid fatty acid anion 8:0 straight-chain saturated fatty acid anion water_solubility 0.068 g/100 mL Wikipedia logp 3.05 Wikipedia melting_point 16.7 °C Wikipedia boiling_point 239.7 °C Wikipedia logp 3.01 ALOGPS logs -2.28 ALOGPS logp 2.7 ChemAxon pka_strongest_acidic 5.19 ChemAxon iupac octanoate ChemAxon average_mass 143.2 ChemAxon mono_mass 143.1072 ChemAxon smiles CCCCCCCC([O-])=O ChemAxon formula C8H15O2 ChemAxon inchi InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)/p-1 ChemAxon inchikey WWZKQHOCKIZLMA-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 51.11 ChemAxon polarizability 16.95 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB031069 106634 119389 25646 Caprylic acid Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Castaneda TR, Tong J, Datta R, Culler M, Tschop MH: Ghrelin in the regulation of body weight and metabolism. Front Neuroendocrinol. 2010 Jan;31(1):44-60. doi: 10.1016/j.yfrne.2009.10.008. Epub 2009 Nov 5. 19896496 Vishwanath VA: Fatty Acid Beta-Oxidation Disorders: A Brief Review. Ann Neurosci. 2016 Mar;23(1):51-5. doi: 10.1159/000443556. Epub 2016 Mar 11. 27536022 1.0 2020-03-19 00:34:10 UTC 2020-08-04 22:28:18 UTC CDB000383 Pelargonic acid Pelargonic acid, also known as nonanoic acid or pelargon, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Pelargonic acid is an oily liquid with an unpleasant, rancid odor. It is a very hydrophobic molecule, practically insoluble in water but very soluble in organic solvents. The biosynthesis of fatty acid occurs through the acetate pathway and the process is catalyzed by the Fatty Acid Synthase (FAS) enzymes. Structurally, FAS varies significantly across different organisms but essentially, they all perform the same task using the same mechanisms. Pelargonic acid is one of the saturated fatty acids that have been identified in cannabis plant (PMID: 661645).¬† Nonanoic acid is also used in the preparation of plasticizers and lacquers. Synthetic esters of nonanoic acid, such as methyl nonanoate, are used as flavorings. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays. The ammonium salt of nonanoic acid, ammonium nonanoate, is an herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, to control weeds in turfgrass (https://en.wikipedia.org/wiki/Nonanoic_acid). Nonanoic acid may be used to treat seizures (PMID 23177536). 1-Nonanoic acid 1-Octanecarboxylic acid CH3-[CH2]7-COOH N-Nonanoic acid Nonanoate Nonansaeure Nonoic acid Nonylic acid Pelargic acid Pelargon Pelargonsaeure Pergonic acid 1-Nonanoate 1-Octanecarboxylate N-Nonanoate Nonanoic acid Nonoate Nonylate Pelargate Pergonate Pelargonate Cirrasol 185a Emery 1202 Emery'S L-114 Emfac 1202 Hexacid C-9 N-Nonoate N-Nonoic acid N-Nonylate N-Nonylic acid N-Pelargonate N-Pelargonic acid Pelargonic acid, calcium salt Potassium nonanoate Pelargonic acid, cadmium salt Pelargonic acid, sodium salt Pelargonic acid, zinc salt Pelargonic acid, aluminum salt Pelargonic acid, potassium salt FA(9:0) Pelargonic acid C9H18O2 158.24 158.1307 nonanoic acid nonanoic acid 112-05-0 CCCCCCCCC(O)=O InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) FBUKVWPVBMHYJY-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Straight chain fatty acids Straight chain fatty acids medium-chain fatty acid straight-chain saturated fatty acid water_solubility 0.284 mg/mL logp 3.42 SANGSTER (1993) melting_point 12.3 °C boiling_point 254 °C Wikipedia logp 3.47 ALOGPS logs -2.75 ALOGPS logp 3.14 ChemAxon pka_strongest_acidic 5.23 ChemAxon iupac nonanoic acid ChemAxon average_mass 158.24 ChemAxon mono_mass 158.1307 ChemAxon smiles CCCCCCCCC(O)=O ChemAxon formula C9H18O2 ChemAxon inchi InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) ChemAxon inchikey FBUKVWPVBMHYJY-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 44.88 ChemAxon polarizability 19.49 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003306 7866 C01601 8158 29019 CPD-8505 C00030829 Nonanoic_acid 5810 Miller IuM, Marchenko IV, Kapustin OA, Galanina LA, Bekhtereva MN: [Use of a mass spectrometric method for studying the oxygen demand of suspensions of resting Bacillus anthracoides spores]. Mikrobiologiia. 1978 Mar-Apr;47(2):357-61. 661645 Chang P, Terbach N, Plant N, Chen PE, Walker MC, Williams RS: Seizure control by ketogenic diet-associated medium chain fatty acids. Neuropharmacology. 2013 Jun;69:105-14. doi: 10.1016/j.neuropharm.2012.11.004. Epub 2012 Nov 20. 23177536 1.0 2020-03-19 00:34:13 UTC 2020-08-04 22:28:18 UTC CDB000384 Capric acid Capric acid, with the molecular formula CH3(CH2)8COOH, also known as Decanoic acid (C10:0) or decylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Capric Acid is a saturated medium-chain fatty acid with a 10-carbon backbone. Capric acid has a sweaty, unpleasant odor. Capric Acid is one of several saturated fatty acids that are known in cannabis plants (PMID:6991645). Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%). It is found in the milk of various mammals and to a lesser extent in other animal fats (https://doi.org/10.1351/pac200173040685). It also comprises 1.62% of the fats from the fruit of the durian species Durio graveolens. Capric acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals. Capric acid acts as a non-competitive Œ±-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPA) receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner and it exhibits anti-seizure effects (PMID: 26608744). 1-Nonanecarboxylate Caprate Caprinate Caprynate CH3-[CH2]8-COO(-) Decanoic acid anion Decoate Decylate N-Caprate N-Decanoate N-Decoate N-Decylate NC9H19CO2 Anion 1-Nonanecarboxylic acid Capric acid Caprinic acid Caprynic acid Decanoate anion Decoic acid Decylic acid N-Capric acid N-Decanoic acid N-Decoic acid N-Decylic acid Decanoic acid (N-C10:0) Decanoic acid C10H19O2 171.26 171.1385 decanoate decanoate 334-48-5 CCCCCCCCCC([O-])=O InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)/p-1 GHVNFZFCNZKVNT-UHFFFAOYSA-M belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid a medium chain fatty acid a saturated fatty acid fatty acid anion 10:0 medium-chain fatty acid anion straight-chain saturated fatty acid anion water_solubility 0.015 g/100 mL at 20 °C Wikipedia logp 4.09 Wikipedia melting_point 31.6 °C Wikipedia boiling_point 268.7 °C Wikipedia logp 4.13 ALOGPS logs -3.53 ALOGPS logp 3.59 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac decanoate ChemAxon average_mass 171.26 ChemAxon mono_mass 171.1385 ChemAxon smiles CCCCCCCCCC([O-])=O ChemAxon formula C10H19O2 ChemAxon inchi InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)/p-1 ChemAxon inchikey GHVNFZFCNZKVNT-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 60.31 ChemAxon polarizability 21.14 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 27689 4678093 CPD-3617 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Chang P, Augustin K, Boddum K, Williams S, Sun M, Terschak JA, Hardege JD, Chen PE, Walker MC, Williams RS: Seizure control by decanoic acid through direct AMPA receptor inhibition. Brain. 2016 Feb;139(Pt 2):431-43. doi: 10.1093/brain/awv325. Epub 2015 Nov 25. 26608744 1.0 2020-03-19 00:34:15 UTC 2020-07-24 23:30:19 UTC CDB000385 Lauric acid Lauric acid also known as dodecylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.Lauric acid. is a weakly acidic compound (based on its pKa). Based on a study (https://doi.org/10.1007/978-1-59259-947-9_2) Lauric acid is one of the saturated fatty acids found in the oil of cannabis seeds. 1-Undecanecarboxylate C12 Fatty acid anion CH3-[CH2]10-COO(-) Dodecoate Dodecylate Duodecyclate Duodecylate Laurate Laurostearate N-Dodecanoate Undecane-1-carboxylate Vulvate 1-Undecanecarboxylic acid Dodecoic acid Dodecylic acid Duodecyclic acid Duodecylic acid Lauric acid Laurostearic acid N-Dodecanoic acid Undecane-1-carboxylic acid Vulvic acid Dodecanoic acid (N-C12:0) Dodecanoate Dodecanoic acid Laate Laic acid C12H23O2 199.31 199.1698 dodecanoate laurate 143-07-7 CCCCCCCCCCCC([O-])=O InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)/p-1 POULHZVOKOAJMA-UHFFFAOYSA-M belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid a medium chain fatty acid a saturated fatty acid fatty acid anion 12:0 medium-chain fatty acid anion straight-chain saturated fatty acid anion water_solubility 55 mg/L at 20 °C Wikipedia logp 4.6 Wikipedia melting_point 43.8 °C Wikipedia boiling_point 297.9 °C at 512 mmHg Wikipedia logp 5.24 ALOGPS logs -4.72 ALOGPS logp 4.48 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac dodecanoate ChemAxon average_mass 199.31 ChemAxon mono_mass 199.1698 ChemAxon smiles CCCCCCCCCCCC([O-])=O ChemAxon formula C12H23O2 ChemAxon inchi InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)/p-1 ChemAxon inchikey POULHZVOKOAJMA-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 69.52 ChemAxon polarizability 25.37 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4149208 18262 DODECANOATE 1.0 2020-03-19 00:34:19 UTC 2020-07-07 15:57:55 UTC CDB000386 Margaric acid Heptadecanoic acid, also known as margaric acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Heptadecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" lengths long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid is usually found in trace amounts and constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products (PMID: 9701185). It is a common constituent of lipids, such as those present in Physalia physalis (Portuguese-man-of-war). Heptadecanoic acid is a constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). Heptadecanoic acid has pheromonic and allomonic properties for insects and reptiles. The subcaudal gland secretions of the European badger (Meles meles) and the occipital gland secretions of male bactrian camels (Camelus bactrianus) contain many pheromonic chemicals, including heptadecanoic acid, that aid in finding and selection of mates (PMID: 24414593). Heptadecanoic acid is an attractant of the khapra beetle (Trogoderma granarium) and the yellow fever mosquito (Aedes aegypti) but as a repellent of the common house mosquito (Culex pipiens; doi: 10.5962/bhl.title.49749). Heptadecanoic acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius; PMID 24264893) and the European viper (Vipera berus), where it is used for the identification of sexual partners (doi:10.1007/bf00579807). 17:0 C17:0 CH3-[CH2]15-COOH Heptadecoic acid Heptadecylic acid Margaric acid Margarinic acid Margarinsaeure N-Heptadecanoic acid N-Heptadecoic acid N-Heptadecylic acid Heptadecoate Heptadecylate Margarate Margarinate N-Heptadecanoate N-Heptadecoate N-Heptadecylate Heptadecanoate Margaroate Margaroic acid Normal-heptadecanoate Normal-heptadecanoic acid Margaric acid, 1-(11)C-labeled Margaric acid, nickel (2+) salt Omega I-123 heptadecanoic acid Margaric acid, potassium salt Margaric acid, sodium salt FA(17:0) Heptadecanoic acid C17H34O2 270.45 270.2559 heptadecanoic acid heptadecanoic acid 506-12-7 CCCCCCCCCCCCCCCCC(O)=O InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19) KEMQGTRYUADPNZ-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Straight chain fatty acids long-chain fatty acid straight-chain saturated fatty acid melting_point 61.3 °C boiling_point 227 °C at 100 mmHg Wikipedia logp 7.66 ALOGPS logs -6.25 ALOGPS logp 6.7 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac heptadecanoic acid ChemAxon average_mass 270.45 ChemAxon mono_mass 270.2559 ChemAxon smiles CCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C17H34O2 ChemAxon inchi InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19) ChemAxon inchikey KEMQGTRYUADPNZ-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 81.68 ChemAxon polarizability 36.49 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004676 10033 10465 32365 C00007426 215873 Heptadecanoic_acid 6578 CPD-7830 Wolk A, Vessby B, Ljung H, Barrefors P: Evaluation of a biological marker of dairy fat intake. Am J Clin Nutr. 1998 Aug;68(2):291-5. doi: 10.1093/ajcn/68.2.291. 9701185 Ayorinde F, Wheeler JW, Wemmer C, Murtaugh J: Volatile components of the occipital gland secretion of the bactrian camel (Camelus bactrianus). J Chem Ecol. 1982 Jan;8(1):177-83. doi: 10.1007/BF00984014. 24414593 Mason RT, Gutzke WH: Sex recognition in the leopard gecko,Eublepharis macularius (Sauria: Gekkonidae) Possible mediation by skin-derived semiochemicals. J Chem Ecol. 1990 Jan;16(1):27-36. doi: 10.1007/BF01021265. 24264893 1.0 2020-03-19 00:34:21 UTC 2020-07-31 20:34:14 UTC CDB000387 Isoarachidic acid Isoarachidic acid or 18-methylnonadecanoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Isoarachidic acid is a methyl-branched fatty acid that is nonadecanoic acid substituted by a methyl group at position 18. It is a methylated derivative of nonadecanoic acid. Isoarachidic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonadecanoic acid can be found in fats and vegetable oils, although it is rare. It is the major constituent of the substance secreted by soldiers of the termite Rhinotermes marginalis for defence purposes ( doi:10.1016/0305-0491(82)90489-8). Isoarachidic acid is one of the major saturated fatty acids found in the oil of cannabis seeds (https://doi.org/10.1007/978-1-59259-947-9_2). 18-Methylnonadecylic acid Isoarachidic acid 18-Methylnonadecylate Isoarachidate 18-Methylnonadecanoate C20H40O2 312.54 312.3028 18-methylnonadecanoic acid isoarachidic acid 6250-72-2 CC(C)CCCCCCCCCCCCCCCCC(O)=O InChI=1S/C20H40O2/c1-19(2)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(21)22/h19H,3-18H2,1-2H3,(H,21,22) UCDAVJCKGYOYNI-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Branched fatty acids branched-chain saturated fatty acid long-chain fatty acid methyl-branched fatty acid logp 8.52 ALOGPS logs -6.82 ALOGPS logp 7.88 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac 18-methylnonadecanoic acid ChemAxon average_mass 312.54 ChemAxon mono_mass 312.3028 ChemAxon smiles CC(C)CCCCCCCCCCCCCCCCC(O)=O ChemAxon formula C20H40O2 ChemAxon inchi InChI=1S/C20H40O2/c1-19(2)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(21)22/h19H,3-18H2,1-2H3,(H,21,22) ChemAxon inchikey UCDAVJCKGYOYNI-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 95.44 ChemAxon polarizability 42.68 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4383090 84899 1.0 2020-03-19 00:34:25 UTC 2020-08-04 22:28:18 UTC CDB000388 2-Methyl-2-hepten-6-one 6-Methyl-5-hetpen-2-one or sulcatone, also known as methylheptenone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Sulcatone is a very hydrophobic methylketone, practically insoluble in water, and relatively neutral. It exists as a clear, colorless liquid. Sulcatone can be found in all eukaryotes, ranging from yeast to plants to humans. Sulcatone has a musty, apple green-bean, and pear-like taste. and a citrus-like lemongrass odor. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil. Sulcatone is naturally found in bay leaf, blackberry fruit, sour cherries, cloves, ginger and lavender. In insects and animals, it has a role as an alarm or attractant pheromone. In fact, sulcatone is one of a number of mosquito attractants, especially for those species such as Aedes aegypti with the odor receptor gene Or4 (PMID: 25391959). Sulcatone is secreted by humans in their sweat and is a compound frequently found in human body odors (but in few other mammals). Sulcoatone is used as a pheromone by ferrets, european badgers, red foxes, treefrogs, bedbugs, wasps and butterflies. Sulcatone is one of several ketones found in Cannabis sativa (PMID: 6991645). 6-Methyl-5-hepten-2-one 6-Methylhept-5-en-2-one Methylheptenone 2-Methyl-2-hepten-6-one 2-Methyl-6-heptenone 2-Methyl-6-oxo-2-heptene 2-Methylhept-2-en-6-one 2-oxo-6-Methylhept-5-ene 6-Methyl hept-5-en-2-one 6-Methyl-5-heptene-2-one 6-Methylheptan-5-ene-2-one FEMA 2707 Prenylacetone 6-Methylhept-5-ene-2-one Sulcatone C8H14O 126.2 126.1045 6-methylhept-5-en-2-one 6-methyl-5-hepten-2-one 110-93-0 CC(C)=CCCC(C)=O InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3 UHEPJGULSIKKTP-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons a ketone an apocarotenoid heptenone methyl ketone melting_point -67 °C logp 2.01 ALOGPS logs -1.55 ALOGPS logp 2.02 ChemAxon pka_strongest_acidic 19.6 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac 6-methylhept-5-en-2-one ChemAxon average_mass 126.2 ChemAxon mono_mass 126.1045 ChemAxon smiles CC(C)=CCCC(C)=O ChemAxon formula C8H14O ChemAxon inchi InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3 ChemAxon inchikey UHEPJGULSIKKTP-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 40.02 ChemAxon polarizability 15.53 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004925 9478 9862 C07287 16310 CPD-7969 C00011400 Sulcatone Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McBride CS, Baier F, Omondi AB, Spitzer SA, Lutomiah J, Sang R, Ignell R, Vosshall LB: Evolution of mosquito preference for humans linked to an odorant receptor. Nature. 2014 Nov 13;515(7526):222-7. doi: 10.1038/nature13964. 25391959 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:34:29 UTC 2020-07-24 23:30:07 UTC CDB000389 Azealic acid Azelaic acid, also known as 1,9-nonanedioate, AZA or azelex, is a saturated nine-carbon dicarboxylic acid. It ocurrs in all living organisms, ranging from bacteria to humans. AZA possesses a variety of in vitro and in vivo biological activities. In aerobic bacteria, azelaic acid reversibly inhibits several oxidoreductive enzymes including tyrosinase, mitochondrial enzymes of the respiratory chain, thioredoxin reductase, 5-alpha-reductase, and DNA polymerases. It is currently used as a topical treatment of mild to moderate inflammatory acne vulgaris, due to its antibiotic effects on skin bacteria. Its effectiveness is similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845). Originally, the interest for the biological activity of AZA arose from studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. It was later shown that the causative agent of pyitirasis versicolor (the fungi Malassezia sp.) can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are competitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further research and development of a new topical drug for the treatment of hyperpigmentary disorders. Some of the advantages of Azelaic acid in this regard are that it possesses a middle-range of antityrosinase activity, it is inexpensive, and it is more easily incorporated into a base cream than other dicarboxylic acids. In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of the plants defensive response (PMID: 19342588). AZA is found in high abundance in several crop plants including wheat, rye, and barley. Azelaic acid has been detected, but not quantified in, a few different foods, such as asparagus, common beans, and potato. This could make azelaic acid a potential biomarker for the consumption of these foods. Azelaic acid is a precursor to a number of industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. Azelaic acid was the first simple acid to be reported in hemp seed oil (Cannabis sativa) by Bauer and Hazura in 1886 (PMID: 6991645). 1,7-Dicarboxyheptane 1,7-Heptanedicarboxylic acid 1,9-Nonanedioic acid Acide azelaique Acidum azelaicum Anchoic acid Azelainsaeure Azelex Finacea Lepargylic acid N-Nonanedioic acid Nonandisaeure Skinoren Nonanedioic acid 1,7-Heptanedicarboxylate 1,9-Nonanedioate Anchoate Lepargylate N-Nonanedioate Nonanedioate Azelaate Azalaic acid Azelaicacidtech Azelainic acid Azelate Emerox 1110 Emerox 1144 Emery'S L-110 Finevin Heptanedicarboxylic acid Nonanedioic acid azelaic acid Nonanedioic acid homopolymer Poly(azelaic anhydride) Polyazelaic anhydride Skinorem Azelaic acid, dilithium salt Azelaic acid, dipotassium salt Azelaic acid, disodium salt Azelaic acid, monosodium salt Azelaic acid, potassium salt Azelaic acid, sodium salt Monosodium azelate Azelaic acid Azelic acid alpha,omega-Nonanedioic acid α,ω-Nonanedioic acid C9H16O4 188.22 188.1049 nonanedioic acid azelaic acid 32733-99-6 OC(=O)CCCCCCCC(O)=O InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) BDJRBEYXGGNYIS-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Medium-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Medium-chain fatty acid Organic oxide Organic oxygen compound Organooxygen compound Dicarboxylic acids Dicarboxylic acids alpha,omega-dicarboxylic acid water_solubility 2.4 mg/mL logp 1.57 HANSCH,C ET AL. (1995) melting_point 106.5 °C logp 1.37 ALOGPS logs -1.92 ALOGPS logp 1.82 ChemAxon pka_strongest_acidic 4.15 ChemAxon iupac nonanedioic acid ChemAxon average_mass 188.22 ChemAxon mono_mass 188.1049 ChemAxon smiles OC(=O)CCCCCCCC(O)=O ChemAxon formula C9H16O4 ChemAxon inchi InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) ChemAxon inchikey BDJRBEYXGGNYIS-UHFFFAOYSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 46.54 ChemAxon polarizability 20.5 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB00548 FDB012192 2266 2179 C08261 48131 C00045634 CPD0-1265 Azelaic_Acid 5750 Nguyen QH, Bui TP: Azelaic acid: pharmacokinetic and pharmacodynamic properties and its therapeutic role in hyperpigmentary disorders and acne. Int J Dermatol. 1995 Feb;34(2):75-84. doi: 10.1111/j.1365-4362.1995.tb03583.x. 7737781 Mackrides PS, Shaughnessy AF: Azelaic acid therapy for acne. Am Fam Physician. 1996 Dec;54(8):2457-9. 8961845 Jung HW, Tschaplinski TJ, Wang L, Glazebrook J, Greenberg JT: Priming in systemic plant immunity. Science. 2009 Apr 3;324(5923):89-91. doi: 10.1126/science.1170025. 19342588 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:34:35 UTC 2020-08-04 22:28:18 UTC CDB000391 Vitamin K Vitamin K is often called vitamin K1, also known as Phylloquinone or Phytonadione. Vitamin K1 is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with 2-methyl and 3-phytyl substituents. Vitamin K belongs to a family of phylloquinones that contain a ring of 2-methyl-1,4-naphthoquinone and an isoprenoid side chain. Vitamin K1 has only one double bond on the proximal isoprene unit. Several forms of vitamin K have been identified: vitamin K1 derived from plants, vitamin K2 (menaquinone) from bacteria and vitamin K3, synthetic naphthoquinone provitamins such as menadione (PMID: 27337968). The synthetic Vitamin K, K3, is toxic to animals as it interferes with glutathione. Vitamin K1 is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. Rich sources of vitamin K1 include green plants, algae, and photosynthetic bacteria. It is found naturally in a wide variety of green plants including Cannabis sativa (PMID: 6991645). The plant derived Vitamin K1 is used by animals and is converted to the following coagulation factors in the liver: active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X). Vitamin K1 is concerted to Vitamin K2 by the gut microflora. Vitamin K1 is an antidote for coumatetralyl, the anti-coagulant rodent poison. Vitamin K1 has antihemorrhagic and prothrombogenic activity and is used to treat bleeding disorders which include in warfarin overdose, vitamin K deficiency, and obstructive jaundice ( https://www.ncbi.nlm.nih.gov/books/NBK551578/). C31H46O2 450.71 450.3498 2-methyl-3-[(7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione 2-methyl-3-[(7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione 12001-79-5 CC(C)CCC[C@H](C)CCC[C@@H](C)CCCC(C)=CCC1=C(C)C(=O)C2=CC=CC=C2C1=O InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/t23-,24+/m0/s1 MBWXNTAXLNYFJB-BJKOFHAPSA-N logp 8.48 ALOGPS logs -6.88 ALOGPS logp 9.7 ChemAxon pka_strongest_basic -7.2 ChemAxon iupac 2-methyl-3-[(7R,11S)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione ChemAxon average_mass 450.71 ChemAxon mono_mass 450.3498 ChemAxon smiles CC(C)CCC[C@H](C)CCC[C@@H](C)CCCC(C)=CCC1=C(C)C(=O)C2=CC=CC=C2C1=O ChemAxon formula C31H46O2 ChemAxon inchi InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/t23-,24+/m0/s1 ChemAxon inchikey MBWXNTAXLNYFJB-BJKOFHAPSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 142.96 ChemAxon polarizability 57.35 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Basset GJ, Latimer S, Fatihi A, Soubeyrand E, Block A: Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions. Mini Rev Med Chem. 2017;17(12):1028-1038. doi: 10.2174/1389557516666160623082714. 27337968 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:34:37 UTC 2020-09-11 20:09:01 UTC CDB000018 Cannabigerolic acid Cannabigerolic acid, CBGA, is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. CBGA is a dihydroxybenzoic acid derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. CBGA is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, CBGA can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. CBGA is a key biosynthetic precursor of Delta (9)-tetrahydrocannabinol, the main psychoactive component of Cannabis sativa.  As mentioned above, olivetolic acid and geranyl diphosphate are synthesized into CBGA. The CBGA is converted in the plant by CBCA synthase, cannabidiolic acid synthase (CBDA synthase) and tetrahydrocannabinolic acid synthase (THCA synthase) into CBCA, CBDA and tetrahydrocannabinolic acid (THCA).The THCA can be decarboxylated into THC by drying and heating plant material. Therefore, CBGA is an important cannabinoid found in cannabis. Because of its biosynthetic relationship to other psychoactive compounds, many efforts have been addressed to find alternative ways of producing it, particularly in yeast (PMID: 28694184) Additionally, cannabigerolic acid has shown antibiotic properties (PMID: 6991645). Cannabigerolic acid C22H32O4 360.49 360.2301 3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid 3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid 25555-57-1 CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26) SEEZIOZEUUMJME-UHFFFAOYSA-N belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Hydroxybenzoic acid derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aromatic monoterpenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Monocyclic monoterpenoids Organic oxides Organooxygen compounds Resorcinols Salicylic acids Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Dihydroxybenzoic acid Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Monocyclic monoterpenoid Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound Phenol Resorcinol Salicylic acid Salicylic acid or derivatives Vinylogous acid logp 5.31 ALOGPS logs -4.48 ALOGPS logp 7.35 ChemAxon pka_strongest_acidic 2.92 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid ChemAxon average_mass 360.49 ChemAxon mono_mass 360.2301 ChemAxon smiles CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O ChemAxon formula C22H32O4 ChemAxon inchi InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26) ChemAxon inchikey SEEZIOZEUUMJME-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 108.77 ChemAxon polarizability 42.63 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 3082240 FDB030712 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Zirpel B, Degenhardt F, Martin C, Kayser O, Stehle F: Engineering yeasts as platform organisms for cannabinoid biosynthesis. J Biotechnol. 2017 Oct 10;259:204-212. doi: 10.1016/j.jbiotec.2017.07.008. Epub 2017 Jul 8. 28694184 1.0 2020-03-19 00:34:41 UTC 2020-08-06 23:16:41 UTC CDB000011 Cannabigerolic acid monomethylether Cannabigerolic acid monomethyl ether or CBGAM is the methylated derivative of cannabigerolic acid in position four of the aromatic ring. As such, it is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. As a derivative of cannabigerolic acid, it is derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. CBGAM is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabigerolic acid monomethylether can be considered a polyketide and a monoterpenoid. In a study of the biosynthetic pathway of cannabinoid acids using four strains of Cannibus sativa L. (Mexican, Minamioshihara-1 and Domestic-l and 2; D-l and D2), 3 of the 4 strains produced THC as the major constituent but not the Domestic 2 strain, which only produced cannabigerolic acid. The Mexican strain also produced CBGAM as second major constituent ( https://www.thevespiary.org/rhodium/Rhodium/Vespiary/talk/files/4661-Biosynthesis-of-cannabinoid-acids-6d99.pdf). This suggested that all cannabis plants do not produce THC and some may accumulate other intermediates in the pathway to THC such as CBGAM.   C23H34O4 374.52 374.2457 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-pentylbenzoic acid 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-pentylbenzoic acid 29624-08-6 CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O InChI=1S/C23H34O4/c1-6-7-8-12-18-15-20(27-5)19(22(24)21(18)23(25)26)14-13-17(4)11-9-10-16(2)3/h10,13,15,24H,6-9,11-12,14H2,1-5H3,(H,25,26)/b17-13+ VAFRUJRAAHLCFZ-GHRIWEEISA-N belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. P-methoxybenzoic acids and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Aromatic monoterpenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Monocyclic monoterpenoids Organic oxides Phenoxy compounds Salicylic acids Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Aromatic monoterpenoid Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Hydroxybenzoic acid Methoxybenzene Methoxyphenol Monocyclic monoterpenoid Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-methoxybenzoic acid or derivatives Phenol Phenol ether Phenoxy compound Salicylic acid Salicylic acid or derivatives Vinylogous acid logp 5.56 ALOGPS logs -5.09 ALOGPS logp 7.5 ChemAxon pka_strongest_acidic 2.9 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 3-(3,7-dimethylocta-2,6-dien-1-yl)-2-hydroxy-4-methoxy-6-pentylbenzoic acid ChemAxon average_mass 374.52 ChemAxon mono_mass 374.2457 ChemAxon smiles CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O ChemAxon formula C23H34O4 ChemAxon inchi InChI=1S/C23H34O4/c1-6-7-8-12-18-15-20(27-5)19(22(24)21(18)23(25)26)14-13-17(4)11-9-10-16(2)3/h10,13,15,24H,6-9,11-12,14H2,1-5H3,(H,25,26)/b17-13+ ChemAxon inchikey VAFRUJRAAHLCFZ-GHRIWEEISA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 113.25 ChemAxon polarizability 44.44 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 24739091 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Thakker C, Martinez I, San KY, Bennett GN: Succinate production in Escherichia coli. Biotechnol J. 2012 Feb;7(2):213-24. doi: 10.1002/biot.201100061. Epub 2011 Sep 20. 21932253 Briere JJ, Favier J, El Ghouzzi V, Djouadi F, Benit P, Gimenez AP, Rustin P: Succinate dehydrogenase deficiency in human. Cell Mol Life Sci. 2005 Oct;62(19-20):2317-24. doi: 10.1007/s00018-005-5237-6. 16143825 Rustin P, Rotig A: Inborn errors of complex II--unusual human mitochondrial diseases. Biochim Biophys Acta. 2002 Jan 17;1553(1-2):117-22. doi: 10.1016/s0005-2728(01)00228-6. 11803021 Yang M, Soga T, Pollard PJ: Oncometabolites: linking altered metabolism with cancer. J Clin Invest. 2013 Sep;123(9):3652-8. doi: 10.1172/JCI67228. Epub 2013 Sep 3. 23999438 Sciacovelli M, Frezza C: Oncometabolites: Unconventional triggers of oncogenic signalling cascades. Free Radic Biol Med. 2016 Nov;100:175-181. doi: 10.1016/j.freeradbiomed.2016.04.025. Epub 2016 Apr 23. 27117029 Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. 22292465 Sauer M, Porro D, Mattanovich D, Branduardi P: Microbial production of organic acids: expanding the markets. Trends Biotechnol. 2008 Feb;26(2):100-8. doi: 10.1016/j.tibtech.2007.11.006. Epub 2008 Jan 11. 18191255 Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. 26360870 Gunnarsson IB, Kuglarz M, Karakashev D, Angelidaki I: Thermochemical pretreatments for enhancing succinic acid production from industrial hemp (Cannabis sativa L.). Bioresour Technol. 2015 Apr;182:58-66. doi: 10.1016/j.biortech.2015.01.126. Epub 2015 Feb 4. 25682224 1.0 2020-03-19 00:34:44 UTC 2020-09-11 20:09:01 UTC CDB000003 Cannabigerol Cannabigerol or CBG is the decarboxylated derivative of cannabigerolic acid, a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. CBG is a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. It is biosynthetically derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. It is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabigerol can be considered a polyketide, a monoterpenoid and a resorcinol. Cannabigerolic acid is a key biosynthetic precursor of Delta (9)-tetrahydrocannabinol, the main psychoactive component of Cannabis sativa. CBG is a minor constituent of cannabis (approximately 1% of dry weight). During growth, most of the CBG present in the plant‚Äôs tissues is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD) (PMID: 26836472). In contrast to THC (PMID 28120232), CBG antagonizes cannabinoid receptor type 1 (CB1) receptors and is both an alpha2-adrenoceptor agonist and moderate serotonin Type 1A (5HT1A) receptor antagonist (PMID: 20002104).  Cannabigerol has binding affinity for both CB1 and cannabinoid receptor type 2 (CB2). CBG is being investigated as a possible treatment for inflammatory diseases, such as colitis (PMID: 29562280). CBG (E)-2-(3,7-Dimethylocta-2,6-dien-1-yl)-5-pentylbenzene-1,3-diol 2-((2E)-3,7-Dimethylocta-2,6-dienyl)-5-pentylbenzene-1,3-diol CBG-C5 C21H32O2 316.49 316.2402 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-pentylbenzene-1,3-diol cannabigerol 25654-31-3 CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 InChI=1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+ QXACEHWTBCFNSA-SFQUDFHCSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Hydrocarbon derivatives Monocyclic monoterpenoids Organooxygen compounds Resorcinols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound Phenol Resorcinol monoterpenoid logp 6.99 ALOGPS logs -4.79 ALOGPS logp 7.05 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-pentylbenzene-1,3-diol ChemAxon average_mass 316.49 ChemAxon mono_mass 316.2402 ChemAxon smiles CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 ChemAxon formula C21H32O2 ChemAxon inchi InChI=1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+ ChemAxon inchikey QXACEHWTBCFNSA-SFQUDFHCSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 101.51 ChemAxon polarizability 39.04 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20219 5315659 Cannabigerol Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. 26836472 Couch DG, Maudslay H, Doleman B, Lund JN, O'Sullivan SE: The Use of Cannabinoids in Colitis: A Systematic Review and Meta-Analysis. Inflamm Bowel Dis. 2018 Mar 19;24(4):680-697. doi: 10.1093/ibd/izy014. 29562280 Morales P, Hurst DP, Reggio PH: Molecular Targets of the Phytocannabinoids: A Complex Picture. Prog Chem Org Nat Prod. 2017;103:103-131. doi: 10.1007/978-3-319-45541-9_4. 28120232 Cascio MG, Gauson LA, Stevenson LA, Ross RA, Pertwee RG: Evidence that the plant cannabinoid cannabigerol is a highly potent alpha2-adrenoceptor agonist and moderately potent 5HT1A receptor antagonist. Br J Pharmacol. 2010 Jan;159(1):129-41. doi: 10.1111/j.1476-5381.2009.00515.x. Epub 2009 Dec 4. 20002104 1.0 2020-03-19 00:34:46 UTC 2020-08-04 22:24:07 UTC CDB000004 Cannabigerol monomethylether Cannabigerol monomethylether is a methoxylated derivative of cannabigerol, which is a phytocannabinoid. Cannabigerol is a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. It is biosynthetically derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. It is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabigerol monomethylether can be considered a polyketide, a monoterpenoid and a resorcinol. Cannabigerol is a minor constituent of cannabis (approximately 1 % of dry weight). During growth, most of the cannabigerol present in the plant‚Äôs tissues is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD) (PMID: 26836472). Cannabigerol monomethylether was first reported to be isolated from the japanese ‚ÄúMinamioshihara No.1‚Äù domestic variety in 1968 (PMID: 5706840). C22H34O2 330.51 330.2559 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 InChI=1S/C22H34O2/c1-6-7-8-12-19-15-21(23)20(22(16-19)24-5)14-13-18(4)11-9-10-17(2)3/h10,13,15-16,23H,6-9,11-12,14H2,1-5H3/b18-13+ KASVLYINZPAMNS-QGOAFFKASA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Monocyclic monoterpenoids Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound logp 7.21 ALOGPS logs -5.30 ALOGPS logp 7.19 ChemAxon pka_strongest_acidic 9.39 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3-methoxy-5-pentylphenol ChemAxon average_mass 330.51 ChemAxon mono_mass 330.2559 ChemAxon smiles CCCCCC1=CC(OC)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 ChemAxon formula C22H34O2 ChemAxon inchi InChI=1S/C22H34O2/c1-6-7-8-12-19-15-21(23)20(22(16-19)24-5)14-13-18(4)11-9-10-17(2)3/h10,13,15-16,23H,6-9,11-12,14H2,1-5H3/b18-13+ ChemAxon inchikey KASVLYINZPAMNS-QGOAFFKASA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 105.99 ChemAxon polarizability 41.56 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 13864080 Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. 26836472 Yamauchi T, Shoyama Y, Matsuo Y, Nishioka I: Cannabigerol monomethyl ether, a new component of hemp. Chem Pharm Bull (Tokyo). 1968 Jun;16(6):1164-5. doi: 10.1248/cpb.16.1164. 5706840 1.0 2020-03-19 00:34:51 UTC 2020-08-04 22:24:07 UTC CDB000005 Cannabigerovarinic acid Cannabigerovarinic acid (CBGVA) is the C3 analogue of cannabigerolic acid (CBGA). CBGVA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabigerovarinic acid is a dihydroxybenzoic acid derived from divarinic acid on which the hydrogen at position 3 is substituted by a geranyl group. Cannabigerovarinic acid is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from divarinic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabigerovarinic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups substituting the benzene ring. Cannabigerovarinic acid is a key biosynthetic precursor of C3-cannabinoids. Cannabigerovarinic acid is an important cannabinoid found in cannabis and due to its biosynthetic relationship to other compounds efforts have been addressed to find alternative ways of producing it (in yeast; PMID: 30814733). A cell free system was developed to produces cannabinoids, including cannabigerovarinic acid, from glucose by supplying several enzymes that create isoprenylate derivatives and these prenylated cannabinoid intermediates (PMID: 30718485). The yeast and cell free systems produce these important natural products that are difficult to make or purify from living organisms. C20H28O4 332.44 332.1988 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O InChI=1S/C20H28O4/c1-5-7-15-12-17(21)16(19(22)18(15)20(23)24)11-10-14(4)9-6-8-13(2)3/h8,10,12,21-22H,5-7,9,11H2,1-4H3,(H,23,24)/b14-10+ FAVCTJGKHFHFHJ-GXDHUFHOSA-N belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Hydroxybenzoic acid derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aromatic monoterpenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Organooxygen compounds Phenylpropanes Resorcinols Salicylic acids Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Dihydroxybenzoic acid Hydrocarbon derivative Hydroxybenzoic acid Monocyclic monoterpenoid Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenylpropane Resorcinol Salicylic acid Salicylic acid or derivatives Vinylogous acid logp 4.61 ALOGPS logs -4.27 ALOGPS logp 6.46 ChemAxon pka_strongest_acidic 2.92 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid ChemAxon average_mass 332.44 ChemAxon mono_mass 332.1988 ChemAxon smiles CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O ChemAxon formula C20H28O4 ChemAxon inchi InChI=1S/C20H28O4/c1-5-7-15-12-17(21)16(19(22)18(15)20(23)24)11-10-14(4)9-6-8-13(2)3/h8,10,12,21-22H,5-7,9,11H2,1-4H3,(H,23,24)/b14-10+ ChemAxon inchikey FAVCTJGKHFHFHJ-GXDHUFHOSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 99.56 ChemAxon polarizability 38.37 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444383 Luo X, Reiter MA, d'Espaux L, Wong J, Denby CM, Lechner A, Zhang Y, Grzybowski AT, Harth S, Lin W, Lee H, Yu C, Shin J, Deng K, Benites VT, Wang G, Baidoo EEK, Chen Y, Dev I, Petzold CJ, Keasling JD: Complete biosynthesis of cannabinoids and their unnatural analogues in yeast. Nature. 2019 Mar;567(7746):123-126. doi: 10.1038/s41586-019-0978-9. Epub 2019 Feb 27. 30814733 Valliere MA, Korman TP, Woodall NB, Khitrov GA, Taylor RE, Baker D, Bowie JU: A cell-free platform for the prenylation of natural products and application to cannabinoid production. Nat Commun. 2019 Feb 4;10(1):565. doi: 10.1038/s41467-019-08448-y. 30718485 Song SH, Vieille C: Recent advances in the biological production of mannitol. Appl Microbiol Biotechnol. 2009 Aug;84(1):55-62. doi: 10.1007/s00253-009-2086-5. Epub 2009 Jul 4. 19578847 Wisselink HW, Mars AE, van der Meer P, Eggink G, Hugenholtz J: Metabolic engineering of mannitol production in Lactococcus lactis: influence of overexpression of mannitol 1-phosphate dehydrogenase in different genetic backgrounds. Appl Environ Microbiol. 2004 Jul;70(7):4286-92. doi: 10.1128/AEM.70.7.4286-4292.2004. 15240312 Zhang M, Gu L, Cheng C, Ma J, Xin F, Liu J, Wu H, Jiang M: Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies. World J Microbiol Biotechnol. 2018 Feb 26;34(3):41. doi: 10.1007/s11274-018-2425-8. 29480337 1.0 2020-03-19 00:34:54 UTC 2020-08-04 22:24:07 UTC CDB000006 Cannabigerovarin Cannabidivarin (CBDV) is a non-psychoactive cannabinoid found within medical Cannabis. It is one of over 100 cannabinoids identified from the Cannabis plants that can modulate the physiological activity of cannabis, or marijuana (PubMed ID 23408483). CBDV is the C3 analogue of cannabidiol (CBD). Notably, both cannabidiol and CBDV have demonstrated anticonvulsant activity in animal and human models and are demonstrating promising clinical trial results (PMID: 22970845; PMID: 25029033; PMID: 29290836; PMID: 29588939). Other cannabinoids with some evidence of anti-epileptic activity include Tetrahydrocannabivarin (THCV) and Œî9-tetrahydrocannabinolic acid. While the primary components of cannabis, CBD and THC, have been shown to modulate many of their physiological effects through their binding to the cannabinoid-1 (CB1R) and cannabinoid-2 (CB2R) receptors, the investigational cannabinoids with anticonvulsant action mostly use mechanisms that do not involve these two endocannabinoid receptors. The anti-epileptic activity of CBD and CBDV is thought to be modulated by their effects on transient receptor potential cation channel subfamily V member 1 (TRPV1), also known as the capsaicin receptor, which is a member of a large family of ion channels that are involved in the onset and progression of several types of epilepsy. CBD and CBDV have been shown to dose-dependently activate and then desensitize TRPV1 as well as TRPV2 and TRPA1 channels (PMID 25029033; PMID: 29842819; PMID: 21175579). Desensitization of these ion channels is a potential mechanism by which these molecules cause a reduction of neuronal hyperexcitability that contributes to epileptic activity and seizures. CBDV has also been shown to inhibit the activity of diacylglycerol (DAG) lipase-Œ±, the primary enzyme responsible for the synthesis of the endocannabinoid, 2-arachidonoylglycerol (2-AG) (PMID: 24282673; PMID: 14610053). The clinical implications of this are unclear however, as this interaction has not been shown to affect CBDV's anticonvulsant activity. Cannabidivarin is being actively developed by GW Pharmaceuticals as the experimental compound GWP42006 as it has "shown the ability to treat seizures in pre-clinical models of epilepsy with significantly fewer side effects than currently approved anti-epileptic drugs". Unfortunately, as of February 2018, GW Pharmaceuticals announced that their Phase 2a placebo-controlled study of CBDV for focal seizure did not reach its primary endpoints. They will continue to study its use in epilepsy, however, and are expanding their investigations to include its potential use in Autism Spectrum Disorder, Rett syndrome and Fragile X among others. In October 2017 CBDV was given orphan designation by the European Medicines Agency for use in Rett Syndrome and again in February 2018 for treatment of Fragile X Syndrome. C19H28O2 288.43 288.2089 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-propylbenzene-1,3-diol 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-propylbenzene-1,3-diol 55824-11-8 CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 InChI=1S/C19H28O2/c1-5-7-16-12-18(20)17(19(21)13-16)11-10-15(4)9-6-8-14(2)3/h8,10,12-13,20-21H,5-7,9,11H2,1-4H3/b15-10+ YJYIDZLGVYOPGU-XNTDXEJSSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Hydrocarbon derivatives Monocyclic monoterpenoids Organooxygen compounds Phenylpropanes Resorcinols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound Phenol Phenylpropane Resorcinol logp 5.91 ALOGPS logs -4.57 ALOGPS logp 6.16 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-propylbenzene-1,3-diol ChemAxon average_mass 288.43 ChemAxon mono_mass 288.2089 ChemAxon smiles CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 ChemAxon formula C19H28O2 ChemAxon inchi InChI=1S/C19H28O2/c1-5-7-16-12-18(20)17(19(21)13-16)11-10-15(4)9-6-8-14(2)3/h8,10,12-13,20-21H,5-7,9,11H2,1-4H3/b15-10+ ChemAxon inchikey YJYIDZLGVYOPGU-XNTDXEJSSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 92.31 ChemAxon polarizability 35.2 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444407 Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ: Cannabidivarin is anticonvulsant in mouse and rat. Br J Pharmacol. 2012 Dec;167(8):1629-42. doi: 10.1111/j.1476-5381.2012.02207.x. 22970845 Iannotti FA, Hill CL, Leo A, Alhusaini A, Soubrane C, Mazzarella E, Russo E, Whalley BJ, Di Marzo V, Stephens GJ: Nonpsychotropic plant cannabinoids, cannabidivarin (CBDV) and cannabidiol (CBD), activate and desensitize transient receptor potential vanilloid 1 (TRPV1) channels in vitro: potential for the treatment of neuronal hyperexcitability. ACS Chem Neurosci. 2014 Nov 19;5(11):1131-41. doi: 10.1021/cn5000524. Epub 2014 Jul 29. 25029033 Capasso A: Do Cannabinoids Confer Neuroprotection Against Epilepsy? An Overview. Open Neurol J. 2017 Dec 18;11:61-73. doi: 10.2174/1874205X01711010061. eCollection 2017. 29290836 Morano A, Cifelli P, Nencini P, Antonilli L, Fattouch J, Ruffolo G, Roseti C, Aronica E, Limatola C, Di Bonaventura C, Palma E, Giallonardo AT: Cannabis in epilepsy: From clinical practice to basic research focusing on the possible role of cannabidivarin. Epilepsia Open. 2016 Sep 19;1(3-4):145-151. doi: 10.1002/epi4.12015. eCollection 2016 Dec. 29588939 Ruzic Zecevic D, Folic M, Tantoush Z, Radovanovic M, Babic G, Jankovic SM: Investigational cannabinoids in seizure disorders, what have we learned thus far? Expert Opin Investig Drugs. 2018 Jun;27(6):535-541. doi: 10.1080/13543784.2018.1482275. Epub 2018 Jun 6. 29842819 De Petrocellis L, Ligresti A, Moriello AS, Allara M, Bisogno T, Petrosino S, Stott CG, Di Marzo V: Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol. 2011 Aug;163(7):1479-94. doi: 10.1111/j.1476-5381.2010.01166.x. 21175579 Amada N, Yamasaki Y, Williams CM, Whalley BJ: Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression. PeerJ. 2013 Nov 21;1:e214. doi: 10.7717/peerj.214. eCollection 2013. 24282673 Bisogno T, Howell F, Williams G, Minassi A, Cascio MG, Ligresti A, Matias I, Schiano-Moriello A, Paul P, Williams EJ, Gangadharan U, Hobbs C, Di Marzo V, Doherty P: Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J Cell Biol. 2003 Nov 10;163(3):463-8. doi: 10.1083/jcb.200305129. 14610053 1.0 2020-03-19 00:34:58 UTC 2020-08-04 22:28:18 UTC CDB000398 Cannabichromenic acid Cannabichromenic acid (CBCA) is a biosynthetic derivative of cannabigerolic acid (CBGA). It is a non-psychoactive component of cannabis and is one of the more than 100 cannabinoids found in Cannabis sativa plants. As its precursor, cannabigerolic acid, CBCA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabichromenic acid is characterized by the presence of a chromene moiety in the center of the structure. This chromene arrangement results from the cyclization of the isoprenoid sidechain on to the hydroxyl group in position four of cannabigerolic acid, yielding a pyrane type ring. Cannabichromenic acid is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabichromenic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. CBC is not active at the  cannabinoid-1 (CB1) and cannabinoid-2 (CB2) receptors, but is an agonist of  transient receptor potential ankyrin 1 TRPA1 and less potently, an agonist of  transient receptor potential cation channel, subfamily V, member 3 and 4 (TRPV3;  TRPV4;  PMID 28120231). 5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylate C22H30O4 358.48 358.2144 (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromene-6-carboxylic acid (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentylchromene-6-carboxylic acid 20408-52-0 CCCCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O InChI=1S/C22H30O4/c1-5-6-7-10-16-14-18-17(20(23)19(16)21(24)25)11-13-22(4,26-18)12-8-9-15(2)3/h9,11,13-14,23H,5-8,10,12H2,1-4H3,(H,24,25)/t22-/m0/s1 HRHJHXJQMNWQTF-QFIPXVFZSA-N belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Salicylic acid and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Vinylogous acids 1-benzopyran 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzopyran Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Salicylic acid or derivatives Vinylogous acid logp 5.69 ALOGPS logs -4.73 ALOGPS logp 6.91 ChemAxon pka_strongest_acidic 2.87 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromene-6-carboxylic acid ChemAxon average_mass 358.48 ChemAxon mono_mass 358.2144 ChemAxon smiles CCCCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O ChemAxon formula C22H30O4 ChemAxon inchi InChI=1S/C22H30O4/c1-5-6-7-10-16-14-18-17(20(23)19(16)21(24)25)11-13-22(4,26-18)12-8-9-15(2)3/h9,11,13-14,23H,5-8,10,12H2,1-4H3,(H,24,25)/t22-/m0/s1 ChemAxon inchikey HRHJHXJQMNWQTF-QFIPXVFZSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 106.86 ChemAxon polarizability 41.69 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 92448135 Turner SE, Williams CM, Iversen L, Whalley BJ: Molecular Pharmacology of Phytocannabinoids. Prog Chem Org Nat Prod. 2017;103:61-101. doi: 10.1007/978-3-319-45541-9_3. 28120231 1.0 2020-03-19 00:35:02 UTC 2020-09-11 20:09:01 UTC CDB000007 Cannabichromene Cannabichromene, also known as CBC, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. Cannabichromene is a neutral compound. Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is one of the hundreds of cannabinoids found in the cannabis plant and is therefore a phytocannabinoid. It bears structural similarity to other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC is a product of the decarboxylation of cannabichromenic acid (CBCA), which occurs over time or after reaching temperatures above 90 ¬∞C. CBCA is a product of the cyclization of the main cannabinoid precursor, cannabigerolic acid (CBGA). CBC and its derivatives are as abundant as cannabinols in cannabis. CBC is not scheduled by the Convention on Psychotropic Substances. CBC has shown interesting anti-inflammatory activities in pre-clinical trials (PMID: 20619971). CBC is non-psychoactive and does not affect the psychoactivity of THC (PMID: 16148455). CBC acts on the transient receptor potential cation channel subfamily V member 1 (TRPV1) and transient receptor potential ankyrin 1 (TRPA1) receptors, interfering with their ability to break down endocannabinoids (the bodies endogenous cannabinoids, such as anandamide and 2-arachidonoylglycerol, 2-AG, the endogenous agonist for the cannabinoid-1 receptor, CB1 and primary ligand for cannabinoid-2 receptor, CB2). C21H30O2 314.47 314.2246 (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentylchromen-5-ol 20675-51-8 CCCCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1 InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3/t21-/m0/s1 UVOLYTDXHDXWJU-NRFANRHFSA-N belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 7.04 ALOGPS logs -5.31 ALOGPS logp 6.6 ChemAxon pka_strongest_acidic 9.47 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3/t21-/m0/s1 ChemAxon inchikey UVOLYTDXHDXWJU-NRFANRHFSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 99.6 ChemAxon polarizability 38.28 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21668219 DeLong GT, Wolf CE, Poklis A, Lichtman AH: Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Delta(9)-tetrahydrocannabinol. Drug Alcohol Depend. 2010 Nov 1;112(1-2):126-33. doi: 10.1016/j.drugalcdep.2010.05.019. 20619971 Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H: Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids. Behav Pharmacol. 2005 Sep;16(5-6):487-96. doi: 10.1097/00008877-200509000-00023. 16148455 1.0 2020-03-19 00:35:05 UTC 2020-08-04 22:24:07 UTC CDB000008 Cannabichromevarinic acid Cannabichromevarinic acid (CBCVA), a biosynthetic derivative of cannabigerovarinic acid (CBGVA),  is a non-psychoactive component of cannabis. CBCVA is a C3 analogue of cannabichromenic acid. CBCVA is one of the more than 100 cannabinoids found in Cannabis sativa plants. As its precursor, cannabigerovarinic acid, CBCVA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabichromenic acid is characterized by the presence of a chromene (1-benzopyran) moiety in the center of the structure. This chromene arrangement results from the cyclization of the isoprenoid sidechain onto the hydroxyl group in position four of cannabigerovarinic acid, yielding a pyrane type ring. Cannabichromevarinic acid is a molecule of mixed biosynthetic oDOI: rigin, in which its aromatic moiety (derived from divarinic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabichromevarinic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring.  CBCVA was one of four propyl cannabinoid acids isolated from Thai Cannabis, 'Meao Variant' in 1977 (DOI: 10.1248/cpb.25.2306). (2S)-5-Hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylate C20H26O4 330.42 330.1831 (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylic acid (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propylchromene-6-carboxylic acid 64898-02-8 CCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O InChI=1S/C20H26O4/c1-5-7-14-12-16-15(18(21)17(14)19(22)23)9-11-20(4,24-16)10-6-8-13(2)3/h8-9,11-12,21H,5-7,10H2,1-4H3,(H,22,23)/t20-/m0/s1 OIVPAQDCMDYIIL-FQEVSTJZSA-N belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Salicylic acid and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Vinylogous acids 1-benzopyran 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzopyran Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Salicylic acid or derivatives Vinylogous acid logp 5.06 ALOGPS logs -4.24 ALOGPS logp 6.02 ChemAxon pka_strongest_acidic 2.87 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2S)-5-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromene-6-carboxylic acid ChemAxon average_mass 330.42 ChemAxon mono_mass 330.1831 ChemAxon smiles CCCC1=CC2=C(C=C[C@](C)(CCC=C(C)C)O2)C(O)=C1C(O)=O ChemAxon formula C20H26O4 ChemAxon inchi InChI=1S/C20H26O4/c1-5-7-14-12-16-15(18(21)17(14)19(22)23)9-11-20(4,24-16)10-6-8-13(2)3/h8-9,11-12,21H,5-7,10H2,1-4H3,(H,22,23)/t20-/m0/s1 ChemAxon inchikey OIVPAQDCMDYIIL-FQEVSTJZSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 97.66 ChemAxon polarizability 37.1 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-19 00:35:08 UTC 2020-08-04 22:24:07 UTC CDB000009 Cannabichromevarin Cannabichromevarin (CBCV) belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic structure made up of a benzene and a pyran ring fused together, so that the oxygen atom is at position one. Cannabichromevarin is a neutral compound. CBCV is the C3 analogue of cannabichromene (CBC) and bears structural similarity to other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBCV is a product of the decarboxylation of cannabichromevarinic acid (CBCVA), which occurs over time or after reaching temperatures above 90 ¬∞C. CBCVA is a product of the cyclization of cannabigerovarinic acid (CBGVA) (PMID: 30023762) (https://doi.org/10.1016/B978-0-12-800756-3.00002-8). CBCV and its derivatives are as abundant as cannabinols in cannabis plants. CBCV is not psychoactive and is not scheduled by the Convention on Psychotropic Substances. CBCV is a propyl cannabinoid and an effective anticonvulsant used to treat brain cancer and epilepsy (https://en.wikipedia.org/wiki/Cannabichromevarin). C19H26O2 286.42 286.1933 (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromen-5-ol (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propylchromen-5-ol 41408-19-9 CCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1 InChI=1S/C19H26O2/c1-5-7-15-12-17(20)16-9-11-19(4,21-18(16)13-15)10-6-8-14(2)3/h8-9,11-13,20H,5-7,10H2,1-4H3/t19-/m0/s1 AAXZFUQLLRMVOG-IBGZPJMESA-N belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle logp 5.97 ALOGPS logs -4.78 ALOGPS logp 5.71 ChemAxon pka_strongest_acidic 9.47 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (2S)-2-methyl-2-(4-methylpent-3-en-1-yl)-7-propyl-2H-chromen-5-ol ChemAxon average_mass 286.42 ChemAxon mono_mass 286.1933 ChemAxon smiles CCCC1=CC(O)=C2C=C[C@](C)(CCC=C(C)C)OC2=C1 ChemAxon formula C19H26O2 ChemAxon inchi InChI=1S/C19H26O2/c1-5-7-15-12-17(20)16-9-11-19(4,21-18(16)13-15)10-6-8-14(2)3/h8-9,11-13,20H,5-7,10H2,1-4H3/t19-/m0/s1 ChemAxon inchikey AAXZFUQLLRMVOG-IBGZPJMESA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 90.4 ChemAxon polarizability 34.09 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 139496813 Lewis MM, Yang Y, Wasilewski E, Clarke HA, Kotra LP: Chemical Profiling of Medical Cannabis Extracts. ACS Omega. 2017 Sep 30;2(9):6091-6103. doi: 10.1021/acsomega.7b00996. Epub 2017 Sep 22. 30023762 1.0 2020-03-19 00:35:12 UTC 2020-09-11 20:09:01 UTC CDB000010 Cannabidiolic acid Cannabidiolic acid (CBDA) belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and, at least, one hydroxyl group. CBDA also belongs to the class of cannabis compounds known as cannabidiol. The biosynthesis of CBDA occurs through the cyclization of the isoprenoid side chain of cannabigerolic acid (CBGA) to yield a cyclohexene moiety, common to all cannabidiol-type cannabinoids. CBDA is one of the major cannabinoid compounds found in cannabis plants, particularly in the fiber-type varieties. Even though CBDA is a non-psychoactive component of Cannabis sativa, it has been proven to inhibit the migration of the highly invasive human breast cancer cell line MDA-MB-231. The apparent mechanism of action involves the inhibition of cAMP-dependent protein kinase A and the activation of Ras homolog family member A (RhoA; PMID: 22963825). Studies on mice have also shown that CBDA has a potential anticonvulsant activity (PMID: 31686510). 3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylic acid CBDA Cannabidiolate 3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylate 3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylic acid 3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylate 3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylate 3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylic acid Cannabidiol acid Cannabidiolcarboxylic acid C22H30O4 358.48 358.2144 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid cannabidiolic acid 1244-58-2 CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1C(O)=O InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1 WVOLTBSCXRRQFR-DLBZAZTESA-N belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Hydroxybenzoic acid derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aromatic monoterpenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Menthane monoterpenoids Monocarboxylic acids and derivatives Monocyclic monoterpenoids Organic oxides Organooxygen compounds Resorcinols Salicylic acids Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Dihydroxybenzoic acid Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Monocyclic monoterpenoid Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Phenol Resorcinol Salicylic acid Salicylic acid or derivatives Vinylogous acid Other aromatic polyketides Other aromatic polyketides dihydroxybenzoic acid phytocannabinoid polyketide resorcinols logp 4.55 ALOGPS logs -4.00 ALOGPS logp 6.63 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid ChemAxon average_mass 358.48 ChemAxon mono_mass 358.2144 ChemAxon smiles CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1C(O)=O ChemAxon formula C22H30O4 ChemAxon inchi InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1 ChemAxon inchikey WVOLTBSCXRRQFR-DLBZAZTESA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 105.79 ChemAxon polarizability 41.05 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C10784 3359 160570 CPD-7170 C00002642 Takeda S, Okajima S, Miyoshi H, Yoshida K, Okamoto Y, Okada T, Amamoto T, Watanabe K, Omiecinski CJ, Aramaki H: Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration. Toxicol Lett. 2012 Nov 15;214(3):314-9. doi: 10.1016/j.toxlet.2012.08.029. Epub 2012 Sep 8. 22963825 Anderson LL, Low IK, Banister SD, McGregor IS, Arnold JC: Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome. J Nat Prod. 2019 Nov 22;82(11):3047-3055. doi: 10.1021/acs.jnatprod.9b00600. Epub 2019 Nov 5. 31686510 Xiao S, Yu PH: A fluorometric high-performance liquid chromatography procedure for simultaneous determination of methylamine and aminoacetone in blood and tissues. Anal Biochem. 2009 Jan 1;384(1):20-6. doi: 10.1016/j.ab.2008.09.029. Epub 2008 Sep 25. 18845121 Pirisino R, Ghelardini C, De Siena G, Malmberg P, Galeotti N, Cioni L, Banchelli G, Raimondi L: Methylamine: a new endogenous modulator of neuron firing? Med Sci Monit. 2005 Aug;11(8):RA257-61. Epub 2005 Jul 25. 16049393 Dunkel P, Gelain A, Barlocco D, Haider N, Gyires K, Sperlagh B, Magyar K, Maccioni E, Fadda A, Matyus P: Semicarbazide-sensitive amine oxidase/vascular adhesion protein 1: recent developments concerning substrates and inhibitors of a promising therapeutic target. Curr Med Chem. 2008;15(18):1827-39. doi: 10.2174/092986708785133022. 18691041 Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. 22626821 1.0 2020-03-19 00:35:16 UTC 2020-09-11 20:09:01 UTC CDB000002 Cannabidiol Cannabidiol (CBD) is one of at least 85 active cannabinoids identified within the Cannabis plant. It is a major phytocannabinoid, accounting for up to 40% of the Cannabis plant's extract, that binds to a wide variety of physiological targets of the endocannabinoid system within the body. Although the exact medical implications are currently being investigated, CBD has shown promise as a therapeutic and pharmaceutical drug target as an analgesic, anticonvulsant, muscle relaxant, anxiolytic, antipsychotic and has shown neuroprotective, anti-inflammatory, and antioxidant activity, among other currently investigated uses (PMID: 26218440; PMID: 17828291). CBD's exact place within medical practice is still currently hotly debated. However as the body of evidence grows and legislation changes to reflect its wide-spread use, public and medical opinion have changed significantly with regards to its usefulness in a number of medical conditions ranging from anxiety to epilepsy. From a pharmacological perspective, Cannabis' (and CBD's) diverse receptor profile explains its potential application for such a wide variety of medical conditions. Cannabis contains more than 400 different chemical compounds, of which 61 are considered cannabinoids (PMID: 23408483). Cannabinoid receptors are utilized endogenously by the body through the endocannabinoid system, which includes a group of lipid proteins, enzymes, and receptors that are involved in many physiological processes. Through its modulation of neurotransmitter release, the endocannabinoid system regulates cognition, pain sensation, appetite, memory, sleep, immune function, and mood among many other bodily systems. These effects are largely mediated through two members of the G-protein coupled receptors family, cannabinoid receptors 1 and 2 (CB1 and CB2) (PMID: 26015168; PMID: 29533978). CB1 receptors are found in both the central and peripheral nervous systems, with most receptors localized to the hippocampus and amygdala of the brain. Physiological effects of using cannabis make sense in the context of its receptor activity as the hippocampus and amygdala are primarily involved with regulation of memory, fear, and emotion. In contrast, CB2 receptors are mainly found peripherally in immune cells, lymphoid tissue, and peripheral nerve terminals (PMID: 27086601). Tetrahydrocannabinol (THC) and cannabidiol (CBD) are two types of cannabinoids found naturally in the resin of the marijuana plant, both of which interact with the cannabinoid receptors that are found throughout the body. Although THC and CBD have been the most studied cannabinoids, there are many others identified to date including cannabinol (CBN), cannabigerol (CBG), Cannabidivarin (CBDV), and Tetrahydrocannabivarin (THCV) that can be found within the medical cannabis (PMID: 16199061). While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. If not provided in their activated form (such as through synthetic forms of THC like Dronabinol or Nabilone), THC and CBD are obtained through conversion from their precursors, tetrahydrocannabinolic acid-A (THCA-A) and cannabidiolic acid (CBDA), through decarboxylation reactions. This can be achieved through heating, smoking, vaporization, or baking of dried unfertilized female cannabis flowers. The primary psychoactive component of Cannabis, delta 9-tetrahydrocannabinol (Œî9-THC), demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors. This activity results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. In contrast to THC's weak agonist activity, CBD has been shown to act as a negative allosteric modulator of the CB1 receptor, the most abundant G-Protein Coupled Receptor (GPCR) in the body (PMID: 26218440). Allosteric regulation is achieved through the modulation of receptor activity on a functionally distinct site from the agonist or antagonist binding site which is clinically significant as direct agonists (such as THC) are limited by their psychomimetic effects such as changes to mood, memory, and anxiety (PMID: 26218440). In addition to the well-known activity on CB1 and CB2 receptors, there is further evidence that CBD also activates serotonin Type 1A, 2A,3A (HT1A/2A/3A) serotonergic and transient receptor potential cation channel subfamily V member 2 receptors (TRPV1‚Äì2) vanilloid receptors, antagonizes alpha-1 adrenergic and ¬µ-opioid receptors, inhibits synaptosomal uptake of noradrenaline, dopamine, serotonin and gamma-aminobutyric acid (GABA), and cellular uptake of anandamide, acts on mitochondria Ca2+ stores, blocks low-voltage-activated (T-type) Ca2+ channels, stimulates activity of the inhibitory glycine-receptor, and inhibits activity of fatty amide hydrolase (FAAH) (PMID: 26264914; PMID: 24281562). CBD is currently available in Canada within a 1:1 formulation with tetrahydrocannbinol (THC) (as the formulation known as "nabiximols"; as the brand name product Sativex). It is approved for use as adjunctive treatment for symptomatic relief of spasticity in adult patients with multiple sclerosis (MS). Sativex was also given a conditional Notice of Compliance (NOC/c) for use as adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis and as adjunctive analgesic treatment for moderate to severe pain in adult patients with advanced cancer. In April 2018, a Food and Drug Administration advisory panel unanimously recommended approval of Epidiolex (cannabidiol oral solution) for the treatment of two rare forms of epilepsy - Lennox-Gastaut syndrome and Dravet syndrome, which are among the two most difficult types of epilepsy to treat. Epidiolex was granted Orphan Drug designation as well as Fast Track Approval from the FDA for further study in these hard to treat conditions. Notably, phase 3 clinical trials of Epidiolex have demonstrated clinically significant improvement in Lennox-Gastaut syndrome and Dravet syndrome. On June 25th, 2018, Epidiolex was approved by the FDA to be the first CBD-based product available on the US market. (-)-Cannabidiol (-)-CBD (-)-trans-2-p-Mentha-1,8-dien-3-yl-5-pentylresorcinol (-)-trans-Cannabidiol Cannabidiolum Delta(1(2))-trans-Cannabidiol Δ(1(2))-trans-cannabidiol CBD Cannabidiol Epidiolex delta1(2)-trans-Cannabidiol Δ1(2)-trans-Cannabidiol C21H30O2 314.47 314.2246 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol cannabidiol 3556-78-3 CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Hydrocarbon derivatives Menthane monoterpenoids Monocyclic monoterpenoids Organooxygen compounds Resorcinols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Phenol Resorcinol organic molecular entity logp 6.10 ALOGPS logs -4.40 ALOGPS logp 6.33 ChemAxon pka_strongest_acidic 9.13 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1 ChemAxon inchikey QHMBSVQNZZTUGM-ZWKOTPCHSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 98.53 ChemAxon polarizability 38.26 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB09061 559095 644019 69478 Cannabidiol C00002641 CPD-7173 Laprairie RB, Bagher AM, Kelly ME, Denovan-Wright EM: Cannabidiol is a negative allosteric modulator of the cannabinoid CB1 receptor. Br J Pharmacol. 2015 Oct;172(20):4790-805. doi: 10.1111/bph.13250. Epub 2015 Oct 13. 26218440 Pertwee RG: The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. Br J Pharmacol. 2008 Jan;153(2):199-215. doi: 10.1038/sj.bjp.0707442. Epub 2007 Sep 10. 17828291 Sharma P, Murthy P, Bharath MM: Chemistry, metabolism, and toxicology of cannabis: clinical implications. Iran J Psychiatry. 2012 Fall;7(4):149-56. 23408483 Baron EP: Comprehensive Review of Medicinal Marijuana, Cannabinoids, and Therapeutic Implications in Medicine and Headache: What a Long Strange Trip It's Been .... Headache. 2015 Jun;55(6):885-916. doi: 10.1111/head.12570. Epub 2015 May 25. 26015168 Zou S, Kumar U: Cannabinoid Receptors and the Endocannabinoid System: Signaling and Function in the Central Nervous System. Int J Mol Sci. 2018 Mar 13;19(3). pii: ijms19030833. doi: 10.3390/ijms19030833. 29533978 Kaur R, Ambwani SR, Singh S: Endocannabinoid System: A Multi-Facet Therapeutic Target. Curr Clin Pharmacol. 2016;11(2):110-7. doi: 10.2174/1574884711666160418105339. 27086601 Elsohly MA, Slade D: Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci. 2005 Dec 22;78(5):539-48. doi: 10.1016/j.lfs.2005.09.011. Epub 2005 Sep 30. 16199061 Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. 26264914 Zhornitsky S, Potvin S: Cannabidiol in humans-the quest for therapeutic targets. Pharmaceuticals (Basel). 2012 May 21;5(5):529-52. doi: 10.3390/ph5050529. 24281562 Haresaku S, Hanioka T, Tsutsui A, Yamamoto M, Chou T, Gunjishima Y: Long-term effect of xylitol gum use on mutans streptococci in adults. Caries Res. 2007;41(3):198-203. doi: 10.1159/000099318. 17426399 Grillaud M, Bandon D, Nancy J, Delbos Y, Vaysse F: [The polyols in pediatric dentistry: advantages of xylitol]. Arch Pediatr. 2005 Jul;12(7):1180-6. doi: 10.1016/j.arcped.2005.01.032. 15964535 1.0 2020-03-19 00:35:20 UTC 2020-08-04 22:24:07 UTC CDB000012 Cannabidiol monomethylether Cannabidiol monomethyl ether (CBDM) is a methoxylated derivative of cannabidiol, which is a phytocannabinoid. Cannabidiol (CBD) is a resorcinol, which has a meta arrangement of its two hydroxyl groups on the benzene ring, one of which is methylated in cannabidiol monomethyl ether. Because of the mixed biosynthetic origins of CBD and CDBM they can also be considered as polyketides and monoterpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Cannabidiol monomethylether is a neutral compound. In one study using mice, rabbits and rats, cannabidol monomethylether was used as a substrate and caused hypothermia in some rodents (PMID: 1806944).  Unlike CBD, research regarding the pharmacological properties of CBDM is scarce. Cannabidiol monomethyl ether Cannabidiol-3-monomethyl ether, trans(+-)-isomer Cannabidiol-3-monomethyl ether C22H32O2 328.5 328.2402 3-methoxy-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylphenol 3-methoxy-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylphenol 1972-05-0 CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(OC)=C1 InChI=1S/C22H32O2/c1-6-7-8-9-17-13-20(23)22(21(14-17)24-5)19-12-16(4)10-11-18(19)15(2)3/h12-14,18-19,23H,2,6-11H2,1,3-5H3/t18-,19+/m0/s1 IPGGELGANIXRSX-RBUKOAKNSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Menthane monoterpenoids Methoxybenzenes Methoxyphenols Monocyclic monoterpenoids Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Phenol Phenol ether Phenoxy compound logp 6.42 ALOGPS logs -5.46 ALOGPS logp 6.47 ChemAxon pka_strongest_acidic 9.36 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 3-methoxy-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylphenol ChemAxon average_mass 328.5 ChemAxon mono_mass 328.2402 ChemAxon smiles CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(OC)=C1 ChemAxon formula C22H32O2 ChemAxon inchi InChI=1S/C22H32O2/c1-6-7-8-9-17-13-20(23)22(21(14-17)24-5)19-12-16(4)10-11-18(19)15(2)3/h12-14,18-19,23H,2,6-11H2,1,3-5H3/t18-,19+/m0/s1 ChemAxon inchikey IPGGELGANIXRSX-RBUKOAKNSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 103.01 ChemAxon polarizability 40.3 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 164905 Yamamoto I, Gohda H, Narimatsu S, Watanabe K, Yoshimura H: Cannabielsoin as a new metabolite of cannabidiol in mammals. Pharmacol Biochem Behav. 1991 Nov;40(3):541-6. doi: 10.1016/0091-3057(91)90360-e. 1806944 1.0 2020-03-19 00:35:22 UTC 2020-08-04 22:24:07 UTC CDB000013 Cannabidiol-C4 Cannabidiol-C4 is the butyl analogue of cannabidiol, which is one of the main phytocannabinoids found in Cannabis sativa (PMID: 6991645). Cannabidiol-C4 is a resorcinol, which has a meta arrangement of its two hydroxyl groups on the benzene ring. Because of the mixed biosynthetic origins of cannabidiol-C4, it can be considered as a polyketide and a monoterpenoid (DOI: 10.1016/B978-0-12-800756-3.00002-8). Cannabidiol-C4 is a neutral compound. Unlike CBD, research regarding the pharmacological properties of cannabidiol-C4 is scarce. C20H28O2 300.44 300.2089 5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol 5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol CCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 InChI=1S/C20H28O2/c1-5-6-7-15-11-18(21)20(19(22)12-15)17-10-14(4)8-9-16(17)13(2)3/h10-12,16-17,21-22H,2,5-9H2,1,3-4H3/t16-,17+/m0/s1 WBRXESQKGXYDOL-DLBZAZTESA-N logp 5.63 ALOGPS logs -4.23 ALOGPS logp 5.88 ChemAxon pka_strongest_acidic 9.13 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 5-butyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol ChemAxon average_mass 300.44 ChemAxon mono_mass 300.2089 ChemAxon smiles CCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 ChemAxon formula C20H28O2 ChemAxon inchi InChI=1S/C20H28O2/c1-5-6-7-15-11-18(21)20(19(22)12-15)17-10-14(4)8-9-16(17)13(2)3/h10-12,16-17,21-22H,2,5-9H2,1,3-4H3/t16-,17+/m0/s1 ChemAxon inchikey WBRXESQKGXYDOL-DLBZAZTESA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 93.93 ChemAxon polarizability 36.12 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444413 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. doi: 10.1016/j.toxicon.2006.06.017. Epub 2006 Jul 7. 16899266 Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. doi: 10.1007/s002530000431. 11152072 Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. 10543794 Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. 11728709 Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology. 1998 Apr;144 ( Pt 4):965-73. doi: 10.1099/00221287-144-4-965. 9579070 1.0 2020-03-19 00:35:25 UTC 2020-09-11 20:09:01 UTC CDB000014 Cannabidivarinic acid Cannabidivarinic acid or CBDVA, belongs to the class of cannabis compounds known as cannabidiols. It is a non-psychoactive cannabinoid found in cannabis plants. CBDVA is the structural C4 analogue of cannabidiolic acid (CBDA), the natural precursor of cannabidiol (CBD). As such, CBDVA can also be considered a hydroxybenzoic acid derivative. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and, at least, one hydroxyl group. The biosynthesis of CBDVA occurs through the cyclization of the isoprenoid side chain of cannabigerovarinic acid (CBGVA) to yield a cyclohexene moiety, common to all cannabidiol-type cannabinoids (https://doi.org/10.1016/B978-0-12-800756-3.00002-8). Unlike CBDA, research regarding the pharmacological properties of CBDVA is scarce. C20H26O4 330.42 330.1831 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-propylbenzoic acid 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-propylbenzoic acid CCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1C(O)=O InChI=1S/C20H26O4/c1-5-6-13-10-16(21)18(19(22)17(13)20(23)24)15-9-12(4)7-8-14(15)11(2)3/h9-10,14-15,21-22H,2,5-8H2,1,3-4H3,(H,23,24)/t14-,15+/m0/s1 CZXWOKHVLNYAHI-LSDHHAIUSA-N belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Hydroxybenzoic acid derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aromatic monoterpenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Menthane monoterpenoids Monocyclic monoterpenoids Organic oxides Organooxygen compounds Phenylpropanes Resorcinols Salicylic acids Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Dihydroxybenzoic acid Hydrocarbon derivative Hydroxybenzoic acid Monocyclic monoterpenoid Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Phenol Phenylpropane Resorcinol Salicylic acid Salicylic acid or derivatives Vinylogous acid logp 3.83 ALOGPS logs -3.72 ALOGPS logp 5.74 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-propylbenzoic acid ChemAxon average_mass 330.42 ChemAxon mono_mass 330.1831 ChemAxon smiles CCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1C(O)=O ChemAxon formula C20H26O4 ChemAxon inchi InChI=1S/C20H26O4/c1-5-6-13-10-16(21)18(19(22)17(13)20(23)24)15-9-12(4)7-8-14(15)11(2)3/h9-10,14-15,21-22H,2,5-8H2,1,3-4H3,(H,23,24)/t14-,15+/m0/s1 ChemAxon inchikey CZXWOKHVLNYAHI-LSDHHAIUSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 96.59 ChemAxon polarizability 36.98 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444387 1.0 2020-03-19 00:35:28 UTC 2020-09-11 20:09:01 UTC CDB000015 Cannabidivarin Cannabidivarin (CBDV) is a non-psychoactive cannabinoid found within medical Cannabis. It is one of over 100 cannabinoids identified from the Cannabis plants that can modulate the physiological activity of cannabis, or marijuana (PMID: 23408483). CBDV is the C3 analogue of cannabidiol (CBD). Notably, both cannabidiol and CBDV have demonstrated anticonvulsant activity in animal and human models with promising clinical trial results (PMID: 22970845; PMID: 25029033; PMID: 29290836; PMID: 29588939). Other cannabinoids with demonstrated anti-epileptic activity include Tetrahydrocannabivarin (THCV) and Œî9-tetrahydrocannabinolic acid. While the primary components of cannabis, CBD and THC, have been shown to modulate many of their physiological effects through their binding to the cannabinoid-1 (CB1) and cannabinoid-2 (CB2) receptors, the anticonvulsant cannabinoids do not interact with CB1 and CB2. The anti-epileptic activity of CBD and CBDV is thought to be modulated by their effects on transient receptor potential cation channel subfamily V member 1 (TRPV1), also known as the capsaicin receptor. TRPV1 is a member of a large family of ion channels that are involved in the onset and progression of several types of epilepsy. CBD and CBDV have been shown to dose-dependently activate and then desensitize TRPV1 as well as TRPV2 and transient receptor potential ankyrin 1 (TRPA1) channels (PMID 25029033; PMID: 29842819; PMID: 21175579). Desensitization of these ion channels is a potential mechanism by which these molecules cause a reduction of neuronal hyperexcitability that contributes to epileptic activity and seizures. CBDV has also been shown to inhibit the activity of diacylglycerol (DAG) lipase-Œ±, the primary enzyme responsible for the synthesis of the endocannabinoid, 2-arachidonoylglycerol (2-AG) (PMID: 24282673; PMID: 14610053). The clinical implications of this are unclear however, as this interaction has not been shown to affect CBDV's anticonvulsant activity. CBDV is being actively developed by GW Pharmaceuticals as the experimental compound GWP42006 as it has "shown the ability to treat seizures in pre-clinical models of epilepsy with significantly fewer side effects than currently approved anti-epileptic drugs". Unfortunately, as of February 2018, GW Pharmaceuticals announced that their Phase 2a placebo-controlled study of CBDV for focal seizure did not reach its primary endpoints. They will continue to study its use in epilepsy, however, and are expanding their investigations to include its potential use in Autism Spectrum Disorder, Rett syndrome and Fragile X among others. In October 2017 CBDV was given orphan designation by the European Medicines Agency for use in Rett Syndrome and again in February 2018 for treatment of Fragile X Syndrome. CBDV CBDV Compound C19H26O2 286.42 286.1933 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol 24274-48-4 CCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 InChI=1S/C19H26O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h9-11,15-16,20-21H,2,5-8H2,1,3-4H3/t15-,16+/m0/s1 REOZWEGFPHTFEI-JKSUJKDBSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Hydrocarbon derivatives Menthane monoterpenoids Monocyclic monoterpenoids Organooxygen compounds Phenylpropanes Resorcinols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Phenol Phenylpropane Resorcinol logp 5.13 ALOGPS logs -3.94 ALOGPS logp 5.44 ChemAxon pka_strongest_acidic 9.13 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol ChemAxon average_mass 286.42 ChemAxon mono_mass 286.1933 ChemAxon smiles CCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 ChemAxon formula C19H26O2 ChemAxon inchi InChI=1S/C19H26O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h9-11,15-16,20-21H,2,5-8H2,1,3-4H3/t15-,16+/m0/s1 ChemAxon inchikey REOZWEGFPHTFEI-JKSUJKDBSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 89.33 ChemAxon polarizability 34.05 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20217 11601669 DB14050 Cannabidivarin Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ: Cannabidivarin is anticonvulsant in mouse and rat. Br J Pharmacol. 2012 Dec;167(8):1629-42. doi: 10.1111/j.1476-5381.2012.02207.x. 22970845 Iannotti FA, Hill CL, Leo A, Alhusaini A, Soubrane C, Mazzarella E, Russo E, Whalley BJ, Di Marzo V, Stephens GJ: Nonpsychotropic plant cannabinoids, cannabidivarin (CBDV) and cannabidiol (CBD), activate and desensitize transient receptor potential vanilloid 1 (TRPV1) channels in vitro: potential for the treatment of neuronal hyperexcitability. ACS Chem Neurosci. 2014 Nov 19;5(11):1131-41. doi: 10.1021/cn5000524. Epub 2014 Jul 29. 25029033 Capasso A: Do Cannabinoids Confer Neuroprotection Against Epilepsy? An Overview. Open Neurol J. 2017 Dec 18;11:61-73. doi: 10.2174/1874205X01711010061. eCollection 2017. 29290836 Morano A, Cifelli P, Nencini P, Antonilli L, Fattouch J, Ruffolo G, Roseti C, Aronica E, Limatola C, Di Bonaventura C, Palma E, Giallonardo AT: Cannabis in epilepsy: From clinical practice to basic research focusing on the possible role of cannabidivarin. Epilepsia Open. 2016 Sep 19;1(3-4):145-151. doi: 10.1002/epi4.12015. eCollection 2016 Dec. 29588939 Ruzic Zecevic D, Folic M, Tantoush Z, Radovanovic M, Babic G, Jankovic SM: Investigational cannabinoids in seizure disorders, what have we learned thus far? Expert Opin Investig Drugs. 2018 Jun;27(6):535-541. doi: 10.1080/13543784.2018.1482275. Epub 2018 Jun 6. 29842819 De Petrocellis L, Ligresti A, Moriello AS, Allara M, Bisogno T, Petrosino S, Stott CG, Di Marzo V: Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. Br J Pharmacol. 2011 Aug;163(7):1479-94. doi: 10.1111/j.1476-5381.2010.01166.x. 21175579 Amada N, Yamasaki Y, Williams CM, Whalley BJ: Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression. PeerJ. 2013 Nov 21;1:e214. doi: 10.7717/peerj.214. eCollection 2013. 24282673 Bisogno T, Howell F, Williams G, Minassi A, Cascio MG, Ligresti A, Matias I, Schiano-Moriello A, Paul P, Williams EJ, Gangadharan U, Hobbs C, Di Marzo V, Doherty P: Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J Cell Biol. 2003 Nov 10;163(3):463-8. doi: 10.1083/jcb.200305129. 14610053 Sharma P, Murthy P, Bharath MM: Chemistry, metabolism, and toxicology of cannabis: clinical implications. Iran J Psychiatry. 2012 Fall;7(4):149-56. 23408483 1.0 2020-03-19 00:35:31 UTC 2020-08-04 22:28:18 UTC CDB000408 Cannabidiorcol Cannabidiorcol or Cannabidiol-C1 is the methyl analogue of cannabidiol, which is one of the main phytocannabinoids found in Cannabis sativa (PMID: 6991645). Cannabidiorcol is a resorcinol, which has a meta arrangement of its two hydroxyl groups on the benzene ring. Because of the mixed biosynthetic origins of cannabidiol-C4, it can be considered as a polyketide and a monoterpenoid (DOI: 10.1016/B978-0-12-800756-3.00002-8). Cannabidiol-C4 is a neutral compound. Unlike CBD, research regarding the pharmacological properties of cannabidiorcol is scarce. C17H22O2 258.36 258.162 5-methyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol 5-methyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol CC(=C)[C@@H]1CCC(C)=C[C@H]1C1=C(O)C=C(C)C=C1O InChI=1S/C17H22O2/c1-10(2)13-6-5-11(3)7-14(13)17-15(18)8-12(4)9-16(17)19/h7-9,13-14,18-19H,1,5-6H2,2-4H3/t13-,14+/m0/s1 GKVOVXWEBSQJPA-UONOGXRCSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Hydrocarbon derivatives Menthane monoterpenoids Meta cresols Monocyclic monoterpenoids Organooxygen compounds Resorcinols Toluenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Aromatic monoterpenoid Benzenoid Hydrocarbon derivative M-cresol Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Phenol Resorcinol Toluene logp 4.09 ALOGPS logs -3.45 ALOGPS logp 4.55 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -5.7 ChemAxon iupac 5-methyl-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]benzene-1,3-diol ChemAxon average_mass 258.36 ChemAxon mono_mass 258.162 ChemAxon smiles CC(=C)[C@@H]1CCC(C)=C[C@H]1C1=C(O)C=C(C)C=C1O ChemAxon formula C17H22O2 ChemAxon inchi InChI=1S/C17H22O2/c1-10(2)13-6-5-11(3)7-14(13)17-15(18)8-12(4)9-16(17)19/h7-9,13-14,18-19H,1,5-6H2,2-4H3/t13-,14+/m0/s1 ChemAxon inchikey GKVOVXWEBSQJPA-UONOGXRCSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 80.13 ChemAxon polarizability 29.87 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 16657068 8CB Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:35:33 UTC 2020-09-11 20:09:01 UTC CDB000016 Delta-9-tetrahydrocannabinolic acid A Delta-9-Tetrahydrocannabinolic acid A or THC acid A is classified as a delta-9-tetrahydrocannabinol, one of the major non-psychoactive cannabinoid compounds that are found only in the cannabis plant. THC acid A, and to a much lesser extent THC acid B, are biosynthetic precursors to delta-9-tetrahydrocannabinol (delta-9-THC), the principal psychoactive constituent of the cannabis plant. The difference between THC acid A and B is the position of the carboxyl functional group. In THC acid A, it is on the C-2 whereas in THC acid B, it is on the C-4 (PMID: 6991645). THC acid is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalyzed by an enzyme Geranyl-pyrophosphate‚Äîolivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THC acid. Over time, or when heated (via vaping or smoking), THC acid is decarboxylated, producing THC. While smoking a joint or baking cookies, THC acid A is partially converted into the psychoactive delta-9-THC via decarboxylation. Therefore, THC acid A is incorporated to a certain extent by cannabis consumers and is a promising candidate for use as an additional consumption marker (PMID: 22921834). While some studies showed that delta-9-THC acid binds cannabinoid type one (CB1) receptors with a Ki value of 23.5 nM (PMID: 25311884), others had found negligible activity (PMID: 18303850). Decarboxylation of THC acid A to THC during storage or under certain experimental conditions may contribute to these contrasting results. A recent study using freshly prepared and highly pure delta-9-THC acid (98%) showed that it yet had a low binding affinity for CB1 and CB2 receptors (PMID: 28861508), strongly suggesting that delta-9-THC acid biological activities are not mediated by interaction with these receptors. However, in another study, Delta-9-THC acid exhibited anti-emetic and immune-modulatory activities through CB1-dependent and CB1-in- dependent mechanisms, respectively (PMID: 16504929; PMID: 23889598). Delta-9-THC acid showed potent neuroprotective activity and may aid in the treatment of Huntington's disease and possibly other neurodegenerative and neuroinflammatory diseases (PMID: 28853159). 9-Carboxy-delta(9)-THC 9-Carboxy-THC 9-Carboxy-δ(9)-THC delta(9)-Tetrahydrocannabinolate Δ(9)-tetrahydrocannabinolate Δ(9)-tetrahydrocannabinolic acid THC-9-COOH THCA-a compound C22H30O4 358.48 358.2144 (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid 23978-85-0 CCCCCC1=C(C(O)=O)C(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16-/m1/s1 UCONUSSAWGCZMV-HZPDHXFCSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Salicylic acid and derivatives Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Salicylic acid or derivatives Vinylogous acid benzochromene diterpenoid hydroxy monocarboxylic acid phytocannabinoid polyketide logp 5.13 ALOGPS logs -4.48 ALOGPS logp 6.25 ChemAxon pka_strongest_acidic 2.89 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid ChemAxon average_mass 358.48 ChemAxon mono_mass 358.2144 ChemAxon smiles CCCCCC1=C(C(O)=O)C(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C22H30O4 ChemAxon inchi InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16-/m1/s1 ChemAxon inchikey UCONUSSAWGCZMV-HZPDHXFCSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 103.99 ChemAxon polarizability 41.91 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 67078 98523 CPD-7169 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Roth N, Wohlfarth A, Muller M, Auwarter V: Regioselective synthesis of isotopically labeled Delta9-tetrahydrocannabinolic acid A (THCA-A-D3) by reaction of Delta9-tetrahydrocannabinol-D3 with magnesium methyl carbonate. Forensic Sci Int. 2012 Oct 10;222(1-3):368-72. doi: 10.1016/j.forsciint.2012.07.019. Epub 2012 Aug 23. 22921834 Rosenthaler S, Pohn B, Kolmanz C, Huu CN, Krewenka C, Huber A, Kranner B, Rausch WD, Moldzio R: Differences in receptor binding affinity of several phytocannabinoids do not explain their effects on neural cell cultures. Neurotoxicol Teratol. 2014 Nov-Dec;46:49-56. doi: 10.1016/j.ntt.2014.09.003. Epub 2014 Oct 12. 25311884 Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, Matsumoto RR, Xu YT, Viard E, Speth RC, Karamyan VT, ElSohly MA: Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod. 2008 Apr;71(4):536-42. doi: 10.1021/np070454a. Epub 2008 Feb 28. 18303850 McPartland JM, MacDonald C, Young M, Grant PS, Furkert DP, Glass M: Affinity and Efficacy Studies of Tetrahydrocannabinolic Acid A at Cannabinoid Receptor Types One and Two. Cannabis Cannabinoid Res. 2017 May 1;2(1):87-95. doi: 10.1089/can.2016.0032. eCollection 2017. 28861508 Verhoeckx KC, Korthout HA, van Meeteren-Kreikamp AP, Ehlert KA, Wang M, van der Greef J, Rodenburg RJ, Witkamp RF: Unheated Cannabis sativa extracts and its major compound THC-acid have potential immuno-modulating properties not mediated by CB1 and CB2 receptor coupled pathways. Int Immunopharmacol. 2006 Apr;6(4):656-65. doi: 10.1016/j.intimp.2005.10.002. Epub 2005 Nov 7. 16504929 Rock EM, Kopstick RL, Limebeer CL, Parker LA: Tetrahydrocannabinolic acid reduces nausea-induced conditioned gaping in rats and vomiting in Suncus murinus. Br J Pharmacol. 2013 Oct;170(3):641-8. doi: 10.1111/bph.12316. 23889598 Nadal X, Del Rio C, Casano S, Palomares B, Ferreiro-Vera C, Navarrete C, Sanchez-Carnerero C, Cantarero I, Bellido ML, Meyer S, Morello G, Appendino G, Munoz E: Tetrahydrocannabinolic acid is a potent PPARgamma agonist with neuroprotective activity. Br J Pharmacol. 2017 Dec;174(23):4263-4276. doi: 10.1111/bph.14019. Epub 2017 Nov 2. 28853159 Hunter JE, Zhang J, Kris-Etherton PM: Cardiovascular disease risk of dietary stearic acid compared with trans, other saturated, and unsaturated fatty acids: a systematic review. Am J Clin Nutr. 2010 Jan;91(1):46-63. doi: 10.3945/ajcn.2009.27661. Epub 2009 Nov 25. 19939984 1.0 2020-03-19 00:35:37 UTC 2020-08-04 22:24:08 UTC CDB000017 Delta-9-tetrahydrocannabinolic acid B Delta-9-tetrahydrocannabinolic acid B or THC acid B, a delta 9-tetrahydrocannabinol, is one of the major non-psychoactive cannabinoid compounds that are found only in the cannabis plant. THC acid B, to a much lesser extent than THC acid A, is a biosynthetic precursor to delta-9-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant. The difference between THC acid A and B is the position of the carboxyl functional group. In THC acid A it is on the C-2 whereas in THC acid B it is on the C-4 (PMID: 6991645). THC acid is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalyzed by an enzyme Geranyl-pyrophosphate‚Äîolivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THC acid. Over time, or when heated (via vaping or smoking), THC acid is decarboxylated, producing THC. While some studies showed that delta-9-THC acid binds cannabinoid type one (CB1) receptors with a Ki value of 23.5 nM (PMID: 25311884), others had found a negligible activity (PMID: 18303850). Decarboxylation of THC acid A to THC during storage or under certain experimental conditions may contribute to these contrasting results A recent study showed that freshly prepared and highly pure delta-9-THC acid (98%) has a low binding affinity for CB1 and CB2 receptors (PMID: 28861508). Thus, it seems that the biological activities of delta-9-THC acid are not mediated by interaction with these classical membrane receptors. Delta-9-THC acid exhibited anti-emetic and immune-modulatory activities through CB1-dependent and CB1-in- dependent mechanisms respectively (PMID: 16504929; PMID: 23889598). Delta-9-THC acid shows potent neuroprotective activity, that may aid in the treatment of Huntington's disease and possibly other neurodegenerative and neuroinflammatory diseases (PMID: 28853159). (6AR,10as)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6ah,7H,8H,10ah-benzo[c]isochromene-4-carboxylate C22H30O4 358.48 358.2144 (6aR,10aS)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-4-carboxylic acid (6aR,10aS)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-4-carboxylic acid CCCCCC1=C(C(O)=O)C2=C([C@H]3C=C(C)CC[C@H]3C(C)(C)O2)C(O)=C1 InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17(23)19-15-11-13(2)9-10-16(15)22(3,4)26-20(19)18(14)21(24)25/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16+/m0/s1 VITZNDKHSIWPSR-JKSUJKDBSA-N logp 5.11 ALOGPS logs -4.55 ALOGPS logp 5.6 ChemAxon pka_strongest_acidic 3.83 ChemAxon pka_strongest_basic -5 ChemAxon iupac (6aR,10aS)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-4-carboxylic acid ChemAxon average_mass 358.48 ChemAxon mono_mass 358.2144 ChemAxon smiles CCCCCC1=C(C(O)=O)C2=C([C@H]3C=C(C)CC[C@H]3C(C)(C)O2)C(O)=C1 ChemAxon formula C22H30O4 ChemAxon inchi InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17(23)19-15-11-13(2)9-10-16(15)22(3,4)26-20(19)18(14)21(24)25/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16+/m0/s1 ChemAxon inchikey VITZNDKHSIWPSR-JKSUJKDBSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 103.99 ChemAxon polarizability 41.13 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rosenthaler S, Pohn B, Kolmanz C, Huu CN, Krewenka C, Huber A, Kranner B, Rausch WD, Moldzio R: Differences in receptor binding affinity of several phytocannabinoids do not explain their effects on neural cell cultures. Neurotoxicol Teratol. 2014 Nov-Dec;46:49-56. doi: 10.1016/j.ntt.2014.09.003. Epub 2014 Oct 12. 25311884 Ahmed SA, Ross SA, Slade D, Radwan MM, Zulfiqar F, Matsumoto RR, Xu YT, Viard E, Speth RC, Karamyan VT, ElSohly MA: Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod. 2008 Apr;71(4):536-42. doi: 10.1021/np070454a. Epub 2008 Feb 28. 18303850 McPartland JM, MacDonald C, Young M, Grant PS, Furkert DP, Glass M: Affinity and Efficacy Studies of Tetrahydrocannabinolic Acid A at Cannabinoid Receptor Types One and Two. Cannabis Cannabinoid Res. 2017 May 1;2(1):87-95. doi: 10.1089/can.2016.0032. eCollection 2017. 28861508 Verhoeckx KC, Korthout HA, van Meeteren-Kreikamp AP, Ehlert KA, Wang M, van der Greef J, Rodenburg RJ, Witkamp RF: Unheated Cannabis sativa extracts and its major compound THC-acid have potential immuno-modulating properties not mediated by CB1 and CB2 receptor coupled pathways. Int Immunopharmacol. 2006 Apr;6(4):656-65. doi: 10.1016/j.intimp.2005.10.002. Epub 2005 Nov 7. 16504929 Rock EM, Kopstick RL, Limebeer CL, Parker LA: Tetrahydrocannabinolic acid reduces nausea-induced conditioned gaping in rats and vomiting in Suncus murinus. Br J Pharmacol. 2013 Oct;170(3):641-8. doi: 10.1111/bph.12316. 23889598 Nadal X, Del Rio C, Casano S, Palomares B, Ferreiro-Vera C, Navarrete C, Sanchez-Carnerero C, Cantarero I, Bellido ML, Meyer S, Morello G, Appendino G, Munoz E: Tetrahydrocannabinolic acid is a potent PPARgamma agonist with neuroprotective activity. Br J Pharmacol. 2017 Dec;174(23):4263-4276. doi: 10.1111/bph.14019. Epub 2017 Nov 2. 28853159 1.0 2020-03-19 00:35:40 UTC 2020-09-11 20:09:01 UTC CDB000001 Delta-9-tetrahydrocannabinol Delta-9-Tetrahydrocannabinol, also known as tetrahydrocannabinol or THC, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. THC is also chemically or biochemically classified as a diterpenoid. Formally it can be described as a 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. Tetrahydrocannabinol (THC) is one of at least 113 cannabinoids identified in cannabis (PMID: 26836472). In the cannabis plant THC (like most plant terpenes) is used in self-defense, mostly to protect itself against insect predation, ultraviolet light, and other environmental stressors. THC is the principal psychoactive constituent of cannabis, responsible for the ‚Äúhigh‚Äù that users experience (https://doi.org/10.1021/ja01062a046). The psychoactivity of THC results from its partial agonist activity of the cannabinoid receptor CB1 (Ki = 10 nM), located mainly in the central nervous system, and the CB2 receptor (Ki = 24 nM), mainly found in cells of the immune system. THC activation of these cannabinoid receptors, especially the CB1 receptor, leads to a decrease in the concentration of the second messenger molecule cAMP in synaptosomes and brain synapses through inhibition of adenylate cyclase (PMID: 9260875; PMID: 1848340). In cannabis plants, THC occurs mainly as tetrahydrocannabinolic acid (THCA). THCA is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme Geranyl-pyrophosphate‚Äîolivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THCA. Over time, or when heated (via vaping or smoking), THCA is decarboxylated, producing THC. THC (either as a pure drug or through ingestion/inhalation via medical marijuana) is used for the treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatments. THC has been formulated into several commercially available oral drugs. Dronabinol is the generic name for the oral form of synthetic THC and is marketed in the U.S. as Marinol. It is indicated for the treatment of severe CINV (chemotherapy-induced nausea and vomiting) in cancer patients, and for AIDS-related anorexia associated with weight loss. Nabilone is the generic name for an orally administered synthetic structural analogue of THC, which is marketed in Canada as Cesamet but also now available in generic forms (e.g. RAN-nabilone, PMS-nabilone, TEVA-nabilone, CO- nabilone, ACT-nabilone). It is indicated for severe CINV in cancer patients. THC is an active ingredient in another drug called Nabiximols, a specific extract of Cannabis that was approved as a botanical drug in the United Kingdom in 2010 as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain, spasticity, overactive bladder, and other symptoms. (-)-delta9-trans-Tetrahydrocannabinol 1-trans-delta-9-Tetrahydrocannabinol 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-ol 6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol Delta(1)-Tetrahydrocannabinol delta9-Tetrahydrocannabinol Delta(9)-THC Dronabinol Dronabinolum Syndros THC Marinol (-)-Δ9-trans-tetrahydrocannabinol 1-trans-Δ-9-tetrahydrocannabinol Δ(1)-tetrahydrocannabinol Δ9-tetrahydrocannabinol Δ(9)-THC DELTA-9-THC DELTA-9-TETRAHYDROCANNABINOL Δ-9-THC Δ-9-tetrahydrocannabinol Tetrahydrocannabinol, (6a-trans)-isomer 9-Ene-tetrahydrocannabinol Tetrahydrocannabinol, (6ar-cis)-isomer Tetrahydrocannabinol, (6as-cis)-isomer Tetrahydrocannabinol, trans isomer delta(9)-Tetrahydrocannabinol delta(1)-THC 9 Ene tetrahydrocannabinol Solvay brand OF tetrahydrocannabinol Tetrahydrocannabinol, trans-(+-)-isomer Tetrahydrocannabinol, trans-isomer delta 1-Tetrahydrocannabinol (-)- delta 9-Tetrahydrocannabinol (-)-delta 1-Tetrahydrocannabinol (-)-delta 9-THC (-)-delta 9-trans-Tetrahydrocannabinol (-)-trans-delta 1-Tetrahydrocannabinol (-)-trans-delta 9-Tetrahydrocannabinol (-)-trans-delta 9-THC (L)-delta 1-Tetrahydrocannabinol 1-trans-delta 9-Tetrahydrocannabinol 14C-delta 1-Tetrahydrocannabinol delta 1-THC delta 9-Tetrahydrocannabinol delta 9-THC delta 9-trans-Tetrahydrocannabinol Exocyclic delta (9)(11)-tetrahydrocannabiol L-delta 1-trans-Tetrahydrocannabinol L-trans-delta 9-Tetrahydrocannabinol Primolut trans-delta (-)-9-Tetrahydrocannabinol trans-delta 9-Tetrahydrocannabinol Tetrahydrocannabinol (-)-3,4-trans-delta1-Tetrahydrocannabinol (-)-3,4-trans-Δ1-Tetrahydrocannabinol (-)-delta1-Tetrahydrocannabinol (-)-delta9-THC (-)-delta9-Tetrahydrocannabinol (-)-trans-delta1-Tetrahydrocannabinol (-)-trans-delta9-THC (-)-trans-delta9-Tetrahydrocannabinol (-)-trans-Δ1-Tetrahydrocannabinol (-)-trans-Δ9-THC (-)-trans-Δ9-Tetrahydrocannabinol (-)-Δ1-Tetrahydrocannabinol (-)-Δ9-THC (-)-Δ9-Tetrahydrocannabinol (l)-delta1-Tetrahydrocannabinol (l)-Δ1-Tetrahydrocannabinol delta1-THC delta1-Tetrahydrocannabinol delta9-THC delta9-trans-Tetrahydrocannabinol l-delta1-trans-Tetrahydrocannabinol l-trans-delta9-Tetrahydrocannabinol l-trans-Δ9-Tetrahydrocannabinol l-Δ1-trans-Tetrahydrocannabinol trans-(-)-delta9-Tetrahydrocannabinol trans-(-)-Δ9-Tetrahydrocannabinol trans-delta9-Tetrahydrocannabinol trans-Δ9-Tetrahydrocannabinol Δ1-THC Δ1-Tetrahydrocannabinol Δ9-THC Δ9-trans-Tetrahydrocannabinol C21H30O2 314.46 314.2246 (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol THC 1972-08-3 CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1 CYQFCXCEBYINGO-IAGOWNOFSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Cannabinoids benzochromene diterpenoid phytocannabinoid polyketide water_solubility 2.63e-03 g/L logp 5.648 melting_point 200 °C logp 7.29 ALOGPS logs -5.08 ALOGPS logp 5.94 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 314.46 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1 ChemAxon inchikey CYQFCXCEBYINGO-IAGOWNOFSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 96.73 ChemAxon polarizability 38.96 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB00470 15266 16078 C06972 66964 FDB031310 C00002675 Tetrahydrocannabinol CPD-7172 Aizpurua-Olaizola O, Soydaner U, Ozturk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A: Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. J Nat Prod. 2016 Feb 26;79(2):324-31. doi: 10.1021/acs.jnatprod.5b00949. Epub 2016 Feb 2. 26836472 Koh WS, Crawford RB, Kaminski NE: Inhibition of protein kinase A and cyclic AMP response element (CRE)-specific transcription factor binding by delta9-tetrahydrocannabinol (delta9-THC): a putative mechanism of cannabinoid-induced immune modulation. Biochem Pharmacol. 1997 May 15;53(10):1477-84. doi: 10.1016/s0006-2952(97)82441-0. 9260875 Little PJ, Martin BR: The effects of delta 9-tetrahydrocannabinol and other cannabinoids on cAMP accumulation in synaptosomes. Life Sci. 1991;48(12):1133-41. doi: 10.1016/0024-3205(91)90450-p. 1848340 1.0 2020-03-19 00:35:42 UTC 2020-07-24 23:30:07 UTC CDB000019 Delta-9-tetrahydrocannabinol-C4 Delta-9-Tetrahydrocannabinol-C4, also known as THC-C4, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. Delta-9-Tetrahydrocannabinol-C4, first identified from cannabis, were characterized by gas chromatography-mass spectrometry (GC-MS) of the ethyl acetate extract of ten police confiscated cannabis resins, tinctures and leaves in 1976 (PMID: 6715). It is one of more than 120 cannabinoid compounds identified in cannabis plant. It belongs to the delta-9-tetrahydrocannabinol class of cannabinoid compounds in the cannabis plant that has C4H9 substituent positioning on C-3 (PMID: 6991645). Butyl-delta(9)-tetrahydrocannabinol Butyl-delta(9)-THC C20H28O2 300.44 300.2089 (6aR,10aR)-3-butyl-6,6,9-trimethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol (6aR,10aR)-3-butyl-6,6,9-trimethyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol 60008-00-6 CCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1 QHCQSGYWGBDSIY-HZPDHXFCSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 6.69 ALOGPS logs -4.74 ALOGPS logp 5.5 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-3-butyl-6,6,9-trimethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 300.44 ChemAxon mono_mass 300.2089 ChemAxon smiles CCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C20H28O2 ChemAxon inchi InChI=1S/C20H28O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h10-12,15-16,21H,5-9H2,1-4H3/t15-,16-/m1/s1 ChemAxon inchikey QHCQSGYWGBDSIY-HZPDHXFCSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 92.13 ChemAxon polarizability 36.71 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6453891 Harvey DJ: Characterization of the butyl homologues of delta1-tetrahydrocannabinol, cannabinol and cannabidiol in samples of cannabis by combined gas chromatography and mass spectrometry. J Pharm Pharmacol. 1976 Apr;28(4):280-5. doi: 10.1111/j.2042-7158.1976.tb04153.x. 6715 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:35:46 UTC 2020-07-24 23:30:15 UTC CDB000020 Delta-9-tetrahydrocannabivarinic acid Delta-9-tetrahydrocannabivarinic acid, also known as, THCVA, belongs to the delta-9-tetrahydrocannabinol class of cannabinoid compounds in cannabis plant. Delta-9-tetrahydrocannabivarinic acid is one of more than 120 cannabinoid compounds that have been identified in the cannabis plant. Mass spectral evidence of THCVA presence in cannabis was reported in 1973 based on the evaluation of 51 samples from different geographical locations (PMID: 4752132). Its structure is like delta-9-THCV except for the carboxyl functional group positioning on C-2 in delta-9-THCVA. (PMID: 6991645). The proposed biosynthesis of THCVA was as following: divarinolic acid is formed by the condensation of three molecules of malonyl-CoA and one molecule of n-Butyl-CoA, which yields cannabigerovarinic acid (CBGVA) through geranyl diphosphate (GPP) synthase and is converted into THCVA (DOI: 10.1007/s11101-008-9094-4, DOI: 10.1016/S0031-9422(00)84939-0). C20H26O4 330.42 330.1831 (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-propyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-propyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid 39986-26-0 CCCC1=C(C(O)=O)C(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C20H26O4/c1-5-6-12-10-15-17(18(21)16(12)19(22)23)13-9-11(2)7-8-14(13)20(3,4)24-15/h9-10,13-14,21H,5-8H2,1-4H3,(H,22,23)/t13-,14-/m1/s1 IQSYWEWTWDEVNO-ZIAGYGMSSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Salicylic acid and derivatives Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Hydroxybenzoic acid Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Phenol Salicylic acid or derivatives Vinylogous acid logp 4.34 ALOGPS logs -4.02 ALOGPS logp 5.36 ChemAxon pka_strongest_acidic 2.89 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-propyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid ChemAxon average_mass 330.42 ChemAxon mono_mass 330.1831 ChemAxon smiles CCCC1=C(C(O)=O)C(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C20H26O4 ChemAxon inchi InChI=1S/C20H26O4/c1-5-6-12-10-15-17(18(21)16(12)19(22)23)13-9-11(2)7-8-14(13)20(3,4)24-15/h9-10,13-14,21H,5-8H2,1-4H3,(H,22,23)/t13-,14-/m1/s1 ChemAxon inchikey IQSYWEWTWDEVNO-ZIAGYGMSSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 94.79 ChemAxon polarizability 37.6 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444416 Turner CE, Hadley K, Fetterman PS: Constituents of Cannabis sativa L. VI. Propyl homologs in samples of known geographical origin. J Pharm Sci. 1973 Oct;62(10):1739-41. doi: 10.1002/jps.2600621045. 4752132 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:35:48 UTC 2020-09-11 20:09:01 UTC CDB000021 Delta-9-tetrhydrocannabivarin Delta-9-Tetrahydrocannabivarin belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Tetrahydrocannabivarin is a neutral compound. Delta-9-Tetrahydrocannabivarin (THCV, THV) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of a pentyl (5-carbon) group on the molecule, which makes it produce very different effects from THC. Delta-9-Tetrahydrocannabivarin is one of the Delta-9-THC type cannabinoid compounds that are known in cannabis plant. Some cannabis compounds are used as medicine. Delta-9-Tetrahydrocannabivarin's main pharmacological characteristics are as an analgesic and an euphoriant. (PMID: 6991645). It is a cannabis receptor type-1(CB1) and cannabis receptor type-2(CB2) antagonist (PMID: 16205722) and a CB2 agonist at higher doses, which attenuate inflammation and hyperalgesia in mice (PMID: 20590571). C19H26O2 286.42 286.1933 (6aR,10aR)-6,6,9-trimethyl-3-propyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol tetrahydrocannabivarin 31262-37-0 CCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1 ZROLHBHDLIHEMS-HUUCEWRRSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle logp 6.08 ALOGPS logs -4.51 ALOGPS logp 5.06 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-6,6,9-trimethyl-3-propyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 286.42 ChemAxon mono_mass 286.1933 ChemAxon smiles CCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C19H26O2 ChemAxon inchi InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1 ChemAxon inchikey ZROLHBHDLIHEMS-HUUCEWRRSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 87.53 ChemAxon polarizability 34.52 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB11755 93147 Tetrahydrocannabivarin Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Thomas A, Stevenson LA, Wease KN, Price MR, Baillie G, Ross RA, Pertwee RG: Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist. Br J Pharmacol. 2005 Dec;146(7):917-26. doi: 10.1038/sj.bjp.0706414. 16205722 Bolognini D, Costa B, Maione S, Comelli F, Marini P, Di Marzo V, Parolaro D, Ross RA, Gauson LA, Cascio MG, Pertwee RG: The plant cannabinoid Delta9-tetrahydrocannabivarin can decrease signs of inflammation and inflammatory pain in mice. Br J Pharmacol. 2010 Jun;160(3):677-87. doi: 10.1111/j.1476-5381.2010.00756.x. 20590571 1.0 2020-03-19 00:35:51 UTC 2020-06-19 18:40:59 UTC CDB000415 Delta-9-tetrahydrocannabiorcolic acid Delta-9-Tetrahydrocannabiorcolic acid, also known as THCA-C1, belongs to the organic compounds known as 2,2-dimethyl-1-benzopyrans. Delta-9-Tetrahydrocannabiorcolic acid is one of more than 120 cannabinoid compounds that are known in the cannabis plant. Delta-9-tetrahydrocannabiorcolic acid belongs to the Delta-9-tetrahydrocannabinol class of cannabinoid compounds in cannabis compound classification. (PMID: 6991645). It belongs to the delta-9-tetrahydrocannabinolic acid class of cannabinoid compounds in the cannabis plant that has CH3 substituent positioning on C-3, a lighter-chain phytocannabinoid than delta-9-tetrahydrocannabinolic acid. (6AS,10ar)-1-hydroxy-3,6,6,9-tetramethyl-6H,6ah,7H,8H,10ah-benzo[c]isochromene-2-carboxylate C18H22O4 302.37 302.1518 (6aS,10aR)-1-hydroxy-3,6,6,9-tetramethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid (6aS,10aR)-1-hydroxy-3,6,6,9-tetramethyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid CC1=C[C@@H]2[C@H](CC1)C(C)(C)OC1=CC(C)=C(C(O)=O)C(O)=C21 InChI=1S/C18H22O4/c1-9-5-6-12-11(7-9)15-13(22-18(12,3)4)8-10(2)14(16(15)19)17(20)21/h7-8,11-12,19H,5-6H2,1-4H3,(H,20,21)/t11-,12+/m1/s1 BWFHYGJGKLAXKO-NEPJUHHUSA-N logp 3.66 ALOGPS logs -3.55 ALOGPS logp 4.47 ChemAxon pka_strongest_acidic 2.93 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aS,10aR)-1-hydroxy-3,6,6,9-tetramethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylic acid ChemAxon average_mass 302.37 ChemAxon mono_mass 302.1518 ChemAxon smiles CC1=C[C@@H]2[C@H](CC1)C(C)(C)OC1=CC(C)=C(C(O)=O)C(O)=C21 ChemAxon formula C18H22O4 ChemAxon inchi InChI=1S/C18H22O4/c1-9-5-6-12-11(7-9)15-13(22-18(12,3)4)8-10(2)14(16(15)19)17(20)21/h7-8,11-12,19H,5-6H2,1-4H3,(H,20,21)/t11-,12+/m1/s1 ChemAxon inchikey BWFHYGJGKLAXKO-NEPJUHHUSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 85.59 ChemAxon polarizability 32.84 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:35:54 UTC 2020-07-24 23:30:15 UTC CDB000416 Delta-9-tetrahydrocannabiorcol Delta-9-Tetrahydrocannabiorcol, also known as THC-C1, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Delta-9-Tetrahydrocannabiorcol is a neutral compound . Delta-9-Tetrahydrocannabiorcol is one of more than 120 cannabinoid compounds that are known in cannabis plant (PMID: 6991645). It belongs to the delta-9-tetrahydrocannabinol class of cannabinoid compounds in the cannabis plant that has CH3 substituent positioning on C-3 (PMID: 6991645). A study has shown that delta-9-tetrahydrocannabiorcol acid binds cannabinoid type one (CB1) and type 2 (CB2) receptors and displayed the highest activity on transient receptor potential ankyrin 1 (TRPA1), a unique sensor of noxious stimuli and a potential drug target for analgesics, without affecting the cannabinoid receptors (PMID: 22109525). C17H22O2 258.36 258.162 (6aR,10aR)-3,6,6,9-tetramethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol (6aR,10aR)-3,6,6,9-tetramethyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol 22972-65-2 CC1=C[C@@H]2[C@@H](CC1)C(C)(C)OC1=CC(C)=CC(O)=C21 InChI=1S/C17H22O2/c1-10-5-6-13-12(7-10)16-14(18)8-11(2)9-15(16)19-17(13,3)4/h7-9,12-13,18H,5-6H2,1-4H3/t12-,13-/m1/s1 WIDIPARNVYRVNW-CHWSQXEVSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 4.87 ALOGPS logs -4.36 ALOGPS logp 4.17 ChemAxon pka_strongest_acidic 9.37 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-3,6,6,9-tetramethyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 258.36 ChemAxon mono_mass 258.162 ChemAxon smiles CC1=C[C@@H]2[C@@H](CC1)C(C)(C)OC1=CC(C)=CC(O)=C21 ChemAxon formula C17H22O2 ChemAxon inchi InChI=1S/C17H22O2/c1-10-5-6-13-12(7-10)16-14(18)8-11(2)9-15(16)19-17(13,3)4/h7-9,12-13,18H,5-6H2,1-4H3/t12-,13-/m1/s1 ChemAxon inchikey WIDIPARNVYRVNW-CHWSQXEVSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 78.33 ChemAxon polarizability 30.41 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 22805649 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Andersson DA, Gentry C, Alenmyr L, Killander D, Lewis SE, Andersson A, Bucher B, Galzi JL, Sterner O, Bevan S, Hogestatt ED, Zygmunt PM: TRPA1 mediates spinal antinociception induced by acetaminophen and the cannabinoid Delta(9)-tetrahydrocannabiorcol. Nat Commun. 2011 Nov 22;2:551. doi: 10.1038/ncomms1559. 22109525 1.0 2020-03-19 00:35:57 UTC 2020-08-04 22:24:08 UTC CDB000022 Delta-7-cis-iso-tetrahydrocannabivarin Delta-7-cis-iso-Tetrahydrocannabivarin belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Delta-7-Cis-iso-Tetrahydrocannabivarin is a neutral compound . Delta-7-cis-iso-tetrahydrocannabivarin is one of more than 120 cannabinoid compounds that are known in cannabis plant (PMID: 6991645). It was first isolated from Thai cannabis in 1981 (DOI: 10.1248/cpb.29.3720) and is one of the 18 miscellaneous-type cannabinoids (DOI: 10.1093/acprof:oso/9780199662685.003.0001). C19H26O2 286.42 286.1933 (1R,9R,12R)-9-methyl-12-(prop-1-en-2-yl)-5-propyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol (1R,9R,12R)-9-methyl-12-(prop-1-en-2-yl)-5-propyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol CCCC1=CC(O)=C2[C@@H]3C[C@@](C)(CC[C@H]3C(C)=C)OC2=C1 InChI=1S/C19H26O2/c1-5-6-13-9-16(20)18-15-11-19(4,21-17(18)10-13)8-7-14(15)12(2)3/h9-10,14-15,20H,2,5-8,11H2,1,3-4H3/t14-,15+,19+/m0/s1 SBPMGFIOIRMBJJ-QMTMVMCOSA-N belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 5.72 ALOGPS logs -5.25 ALOGPS logp 5.11 ChemAxon pka_strongest_acidic 10.03 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (1R,9R,12R)-9-methyl-12-(prop-1-en-2-yl)-5-propyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2,4,6-trien-3-ol ChemAxon average_mass 286.42 ChemAxon mono_mass 286.1933 ChemAxon smiles CCCC1=CC(O)=C2[C@@H]3C[C@@](C)(CC[C@H]3C(C)=C)OC2=C1 ChemAxon formula C19H26O2 ChemAxon inchi InChI=1S/C19H26O2/c1-5-6-13-9-16(20)18-15-11-19(4,21-17(18)10-13)8-7-14(15)12(2)3/h9-10,14-15,20H,2,5-8,11H2,1,3-4H3/t14-,15+,19+/m0/s1 ChemAxon inchikey SBPMGFIOIRMBJJ-QMTMVMCOSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 86.46 ChemAxon polarizability 34.04 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444409 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Svensson GP, Gunduz EA, Sjoberg N, Hedenstrom E, Lassance JM, Wang HL, Lofstedt C, Anderbrant O: Identification, synthesis, and behavioral activity of 5,11-dimethylpentacosane, a novel sex pheromone component of the greater wax moth, Galleria mellonella (L.). J Chem Ecol. 2014 Apr;40(4):387-95. doi: 10.1007/s10886-014-0410-8. Epub 2014 Apr 2. 24692052 1.0 2020-03-19 00:36:00 UTC 2020-08-04 22:24:08 UTC CDB000023 Detla-8-tetrahydrocannabinolic acid Delta-8-tetrahydrocannabinolic acid, also known as Delta-8-THCA, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. Detla-8-tetrahydrocannabinolic acid is one of more than 120 cannabinoid compounds that are known in cannabis plant. It is one of the only two delta-8-THC-type cannabinoids in cannabis, namely delta-8-THC and delta-8-THCA. Delta-8-THC and its acid precursor are considered as THC and THC acid artifacts, respectively. The 8,9 double-bond position is thermodynamically more stable than the 9,10 position. Delta-8-THC is approximately 20% less active than THC (PMID: 6991645). THC acid is produced via the following pathway: Geranyl pyrophosphate and olivetolic acid react, catalyzed by an enzyme Geranyl-pyrophosphate‚Äîolivetolic acid geranyltransferase to produce cannabigerolic acid which is then cyclized by the enzyme THC acid synthase to give THC acid. C22H30O4 358.48 358.2144 (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromene-2-carboxylic acid (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,10H,10aH-benzo[c]isochromene-2-carboxylic acid 23978-89-4 CCCCCC1=CC2=C([C@@H]3CC(C)=CC[C@H]3C(C)(C)O2)C(O)=C1C(O)=O InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9,12,15-16,23H,5-8,10-11H2,1-4H3,(H,24,25)/t15-,16-/m1/s1 YKKHSYLGQXKVMO-HZPDHXFCSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Salicylic acid and derivatives Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Hydroxybenzoic acid Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Phenol Salicylic acid or derivatives Vinylogous acid logp 5.42 ALOGPS logs -4.46 ALOGPS logp 6.25 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromene-2-carboxylic acid ChemAxon average_mass 358.48 ChemAxon mono_mass 358.2144 ChemAxon smiles CCCCCC1=CC2=C([C@@H]3CC(C)=CC[C@H]3C(C)(C)O2)C(O)=C1C(O)=O ChemAxon formula C22H30O4 ChemAxon inchi InChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9,12,15-16,23H,5-8,10-11H2,1-4H3,(H,24,25)/t15-,16-/m1/s1 ChemAxon inchikey YKKHSYLGQXKVMO-HZPDHXFCSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 103.99 ChemAxon polarizability 41.87 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444391 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:02 UTC 2020-07-22 22:11:10 UTC CDB000024 Delta-8-tetrahydrocannabinol Delta-8-tetrahydrocannabinol, also known as delta-8-THC, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Delta-8-THC and its acid precursor are considered as THC and THC acid artifacts, respectively. The 8,9 double-bond position is thermodynamically more stable than the 9,10 position. Delta-8-THC is a neutral compound and it is one of more than 120 cannabinoid compounds that are known in cannabis plant. Delta-8-tetrahydrocannabinol is a minor constituent of most varieties of marijuana in which its double-bond isomer, delta-9-THC, predominates. (PMID: 6991645). It is a partial agonist for cannabinoid type one (CB1) / type 2 (CB2) receptors and the activation of CB1/CB2 inhibits adenylyl cyclase, activates potassium channels, or reduces calcium channel conductance (PMID: 20166921; DOI: 10.1016/bs.ant.2018.10.006). It has also been shown to be pharmacologically active as an antiglaucoma agent (PMID: 12182967; PMID: 1328979). Delta-8-THC is easier and less expensive to prepare and is less psychotropic than delta-9-THC (PMID: 1328979; PMID: 15099912; PMID: 15025853; PMID: 15067692). Additionally, delta-8-THC is chemically more stable, does not undergo oxidation to cannabinol and has a much longer shelf life than delta-9-THC (PMID: 1328979). Moreover, it has been shown to exhibit negligible side effects when administered prior to antineoplastic therapy in cancer patients (PMID: 15067692). C21H30O2 314.47 314.2246 (6aR,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol (6aR,10aS)-6,6,9-trimethyl-3-pentyl-6aH,7H,10H,10aH-benzo[c]isochromen-1-ol CCCCCC1=CC(O)=C2[C@H]3CC(C)=CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9,12-13,16-17,22H,5-8,10-11H2,1-4H3/t16-,17+/m0/s1 HCAWPGARWVBULJ-DLBZAZTESA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 7.65 ALOGPS logs -5.10 ALOGPS logp 5.94 ChemAxon pka_strongest_acidic 10.03 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aR,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C2[C@H]3CC(C)=CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9,12-13,16-17,22H,5-8,10-11H2,1-4H3/t16-,17+/m0/s1 ChemAxon inchikey HCAWPGARWVBULJ-DLBZAZTESA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 96.73 ChemAxon polarizability 38.53 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 86308458 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Reggio PH: Endocannabinoid binding to the cannabinoid receptors: what is known and what remains unknown. Curr Med Chem. 2010;17(14):1468-86. doi: 10.2174/092986710790980005. 20166921 Jarvinen T, Pate DW, Laine K: Cannabinoids in the treatment of glaucoma. Pharmacol Ther. 2002 Aug;95(2):203-20. doi: 10.1016/s0163-7258(02)00259-0. 12182967 Muchtar S, Almog S, Torracca MT, Saettone MF, Benita S: A submicron emulsion as ocular vehicle for delta-8-tetrahydrocannabinol: effect on intraocular pressure in rabbits. Ophthalmic Res. 1992;24(3):142-9. doi: 10.1159/000267160. 1328979 Avraham Y, Ben-Shushan D, Breuer A, Zolotarev O, Okon A, Fink N, Katz V, Berry EM: Very low doses of delta 8-THC increase food consumption and alter neurotransmitter levels following weight loss. Pharmacol Biochem Behav. 2004 Apr;77(4):675-84. doi: 10.1016/j.pbb.2004.01.015. 15099912 Stinchcomb AL, Valiveti S, Hammell DC, Ramsey DR: Human skin permeation of Delta8-tetrahydrocannabinol, cannabidiol and cannabinol. J Pharm Pharmacol. 2004 Mar;56(3):291-7. doi: 10.1211/0022357022791. 15025853 Valiveti S, Hammell DC, Earles DC, Stinchcomb AL: In vitro/in vivo correlation studies for transdermal delta 8-THC development. J Pharm Sci. 2004 May;93(5):1154-64. doi: 10.1002/jps.20036. 15067692 1.0 2020-03-19 00:36:05 UTC 2020-07-22 22:11:10 UTC CDB000025 Cannabicyclolic acid Cannabicyclolic acid, also known as cannabicyclolate or CBLA, belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Cannabicyclolic acid is a neutral compound . Cannabicyclolic acid or CBLA, has also been placed in the class of cannabis compounds known as Cannabicyclols. Cannabicyclolic acid (CBLA) is a non-psychoactive cannabinoid found in cannabis plants (PMID: 6991645). CBLA is a relatively rare or low-abundance compound in cannabis. It is thought to be a photo-oxidation or natural degradation product of cannabichromenic acid (CBCA). CBLA is not considered to be an original cannabinoid (PMID: 6991645). (1AR)-1a,2,3,3a,8bbeta,8cbeta-hexahydro-1,1,3abeta-trimethyl-6-pentyl-8-hydroxy-1H-4-oxa-benzo[F]cyclobuta[CD]indene-7-carboxylate C22H30O4 358.48 358.2144 (1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid (1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid CCCCCC1=CC2=C([C@H]3[C@@H]4[C@@H](CC[C@]4(C)O2)C3(C)C)C(O)=C1C(O)=O InChI=1S/C22H30O4/c1-5-6-7-8-12-11-14-16(19(23)15(12)20(24)25)18-17-13(21(18,2)3)9-10-22(17,4)26-14/h11,13,17-18,23H,5-10H2,1-4H3,(H,24,25)/t13-,17+,18+,22+/m1/s1 JVOHLEIRDMVLHS-NDONDOTQSA-N belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Salicylic acid and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Vinylogous acids 1-benzopyran 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzopyran Carboxylic acid Carboxylic acid derivative Chromane Ether Hydrocarbon derivative Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Salicylic acid or derivatives Vinylogous acid logp 5.22 ALOGPS logs -4.60 ALOGPS logp 5.97 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid ChemAxon average_mass 358.48 ChemAxon mono_mass 358.2144 ChemAxon smiles CCCCCC1=CC2=C([C@H]3[C@@H]4[C@@H](CC[C@]4(C)O2)C3(C)C)C(O)=C1C(O)=O ChemAxon formula C22H30O4 ChemAxon inchi InChI=1S/C22H30O4/c1-5-6-7-8-12-11-14-16(19(23)15(12)20(24)25)18-17-13(21(18,2)3)9-10-22(17,4)26-14/h11,13,17-18,23H,5-10H2,1-4H3,(H,24,25)/t13-,17+,18+,22+/m1/s1 ChemAxon inchikey JVOHLEIRDMVLHS-NDONDOTQSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 101.08 ChemAxon polarizability 40.95 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 101769204 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:08 UTC 2020-09-11 20:09:01 UTC CDB000026 Cannabicyclol Cannabicyclol (CBL) belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. Cannabicyclol is a neutral compound . It is a non-psychoactive oxidation product of cannabichromene, produced mainly during long term storage of cannabis (PMID: 31202146). CBL has been proposed as a good candidate for a chemical marker to identify cannabis samples from different storage conditions (PMID: 31202146). C21H30O2 314.47 314.2246 (1R,9R,12S,14R)-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol (1R,9R,12S,14R)-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol 21366-63-2 CCCCCC1=CC(O)=C2[C@@H]3[C@H]4[C@H](CC[C@@]4(C)OC2=C1)C3(C)C InChI=1S/C21H30O2/c1-5-6-7-8-13-11-15(22)17-16(12-13)23-21(4)10-9-14-18(21)19(17)20(14,2)3/h11-12,14,18-19,22H,5-10H2,1-4H3/t14-,18+,19+,21+/m0/s1 IGHTZQUIFGUJTG-QSMXQIJUSA-N belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 5.64 ALOGPS logs -6.01 ALOGPS logp 5.66 ChemAxon pka_strongest_acidic 10.02 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (1R,9R,12S,14R)-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C2[C@@H]3[C@H]4[C@H](CC[C@@]4(C)OC2=C1)C3(C)C ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-13-11-15(22)17-16(12-13)23-21(4)10-9-14-18(21)19(17)20(14,2)3/h11-12,14,18-19,22H,5-10H2,1-4H3/t14-,18+,19+,21+/m0/s1 ChemAxon inchikey IGHTZQUIFGUJTG-QSMXQIJUSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 93.83 ChemAxon polarizability 38.07 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444380 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Grafstrom K, Andersson K, Pettersson N, Dalgaard J, Dunne SJ: Effects of long term storage on secondary metabolite profiles of cannabis resin. Forensic Sci Int. 2019 Aug;301:331-340. doi: 10.1016/j.forsciint.2019.05.035. Epub 2019 May 25. 31202146 1.0 2020-03-19 00:36:11 UTC 2020-07-07 15:58:17 UTC CDB000422 Cannabicyclovarin Cannabicyclovarin (CBLV) belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that include a 1-benzopyran moiety, a bicyclic compound made up of a benzene ring fused to a pyran ring, so that the oxygen atom is at the 1-position. Cannabicyclol is a neutral compound . It is a non-psychoactive cannabinoid and the C-3 analogue of Cannabicyclol (CBL). It appears in extremely low yields in cannabis samples and it is believed to be a product of oxidation of cannabichromevarin, mainly during long term storage of cannabis (PMID: 6991645). C19H26O2 286.42 286.1933 (1R,9R,12S,14R)-9,13,13-trimethyl-5-propyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol (1R,9R,12S,14R)-9,13,13-trimethyl-5-propyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol CCCC1=CC(O)=C2[C@@H]3[C@H]4[C@H](CC[C@@]4(C)OC2=C1)C3(C)C InChI=1S/C19H26O2/c1-5-6-11-9-13(20)15-14(10-11)21-19(4)8-7-12-16(19)17(15)18(12,2)3/h9-10,12,16-17,20H,5-8H2,1-4H3/t12-,16+,17+,19+/m0/s1 FGYVFYUCBIDEEZ-ZHCSWWCTSA-N belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 4.98 ALOGPS logs -4.86 ALOGPS logp 4.77 ChemAxon pka_strongest_acidic 10.02 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (1R,9R,12S,14R)-9,13,13-trimethyl-5-propyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2,4,6-trien-3-ol ChemAxon average_mass 286.42 ChemAxon mono_mass 286.1933 ChemAxon smiles CCCC1=CC(O)=C2[C@@H]3[C@H]4[C@H](CC[C@@]4(C)OC2=C1)C3(C)C ChemAxon formula C19H26O2 ChemAxon inchi InChI=1S/C19H26O2/c1-5-6-11-9-13(20)15-14(10-11)21-19(4)8-7-12-16(19)17(15)18(12,2)3/h9-10,12,16-17,20H,5-8H2,1-4H3/t12-,16+,17+,19+/m0/s1 ChemAxon inchikey FGYVFYUCBIDEEZ-ZHCSWWCTSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 84.62 ChemAxon polarizability 33.59 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444397 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:14 UTC 2020-08-04 22:28:18 UTC CDB000423 Cannabielsoic acid A Cannabielsoic acid A, also known as cannabielsoate A or CBEA-C5 A, is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabielsoic acid A is a dihydroxybenzoic acid derived from cannabidiolic acid. As such, it is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabielsoic acid A can be considered a polyketide, a monoterpenoid and a resorcinol derivative, due to the meta arrangement of its two hydroxil groups on the bencene ring. Cannabielsoic acid A, also belongs to the class of cannabis compounds known as Cannabielsoins. There are two types of cannabielsoic acids, cannabielsoic acid A (CBEA-C5 A) and cannabielsoic acid B (CBEA-C5 B). The inclusion of cannabielsoic acids as Cannabis natural products is somewhat controversial because they have been isolated and identified infrequently and because they can be obtained by the photo-oxidation of CBD (cannabidiol). However, cannabielsoic acids have been repeatedly mentioned in the literature as natural cannabinoids and are considered as a part of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645). Cannabielsoate a C22H30O5 374.48 374.2093 (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2(7),3,5-triene-4-carboxylic acid (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2(7),3,5-triene-4-carboxylic acid CCCCCC1=CC2=C([C@@H]3[C@H](O2)[C@@](C)(O)CC[C@H]3C(C)=C)C(O)=C1C(O)=O InChI=1S/C22H30O5/c1-5-6-7-8-13-11-15-18(19(23)16(13)21(24)25)17-14(12(2)3)9-10-22(4,26)20(17)27-15/h11,14,17,20,23,26H,2,5-10H2,1,3-4H3,(H,24,25)/t14-,17+,20-,22-/m0/s1 OQCOBNKTUMOOHJ-RSGMMRJUSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Coumarans Cyclic alcohols and derivatives Hydrocarbon derivatives Menthane monoterpenoids Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Salicylic acid and derivatives Tertiary alcohols Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Aromatic monoterpenoid Benzenoid Carboxylic acid Carboxylic acid derivative Coumaran Cyclic alcohol Ether Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle P-menthane monoterpenoid Salicylic acid or derivatives Tertiary alcohol Vinylogous acid logp 4.08 ALOGPS logs -3.61 ALOGPS logp 5.31 ChemAxon pka_strongest_acidic 2.9 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2(7),3,5-triene-4-carboxylic acid ChemAxon average_mass 374.48 ChemAxon mono_mass 374.2093 ChemAxon smiles CCCCCC1=CC2=C([C@@H]3[C@H](O2)[C@@](C)(O)CC[C@H]3C(C)=C)C(O)=C1C(O)=O ChemAxon formula C22H30O5 ChemAxon inchi InChI=1S/C22H30O5/c1-5-6-7-8-13-11-15-18(19(23)16(13)21(24)25)17-14(12(2)3)9-10-22(4,26)20(17)27-15/h11,14,17,20,23,26H,2,5-10H2,1,3-4H3,(H,24,25)/t14-,17+,20-,22-/m0/s1 ChemAxon inchikey OQCOBNKTUMOOHJ-RSGMMRJUSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 104.2 ChemAxon polarizability 41.96 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444405 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:17 UTC 2020-08-04 22:28:18 UTC CDB000424 Cannabielsoic acid B Cannabielsoic acid B, also known as cannabielsoate B or CBEA-C5 B, is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabielsoic acid B is a dihydroxybenzoic acid derived from cannabidiolic acid. As such, it is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabielsoic acid B can be considered a polyketide, a monoterpenoid and a resorcinol derivative, due to the meta arrangement of its two hydroxil groups on the bencene ring. Cannabielsoic acid B, also belongs to the class of cannabis compounds known as Cannabielsoins. There are two types of cannabielsoic acids, cannabielsoic acid A (CBEA-C5 A) and cannabielsoic acid B (CBEA-C5 B). The inclusion of cannabielsoic acids as Cannabis natural products is somewhat controversial because they have been isolated and identified infrequently and also because they can be obtained by the photo-oxidation of CBD (cannabidiol). However, cannabielsoic acids have been repeatedly mentioned in the literature as natural cannabinoids and are considered as a part of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645). Cannabielsoate b C22H30O5 374.48 374.2093 (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-6-carboxylic acid (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-6-carboxylic acid CCCCCC1=CC2=C([C@@H]3[C@H](O2)[C@@](C)(O)CC[C@H]3C(C)=C)C(O)=C1C(O)=O InChI=1S/C22H30O5/c1-5-6-7-8-13-11-15-18(19(23)16(13)21(24)25)17-14(12(2)3)9-10-22(4,26)20(17)27-15/h11,14,17,20,23,26H,2,5-10H2,1,3-4H3,(H,24,25)/t14-,17+,20-,22-/m0/s1 OQCOBNKTUMOOHJ-RSGMMRJUSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Carboxylic acids Coumarans Cyclic alcohols and derivatives Hydrocarbon derivatives Hydroxybenzoic acid derivatives Menthane monoterpenoids Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Tertiary alcohols 1-hydroxy-2-unsubstituted benzenoid Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Aromatic monoterpenoid Benzenoid Carboxylic acid Carboxylic acid derivative Coumaran Cyclic alcohol Ether Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle P-menthane monoterpenoid Tertiary alcohol logp 4.03 ALOGPS logs -3.61 ALOGPS logp 4.66 ChemAxon pka_strongest_acidic 3.85 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1R,9S,10S,13R)-3,10-dihydroxy-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-6-carboxylic acid ChemAxon average_mass 374.48 ChemAxon mono_mass 374.2093 ChemAxon smiles CCCCCC1=CC2=C([C@@H]3[C@H](O2)[C@@](C)(O)CC[C@H]3C(C)=C)C(O)=C1C(O)=O ChemAxon formula C22H30O5 ChemAxon inchi InChI=1S/C22H30O5/c1-5-6-7-8-13-11-15-18(19(23)16(13)21(24)25)17-14(12(2)3)9-10-22(4,26)20(17)27-15/h11,14,17,20,23,26H,2,5-10H2,1,3-4H3,(H,24,25)/t14-,17+,20-,22-/m0/s1 ChemAxon inchikey OQCOBNKTUMOOHJ-RSGMMRJUSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 104.2 ChemAxon polarizability 42.04 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444401 58828795 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:20 UTC 2020-08-04 22:24:08 UTC CDB000027 Cannabielsoin Cannabielsoin (CBE) is a phytocannabinoid and a part of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645). Cannabielsoin is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Thus, cannabielsoin can be considered a polyketide, a monoterpenoid and a resorcinol derivative, due to the meta arrangement of its two hydroxil groups (one of them in the form of an ether) on the bencene ring. Similarly, to the case of the cannabielsoic acids, the inclusion of cannabielsoin as a cannabis natural product is controversial because it has been isolated and identified infrequently. Additionally, cannabielsoin is most likely a product of the photo-oxidation of cannabidiol (CBD). It has also been detected as a metabolite from CBD in mammals (PMID: 1806944), suggesting that CBE is not a natural product but more likely an artifact. However, cannabielsoin has been repeatedly mentioned in the literature as a natural cannabinoid and is therefore considered a cannabinoid. Cannabielsoin a CBE C21H30O3 330.47 330.2195 (1R,9S,10S,13R)-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-3,10-diol (1R,9S,10S,13R)-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-3,10-diol 52025-76-0 CCCCCC1=CC(O)=C2[C@@H]3[C@H](OC2=C1)[C@@](C)(O)CC[C@H]3C(C)=C InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-20-18(19)15(13(2)3)9-10-21(20,4)23/h11-12,15,18,20,22-23H,2,5-10H2,1,3-4H3/t15-,18+,20-,21-/m0/s1 RBEAVAMWZAJWOI-MTOHEIAKSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Coumarans Cyclic alcohols and derivatives Hydrocarbon derivatives Menthane monoterpenoids Oxacyclic compounds Tertiary alcohols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Aromatic monoterpenoid Benzenoid Coumaran Cyclic alcohol Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle P-menthane monoterpenoid Tertiary alcohol logp 5.22 ALOGPS logs -4.48 ALOGPS logp 5.01 ChemAxon pka_strongest_acidic 9.89 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (1R,9S,10S,13R)-10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-2,4,6-triene-3,10-diol ChemAxon average_mass 330.47 ChemAxon mono_mass 330.2195 ChemAxon smiles CCCCCC1=CC(O)=C2[C@@H]3[C@H](OC2=C1)[C@@](C)(O)CC[C@H]3C(C)=C ChemAxon formula C21H30O3 ChemAxon inchi InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-20-18(19)15(13(2)3)9-10-21(20,4)23/h11-12,15,18,20,22-23H,2,5-10H2,1,3-4H3/t15-,18+,20-,21-/m0/s1 ChemAxon inchikey RBEAVAMWZAJWOI-MTOHEIAKSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 96.95 ChemAxon polarizability 38.96 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20218 162113 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Yamamoto I, Gohda H, Narimatsu S, Watanabe K, Yoshimura H: Cannabielsoin as a new metabolite of cannabidiol in mammals. Pharmacol Biochem Behav. 1991 Nov;40(3):541-6. doi: 10.1016/0091-3057(91)90360-e. 1806944 1.0 2020-03-19 00:36:23 UTC 2020-09-11 20:09:01 UTC CDB000028 Cannabinolic acid Cannabinolic acid (CBNA), belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. It is one of the 120 cannabinoid compounds found in cannabis plants (PMID: 6991645). CBNA, belongs to a subclass of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol. Cannabinolic acid is formed through the degradation THCA (Tetrahydrocannabinolic acid). CBNA was first isolated in 1965 (PMID: 5879350) and is a non-psychoactive compound. Heating can lead to the decarboxylation of CBNA resulting in the formation of the more psychoactive CBN. 1-Hydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylate C22H26O4 354.45 354.1831 1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid cannabinolic acid A 2808-39-1 CCCCCC1=CC2=C(C(O)=C1C(O)=O)C1=C(C=CC(C)=C1)C(C)(C)O2 InChI=1S/C22H26O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9-12,23H,5-8H2,1-4H3,(H,24,25) KXKOBIRSQLNUPS-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Alkyl aryl ethers Carboxylic acids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Salicylic acid and derivatives Vinylogous acids 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Carboxylic acid Carboxylic acid derivative Dibenzopyran Ether Hydrocarbon derivative Hydroxybenzoic acid Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Phenol Salicylic acid or derivatives Vinylogous acid logp 5.47 ALOGPS logs -5.03 ALOGPS logp 6.72 ChemAxon pka_strongest_acidic 2.85 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid ChemAxon average_mass 354.45 ChemAxon mono_mass 354.1831 ChemAxon smiles CCCCCC1=CC2=C(C(O)=C1C(O)=O)C1=C(C=CC(C)=C1)C(C)(C)O2 ChemAxon formula C22H26O4 ChemAxon inchi InChI=1S/C22H26O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9-12,23H,5-8H2,1-4H3,(H,24,25) ChemAxon inchikey KXKOBIRSQLNUPS-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 102.99 ChemAxon polarizability 40.76 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 3081990 Mechoulam R, Gaoni Y: Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids. Tetrahedron. 1965 May;21(5):1223-9. doi: 10.1016/0040-4020(65)80064-3. 5879350 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:27 UTC 2020-09-11 20:09:01 UTC CDB000029 Cannabinol Cannabinol (CBN), belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol is the best known and most abundant member of the cannabinoid subclass of cannabis compounds known as cannabinols or CBNs. Cannabinol is psychoactive, although in a lesser degree as THC and related compounds. CBN is most likely a degradation product of tetrahydrocannabinoic acid (THCA) or of tetrahydrocannabinol (THC). CBN can also be obtained through the decarboxilation of cannabinolic acid (CBNA), another product of the degradation of THCA (PMID: 1140243). Independently of the routes by which CBN is produced, it is found in higher quantities in Cannabis products that have been stored over an extended period of time or that have been exposed to sunlight or heat (PMID: 26870049). CBN is mildly psychoactive (PMID: 1221432) and acts as a partial agonist of the CB1 and CB2 receptors, with a higher affinity for the CB2 receptors (PMID: 11020293). In both cases the affinity of CBN to these receptors is lower than that of THC (PMID: 9667767). The legal status of CBN is uncertain, as it is not included in the United Nations‚Äô Convention on Psychotropic Substances. However, it could still be considered as an analogue of THC in some states of the United States of America, leaving open the possibility of penal prosecution. The main pharmacological characteristics of Cannabinol are sedative, antibiotic, anticonvulsant and anti-inflammatory (PMID: 6991645). Cannabinol (CBN) is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol 3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran CBN C21H26O2 310.44 310.1933 6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol cannabinol 521-35-7 CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1 InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3 VBGLYOIFKLUMQG-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Dibenzopyran Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Cannabinoids Other aromatic polyketides Other aromatic polyketides dibenzopyran logp 6.58 ALOGPS logs -5.96 ALOGPS logp 6.41 ChemAxon pka_strongest_acidic 9.32 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol ChemAxon average_mass 310.44 ChemAxon mono_mass 310.1933 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1 ChemAxon formula C21H26O2 ChemAxon inchi InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3 ChemAxon inchikey VBGLYOIFKLUMQG-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 95.74 ChemAxon polarizability 37.75 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 2543 C07580 Cannabinol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 McCallum ND, Yagen B, Levy S, Mechoulam R: Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol. Experientia. 1975 May 15;31(5):520-1. doi: 10.1007/bf01932433. 1140243 Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE: Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology. 1975;13(6):502-12. doi: 10.1159/000136944. 1221432 Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK: Novel cannabinol probes for CB1 and CB2 cannabinoid receptors. J Med Chem. 2000 Oct 5;43(20):3778-85. doi: 10.1021/jm0001572. 11020293 Petitet F, Jeantaud B, Reibaud M, Imperato A, Dubroeucq MC: Complex pharmacology of natural cannabinoids: evidence for partial agonist activity of delta9-tetrahydrocannabinol and antagonist activity of cannabidiol on rat brain cannabinoid receptors. Life Sci. 1998;63(1):PL1-6. doi: 10.1016/s0024-3205(98)00238-0. 9667767 1.0 2020-03-19 00:36:30 UTC 2020-07-22 22:11:10 UTC CDB000030 Cannabinol methylether Cannabinol methylether (CBNM) belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol methylether, belongs to the class of cannabis compounds known as Cannabinols and is the methoxylated derivative of the bioactive cannabinol (CBN). Cannabinol methylether is one of the more than 120 cannabinoid compounds that are known in cannabis plant (PMID: 6991645). Cannabinol methylether is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C22H28O2 324.46 324.2089 1-methoxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene 1-methoxy-6,6,9-trimethyl-3-pentylbenzo[c]chromene CCCCCC1=CC(OC)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1 InChI=1S/C22H28O2/c1-6-7-8-9-16-13-19(23-5)21-17-12-15(2)10-11-18(17)22(3,4)24-20(21)14-16/h10-14H,6-9H2,1-5H3 YEDIZIGYIMTZKP-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 2-benzopyrans Alkyl aryl ethers Anisoles Hydrocarbon derivatives Oxacyclic compounds 2-benzopyran Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Dibenzopyran Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle logp 6.63 ALOGPS logs -7.04 ALOGPS logp 6.56 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 1-methoxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene ChemAxon average_mass 324.46 ChemAxon mono_mass 324.2089 ChemAxon smiles CCCCCC1=CC(OC)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1 ChemAxon formula C22H28O2 ChemAxon inchi InChI=1S/C22H28O2/c1-6-7-8-9-16-13-19(23-5)21-17-12-15(2)10-11-18(17)22(3,4)24-20(21)14-16/h10-14H,6-9H2,1-5H3 ChemAxon inchikey YEDIZIGYIMTZKP-UHFFFAOYSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 100.22 ChemAxon polarizability 39.58 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 628150 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:34 UTC 2020-08-04 22:24:08 UTC CDB000031 Cannabinol-C4 Cannabinol-C4, also known as CBN-C4, belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol-C4 also belongs to the class of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol or cannabinol-C5 (CBN or CBN-C5). CBN has a 5-carbon aliphatic chain attached to its phenol group, while CBN-C4 has a 4-carbon aliphatic chain. Other CBNs have 1, 2 or 3 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. Cannabinols are mildly psychoactive cannabinoids found only in trace amounts (PMID: 1221432) and are mostly found in aged cannabis (PMID:26870049). Pharmacologically relevant quantities are formed as a metabolite of tetrahydrocannabinol (THC) (PMID: 1140243). Cannabinols act as partial agonists of the CB1 receptors but tend to have higher affinities to CB2 receptors. The relative activity and CB1/CB2 affinity of CBN-C4 versus CBN-C5 has not been determined. Cannabinol-C4 is one of more than 120 cannabinoid compounds that can be found in cannabis plants (PMID: 6991645). C20H24O2 296.41 296.1776 3-butyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol 3-butyl-6,6,9-trimethylbenzo[c]chromen-1-ol CCCCC1=CC2=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)(C)O2 InChI=1S/C20H24O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h8-12,21H,5-7H2,1-4H3 GGVVJZIANMUEJO-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Dibenzopyran Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 6.08 ALOGPS logs -5.52 ALOGPS logp 5.97 ChemAxon pka_strongest_acidic 9.32 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 3-butyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol ChemAxon average_mass 296.41 ChemAxon mono_mass 296.1776 ChemAxon smiles CCCCC1=CC2=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)(C)O2 ChemAxon formula C20H24O2 ChemAxon inchi InChI=1S/C20H24O2/c1-5-6-7-14-11-17(21)19-15-10-13(2)8-9-16(15)20(3,4)22-18(19)12-14/h8-12,21H,5-7H2,1-4H3 ChemAxon inchikey GGVVJZIANMUEJO-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 91.14 ChemAxon polarizability 35.57 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444392 Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE: Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology. 1975;13(6):502-12. doi: 10.1159/000136944. 1221432 Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 McCallum ND, Yagen B, Levy S, Mechoulam R: Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol. Experientia. 1975 May 15;31(5):520-1. doi: 10.1007/bf01932433. 1140243 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:36 UTC 2020-08-04 22:24:08 UTC CDB000032 Cannabivarin Cannabivarin (CBV), also known as Cannabivarol, belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. CBV is considered a non-psychoactive cannabinoid. It does not produce the euphoric side effects found in THC. Minor amounts of CBV are found in the hemp varieties of Cannabis sativa. CBV also belongs to the class of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol or cannabinol-C5 (CBN or CBN-C5). CBN has a 5-carbon aliphatic chain attached to its phenol group, while CBV has a 3-carbon aliphatic chain. Other CBNs have 1, 2 or 4 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. CBV is an oxidation product of tetrahydrocannabivarin (THCV, THV). CBV is one of more than 120 cannabinoid compounds that can be found in cannabis plants (PMID: 6991645). C19H22O2 282.38 282.162 6,6,9-trimethyl-3-propyl-6H-benzo[c]chromen-1-ol cannabivarin 33745-21-0 CCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1 InChI=1S/C19H22O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h7-11,20H,5-6H2,1-4H3 SVTKBAIRFMXQQF-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Dibenzopyran Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle logp 5.61 ALOGPS logs -4.89 ALOGPS logp 5.52 ChemAxon pka_strongest_acidic 9.32 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 6,6,9-trimethyl-3-propyl-6H-benzo[c]chromen-1-ol ChemAxon average_mass 282.38 ChemAxon mono_mass 282.162 ChemAxon smiles CCCC1=CC(O)=C2C(OC(C)(C)C3=C2C=C(C)C=C3)=C1 ChemAxon formula C19H22O2 ChemAxon inchi InChI=1S/C19H22O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h7-11,20H,5-6H2,1-4H3 ChemAxon inchikey SVTKBAIRFMXQQF-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 86.53 ChemAxon polarizability 33.48 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 622545 Cannabivarin Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:39 UTC 2020-08-04 22:24:08 UTC CDB000033 Cannabinol-C2 Cannabinol-C2 (CBN-C2) belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol-C2 also belongs to the class of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol or cannabinol-C5 (CBN or CBN-C5). CBN has a 5-carbon aliphatic chain attached to its phenol group, while CBN-C2 has a 2-carbon atom aliphatic chain. Other CBNs have 1, 3 or 4 carbon atom chains. These shorter chain cannabinols are even less abundant than CBN-C5. Cannabinols are mildly psychoactive cannabinoids found only in trace amounts (PMID: 1221432) and are mostly found in aged cannabis (PMID:26870049). Pharmacologically relevant quantities of CBN-C5 are formed as a metabolite of tetrahydrocannabinol, which is also known as THC (PMID: 1140243). Cannabinols act as partial agonists of the CB1 receptors but tend to have higher affinities to CB2 receptors. The relative activity and CB1/CB2 affinity of CBN-C2 versus CBN-C5 has not been determined. Cannabinol-C2 is one of more than 120 cannabinoid compounds that can be found in cannabis plants (PMID: 6991645). C18H20O2 268.36 268.1463 3-ethyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol 3-ethyl-6,6,9-trimethylbenzo[c]chromen-1-ol CCC1=CC2=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)(C)O2 InChI=1S/C18H20O2/c1-5-12-9-15(19)17-13-8-11(2)6-7-14(13)18(3,4)20-16(17)10-12/h6-10,19H,5H2,1-4H3 QUYCDNSZSMEFBQ-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Dibenzopyran Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 5.16 ALOGPS logs -4.72 ALOGPS logp 5.08 ChemAxon pka_strongest_acidic 9.32 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 3-ethyl-6,6,9-trimethyl-6H-benzo[c]chromen-1-ol ChemAxon average_mass 268.36 ChemAxon mono_mass 268.1463 ChemAxon smiles CCC1=CC2=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)(C)O2 ChemAxon formula C18H20O2 ChemAxon inchi InChI=1S/C18H20O2/c1-5-12-9-15(19)17-13-8-11(2)6-7-14(13)18(3,4)20-16(17)10-12/h6-10,19H,5H2,1-4H3 ChemAxon inchikey QUYCDNSZSMEFBQ-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 81.93 ChemAxon polarizability 31.28 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444399 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE: Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology. 1975;13(6):502-12. doi: 10.1159/000136944. 1221432 Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 McCallum ND, Yagen B, Levy S, Mechoulam R: Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol. Experientia. 1975 May 15;31(5):520-1. doi: 10.1007/bf01932433. 1140243 Khan MZ, Nawaz W: The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system. Biomed Pharmacother. 2016 Oct;83:439-449. doi: 10.1016/j.biopha.2016.07.002. Epub 2016 Jul 15. 27424325 Sathyanarayana Rao TS, Yeragani VK: Hypertensive crisis and cheese. Indian J Psychiatry. 2009 Jan;51(1):65-6. doi: 10.4103/0019-5545.44910. 19742203 1.0 2020-03-19 00:36:41 UTC 2020-07-24 23:30:15 UTC CDB000432 Cannabiorcol Cannabiorcol (CBN-C1), also known as Cannabinol-C1, belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Cannabinol-C1 also belongs to the class of cannabis compounds known as cannabinols or CBNs. The best known and most abundant CBN is cannabinol or cannabinol-C5 (CBN or CBN-C5). CBN has a 5-carbon aliphatic chain attached to its phenol group, while CBN-C1 has a methyl group attached at position 6 of its phenol group. Other CBNs have 2, 3 or 4 carbon atom sidechains. These shorter chain cannabinols are even less abundant than CBN-C5. Cannabinols are mildly psychoactive cannabinoids found only in trace amounts (PMID: 1221432) and are mostly found in aged cannabis (PMID:26870049). Pharmacologically relevant quantities of CBN-C5 are formed as a metabolite of tetrahydrocannabinol, which is also known as THC (PMID: 1140243). Cannabinols act as partial agonists of the CB1 receptors but tend to have higher affinities to CB2 receptors. The relative activity and CB1/CB2 affinity of CBN-C1 versus CBN-C5 has not been determined. Cannabiorcol is one of more than 120 cannabinoid compounds that can be found in cannabis plants (PMID: 6991645). C17H22O2 258.36 258.162 3,6,6,9-tetramethyl-6H-benzo[c]chromen-1-ol 3,6,6,9-tetramethylbenzo[c]chromen-1-ol 22972-65-2 CC1=C[C@@H]2[C@@H](CC1)C(C)(C)OC1=CC(C)=CC(O)=C21 InChI=1S/C17H22O2/c1-10-5-6-13-12(7-10)16-14(18)8-11(2)9-15(16)19-17(13,3)4/h7-9,12-13,18H,5-6H2,1-4H3/t12-,13-/m1/s1 WIDIPARNVYRVNW-CHWSQXEVSA-N belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. Dibenzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Dibenzopyran Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 4.80 ALOGPS logs -4.40 ALOGPS logp 4.63 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 3,6,6,9-tetramethyl-6H-benzo[c]chromen-1-ol ChemAxon average_mass 258.36 ChemAxon mono_mass 258.162 ChemAxon smiles CC1=C[C@@H]2[C@@H](CC1)C(C)(C)OC1=CC(C)=CC(O)=C21 ChemAxon formula C17H22O2 ChemAxon inchi InChI=1S/C17H22O2/c1-10-5-6-13-12(7-10)16-14(18)8-11(2)9-15(16)19-17(13,3)4/h7-9,12-13,18H,5-6H2,1-4H3/t12-,13-/m1/s1 ChemAxon inchikey WIDIPARNVYRVNW-CHWSQXEVSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 77.33 ChemAxon polarizability 29.26 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444404 58828797 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE: Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology. 1975;13(6):502-12. doi: 10.1159/000136944. 1221432 Andre CM, Hausman JF, Guerriero G: Cannabis sativa: The Plant of the Thousand and One Molecules. Front Plant Sci. 2016 Feb 4;7:19. doi: 10.3389/fpls.2016.00019. eCollection 2016. 26870049 McCallum ND, Yagen B, Levy S, Mechoulam R: Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol. Experientia. 1975 May 15;31(5):520-1. doi: 10.1007/bf01932433. 1140243 1.0 2020-03-19 00:36:44 UTC 2020-07-10 00:17:46 UTC CDB000433 Cannabinodiol Cannabinodiol (CBND) is a psychoactive cannabinoid (PMID: 30023762). It is present in Cannabis sativa plants at very low concentrations (doi:10.1016/0031-9422(77)80023-X). Cannabinodiol and Cannabinodivarin (CBVD) are the only two known members of the cannabinodiol class of cannabinoids (PMID: 6991645). CBND is the fully aromatized derivative of cannabidiol (CBD). Even though the oxidation of CBD to CBND seems to be a rational mechanism of conversion, it has not been proven experimentally. Oppositely, it has been experimentally demonstrated that CBD occurs through the photochemical reaction of cannabinol (CBN) with UV light, with the opening of the pyrane ring (https://doi.org/10.1039/C39750000797). Cannabinodiol is one of more than 120 cannabinoid compounds that are known to occur in cannabis (PMID: 6991645). Cannabinodiol is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C21H26O2 310.44 310.1933 5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-[1,1'-biphenyl]-2,6-diol 5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-[1,1'-biphenyl]-2,6-diol CCCCCC1=CC(O)=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)=C InChI=1S/C21H26O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h9-13,22-23H,2,5-8H2,1,3-4H3 TWKHUZXSTKISQC-UHFFFAOYSA-N belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. Biphenyls and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Hydrocarbon derivatives Organooxygen compounds Phenylpropenes Resorcinols Styrenes Toluenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Biphenyl Hydrocarbon derivative Organic oxygen compound Organooxygen compound Phenol Phenylpropene Resorcinol Styrene Toluene logp 5.79 ALOGPS logs -4.80 ALOGPS logp 6.85 ChemAxon pka_strongest_acidic 9.11 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-[1,1'-biphenyl]-2,6-diol ChemAxon average_mass 310.44 ChemAxon mono_mass 310.1933 ChemAxon smiles CCCCCC1=CC(O)=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)=C ChemAxon formula C21H26O2 ChemAxon inchi InChI=1S/C21H26O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h9-13,22-23H,2,5-8H2,1,3-4H3 ChemAxon inchikey TWKHUZXSTKISQC-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 97.61 ChemAxon polarizability 37.22 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11551346 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Lewis MM, Yang Y, Wasilewski E, Clarke HA, Kotra LP: Chemical Profiling of Medical Cannabis Extracts. ACS Omega. 2017 Sep 30;2(9):6091-6103. doi: 10.1021/acsomega.7b00996. Epub 2017 Sep 22. 30023762 1.0 2020-03-19 00:36:47 UTC 2020-07-07 15:58:25 UTC CDB000434 Cannabinodivarin Cannabinodivarin (CBVD) is the C3 analogue of Cannabinnodiol (CBND). It is present in Cannabis sativa plants at very low concentrations. Cannabinodiol and Cannabinodivarin (CBVD) are the only two known members of the cannabinodiol class of cannabinoids (PMID: 6991645). CBVD is the fully aromatized derivative of cannabidivarin (CBDV). No experimental data exist as to how CBDV is produced. Even though the oxidation of CBD to CBND seems to be a rational mechanism of conversion, it has not been proven experimentally. It is very likely, however, that the mechanism would be similar to what has been experimentally demonstrated for the photochemical conversion of cannabinol (CBN) into CBD, with the opening of the pyrane ring (https://doi.org/10.1039/C39750000797). Cannabinodiol is one of more than 120 cannabinoid compounds that are known to occur in cannabis (PMID: 6991645). C19H22O2 282.38 282.162 5'-methyl-2'-(prop-1-en-2-yl)-4-propyl-[1,1'-biphenyl]-2,6-diol 5'-methyl-2'-(prop-1-en-2-yl)-4-propyl-[1,1'-biphenyl]-2,6-diol CCCC1=CC(O)=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)=C InChI=1S/C19H22O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h7-11,20-21H,2,5-6H2,1,3-4H3 COURSARJQZMTEZ-UHFFFAOYSA-N belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. Biphenyls and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Hydrocarbon derivatives Organooxygen compounds Phenylpropanes Phenylpropenes Resorcinols Styrenes Toluenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic homomonocyclic compound Biphenyl Hydrocarbon derivative Organic oxygen compound Organooxygen compound Phenol Phenylpropane Phenylpropene Resorcinol Styrene Toluene logp 4.93 ALOGPS logs -4.24 ALOGPS logp 5.97 ChemAxon pka_strongest_acidic 9.12 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 5'-methyl-2'-(prop-1-en-2-yl)-4-propyl-[1,1'-biphenyl]-2,6-diol ChemAxon average_mass 282.38 ChemAxon mono_mass 282.162 ChemAxon smiles CCCC1=CC(O)=C(C(O)=C1)C1=C(C=CC(C)=C1)C(C)=C ChemAxon formula C19H22O2 ChemAxon inchi InChI=1S/C19H22O2/c1-5-6-14-10-17(20)19(18(21)11-14)16-9-13(4)7-8-15(16)12(2)3/h7-11,20-21H,2,5-6H2,1,3-4H3 ChemAxon inchikey COURSARJQZMTEZ-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 88.41 ChemAxon polarizability 33 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444390 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:49 UTC 2020-07-24 23:30:07 UTC CDB000435 Cannabitriol Cannabitriol (CBT) was first isolated in 1966 and its structure was established in 1976 (https://doi.org/10.1080/00021369.1966.10858651; PMID: 1253891). CBT shares the same basic skeleton of THC with the addition of two hydroxil groups and the isomerization of a double bond on the isoprenoid moiety. Little experimental data has been published in regards to the biological activities of CBT. It has been proposed that CBT is an intermediate in the aromatization of delta-9-THC to cannabinol (CBN) (PMID: 27722705). Cannabitriol has been described as one of the cannabinoids isolated from Cannabis sativa plants (PMID: 6991645). C21H30O4 346.47 346.2144 (9S,10S)-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9,10-triol (9S,10S)-6,6,9-trimethyl-3-pentyl-7H,8H,10H-cyclohexa[c]chromene-1,9,10-triol 74184-29-5 CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2[C@H](O)[C@@](C)(O)CC3)=C1 InChI=1S/C21H30O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,19,22-24H,5-10H2,1-4H3/t19-,21-/m0/s1 ZLYNXDIDWUWASO-FPOVZHCZSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1,2-diols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds Secondary alcohols Tertiary alcohols 1,2-diol 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Polyol Secondary alcohol Tertiary alcohol logp 4.35 ALOGPS logs -3.96 ALOGPS logp 3.81 ChemAxon pka_strongest_acidic 9.24 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (9S,10S)-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9,10-triol ChemAxon average_mass 346.47 ChemAxon mono_mass 346.2144 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2[C@H](O)[C@@](C)(O)CC3)=C1 ChemAxon formula C21H30O4 ChemAxon inchi InChI=1S/C21H30O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,19,22-24H,5-10H2,1-4H3/t19-,21-/m0/s1 ChemAxon inchikey ZLYNXDIDWUWASO-FPOVZHCZSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 99.36 ChemAxon polarizability 40.33 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 156460 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Chan WR, Magnus KE, Watson HA: The structure of cannabitriol. Experientia. 1976 Mar 15;32(3):283-4. doi: 10.1007/BF01940792. 1253891 Hanus LO, Meyer SM, Munoz E, Taglialatela-Scafati O, Appendino G: Phytocannabinoids: a unified critical inventory. Nat Prod Rep. 2016 Nov 23;33(12):1357-1392. doi: 10.1039/c6np00074f. 27722705 1.0 2020-03-19 00:36:52 UTC 2020-08-04 22:24:08 UTC CDB000034 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol is one of more than 120 cannabinoid compounds that are known in cannabis plants (PMID: 6991645). 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol is an ethoxylated derivative of cannabitriol (CBT). Unlike the methylated derivatives, which are naturally produced by the action of the SAM enzyme (PMID: 16766004), ethoxylated metabolites are very rarely found as plant natural products and are instead often found as artifacts produced during extraction procedures employing ethanol as the extraction solvent. The isolation of 10-Ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol from Cannabis sativa extracts was reported in 1977, together with cannabitriol (PMID: 895385). (9S)-3-Pentyl-6,6,9-trimethyl-10a-ethoxy-7,8,9,10-tetrahydro-6H-dibenzo[b,D]pyran-1,9a-diol (9S)-3-Pentyl-6,6,9-trimethyl-10α-ethoxy-7,8,9,10-tetrahydro-6H-dibenzo[b,D]pyran-1,9α-diol C23H34O4 374.52 374.2457 (9S,10R)-10-ethoxy-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol (9S,10R)-10-ethoxy-6,6,9-trimethyl-3-pentyl-7H,8H,10H-cyclohexa[c]chromene-1,9-diol CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2[C@@H](OCC)[C@@](C)(O)CC3)=C1 InChI=1S/C23H34O4/c1-6-8-9-10-15-13-17(24)20-18(14-15)27-22(3,4)16-11-12-23(5,25)21(19(16)20)26-7-2/h13-14,21,24-25H,6-12H2,1-5H3/t21-,23+/m1/s1 HRAUOPAWWNBNRN-GGAORHGYSA-N logp 4.82 ALOGPS logs -4.50 ALOGPS logp 4.8 ChemAxon pka_strongest_acidic 9.24 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (9S,10R)-10-ethoxy-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol ChemAxon average_mass 374.52 ChemAxon mono_mass 374.2457 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2[C@@H](OCC)[C@@](C)(O)CC3)=C1 ChemAxon formula C23H34O4 ChemAxon inchi InChI=1S/C23H34O4/c1-6-8-9-10-15-13-17(24)20-18(14-15)27-22(3,4)16-11-12-23(5,25)21(19(16)20)26-7-2/h13-14,21,24-25H,6-12H2,1-5H3/t21-,23+/m1/s1 ChemAxon inchikey HRAUOPAWWNBNRN-GGAORHGYSA-N ChemAxon polar_surface_area 58.92 ChemAxon refractivity 108.86 ChemAxon polarizability 44.12 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 49871313 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. doi: 10.1016/j.phytochem.2006.04.019. 16766004 Elsohly MA, El-Feraly FS, Turner CE: Isolation and characterization of (+)-cannabitriol and (-)-10-ethoxy-9-hydroxy-delta 6a[10a]-tetrahydrocannabinol: two new cannabinoids from Cannabis sativa L. extract. Lloydia. 1977 May-Jun;40(3):275-80. 895385 Groce JW, Jones LA: Carbohydrate and cyclitol content of cannabis. J Agric Food Chem. 1973 Mar-Apr;21(2):211-4. doi: 10.1021/jf60186a003. 4688907 1.0 2020-03-19 00:36:55 UTC 2020-07-31 20:34:13 UTC CDB000035 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol, also belongs to the subclass of cannabis compounds known as Cannabitriols. 8,9-Dihydroxy-delta-6a-tetrahydrocannabinol is one of more than 120 cannabinoid compounds that are known in cannabis plant (PMID: 6991645). It was first characterized in the hexane extract of an Indian variant of Cannabis sativa L. in 1978 (DOI: 10.1007/BF01922908). C21H30O4 346.47 346.2144 (8S,9R)-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,8,9-triol (8S,9R)-6,6,9-trimethyl-3-pentyl-7H,8H,10H-cyclohexa[c]chromene-1,8,9-triol CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C[C@@](C)(O)[C@@H](O)C3)=C1 InChI=1S/C21H30O4/c1-5-6-7-8-13-9-16(22)19-14-12-21(4,24)18(23)11-15(14)20(2,3)25-17(19)10-13/h9-10,18,22-24H,5-8,11-12H2,1-4H3/t18-,21+/m0/s1 WEVYNIJDEFFKLF-GHTZIAJQSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1,2-diols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds Secondary alcohols Tertiary alcohols 1,2-diol 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Polyol Secondary alcohol Tertiary alcohol logp 3.86 ALOGPS logs -4.02 ALOGPS logp 3.65 ChemAxon pka_strongest_acidic 9.35 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (8S,9R)-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,8,9-triol ChemAxon average_mass 346.47 ChemAxon mono_mass 346.2144 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC(C)(C)C3=C2C[C@@](C)(O)[C@@H](O)C3)=C1 ChemAxon formula C21H30O4 ChemAxon inchi InChI=1S/C21H30O4/c1-5-6-7-8-13-9-16(22)19-14-12-21(4,24)18(23)11-15(14)20(2,3)25-17(19)10-13/h9-10,18,22-24H,5-8,11-12H2,1-4H3/t18-,21+/m0/s1 ChemAxon inchikey WEVYNIJDEFFKLF-GHTZIAJQSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 99.51 ChemAxon polarizability 40.64 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:36:57 UTC 2020-06-29 20:40:56 UTC CDB000438 Cannabitriolvarin Cannabitriolvarin (CBTV) is the C3 analogue of cannabitriol (CBT). CBTV has been reported very scarcely in the literature. Cannabitriolvarin, also belongs to the class of cannabis compounds known as Cannabitriol. CBTV shares the same basic skeleton of tetrahydrocannabivarin (THCV) with the addition of two hydroxil groups and the isomerization of a double bond on the isoprenoid moiety. Little experimental data has been published in regards to the biological activities of CBTV. It has been proposed that CBTV is an intermediate in the aromatization of THCV to cannabivarin (CBV) (PMID: 27722705). Cannabitriolvarin has been described as one of the cannabinoids isolated from Cannabis sativa plants (PMID: 6991645). C19H26O3 302.41 302.1882 (9R)-6,6,9-trimethyl-3-propyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol (9R)-6,6,9-trimethyl-3-propyl-7H,8H,10H-cyclohexa[c]chromene-1,9-diol CCCC1=CC2=C(C(O)=C1)C1=C(CC[C@@](C)(O)C1)C(C)(C)O2 InChI=1S/C19H26O3/c1-5-6-12-9-15(20)17-13-11-19(4,21)8-7-14(13)18(2,3)22-16(17)10-12/h9-10,20-21H,5-8,11H2,1-4H3/t19-/m1/s1 SWBMWFGNFZCROR-LJQANCHMSA-N logp 4.13 ALOGPS logs -3.99 ALOGPS logp 3.83 ChemAxon pka_strongest_acidic 9.36 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (9R)-6,6,9-trimethyl-3-propyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol ChemAxon average_mass 302.41 ChemAxon mono_mass 302.1882 ChemAxon smiles CCCC1=CC2=C(C(O)=C1)C1=C(CC[C@@](C)(O)C1)C(C)(C)O2 ChemAxon formula C19H26O3 ChemAxon inchi InChI=1S/C19H26O3/c1-5-6-12-9-15(20)17-13-11-19(4,21)8-7-14(13)18(2,3)22-16(17)10-12/h9-10,20-21H,5-8,11H2,1-4H3/t19-/m1/s1 ChemAxon inchikey SWBMWFGNFZCROR-LJQANCHMSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 88.95 ChemAxon polarizability 35.35 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Hanus LO, Meyer SM, Munoz E, Taglialatela-Scafati O, Appendino G: Phytocannabinoids: a unified critical inventory. Nat Prod Rep. 2016 Nov 23;33(12):1357-1392. doi: 10.1039/c6np00074f. 27722705 1.0 2020-03-19 00:37:00 UTC 2020-06-29 20:40:56 UTC CDB000439 Ethoxy-cannabitriolvarin Ethoxy-cannabitriolvarin (CBTVE) is an ethoxylated derivative of cannabivarin (CBV). Unlike the methylated derivatives, which are naturally produced by the action of the SAM enzyme (PMID: 16766004), ethoxylated metabolites are very rarely found as plant natural products and are instead often found as artifacts produced during extraction procedures employing ethanol as the extraction solvent. CBTVE was isolated from a 140-year-old Cannabis sativa extract and reported in 1985 (PMID: 6991645). Regardless, ethoxy-cannabitriolvarin is one of more than 120 cannabinoid compounds reported to have been isolated from in Cannabis sativa (PMID: 6991645). C21H30O4 346.47 346.2144 (9S)-10-ethoxy-6,6,9-trimethyl-3-propyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol (9S)-10-ethoxy-6,6,9-trimethyl-3-propyl-7H,8H,10H-cyclohexa[c]chromene-1,9-diol CCCC1=CC2=C(C(O)=C1)C1=C(CC[C@](C)(O)C1OCC)C(C)(C)O2 InChI=1S/C21H30O4/c1-6-8-13-11-15(22)18-16(12-13)25-20(3,4)14-9-10-21(5,23)19(17(14)18)24-7-2/h11-12,19,22-23H,6-10H2,1-5H3/t19-,21-/m0/s1 RFAYJRLIEJZHOI-FPOVZHCZSA-N logp 3.86 ALOGPS logs -4.07 ALOGPS logp 3.92 ChemAxon pka_strongest_acidic 9.24 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (9S)-10-ethoxy-6,6,9-trimethyl-3-propyl-6H,7H,8H,9H,10H-cyclohexa[c]chromene-1,9-diol ChemAxon average_mass 346.47 ChemAxon mono_mass 346.2144 ChemAxon smiles CCCC1=CC2=C(C(O)=C1)C1=C(CC[C@](C)(O)C1OCC)C(C)(C)O2 ChemAxon formula C21H30O4 ChemAxon inchi InChI=1S/C21H30O4/c1-6-8-13-11-15(22)18-16(12-13)25-20(3,4)14-9-10-21(5,23)19(17(14)18)24-7-2/h11-12,19,22-23H,6-10H2,1-5H3/t19-,21-/m0/s1 ChemAxon inchikey RFAYJRLIEJZHOI-FPOVZHCZSA-N ChemAxon polar_surface_area 58.92 ChemAxon refractivity 99.65 ChemAxon polarizability 39.86 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. doi: 10.1016/j.phytochem.2006.04.019. 16766004 1.0 2020-03-19 00:37:02 UTC 2020-08-04 22:28:18 UTC CDB000440 Dehydrocannabifuran Dehydrocannabifuran belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. Dehydrocannabifuran is one of more than 120 cannabinoid compounds that have been identified in cannabis plants (PMID: 6991645). Structurally it can be considered as the fully aromatized derivative of cannabielsoin (CBE). As CBE, dehydrocannabifuran is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). Similarly to the case of cannabielsoin, the inclusion of dehydrocannabifuran as a Cannabis natural product is controversial, because it has been isolated and identified infrequently. Additionally, dehydrocannabifuran can be considered a derivative of cannabielsoin, which is most likely a product of the photo-oxidation of cannabidiol (CBD). Mention of dehydrocannabifuran in the scientific literature is very scarce and no reports on its biological activity exist. Dehydrocannabifuran is also found in cannabis smoke and is volatilized during the combustion of cannabis (DOI: 10.1007/978-1-59259-947-9_2). C21H24O2 308.42 308.1776 10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol 10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol 56154-59-7 CCCCCC1=CC(O)=C2C(OC3=C(C)C=CC(C(C)=C)=C23)=C1 InChI=1S/C21H24O2/c1-5-6-7-8-15-11-17(22)20-18(12-15)23-21-14(4)9-10-16(13(2)3)19(20)21/h9-12,22H,2,5-8H2,1,3-4H3 NAGBBYZBIQVPIQ-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. Dibenzofurans Organic compounds Organoheterocyclic compounds Benzofurans Dibenzofurans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Furans Heteroaromatic compounds Hydrocarbon derivatives Organooxygen compounds Oxacyclic compounds Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic heteropolycyclic compound Benzenoid Dibenzofuran Furan Heteroaromatic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol Styrene logp 7.06 ALOGPS logs -4.86 ALOGPS logp 6.69 ChemAxon pka_strongest_acidic 8.8 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 10-methyl-5-pentyl-13-(prop-1-en-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol ChemAxon average_mass 308.42 ChemAxon mono_mass 308.1776 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC3=C(C)C=CC(C(C)=C)=C23)=C1 ChemAxon formula C21H24O2 ChemAxon inchi InChI=1S/C21H24O2/c1-5-6-7-8-15-11-17(22)20-18(12-15)23-21-14(4)9-10-16(13(2)3)19(20)21/h9-12,22H,2,5-8H2,1,3-4H3 ChemAxon inchikey NAGBBYZBIQVPIQ-UHFFFAOYSA-N ChemAxon polar_surface_area 33.37 ChemAxon refractivity 95.66 ChemAxon polarizability 37.47 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 59444381 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:37:06 UTC 2020-08-04 22:28:18 UTC CDB000441 Cannabifuran Cannabifuran (CBF) belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. CBF is the reduced derivative of dehydrocannabifuran. As such it can be considered as a fully aromatized derivative of cannabielsoin (CBE). As CBE, cannabifuran is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 0.1016/B978-0-12-800756-3.00002-8). Similarly to the case of cannabielsoin, the inclusion of cannabifuran as a Cannabis natural product is controversial because it has been isolated and identified infrequently. Additionally, cannabifuran can be considered a derivative of cannabielsoin, which is most likely a product of the photo-oxidation of cannabidiol (CBD). Mention of cannabifuran in the scientific literature is very scarce and no reports on its biological activity exist. Cannabifuran is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (DOI: 10.1007/978-1-59259-947-9_2). C21H26O2 310.44 310.1933 10-methyl-5-pentyl-13-(propan-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol 13-isopropyl-10-methyl-5-pentyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol CCCCCC1=CC(O)=C2C(OC3=C(C)C=CC(C(C)C)=C23)=C1 InChI=1S/C21H26O2/c1-5-6-7-8-15-11-17(22)20-18(12-15)23-21-14(4)9-10-16(13(2)3)19(20)21/h9-13,22H,5-8H2,1-4H3 VNGQMWZHHNCMLQ-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. Dibenzofurans Organic compounds Organoheterocyclic compounds Benzofurans Dibenzofurans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Cumenes Furans Heteroaromatic compounds Hydrocarbon derivatives Organooxygen compounds Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic heteropolycyclic compound Benzenoid Cumene Dibenzofuran Furan Heteroaromatic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Phenol logp 7.00 ALOGPS logs -4.99 ALOGPS logp 6.9 ChemAxon pka_strongest_acidic 8.9 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 10-methyl-5-pentyl-13-(propan-2-yl)-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-3-ol ChemAxon average_mass 310.44 ChemAxon mono_mass 310.1933 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC3=C(C)C=CC(C(C)C)=C23)=C1 ChemAxon formula C21H26O2 ChemAxon inchi InChI=1S/C21H26O2/c1-5-6-7-8-15-11-17(22)20-18(12-15)23-21-14(4)9-10-16(13(2)3)19(20)21/h9-13,22H,5-8H2,1-4H3 ChemAxon inchikey VNGQMWZHHNCMLQ-UHFFFAOYSA-N ChemAxon polar_surface_area 33.37 ChemAxon refractivity 95.88 ChemAxon polarizability 38.28 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 9966466 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:37:11 UTC 2020-07-07 15:58:28 UTC CDB000442 Cannabichromanon Cannabichromanone, also known as CBCN, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Cannabichromanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Cannabichromanone, also belongs to the class of cannabis compounds known as Miscellaneous cannabinoid. Cannabichromanone is one of more than 120 cannabinoid compounds that are known in cannabis plant. (PMID: 6991645) C20H28O4 332.44 332.1988 (3S)-5-hydroxy-2,2-dimethyl-3-(3-oxobutyl)-7-pentyl-3,4-dihydro-2H-1-benzopyran-4-one (3S)-5-hydroxy-2,2-dimethyl-3-(3-oxobutyl)-7-pentyl-3H-1-benzopyran-4-one CCCCCC1=CC(O)=C2C(=O)[C@@H](CCC(C)=O)C(C)(C)OC2=C1 InChI=1S/C20H28O4/c1-5-6-7-8-14-11-16(22)18-17(12-14)24-20(3,4)15(19(18)23)10-9-13(2)21/h11-12,15,22H,5-10H2,1-4H3/t15-/m1/s1 NHZMSIOYBVIOAF-OAHLLOKOSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Aryl alkyl ketones Chromones Hydrocarbon derivatives Organic oxides Oxacyclic compounds Vinylogous acids 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Carbonyl group Chromone Ether Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Phenol Vinylogous acid logp 4.64 ALOGPS logs -4.36 ALOGPS logp 5.09 ChemAxon pka_strongest_acidic 8.84 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (3S)-5-hydroxy-2,2-dimethyl-3-(3-oxobutyl)-7-pentyl-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 332.44 ChemAxon mono_mass 332.1988 ChemAxon smiles CCCCCC1=CC(O)=C2C(=O)[C@@H](CCC(C)=O)C(C)(C)OC2=C1 ChemAxon formula C20H28O4 ChemAxon inchi InChI=1S/C20H28O4/c1-5-6-7-8-14-11-16(22)18-17(12-14)24-20(3,4)15(19(18)23)10-9-13(2)21/h11-12,15,22H,5-10H2,1-4H3/t15-/m1/s1 ChemAxon inchikey NHZMSIOYBVIOAF-OAHLLOKOSA-N ChemAxon polar_surface_area 63.6 ChemAxon refractivity 94.54 ChemAxon polarizability 38.73 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 25105340 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:37:14 UTC 2020-08-04 22:24:08 UTC CDB000036 Cannabicitran Cannabicitran belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Cannabicitran possesses a tetracyclic skeleton, unique in the cannabinoid class of secondary metabolites. Interestingly, cannabicitran was first synthesized in 1971 (https://doi.org/10.1039/J39710000796) and later isolated from a natural cannabis source in 1974 (https://doi.org/10.1016/S0031-9422(00)91362-1) and its absolute configuration is still unknown (PMID: 6991645). No published data exists regarding cannabicitran‚Äôs biological or pharmacological activities. Cannabicitran is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C21H30O2 314.47 314.2246 (1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene (1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene CCCCCC1=CC2=C3[C@H]4C[C@](C)(CC[C@@H]4C(C)(C)O2)OC3=C1 InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3/t15-,16-,21-/m0/s1 IXJXRDCCQRZSDV-QYWGDWMGSA-N logp 7.01 ALOGPS logs -6.82 ALOGPS logp 5.62 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac (1S,4S,13S)-1,5,5-trimethyl-9-pentyl-6,15-dioxatetracyclo[9.3.1.0^{4,13}.0^{7,12}]pentadeca-7(12),8,10-triene ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC2=C3[C@H]4C[C@](C)(CC[C@@H]4C(C)(C)O2)OC3=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-14-11-17-19-15-13-21(4,23-18(19)12-14)10-9-16(15)20(2,3)22-17/h11-12,15-16H,5-10,13H2,1-4H3/t15-,16-,21-/m0/s1 ChemAxon inchikey IXJXRDCCQRZSDV-QYWGDWMGSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 93.86 ChemAxon polarizability 38.51 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 129360466 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:37:16 UTC 2020-08-04 22:24:08 UTC CDB000037 10-Oxo-delta-6a-tetrahydrocannabinol 10-Oxo-delta-6a-tetrahydrocannabinol (OTHC) belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 10-Oxo-delta-6a-tetrahydrocannabinol is the oxidized derivative of delta-6a-tetrahydrocannabinol, carrying a ketone group at position 10. Very little information regarding its biological activities is available in the scientific literature. 10-Oxo-delta-6a-tetrahydrocannabinol is one of more than 120 cannabinoid compounds that are known to occur in cannabis plants (PMID: 6991645). C21H28O3 328.45 328.2038 (9S)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromen-10-one (9S)-1-hydroxy-6,6,9-trimethyl-3-pentyl-7H,8H,9H-cyclohexa[c]chromen-10-one CCCCCC1=CC2=C(C(O)=C1)C1=C(CC[C@H](C)C1=O)C(C)(C)O2 InChI=1S/C21H28O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-21(3,4)15-10-9-13(2)20(23)18(15)19/h11-13,22H,5-10H2,1-4H3/t13-/m0/s1 UEFGHYCIOXYTOG-ZDUSSCGKSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Cyclohexenones Hydrocarbon derivatives Organic oxides Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Carbonyl group Cyclohexenone Ether Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxacycle logp 5.55 ALOGPS logs -4.40 ALOGPS logp 5.71 ChemAxon pka_strongest_acidic 8.96 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (9S)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,7H,8H,9H,10H-cyclohexa[c]chromen-10-one ChemAxon average_mass 328.45 ChemAxon mono_mass 328.2038 ChemAxon smiles CCCCCC1=CC2=C(C(O)=C1)C1=C(CC[C@H](C)C1=O)C(C)(C)O2 ChemAxon formula C21H28O3 ChemAxon inchi InChI=1S/C21H28O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-21(3,4)15-10-9-13(2)20(23)18(15)19/h11-13,22H,5-10H2,1-4H3/t13-/m0/s1 ChemAxon inchikey UEFGHYCIOXYTOG-ZDUSSCGKSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 97.11 ChemAxon polarizability 38.76 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Fuke G, Nornberg JL: Systematic evaluation on the effectiveness of conjugated linoleic acid in human health. Crit Rev Food Sci Nutr. 2017 Jan 2;57(1):1-7. doi: 10.1080/10408398.2012.716800. 27636835 Cunnane SC, Anderson MJ: Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and [1-14C]linoleate oxidation. J Lipid Res. 1997 Apr;38(4):805-12. 9144095 Ruthig DJ, Meckling-Gill KA: Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelial cell line, IEC-6. J Nutr. 1999 Oct;129(10):1791-8. doi: 10.1093/jn/129.10.1791. 10498749 Letawe C, Boone M, Pierard GE: Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones. Clin Exp Dermatol. 1998 Mar;23(2):56-8. doi: 10.1046/j.1365-2230.1998.00315.x. 9692305 Ando H, Ryu A, Hashimoto A, Oka M, Ichihashi M: Linoleic acid and alpha-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin. Arch Dermatol Res. 1998 Jul;290(7):375-81. doi: 10.1007/s004030050320. 9749992 1.0 2020-03-19 00:37:20 UTC 2020-08-04 22:24:08 UTC CDB000038 Delta-9-cis-tetrahydrocannabinol Delta-9-cis-tetrahydrocannabinol (Cis-THC) belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Delta-9-cis-tetrahydrocannabinol is the cis isomer of the more abundant, and well known, THC. Delta-9-cis-tetrahydrocannabinol was found as a major contaminant in samples of confiscated marijuana (PMID: 6991645).The actions of THC result from its partial agonist activity at the cannabinoid receptor CB1, located mainly in the central nervous system, and the CB2 receptor, mainly expressed in cells of the immune system¬†(PMID: 17828291).¬†Delta-9-cis-tetrahydrocannabinol is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C21H30O2 314.47 314.2246 (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol 43009-38-7 CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@@H]3C(C)(C)OC2=C1 InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1 CYQFCXCEBYINGO-SJORKVTESA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Hydrocarbon derivatives Oxacyclic compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle logp 7.29 ALOGPS logs -5.08 ALOGPS logp 5.94 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol ChemAxon average_mass 314.47 ChemAxon mono_mass 314.2246 ChemAxon smiles CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@@H]3C(C)(C)OC2=C1 ChemAxon formula C21H30O2 ChemAxon inchi InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1 ChemAxon inchikey CYQFCXCEBYINGO-SJORKVTESA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 96.73 ChemAxon polarizability 38.77 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12831993 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Pertwee RG: The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. Br J Pharmacol. 2008 Jan;153(2):199-215. doi: 10.1038/sj.bjp.0707442. Epub 2007 Sep 10. 17828291 1.0 2020-03-19 00:37:24 UTC 2020-06-19 18:40:59 UTC CDB000446 3,4,5,6-Tetrahydro-7-hydroxy-alpha-alpha-2-trimethyl-9-propyl-2,6-methano-2H-1-benzoxocin-5-methanol 3,4,5,6-Tetrahydro-7-hydroxy-alpha-alpha-2-trimethyl-9-propyl-2,6-methano-2H-1-benzoxocin-5-methanol, also known as OH-iso-HHCV, belongs to organic compounds. It is one of more than 120 cannabinoid compounds that are known in cannabis plant. It belongs to the Miscellaneous class of cannabinoid compounds. (PMID: 6991645) C19H28O3 304.43 304.2038 (1R,9R,12R)-12-(2-hydroxypropan-2-yl)-9-methyl-5-propyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-3-ol (1R,9R,12R)-12-(2-hydroxypropan-2-yl)-9-methyl-5-propyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-3-ol CCCC1=CC2=C([C@@H]3C[C@@](C)(CC[C@H]3C(C)(C)O)O2)C(O)=C1 InChI=1S/C19H28O3/c1-5-6-12-9-15(20)17-13-11-19(4,22-16(17)10-12)8-7-14(13)18(2,3)21/h9-10,13-14,20-21H,5-8,11H2,1-4H3/t13-,14-,19-/m1/s1 RRQVSLLVCGRJNI-PJIJBLCYSA-N logp 4.61 ALOGPS logs -4.03 ALOGPS logp 4.07 ChemAxon pka_strongest_acidic 10.04 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (1R,9R,12R)-12-(2-hydroxypropan-2-yl)-9-methyl-5-propyl-8-oxatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-3-ol ChemAxon average_mass 304.43 ChemAxon mono_mass 304.2038 ChemAxon smiles CCCC1=CC2=C([C@@H]3C[C@@](C)(CC[C@H]3C(C)(C)O)O2)C(O)=C1 ChemAxon formula C19H28O3 ChemAxon inchi InChI=1S/C19H28O3/c1-5-6-12-9-15(20)17-13-11-19(4,22-16(17)10-12)8-7-14(13)18(2,3)21/h9-10,13-14,20-21H,5-8,11H2,1-4H3/t13-,14-,19-/m1/s1 ChemAxon inchikey RRQVSLLVCGRJNI-PJIJBLCYSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 88.44 ChemAxon polarizability 35.49 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:37:27 UTC 2020-07-24 23:30:07 UTC CDB000447 Cannabiripsol Cannabiripsol belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Cannabiripsol is a cannabinoid, first isolated from a South African Cannabis variant and its structure was determined by spectrometric analysis and synthesis. Cannabirispsol corresponds to a dehydro derivative of cannabitriol (PMID: 499397). No further information regarding its biological activity has been published. It is one of the cannabinoid compounds identified in Cannabis sativa plants (PMID: 6991645). Cannabiripsol, (6ar-(6aalpha,9alpha,10beta,10abeta))-isomer (6AR,9S,10S,10ar)-9,10-dihydroxyhexahydrocannabinol Cannabiripsol, (6ar-(6aalpha,9alpha,10alpha,10abeta))-isomer C21H32O4 348.48 348.2301 (6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromene-1,9,10-triol (6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10H,10aH-benzo[c]isochromene-1,9,10-triol 72236-32-9 CCCCCC1=CC(O)=C2[C@@H]3[C@H](O)[C@@](C)(O)CC[C@H]3C(C)(C)OC2=C1 InChI=1S/C21H32O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,14,17,19,22-24H,5-10H2,1-4H3/t14-,17-,19+,21+/m1/s1 TZGCTXUTNDNTTE-DYZHCLJRSA-N belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 2,2-dimethyl-1-benzopyrans Organic compounds Organoheterocyclic compounds Benzopyrans 1-benzopyrans Aromatic heteropolycyclic compounds 1,2-diols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Cyclic alcohols and derivatives Hydrocarbon derivatives Oxacyclic compounds Secondary alcohols Tertiary alcohols 1,2-diol 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2,2-dimethyl-1-benzopyran Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Cyclic alcohol Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Polyol Secondary alcohol Tertiary alcohol logp 4.11 ALOGPS logs -3.90 ALOGPS logp 3.96 ChemAxon pka_strongest_acidic 9.9 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromene-1,9,10-triol ChemAxon average_mass 348.48 ChemAxon mono_mass 348.2301 ChemAxon smiles CCCCCC1=CC(O)=C2[C@@H]3[C@H](O)[C@@](C)(O)CC[C@H]3C(C)(C)OC2=C1 ChemAxon formula C21H32O4 ChemAxon inchi InChI=1S/C21H32O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,14,17,19,22-24H,5-10H2,1-4H3/t14-,17-,19+,21+/m1/s1 ChemAxon inchikey TZGCTXUTNDNTTE-DYZHCLJRSA-N ChemAxon polar_surface_area 69.92 ChemAxon refractivity 98.93 ChemAxon polarizability 40.93 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 192007 Boeren EG, Elsohly MA, Turner CE: Cannabiripsol: a novel Cannabis constituent. Experientia. 1979 Oct 15;35(10):1278-9. doi: 10.1007/BF01963954. 499397 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:37:29 UTC 2020-08-04 22:24:09 UTC CDB000039 6a,7,10a-Trihydroxy-delta-9-tetrahydrocannabinol 6a,7,10a trihydroxy-delta-9-tetrahydrocannabinol, also known as triOH-THC, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. It is a trihydroxylated derivative of THC and one of the more than 120 cannabinoids that are known to occur in cannabis plants (PMID: 6991645). THC is the principal psychoactive constituent of cannabis. The actions of THC and THC derivatives result from their partial agonist activity on the cannabinoid receptor CB1, located mainly in the central nervous system, and the CB2 receptor, mainly expressed in cells of the immune system. 6a,7,10a-Trihydroxy-delta-9-tetrahydrocannabinnol was first isolated and identified as a cannabis constituent in 1979 from a hexane extract of small leaves, stems, and flowering tops of Mexican marijuana produced in Mississippi. The hexane soluble fractions were partitioned with KOH, and the aqueous layer was neutralized and extracted with petroleum ether and purified by column chromatography (PMID: 6991645). 6a,7,10a trihydroxy-delta-9-tetrahydrocannabinol is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C21H30O5 362.47 362.2093 (6aR,7R,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-1,6a,7,10a-tetrol (6aR,7R,10aS)-6,6,9-trimethyl-3-pentyl-7H,8H-benzo[c]isochromene-1,6a,7,10a-tetrol CCCCCC1=CC(O)=C2C(OC(C)(C)[C@@]3(O)[C@H](O)CC(C)=C[C@]23O)=C1 InChI=1S/C21H30O5/c1-5-6-7-8-14-10-15(22)18-16(11-14)26-19(3,4)21(25)17(23)9-13(2)12-20(18,21)24/h10-12,17,22-25H,5-9H2,1-4H3/t17-,20+,21+/m1/s1 ANVPZESCUZNHQB-QMMLZNLJSA-N logp 2.56 ALOGPS logs -3.26 ALOGPS logp 3.1 ChemAxon pka_strongest_acidic 9.83 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (6aR,7R,10aS)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-1,6a,7,10a-tetrol ChemAxon average_mass 362.47 ChemAxon mono_mass 362.2093 ChemAxon smiles CCCCCC1=CC(O)=C2C(OC(C)(C)[C@@]3(O)[C@H](O)CC(C)=C[C@]23O)=C1 ChemAxon formula C21H30O5 ChemAxon inchi InChI=1S/C21H30O5/c1-5-6-7-8-14-10-15(22)18-16(11-14)26-19(3,4)21(25)17(23)9-13(2)12-20(18,21)24/h10-12,17,22-25H,5-9H2,1-4H3/t17-,20+,21+/m1/s1 ChemAxon inchikey ANVPZESCUZNHQB-QMMLZNLJSA-N ChemAxon polar_surface_area 90.15 ChemAxon refractivity 100.61 ChemAxon polarizability 41.06 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kromhout D, Menotti A, Bloemberg B, Aravanis C, Blackburn H, Buzina R, Dontas AS, Fidanza F, Giampaoli S, Jansen A, et al.: Dietary saturated and trans fatty acids and cholesterol and 25-year mortality from coronary heart disease: the Seven Countries Study. Prev Med. 1995 May;24(3):308-15. doi: 10.1006/pmed.1995.1049. 7644455 1.0 2020-03-19 00:37:32 UTC 2020-08-04 22:28:19 UTC CDB000449 trans-gamma-Bisabolene Trans-gamma-Bisabolene or (E)-gamma-bisabolene is biochemically a sesquiterpenoid. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-Bisabolene is considered to be an isoprenoid lipid molecule, as such, Beta-Bisabolene is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Bisabolene has three isomers (Œ±-, Œ≤-, and Œ≥-bisabolene) which differ by the positions of the double bonds. Bisabolenes are naturally occurring sesquiterpenoid found in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, oregano and found in trace amounts in cannabis plants (PMID: 6991645). Trans-gamma-Bisabolene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Bisabolenes are also produced in different insects such as stink bugs, fruit flies and by several fungi (PMID: 11673844; PMID: 25957494). C15H24 204.36 204.1878 (4Z)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene (Z)-gamma-bisabolene 11003-31-9 CC(C)=CCC\C(C)=C1\CCC(C)=CC1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+ XBGUIVFBMBVUEG-CCEZHUSRSA-N logp 5.88 ALOGPS logs -3.55 ALOGPS logp 4.78 ChemAxon iupac (4Z)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC\C(C)=C1\CCC(C)=CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+ ChemAxon inchikey XBGUIVFBMBVUEG-CCEZHUSRSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.09 ChemAxon polarizability 26.94 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Lu F, Teal PE: Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Arch Insect Biochem Physiol. 2001 Nov;48(3):144-54. doi: 10.1002/arch.1067. 11673844 Spakowicz DJ, Strobel SA: Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential. Appl Microbiol Biotechnol. 2015 Jun;99(12):4943-51. doi: 10.1007/s00253-015-6641-y. Epub 2015 May 10. 25957494 1.0 2020-03-19 00:37:38 UTC 2020-07-24 23:30:15 UTC CDB000451 Beta-Fenchol Beta-Fenchol also known as Beta-fenchyl alcohol or Exo-fenchol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-Fenchol is an isomer of Fenchol. Fenchol is a colorless or white solid, that occurs widely in nature. Fenchol gives basil its characteristic scent and comprises 15.9% of the volatile oils of some species of Aster (https://doi.org/10.1016/j.foodchem.2006.03.021). b-Fenchol Β-fenchol C10H18O 154.25 154.1358 (1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 22627-95-8 CC1(C)[C@H]2CC[C@](C)(C2)[C@@H]1O InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1 IAIHUHQCLTYTSF-QXFUBDJGSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Fenchane monoterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol logp 2.30 ALOGPS logs -2.25 ALOGPS logp 2.15 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac (1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@H]2CC[C@](C)(C2)[C@@H]1O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1 ChemAxon inchikey IAIHUHQCLTYTSF-QXFUBDJGSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.16 ChemAxon polarizability 18.5 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6973643 1.0 2020-03-19 00:37:42 UTC 2020-08-04 22:28:19 UTC CDB000452 Guajol Guajol or Guaiacol, also known as 2-hydroxyanisole or 2-methoxyphenol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Guaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is a sweet, medicinal, and phenolic tasting compound. Guaiacol is found in the highest concentration within a few different foods, such as sesames, coffee, and white wines and in a lower concentration in peppermints. Guaiacol has also been detected, but not quantified in white mustards, peppers, red bell peppers, cherry tomato, turmerics, and Cannabis sativa (https://doi.org/10.1271/bbb1961.30.619). Guaiacol is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation (PMID: 16152729). Guaiacol is used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (PMID 4344880, 16152729) 1-Hydroxy-2-methoxybenzene 2-Hydroxyanisole Catechol monomethyl ether O-Methoxyphenol Creodon 2-Methoxyphenol 2-Methoxy-phenol Anastil Guaiacol (liquid) extra pure Guaiastil Guaicol Guaicolina Guajakol Guajol Guasol Guiacol Methoxyphenol Methylcatachol Methylcatechol O-Guaiacol O-Hydroxyanisole O-Methoxy-phenol O-Methyl catechol Pyrocatechol monomethyl ether Pyroguaiac acid 2-Hydroxy-anisole Catechol, methyl Methyl catechol 2-Methoxyl-4-vinylphenol Guaiacol C7H8O2 124.14 124.0524 2-methoxyphenol guaiacol 8021-39-4 COC1=CC=CC=C1O InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3 LHGVFZTZFXWLCP-UHFFFAOYSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyphenols Organic compounds Benzenoids Phenols Methoxyphenols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound a guaiacol monomethoxybenzene phenols water_solubility 18.7 mg/mL at 15 °C logp 1.32 HANSCH,C ET AL. (1995) melting_point 28 °C logp 1.32 ALOGPS logs -0.27 ALOGPS logp 1.51 ChemAxon pka_strongest_acidic 9.98 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxyphenol ChemAxon average_mass 124.14 ChemAxon mono_mass 124.0524 ChemAxon smiles COC1=CC=CC=C1O ChemAxon formula C7H8O2 ChemAxon inchi InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3 ChemAxon inchikey LHGVFZTZFXWLCP-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 34.5 ChemAxon polarizability 12.69 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 447 FDB011885 460 650 C15572 DB11359 28591 CPD-400 C00029459 Guaiacol 6217 Rogers LE, Lyon GM Jr, Porter FS: Spot test for vanillylmandelic acid and other guaiacols in urine of patients with neuroblastoma. Am J Clin Pathol. 1972 Oct;58(4):383-7. doi: 10.1093/ajcp/58.5.383. 4344880 Mimurai T, Yazaki K, Sawaki K, Ozawa T, Kawaguchi M: Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: reaction kinetic study. Biomed Res. 2005 Aug;26(4):139-45. doi: 10.2220/biomedres.26.139. 16152729 Duffey SS, Aldrich JR, Blum MS: Biosynthesis of phenol and guaiacol by the hemipteran Leptoglossus phyllopus. Comp Biochem Physiol B. 1977;56(2):101-2. doi: 10.1016/0305-0491(77)90029-3. 830476 Dorfner R, Ferge T, Kettrup A, Zimmermann R, Yeretzian C: Real-time monitoring of 4-vinylguaiacol, guaiacol, and phenol during coffee roasting by resonant laser ionization time-of-flight mass spectrometry. J Agric Food Chem. 2003 Sep 10;51(19):5768-73. doi: 10.1021/jf0341767. 12952431 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:37:44 UTC 2020-09-11 20:08:30 UTC CDB000453 alpha-Guaiene alpha-Guaiene (Œ±-guaiene) belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ±-Guaiene is one of three isomers of Guaiene (Œ±-Guaiene, Œ≤-Guaiene, and Œ¥-Guaiene). Œ±-Guaiene is the most common member of this group and was first isolated from guaiac wood oil from Bulnesia sarmientoi. It has since been detected in several plant species, including Cannabis sativa (PMID: 31816756) The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes. a-Guaiene Α-guaiene C15H24 204.36 204.1878 (1S,4S,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene guaiene 3691-12-1 C[C@H]1CCC2=C1C[C@@H](CC[C@@H]2C)C(C)=C InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+/m0/s1 ADIDQIZBYUABQK-RWMBFGLXSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon carbobicyclic compound sesquiterpene logp 5.80 ALOGPS logs -3.94 ALOGPS logp 4.46 ChemAxon iupac (1S,4S,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H]1CCC2=C1C[C@@H](CC[C@@H]2C)C(C)=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+/m0/s1 ChemAxon inchikey ADIDQIZBYUABQK-RWMBFGLXSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.26 ChemAxon polarizability 26.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5317844 63443 C20161 CPD-8749 C00020377 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. 31816756 1.0 2020-03-19 00:37:47 UTC 2020-09-11 20:08:31 UTC CDB000454 alpha-Eudesmol Alpha-eudesmol (Œ±-eudesmol) is a member of the class of compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquitepenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-eudesmol is practically insoluble in water but soluble in organic solvents such as methanol, ethanol and ethyl acetate. Alpha-eudesmol can be found in orange, mint, wild celery, ginger, and Cannabis sativa (PMID: 31816756; PMID:18242187). (2R,4AR,8ar)-1,2,3,4,4a,5,6,8a-octahydro-alpha,alpha,4a,8-tetramethyl-2-naphthalenemethanol (2R,4AR,8ar)-1,2,3,4,4a,5,6,8a-octahydro-a,a,4a,8-tetramethyl-2-naphthalenemethanol (2R,4AR,8ar)-1,2,3,4,4a,5,6,8a-octahydro-α,α,4a,8-tetramethyl-2-naphthalenemethanol a-Eudesmol Α-eudesmol 1,2,3,4,4a,5,6,8a-Octahydro-alpha,alpha,4a,8-tetramethyl-(2R-(2alpha,4aalpha,8abeta))-2-naphthalenemethanol C15H26O 222.37 222.1984 2-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]propan-2-ol α-eudesmol 473-16-5 CC1=CCC[C@]2(C)CC[C@H](C[C@@H]12)C(C)(C)O InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h6,12-13,16H,5,7-10H2,1-4H3/t12-,13+,15-/m1/s1 FCSRUSQUAVXUKK-VNHYZAJKSA-N belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol Eudesmanes eudesmane sesquiterpenoid logp 4.82 ALOGPS logs -3.71 ALOGPS logp 3.47 ChemAxon pka_strongest_acidic 19.32 ChemAxon pka_strongest_basic -0.91 ChemAxon iupac 2-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]propan-2-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC1=CCC[C@]2(C)CC[C@H](C[C@@H]12)C(C)(C)O ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h6,12-13,16H,5,7-10H2,1-4H3/t12-,13+,15-/m1/s1 ChemAxon inchikey FCSRUSQUAVXUKK-VNHYZAJKSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 69.43 ChemAxon polarizability 27.55 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C09663 10278 92762 C00000163 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Delgado-Povedano MM, Sanchez-Carnerero Callado C, Priego-Capote F, Ferreiro-Vera C: Untargeted characterization of extracts from Cannabis sativa L. cultivars by gas and liquid chromatography coupled to mass spectrometry in high resolution mode. Talanta. 2020 Feb 1;208:120384. doi: 10.1016/j.talanta.2019.120384. Epub 2019 Sep 25. 31816756 Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, Tanaka Y, Misawa N, Utsumi R: Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. FEBS Lett. 2008 Mar 5;582(5):565-72. doi: 10.1016/j.febslet.2008.01.020. Epub 2008 Jan 31. 18242187 1.0 2020-03-19 00:37:55 UTC 2020-07-29 16:16:11 UTC CDB000456 Cis-Sabinene hydrate Cis-sabinene hydrate is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cis-sabinene hydrate is practically insoluble in water but soluble in organic solvents such as methanol, ethanol and ethyl acetate. Cis-sabinene hydrate is a balsamic tasting compound and can be found in several plant species such as sweet marjoram, spearmint, common sage, and pot marjoram. Cis-Sabinene hydrate is also one of the many terpenes that can be found in Cannabis sativa plants (PMID: 6991645). C10H18 138.25 138.1409 (1S,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexane (1S,4R,5S)-1-isopropyl-4-methylbicyclo[3.1.0]hexane CC(C)[C@]12C[C@H]1[C@H](C)CC2 InChI=1S/C10H18/c1-7(2)10-5-4-8(3)9(10)6-10/h7-9H,4-6H2,1-3H3/t8-,9+,10+/m1/s1 GCTNBVHDRFKLLK-UTLUCORTSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Polycyclic hydrocarbons Saturated hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Hydrocarbon Polycyclic hydrocarbon Saturated hydrocarbon Thujane monoterpenoid logp 3.63 ALOGPS logs -4.56 ALOGPS logp 3.21 ChemAxon iupac (1S,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexane ChemAxon average_mass 138.25 ChemAxon mono_mass 138.1409 ChemAxon smiles CC(C)[C@]12C[C@H]1[C@H](C)CC2 ChemAxon formula C10H18 ChemAxon inchi InChI=1S/C10H18/c1-7(2)10-5-4-8(3)9(10)6-10/h7-9H,4-6H2,1-3H3/t8-,9+,10+/m1/s1 ChemAxon inchikey GCTNBVHDRFKLLK-UTLUCORTSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.87 ChemAxon polarizability 17.88 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12315145 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:38:01 UTC 2020-09-11 20:08:29 UTC CDB000458 Beta-Eudesmol Beta-Eudesmol, also known as beta-selinenol belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-eudesmol is a green and wood tasting compound that can be found in a number of food items such as common walnut, sweet basil, ginkgo nuts, burdock, and ginger (PMID: 18242187). Beta-eudesmol has also been identified in Cannabis sativa extracts (PMID: 6991645, 26657499). (2R,4AR,8as)-decahydro-8-methylene-alpha,alpha,4a-trimethyl-2-naphthylmethanol beta-Selinenol (2R,4AR,8as)-decahydro-8-methylene-a,a,4a-trimethyl-2-naphthylmethanol (2R,4AR,8as)-decahydro-8-methylene-α,α,4a-trimethyl-2-naphthylmethanol b-Selinenol Β-selinenol b-Eudesmol Β-eudesmol beta-Eudesmol, (2S-(2alpha,4aalpha,8abeta))-isomer Eudesm-4(14)-en-11-ol (+)-beta-Eudesmol (+)-β-Eudesmol beta-Eudesmol C15H26O 222.37 222.1984 2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-decahydronaphthalen-2-yl]propan-2-ol β-eudesmol 473-15-4 CC(C)(O)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1 InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12-13,16H,1,5-10H2,2-4H3/t12-,13+,15-/m1/s1 BOPIMTNSYWYZOC-VNHYZAJKSA-N belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol Eudesmanes carbobicyclic compound eudesmane sesquiterpenoid tertiary alcohol logp 4.21 ALOGPS logs -4.49 ALOGPS logp 3.53 ChemAxon pka_strongest_acidic 19.32 ChemAxon pka_strongest_basic -0.91 ChemAxon iupac 2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-decahydronaphthalen-2-yl]propan-2-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)(O)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2C1 ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12-13,16H,1,5-10H2,2-4H3/t12-,13+,15-/m1/s1 ChemAxon inchikey BOPIMTNSYWYZOC-VNHYZAJKSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 68.36 ChemAxon polarizability 27.56 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003839 91457 C09664 10417 C00000164 CPD-11432 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, Tanaka Y, Misawa N, Utsumi R: Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. FEBS Lett. 2008 Mar 5;582(5):565-72. doi: 10.1016/j.febslet.2008.01.020. Epub 2008 Jan 31. 18242187 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:38:08 UTC 2020-07-29 16:16:12 UTC CDB000461 Gamma-Eudesmol Gamma-Eudesmol, also known as machilol or selinenol, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Gamma-Eudesmol is one of the terpenes and noncannabinoid chemical constituents identified in cannabis sativa plants (0.01 -0.46 mg/g) (PMID: 6991645; DOI: 10.1089/can.2016.0017). It was also identified in agarwood oil (1.40% to 10.30% relative to total oil components), the essential oil of Salvia microphylla (baby sage, Graham's sage, or blackcurrant sage) leaves (7.64% relative to total oil components) (DOI: 10.1007/s11746-011-1938-1), the essential oil of Alphonsea tonkinensis (Annonaceae) (5.5% relative to total oil components), the essential oil of Amyris balsamifera (balsam torchwood) (12.3% relative to total oil components) (DOI: 10.1007/s10600-015-1281-0), and the essential oil of Camellia nitidissima (fortune's yellow camellia) (31.5% relative to total oil components) (DOI: 10.1007/s10600-015-1281-0). (+)-gamma-Eudesmol Machilol Selinenol Uncineol (+)-g-Eudesmol (+)-Γ-eudesmol g-Eudesmol Γ-eudesmol C15H26O 222.37 222.1984 2-[(2R,4aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]propan-2-ol gamma-eudesmol 1209-71-8 CC1=C2C[C@@H](CC[C@@]2(C)CCC1)C(C)(C)O InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12,16H,5-10H2,1-4H3/t12-,15-/m1/s1 WMOPMQRJLLIEJV-IUODEOHRSA-N belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Tertiary alcohol Eudesmanes eudesmane sesquiterpenoid logp 4.55 ALOGPS logs -3.43 ALOGPS logp 3.43 ChemAxon pka_strongest_acidic 19.35 ChemAxon pka_strongest_basic -0.9 ChemAxon iupac 2-[(2R,4aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]propan-2-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC1=C2C[C@@H](CC[C@@]2(C)CCC1)C(C)(C)O ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h12,16H,5-10H2,1-4H3/t12-,15-/m1/s1 ChemAxon inchikey WMOPMQRJLLIEJV-IUODEOHRSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 69.17 ChemAxon polarizability 27.54 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C17124 62513 6432005 C00000165 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:38:11 UTC 2020-09-11 20:08:28 UTC CDB000462 Borneol Borneol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Borneol is a secondary alcohol and there are two enantiomers of borneol, d-(+)-borneol and l-(‚Äì)-borneol, which can be found in nature. Borneol is a component of many essential oils and it is a natural insect repellent. Additionally, borneol is one of many terpenoids that are known to occur in cannabis plants (PMID: 6991645). Borneol can be found in several species of Heterotheca, Artemisia, Callicarpa, Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga (https://doi.org/10.1002/ffj.2730070506). (1R,2S,4R)-(+)-Borneol (1R,2S,4R)-Borneol (1R-endo)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol Borneocamphor D-Borneol endo-2-Bornanol Sumatra camphor Borneol Isoborneol Isoborneol, (1R-endo)-isomer Isoborneol, (1R-exo)-isomer Isoborneol, (1S-endo)-isomer Isoborneol, (1S-exo)-isomer Isoborneol, (endo)-isomer Isoborneol, (endo-(+-))-isomer Isoborneol, (exo)-isomer (+)-(2S)-Borneol (+)-2-Borneol (+)-Borneol (+)-endo-Borneol (1R)-(+)-Borneol (1R)-endo-Borneol (1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol d-(+)-Borneol (±)-Borneol 2-Borneol 2-endo-Bornyl alcohol dl-Borneol endo-(±)-Bornan-2-ol endo-2-Hydroxy-1,7,7-trimethylnorbornane endo-Borneol Camphol C10H18O 154.25 154.1358 (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (+)-borneol 464-43-7 CC1(C)[C@@H]2CC[C@@]1(C)[C@@H](O)C2 InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1 DTGKSKDOIYIVQL-WEDXCCLWSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Bornane monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol borneol melting_point 208 °C Wikipedia boiling_point 213 °C Wikipedia logp 2.83 ALOGPS logs -2.28 ALOGPS logp 1.99 ChemAxon pka_strongest_acidic 19.6 ChemAxon pka_strongest_basic -0.78 ChemAxon iupac (1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@@H]2CC[C@@]1(C)[C@@H](O)C2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1 ChemAxon inchikey DTGKSKDOIYIVQL-WEDXCCLWSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.31 ChemAxon polarizability 18.47 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6552009 15393 C00011023 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:38:17 UTC 2020-07-07 15:58:38 UTC CDB000464 Gamma-Curcumene Gamma-Curcumene, also known as curcumene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406) Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Gamma-Curcumene is one of the terpenes found in Cannabis sativa (PMID: 6991645). It has also been identified in the essential oil of Lantana camara (west Indian lantana) (7.5% relative to total oil composition) (PMID: 20645797), Valeriana wallichii (Indian Valerian) (10.7% relative to total volatile composition) and helichrysum essential oil (13.9% relative to total oil components) (DOI: 10.1016/j.biopen.2017.04.001). g-Curcumene Γ-curcumene C15H24 204.36 204.1878 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene gamma-curcumene C[C@H](CCC=C(C)C)C1=CC=C(C)CC1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14H,5,7,9,11H2,1-4H3/t14-/m1/s1 NGIVKZGKEPRIGG-CQSZACIVSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon alicyclic compound sesquiterpene logp 6.07 ALOGPS logs -3.96 ALOGPS logp 4.82 ChemAxon iupac 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H](CCC=C(C)C)C1=CC=C(C)CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14H,5,7,9,11H2,1-4H3/t14-/m1/s1 ChemAxon inchikey NGIVKZGKEPRIGG-CQSZACIVSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.36 ChemAxon polarizability 26.41 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20179 63696 12304273 CPD-11393 C00030346 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Kurade NP, Jaitak V, Kaul VK, Sharma OP: Chemical composition and antibacterial activity of essential oils of Lantana camara, Ageratum houstonianum and Eupatorium adenophorum. Pharm Biol. 2010 May;48(5):539-44. doi: 10.3109/13880200903193336. 20645797 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:38:21 UTC 2020-08-04 22:28:19 UTC CDB000465 Cis-gamma-Bisabolene Cis-gamma-Bisabolene is an isomer of Bisabolene. Three isomers are known, Œ±-, Œ≤-, and Œ≥-bisabolene, which differ by the positions of the double bonds. Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406) Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322), and of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645, 26657499). Cis-gamma-Bisabolene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/f11030290). (Z)-Laquo gammaraquo -bisabolene (e)-g-Bisabolene (e)-Γ-bisabolene C15H24 204.35 204.1878 (4E)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene (E)-gamma-bisabolene 13062-00-5 CC(C)=CCC\C(C)=C1/CCC(C)=CC1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14- XBGUIVFBMBVUEG-PFONDFGASA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bisabolane sesquiterpenoids gamma-bisabolene logp 5.88 ALOGPS logs -3.55 ALOGPS logp 4.78 ChemAxon iupac (4E)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC\C(C)=C1/CCC(C)=CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14- ChemAxon inchikey XBGUIVFBMBVUEG-PFONDFGASA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.09 ChemAxon polarizability 26.87 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015018 4509327 5352437 49239 C19748 C00011631 CPD-8737 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Singh O, Khanam Z, Misra N, Srivastava MK: Chamomile (Matricaria chamomilla L.): An overview. Pharmacogn Rev. 2011 Jan;5(9):82-95. doi: 10.4103/0973-7847.79103. 22096322 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. 31659569 1.0 2020-03-19 00:38:26 UTC 2020-08-04 22:28:19 UTC CDB000466 Epi-Alpha-Bisabolol Epi-Alpha-Bisabolol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406) Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Epi-Alpha-Bisabolol is an isomer of Bisabolol. Bisabolol or more formally Œ±-(‚àí)-bisabolol is a colorless viscous oil. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322), and of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645, 26657499). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/f11030290). Bisabolol has a weak sweet floral aroma and is used in various fragrances. (2S)-6-Methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol (+)-Epi-a-bisabolol (+)-Epi-α-bisabolol C15H26O 222.37 222.1984 (2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol (2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol 515-69-5 CC(C)=CCC[C@](C)(O)[C@@H]1CCC(C)=CC1 InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15-/m0/s1 RGZSQWQPBWRIAQ-GJZGRUSLSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Bisabolane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol sesquiterpenoid logp 4.76 ALOGPS logs -3.48 ALOGPS logp 3.91 ChemAxon pka_strongest_basic -0.47 ChemAxon iupac (2S)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)=CCC[C@](C)(O)[C@@H]1CCC(C)=CC1 ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15-/m0/s1 ChemAxon inchikey RGZSQWQPBWRIAQ-GJZGRUSLSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 72.19 ChemAxon polarizability 28.3 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20479 68658 1201551 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Singh O, Khanam Z, Misra N, Srivastava MK: Chamomile (Matricaria chamomilla L.): An overview. Pharmacogn Rev. 2011 Jan;5(9):82-95. doi: 10.4103/0973-7847.79103. 22096322 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Yang CY, Seo MH, Lee SC: Male-Produced Aggregation Pheromone of the Sloe Bug, Dolycoris baccarum L. (Hemiptera: Heteroptera: Pentatomidae). J Chem Ecol. 2019 Oct;45(10):818-822. doi: 10.1007/s10886-019-01110-3. Epub 2019 Oct 28. 31659569 1.0 2020-03-19 00:38:29 UTC 2020-08-04 22:28:19 UTC CDB000467 (S)-Ipsdienol Ipsdienol or S-ipsdienol belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. S-ipsdienol is considered to be an isoprenoid lipid molecule. S-ipsdienol is a secondary alcohol and it is very hydrophobic, practically insoluble in water but soluble in organic solvents such as methanol, ethanol and ethyl acetate. Ipsdienol was first identified from the bark beetle Ips confusus, in which it is believed to be a main sex attractant (DOI: 10.1126/science.154.3748.509). It is also one of the major aggregation pheromones of the bark beetle (PMID: 20727970). Ipsdienol has also been identified in a number of plant species, including Cannabis sativa (PMID: 8984153). Ipsdienol 2-Methyl-6-methylene-2,7-octadien-4-ol C10H16O 152.24 152.1201 (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol 13040-13-6 CC(C)=C[C@@H](O)CC(=C)C=C InChI=1S/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5-6,10-11H,1,4,7H2,2-3H3/t10-/m1/s1 NHMKYUHMPXBMFI-SNVBAGLBSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Secondary alcohols Acyclic monoterpenoid Alcohol Aliphatic acyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol Acyclic monoterpenoids logp 2.56 ALOGPS logs -2.23 ALOGPS logp 2.31 ChemAxon pka_strongest_acidic 18.33 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol ChemAxon average_mass 152.24 ChemAxon mono_mass 152.1201 ChemAxon smiles CC(C)=C[C@@H](O)CC(=C)C=C ChemAxon formula C10H16O ChemAxon inchi InChI=1S/C10H16O/c1-5-9(4)7-10(11)6-8(2)3/h5-6,10-11H,1,4,7H2,2-3H3/t10-/m1/s1 ChemAxon inchikey NHMKYUHMPXBMFI-SNVBAGLBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 49.89 ChemAxon polarizability 18.37 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 92301 (S)-Ipsdienol Blomquist GJ, Figueroa-Teran R, Aw M, Song M, Gorzalski A, Abbott NL, Chang E, Tittiger C: Pheromone production in bark beetles. Insect Biochem Mol Biol. 2010 Oct;40(10):699-712. doi: 10.1016/j.ibmb.2010.07.013. Epub 2010 Aug 19. 20727970 Ross SA, ElSohly MA: The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J Nat Prod. 1996 Jan;59(1):49-51. doi: 10.1021/np960004a. 8984153 1.0 2020-03-19 00:38:33 UTC 2020-09-11 20:08:29 UTC CDB000468 alpha-Ylangene Alpha-Ylangene also known as Ylangene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Ylangene is a pale-yellow clear liquid. Alpha-Ylangene is a naturally occurring sesquiterpene found in the leaves of cashew tree (DOI:10.12691/wjac-3-1-2), in grapes (PMID: 17580875), and in Cannabis sativa (PMID: 30596146). C15H24 204.36 204.1878 (1S,2R,6R,7R,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene (1S,2R,6R,7R,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene 14912-44-8 CC(C)[C@@H]1CC[C@@]2(C)[C@@H]3CC=C(C)[C@H]2[C@H]13 InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12+,13+,14-,15-/m0/s1 VLXDPFLIRFYIME-QRTUWBSPSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Copaane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 3.75 ALOGPS logs -5.05 ALOGPS logp 4.09 ChemAxon iupac (1S,2R,6R,7R,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@@H]1CC[C@@]2(C)[C@@H]3CC=C(C)[C@H]2[C@H]13 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12+,13+,14-,15-/m0/s1 ChemAxon inchikey VLXDPFLIRFYIME-QRTUWBSPSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.77 ChemAxon polarizability 26.11 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 20055075 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Parker M, Pollnitz AP, Cozzolino D, Francis IL, Herderich MJ: Identification and quantification of a marker compound for 'pepper' aroma and flavor in shiraz grape berries by combination of chemometrics and gas chromatography-mass spectrometry. J Agric Food Chem. 2007 Jul 25;55(15):5948-55. doi: 10.1021/jf0705320. Epub 2007 Jun 20. 17580875 Gallily R, Yekhtin Z, Hanus LO: The Anti-Inflammatory Properties of Terpenoids from Cannabis. Cannabis Cannabinoid Res. 2018 Dec 26;3(1):282-290. doi: 10.1089/can.2018.0014. eCollection 2018. 30596146 1.0 2020-03-19 00:38:36 UTC 2020-07-07 15:58:41 UTC CDB000469 Beta-Elemene Beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Elemenes are a group of closely related natural chemical compounds found in a variety of plants, with Beta-Elemene being one of the 4 isomers of Elemene. The elemenes contribute to the floral aromas of some plants and are a part of the composition of Cannabis sativa (PMID: 6991645). (1S,2S,4R)-(-)-1-Methyl-1-vinyl-2,4-diisopropenylcyclohexane (1S,2S,4R)-1-Methyl-2,4-di(prop-1-en-2-yl)-1-vinylcyclohexane (1S,2S,4R)-2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane 2,4-Diisopropenyl-1-methyl-1-vinylcyclohexane beta-Elemen Levo-beta-elemene b-Elemen Β-elemen Levo-b-elemene Levo-β-elemene b-Elemene Β-elemene (-)-b-Elemene (-)-beta-Elemene beta-Elemene (-)-β-Elemene (1S,2S,4R)-1-Ethenyl-1-methyl-2,4-bis(1-methylethenyl)cyclohexane (±)-beta-Elemene (±)-β-Elemene C15H24 204.35 204.1878 (1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane β-elemene 515-13-9 CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1 OPFTUNCRGUEPRZ-QLFBSQMISA-N belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Elemane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Elemane sesquiterpenoid Hydrocarbon Olefin Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon beta-elemene logp 5.40 ALOGPS logs -4.71 ALOGPS logp 4.74 ChemAxon iupac (1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1 ChemAxon inchikey OPFTUNCRGUEPRZ-QLFBSQMISA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.23 ChemAxon polarizability 25.97 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014577 5293588 6918391 62855 C17094 C00007453 CPD-8232 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:38:40 UTC 2020-08-04 22:28:19 UTC CDB000470 alpha-cis-Bergamotene Œ±-cis-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. It is a naturally occurring sesquiterpene found in the essential oils of plants such as tobacco (PMID:28434859) and cannabis (PMID:6991645). It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it is synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are four known Bergamotene isomers including Œ±-cis-, Œ±-trans-, Œ≤-cis- and Œ≤-trans-bergamotene. Œ±-cis-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat. Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295). Œ±-Bergamotene has also been detected in the volatile fraction of Cannabis sativa samples (PMID: 26657499). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). (e)-a-Bergamotene (e)-Α-bergamotene C15H24 204.35 204.1878 (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2 InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1 YMBFCQPIMVLNIU-KFWWJZLASA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Pinane monoterpenoid Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.91 ALOGPS logs -4.48 ALOGPS logp 4.46 ChemAxon iupac (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1 ChemAxon inchikey YMBFCQPIMVLNIU-KFWWJZLASA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.52 ChemAxon polarizability 26.58 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003887 13889654 Zhou W, Kugler A, McGale E, Haverkamp A, Knaden M, Guo H, Beran F, Yon F, Li R, Lackus N, Kollner TG, Bing J, Schuman MC, Hansson BS, Kessler D, Baldwin IT, Xu S: Tissue-Specific Emission of (E)-alpha-Bergamotene Helps Resolve the Dilemma When Pollinators Are Also Herbivores. Curr Biol. 2017 May 8;27(9):1336-1341. doi: 10.1016/j.cub.2017.03.017. Epub 2017 Apr 20. 28434859 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schnee C, Kollner TG, Held M, Turlings TC, Gershenzon J, Degenhardt J: The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc Natl Acad Sci U S A. 2006 Jan 24;103(4):1129-34. doi: 10.1073/pnas.0508027103. Epub 2006 Jan 17. 16418295 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:38:43 UTC 2020-09-11 20:08:30 UTC CDB000471 Gamma-Muurolene Gamma-Muurolene, also known as muurolene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. These are terpenes with three consecutive isoprene units. Gamma-muurolene is possibly neutral and it is one of the terpenes found in the essential oils of the different hemp variaties (DOI: 10.1007/978-1-59259-947-9_2). It was also identified in the essential oil of Artemisia pedemontana (Dwarf Wormwood) (1.6% relative to total volatile compounds) (DOI: 10.1016/S0305-1978(02)00082-0), the seed pod resin of Hymenaea courbaril (stinkingtoe) (DOI: 10.1016/j.jep.2017.05.024), the essential oil from Ocimum gratissimum (clove basil) leaves (11.6% relative to total oil compounds) (PMID: 29578062), the essential oil from Cleome droserifolia (spider flower) (4.10% relative to the total oil components) (PMID: 30253077). (1S,4AS,8ar)-1-isopropyl-7-methyl-4-methylene-1,2,3,4,4a,5,6,8a-octahydronaphthalene (+)-gamma-Muurolene (+)-g-Muurolene (+)-Γ-muurolene g-Muurolene Γ-muurolene C15H24 204.36 204.1878 (1S,4aS,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (4S,4aR,8aS)-4-isopropyl-6-methyl-1-methylidene-3,4,4a,7,8,8a-hexahydro-2H-naphthalene CC(C)[C@@H]1CCC(=C)[C@H]2CCC(C)=C[C@@H]12 InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14+,15-/m0/s1 WRHGORWNJGOVQY-ZNMIVQPWSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cadinane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon carbobicyclic compound sesquiterpene logp 4.48 ALOGPS logs -4.54 ALOGPS logp 4.51 ChemAxon iupac (1S,4aS,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@@H]1CCC(=C)[C@H]2CCC(C)=C[C@@H]12 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14+,15-/m0/s1 ChemAxon inchikey WRHGORWNJGOVQY-ZNMIVQPWSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.53 ChemAxon polarizability 26.2 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C20273 64798 12313020 CPD-8791 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Chimnoi N, Reuk-Ngam N, Chuysinuan P, Khlaychan P, Khunnawutmanotham N, Chokchaichamnankit D, Thamniyom W, Klayraung S, Mahidol C, Techasakul S: Characterization of essential oil from Ocimum gratissimum leaves: Antibacterial and mode of action against selected gastroenteritis pathogens. Microb Pathog. 2018 May;118:290-300. doi: 10.1016/j.micpath.2018.03.041. Epub 2018 Mar 22. 29578062 Abd El-Gawad AM, El-Amier YA, Bonanomi G: Essential Oil Composition, Antioxidant and Allelopathic Activities of Cleome droserifolia (Forssk.) Delile. Chem Biodivers. 2018 Dec;15(12):e1800392. doi: 10.1002/cbdv.201800392. Epub 2018 Nov 27. 30253077 1.0 2020-03-19 00:38:47 UTC 2020-08-04 22:28:19 UTC CDB000472 alpha-Cadinene Alpha-Cadinene, also known as Cadinene, belongs to the class of organic compounds known as sesquiterpenoids. Alpha-cadinene is a naturally occurring sesquiterpene found in trace amounts in cannabis plants (PMID: 6991645). Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Cadinene is possibly neutral. Alpha-Cadinene is a colorless liquid with a woody dry odor. It is one of the four isomers of Cadinene including Œ≤-Cadinene, Œ≥-Cadinene and Œ¥-Cadinene. Cadinene is the trivial chemical name of a number of isomeric hydrocarbons that occur in a wide variety of essential oil-producing plants. a-Cadinene Α-cadinene (-)-a-Cadinene 1,2,4a,5,6,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)-(1S,4ar,8ar)-naphthalene Cadina-4,9-diene, (-)- (8ci) C15H24 204.35 204.1878 (1S,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene (4S,4aR,8aR)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydronaphthalene 24406-05-1 CC(C)[C@@H]1CC=C(C)[C@@H]2CCC(C)=C[C@@H]12 InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h6,9-10,13-15H,5,7-8H2,1-4H3/t13-,14-,15-/m0/s1 QMAYBMKBYCGXDH-KKUMJFAQSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cadinane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cadinane sesquiterpenoids sesquiterpenoid logp 5.00 ALOGPS logs -4.30 ALOGPS logp 4.45 ChemAxon iupac (1S,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,6,8a-hexahydronaphthalene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@@H]1CC=C(C)[C@@H]2CCC(C)=C[C@@H]12 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h6,9-10,13-15H,5,7-8H2,1-4H3/t13-,14-,15-/m0/s1 ChemAxon inchikey QMAYBMKBYCGXDH-KKUMJFAQSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.6 ChemAxon polarizability 26.5 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB017447 16737087 12306048 C00020051 C16815 80749 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:38:49 UTC 2020-08-04 22:28:19 UTC CDB000473 alpha-Longipinene Œ±-Longipinene belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ±-Longipinene is a naturally occurring sesquiterpene found in Norway spruce (PMID: 15310829). Œ±-Longipinene has been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645; PMID: 26657499). alpha-Longipinene a-Longipinene Α-longipinene (-)-a-Longipinene (-)-Α-longipinene C15H24 204.36 204.1878 (1S,2R,7S,8S)-2,6,6,9-tetramethyltricyclo[5.4.0.0^{2,8}]undec-9-ene (1S,2R,7S,8S)-2,6,6,9-tetramethyltricyclo[5.4.0.0^{2,8}]undec-9-ene CC1=CC[C@H]2[C@H]3[C@@H]1[C@]2(C)CCCC3(C)C InChI=1S/C15H24/c1-10-6-7-11-13-12(10)15(11,4)9-5-8-14(13,2)3/h6,11-13H,5,7-9H2,1-4H3/t11-,12+,13-,15+/m0/s1 HICYDYJTCDBHMZ-SFDCQRBFSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Longipinane sesquiterpenoid Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon alpha-longipinene logp 4.14 ALOGPS logs -5.10 ALOGPS logp 4.1 ChemAxon iupac (1S,2R,7S,8S)-2,6,6,9-tetramethyltricyclo[5.4.0.0^{2,8}]undec-9-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC1=CC[C@H]2[C@H]3[C@@H]1[C@]2(C)CCCC3(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-6-7-11-13-12(10)15(11,4)9-5-8-14(13,2)3/h6,11-13H,5,7-9H2,1-4H3/t11-,12+,13-,15+/m0/s1 ChemAxon inchikey HICYDYJTCDBHMZ-SFDCQRBFSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.69 ChemAxon polarizability 25.84 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 62751 53356675 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Martin DM, Faldt J, Bohlmann J: Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily. Plant Physiol. 2004 Aug;135(4):1908-27. doi: 10.1104/pp.104.042028. Epub 2004 Aug 13. 15310829 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:38:51 UTC 2020-09-11 20:08:27 UTC CDB000474 Caryophyllene oxide Caryophyllene oxide, an oxidation product of caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Caryophyllene oxide is neutral compound, a pale yellow white crystalline solid with a sweet, fresh, dry woody, spicy odor and an old wood, carrot, amber flavor ( http://www.thegoodscentscompany.com/data/rw1023631.html#tophyp). Caryophyllene oxide is one of the many sesquiterpenes found in cannabis plants and their essential oils. Caryophyllene oxide was isolated from cannabis plant ‚Äúdrug-type‚Äù with generally less caryophyllene oxide than ‚Äúfiber-type‚Äù (hemp) Cannabis (PMID: 6991645). Caryophyllene oxide is a volatile compound found in different species of citrus fruits (https://doi.org/10.1016/j.foodchem.2017.03.040). Almost 10% of caryophyllene oxide was detected in baccharis coridifolia oil from Argentina (9.80%) with 8.20%, found in guava leaf oil from Cuba, 5.10% in guava fruit oil from Reunion, 3.40% in curry wood leaf oil from Australia and 3.73% in lavender stem oil from Lithuania (http://www.thegoodscentscompany.com/data/rw1023631.html#tooccur). By contrast, caryophyllene oxide is one of the major compounds found in the essential oil of Salvia spinosa (63.0%). Salvia spinosa essential oil has antimicrobial, cytotoxicity, antioxidant and enzyme inhibitory activities (https://doi.org/10.1016/j.jff.2015.09.011). C15H24O 220.36 220.1827 (1S,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane (1S,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane 1139-30-6 C[C@@]12CC[C@H]3[C@@H](CC3(C)C)C(=C)CC[C@@H]1O2 InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m0/s1 NVEQFIOZRFFVFW-PWNZVWSESA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic heteropolycyclic compounds Dialkyl ethers Epoxides Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteropolycyclic compound Caryophyllane sesquiterpenoid Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Sesquiterpenoid logp 3.49 ALOGPS logs -4.50 ALOGPS logp 3.62 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (1S,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane ChemAxon average_mass 220.36 ChemAxon mono_mass 220.1827 ChemAxon smiles C[C@@]12CC[C@H]3[C@@H](CC3(C)C)C(=C)CC[C@@H]1O2 ChemAxon formula C15H24O ChemAxon inchi InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m0/s1 ChemAxon inchikey NVEQFIOZRFFVFW-PWNZVWSESA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 66.21 ChemAxon polarizability 26.5 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7067459 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-19 00:38:56 UTC 2020-06-29 20:41:02 UTC CDB000476 Isocannabispiran Iso-cannabispiran belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Iso-cannabispiran is formally classified as a phenol and it is one of thirty-four noncannabinoid phenols and one of the nine spiro-indan-type compounds that are found in cannabis plants (https://doi.org/10.1016/S0031-9422(00)81194-2). Spiro compounds are cyclic compounds that include two rings which share a single atom (usually a carbon). The simplest example of this type of compound is Spiro[2.2]pentane. The structure of Iso-cannabispiran is similar to Cannabispiran except the positions of hydroxy and methoxy groups on benzene ring. C15H18O3 246.31 246.1256 5'-hydroxy-7'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-one 5'-hydroxy-7'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-one COC1=CC(O)=CC2=C1C1(CC2)CCC(=O)CC1 InChI=1S/C15H18O3/c1-18-13-9-12(17)8-10-2-5-15(14(10)13)6-3-11(16)4-7-15/h8-9,17H,2-7H2,1H3 ZKJMXTKGSQHXEC-UHFFFAOYSA-N belongs to the class of organic compounds known as indan-1-spirocyclohexanes. These are organic aromatic compounds containing a cyclohexane moiety linked to the 1-position of an indane moiety in a spiro configuration. Indan-1-spirocyclohexanes Organic compounds Benzenoids Indanes Indan-1-spirocyclohexanes Aromatic homopolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Cyclic ketones Hydrocarbon derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homopolycyclic compound Carbonyl group Cyclic ketone Ether Hydrocarbon derivative Indan-1-spirocyclohexane Ketone Organic oxide Organic oxygen compound Organooxygen compound logp 2.70 ALOGPS logs -3.57 ALOGPS logp 2.8 ChemAxon pka_strongest_acidic 9.55 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 5'-hydroxy-7'-methoxy-2',3'-dihydrospiro[cyclohexane-1,1'-indene]-4-one ChemAxon average_mass 246.31 ChemAxon mono_mass 246.1256 ChemAxon smiles COC1=CC(O)=CC2=C1C1(CC2)CCC(=O)CC1 ChemAxon formula C15H18O3 ChemAxon inchi InChI=1S/C15H18O3/c1-18-13-9-12(17)8-10-2-5-15(14(10)13)6-3-11(16)4-7-15/h8-9,17H,2-7H2,1H3 ChemAxon inchikey ZKJMXTKGSQHXEC-UHFFFAOYSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 69.05 ChemAxon polarizability 26.79 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-19 00:39:02 UTC 2020-07-24 23:30:07 UTC CDB000477 Cannabistilbene I Cannabistilbene I, also known as DMMBD, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Cannabistilbene I holds two hydroxyl groups (one is methylated) in ring A, both in a meta arrangement in relation to the C2 moiety. Ring B holds one hydroxyl group in para position and is prenylated in the meta position. Cannabistilbene I is a new dihydrostilbene and was obtained as a light oil. Cannabis stilbenoids were first detected and isolated from leaves in 1978, from stem in 1982, and from resin in 1986 (https://doi.org/10.1007/s11101-008-9094-4). Cannabis stilbenoids exhibit antibacterial, anti-inflammatory, antioxidant activities. Cannabistilbene I is one of several non-cannabinoid phenolic compounds that are known to occur in the Cannabis plants (PMID: 28799497). 3,4'-Dihydroxy-5-methoxy-3'-(3-methylbut-2-enyl)dihydrostilbene DMMBD C20H24O3 312.41 312.1725 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-(3-methylbut-2-en-1-yl)phenol 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-(3-methylbut-2-en-1-yl)phenol 91925-76-7 COC1=CC(CCC2=CC(CC=C(C)C)=C(O)C=C2)=CC(O)=C1 InChI=1S/C20H24O3/c1-14(2)4-8-17-10-15(7-9-20(17)22)5-6-16-11-18(21)13-19(12-16)23-3/h4,7,9-13,21-22H,5-6,8H2,1-3H3 PPIQDICARGCSMB-UHFFFAOYSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenol ether Phenoxy compound Stilbene logp 4.73 ALOGPS logs -5.08 ALOGPS logp 5.47 ChemAxon pka_strongest_acidic 9.29 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-(3-methylbut-2-en-1-yl)phenol ChemAxon average_mass 312.41 ChemAxon mono_mass 312.1725 ChemAxon smiles COC1=CC(CCC2=CC(CC=C(C)C)=C(O)C=C2)=CC(O)=C1 ChemAxon formula C20H24O3 ChemAxon inchi InChI=1S/C20H24O3/c1-14(2)4-8-17-10-15(7-9-20(17)22)5-6-16-11-18(21)13-19(12-16)23-3/h4,7,9-13,21-22H,5-6,8H2,1-3H3 ChemAxon inchikey PPIQDICARGCSMB-UHFFFAOYSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 95.06 ChemAxon polarizability 36.37 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 146349 Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. 28799497 1.0 2020-03-19 00:39:07 UTC 2020-07-24 23:30:19 UTC CDB000478 Cannabistilbene II Cannabistilbene II belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Cannabistilbene II is one of the dihydrostilbenes and non-cannabinoid phenolic compounds that have been identified in cannabis plants (PMID: 28799497). It was obtained as a colorless oil from cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). There are two known Cannabistilbene II isomers including Cannabistilbene IIa and Cannabistilbene IIb. Cannabis stilbenoids were first detected and isolated from leaves in 1978, from stem in 1982, and from resin in 1986 (https://doi.org/10.1007/s11101-008-9094-4). Cannabis stilbenoids exhibit antibacterial, anti-inflammatory, antioxidant activities. Cannabistilbene I is one of several non-cannabinoid phenolic compounds that are known to occur in the Cannabis plants (PMID: 28799497). C17H20O5 304.34 304.1311 3-{2-[(1S)-5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl]ethenyl}-2,6-dimethoxyphenol 3-{2-[(1S)-5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl]ethenyl}-2,6-dimethoxyphenol 91865-42-8 COC1=C[C@@H](CC(O)=C1)C=CC1=C(OC)C(O)=C(OC)C=C1 InChI=1S/C17H20O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)16(19)17(12)22-3/h4-7,9-11,18-19H,8H2,1-3H3/t11-/m1/s1 LIAAUPRCZCWDAE-LLVKDONJSA-N logp 2.32 ALOGPS logs -3.81 ALOGPS logp 1.97 ChemAxon pka_strongest_acidic 8.48 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 3-{2-[(1S)-5-hydroxy-3-methoxycyclohexa-2,4-dien-1-yl]ethenyl}-2,6-dimethoxyphenol ChemAxon average_mass 304.34 ChemAxon mono_mass 304.1311 ChemAxon smiles COC1=C[C@@H](CC(O)=C1)C=CC1=C(OC)C(O)=C(OC)C=C1 ChemAxon formula C17H20O5 ChemAxon inchi InChI=1S/C17H20O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)16(19)17(12)22-3/h4-7,9-11,18-19H,8H2,1-3H3/t11-/m1/s1 ChemAxon inchikey LIAAUPRCZCWDAE-LLVKDONJSA-N ChemAxon polar_surface_area 68.15 ChemAxon refractivity 88.4 ChemAxon polarizability 32.14 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Pollastro F, Minassi A, Fresu LG: Cannabis Phenolics and their Bioactivities. Curr Med Chem. 2018;25(10):1160-1185. doi: 10.2174/0929867324666170810164636. 28799497 1.0 2020-03-19 00:39:10 UTC 2020-08-04 22:28:20 UTC CDB000479 (-)-Aristolene Aristolene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406).. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton. Aristolene is possibly neutral. It has been identified in cannabis (PMID: 26657499), the essential oil from Pelargonium graveolens (rose geranium) (13.19% relative to total oil constituents) (PMID: 26854645), the essential oil from Ferula communis (giant fennel) leaf (8.5% relative to total oil constituents) (DOI: 10.1002/ffj.1405), and the dry fruit essential oil from Vitex negundo (Chinese chaste tree) (8% relative to total oil constituents) (PMID: 20046787). C15H24 204.36 204.1878 (1aS,7S,7aS,7bS)-1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene (1aS,7S,7aS,7bS)-1,1,7,7a-tetramethyl-1aH,2H,4H,5H,6H,7H,7bH-cyclopropa[a]naphthalene 6831-16-9 C[C@H]1CCCC2=CC[C@H]3[C@@H](C3(C)C)[C@]12C InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3/t10-,12-,13-,15+/m0/s1 FOBXOZMHEKILEY-GZCFXPHUSA-N logp 4.65 ALOGPS logs -5.06 ALOGPS logp 4.1 ChemAxon iupac (1aS,7S,7aS,7bS)-1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H]1CCCC2=CC[C@H]3[C@@H](C3(C)C)[C@]12C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3/t10-,12-,13-,15+/m0/s1 ChemAxon inchikey FOBXOZMHEKILEY-GZCFXPHUSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.69 ChemAxon polarizability 25.91 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Juarez ZN, Bach H, Sanchez-Arreola E, Bach H, Hernandez LR: Protective antifungal activity of essential oils extracted from Buddleja perfoliata and Pelargonium graveolens against fungi isolated from stored grains. J Appl Microbiol. 2016 May;120(5):1264-70. doi: 10.1111/jam.13092. Epub 2016 Apr 4. 26854645 Khokra SL, Prakash O, Jain S, Aneja KR, Dhingra Y: Essential Oil Composition and Antibacterial Studies of Vitex negundo Linn. Extracts. Indian J Pharm Sci. 2008 Jul-Aug;70(4):522-6. doi: 10.4103/0250-474X.44610. 20046787 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:39:13 UTC 2020-07-24 23:30:19 UTC CDB000480 (-)-Globulol (-)-Globulol or Globulol belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406).. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Globulol has been identified in the essential oil from Eugenia uniflora L. (pitanga) (1.5-7.4% relative to total oil constituents) (PMID: 32092893), the essential oil of the fruits of Eucalyptus globulus (southern blue gum) (10.69% relative to total oil constituents) (PMID: 20727725), the essential oil from Hyptis mutabilis (tropical bushmint) (11.6%-26.6% relative to total oil constituents) (PMID: 24068193), the essential oil of the leaves of Lophostemon species (a genus of 4 species of evergreen tree in the myrtle family Myrtaceae native to Australia) (4.7%-15.9% relative to total oil constituents) (DOI: 10.1002/(SICI)1099-1026(200001/02)15:1<17::AID-FFJ859>3.0.CO;2-D), and also in cannabis inflorescence (0.06-0.1% relative to total terpenoids) (PMID: 32094454). It has been shown to have sedative, anesthetic activities (PMID: 24068193; DOI: 10.1111/raq.12245) and antimicrobial effects (PMID: 18569693). C15H26O 222.37 222.1984 (1aR,4S,4aS,7S,7aR,7bR)-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4-ol (1aR,4S,4aS,7S,7aR,7bR)-1,1,4,7-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4-ol 489-41-8 C[C@H]1CC[C@H]2[C@H]1[C@@H]1[C@@H](CC[C@]2(C)O)C1(C)C InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10-,11+,12-,13-,15-/m0/s1 AYXPYQRXGNDJFU-WBSYEDSCSA-N logp 3.15 ALOGPS logs -4.72 ALOGPS logp 3.18 ChemAxon pka_strongest_basic -0.51 ChemAxon iupac (1aR,4S,4aS,7S,7aR,7bR)-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles C[C@H]1CC[C@H]2[C@H]1[C@@H]1[C@@H](CC[C@]2(C)O)C1(C)C ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10-,11+,12-,13-,15-/m0/s1 ChemAxon inchikey AYXPYQRXGNDJFU-WBSYEDSCSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 66.6 ChemAxon polarizability 27.33 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon da Costa JS, Barroso AS, Mourao RHV, da Silva JKR, Maia JGS, Figueiredo PLB: Seasonal and Antioxidant Evaluation of Essential Oil from Eugenia uniflora L., Curzerene-Rich, Thermally Produced in Situ. Biomolecules. 2020 Feb 19;10(2). pii: biom10020328. doi: 10.3390/biom10020328. 32092893 Mulyaningsih S, Sporer F, Zimmermann S, Reichling J, Wink M: Synergistic properties of the terpenoids aromadendrene and 1,8-cineole from the essential oil of Eucalyptus globulus against antibiotic-susceptible and antibiotic-resistant pathogens. Phytomedicine. 2010 Nov;17(13):1061-6. doi: 10.1016/j.phymed.2010.06.018. Epub 2010 Aug 19. 20727725 Silva LL, Garlet QI, Benovit SC, Dolci G, Mallmann CA, Burger ME, Baldisserotto B, Longhi SJ, Heinzmann BM: Sedative and anesthetic activities of the essential oils of Hyptis mutabilis (Rich.) Briq. and their isolated components in silver catfish (Rhamdia quelen). Braz J Med Biol Res. 2013 Sep;46(9):771-9. doi: 10.1590/1414-431X20133013. Epub 2013 Sep 18. 24068193 Jin D, Dai K, Xie Z, Chen J: Secondary Metabolites Profiled in Cannabis Inflorescences, Leaves, Stem Barks, and Roots for Medicinal Purposes. Sci Rep. 2020 Feb 24;10(1):3309. doi: 10.1038/s41598-020-60172-6. 32094454 Tan M, Zhou L, Huang Y, Wang Y, Hao X, Wang J: Antimicrobial activity of globulol isolated from the fruits of Eucalyptus globulus Labill. Nat Prod Res. 2008 May 10;22(7):569-75. doi: 10.1080/14786410701592745. 18569693 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:39:20 UTC 2020-08-04 22:28:20 UTC CDB000482 (+)-calarene (+)-Calarene or Calarene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6, C11 cyclization of the bicyclic eremophilane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. It was identified in the essential oil of leaves of Rhododendron aureum (rosebay) (10.4% - 66.4% relative to total oil constituents) (DOI: 10.2298/JSC1002209O), the essential oil from Valeriana jatamansi Jones (Indian valerian or Tagar) (DOI: 10.1080/10412905.2013.767757), the essential oil from Humulus lupulus (hop) (PMID: 24152289), the essential oil of Piper sarmentosum (wild pepper) (0.81%) (DOI: 10.1016/S2095-3119(17)61693-9), agarwood oil (24.7% relative to total volatile compounds), spikenard (PMID: 18404340), and cannabis (PMID: 26657499). It has been shown to have a sedative effect (PMID: 18404340). C15H24 204.36 204.1878 (1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene (1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1aH,2H,3H,5H,6H,7H,7bH-cyclopropa[a]naphthalene C[C@H]1CCC=C2CC[C@@H]3[C@H](C3(C)C)[C@]12C InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h7,10,12-13H,5-6,8-9H2,1-4H3/t10-,12+,13+,15+/m0/s1 MBIPADCEHSKJDQ-XTWPYSKKSA-N logp 4.58 ALOGPS logs -5.05 ALOGPS logp 4.1 ChemAxon iupac (1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H]1CCC=C2CC[C@@H]3[C@H](C3(C)C)[C@]12C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h7,10,12-13H,5-6,8-9H2,1-4H3/t10-,12+,13+,15+/m0/s1 ChemAxon inchikey MBIPADCEHSKJDQ-XTWPYSKKSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.69 ChemAxon polarizability 25.86 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Van Opstaele F, Praet T, Aerts G, De Cooman L: Characterization of novel single-variety oxygenated sesquiterpenoid hop oil fractions via headspace solid-phase microextraction and gas chromatography-mass spectrometry/olfactometry. J Agric Food Chem. 2013 Nov 6;61(44):10555-64. doi: 10.1021/jf402496t. Epub 2013 Oct 23. 24152289 Takemoto H, Ito M, Shiraki T, Yagura T, Honda G: Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components. J Nat Med. 2008 Jan;62(1):41-6. doi: 10.1007/s11418-007-0177-0. Epub 2007 Aug 23. 18404340 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:39:25 UTC 2020-08-04 22:28:20 UTC CDB000483 (+)-nerolidol Nerolidol also known as peruviol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Nerolidol is a naturally occurring sesquiterpene alcohol found in the essential oils of many types of plants and flowers. It is present in neroli, ginger, jasmine, lavender, tea tree, and lemon grass, and is a dominant scent compound in Brassavola nodosa. Nerolidol has also been reported as one of the volatile components detected in cannabis samples (PMID: 26657499). The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520). Currently it is also under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs (https://doi.org/10.1016/S0939-6411(01)00166-7). Additionally, it is known for various biological activities include antioxidant, anti-fungal, anticancer, and antimicrobial activity (PMID: 27136520). (+)-cis-Nerolidol (+)-Nerolidol (6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol (Z)-(S)-(+)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol (Z)-Nerolidol 3,7,11-Trimethyl-(3S,6Z)-(+)-1,6,10-dodecatrien-3-ol 3,7,11-Trimethyl-(Z)-(S)-(+)-1,6,10-dodecatrien-3-ol D-Nerolidol 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol Nerolidol, (Z)-isomer Nerolidol, (S-(Z))-isomer Nerolidol Nerolidol, (e)-isomer Nerolidol, (S-(e))-isomer Peruviol [S-(Z)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol (3S,6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol folic alcohol cis-(+)-Nerolidol (3S,6Z)-Nerolidol (±)-Nerolidol Nerodilol C15H26O 222.37 222.1984 (3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol (3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol 142-50-7 CC(C)=CCC\C(C)=C/CC[C@](C)(O)C=C InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-/t15-/m1/s1 FQTLCLSUCSAZDY-QKXCFHHRSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic acyclic compounds Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic acyclic compound Farsesane sesquiterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Sesquiterpenoid Tertiary alcohol logp 4.55 ALOGPS logs -4.02 ALOGPS logp 4.31 ChemAxon pka_strongest_acidic 18.46 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol ChemAxon average_mass 222.37 ChemAxon mono_mass 222.1984 ChemAxon smiles CC(C)=CCC\C(C)=C/CC[C@](C)(O)C=C ChemAxon formula C15H26O ChemAxon inchi InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-/t15-/m1/s1 ChemAxon inchikey FQTLCLSUCSAZDY-QKXCFHHRSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 74.01 ChemAxon polarizability 27.79 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006275 4512192 5356544 C00034757 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Chan WK, Tan LT, Chan KG, Lee LH, Goh BH: Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities. Molecules. 2016 Apr 28;21(5). pii: molecules21050529. doi: 10.3390/molecules21050529. 27136520 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:39:27 UTC 2020-08-04 22:28:20 UTC CDB000484 (+)-Sativene Sativene belongs to the class of organic compounds known as sesquiterpenoids. A sesquiterpene that is octahydro-1H-1,4-methanoindene bearing methyl, isopropyl and methylene substituents at positions 4, 7 and 8 respectively (the 1R,3aS,4R,7R,7aR-isomer). Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Sativene is possibly neutral and it is one of the terpenes that are known to occur in cannabis plants (PMID: 25454145). It was also identified in the essential oil from Kyllinga erecta Schumach (navua sedge) (DOI: 10.1021/jf00026a027), Croton sonderianus (marmeleiro preto) (PMID: 15979097), Stachys aleurites (Lamb's Ear) (0.2% relative to total oil constituents) (DOI: 10.1016/j.bse.2004.05.013), and the essential oil from fruits of Schinus terebinthifolia Raddi (Brazilian pepper tree) (0.93% relative to total oil constituents) (PMID: 21729280). (+)-Sativene (1R,3AS,4R,7R,7ar)-7-isopropyl-4-methyl-8-methyleneoctahydro-1H-1,4-methanoindene C15H24 204.36 204.1878 (1S,2R,3R,6R,8R)-6-methyl-7-methylidene-3-(propan-2-yl)tricyclo[4.4.0.0^{2,8}]decane (1S,2R,3R,6R,8R)-3-isopropyl-6-methyl-7-methylidenetricyclo[4.4.0.0^{2,8}]decane 3650-28-0 CC(C)[C@H]1CC[C@]2(C)[C@H]3CC[C@H]([C@@H]13)C2=C InChI=1S/C15H24/c1-9(2)11-7-8-15(4)10(3)12-5-6-13(15)14(11)12/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13+,14-,15+/m1/s1 VOBBUADSYROGAT-FQKPHLNHSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Oplopane sesquiterpenoid Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon bridged compound sesquiterpene logp 4.12 ALOGPS logs -4.91 ALOGPS logp 4.15 ChemAxon iupac (1S,2R,3R,6R,8R)-6-methyl-7-methylidene-3-(propan-2-yl)tricyclo[4.4.0.0^{2,8}]decane ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC(C)[C@H]1CC[C@]2(C)[C@H]3CC[C@H]([C@@H]13)C2=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9(2)11-7-8-15(4)10(3)12-5-6-13(15)14(11)12/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13+,14-,15+/m1/s1 ChemAxon inchikey VOBBUADSYROGAT-FQKPHLNHSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.7 ChemAxon polarizability 25.74 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 64800 11830550 CPD-8804 Marchini M, Charvoz C, Dujourdy L, Baldovini N, Filippi JJ: Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. J Chromatogr A. 2014 Nov 28;1370:200-15. doi: 10.1016/j.chroma.2014.10.045. Epub 2014 Oct 23. 25454145 Santos FA, Jeferson FA, Santos CC, Silveira ER, Rao VS: Antinociceptive effect of leaf essential oil from Croton sonderianus in mice. Life Sci. 2005 Oct 21;77(23):2953-63. doi: 10.1016/j.lfs.2005.05.032. 15979097 Kweka EJ, Nyindo M, Mosha F, Silva AG: Insecticidal activity of the essential oil from fruits and seeds of Schinus terebinthifolia Raddi against African malaria vectors. Parasit Vectors. 2011 Jul 5;4:129. doi: 10.1186/1756-3305-4-129. 21729280 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 1.0 2020-03-19 00:39:33 UTC 2020-08-04 22:28:20 UTC CDB000485 (1R)-(+)-trans-isolimonene (1R)-(+)-Trans-Isolimonene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. (1R) -(+)-trans-isolimonene is possibly neutral and it is one of the terpenes that are known in cannabis plant (PMID: 25454145). It was also identified in the essential oil from Salvia sharifii (7.0% relative to total oil constituents) (DOI: 10.1080/0972060X.2014.895684) and Thuja orientalis (1716.31 mg/L from wild leaves, 753.10 mg/L from planted leaves) (DOI: 10.1080/0972060X.2019.1689177). A study has shown that (1R) -(+)-trans-isolimonene has no antibacterial and antifungal effects (PMID: 8693045). C10H16 136.23 136.1252 (3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene (3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene C[C@@H]1CC[C@H](C=C1)C(C)=C InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9-10H,1,5,7H2,2-3H3/t9-,10-/m0/s1 TWCNAXRPQBLSNO-UWVGGRQHSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 4.23 ALOGPS logs -3.59 ALOGPS logp 3.26 ChemAxon iupac (3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles C[C@@H]1CC[C@H](C=C1)C(C)=C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9-10H,1,5,7H2,2-3H3/t9-,10-/m0/s1 ChemAxon inchikey TWCNAXRPQBLSNO-UWVGGRQHSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.75 ChemAxon polarizability 17.21 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 78790 Marchini M, Charvoz C, Dujourdy L, Baldovini N, Filippi JJ: Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. J Chromatogr A. 2014 Nov 28;1370:200-15. doi: 10.1016/j.chroma.2014.10.045. Epub 2014 Oct 23. 25454145 Naigre R, Kalck P, Roques C, Roux I, Michel G: Comparison of antimicrobial properties of monoterpenes and their carbonylated products. Planta Med. 1996 Jun;62(3):275-7. doi: 10.1055/s-2006-957877. 8693045 1.0 2020-03-19 00:39:41 UTC 2020-08-04 22:28:20 UTC CDB000487 1-Butanol 1-Butanol, also known as N-butan-1-ol or N-butyl alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Thus, 1-butanol is considered to be a fatty alcohol lipid molecule. 1-Butanol is a hydrophobic molecule, poorly soluble in water, and relatively neutral. 1-Butanol is an alcohol with a 4-carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermentation through the butanoate metabolic pathway. It has been found in Bacillus, Clostridium, Escherichia, Lactobacillus, Pseudomonas, Saccharomyces, Synechococcus and Thermoanaerobacterium (http://publications.lib.chalmers.se/records/fulltext/162787.pdf) (https://ac.els-cdn.com/S0079635206800470/1-s2.0-S0079635206800470-main.pdf?_tid=1db841d3-3e7b-496f-beae-05ff16913bc6&acdnat=1550288698_645db12231ee1d15d4bb7036d31d8aad) (https://dl.uctm.edu/journal/node/j2018-4/8_17-182_p_683-696.pdf). 1-Butanol is a sweet, balsam, and fruit tasting compound. In plants, 1-Butanol is found, on average, in the highest concentration in highbush blueberries and bilberries. 1-Butanol has also been detected, but not quantified in several different foods, such as napa cabbages, wild rices, red rices, bamboo shoots, and lemon verbena. 1-butanol has also been reported to be detected as a part of Cannabis sativa volatiles (PMID: 26657499). 1-Butyl alcohol 1-Hydroxybutane BuOH N-Butan-1-ol N-Butanol N-Butyl alcohol N-Butylalkohol Propyl carbinol Butan-1-ol Butanol Butyl alcohol Butyl hydroxide Hemostyp Methylolpropane Propylcarbinol Alcohol, N-butyl N Butyl alcohol Alcohol, butyl 1 Butanol N Butanol 1-Butanol C4H10O 74.12 74.0732 butan-1-ol butanol 71-36-3 CCCCO InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 LRHPLDYGYMQRHN-UHFFFAOYSA-N belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Primary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic acyclic compounds Hydrocarbon derivatives Aliphatic acyclic compound Hydrocarbon derivative Primary alcohol Fatty alcohols a primary alcohol alkyl alcohol primary alcohol water_solubility 63.2 mg/mL at 25 °C logp 0.88 HANSCH,C ET AL. (1995) melting_point -89.8 °C logp 0.84 ALOGPS logs 0.33 ALOGPS logp 0.81 ChemAxon pka_strongest_acidic 16.95 ChemAxon pka_strongest_basic -1.9 ChemAxon iupac butan-1-ol ChemAxon average_mass 74.12 ChemAxon mono_mass 74.0732 ChemAxon smiles CCCCO ChemAxon formula C4H10O ChemAxon inchi InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 ChemAxon inchikey LRHPLDYGYMQRHN-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 22.13 ChemAxon polarizability 9.21 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB031032 258 28885 263 C06142 DB02145 1BO C00035814 BUTANOL N-Butanol 7052 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:39:44 UTC 2020-07-31 20:34:13 UTC CDB000488 1-Butoxy-2-propanol 1-Butoxy-2-propanol belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R, R'=alkyl, aryl). 1-Butoxy-2-propanol is also an ether, comprised of a butane and a propane moieties joint by an oxygen atom. It has been identified in cannabis (PMID: 26657499) and chilli pepper (DOI: 10.1002/ffj.1913). It is soluble in water and it is the main component of paint and painting industry wastewater (PMID: 16403416). C7H16O2 132.2 132.115 (2S)-1-butoxypropan-2-ol (2S)-1-butoxypropan-2-ol 5131-66-8 CCCCOC[C@H](C)O InChI=1S/C7H16O2/c1-3-4-5-9-6-7(2)8/h7-8H,3-6H2,1-2H3/t7-/m0/s1 RWNUSVWFHDHRCJ-ZETCQYMHSA-N belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Secondary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic acyclic compounds Dialkyl ethers Hydrocarbon derivatives Aliphatic acyclic compound Dialkyl ether Ether Hydrocarbon derivative Secondary alcohol logp 1.17 ALOGPS logs -0.68 ALOGPS logp 1.17 ChemAxon pka_strongest_acidic 14.85 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (2S)-1-butoxypropan-2-ol ChemAxon average_mass 132.2 ChemAxon mono_mass 132.115 ChemAxon smiles CCCCOC[C@H](C)O ChemAxon formula C7H16O2 ChemAxon inchi InChI=1S/C7H16O2/c1-3-4-5-9-6-7(2)8/h7-8H,3-6H2,1-2H3/t7-/m0/s1 ChemAxon inchikey RWNUSVWFHDHRCJ-ZETCQYMHSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 37.6 ChemAxon polarizability 16.23 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 54289557 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Kurt U, Avsar Y, Talha Gonullu M: Treatability of water-based paint wastewater with Fenton process in different reactor types. Chemosphere. 2006 Aug;64(9):1536-40. doi: 10.1016/j.chemosphere.2005.11.026. Epub 2006 Jan 3. 16403416 1.0 2020-03-19 00:39:50 UTC 2020-08-04 22:28:20 UTC CDB000490 1-Hexanol 1-Hexanol, also known as 1-hexyl alcohol or 1-hydroxyhexane, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. 1-Hexanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Hexanol is an organic alcohol with a six-carbon chain and a chemical formula of CH3(CH2)5OH. This colorless liquid is poorly soluble in water, but miscible with ether and ethanol. Two additional straight chain isomers of 1-hexanol exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. 1-hexanol is believed to be a component of the odour of freshly mown grass. It is used in the perfume industry and as a flavouring agent. 1-Hexanol is found in many plants, some of which are lemon, tea, yellow bell pepper, and hyssop. 1-Hexanol is a common constituent of essential oils (e.g. orange-peel oil) and it has also been identified as a volatile component of Cannabis sativa (PMID: 26657499). 1-Hexyl alcohol 1-Hydroxyhexane Caproic alcohol Hexanol N-Hexyl alcohol Alcohol C-6 Alcohol(C6) Amylcarbinol BHL C6 Alcohol Caproyl alcohol Cyclohexan-1-ol Cyclohexanol Epal 6 Exxal 6 Fatty alcohol(C6) HEX Hexahydrophenol Hexalin Hexan-1-ol Hexanol-(1) Hexanol-CMPD Hexyl alcohol Hexyl alcohol (natural) Hexyl alcohol, active N-Hexan-1-ol N-Hexanol N-Hexenol Pentylcarbinol 1-Hexanol, aluminum salt 1-Hexanol C6H14O 102.17 102.1045 hexan-1-ol hexanol 111-27-3 CCCCCCO InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 ZSIAUFGUXNUGDI-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Fatty alcohols a small molecule primary alcohol logp 2.03 HANSCH,C ET AL. (1995) melting_point -44.6 °C logp 2.03 ALOGPS logs -1.09 ALOGPS logp 1.69 ChemAxon pka_strongest_acidic 16.84 ChemAxon pka_strongest_basic -2 ChemAxon iupac hexan-1-ol ChemAxon average_mass 102.17 ChemAxon mono_mass 102.1045 ChemAxon smiles CCCCCCO ChemAxon formula C6H14O ChemAxon inchi InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 ChemAxon inchikey ZSIAUFGUXNUGDI-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 31.34 ChemAxon polarizability 13.27 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008072 8103 7812 HE2 87393 C00854 C00000358 HEXANOL-CMPD 1-Hexanol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:39:55 UTC 2020-07-31 20:34:13 UTC CDB000492 1-Undecanol 1-Undecanol, also known as N-undecyl alcohol or undecan-1-ol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, 1-undecanol is considered to be a fatty alcohol lipid molecule. 1-Undecanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Undecanol is a colorless, water-insoluble liquid. It has a floral citrus like odor, and a fatty taste and is used as a flavoring ingredient in foods. 1-Undecanol can be found in fruits including apples and bananas. 1-Undecanol is a volatile component of cannabis (PMID: 26657499) and, as such, it can also be detected as constituent of marijuana smoke and is volatilized during the combustion of cannabis (marijuana) (https://doi.org/10.1007/978-1-59259-947-9_2). It is commonly produced by the reduction of 1-undecanal, the analogous aldehyde. Hendecanoic alcohol N-Hendecylenic alcohol N-Undecyl alcohol Undecan-1-ol Undecyl alcohol 1-Hendecanol 1-Undecyl alcohol Alcohol c-11 Alcohol C11 C11 Alcohol Decyl carbinol Dlcohol c-11 undecylic Fatty alcohol(C11) Hendecanol Hendecyl alcohol N-Undecan-1-ol N-Undecanol Neodol 1 Neoflex 11 Pri-N-undecyl alcohol Tip-nip UMQ UNA Undecanol-(1) C11H24O 172.31 172.1827 undecan-1-ol undecanol 112-42-5 CCCCCCCCCCCO InChI=1S/C11H24O/c1-2-3-4-5-6-7-8-9-10-11-12/h12H,2-11H2,1H3 KJIOQYGWTQBHNH-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol Fatty alcohols fatty alcohol primary alcohol melting_point 19 °C logp 4.83 ALOGPS logs -4.18 ALOGPS logp 3.92 ChemAxon pka_strongest_acidic 16.84 ChemAxon pka_strongest_basic -2 ChemAxon iupac undecan-1-ol ChemAxon average_mass 172.31 ChemAxon mono_mass 172.1827 ChemAxon smiles CCCCCCCCCCCO ChemAxon formula C11H24O ChemAxon inchi InChI=1S/C11H24O/c1-2-3-4-5-6-7-8-9-10-11-12/h12H,2-11H2,1H3 ChemAxon inchikey KJIOQYGWTQBHNH-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 54.34 ChemAxon polarizability 23.74 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7892 8184 FDB002917 87499 CPD-17288 C00019556 Undecanol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:39:59 UTC 2020-08-04 22:28:20 UTC CDB000493 1,1-Dimethyl-hydrazine 1,1-dimethylhydrazine is a chemical compound, also known as dimazine, belongs to the class of organic compounds known as alkylhydrazines. These are organonitrogen compounds that containing a hydrazine group to which an alkyl group is attached. It is a colorless liquid, with a sharp, fishy, ammonia-like smell, typical for organic amines. 1,1-dimethylhydrazine is a very strong basic compound (based on its pKa). It is miscible with water, ethanol, and kerosene. In concentration between 2.5% and 95% in the air, its vapors are flammable. Symmetrical dimethylhydrazine, 1,2-dimethylhydrazine is also known but is not as useful. 1,1-dimethylhydrazine is a dimethylated derivative of hydrazine and sometimes referred to as a hydrazine. Hydrazine is an inorganic chemical compound with an ammonia-like odor and is derived from the same industrial chemistry processes that manufactures ammonia. Direct alkylation of hydrazines with alkyl halides in the presence of a base affords alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on the level of substitution (same as in ordinary amines). The reduction of hydrazones to hydrazines is a clean way to produce 1,1-dialkylated hydrazines. Hydrazines and its methyl derivatives are toxic but LD50 values have not been reported. 1,1-dimethylhydrazine is often used in hypergolic rocket fuels. 1,1-dimethyl-hydrazine has also been identified as a volatile component of Cannabis sativa samples (PMID: 26657499). 1,1-Dimethylhydrazin Dimazine Gem-dimethylhydrazine N,N-Dimethylhydrazine Unsymmetrical dimethylhydrazine 1,1-Dimethyhydrazine Dimazine dihydrochloride Dimazine hydrochloride C2H8N2 60.1 60.0687 1,1-dimethylhydrazine 1,1-dimethylhydrazine 88733-28-2 CN(C)N InChI=1S/C2H8N2/c1-4(2)3/h3H2,1-2H3 RHUYHJGZWVXEHW-UHFFFAOYSA-N belongs to the class of organic compounds known as alkylhydrazines. These are organonitrogen compounds that containing a hydrazine group to which an alkyl group is attached. Alkylhydrazines Organic compounds Organic nitrogen compounds Organonitrogen compounds Hydrazines and derivatives Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Alkylhydrazine Hydrocarbon derivative Organopnictogen compound hydrazines logp -1.05 ALOGPS logs 1.21 ALOGPS logp -0.87 ChemAxon pka_strongest_basic 5.88 ChemAxon iupac 1,1-dimethylhydrazine ChemAxon average_mass 60.1 ChemAxon mono_mass 60.0687 ChemAxon smiles CN(C)N ChemAxon formula C2H8N2 ChemAxon inchi InChI=1S/C2H8N2/c1-4(2)3/h3H2,1-2H3 ChemAxon inchikey RHUYHJGZWVXEHW-UHFFFAOYSA-N ChemAxon polar_surface_area 29.26 ChemAxon refractivity 19.18 ChemAxon polarizability 7.05 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C19233 5976 18853 Unsymmetrical_dimethylhydrazine Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:02 UTC 2020-08-04 22:28:20 UTC CDB000494 1,2-Diethyl-benzene 1,2-Diethyl-benzene, also known as Ortho-diethylbenzene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 1,2-DiethylBenzene is possibly neutral. 1,2-DiethylBenzene is a diethylated derivative of benzene. It consists of a benzene ring with two ethyl substituents attached to it in ortho position. 1,2-DiethylBenzene belongs to the group of compounds known as Diethylbenzenes with the formula C6H4(C2H5)2. There are three known diethylbenzenes, Ortho-, Meta- and Para-diethylbenzene, depending on the position of its substituents. The meta and para derivatives have the greater commercial significance. All isomers are colorless liquids. Diethylbenzenes are produced by the alkylation of benzene with ethylene groups. Using shape-selective zeolite catalysts, the para isomer can be produced with high selectivity. Diethylbenzene is used in a mixture with methyl and/or ethyl biphenyls as a low temperature heat transfer fluid. 1,2-Diethyl-benzene is a volatile component of cannabis (PMID: 26657499) and, as such, it can also be detected as constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 1,2-Diethylbenzene is volatilized during the combustion of cannabis. C10H14 134.22 134.1096 1,2-diethylbenzene O-diethylbenzene 135-01-3 CCC1=CC=CC=C1CC InChI=1S/C10H14/c1-3-9-7-5-6-8-10(9)4-2/h5-8H,3-4H2,1-2H3 KVNYFPKFSJIPBJ-UHFFFAOYSA-N belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene and substituted derivatives Organic compounds Benzenoids Benzene and substituted derivatives Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Monocyclic benzene moiety Unsaturated hydrocarbon logp 4.55 ALOGPS logs -3.87 ALOGPS logp 3.89 ChemAxon iupac 1,2-diethylbenzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CCC1=CC=CC=C1CC ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-3-9-7-5-6-8-10(9)4-2/h5-8H,3-4H2,1-2H3 ChemAxon inchikey KVNYFPKFSJIPBJ-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 45.34 ChemAxon polarizability 16.76 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 8657 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:06 UTC 2020-08-04 22:28:20 UTC CDB000495 Prehnitene 1,2,3,4-tetramethylbenzene also known as Prehnitene or prehnitol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Prehnitene is possibly neutral. A tetramethylbenzene that consists of benzene substituted by methyl groups at positions 1, 2, 3 and 4. It is classified as an aromatic hydrocarbon with the formula C6H2(CH3)4. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Prehnitene is one of three isomers of tetramethylbenzene, the other two being isodurine (1,2,3,5-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene). Industrially, prehnitene can be isolated from the reformed fraction of oil refineries. It may also be produced by methylation of toluene, xylenes and the trimethylbenzenes hemellitene and pseudocumene (doi:10.1002/14356007.a13_227). 1,2,3,4-tetramethylbenzene has been detected as a volatile component of cannabis (PMID: 26657499) and, as such, it can also be detected as constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). Prehnitol C10H14 134.22 134.1096 1,2,3,4-tetramethylbenzene 1,2,3,4-tetramethylbenzene CC1=C(C)C(C)=C(C)C=C1 InChI=1S/C10H14/c1-7-5-6-8(2)10(4)9(7)3/h5-6H,1-4H3 UOHMMEJUHBCKEE-UHFFFAOYSA-N belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene and substituted derivatives Organic compounds Benzenoids Benzene and substituted derivatives Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Monocyclic benzene moiety Unsaturated hydrocarbon tetramethylbenzene logp 4.07 ALOGPS logs -3.64 ALOGPS logp 4.03 ChemAxon iupac 1,2,3,4-tetramethylbenzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CC1=C(C)C(C)=C(C)C=C1 ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-7-5-6-8(2)10(4)9(7)3/h5-6H,1-4H3 ChemAxon inchikey UOHMMEJUHBCKEE-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.22 ChemAxon polarizability 17.02 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10263 38997 Tetramethylbenzenes Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:10 UTC 2020-08-04 22:28:20 UTC CDB000496 1,3-Dichlorobenzene 1,3-dichlorobenzene or m-Dichlorobenzene belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. m-Dichlorobenzene is possibly neutral. m-Dichlorobenzene is a potentially toxic compound. No direct experimental information is available regarding the reproductive, developmental, or carcinogenic effects of 1,3-dichlorobenzene in humans. However, a National Toxicology Program (NTP) study reported that 1,3-dichlorobenzene caused kidney tumors in male rats and liver tumors in both sexes of mice by gavage (experimentally placing the chemical in their stomachs). The liver damage caused in rats by m-Dichlorobenzene is accompanied by induction of xenobiotic metabolizing enzymes of the phenobarbital type. In rats, a disturbance in thyroid homoeostasis can develop by hepatic enzyme induction: m-Dichlorobenzene induces glucuronosyl transferases. This leads to an increased release of T4 and T3 in the thyroid follicles. In humans, acute (short-term) exposure to 1,3-dichlorobenzene via inhalation, results in irritation of the skin, throat, and eyes. Chronic (long-term) 1,3-dichlorobenzene inhalation exposure results in effects on the liver, skin, and central nervous system (CNS). Dichlorobenzene has been detected as a volatile component of cannabis (PMID: 26657499) and, as such, it can also be detected as constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). m-Phenylene dichloride Meta-dichlorobenzene Metadichlorobenzene 1,3-Dichlorobenzene m-Dichlorobenzene C6H4Cl2 147.0 145.969 1,3-dichlorobenzene 3-dichlorobenzene ClC1=CC(Cl)=CC=C1 InChI=1S/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H ZPQOPVIELGIULI-UHFFFAOYSA-N belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. Dichlorobenzenes Organic compounds Benzenoids Benzene and substituted derivatives Halobenzenes Aromatic homomonocyclic compounds Aryl chlorides Hydrocarbon derivatives Organochlorides 1,3-dichlorobenzene Aromatic homomonocyclic compound Aryl chloride Aryl halide Hydrocarbon derivative Organochloride Organohalogen compound a chloroaromatic compound dichlorobenzene logp 3.45 ALOGPS logs -3.06 ALOGPS logp 3.18 ChemAxon iupac 1,3-dichlorobenzene ChemAxon average_mass 147.0 ChemAxon mono_mass 145.969 ChemAxon smiles ClC1=CC(Cl)=CC=C1 ChemAxon formula C6H4Cl2 ChemAxon inchi InChI=1S/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H ChemAxon inchikey ZPQOPVIELGIULI-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 35.67 ChemAxon polarizability 13.28 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 13857694 10943 C19397 Dichlorobenzene 36693 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:13 UTC 2020-07-31 20:34:15 UTC CDB000497 Melamine Melamine, also known as cyanurotriamide or pluragard, belongs to the class of organic compounds known as 1,3,5-triazines. Melamine is an organic compound with the formula C3H6N6. 1,3,5-triazines are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 3, and 5. Melamine is an extremely strong basic compound (based on its pKa). Melamine is a potentially toxic compound. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67 % nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred. Additionally, it has several other industrial uses. Melamine is also a metabolite of the pesticide cyromazine, formed in the body of mammals after ingesting cyromazine. It has been reported that cyromazine can also be converted to melamine in plants. Melamine is combined with formaldehyde to produce melamine resin, a very durable thermosetting plastic used in Formica, and melamine foam, a polymeric cleaning product. The end products include countertops, dry erase boards, fabrics, glues, housewares, dinnerware, cooking spoons, guitar saddles, guitar nuts, acoustic foam paneling, and flame retardants. Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics. Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests, such as the Kjeldahl and Dumas tests, estimate protein levels by measuring the nitrogen content, so they can be misled by adding nitrogen-rich compounds such as melamine. There is an instrument (SPRINT) developed by the company CEM Corp that allows the determination of protein content directly in some applications; this cannot be fooled by adding melamine in the sample. Ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al., (2008) for a rapid detection of melamine in untreated food samples. Ultrasounds are used to nebulize the melamine-containing liquids into a fine spray. The spray is then ionised by extractive electrospray ionisation (EESI) and analysed using tandem mass spectrometry (MS/MS). An analysis requires 30 seconds per sample. The limit of detection of melamine is a few nanograms of melamine per gram of milk. Crystallization and washing of melamine generates a considerable amount of wastewater, which is a pollutant if discharged directly into the environment. The wastewater may be concentrated into a solid (1.5-5% of the weight) for easier disposal. The solid may contain approximately 70% melamine, 23% oxytriazines (ammeline, ammelide, and cyanuric acid), 0.7% polycondensates (melem, melam, and melon). In the Eurotecnica process, however, there is no solid waste and the contaminants are decomposed to ammonia and carbon dioxide and sent as off gas to the upstream urea plant; accordingly, the wastewater can be recycled to the melamine plant itself or used as clean cooling water make-up. Melamine also enters the fabrication of melamine poly-sulfonate used as superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during its handling and pouring. It results in concrete with a lower porosity and a higher mechanical strength, exhibiting an improved resistance to aggressive environments and a longer lifetime. Melamine has been detected as a volatile component of cannabis (PMID: 26657499) and, as such, it can also be detected as constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 1,3,5-Triazine-2,4,6-triamine 2,4,6-Triamino-1,3,5-triazine 2,4,6-Triamino-S-triazine Cyanuramide Cyanuric triamide Cyanurotriamide Cyanurotriamine S-Triazinetriamine Sym-triaminotriazine Triaminotriazine 1,3, 5-Triazine-2,4,6-triamine 1,3,5-Triazine-2,4,6(1H,3H,5H)-triimine 1,3,5-Triazine-2,4,6-triamine (acd/name 4.0) 2,4, 6-Triamino-1,3,5-triazine 2,4,6-Triaminotriazine 2,4,6-Tris(1-aziridinyl)-S-triazine 4,6-Diamino-1,2-dihydro-2-imino-S-triazine ADK stab ZS 27 Aero Cyanurtriamide Cymel DG 002 (Amine) Hicophor PR Isomelamine Mark ZS 27 Pluragard Pluragard C 133 Spinflam ML 94m Teoharn Theoharn Triethylenemelamine Trisaziridinyltriazine Virset 656-4 Yukamelamine Melamine sulfate (1:1) Melamine sulfate (1:2) Melamine sulfate (2:1), dihydrate Melamine sulfate (4:1), tetrahydrate Melamine oxalate (1:1) Melamine phosphate Melamine sulfite (1:1) Melamine sulfite (2:1), tetrahydrate Melaminium citrate Melamine bis(oxymethyl)phosphonic acid salt Melamine sulfite (2:1), dihydrate Melaminium acetate acetic acid solvate C3H6N6 126.12 126.0654 1,3,5-triazinane-2,4,6-triimine melamine 108-78-1 N=C1NC(=N)NC(=N)N1 InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9) JDSHMPZPIAZGSV-UHFFFAOYSA-N belongs to the class of organic compounds known as 1,3,5-triazines. 1,3,5-triazines are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 3, and 5. 1,3,5-triazines Organic compounds Organoheterocyclic compounds Triazines 1,3,5-triazines Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds 1,3,5-triazine Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound <i>s</i>-triazine triamino-1,3,5-triazine water_solubility 3.24 mg/mL at 20 °C logp -1.37 melting_point 345 °C logp -1.87 ALOGPS logs -2.30 ALOGPS logp -0.66 ChemAxon pka_strongest_acidic 4.11 ChemAxon pka_strongest_basic 23.07 ChemAxon iupac 1,3,5-triazinane-2,4,6-triimine ChemAxon average_mass 126.12 ChemAxon mono_mass 126.0654 ChemAxon smiles N=C1NC(=N)NC(=N)N1 ChemAxon formula C3H6N6 ChemAxon inchi InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9) ChemAxon inchikey JDSHMPZPIAZGSV-UHFFFAOYSA-N ChemAxon polar_surface_area 107.64 ChemAxon refractivity 62.14 ChemAxon polarizability 11.24 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7667 7955 27915 C08737 CPD-7398 Melamine AX2 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:16 UTC 2020-07-31 20:34:13 UTC CDB000498 1,4-Diethylbenzene 1,4-Diethylbenzene, also known as p-diethylbenzene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 1,4-Diethylbenzene is a diethylated derivative of benzene. It consists of a benzene ring with two ethyl substituents attached to it in a para distribution. 1,4-Diethylbenzene belongs to the group of compounds known as diethylbenzenes with the formula C6H4(C2H5)2. There are three known diethylbenzenes: ortho-, meta- and para-diethylbenzene. Meta- and para-diethylbenzene are of greater commercial significance. The tree isomers are colorless liquids. Diethylbenzenes is produced by alkylation of benzene with ethylene groups. Using shape-selective zeolite catalysts, the para isomer can be produced with high selectivity. Diethylbenzene is used in a mixture with methyl and/or ethyl biphenyls as a low temperature heat transfer fluid. 1,4-DiethylBenzene has been detected as a volatile component of cannabis (PMID: 26657499) and, as such, it can also be detected as constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 1,4-Diethylbenzene is volatilized during the combustion of cannabis. p-Diethylbenzene C10H14 134.22 134.1096 1,4-diethylbenzene diethylbenzene 105-05-5 CCC1=CC=C(CC)C=C1 InChI=1S/C10H14/c1-3-9-5-7-10(4-2)8-6-9/h5-8H,3-4H2,1-2H3 DSNHSQKRULAAEI-UHFFFAOYSA-N belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene and substituted derivatives Organic compounds Benzenoids Benzene and substituted derivatives Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Monocyclic benzene moiety Unsaturated hydrocarbon benzenes logp 4.36 ALOGPS logs -3.85 ALOGPS logp 3.89 ChemAxon iupac 1,4-diethylbenzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CCC1=CC=C(CC)C=C1 ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-3-9-5-7-10(4-2)8-6-9/h5-8H,3-4H2,1-2H3 ChemAxon inchikey DSNHSQKRULAAEI-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 45.34 ChemAxon polarizability 17.02 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C14583 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:24 UTC 2020-08-04 22:28:20 UTC CDB000500 2-Butanone 2-Butanone or Butanone, also known as methylethylketone or MEK, belongs to the class of organic compounds known as ketones. It is an organic compound with the formula CH3C(O)CH2CH3. Ketones are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, butanone is considered to be an oxygenated hydrocarbon lipid molecule. Butanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has been isolated from hop oil (Humulus lupulus), white clover (Trifolium repens), tea, tomatoes, various fruits and other vegetable sources. It is used in the refining and extraction of fats and oils. Butanone is an irritant, but serious health effects in animals have been seen only at very high levels. When inhaled, these effects included birth defects. Butanone occurs as a natural product. It is produced by some trees and found in some fruits and vegetables in small amounts. It is also released to the air from car and truck exhausts. The known health effects to people from exposure to butanone are irritation of the nose, throat, skin, and eyes. This colorless liquid has a sharp, sweet odor, reminiscent of butterscotch and acetone. It is produced industrially at a large scale, and also occurs in trace amounts in nature. Butanol can also be found in the volatile fraction of Cannabis sativa (PMID: 26657499) and is likely a component of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 2-Butanon 2-Butanone 3-Butanone Aethylmethylketon Butanone 2 C2H5COCH3 Ethyl methyl cetone Ethyl methyl ketone Ethyl(methyl) ketone Ethylmethyl ketone Ethylmethylketon Meetco MEK Methyl acetone Methyl ethyl cetone Methyl ethyl ketone Methyl(ethyl) ketone Methylacetone Methylethyl ketone Methylethylketon Oxobutane Butan-2-one Butanone C4H8O 72.11 72.0575 butan-2-one methyl(ethyl) ketone 78-93-3 CCC(C)=O InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 ZWEHNKRNPOVVGH-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons a methyl-ethyl-ketone dialkyl ketone methyl ketone water_solubility 223.0 mg/mL logp 0.29 HANSCH,C ET AL. (1995) melting_point -86.6 °C logp 0.41 ALOGPS logs 0.11 ALOGPS logp 0.81 ChemAxon pka_strongest_acidic 19.68 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac butan-2-one ChemAxon average_mass 72.11 ChemAxon mono_mass 72.0575 ChemAxon smiles CCC(C)=O ChemAxon formula C4H8O ChemAxon inchi InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 ChemAxon inchikey ZWEHNKRNPOVVGH-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 20.82 ChemAxon polarizability 8.28 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB030703 C02845 6321 6569 28398 MEK Butanone 5461 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:27 UTC 2020-07-31 20:34:13 UTC CDB000501 2-Butoxyethanol 2-Butoxyethanol, also known as butylcellosolve or 3-oxa-1-heptanol, is a primary alcohol and it also belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. 2-Butoxyethanol is used in food processing as a processing aid, sanitizer, and solvent. 2-Butoxyethanol is an organic solvent with the formula C6H14O2. It is a colorless liquid with a sweet, ether-like odour. It is a butyl ether of ethylene glycol but should not be confused with it. The main use of 2-butoxyethanol is as a solvent in paints and surface coatings, followed by cleaning products and inks. Other products which contain 2-butoxyethanol include acrylic resin formulations, asphalt release agents, firefighting foam, leather protectors, oil spill dispersants, bowling pin and lane degreaser, and photographic strip solutions. 2-Butoxyethanol is a primary ingredient of various whiteboard cleaners, liquid soaps, cosmetics, dry cleaning solutions, lacquers, varnishes, herbicides, and latex paints. 2-Butoxyethanol has also been found in the volatile fraction of Cannabis sativa (PMID: 26657499). 2-Hydroxyethyl N-butyl ether 3-Oxa-1-heptanol BuOCH2ch2oh Butoxyethanol Butyl cellosolve Butyl glycol Butyl oxitol Ethylene glycol butyl ether Ethylene glycol mono-N-butyl ether Ethylene glycol monobutyl ether Glycol butyl ether N-Butoxyethanol O-Butyl ethylene glycol 2-Butossi-etanolo 2-Butoxy ethanol 2-BUTOXY ethanol (ethylene glycol monobutyl ether) 2-Butoxy-1-ethanol 2-Butoxy-aethanol 2-Butoxy-ethanol 2-Butoxyethan-1-ol 2-Butoxyethanol (butyl cellosolve) 2-Butoxyethanol (ethylene glycol monobutyl ether) 2-N-Butoxy-1-ethanol 2-N-Butoxyethanol beta-Butoxyethanol BUCS Butoksyetylowy alkohol Butyglycol Butyl 2-hydroxyethyl ether Butyl cellu-sol Butyl icinol Butyl monoether glycol Butylcellosolve Butylcelosolv Butylglycol Butyloxitol Chimec NR Dowanol eb Eb solvent EGBE Egmbe Ek tasolve eb solvent Ektasolve eb Ektasolve eb solvent Eter monobutilico del etilenglicol Ether alcohol Ether monobutylique de l'ethyleneglycol Ethylene glycol mono butyl ether Ethylene glycol monobutyl ether (egbe)(2-butoxyet) Ethylene glycol N-butyl ether Ethylene glycol, monobutyl ether Ethyleneglycol monobutyl ether g Lycol ether eb Gafcol eb Glycol ether eb Glycol ether eb acetate Glycol monobutyl ether Jeffersol eb Minex BDH Monobutyl ether OF ethylene glycol Monobutyl ethylene glycol ether Monobutyl glycol ether N-Butoxyethanol sodium salt N-Butyl cellosolve Poly-solv eb C6H14O2 118.17 118.0994 2-butoxyethan-1-ol butoxyethanol 111-76-2 CCCCOCCO InChI=1S/C6H14O2/c1-2-3-5-8-6-4-7/h7H,2-6H2,1H3 POAOYUHQDCAZBD-UHFFFAOYSA-N belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. Dialkyl ethers Organic compounds Organic oxygen compounds Organooxygen compounds Ethers Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Dialkyl ether Hydrocarbon derivative Primary alcohol ether primary alcohol water_solubility 1000 mg/mL at 20 °C logp 0.83 melting_point -74.8 °C logp 0.78 ALOGPS logs -0.19 ALOGPS logp 0.76 ChemAxon pka_strongest_acidic 15.12 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 2-butoxyethan-1-ol ChemAxon average_mass 118.17 ChemAxon mono_mass 118.0994 ChemAxon smiles CCCCOCCO ChemAxon formula C6H14O2 ChemAxon inchi InChI=1S/C6H14O2/c1-2-3-5-8-6-4-7/h7H,2-6H2,1H3 ChemAxon inchikey POAOYUHQDCAZBD-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 33.18 ChemAxon polarizability 14.37 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003389 13836399 8133 63921 C19355 2-Butoxyethanol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:30 UTC 2020-07-31 20:34:19 UTC CDB000502 alpha-Chloroacetophenone alpha-Chloroacetophenone or 2-Chloroacetophenone, also known as mace, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. alpha-Chloroacetophenone is a useful building block in organic chemistry. Although it is potentially a toxic compound, alpha-chloroacetophenone is commonly used as a tear gas. Due to its peripheral sensory irritant effect, it has been historically used as a riot control agent. alpha-Chloroacetophenone is synthesized by the Friedel-Crafts acylation of benzene using chloroacetyl chloride, with an aluminium chloride catalyst. 1-Chloroacetophenone 2 Chloroacetophenone Mace 2 chloro 1 Phenylethanone 2-chloro-1-Phenylethanone Chloracetophenone Chloroacetophenone Omega chloroacetophenone Omega-chloroacetophenone 3'-Chloroacetophenone alpha Chloroacetophenone alpha-Chloroacetophenone 3' Chloroacetophenone C8H7ClO 154.59 154.0185 2-chloro-1-phenylethan-1-one phenacyl chloride 532-27-4 ClCC(=O)C1=CC=CC=C1 InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 IMACFCSSMIZSPP-UHFFFAOYSA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic homomonocyclic compounds Alkyl chlorides Alpha-chloroketones Aryl alkyl ketones Benzoyl derivatives Hydrocarbon derivatives Organic oxides Organochlorides Alkyl chloride Alkyl halide Alkyl-phenylketone Alpha-chloroketone Alpha-haloketone Aromatic homomonocyclic compound Aryl alkyl ketone Benzenoid Benzoyl Hydrocarbon derivative Monocyclic benzene moiety Organic oxide Organochloride Organohalogen compound logp 1.90 ALOGPS logs -2.63 ALOGPS logp 2.07 ChemAxon pka_strongest_acidic 15.37 ChemAxon pka_strongest_basic -7.7 ChemAxon iupac 2-chloro-1-phenylethan-1-one ChemAxon average_mass 154.59 ChemAxon mono_mass 154.0185 ChemAxon smiles ClCC(=O)C1=CC=CC=C1 ChemAxon formula C8H7ClO ChemAxon inchi InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 ChemAxon inchikey IMACFCSSMIZSPP-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 41.21 ChemAxon polarizability 15.06 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10757 Phenacyl chloride 1.0 2020-03-19 00:40:34 UTC 2020-08-04 22:28:20 UTC CDB000503 2,6-Dimethyl styrene 2-ethenyl-1,3-dimethylbenzene, also known as 2-vinyl-1,3-dimethyl benzene or 2,6-dimethyl styrene, is a dimethylated derivative of styrene. Styrene is a colorless liquid that evaporates easily and has a sweet smell. It often contains other chemicals that give it a sharp, unpleasant smell. Styrene and styrene derivatives such as 2,6-dimethyl styrene occurs naturally in small quantities in some plants and foods (cinnamon, coffee beans, and peanuts) and is also found in coal tar. 2,6-dimethyl styrene has also been reported to be found in Cannabis sativa (PMID: 6991645). C10H12 132.21 132.0939 2-ethenyl-1,3-dimethylbenzene 2-ethenyl-1,3-dimethylbenzene 2039-90-9 CC1=CC=CC(C)=C1C=C InChI=1S/C10H12/c1-4-10-8(2)6-5-7-9(10)3/h4-7H,1H2,2-3H3 OWRKXOZFTROHSH-UHFFFAOYSA-N belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Styrenes Organic compounds Benzenoids Benzene and substituted derivatives Styrenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Cyclic olefins m-Xylenes Aromatic homomonocyclic compound Aromatic hydrocarbon Cyclic olefin Hydrocarbon M-xylene Olefin Styrene Unsaturated hydrocarbon Xylene logp 3.73 ALOGPS logs -3.81 ALOGPS logp 3.74 ChemAxon iupac 2-ethenyl-1,3-dimethylbenzene ChemAxon average_mass 132.21 ChemAxon mono_mass 132.0939 ChemAxon smiles CC1=CC=CC(C)=C1C=C ChemAxon formula C10H12 ChemAxon inchi InChI=1S/C10H12/c1-4-10-8(2)6-5-7-9(10)3/h4-7H,1H2,2-3H3 ChemAxon inchikey OWRKXOZFTROHSH-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 45.83 ChemAxon polarizability 16.09 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 16266 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:40:38 UTC 2020-07-31 20:34:13 UTC CDB000504 2-Ethoxyethanol 2-Ethoxyethanol is a diluent in colour additive mixtures for marking food. 2-Ethoxyethanol, is also known by the trademark Cellosolve. It is a primary alcohol and it also belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. 2-Ethoxyethanol is a solvent, widely used in commercial and industrial applications. It is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate. 2-Ethoxyethanol is able to dissolve diverse types of chemical compounds, in a wide range of polarities. Hence, it is capable of dissolving oils, resins, grease, waxes, nitrocellulose, and lacquers. Due to this property it has been used as a multi-purpose cleaner and 2-ethoxyethanol is therefore used in products such as varnish removers and degreasing solutions. The industrial production of 2-ethoxyethanol is performed by the reaction of ethylene oxide with ethanol. 2-Ethoxyethanol has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 2-Ethoxyethyl alcohol 2EE beta-Ethoxyethanol Cellosolve Ethylene glycol ethyl ether Ethylene glycol monoethyl ether HOCH2CH2OC2H5 Oxitol b-Ethoxyethanol Β-ethoxyethanol 2-Ethoxy-ethanol 2-Ethoxyethanol (cellosolve) Athylenglykol-monoathylather Bikanol e 1 Bikanol e1 Cellosolve solvent Cellosolve(R) Celosolv Dowanol 8 Dowanol ee Ee solvent EGEE Emkanol Eter monoetilico del etilenglicol Ether monoethylique de l'ethylene-glycol Ethoxyethanol Ethyl 2-hydroxyethyl ether Ethyl cellosolve Ethyl ethylene glycol Ethyl glycol Ethyl icinol Ethyl-2-hydroxyethyl ether Ethylene glycol monoethyl ether (egmee) Ethylethylene glycol Etoksyetylowy alkohol ETX Glycol ether ee Glycol ethyl ether Glycol monoethyl ether HSDB 54 Hydroxy ether Jeffersol ee Plastiazan 60 Poly-solv ee Solvid Solvulose Ethylcellosolve C4H10O2 90.12 90.0681 2-ethoxyethan-1-ol 2-ethoxyethanol 110-80-5 CCOCCO InChI=1S/C4H10O2/c1-2-6-4-3-5/h5H,2-4H2,1H3 ZNQVEEAIQZEUHB-UHFFFAOYSA-N belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. Dialkyl ethers Organic compounds Organic oxygen compounds Organooxygen compounds Ethers Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Dialkyl ether Hydrocarbon derivative Primary alcohol hydroxyether primary alcohol water_solubility 1000 mg/mL logp -0.32 melting_point -70 °C logp -0.28 ALOGPS logs 0.81 ALOGPS logp -0.21 ChemAxon pka_strongest_acidic 15.12 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 2-ethoxyethan-1-ol ChemAxon average_mass 90.12 ChemAxon mono_mass 90.0681 ChemAxon smiles CCOCCO ChemAxon formula C4H10O2 ChemAxon inchi InChI=1S/C4H10O2/c1-2-6-4-3-5/h5H,2-4H2,1H3 ChemAxon inchikey ZNQVEEAIQZEUHB-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 24.05 ChemAxon polarizability 10.27 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C14687 13836591 DB02249 FDB003236 8076 ETX 46788 2-Ethoxyethanol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:41 UTC 2020-07-31 20:34:13 UTC CDB000505 2-Ethyl-1-hexanol 2-Ethyl-1-hexanol, also known as Xi-2-ethyl-1-hexanol, is primary alcohol and it belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. 2-Ethyl-1-hexanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Ethyl-1-hexanol is a sweet, citrus, and floral tasting compound. 2-Ethyl-1-hexanol can be found, on average, in the highest concentration in corns and peppermints but it has also been detected in several different foods, such as cucumbers, evergreen blackberries, rabbiteye blueberries, sweet cherries, and tea. 2-Ethyl-1-hexanol has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). C8H18O 130.23 130.1358 (2S)-2-ethylhexan-1-ol (2S)-2-ethylhexan-1-ol 104-76-7 CCCC[C@H](CC)CO InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3/t8-/m0/s1 YIWUKEYIRIRTPP-QMMMGPOBSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol logp 3.01 ALOGPS logs -2.21 ALOGPS logp 2.5 ChemAxon pka_strongest_acidic 17.7 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (2S)-2-ethylhexan-1-ol ChemAxon average_mass 130.23 ChemAxon mono_mass 130.1358 ChemAxon smiles CCCC[C@H](CC)CO ChemAxon formula C8H18O ChemAxon inchi InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3/t8-/m0/s1 ChemAxon inchikey YIWUKEYIRIRTPP-QMMMGPOBSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 40.41 ChemAxon polarizability 17.02 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6991980 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:45 UTC 2020-08-04 22:28:20 UTC CDB000506 2-Ethyl toluene 2-Ethyl toluene or 1-ethyl-2-methylbenzene is an organic compound and a member of the class of toluenes carrying an ethyl group at the ortho-position. 2-Ethyl toluene or¬†o-ethyltoluene belongs to the family of Toluenes. 2-Ethyl toluene is an ethylated derivative of toluene. Toluene is a sweet and paint tasting compound. Toluene is found, on average, in the highest concentration within a few different foods, such as black walnuts, rosemaries, and corianders and in a lower concentration in milk (cow) and kohlrabis. Toluene has also been detected, but not quantified in several different foods, such as prickly pears, citrus, yellow bell peppers, apples, and garden tomato (var.). Toluene is a drug which is used for the removal of ascarids (Toxocara canis and Toxascaris leonina) and hookworms (Ancylostoma caninum and Uncinaria stenocephala). Toluene and its derivatives are also a part of the volatile compounds found in cannabis plants (PMID: 26657499).¬†O-ethyltoluene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 1,2-Methylethylbenzene 1-Methyl-2-ethylbenzene 2-Ethyltoluene O-Methylethylbenzene Ortho-ethyltoluene 1-Ethyl-2-methylbenzene O-Ethyltoluene C9H12 120.19 120.0939 1-ethyl-2-methylbenzene o-ethyltoluene CCC1=CC=CC=C1C InChI=1S/C9H12/c1-3-9-7-5-4-6-8(9)2/h4-7H,3H2,1-2H3 HYFLWBNQFMXCPA-UHFFFAOYSA-N belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. Toluenes Organic compounds Benzenoids Benzene and substituted derivatives Toluenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Toluene Unsaturated hydrocarbon toluenes logp 3.87 ALOGPS logs -3.33 ALOGPS logp 3.44 ChemAxon iupac 1-ethyl-2-methylbenzene ChemAxon average_mass 120.19 ChemAxon mono_mass 120.0939 ChemAxon smiles CCC1=CC=CC=C1C ChemAxon formula C9H12 ChemAxon inchi InChI=1S/C9H12/c1-3-9-7-5-4-6-8(9)2/h4-7H,3H2,1-2H3 ChemAxon inchikey HYFLWBNQFMXCPA-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 40.74 ChemAxon polarizability 14.86 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11903 34276 C14572 4-Ethyltoluene Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:48 UTC 2020-07-31 20:34:13 UTC CDB000507 2-Heptanone 2-Heptanone, also known as butylacetone or heptan-2-one, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). 2-Heptanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a colorless, water-like liquid with a blue-cheesy, banana-like, fruity or cinnamon odor. It has a cheesy, cocount-like taste. 2-Heptanone is one of several ketones that are found in cannabis plants (PMID: 6991645). 2-Heptanone is an FDA-approved food additive and is also used as a perfuming agent or fragrance in cosmetics. 2-Heptanone can be added to baked goods, condiments and hard candy. 2-Heptanone occurs naturally in certain foods such as beer, white bread, butter, various cheeses and potato chips. 2-Heptanone is one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. Butylacetone Methyl N-amyl ketone Methyl pentyl ketone N-Amyl methyl ketone N-Pentyl methyl ketone Heptan-2-one 1-Methylhexanal 2-Oxoheptane Amyl methyl ketone Methyl amyl ketone Methyl N-pentyl ketone Pentyl methyl ketone Methyl-N-amyl ketone 2-Heptanone C7H14O 114.19 114.1045 heptan-2-one 2-heptanone 29299-43-2 CCCCCC(C)=O InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 CATSNJVOTSVZJV-UHFFFAOYSA-N belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Ketone Organic oxide Oxygenated hydrocarbons Oxygenated hydrocarbons dialkyl ketone methyl ketone water_solubility 4.3 mg/mL at 25 °C logp 1.98 HANSCH,C ET AL. (1995) melting_point -35 °C logp 1.92 ALOGPS logs -1.70 ALOGPS logp 2.14 ChemAxon pka_strongest_acidic 19.64 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac heptan-2-one ChemAxon average_mass 114.19 ChemAxon mono_mass 114.1045 ChemAxon smiles CCCCCC(C)=O ChemAxon formula C7H14O ChemAxon inchi InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 ChemAxon inchikey CATSNJVOTSVZJV-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 34.62 ChemAxon polarizability 14.31 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008055 C08380 7760 8051 5672 C00001254 2-Heptanone Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:40:51 UTC 2020-08-04 22:28:21 UTC CDB000508 2-Hydroxyacetophenon 2-hydroxyacetophenone, also known as benzoylcarbinol or glycolophenone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2-hydroxyacetophenone is a neutral, hydrohpobic compound that is largely insoluble in water. 2-hydroxyacetophenone has a sweet, honey, tropical, almond or herbal odor and a cinnamon, cherry or tobacco-like taste. It occurs naturally in a number of foods including roasted almonds, coffee, papaya, rum, sherry and tomatoes. 2-hydroxyacetophenone has also been reported to be found in Cannabis sativa (PMID: 6991645). alpha-Hydroxyacetophenone Benzoylcarbinol Glycolophenone Hydroxymethyl phenyl ketone Omega-hydroxyacetophenone Phenacyl alcohol a-Hydroxyacetophenone Α-hydroxyacetophenone 1-Phenyl-2-hydroxyethanone C8H8O2 136.15 136.0524 2-hydroxy-1-phenylethan-1-one hydroxyacetophenone 582-24-1 OCC(=O)C1=CC=CC=C1 InChI=1S/C8H8O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,9H,6H2 ZWVHTXAYIKBMEE-UHFFFAOYSA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic homomonocyclic compounds Alpha-hydroxy ketones Aryl alkyl ketones Benzoyl derivatives Hydrocarbon derivatives Organic oxides Primary alcohols Alcohol Alkyl-phenylketone Alpha-hydroxy ketone Aromatic homomonocyclic compound Aryl alkyl ketone Benzenoid Benzoyl Hydrocarbon derivative Monocyclic benzene moiety Organic oxide Primary alcohol monohydroxyacetophenone primary alcohol logp 0.74 ALOGPS logs -1.08 ALOGPS logp 0.71 ChemAxon pka_strongest_acidic 13.79 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 2-hydroxy-1-phenylethan-1-one ChemAxon average_mass 136.15 ChemAxon mono_mass 136.0524 ChemAxon smiles OCC(=O)C1=CC=CC=C1 ChemAxon formula C8H8O2 ChemAxon inchi InChI=1S/C8H8O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,9H,6H2 ChemAxon inchikey ZWVHTXAYIKBMEE-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 38.16 ChemAxon polarizability 14.05 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 68490 C07189 28341 Hydroxyacetophenone Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:53 UTC 2020-07-31 20:34:13 UTC CDB000509 2-Isopropenyl-3-methylpyrazine 2-Isopropenyl-3-methylpyrazine belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-membered aromatic heterocycle, that includes two nitrogen atoms (at positions 1 and 4) and four carbon atoms. 2-Isopropenyl-3-methylpyrazine is a moderately basic compound (based on its pKa). 2-Isopropenyl-3-methylpyrazine is a methylated derivative of 2-isopropenylpyrazine on which one methyl group has been added at the position C-3 of the benzene ring. 2-Isopropenylpyrazine is a caramel, chocolate, and nutty tasting compound. 2-Isopropenylpyrazine has been detected, but not quantified, in several different foods such as nuts, cereals and cereal products, pulses, cocoa and cocoa products, and tea. Pyrazines and alkylated pyrazines have also been found in the volatile fraction of Cannabis sativa (PMID: 26657499) and are likely a component of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). C8H10N2 134.18 134.0844 2-methyl-3-(prop-1-en-2-yl)pyrazine 2-methyl-3-(prop-1-en-2-yl)pyrazine CC(=C)C1=NC=CN=C1C InChI=1S/C8H10N2/c1-6(2)8-7(3)9-4-5-10-8/h4-5H,1H2,2-3H3 NJUMRZOJYYCHHV-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Pyrazines Organic compounds Organoheterocyclic compounds Diazines Pyrazines Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyrazine logp 1.29 ALOGPS logs -0.80 ALOGPS logp 1.09 ChemAxon pka_strongest_basic 1.39 ChemAxon iupac 2-methyl-3-(prop-1-en-2-yl)pyrazine ChemAxon average_mass 134.18 ChemAxon mono_mass 134.0844 ChemAxon smiles CC(=C)C1=NC=CN=C1C ChemAxon formula C8H10N2 ChemAxon inchi InChI=1S/C8H10N2/c1-6(2)8-7(3)9-4-5-10-8/h4-5H,1H2,2-3H3 ChemAxon inchikey NJUMRZOJYYCHHV-UHFFFAOYSA-N ChemAxon polar_surface_area 25.78 ChemAxon refractivity 39.93 ChemAxon polarizability 14.86 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 583834 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:56 UTC 2020-08-04 22:28:21 UTC CDB000510 2-Methylnaphthalene 2-Methylnaphthalene belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 2-methylnaphthalene is a potentially toxic compound. 2-Methylnaphthalene is also considered a Plycyclic Aromatic Hydrocarbon (PAH). NASA announced on February 22, 2014 a greatly upgraded database for detecting and monitoring PAHs in the universe, including 2-methylnaphthalene. According to NASA scientists, over 20% of the carbon in the universe may be associated with PAHs, possible starting materials for the formation of life. PAHs seem to have been formed shortly after the Big Bang, are abundant in the universe, and are associated with new stars and exoplanets. In the human body, many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. Exposure to large amounts of 2-methylnapthalene may also cause nausea, vomiting, diarrhea, blood in the urine, and a yellow color to the skin. 2-Methylnaphthalene has been found in the volatile fraction of Cannabis sativa (PMID: 26657499) and is a component of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). It is volatilized during the combustion of cannabis. beta-Methylnaphthalene b-Methylnaphthalene Β-methylnaphthalene 2-Methylnaphthalene, ion(1+) 2-Methylnaphthalene, ion(1-) 2-Methylnaphthalene, lithium salt, ion(1-) 2-Methylnaphthalene, methyl-13C-labeled 2-Methylnaphthalene, naphthalene-1-(13)C-labeled C11H10 142.2 142.0783 2-methylnaphthalene 2-methylnaphthalene 7419-61-6 CC1=CC2=CC=CC=C2C=C1 InChI=1S/C11H10/c1-9-6-7-10-4-2-3-5-11(10)8-9/h2-8H,1H3 QIMMUPPBPVKWKM-UHFFFAOYSA-N belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalenes Organic compounds Benzenoids Naphthalenes Aromatic homopolycyclic compounds Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons Aromatic homopolycyclic compound Aromatic hydrocarbon Hydrocarbon Naphthalene Polycyclic hydrocarbon Unsaturated hydrocarbon methylnaphthalene logp 3.83 ALOGPS logs -3.91 ALOGPS logp 3.48 ChemAxon iupac 2-methylnaphthalene ChemAxon average_mass 142.2 ChemAxon mono_mass 142.0783 ChemAxon smiles CC1=CC2=CC=CC=C2C=C1 ChemAxon formula C11H10 ChemAxon inchi InChI=1S/C11H10/c1-9-6-7-10-4-2-3-5-11(10)8-9/h2-8H,1H3 ChemAxon inchikey QIMMUPPBPVKWKM-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 47.55 ChemAxon polarizability 16.78 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB007631 7055 C14098 50720 2-Methylnaphthalene Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:40:59 UTC 2020-08-04 22:28:21 UTC CDB000511 2-Methyl-1H-imidazole 2-Methylimidazole, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-membered ring, that includes two nitrogen atoms at positions 1 and 3, and three carbon atoms. 2-MethylImidazole has the chemical formula CH3C3H2N2H and is a methylated derivative of Imidazole on which a methyl group has been added at position C-2. It is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in coordination chemistry. 2-Methylimidazole is prepared by condensation of glyoxal, ammonia, and acetaldehyde, through the Radziszewski reaction. 2-Methylimidazole is a sterically hindered imidazole that is used to simulate the coordination of histidine to heme complexes. It can be deprotonated to make imidazolate-based coordination polymers. 2-Methylimidazole is a precursor to several members of the nitroimidazole antibiotics that are used to combat anaerobic bacterial and parasitic infections. 2-methylimidazole has been found in the volatile fraction of Cannabis sativa (PMID: 26657499) and is likely a component of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 2-Methylimidazole hydrochloride 2-Methylimidazole, silver (1+) salt ZN(2-Methylimidazole)2 C4H6N2 82.1 82.0531 2-methyl-1H-imidazole 1H-imidazole, 2-methyl- 693-98-1 CC1=NC=CN1 InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6) LXBGSDVWAMZHDD-UHFFFAOYSA-N belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Imidazoles Organic compounds Organoheterocyclic compounds Azoles Imidazoles Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Imidazole Organic nitrogen compound Organonitrogen compound Organopnictogen compound logp 0.36 ALOGPS logs 0.86 ALOGPS logp -0.022 ChemAxon pka_strongest_acidic 13.92 ChemAxon pka_strongest_basic 7.52 ChemAxon iupac 2-methyl-1H-imidazole ChemAxon average_mass 82.1 ChemAxon mono_mass 82.0531 ChemAxon smiles CC1=NC=CN1 ChemAxon formula C4H6N2 ChemAxon inchi InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6) ChemAxon inchikey LXBGSDVWAMZHDD-UHFFFAOYSA-N ChemAxon polar_surface_area 28.68 ChemAxon refractivity 23.45 ChemAxon polarizability 8.74 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12749 C19261 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:02 UTC 2020-07-31 20:34:13 UTC CDB000512 2-Methyl-2-propanamine 2-Methyl-2-propanamine, also known as trimethylaminomethane or 1,1-dimethylethylamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. A primary aliphatic amine that is ethylamine substituted by two methyl groups at position 1. 2-Methyl-2-propanamine with the molecular formula (CH3)3CNH2 is a strong basic compound (based on its pKa). 2-Methyl-2-propanamine is a colorless liquid with a typical amine-like odor. 2-Methyl-2-propanamine or tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine. 2-Methyl-2-propanamine is produced commercially by direct amination of isobutylene using zeolite catalysts. In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide. 2-Methyl-2-propanamine is used as an intermediate in the preparation of the sulfenamides such as N-tert-butyl-2-benzothiazylsulfenamide and N-tert-butyl-2-benzothiazylsulfenimide. In pharmacology under the name erbumine, 2-methyl-2-propanamine has been used as a counterion in drug substances such as perindopril erbumine. 2-methyl-2-propanamine has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) and is likely a smoke component of marijuana (https://doi.org/10.1007/978-1-59259-947-9_2). 1,1-Dimethylethanamine 1,1-Dimethylethylamine 2-Methyl-2-propanamine 2-Methyl-2-propylamine Erbumine t-Butylamine TERTIARY-butylamine Trimethylaminomethane Tert-butylamine perchlorate Tert-butylamine hydrobromide Tert-butylamine monolithium salt Tert-butylamine thiocyanate Tert-butylamine, conjugate acid Tert-butylamine hydrochloride Tert-butylamine hydroiodide Tert-butylamine sulfate (2:1) C4H11N 73.14 73.0891 2-methylpropan-2-amine erbumine CC(C)(C)N InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3 YBRBMKDOPFTVDT-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine primary aliphatic amine logp 0.81 ALOGPS logs 0.13 ALOGPS logp 0.43 ChemAxon pka_strongest_basic 10.65 ChemAxon iupac 2-methylpropan-2-amine ChemAxon average_mass 73.14 ChemAxon mono_mass 73.0891 ChemAxon smiles CC(C)(C)N ChemAxon formula C4H11N ChemAxon inchi InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3 ChemAxon inchikey YBRBMKDOPFTVDT-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 23.72 ChemAxon polarizability 9.38 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6385 44639 FDB093425 CPD-15151 Tert-Butylamine Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:07 UTC 2020-08-04 22:28:21 UTC CDB000513 2-Methylaziridine 2-MethylAziridine, also known as propyleneimine, belongs to the class of organic compounds known as aziridines. It is a secondary amine and the smallest chiral aziridine (ring containing C2N). These are organic compounds containing a saturated three-member heterocycle with one amino group and two methylene groups. The chemical formula of 2-methylaziridine is CH3CH(NH)CH2. 2-Methylaziridine is a very strong basic compound (based on its pKa) and it is a flammable colorless liquid. It is used in the paper, textile, rubber and pharmaceutical industries and its derivatives, copolymers and oligomers, are of commercial interest. The compound is also of interest for the synthesis of dendrimers, a process that exploits the tendency of aziridines to undergo ring-opening reactions. 2-Methylaziridine is also used in making paint. NIOSH considers 2-methylaziridine a potential occupational carcinogen. 2-Methylaziridine has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) and is likely a smoke component of marijuana (https://doi.org/10.1007/978-1-59259-947-9_2). C3H7N 57.1 57.0578 (2S)-2-methylaziridine (2S)-2-methylaziridine 41927-28-0 C[C@H]1CN1 InChI=1S/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3/t3-/m0/s1 OZDGMOYKSFPLSE-VKHMYHEASA-N logp -0.47 ALOGPS logs 0.97 ALOGPS logp 0.052 ChemAxon pka_strongest_basic 7.95 ChemAxon iupac (2S)-2-methylaziridine ChemAxon average_mass 57.1 ChemAxon mono_mass 57.0578 ChemAxon smiles C[C@H]1CN1 ChemAxon formula C3H7N ChemAxon inchi InChI=1S/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3/t3-/m0/s1 ChemAxon inchikey OZDGMOYKSFPLSE-VKHMYHEASA-N ChemAxon polar_surface_area 21.94 ChemAxon refractivity 17.14 ChemAxon polarizability 6.78 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 186632 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:10 UTC 2020-07-31 20:34:13 UTC CDB000514 2-Methylpentane 2-Methylpentane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. It is a structural isomer of hexane composed of a methyl group bonded to the second carbon atom in a pentane chain. 2-Methylpentane is possibly neutral. 2-Methylpentane is a potentially toxic compound. It causes degeneration of the peripheral nervous system (and eventually the central nervous system), starting with damage to the nerve axons. It is distributed throughout the body in the blood and metabolized by mixed function oxidases in the liver to a number of metabolites. Certain kinds of special glues used in the roofing and shoe and leather industries also contain hexane. 2-Methyl-pentane C6H14 86.18 86.1096 2-methylpentane 2-methylpentane CCCC(C)C InChI=1S/C6H14/c1-4-5-6(2)3/h6H,4-5H2,1-3H3 AFABGHUZZDYHJO-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane logp 3.60 ALOGPS logs -3.27 ALOGPS logp 2.97 ChemAxon iupac 2-methylpentane ChemAxon average_mass 86.18 ChemAxon mono_mass 86.1096 ChemAxon smiles CCCC(C)C ChemAxon formula C6H14 ChemAxon inchi InChI=1S/C6H14/c1-4-5-6(2)3/h6H,4-5H2,1-3H3 ChemAxon inchikey AFABGHUZZDYHJO-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 29.36 ChemAxon polarizability 12.09 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7892 2-Methylpentane 1.0 2020-03-19 00:41:15 UTC 2020-08-04 22:28:21 UTC CDB000515 2-Nitropropane 2-Nitropropane, also known as i-C3H7NO2, belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon. 2-Nitropropane is a very weakly acidic compound (based on its pKa). 2-Nitropropane is a potentially toxic compound. It is a secondary nitroalkane with propane being the carbon backbone, on which a hydrogen at position 2 has been replaced by a nitro group. 2-Nitropropane is a colorless liquid and it is used a solvent. 2-Nitropropane is produced by the high-temperature vapor-phase nitration of propane and usually contains 1-nitropropane as an impurity. 2-Nitropropane is also produced as a volatile by-product that can be captured during Leonard's ring-closure hydantoin preparation. 2-Nitropropane is used as a solvent or additive in inks, paints, adhesives, varnishes, polymers, resins, fuel, and coatings. It is also used as a feedstock for other industrial chemicals, and in the synthesis of pharmaceuticals such as phentermine, chlorphentermine, and teclozan. It serves as an oxidant in the Hass‚ÄìBender oxidation process. 2-Nitropropane has been detected as a volatile component of seized cannabis samples (PMID: 26657499) and it is also a constituent of tobacco smoke (PMID: 21556207). Based on studies in animals, it is reasonably anticipated to be a human carcinogen (PMID: 2038276) and it is listed as an IARC Group 2B carcinogen. Dimethylnitromethane I-C3H7NO2 Isonitropropane Sec-nitropropane C3H7NO2 89.09 89.0477 2-nitropropane β-nitropropane 79-46-9 CC(C)[N+]([O-])=O InChI=1S/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3 FGLBSLMDCBOPQK-UHFFFAOYSA-N belongs to the class of organic compounds known as c-nitro compounds. C-nitro compounds are compounds having the nitro group, -NO2 (free valence on nitrogen), which is attached to carbon. C-nitro compounds Organic compounds Organic 1,3-dipolar compounds Allyl-type 1,3-dipolar organic compounds Organic nitro compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Organic oxoazanium compounds Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound C-nitro compound Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxoazanium Organic oxygen compound Organonitrogen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound C-nitro compound a small molecule logp 0.71 ALOGPS logs -0.62 ALOGPS logp 0.8 ChemAxon pka_strongest_acidic 9.32 ChemAxon iupac 2-nitropropane ChemAxon average_mass 89.09 ChemAxon mono_mass 89.0477 ChemAxon smiles CC(C)[N+]([O-])=O ChemAxon formula C3H7NO2 ChemAxon inchi InChI=1S/C3H7NO2/c1-3(2)4(5)6/h3H,1-2H3 ChemAxon inchikey FGLBSLMDCBOPQK-UHFFFAOYSA-N ChemAxon polar_surface_area 43.14 ChemAxon refractivity 20.75 ChemAxon polarizability 8.44 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 398 C02116 16037 CPD-244 2-Nitropropane Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A: Hazardous compounds in tobacco smoke. Int J Environ Res Public Health. 2011 Feb;8(2):613-28. doi: 10.3390/ijerph8020613. Epub 2011 Feb 23. 21556207 Haas-Jobelius M, Ziegler-Skylakakis K, Andrae U: Nitroreduction is not involved in the genotoxicity of 2-nitropropane in cultured mammalian cells. Mutagenesis. 1991 Jan;6(1):87-91. doi: 10.1093/mutage/6.1.87. 2038276 1.0 2020-03-19 00:41:19 UTC 2020-07-31 20:34:13 UTC CDB000516 2-Phenoxyethanol 2-Phenoxyethanol, also known as phenoxytol or phenyl cellosolve, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. 2-Phenoxyethanol is a potentially toxic compound. 2-Phenoxyethanol is a germicidal and germistatic glycol ether, phenol ether, and aromatic alcohol often used together with quaternary ammonium compounds. 2-Phenoxyethanol is used as a perfume fixative, an insect repellent, an antiseptic, a solvent for cellulose acetate, dyes, inks, and resins. It is also a preservative for pharmaceuticals, cosmetics and lubricants, an anesthetic in fish aquaculture, and it is also used in organic synthesis. 2-Phenoxyethanol is produced by the hydroxyethylation of phenol (Williamson synthesis), for example, in the presence of alkali-metal hydroxides or alkali-metal borohydrides. 2-Phenoxyethanol has been identified as a volatile component of cannabis samples from police seizures (PMID: 26657499) and it is also a constituent of Marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 1-Hydroxy-2-phenoxyethane 2-Hydroxyethyl phenyl ether 2-Phenoxyethyl alcohol beta-Hydroxyethyl phenyl ether Ethylene glycol monophenyl ether Phenoxyethanol Phenoxytol Phenyl cellosolve Phenylmonoglycol ether Fungal terminator b-Hydroxyethyl phenyl ether Β-hydroxyethyl phenyl ether 2-Phenoxyethanol, 9ci Dalpad a Ethylene glycol phenyl ether Newpol efp Phenoxetol Phenylcellosolve Emuclens Erisept Phenoxethol C8H10O2 138.17 138.0681 2-phenoxyethan-1-ol phenoxyethanol 122-99-6 OCCOC1=CC=CC=C1 InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 QCDWFXQBSFUVSP-UHFFFAOYSA-N belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Phenol ethers Organic compounds Benzenoids Phenol ethers Aromatic homomonocyclic compounds Alkyl aryl ethers Hydrocarbon derivatives Phenoxy compounds Primary alcohols Alcohol Alkyl aryl ether Aromatic homomonocyclic compound Ether Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Primary alcohol aromatic ether hydroxyether primary alcohol melting_point 11-13 °C logp 1.22 ALOGPS logs -0.76 ALOGPS logp 1.13 ChemAxon pka_strongest_acidic 15.1 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac 2-phenoxyethan-1-ol ChemAxon average_mass 138.17 ChemAxon mono_mass 138.0681 ChemAxon smiles OCCOC1=CC=CC=C1 ChemAxon formula C8H10O2 ChemAxon inchi InChI=1S/C8H10O2/c9-6-7-10-8-4-2-1-3-5-8/h1-5,9H,6-7H2 ChemAxon inchikey QCDWFXQBSFUVSP-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 38.81 ChemAxon polarizability 14.91 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 13848467 31236 64275 268 FDB021762 DB11304 Phenoxyethanol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:21 UTC 2020-07-31 20:34:13 UTC CDB000517 2,2,5-Trimethylhexane 2,2,5-Trimethylhexane, belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. 2,2,5-TrimethylHexane is possibly neutral. 2,2,5-TrimethylHexane is a trimethylated derivative of Hexane. Hexane is an alkane tasting compound. Hexane is found, on average, in the highest concentration within kohlrabis. Hexane has also been detected, but not quantified in several different foods, such as pomes, nuts, fruits, mushrooms, and corns. Exposure to hexane may also damage the lungs and reproductive system. Hexane is a potentially toxic compound. Continued exposure may lead to paralysis of the arms and legs. 2,2,5-TrimethylHexane is found as a component of petroleum fractions (e.g. gasoline, kerosene, and fuel oil) (https://doi.org/10.1016/j.fuel.2005.09.005). Hexanes are significant constituents of gasoline. They are all colorless liquids, odorless when pure, with boiling points between 50 and 70 °C (122 and 158 °F). They are widely used as cheap, relatively safe, largely unreactive, and easily evaporated non-polar solvents. C9H20 128.26 128.1565 2,2,5-trimethylhexane 2,2,5-trimethylhexane 3522-94-9 CC(C)CCC(C)(C)C InChI=1S/C9H20/c1-8(2)6-7-9(3,4)5/h8H,6-7H2,1-5H3 HHOSMYBYIHNXNO-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane logp 5.05 ALOGPS logs -4.60 ALOGPS logp 4.01 ChemAxon iupac 2,2,5-trimethylhexane ChemAxon average_mass 128.26 ChemAxon mono_mass 128.1565 ChemAxon smiles CC(C)CCC(C)(C)C ChemAxon formula C9H20 ChemAxon inchi InChI=1S/C9H20/c1-8(2)6-7-9(3,4)5/h8H,6-7H2,1-5H3 ChemAxon inchikey HHOSMYBYIHNXNO-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 42.98 ChemAxon polarizability 17.71 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 19041 1.0 2020-03-19 00:41:24 UTC 2020-07-31 20:34:09 UTC CDB000518 2,3,4-Trimethylpentane 2,3,4-Trimethylpentane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 2,3,4-trimethylpentane is considered to be a hydrocarbon lipid molecule. 2,3,4-Trimethylpentane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,3,4-Trimethylpentane may be a unique S. cerevisiae (yeast) metabolite. 2,3,4-Trimethylpentane is a potentially toxic compound. 2,3,4-Trimethylpentane is a trimethylated derivative of pentane. Pentane is an alkane tasting compound. Pentane found in kohlrabis, celery stalks, and soybeans. Pentane is a central nervous system depressant and can cause loss of consciousness and coma at high doses. Ingestion may cause pulmonary toxicity due to pentane aspiration, including chemical pneumonitis, acute lung injury, and hemorrhage. C8H18 114.23 114.1409 2,3,4-trimethylpentane 2,3,4-trimethylpentane 565-75-3 CC(C)C(C)C(C)C InChI=1S/C8H18/c1-6(2)8(5)7(3)4/h6-8H,1-5H3 RLPGDEORIPLBNF-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane Hydrocarbons logp 4.00 ALOGPS logs -3.97 ALOGPS logp 3.55 ChemAxon iupac 2,3,4-trimethylpentane ChemAxon average_mass 114.23 ChemAxon mono_mass 114.1409 ChemAxon smiles CC(C)C(C)C(C)C ChemAxon formula C8H18 ChemAxon inchi InChI=1S/C8H18/c1-6(2)8(5)7(3)4/h6-8H,1-5H3 ChemAxon inchikey RLPGDEORIPLBNF-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 38.45 ChemAxon polarizability 15.65 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 11269 1.0 2020-03-19 00:41:26 UTC 2020-08-04 22:28:21 UTC CDB000519 2,4-di-tert-Butylphenol 2,4-Di-tert-Butylphenol, also known as 2,4-DTBP, is a dibutylated derivative of phenol, with two isobutyl moieties positioned at C-2 and C-4. 2,4-di-tert-butylphenol is an organic compound with the structural formula 2,4-((CH3)3C)2C6H3OH. 2,4-Di-tert-butylphenol is a synthetic phenolic antioxidant (SPA). SPAs are a family of chemicals used widely in foods, polymers, and cosmetics as radical scavenging agents that slow down degradation due to oxidation. Given their widespread use, human exposure is unavoidable and there is public concern regarding environmental contamination by these chemicals. 2,4-Di-tert-butylphenol has been detected at extremely high concentrations in human urine (PMID: 31265952) and it has also been identified as a volatile component of cannabis samples from police seizures (PMID: 26657499). 1-Hydroxy-2,4-di-tert-butylbenzene 2,4-Bis(1,1'-dimethylethyl)phenol 2,4-Bis(1,1-dimethylethyl)-phenol 2,4-Bis(1,1-dimethylethyl)phenol 2,4-Bis(tert-butyl)phenol 2,4-Di-t-butylphenol 2,4-Tert-butylphenol 2,4-DTBP 2,4-Di-tert-butylphenol 2,4-Di-tert-butyl-phenol 2,4-Di-tert-butylhydroxybenzene DBP C14H22O 206.33 206.1671 2,4-di-tert-butylphenol 2,4-di-T-butylphenol 96-76-4 CC(C)(C)C1=CC(=C(O)C=C1)C(C)(C)C InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3 ICKWICRCANNIBI-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenylpropanes Organic compounds Benzenoids Benzene and substituted derivatives Phenylpropanes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Hydrocarbon derivatives Organooxygen compounds 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Hydrocarbon derivative Organic oxygen compound Organooxygen compound Phenol Phenylpropane water_solubility 0.035 mg/mL at 25 °C logp 5.19 melting_point 56.5 °C logp 4.91 ALOGPS logs -3.82 ALOGPS logp 4.76 ChemAxon pka_strongest_acidic 10.87 ChemAxon pka_strongest_basic -5 ChemAxon iupac 2,4-di-tert-butylphenol ChemAxon average_mass 206.33 ChemAxon mono_mass 206.1671 ChemAxon smiles CC(C)(C)C1=CC(=C(O)C=C1)C(C)(C)C ChemAxon formula C14H22O ChemAxon inchi InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3 ChemAxon inchikey ICKWICRCANNIBI-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 65.37 ChemAxon polarizability 25.32 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7037 7311 89188 Liu R, Mabury SA: Unexpectedly high concentrations of 2,4-di-tert-butylphenol in human urine. Environ Pollut. 2019 Sep;252(Pt B):1423-1428. doi: 10.1016/j.envpol.2019.06.077. Epub 2019 Jun 21. 31265952 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:30 UTC 2020-08-04 22:28:21 UTC CDB000520 2,4,6-Trimethylphenol 2,4,6-Trimethylphenol, also known as Mesitol, belongs to the class of organic compounds known as para-cresols. Para cresols are compounds containing a para-cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and a methyl group at position 4 (para-hydroxytoluene). 2,4,6-Trimethylphenol is a mild and phenolic tasting compound. 2,4,6-Trimethylphenol is an aromatic chemical compound having three methyl groups and one hydroxy group. The name and structure of mesitol derives from the combination of mesitylene and phenol. 2,4,6-Trimethylphenol or Mesitol can be obtained by reaction of mesitylene with peroxomonophosphoric acid. Mesitol is listed by the FDA as being used as a food additive. Mesitol has also been detected in cannabis samples obtained in police seizures (PMID: 26657499). 246-Trimethyl-phenol 246-Trimethylphenol 1,3,5-Trimethylphenol 1-Hydroxy-2,4,6-trimethylbenzene 2,4, 6-Trimethylphenol 2,4,6-Trimethyl-phenol 2,4,6-Trimethylofenol 2,4,6-Trimetylofenol 2-Hydroxy-1,3,5-trimethyl-benzene 2-Hydroxymesitylene BENZENE,1-hydroxy,2,4,6-trimethyl Mesitol Mesityl alcohol C9H12O 136.19 136.0888 2,4,6-trimethylphenol 2,4,6-trimethylphenol 527-60-6 CC1=CC(C)=C(O)C(C)=C1 InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3 BPRYUXCVCCNUFE-UHFFFAOYSA-N belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4. Para cresols Organic compounds Benzenoids Phenols Cresols Aromatic homomonocyclic compounds Benzene and substituted derivatives Hydrocarbon derivatives Organooxygen compounds Ortho cresols Aromatic homomonocyclic compound Hydrocarbon derivative Monocyclic benzene moiety O-cresol Organic oxygen compound Organooxygen compound P-cresol water_solubility 1.2 mg/mL at 25 °C logp 2.73 melting_point 73 °C logp 2.72 ALOGPS logs -1.84 ALOGPS logp 3.21 ChemAxon pka_strongest_acidic 11.07 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 2,4,6-trimethylphenol ChemAxon average_mass 136.19 ChemAxon mono_mass 136.0888 ChemAxon smiles CC1=CC(C)=C(O)C(C)=C1 ChemAxon formula C9H12O ChemAxon inchi InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3 ChemAxon inchikey BPRYUXCVCCNUFE-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 43.16 ChemAxon polarizability 16.05 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB010421 10248 10698 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:35 UTC 2020-07-31 20:34:13 UTC CDB000521 2,6-Diethylpyrazine 2,6-Diethylpyrazine belongs to the class of organic compounds known as alkylpyrazines. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. A pyrazine ring consists of a six-membered aromatic heterocycle that contains two nitrogen atoms (in positions 1 and 4) and four carbon atoms. 2,6-Diethylpyrazine is a diethylated derivative of pyrazine and it is a moderately basic compound (based on its pKa). 2,6-Diethylpyrazine has been detected, but not quantified in coffee and coffee products. Some alkylpyrazines are naturally occurring, highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions. 2,6-Diethylpyrazine has been detected in cannabis samples obtained in police seizures (PMID: 26657499) and are also constituents of Marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 2,6-Diethylpyrazine is volatilized during the combustion of cannabis. 2,6-Diethyl-pyrazine C8H12N2 136.19 136.1 2,6-diethylpyrazine 2,6-diethylpyrazine 13067-27-1 CCC1=CN=CC(CC)=N1 InChI=1S/C8H12N2/c1-3-7-5-9-6-8(4-2)10-7/h5-6H,3-4H2,1-2H3 QDWOWLUANUBTGE-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Pyrazines Organic compounds Organoheterocyclic compounds Diazines Pyrazines Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyrazine logp 1.62 ALOGPS logs -0.60 ALOGPS logp 1.2 ChemAxon pka_strongest_basic 1.8 ChemAxon iupac 2,6-diethylpyrazine ChemAxon average_mass 136.19 ChemAxon mono_mass 136.1 ChemAxon smiles CCC1=CN=CC(CC)=N1 ChemAxon formula C8H12N2 ChemAxon inchi InChI=1S/C8H12N2/c1-3-7-5-9-6-8(4-2)10-7/h5-6H,3-4H2,1-2H3 ChemAxon inchikey QDWOWLUANUBTGE-UHFFFAOYSA-N ChemAxon polar_surface_area 25.78 ChemAxon refractivity 40.18 ChemAxon polarizability 15.71 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB015755 74971 83101 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:38 UTC 2020-08-04 22:28:21 UTC CDB000522 2,6-Dimethylquinoline 2,6-Dimethylquinoline belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. 2,6-Dimethylquinoline is a dimethylated derivative of quinoline. Quinoline is a colourless hygroscopic liquid with a strong odour. 2,6-dimethylquinoline has been found in tea. It has also been detected in cannabis samples obtained in police seizures (PMID: 26657499) and it is a constituent of Marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). 2,6-Dimethylquinoline is volatilized during the combustion of cannabis. 26-Dimethyl-quinoline 26-Dimethylquinoline 2,6-Dimethyl quinoline C11H11N 157.21 157.0891 2,6-dimethylquinoline 2,6-dimethylquinoline 877-43-0 CC1=CC2=C(C=C1)N=C(C)C=C2 InChI=1S/C11H11N/c1-8-3-6-11-10(7-8)5-4-9(2)12-11/h3-7H,1-2H3 JJPSZKIOGBRMHK-UHFFFAOYSA-N belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. Quinolines and derivatives Organic compounds Organoheterocyclic compounds Quinolines and derivatives Aromatic heteropolycyclic compounds Azacyclic compounds Benzenoids Heteroaromatic compounds Hydrocarbon derivatives Methylpyridines Organonitrogen compounds Organopnictogen compounds Aromatic heteropolycyclic compound Azacycle Benzenoid Heteroaromatic compound Hydrocarbon derivative Methylpyridine Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyridine Quinoline logp 2.98 ALOGPS logs -2.28 ALOGPS logp 2.78 ChemAxon pka_strongest_basic 5.3 ChemAxon iupac 2,6-dimethylquinoline ChemAxon average_mass 157.21 ChemAxon mono_mass 157.0891 ChemAxon smiles CC1=CC2=C(C=C1)N=C(C)C=C2 ChemAxon formula C11H11N ChemAxon inchi InChI=1S/C11H11N/c1-8-3-6-11-10(7-8)5-4-9(2)12-11/h3-7H,1-2H3 ChemAxon inchikey JJPSZKIOGBRMHK-UHFFFAOYSA-N ChemAxon polar_surface_area 12.89 ChemAxon refractivity 49.61 ChemAxon polarizability 18.45 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004393 13414 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:42 UTC 2020-07-31 20:34:10 UTC CDB000523 3-(1-Methylethyl)-phenol methylcarbamate 3-(1-Methylethyl)-phenol methylcarbamate also known as m-Cumenyl methylcarbamate belongs to the class of organic compounds known as Carbamates. Carbamate is a chemical compound that is formally derived from carbamic acid (NH2COOH). 3-(1-Methylethyl)-phenol methylcarbamate is a derivative of Carbamic acid that replaced by methyl and alkyl-benzene groups. It is pure white solid without appreciable odor. Used as an insecticide to protect cotton, fruit, vegetables and field crops. As of 1998, the Environmental Protection Agency listed it as an unregistered pesticide in the United States. m-Cumenyl methylcarbamic acid 3-Isopropylphenyl methylcarbamate 3-Isopropylphenyl methylcarbamic acid C11H15NO2 193.24 193.1103 3-(propan-2-yl)phenyl N-methylcarbamate 3-isopropylphenyl N-methylcarbamate 64-00-6 CNC(=O)OC1=CC=CC(=C1)C(C)C InChI=1S/C11H15NO2/c1-8(2)9-5-4-6-10(7-9)14-11(13)12-3/h4-8H,1-3H3,(H,12,13) GYKXQTKSWLAUIT-UHFFFAOYSA-N belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Phenyl methylcarbamates Organic compounds Benzenoids Benzene and substituted derivatives Phenyl methylcarbamates Aromatic homomonocyclic compounds Carbamate esters Carbonyl compounds Cumenes Hydrocarbon derivatives Organic carbonic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Phenoxy compounds Phenylpropanes Aromatic homomonocyclic compound Carbamic acid ester Carbonic acid derivative Carbonyl group Cumene Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenoxy compound Phenyl methylcarbamate Phenylpropane logp 2.38 ALOGPS logs -2.82 ALOGPS logp 2.72 ChemAxon pka_strongest_acidic 14.77 ChemAxon iupac 3-(propan-2-yl)phenyl N-methylcarbamate ChemAxon average_mass 193.24 ChemAxon mono_mass 193.1103 ChemAxon smiles CNC(=O)OC1=CC=CC(=C1)C(C)C ChemAxon formula C11H15NO2 ChemAxon inchi InChI=1S/C11H15NO2/c1-8(2)9-5-4-6-10(7-9)14-11(13)12-3/h4-8H,1-3H3,(H,12,13) ChemAxon inchikey GYKXQTKSWLAUIT-UHFFFAOYSA-N ChemAxon polar_surface_area 38.33 ChemAxon refractivity 54.95 ChemAxon polarizability 21.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6143 M-Cumenyl methylcarbamate 1.0 2020-03-19 00:41:45 UTC 2020-07-31 20:34:10 UTC CDB000524 3-(3-Hydroxyphenyl)-2-propenoic acid, methyl ester 3-(3-Hydroxyphenyl)-2-propenoic acid, methyl ester also known as methyl trans-3-coumarate, belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 3-(3-Hydroxyphenyl)-2-propenoic acid, methyl ester is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(3-Hydroxyphenyl)-2-propenoic acid is an methylester derivative of m-coumaric acid in which the methyl group has been replaced by a hrogen atom of carboxyl functional group. M-coumaric acid is an organic compound found in carrots, strawberries, grape wines, garden tomato (var.), and bilberries. Methyl (e)-3-hydroxycinnamate Methyl trans-3-coumarate Methyl (e)-3-hydroxycinnamic acid Methyl trans-3-coumaric acid Methyl trans-3-hydroxycinnamic acid Methyl trans-3-hydroxycinnamate Methyl (2E)-3-(3-hydroxyphenyl)acrylic acid C10H10O3 178.19 178.063 methyl (2E)-3-(3-hydroxyphenyl)prop-2-enoate methyl (2E)-3-(3-hydroxyphenyl)prop-2-enoate 3943-95-1 COC(=O)\C=C\C1=CC(O)=CC=C1 InChI=1S/C10H10O3/c1-13-10(12)6-5-8-3-2-4-9(11)7-8/h2-7,11H,1H3/b6-5+ PKALKWFZXXGNJD-AATRIKPKSA-N belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Coumaric acid esters Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Carbonyl compounds Cinnamic acid esters Coumaric acids and derivatives Enoate esters Fatty acid esters Hydrocarbon derivatives Methyl esters Monocarboxylic acids and derivatives Organic oxides Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alpha,beta-unsaturated carboxylic ester Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cinnamic acid ester Coumaric acid ester Coumaric acid or derivatives Enoate ester Fatty acid ester Fatty acyl Hydrocarbon derivative Methyl ester Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Styrene logp 2.41 ALOGPS logs -2.21 ALOGPS logp 2.21 ChemAxon pka_strongest_acidic 9.4 ChemAxon pka_strongest_basic -6 ChemAxon iupac methyl (2E)-3-(3-hydroxyphenyl)prop-2-enoate ChemAxon average_mass 178.19 ChemAxon mono_mass 178.063 ChemAxon smiles COC(=O)\C=C\C1=CC(O)=CC=C1 ChemAxon formula C10H10O3 ChemAxon inchi InChI=1S/C10H10O3/c1-13-10(12)6-5-8-3-2-4-9(11)7-8/h2-7,11H,1H3/b6-5+ ChemAxon inchikey PKALKWFZXXGNJD-AATRIKPKSA-N ChemAxon polar_surface_area 46.53 ChemAxon refractivity 49.81 ChemAxon polarizability 18.54 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5352910 131393 1.0 2020-03-19 00:41:48 UTC 2020-07-31 20:34:13 UTC CDB000525 3-Ethyl-o-xylene 3-Ethyl-o-xylene belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying two methyl groups at positions 1 and 2. 3-Ethyl-o-xylene is an aromatic hydrocarbon with the formula C10H14. 3-Ethyl-o-xylene is an ethylated derivative of o-xylene in which a hydrogen atom has been substituted by the ethyl group at the position C-3 of the benzene ring. O-xylene is a colorless slightly oily flammable liquid. O-xylene is largely used in the production of phthalic anhydride, which is a precursor to many materials, drugs, and other chemicals. 3-Ethyl-o-xylene has been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). C10H14 134.22 134.1096 1-ethyl-2,3-dimethylbenzene 1,2-dimethyl-3-ethylbenzene 933-98-2 CCC1=CC=CC(C)=C1C InChI=1S/C10H14/c1-4-10-7-5-6-8(2)9(10)3/h5-7H,4H2,1-3H3 QUBBAXISAHIDNM-UHFFFAOYSA-N belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 2-positions. o-Xylenes Organic compounds Benzenoids Benzene and substituted derivatives Xylenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon O-xylene Unsaturated hydrocarbon logp 4.40 ALOGPS logs -3.83 ALOGPS logp 3.96 ChemAxon iupac 1-ethyl-2,3-dimethylbenzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CCC1=CC=CC(C)=C1C ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-4-10-7-5-6-8(2)9(10)3/h5-7H,4H2,1-3H3 ChemAxon inchikey QUBBAXISAHIDNM-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 45.78 ChemAxon polarizability 16.9 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 13621 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:53 UTC 2020-07-31 20:34:15 UTC CDB000526 m-Ethyltoluene m-Ethyltoluene belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bear a methane group. m-Ethyltoluene is an aromatic compound with the formula CH3C6H4C2H5. m-Ethyltoluene is a derivative of toluene bearing an additional ethyl substituent at position 3. There are three known ethyltoluene isomers including 3-ethyltoluene, 2-ethyltoluene and 4-Ethyltoluene. m-Ethyltoluene is a colorless liquid and it is used for the production of specialty polystyrenes. Ethyltoluenes are produced by the ethylation of toluene, over typical acid catalysts. This process gives a mixture of the 2-, 3-, and 4- isomers. m-Ethyltoluene has been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). 1-Methyl-3-ethylbenzene m-Ethylmethylbenzene m-Ethyltoluene m-Methylethylbenzene C9H12 120.19 120.0939 1-ethyl-3-methylbenzene M-ethyltoluene CCC1=CC=CC(C)=C1 InChI=1S/C9H12/c1-3-9-6-4-5-8(2)7-9/h4-7H,3H2,1-2H3 ZLCSFXXPPANWQY-UHFFFAOYSA-N belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. Toluenes Organic compounds Benzenoids Benzene and substituted derivatives Toluenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Toluene Unsaturated hydrocarbon toluenes logp 3.79 ALOGPS logs -3.32 ALOGPS logp 3.44 ChemAxon iupac 1-ethyl-3-methylbenzene ChemAxon average_mass 120.19 ChemAxon mono_mass 120.0939 ChemAxon smiles CCC1=CC=CC(C)=C1 ChemAxon formula C9H12 ChemAxon inchi InChI=1S/C9H12/c1-3-9-6-4-5-8(2)7-9/h4-7H,3H2,1-2H3 ChemAxon inchikey ZLCSFXXPPANWQY-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 40.74 ChemAxon polarizability 15.02 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12100 C14522 77512 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:41:56 UTC 2020-08-04 22:28:21 UTC CDB000527 3-Hexen-1-ol-acetate 3-Hexenyl acetate also known as 3-Hexen-1-ol-acetate, belongs to the class of organic compounds known as esters. These are carboxylic acid derivatives in which the acid hydrogen atom has been replaced by an alkyl moiety, forming an ester group. 3-Hexenyl acetate is an acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol or (E)-hex-3-en-1-ol, for this reason there are two 3-hexenyl-acetate isomers, trans- and cis-hexenyl-acetate. Cis-3-hexenyl acetate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cis-3-hexenyl acetate is a sweet, apple, and banana tasting compound and it is therefore used as a food additive. Cis-3-hexenyl acetate has been detected, but not quantified in, several different foods such as tamarinds, sunburst squash (pattypan squash), carobs, pepper (C. baccatum), and swedes. 3-Hexenyl acetate has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). (Z)-3-Hexen-1-yl acetate (Z)-3-Hexenol acetate (Z)-3-Hexenyl acetate (Z)-Hex-3-enyl acetate 3Z-Hexenyl acetate cis-3-Hexen-1-yl acetate cis-3-Hexenyl ethanoate (3Z)-Hex-3-en-1-yl acetate (Z)-3-Hexen-1-yl acetic acid (Z)-3-Hexenol acetic acid (Z)-3-Hexenyl acetic acid (Z)-Hex-3-enyl acetic acid 3Z-Hexenyl acetic acid cis-3-Hexen-1-yl acetic acid cis-3-Hexenyl ethanoic acid (3Z)-Hex-3-en-1-yl acetic acid cis-3-Hexenyl acetic acid (3Z)-3-Hexenyl acetate (Z)-3-Hexen-1-ol acetate (Z)-3-Hexen-1-yl, acetate 1-Acetate(3Z)-3-hexen-1-ol 3(Z)-Hexenyl acetate 3-Hexenol acetate, cis Acetate(3Z)-3-hexen-1-ol Acetate(Z)-3-hexen-1-ol Acetic acid cis-3-hexenyl ester cis-3-Hexen-1-ol, acetate cis-3-Hexenol acetate cis-3-Hexenyl-1-acetate cis-Hex-3-enyl acetate FEMA 3171 Hex-3(Z)-enyl acetate Z-Hex-3-en-1-yl acetate 3-Hexenylacetate 3-Hexenyl acetate cis-3-Hexenyl acetate (3Z)-Hexen-1-yl acetate (Z)-Hex-3-en-1-yl acetate 3Z-Hexen-1-ol acetate cis-3-Hexen-1-ol acetate cis-Hex-3-en-1-yl acetate C8H14O2 142.2 142.0994 (3Z)-hex-3-en-1-yl acetate (Z)-3-hexenyl acetate 3681-71-8 CC\C=C/CCOC(C)=O InChI=1S/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4- NPFVOOAXDOBMCE-PLNGDYQASA-N belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Carboxylic acid esters Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters acetate ester logp 2.47 ALOGPS logs -2.16 ALOGPS logp 1.77 ChemAxon pka_strongest_basic -7 ChemAxon iupac (3Z)-hex-3-en-1-yl acetate ChemAxon average_mass 142.2 ChemAxon mono_mass 142.0994 ChemAxon smiles CC\C=C/CCOC(C)=O ChemAxon formula C8H14O2 ChemAxon inchi InChI=1S/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4- ChemAxon inchikey NPFVOOAXDOBMCE-PLNGDYQASA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 41.6 ChemAxon polarizability 16.44 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB019927 4515742 5363388 61316 C19757 CPD-12846 C00048964 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:00 UTC 2020-07-31 20:34:13 UTC CDB000528 3-Isopropylbenzaldehyde 3-Isopropylbenzaldehyde belongs to the class of organic compounds known as cumenes. Cumenes are aromatic compounds containing a isopropylbenzene moiety. 3-Isopropylbenzaldehyde is a natural organic compound with the molecular formula C10H12O. It is a benzaldehyde with an isopropyl group in the 3-position of the benzene ring. Benzaldehyde is a colorless liquid with a characteristic almond-like odor found in natural plant foods such as almonds, apricots, apples, and cherry kernels. 3-Isopropylbenzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Isopropylbenzaldehyde is a component found in the essential oil of cinnamon (doi: 10.15414/jmbfs.2017/18.7.7.312-316). It has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). C10H12O 148.21 148.0888 3-(propan-2-yl)benzaldehyde 3-isopropylbenzaldehyde 34246-57-6 CC(C)C1=CC=CC(C=O)=C1 InChI=1S/C10H12O/c1-8(2)10-5-3-4-9(6-10)7-11/h3-8H,1-2H3 FFQXEFNKZVGJDI-UHFFFAOYSA-N belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. Cumenes Organic compounds Benzenoids Benzene and substituted derivatives Cumenes Aromatic homomonocyclic compounds Benzaldehydes Benzoyl derivatives Hydrocarbon derivatives Organic oxides Phenylpropanes Aldehyde Aromatic homomonocyclic compound Aryl-aldehyde Benzaldehyde Benzoyl Cumene Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Phenylpropane logp 2.72 ALOGPS logs -2.99 ALOGPS logp 2.93 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac 3-(propan-2-yl)benzaldehyde ChemAxon average_mass 148.21 ChemAxon mono_mass 148.0888 ChemAxon smiles CC(C)C1=CC=CC(C=O)=C1 ChemAxon formula C10H12O ChemAxon inchi InChI=1S/C10H12O/c1-8(2)10-5-3-4-9(6-10)7-11/h3-8H,1-2H3 ChemAxon inchikey FFQXEFNKZVGJDI-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 46.83 ChemAxon polarizability 16.96 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 520680 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:02 UTC 2020-08-04 22:28:21 UTC CDB000529 3-methyl-2-cyclopenten-1-one 3-Methyl-2-cyclopenten-1-one, also known as fema 3435, belongs to the class of organic compounds known as cyclic ketones. 3-Methyl-2-cyclopenten-1-one is a cyclic organic compound, containing a ketone that is conjugated to a double bond, Œ± to the carbonyl. 3-Methyl-2-cyclopenten-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-cyclopenten-1-one is a sweet, fatty, and fruity tasting compound. It has been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, pepper (C. annuum), red bell peppers, and yellow bell peppers. It has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). 1-Methyl-1-cyclopenten-3-one 3-Methyl-2-cyclopentenone 3-Methylcyclopent-2-en-1-one 3-Methylcyclopent-2-enone FEMA 3435 C6H8O 96.13 96.0575 3-methylcyclopent-2-en-1-one 2-cyclopenten-1-one, 3-methyl- 2758-18-1 CC1=CC(=O)CC1 InChI=1S/C6H8O/c1-5-2-3-6(7)4-5/h4H,2-3H2,1H3 CHCCBPDEADMNCI-UHFFFAOYSA-N belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Cyclic ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic homomonocyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic homomonocyclic compound Cyclic ketone Hydrocarbon derivative Organic oxide logp 0.48 ALOGPS logs -0.42 ALOGPS logp 1.28 ChemAxon pka_strongest_acidic 17.31 ChemAxon pka_strongest_basic -4.5 ChemAxon iupac 3-methylcyclopent-2-en-1-one ChemAxon average_mass 96.13 ChemAxon mono_mass 96.0575 ChemAxon smiles CC1=CC(=O)CC1 ChemAxon formula C6H8O ChemAxon inchi InChI=1S/C6H8O/c1-5-2-3-6(7)4-5/h4H,2-3H2,1H3 ChemAxon inchikey CHCCBPDEADMNCI-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 29.02 ChemAxon polarizability 10.64 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008156 17691 16723 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:05 UTC 2020-08-04 22:28:21 UTC CDB000530 Promecarb 3-methyl-5-(1-methylethyl)-Phenol methylcarbamate or Promecarb belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Promecarb is a very weakly acidic compound (based on its pKa). It is an odorless, colorless, crystalline solid and it was used as a non-systemic contact insecticide. Promecarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment (https://journals.flvc.org/edis/article/view/114999). Promecarb is no longer approved for sale or use in the USA. Promecarb‚Äôs mechanism of action is through the inhibition of the enzyme acetylcholine esterase. Acetylcholine esterase (ACE) is an enzyme that breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions; its breakdown allows the muscle or organ to relax. The inhibition of ACE results in the accumulation of acetyl choline at motor nerves synapses, causing overstimulation of the nicotinic and muscarinic receptors at the neuromuscular junction. Promecarb has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). 3-Methyl-5-isopropylphenyl N-methylcarbamate Carbamult m-Cym-5-yl methylcarbamate 3-Cym-5-yl methylcarbamate C12H17NO2 207.27 207.1259 3-methyl-5-(propan-2-yl)phenyl N-methylcarbamate 3-isopropyl-5-methylphenyl N-methylcarbamate 2631-37-0 CN=C(O)OC1=CC(C)=CC(=C1)C(C)C InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14) DTAPQAJKAFRNJB-UHFFFAOYSA-N belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Phenyl methylcarbamates Organic compounds Benzenoids Benzene and substituted derivatives Phenyl methylcarbamates Aromatic homomonocyclic compounds Carbamate esters Carbonyl compounds Cumenes Hydrocarbon derivatives Organic carbonic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Phenoxy compounds Phenylpropanes Toluenes Aromatic homomonocyclic compound Carbamic acid ester Carbonic acid derivative Carbonyl group Cumene Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenoxy compound Phenyl methylcarbamate Phenylpropane Toluene Carbamate insecticide alkylbenzene logp 2.82 ALOGPS logs -3.15 ALOGPS logp 3.23 ChemAxon pka_strongest_acidic 14.77 ChemAxon iupac 3-methyl-5-(propan-2-yl)phenyl N-methylcarbamate ChemAxon average_mass 207.27 ChemAxon mono_mass 207.1259 ChemAxon smiles CN=C(O)OC1=CC(C)=CC(=C1)C(C)C ChemAxon formula C12H17NO2 ChemAxon inchi InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14) ChemAxon inchikey DTAPQAJKAFRNJB-UHFFFAOYSA-N ChemAxon polar_surface_area 38.33 ChemAxon refractivity 60 ChemAxon polarizability 23.66 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 17516 C18956 Promecarb Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:07 UTC 2020-07-31 20:34:13 UTC CDB000531 3-Methylheptane 3-Methylheptane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 3-methylheptane is considered to be a hydrocarbon lipid molecule. 3-Methylheptane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 3-Methylheptane has been detected, but not quantified in, a few different foods, such as herbs and spices, pulses, and tea. This could make 3-methylheptane a potential biomarker for the consumption of these foods. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration. 3-Methylheptane is a potentially toxic compound. Petroleum distillates are also irritating to the skin. Petroleum distillate poisoning may cause nausea, vomiting, cough, pulmonary irritation progressing to pulmonary edema, bloody sputum, and bronchial pneumonia. Volatile hydrocarbons are absorbed mainly through the lungs and may also enter the body after ingestion via aspiration. Treatment is mainly symptomatic and supportive. Petroleum distillates are aspiration hazards and may cause pulmonary damage, central nervous system depression, and cardiac effects such as cardiac arrhythmias. At high amounts, central nervous system depression may also occur, with symptoms such as weakness, dizziness, slow and shallow respiration, unconsciousness, and convulsions. They may also affect the blood, immune system, liver, and kidney. C8H18 114.23 114.1409 (3R)-3-methylheptane (3R)-3-methylheptane 589-81-1 CCCC[C@H](C)CC InChI=1S/C8H18/c1-4-6-7-8(3)5-2/h8H,4-7H2,1-3H3/t8-/m1/s1 LAIUFBWHERIJIH-MRVPVSSYSA-N belongs to the class of organic compounds known as saturated hydrocarbons. These are hydrocarbons that contains only saturated carbon atoms, which are linked to one another through single bonds. These includes alkanes and cycloalkanes. Saturated hydrocarbons Organic compounds Hydrocarbons Saturated hydrocarbons Aliphatic acyclic compounds Aliphatic acyclic compound Saturated hydrocarbon logp 4.82 ALOGPS logs -4.38 ALOGPS logp 3.86 ChemAxon iupac (3R)-3-methylheptane ChemAxon average_mass 114.23 ChemAxon mono_mass 114.1409 ChemAxon smiles CCCC[C@H](C)CC ChemAxon formula C8H18 ChemAxon inchi InChI=1S/C8H18/c1-4-6-7-8(3)5-2/h8H,4-7H2,1-3H3/t8-/m1/s1 ChemAxon inchikey LAIUFBWHERIJIH-MRVPVSSYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 38.56 ChemAxon polarizability 16.07 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12263096 1.0 2020-03-19 00:42:10 UTC 2020-07-31 20:34:13 UTC CDB000532 3-Methylpentane 3-Methylpentane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. 3-Methylpentane is a branched chain alkane with the molecular formula C6H14. It is a structural isomer of hexane composed of a methyl group bonded to the third carbon atom in a pentane chain. It is of similar structure to the isomeric 2-methylpentane, which has the methyl group located on the second carbon of the pentane chain. 3-Methylpentane is possibly neutral. 3-Methylpentane is a potentially toxic compound. It causes degeneration of the peripheral nervous system (and eventually the central nervous system), starting with damage to the nerve axons. It is distributed throughout the body in the blood, and metabolized by mixed function oxidases in the liver to a number of metabolites. Certain kinds of special glues used in the roofing and shoe and leather industries also contain hexane. 3-Methyl-pentane C6H14 86.18 86.1096 3-methylpentane 3-methylpentane CCC(C)CC InChI=1S/C6H14/c1-4-6(3)5-2/h6H,4-5H2,1-3H3 PFEOZHBOMNWTJB-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane logp 3.98 ALOGPS logs -3.27 ALOGPS logp 2.97 ChemAxon iupac 3-methylpentane ChemAxon average_mass 86.18 ChemAxon mono_mass 86.1096 ChemAxon smiles CCC(C)CC ChemAxon formula C6H14 ChemAxon inchi InChI=1S/C6H14/c1-4-6(3)5-2/h6H,4-5H2,1-3H3 ChemAxon inchikey PFEOZHBOMNWTJB-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 29.36 ChemAxon polarizability 12.02 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7282 3-Methylpentane 1.0 2020-03-19 00:42:14 UTC 2020-07-31 20:34:10 UTC CDB000533 3-Pentanol 3-Pentanol, also known as (C2H5)2choh or 3-pentyl alcohol, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R, R'=alkyl, aryl). 3-Pentanol is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Pentanol is a sweet, fruit, and herbal tasting compound. 3-Pentanol has been detected, but not quantified in, prickly pears. This could make 3-pentanol a potential biomarker for the consumption of these foods. 3-Pentanol is one of eight isomers of amyl alcohol. An amyl alcohol is any of 8 alcohols with the formula C5H12O. A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterfication, by which is produced amyl acetate and other important products. The name amyl alcohol without further specification applies to the normal (straight-chain) form, 1-pentanol. (C2H5)2choh 1-Ethyl-1-propanol 3-Pentyl alcohol Diethyl carbinol Isoamyl alcohol Pentanol-3 Sec-amyl alcohol Sec-pentanol Sec-pentyl alcohol C5H12O 88.15 88.0888 pentan-3-ol 3-pentanol 584-02-1 CCC(O)CC InChI=1S/C5H12O/c1-3-5(6)4-2/h5-6H,3-4H2,1-2H3 AQIXEPGDORPWBJ-UHFFFAOYSA-N belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Secondary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic acyclic compounds Hydrocarbon derivatives Aliphatic acyclic compound Hydrocarbon derivative Secondary alcohol secondary alcohol logp 1.22 ALOGPS logs -0.12 ALOGPS logp 1.3 ChemAxon pka_strongest_acidic 18.18 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac pentan-3-ol ChemAxon average_mass 88.15 ChemAxon mono_mass 88.0888 ChemAxon smiles CCC(O)CC ChemAxon formula C5H12O ChemAxon inchi InChI=1S/C5H12O/c1-3-5(6)4-2/h5-6H,3-4H2,1-2H3 ChemAxon inchikey AQIXEPGDORPWBJ-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 26.48 ChemAxon polarizability 11 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB029632 11428 77519 3-Pentanol 1.0 2020-03-19 00:42:18 UTC 2020-07-31 20:34:13 UTC CDB000534 3,4,5-Trimethyl-1-hexene 3,4,5-Trimethyl-1-Hexene, belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds. 3,4,5-Timethyl-1-Hexene is possibly neutral. 3,4,5-Trimethyl-1-Hexene is a trimethylated derivative of 1-Hexene. 1-Hexene is an alkene that is classified in industry as higher olefin and an alpha-olefin meaning that the double bond is located at the alpha (primary) position, endowing the compound with higher reactivity and thus useful chemical properties. 1-Hexene is an industrially significant linear alpha olefin. 1-Hexene is a colourless liquid. It is used in the synthesis of flavors, perfumes, dyes and resins. C9H18 126.24 126.1409 (3S,4S)-3,4,5-trimethylhex-1-ene (3S,4S)-3,4,5-trimethylhex-1-ene 56728-10-0 CC(C)[C@H](C)[C@@H](C)C=C InChI=1S/C9H18/c1-6-8(4)9(5)7(2)3/h6-9H,1H2,2-5H3/t8-,9-/m0/s1 NLLUKGSIZLNKDD-IUCAKERBSA-N logp 3.62 ALOGPS logs -4.33 ALOGPS logp 3.69 ChemAxon iupac (3S,4S)-3,4,5-trimethylhex-1-ene ChemAxon average_mass 126.24 ChemAxon mono_mass 126.1409 ChemAxon smiles CC(C)[C@H](C)[C@@H](C)C=C ChemAxon formula C9H18 ChemAxon inchi InChI=1S/C9H18/c1-6-8(4)9(5)7(2)3/h6-9H,1H2,2-5H3/t8-,9-/m0/s1 ChemAxon inchikey NLLUKGSIZLNKDD-IUCAKERBSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.1 ChemAxon polarizability 16.64 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 1.0 2020-03-19 00:42:21 UTC 2020-07-31 20:34:13 UTC CDB000535 3,4,5-Trimethylphenol 3,4,5-Trimethylphenol, also known as 3,4,5-hemimellitenol, belongs to the class of organic compounds known as para-cresols. Para cresols are compounds containing a para-cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and a methyl group at position 4. 3,4,5-Trimethylphenol is an aromatic compound and a trimethylated derivative of Phenol. Phenol is a volatile white crystalline solid. Phenol was first extracted from coal tar, but today it is produced at a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is primarily used to synthesize plastics and related materials. 3,4,5-Trimethylphenol is a reactive species toward oxidation, for instance the Teuber reaction, 3,4,5-Trimethylphenol can be oxidized to quinone. 3,4,5-Trimethylphenol has been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499). 1-Hydroxy-3,4,5-trimethylbenzene 3,4,5-Hemimellitenol 5-Hydroxy-1,2,3-trimethylbenzene C9H12O 136.19 136.0888 3,4,5-trimethylphenol 3,4,5-trimethylphenol 527-54-8 CC1=CC(O)=CC(C)=C1C InChI=1S/C9H12O/c1-6-4-9(10)5-7(2)8(6)3/h4-5,10H,1-3H3 FDQQNNZKEJIHMS-UHFFFAOYSA-N belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4. Para cresols Organic compounds Benzenoids Phenols Cresols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Hydrocarbon derivatives Meta cresols Organooxygen compounds 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Hydrocarbon derivative M-cresol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound P-cresol phenols logp 2.77 ALOGPS logs -1.92 ALOGPS logp 3.21 ChemAxon pka_strongest_acidic 10.57 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 3,4,5-trimethylphenol ChemAxon average_mass 136.19 ChemAxon mono_mass 136.0888 ChemAxon smiles CC1=CC(O)=CC(C)=C1C ChemAxon formula C9H12O ChemAxon inchi InChI=1S/C9H12O/c1-6-4-9(10)5-7(2)8(6)3/h4-5,10H,1-3H3 ChemAxon inchikey FDQQNNZKEJIHMS-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 43.16 ChemAxon polarizability 15.94 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10696 38896 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:24 UTC 2020-07-31 20:34:13 UTC CDB000536 4-Ethoxy-3-anisaldehyde 4-Ethoxy-3-Anisaldehyde or 4-Ethoxy-3-methoxybenzaldehyde belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). 4-Ethoxy-3-methoxybenzaldehyde is isolated from storax. 4-Ethoxy-3-anisaldehyde is a sweet, floral, and vanilla tasting compound. 4-Ethoxy-3-anisaldehyde has been detected as a volatile component in Marijuana samples obtained in police seizures (PMID:26657499). 4-Ethoxy-3-anisaldehyde 4-Ethoxy-3-methoxy-benzaldehyde 4-Ethoxy-m-anisaldehyde Ethylvanillin? C10H12O3 180.2 180.0786 4-ethoxy-3-methoxybenzaldehyde ethyl-vanillin 120-25-2 CCOC1=C(OC)C=C(C=O)C=C1 InChI=1S/C10H12O3/c1-3-13-9-5-4-8(7-11)6-10(9)12-2/h4-7H,3H2,1-2H3 BERFDQAMXIBOHM-UHFFFAOYSA-N belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Benzoyl derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives Aromatic homomonocyclic compounds Alkyl aryl ethers Anisoles Benzaldehydes Hydrocarbon derivatives Methoxybenzenes Organic oxides Phenoxy compounds Aldehyde Alkyl aryl ether Anisole Aromatic homomonocyclic compound Aryl-aldehyde Benzaldehyde Benzoyl Ether Hydrocarbon derivative Methoxybenzene Organic oxide Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound water_solubility 1.16 mg/mL at 25 °C logp 1.63 melting_point 64 - 65 °C logp 2.18 ALOGPS logs -2.43 ALOGPS logp 1.73 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 4-ethoxy-3-methoxybenzaldehyde ChemAxon average_mass 180.2 ChemAxon mono_mass 180.0786 ChemAxon smiles CCOC1=C(OC)C=C(C=O)C=C1 ChemAxon formula C10H12O3 ChemAxon inchi InChI=1S/C10H12O3/c1-3-13-9-5-4-8(7-11)6-10(9)12-2/h4-7H,3H2,1-2H3 ChemAxon inchikey BERFDQAMXIBOHM-UHFFFAOYSA-N ChemAxon polar_surface_area 35.53 ChemAxon refractivity 50.32 ChemAxon polarizability 19.01 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000871 60464 67116 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:30 UTC 2020-08-04 22:28:21 UTC CDB000537 4-Methyl guaiacol 4-Methyl Guaiacol or 2-Methoxy-4-methylphenol, also known creosol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-Methyl guaiacol or Creosol is a chemical compound with the molecular formula C8H10O2. Creosol reacts with hydrogen halides to give a catechol. It is one of the components of creosote. 4-Methyl Guaiacol is a bacon, bitter, and carnation tasting compound. 4-Methyl guaiacol has been detected, but not quantified, in several different foods, such as red bell peppers, green bell peppers, orange bell peppers, corns, and pepper (c. annuum). Sources of creosol include: Coal tar, creosote wood, creosote reduction, it can be a product of vanillin using zinc powder in strong hydrochloric acid. It can be found as glycosides in green vanilla beans. It is also found in tequila. Compared with phenol, creosol is a less toxic disinfectant. 4-Methyl Guaiacol has been detected as a volatile component in Marijuana samples obtained in police seizures (PMID:26657499). 4-Methyl Guaiacol is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 1-Hydroxy-2-methoxy-4-methylbenzene 2-Hydroxy-5-methylanisole 2-Methoxy-4-cresol 2-Methoxy-4-methyl-phenol 2-Methoxy-4-methylphenol (4-methylguaiacol) 2-Methoxy-4-methylphenol (creosol) 2-Methoxy-4-methylphenol, 9ci 2-Methoxy-p-cresol 3-Methoxy-4-hydroxytoluene 3-Methoxy-4-methyl-phenol 4-Hydroxy-3-methoxy-1-methylbenzene 4-Hydroxy-3-methoxytoluene 4-Methyl guaiacol 4-Methyl-2-methoxyphenol 4-Methyl-2-methoxyphenol (4-methylguaiacol) 4-Methylguaiacol 5-Methylguaiacol Creosol Cresolum drudum FEMA 2671 Homocatechol methyl ester Homocatechol monomethyl ether Homoguaiacol Kreosol p-Creosol p-Methylguaiacol p-Methylguaicol Phenol, 4-methyl-2-methoxy Rohkcrsol Valspice C8H10O2 138.16 138.0681 2-methoxy-4-methylphenol creosol 93-51-6 COC1=C(O)C=CC(C)=C1 InChI=1S/C8H10O2/c1-6-3-4-7(9)8(5-6)10-2/h3-5,9H,1-2H3 PETRWTHZSKVLRE-UHFFFAOYSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyphenols Organic compounds Benzenoids Phenols Methoxyphenols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Para cresols Phenoxy compounds Toluenes 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound P-cresol Phenol ether Phenoxy compound Toluene melting_point 5.5 °C logp 1.79 ALOGPS logs -1.31 ALOGPS logp 2.03 ChemAxon pka_strongest_acidic 10.34 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxy-4-methylphenol ChemAxon average_mass 138.16 ChemAxon mono_mass 138.0681 ChemAxon smiles COC1=C(O)C=CC(C)=C1 ChemAxon formula C8H10O2 ChemAxon inchi InChI=1S/C8H10O2/c1-6-3-4-7(9)8(5-6)10-2/h3-5,9H,1-2H3 ChemAxon inchikey PETRWTHZSKVLRE-UHFFFAOYSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 39.54 ChemAxon polarizability 14.77 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008862 21105936 7144 Creosol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:32 UTC 2020-07-31 20:34:13 UTC CDB000538 4-Methyldecane 4-Methyldecane or xi-4-Methyldecane belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Thus, 4-MethylDecane is considered to be a hydrocarbon lipid molecule. 4-Methyldecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 4-Methyldecane has been detected, but not quantified in, a few different foods, such as cereals and cereal products, nuts, and pulses. This could make XI-4-methyldecane a potential biomarker for the consumption of these foods. 4-MethylDecane is a methylated derivative of Decane. Decane is a component of gasoline (petrol) and kerosene. Like other alkanes, it is a nonpolar solvent, does not dissolve in water, and is readily combustible. C11H24 156.31 156.1878 (4S)-4-methyldecane (4S)-4-methyldecane 2847-72-5 CCCCCC[C@@H](C)CCC InChI=1S/C11H24/c1-4-6-7-8-10-11(3)9-5-2/h11H,4-10H2,1-3H3/t11-/m0/s1 DVWZNKLWPILULD-NSHDSACASA-N belongs to the class of organic compounds known as saturated hydrocarbons. These are hydrocarbons that contains only saturated carbon atoms, which are linked to one another through single bonds. These includes alkanes and cycloalkanes. Saturated hydrocarbons Organic compounds Hydrocarbons Saturated hydrocarbons Aliphatic acyclic compounds Aliphatic acyclic compound Saturated hydrocarbon logp 6.15 ALOGPS logs -5.64 ALOGPS logp 5.2 ChemAxon iupac (4S)-4-methyldecane ChemAxon average_mass 156.31 ChemAxon mono_mass 156.1878 ChemAxon smiles CCCCCC[C@@H](C)CCC ChemAxon formula C11H24 ChemAxon inchi InChI=1S/C11H24/c1-4-6-7-8-10-11(3)9-5-2/h11H,4-10H2,1-3H3/t11-/m0/s1 ChemAxon inchikey DVWZNKLWPILULD-NSHDSACASA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 52.36 ChemAxon polarizability 22.31 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 24884415 1.0 2020-03-19 00:42:36 UTC 2020-08-04 22:28:21 UTC CDB000539 4-Methylphenethylamine 4-Methylphenethylamine also known as para-methylphenethylamine, with the chemical formula of C9H13N, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. 4-Methylphenethylamine is a very strong basic compound (based on its pKa). As its monomethylated isomers, Œ±-methylphenethylamine, Œ≤-methylphenethylamine, and N-methylphenethylamine, 4-methylphenethylamine is an agonist of the trace amine associated receptor 1 (TAAR1) in humans (PMID: 17038507). Furthermore, there is also evidence showing that 4-methylphenethylamine might inhibit the cytochrome P450 CYP1A2 and CYP2A6 enzymes, in humans. 4-Methylphenetylamine has been detected as a volatile component in Marijuana samples obtained in police seizures (PMID:26657499). C9H13N 135.21 135.1048 2-(4-methylphenyl)ethan-1-amine benzeneethanamine, 4-methyl- 3261-62-9 CC1=CC=C(CCN)C=C1 InChI=1S/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3 VKJXAQYPOTYDLO-UHFFFAOYSA-N belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Phenethylamines Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic homomonocyclic compounds 2-arylethylamines Aralkylamines Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Toluenes 2-arylethylamine Amine Aralkylamine Aromatic homomonocyclic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Phenethylamine Primary aliphatic amine Primary amine Toluene logp 1.67 ALOGPS logs -1.91 ALOGPS logp 1.9 ChemAxon pka_strongest_basic 9.81 ChemAxon iupac 2-(4-methylphenyl)ethan-1-amine ChemAxon average_mass 135.21 ChemAxon mono_mass 135.1048 ChemAxon smiles CC1=CC=C(CCN)C=C1 ChemAxon formula C9H13N ChemAxon inchi InChI=1S/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3 ChemAxon inchikey VKJXAQYPOTYDLO-UHFFFAOYSA-N ChemAxon polar_surface_area 26.02 ChemAxon refractivity 44.33 ChemAxon polarizability 16.54 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 76751 4-Methylphenethylamine Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL: Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1. J Pharmacol Exp Ther. 2007 Jan;320(1):475-85. doi: 10.1124/jpet.106.112532. Epub 2006 Oct 12. 17038507 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:38 UTC 2020-07-31 20:34:13 UTC CDB000540 4-Methylpyrimidine 4-Methylpyrimidine belongs to the class of organic compounds known as pyrimidines and pyrimidine derivatives. Pyrimidines and pyrimidine derivatives are compounds containing a pyrimidne ring, which is a six-membered aromatic heterocycle containing two nitrogen atoms (at positions 1 and 3) and four carbon atoms. 4-Methylpyrimidine is a methylated derivative of pyrimidine and it is a moderately basic compound (based on its pKa). The pyrimidine ring system has wide occurrence in nature (PMID:17191818) as substituted and ring fused compounds and derivatives, including the nucleotides cytosine, thymine and uracil, thiamine (vitamin B1) and alloxan. 4-Methylpyrimidine has also been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID:26657499). 4-Methylpyrimidine is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). C5H6N2 94.12 94.0531 4-methylpyrimidine 4-methylpyrimidine 3438-46-8 CC1=NC=NC=C1 InChI=1S/C5H6N2/c1-5-2-3-6-4-7-5/h2-4H,1H3 LVILGAOSPDLNRM-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrimidines and pyrimidine derivatives. Pyrimidines and pyrimidine derivatives are compounds containing a pyrimidne ring, which is a six-member aromatic heterocycle which consists of two nitrogen atoms (at positions 1 and 3) and four carbon atoms. Pyrimidines and pyrimidine derivatives Organic compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyrimidine logp 0.24 ALOGPS logs 0.54 ALOGPS logp 0.18 ChemAxon pka_strongest_basic 2.48 ChemAxon iupac 4-methylpyrimidine ChemAxon average_mass 94.12 ChemAxon mono_mass 94.0531 ChemAxon smiles CC1=NC=NC=C1 ChemAxon formula C5H6N2 ChemAxon inchi InChI=1S/C5H6N2/c1-5-2-3-6-4-7-5/h2-4H,1H3 ChemAxon inchikey LVILGAOSPDLNRM-UHFFFAOYSA-N ChemAxon polar_surface_area 25.78 ChemAxon refractivity 27.31 ChemAxon polarizability 9.73 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 18922 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Wiegand H, Wirz B, Schweitzer A, Gross G, Perez MI, Andres H, Kimmerlin T, Rueping M, Seebach D: Pharmacokinetic investigation of a 14C-labelled beta 3/alpha tetrapeptide in rats. Chem Biodivers. 2004 Nov;1(11):1812-28. doi: 10.1002/cbdv.200490136. 17191818 1.0 2020-03-19 00:42:42 UTC 2020-08-04 22:28:21 UTC CDB000541 4-pyridinamine 4-Aminopyridine (4-AP, fampridine, dalfampridine) is an organic compound with the chemical formula C5H4N‚ÄìNH2. The molecule is one of the three isomeric amines of pyridine. 4-Aminopyridine is an aromatic amine, constituted by a pyridine ring system, bearing a single amino substituent at position 4. 4-Aminopyridine is a potassium channel blocker used clinically to help multiple sclerosis patients walk. After a phase III trial, a 25 % improvement in walking speed and increased muscular strength was reported in multiple sclerosis patients (PMID: 24587826). It is also widely used as a research tool for the characterization of subtypes of the potassium channel (PMID: 31919372). The production of 4-aminopyridine begins with the ammoxidation of 4-methylpyridine, followed by obtainment of the nitrile. The nitrile is then used to generate the pyridine carboxamide, which undergoes a decarboxylation reaction to yield 4-aminopyridine (https://doi.org/10.1002/14356007.a22_399). 4-Aminopyridine has also been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID:26657499). 4-AP 4-Pyridinamine 4-Pyridylamine Ampyra Avitrol Fampridina Fampridine Fampridinum gamma-Aminopyridine N07XX07 p-Aminopyridine 4-Aminopyridine Neurelan Fampyra g-Aminopyridine Γ-aminopyridine Dalfampridine 4 Aminopyridine 4 Aminopyridine sustained release Pymadine Fampridine SR Fampridine-SR 4-Aminopyridine sustained release VMI 103 Sustained release, 4-aminopyridine VMI-103 C5H6N2 94.11 94.0531 1,4-dihydropyridin-4-imine 4-aminopyridine 504-24-5 N=C1C=CNC=C1 InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) NUKYPUAOHBNCPY-UHFFFAOYSA-N belongs to the class of organic compounds known as aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring. Aminopyridines and derivatives Organic compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organopnictogen compounds Primary amines Amine Aminopyridine Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Primary amine aminopyridine aromatic amine logp -0.65 ALOGPS logs -1.15 ALOGPS logp 0.29 ChemAxon pka_strongest_acidic 16.04 ChemAxon pka_strongest_basic 12.18 ChemAxon iupac 1,4-dihydropyridin-4-imine ChemAxon average_mass 94.11 ChemAxon mono_mass 94.0531 ChemAxon smiles N=C1C=CNC=C1 ChemAxon formula C5H6N2 ChemAxon inchi InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) ChemAxon inchikey NUKYPUAOHBNCPY-UHFFFAOYSA-N ChemAxon polar_surface_area 35.88 ChemAxon refractivity 40.09 ChemAxon polarizability 9.66 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB06637 1727 34385 C13728 Dalfampridine Jensen HB, Ravnborg M, Dalgas U, Stenager E: 4-Aminopyridine for symptomatic treatment of multiple sclerosis: a systematic review. Ther Adv Neurol Disord. 2014 Mar;7(2):97-113. doi: 10.1177/1756285613512712. 24587826 Rodriguez-Rangel S, Bravin AD, Ramos-Torres KM, Brugarolas P, Sanchez-Rodriguez JE: Structure-activity relationship studies of four novel 4-aminopyridine K(+) channel blockers. Sci Rep. 2020 Jan 9;10(1):52. doi: 10.1038/s41598-019-56245-w. 31919372 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:44 UTC 2020-07-31 20:34:13 UTC CDB000542 5-Ethenyl-2-methylpyridine 5-Ethenyl-2-methylpyridine or 2-Methyl-5-vinylpyridine belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. 5-Ethenyl-2-methylpyridine is a methylated derivative of Vinylpyridine. There are three known isomers of vinylpyridine including 2-, 3- and 4-vinylpyridine. Vinylpyridines are organic compounds with the chemical formula CH2CHC5H4N. In their pure form vinylpyridines are colorless liquids, although samples are often brown. Vinylpyridine has been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID:26657499) and it has also been found in marijuana smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 2-Methyl-5-vinylpyridine 2-Methyl-5-vinylpyridine hydrochloride C8H9N 119.17 119.0735 5-ethenyl-2-methylpyridine 2-methyl-5-vinylpyridine 25038-86-2 CC1=NC=C(C=C)C=C1 InChI=1S/C8H9N/c1-3-8-5-4-7(2)9-6-8/h3-6H,1H2,2H3 VJOWMORERYNYON-UHFFFAOYSA-N belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. Methylpyridines Organic compounds Organoheterocyclic compounds Pyridines and derivatives Methylpyridines Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Methylpyridine Organic nitrogen compound Organonitrogen compound Organopnictogen compound logp 1.99 ALOGPS logs -0.77 ALOGPS logp 1.62 ChemAxon pka_strongest_basic 5.56 ChemAxon iupac 5-ethenyl-2-methylpyridine ChemAxon average_mass 119.17 ChemAxon mono_mass 119.0735 ChemAxon smiles CC1=NC=C(C=C)C=C1 ChemAxon formula C8H9N ChemAxon inchi InChI=1S/C8H9N/c1-3-8-5-4-7(2)9-6-8/h3-6H,1H2,2H3 ChemAxon inchikey VJOWMORERYNYON-UHFFFAOYSA-N ChemAxon polar_surface_area 12.89 ChemAxon refractivity 38.18 ChemAxon polarizability 13.75 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 8817 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:48 UTC 2020-07-31 20:34:13 UTC CDB000543 5-Methylindane 5-Methylindane belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane ring fused to a benzene ring. 5-Methylindane is a methylated derivative of Indane. Indane or indan is an organic compound with the formula C6H4(CH2)3. It appears is a colorless liquid in its pure form. Indane is a petrochemical and it occurs at the level of about 0.1% in coal tar. It is usually produced by hydrogenation of indene. Indane is used in the synthesis of sulofenur (https://doi.org/10.1021/jm00171a013). There are four known methylindane isomers including 1-methyl-indane and 2-methyl-indane (where one methyl group is attached to the five-carbon ring), 4-methyl-indane and 5-methyl-indane (where one methyl group is attached to the benzene ring). 5-Methylindane has been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID:26657499). C10H12 132.21 132.0939 5-methyl-2,3-dihydro-1H-indene 5-methyl-2,3-dihydro-1H-indene 874-35-1 CC1=CC=C2CCCC2=C1 InChI=1S/C10H12/c1-8-5-6-9-3-2-4-10(9)7-8/h5-7H,2-4H2,1H3 RFXBCGVZEJEYGG-UHFFFAOYSA-N belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Indanes Organic compounds Benzenoids Indanes Aromatic homopolycyclic compounds Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons Aromatic homopolycyclic compound Aromatic hydrocarbon Hydrocarbon Indane Polycyclic hydrocarbon Unsaturated hydrocarbon logp 3.51 ALOGPS logs -3.58 ALOGPS logp 3.49 ChemAxon iupac 5-methyl-2,3-dihydro-1H-indene ChemAxon average_mass 132.21 ChemAxon mono_mass 132.0939 ChemAxon smiles CC1=CC=C2CCCC2=C1 ChemAxon formula C10H12 ChemAxon inchi InChI=1S/C10H12/c1-8-5-6-9-3-2-4-10(9)7-8/h5-7H,2-4H2,1H3 ChemAxon inchikey RFXBCGVZEJEYGG-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 43.98 ChemAxon polarizability 16.3 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 13402 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:51 UTC 2020-08-04 22:28:21 UTC CDB000544 5-Octanolide 5-Octanolide belongs to the class of organic compounds known as Œ¥-valerolactones. These are cyclic organic compounds containing an oxan-2-one moiety. Œ¥-Valerolactone is a lactone industrially used as a chemical intermediate in processes such as the production of polyesters. 5-Octanolide is considered to be a fatty ester lipid molecule. 5-Octanolide is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 5-Octanolide has been detected, but not quantified, in fats, oils and some fruits. 5-Octanolide has been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID: 26657499). C8H14O2 142.2 142.0994 (6S)-6-propyloxan-2-one (6S)-6-propyloxan-2-one 698-76-0 CCC[C@H]1CCCC(=O)O1 InChI=1S/C8H14O2/c1-2-4-7-5-3-6-8(9)10-7/h7H,2-6H2,1H3/t7-/m0/s1 FYTRVXSHONWYNE-ZETCQYMHSA-N belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Delta valerolactones Organic compounds Organoheterocyclic compounds Lactones Delta valerolactones Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Oxanes Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Delta valerolactone Delta_valerolactone Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Oxane logp 2.08 ALOGPS logs -1.78 ALOGPS logp 1.98 ChemAxon pka_strongest_basic -7 ChemAxon iupac (6S)-6-propyloxan-2-one ChemAxon average_mass 142.2 ChemAxon mono_mass 142.0994 ChemAxon smiles CCC[C@H]1CCCC(=O)O1 ChemAxon formula C8H14O2 ChemAxon inchi InChI=1S/C8H14O2/c1-2-4-7-5-3-6-8(9)10-7/h7H,2-6H2,1H3/t7-/m0/s1 ChemAxon inchikey FYTRVXSHONWYNE-ZETCQYMHSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 38.45 ChemAxon polarizability 16.03 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7269403 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:42:55 UTC 2020-07-31 20:34:11 UTC CDB000545 7-Methoxycoumarin 7-Methoxycoumarin or Herniarin, also known as ayapanin is a methoxy derivative of coumarin or a methyl derivative of umbelliferone. It belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 7-Methoxycoumarin is a neutral, hydrophobic molecule that is not soluble in water. It exists as a white to pale yellow powder. It has a pleasant balsamic, sweet or tonka taste/odor. 7-Methoxycoumarin is used as a scent or aroma agent in perfumes, lotions, facial moisturizers, hand creams, hair conditioners, household aerosols, lip balms and baby oils. 7-Methoxycoumarin occurs naturally in many plants and foods and has been detected, but not quantified in, several different plants, such as hemp, barley, tarragons, roman camomiles, fruits, and wild celeries. This could make 7-methoxycoumarin a potential biomarker for the consumption of these foods. 7-Methoxy-2H-1-benzopyran-2-one 7-Methoxycoumarin Ayapanin Herniarine Methylumbelliferone 7-(Methyloxy)-2H-chromen-2-one 7-Methoxy-2H-1-benzopyran-2-one, 9ci 7-Methoxy-2H-chromen-2-one 7-Methoxy-coumarin 7-METHOXYCOURMARIN 7-Methyl ether derivative OF umbelliferone Coumarin, 7-methoxy- (8ci) Herniarin (6ci) Methyl umbelliferyl ether Umbelliferone methyl ether C10H8O3 176.17 176.0473 7-methoxy-2H-chromen-2-one methylumbelliferone 531-59-9 COC1=CC2=C(C=CC(=O)O2)C=C1 InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3 LIIALPBMIOVAHH-UHFFFAOYSA-N belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Coumarins and derivatives Organic compounds Phenylpropanoids and polyketides Coumarins and derivatives Aromatic heteropolycyclic compounds 1-benzopyrans Alkyl aryl ethers Anisoles Heteroaromatic compounds Hydrocarbon derivatives Lactones Organic oxides Oxacyclic compounds Pyranones and derivatives 1-benzopyran Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Coumarin Ether Heteroaromatic compound Hydrocarbon derivative Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Pyran Pyranone coumarins coumarins water_solubility 0.133 mg/mL melting_point 117 - 118 °C logp 1.88 ALOGPS logs -2.55 ALOGPS logp 1.63 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 7-methoxy-2H-chromen-2-one ChemAxon average_mass 176.17 ChemAxon mono_mass 176.0473 ChemAxon smiles COC1=CC2=C(C=CC(=O)O2)C=C1 ChemAxon formula C10H8O3 ChemAxon inchi InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3 ChemAxon inchikey LIIALPBMIOVAHH-UHFFFAOYSA-N ChemAxon polar_surface_area 35.53 ChemAxon refractivity 48.01 ChemAxon polarizability 17.43 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000963 10295 10748 5679 C09268 C00002476 Herniarin Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Cheriyan BV Sr, Kadhirvelu P Sr, Nadipelly J Jr, Shanmugasundaram J, Sayeli V Sr, Subramanian V Sr: Anti-nociceptive Effect of 7-methoxy Coumarin from Eupatorium Triplinerve vahl (Asteraceae). Pharmacogn Mag. 2017 Jan-Mar;13(49):81-84. doi: 10.4103/0973-1296.197650. 28216887 Kielbus M, Skalicka-Wozniak K, Grabarska A, Jeleniewicz W, Dmoszynska-Graniczka M, Marston A, Polberg K, Gawda P, Klatka J, Stepulak A: 7-substituted coumarins inhibit proliferation and migration of laryngeal cancer cells in vitro. Anticancer Res. 2013 Oct;33(10):4347-56. 24123002 1.0 2020-03-19 00:42:57 UTC 2020-07-08 16:06:18 UTC CDB000546 Acetamide Acetamide, also known as ethanamid or acetic acid amide, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH. Acetamide is soluble in water and low molecular mass alcohols. It forms deliquescent hexagonal crystals that are odorless when pure (DOI: 10.1002/14356007.a01_045.pub3), but it frequently has a mousy odor. Pure acetamide has a bitter taste. Acetamide is used as a solvent and as a plasticizer (DOI:10.1002/14356007.a01_045.pub3). Acetamide has been classified by the International Agency for Research on Cancer (IARC) as a Group 2B possible human carcinogen (PMID: 10507919). However, further studies need to be conducted to better understand the potential in vivo genotoxicity of acetamide (PMID: 31470077). It has also been investigated as a residue from some pesticides and as an impurity in the manufacture of pharmaceuticals (DOI: 10.1021/op200205b). Acetamide has been identified in milk, eggs, and meat (PMID: 29186951). It has also been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID: 26657499). Acetamid Acetic acid amide Azetamid CH3CONH2 Essigsaeureamid Ethanamid Ethanamide Methanecarboxamide Acetate amide Acetimidic acid ACM Amid kyseliny octove Acetamide, monosodium salt C2H5NO 59.07 59.0371 acetamide acetamide 60-35-5 CC(O)=N InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) DLFVBJFMPXGRIB-UHFFFAOYSA-N belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Carboximidic acids Organic compounds Organic acids and derivatives Carboximidic acids and derivatives Carboximidic acids Aliphatic acyclic compounds Hydrocarbon derivatives Organonitrogen compounds Organooxygen compounds Organopnictogen compounds Aliphatic acyclic compound Carboximidic acid Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound a small molecule carboximidic acid water_solubility 2250 mg/mL at 25 °C logp -1.26 melting_point 82 - 83 °C boiling_point 221.2 °C Wikipedia logp -1.10 ALOGPS logs 0.80 ALOGPS logp -1 ChemAxon pka_strongest_acidic 16.75 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac acetamide ChemAxon average_mass 59.07 ChemAxon mono_mass 59.0371 ChemAxon smiles CC(O)=N ChemAxon formula C2H5NO ChemAxon inchi InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) ChemAxon inchikey DLFVBJFMPXGRIB-UHFFFAOYSA-N ChemAxon polar_surface_area 43.09 ChemAxon refractivity 14.47 ChemAxon polarizability 5.76 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB02736 173 178 FDB008298 27856 C06244 Acetamide Authors unspecified: Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide. Proceedings of the IARC Working Group on the Evaluation of Carcinogenic Risks to Humans. Lyon, France, 17-24 February 1998. IARC Monogr Eval Carcinog Risks Hum. 1999;71 Pt 1:1-315. 10507919 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Vismeh R, Haddad D, Moore J, Nielson C, Bals B, Campbell T, Julian A, Teymouri F, Jones AD, Bringi V: Exposure Assessment of Acetamide in Milk, Beef, and Coffee Using Xanthydrol Derivatization and Gas Chromatography/Mass Spectrometry. J Agric Food Chem. 2018 Jan 10;66(1):298-305. doi: 10.1021/acs.jafc.7b02229. Epub 2017 Dec 27. 29186951 Moore MM, Gollapudi B, Nagane R, Khan N, Patel M, Khanvilkar T, Roy AM, Ramesh E, Bals B, Teymouri F, Nault R, Bringi V: The food contaminant acetamide is not an in vivo clastogen, aneugen, or mutagen in rodent hematopoietic tissue. Regul Toxicol Pharmacol. 2019 Nov;108:104451. doi: 10.1016/j.yrtph.2019.104451. Epub 2019 Aug 27. 31470077 1.0 2020-03-19 00:43:02 UTC 2020-07-24 23:30:08 UTC CDB000547 Acetic acid Acetic acid, also known as acetATE ion or ethanoat, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Acetic acid is a drug. Acetic acid is a weakly acidic compound (based on its pKa). ACETATE ion Acetic acid, ion(1-) Azetat CH3-COO(-) Ethanoat Ethanoate MeCO2 anion ACETic acid ion Acetate, ion(1-) Ethanoic acid Acetic acid Acetate VoSoL C2H3O2 59.04 59.0133 acetate acetate 758-12-3 CC([O-])=O InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)/p-1 QTBSBXVTEAMEQO-UHFFFAOYSA-M belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Carboxylic acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acids Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic anions Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic anion Organic oxide Organic oxygen compound Organooxygen compound a carboxylate monocarboxylic acid anion water_solubility Miscible Wikipedia logp -0.28 Wikipedia melting_point 16 to 17 °C Wikipedia boiling_point 118 to 119 °C Wikipedia logp -0.29 ALOGPS logs 0.80 ALOGPS logp -0.22 ChemAxon pka_strongest_acidic 4.54 ChemAxon iupac acetate ChemAxon average_mass 59.04 ChemAxon mono_mass 59.0133 ChemAxon smiles CC([O-])=O ChemAxon formula C2H3O2 ChemAxon inchi InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)/p-1 ChemAxon inchikey QTBSBXVTEAMEQO-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 23.48 ChemAxon polarizability 4.96 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB030644 DBMET01513 175 30089 ACET Acetate 1.0 2020-03-19 00:43:06 UTC 2020-07-10 00:17:45 UTC CDB000548 Acetophenone Acetophenone, also known as 1-phenylethanone or acetylbenzene, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. The chemical formula of acetophenone is C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is used as a flavouring ingredient for fruit flavours and as a leavening agent. Acetophenone is also the starting material for the synthesis of some pharmaceuticals and is listed as an approved excipient by the U.S. FDA. Acetophenone is currently listed as a Group D carcinogen indicating that it does not produce carcinogenic effects in humans. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes. Acetophenone is found in many foods, some of which are chicory, spearmint, watermelon, rocket salad, and pepper (spice), apple, cheese, apricot, banana, beef, and cauliflower. Acetophenone has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) and is a constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). Acetophenone is volatilized during the combustion of cannabis. 1-Phenylethanone Acetylbenzene Benzoyl methide Methyl phenyl ketone Phenyl methyl ketone 1-Phenyl-1-ethanone 1-Phenyl-ethanone 1-Phenylethan-1-one 1-Phenylethanone (acetophenone) 1-Phenylethanone, 9ci Acetofenon Acetophenon Acetyl-benzene Acetylbenzol alpha-Acetophenone Benzoylmethide Dymex FEMA 2009 Hypnon Hypnone Ketone, methyl phenyl Methyl phenyl-ketone Methylphenylketone Nchem.180-comp5 Phenyl Phenylethanone Phenylmethylketone C8H8O 120.15 120.0575 1-phenylethan-1-one acetophenone 98-86-2 CC(=O)C1=CC=CC=C1 InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 KWOLFJPFCHCOCG-UHFFFAOYSA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic homomonocyclic compounds Acetophenones Aryl alkyl ketones Benzoyl derivatives Hydrocarbon derivatives Organic oxides Acetophenone Alkyl-phenylketone Aromatic homomonocyclic compound Aryl alkyl ketone Benzenoid Benzoyl Hydrocarbon derivative Monocyclic benzene moiety Organic oxide a methyl-ethyl-ketone acetophenones an aromatic compound water_solubility 6.13 mg/mL at 25 °C logp 1.58 melting_point 20 °C boiling_point 202 °C Wikipedia logp 1.65 ALOGPS logs -1.95 ALOGPS logp 1.53 ChemAxon pka_strongest_acidic 16.1 ChemAxon pka_strongest_basic -7.4 ChemAxon iupac 1-phenylethan-1-one ChemAxon average_mass 120.15 ChemAxon mono_mass 120.0575 ChemAxon smiles CC(=O)C1=CC=CC=C1 ChemAxon formula C8H8O ChemAxon inchi InChI=1S/C8H8O/c1-7(9)8-5-3-2-4-6-8/h2-6H,1H3 ChemAxon inchikey KWOLFJPFCHCOCG-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 36.46 ChemAxon polarizability 13.05 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB04619 FDB012106 7132 7410 AC0 C07113 27632 Acetophenone C00002685 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:08 UTC 2020-06-29 20:41:08 UTC CDB000549 Acrolein Acrolein, also known as propenal or acrylic aldehyde, belongs to the class of organic compounds known as enals. These are alpha, beta unsaturated aldehydes, with the general chemical formula RC=C-CH=O in which the aldehydic C=O function is conjugated to the C=C double bond located at the alpha beta position. Acrolein is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. Acrolein is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine. Acrolein is used as an etherification agent in the preparation of modified food starches. It is also used as an herbicide and algicide in water treatment. It can be produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and, due to its reactivity it shows high toxicity. It is a good Michael acceptor, making it a useful reaction tool with thiols. It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including lyral, norbornene-2-carboxaldehyde, and myrac aldehyde. Acrolein is toxic and is a strong irritant to the skin, eyes, and nasal passages. The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a 'tolerable oral acrolein intake' of 7.5 mg/day per kilogram of body weight. Although acrolein occurs in French fries, the levels are only a few micrograms per kilogram. Acrolein has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Acrolein is found in fruit aromas, black tea, carrot, cooked potato, cheeses, white wine, hydrolyzed soy protein, turkey, pork, beef fat and other foods. Acrolein has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Acrylaldehyde Acrylic aldehyde Propenal 2-Propen-1-one 2-Propenal 2-Propenaldehyde Acquinite Acraldehyde Acroleina Aldehyde, acrylic Aldehyde, allyl Aldehyde, ethylene Allyl aldehyde Aqualin Aqualine Biocide CH2=chcho Crolean Ethylene aldehyde Magnacide Magnacide H Magnacide H and b Papite Prop-2-en-1-al Prop-2-enal Propenaldehyde Propylene aldehyde Slimicide trans-Acrolein formylethylene 2 Propenal C3H4O 56.06 56.0262 prop-2-enal acrolein 107-02-8 C=CC=O InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2 HGINCPLSRVDWNT-UHFFFAOYSA-N belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. Enals Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Short-chain aldehydes Aldehyde Aliphatic acyclic compound Enal Hydrocarbon derivative Organic oxide Short-chain aldehyde Pesticides a small molecule enal water_solubility 212 mg/mL at 25 °C logp -0.01 melting_point -87.7 °C boiling_point 53 °C Wikipedia logp 0.18 ALOGPS logs 0.28 ALOGPS logp 0.37 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac prop-2-enal ChemAxon average_mass 56.06 ChemAxon mono_mass 56.0262 ChemAxon smiles C=CC=O ChemAxon formula C3H4O ChemAxon inchi InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2 ChemAxon inchikey HGINCPLSRVDWNT-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 16.37 ChemAxon polarizability 5.58 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C01471 FDB008307 7559 7847 15368 ACROLEIN Acrolein Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. 22626821 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:11 UTC 2020-07-24 23:30:19 UTC CDB000550 Alloaromadendrene Alloaromadendrene or Aromadendrene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Aromadendrene is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Aromadendrene is a neutral, hydrophobic molecule that is largely insoluble in water. It exists as a colorless, clear liquid. Aromadendrene has a woody, musty odor. It is found in a number of plants and spices including allspice, anise fruit, cloves, eucalyptus, ginger, guava, marjoram, oregano, rosemary, sage, thyme and the essential oil of indigenous cinnamon. Alloaromadendrene is also found in cannabis plants, but only in trace amounts (PMID: 6991645). Alloaromadendrene appears to exhibit antioxidant activity and has been shown to delay aging in C. elegans (PMID: 24918691). C15H24 204.36 204.1878 (1aR,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene (1aR,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-octahydro-1aH-cyclopropa[e]azulene 25246-27-9 C[C@@H]1CC[C@H]2[C@H]1[C@H]1[C@@H](CCC2=C)C1(C)C InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14-/m1/s1 ITYNGVSTWVVPIC-XGFWRYKXSA-N belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5,10-cycloaromadendrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Guaianes Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons 5,10-cycloaromadendrane sesquiterpenoid Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Guaiane sesquiterpenoid Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 3.70 ALOGPS logs -4.94 ALOGPS logp 4.15 ChemAxon iupac (1aR,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CC[C@H]2[C@H]1[C@H]1[C@@H](CCC2=C)C1(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14-/m1/s1 ChemAxon inchikey ITYNGVSTWVVPIC-XGFWRYKXSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.7 ChemAxon polarizability 25.96 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12305247 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Yu CW, Li WH, Hsu FL, Yen PL, Chang ST, Liao VH: Essential oil alloaromadendrene from mixed-type Cinnamomum osmophloeum leaves prolongs the lifespan in Caenorhabditis elegans. J Agric Food Chem. 2014 Jul 2;62(26):6159-65. doi: 10.1021/jf500417y. Epub 2014 Jun 23. 24918691 1.0 2020-03-19 00:43:16 UTC 2020-07-31 20:34:11 UTC CDB000552 alpha-Bulnescene alpha-Bulnescene or Guaia-1(10),11-diene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Bulnescene is possibly neutral. C15H24 204.36 204.1878 (3R,3aS,5S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene (1R,7S,8aS)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,5,6,7,8,8a-octahydroazulene C[C@@H]1CCC2=C(C)CC[C@@H](C[C@@H]12)C(C)=C InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h12-13,15H,1,5-9H2,2-4H3/t12-,13+,15+/m1/s1 YHAJBLWYOIUHHM-IPYPFGDCSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.61 ALOGPS logs -3.97 ALOGPS logp 4.46 ChemAxon iupac (3R,3aS,5S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CCC2=C(C)CC[C@@H](C[C@@H]12)C(C)=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h12-13,15H,1,5-9H2,2-4H3/t12-,13+,15+/m1/s1 ChemAxon inchikey YHAJBLWYOIUHHM-IPYPFGDCSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.26 ChemAxon polarizability 26.26 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 91753506 1.0 2020-03-19 00:43:19 UTC 2020-08-04 22:28:21 UTC CDB000553 alpha-Cedrene Œ±-Cedrene also known as Cedrene, belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ±-Cedrene is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Œ±-Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known cedrene isomers, namely Œ±- and Œ≤-cedrene, which differ in the position of a double bond. Œ±-Cedrene has been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645; PMID: 26657499). b-Cedrene Β-cedrene Cedrone alpha-Cedrene Cedrene C15H24 204.35 204.1878 (1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane (1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane 546-28-1 C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CCC3=C InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1 DYLPEFGBWGEFBB-OSFYFWSMSA-N belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Cedrane and isocedrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cedrane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 4.50 ALOGPS logs -5.19 ALOGPS logp 4.16 ChemAxon iupac (1S,2R,5S,7S)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0^{1,5}]undecane ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CCC3=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1 ChemAxon inchikey DYLPEFGBWGEFBB-OSFYFWSMSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.62 ChemAxon polarizability 25.66 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006258 11106485 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. 23746261 1.0 2020-03-19 00:43:29 UTC 2020-08-04 22:28:21 UTC CDB000555 alpha-Ionol Œ±-Ionol or 4,7-megastigmadien-9-ol, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ±-Ionol is a colorless liquid with a floral, woody odor and has a sweet, berry taste. It is used as a flavoring ingredient and as a food additive [EAFUS]. Œ±-Ionol has been found in grapes and raspberries. Œ±-Ionol has been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645; PMID: 26657499). C13H22O 194.32 194.1671 (2S,3E)-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-ol (2S,3E)-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-ol 472-78-6 C[C@H](O)\C=C\[C@@H]1C(C)=CCCC1(C)C InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,11-12,14H,5,9H2,1-4H3/b8-7+/t11-,12+/m0/s1 PWDOJWCZWKWKSE-ADYIUWEDSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homomonocyclic compound Cyclofarsesane sesquiterpenoid Hydrocarbon derivative Ionone derivative Megastigmane sesquiterpenoid Organic oxygen compound Organooxygen compound Secondary alcohol Sesquiterpenoid logp 4.10 ALOGPS logs -3.15 ALOGPS logp 3.09 ChemAxon pka_strongest_acidic 16.91 ChemAxon pka_strongest_basic -2 ChemAxon iupac (2S,3E)-4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-ol ChemAxon average_mass 194.32 ChemAxon mono_mass 194.1671 ChemAxon smiles C[C@H](O)\C=C\[C@@H]1C(C)=CCCC1(C)C ChemAxon formula C13H22O ChemAxon inchi InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,11-12,14H,5,9H2,1-4H3/b8-7+/t11-,12+/m0/s1 ChemAxon inchikey PWDOJWCZWKWKSE-ADYIUWEDSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 63.09 ChemAxon polarizability 23.94 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 76958571 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:31 UTC 2020-08-04 22:28:21 UTC CDB000556 alpha-Methylcinnamaldehyde Œ±-Methylcinnamaldehyde belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. Œ±-Methylcinnamaldehyde has a cinnamon, balsamic odor with a spicy, sweet and woody taste. Œ±-Methylcinnamaldehyde is a methylated, more stable, derivative of cinnamaldehyde. Cinnamaldehyde is a pale yellow, viscous liquid which occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90 % cinnamaldehyde. Cinnamaldehyde was first isolated from cinnamon essential oil in 1834 and was first synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854. Œ±-Methylcinnamaldehyde has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) C10H10O 146.19 146.0732 (2E)-2-methyl-3-phenylprop-2-enal 2-propenal, 2-methyl-3-phenyl- 101-39-3 C\C(C=O)=C/C1=CC=CC=C1 InChI=1S/C10H10O/c1-9(8-11)7-10-5-3-2-4-6-10/h2-8H,1H3/b9-7+ VLUMOWNVWOXZAU-VQHVLOKHSA-N belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. Cinnamaldehydes Organic compounds Phenylpropanoids and polyketides Cinnamaldehydes Aromatic homomonocyclic compounds Aldehydes Benzene and substituted derivatives Enals Hydrocarbon derivatives Organic oxides Aldehyde Alpha,beta-unsaturated aldehyde Aromatic homomonocyclic compound Benzenoid Carbonyl group Cinnamaldehyde Enal Hydrocarbon derivative Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound logp 2.31 ALOGPS logs -2.64 ALOGPS logp 2.37 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac (2E)-2-methyl-3-phenylprop-2-enal ChemAxon average_mass 146.19 ChemAxon mono_mass 146.0732 ChemAxon smiles C\C(C=O)=C/C1=CC=CC=C1 ChemAxon formula C10H10O ChemAxon inchi InChI=1S/C10H10O/c1-9(8-11)7-10-5-3-2-4-6-10/h2-8H,1H3/b9-7+ ChemAxon inchikey VLUMOWNVWOXZAU-VQHVLOKHSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 46.49 ChemAxon polarizability 16.34 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5372813 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:39 UTC 2020-09-11 20:08:28 UTC CDB000558 alpha-Terpineol Œ±-Terpineol, also known as terpineol or p-menth-1-en-8-ol, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and an isopropyl group at positions 1 and 4 of ring, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are three known terpineol isomers including Œ±, Œ≤, and Œ≥-terpineol, with the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with Œ±-terpineol as the major constituent. Alpha-Terpineol is a very hydrophobic molecule, practically insoluble in water, but soluble in organic solvents such as methanol, ethanol and ethylacetate. Terpineol has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. Œ±-Terpineol has also been detected as a volatile component of cannabis plants (PMID: 6991645, 26657499). (+)-p-Menth-1-en-8-ol (1R)-alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol (R)-alpha,alpha,4-Trimethylcyclohex-3-ene-1-methanol (R)-alpha-Terpineol (+)-alpha-Terpineol (1R)-a,a,4-Trimethyl-3-cyclohexene-1-methanol (1R)-Α,α,4-trimethyl-3-cyclohexene-1-methanol (R)-a,a,4-Trimethylcyclohex-3-ene-1-methanol (R)-Α,α,4-trimethylcyclohex-3-ene-1-methanol (R)-a-Terpineol (R)-Α-terpineol (+)-a-Terpineol (+)-Α-terpineol a-Terpineol Α-terpineol (6R)-p-Menth-1-en-8-ol (R)-(+)-alpha-Terpineol (R)-2-(4-Methyl-3-cyclohexenyl)isopropanol (R)-p-Menth-1-en-8-ol (S)-(-)-p-Menth-1-en-8-ol 1-alpha-Terpineol 2-(4-Methyl-3-cyclohexen-1-yl)-2-propanol 2-(4-Methylcyclohex-3-en-1-yl)propan-2-ol 2-(4-Methylcyclohex-3-enyl)propan-2-ol (alpha-terpineol) 2-[(1R)-4-Methylcyclohex-3-en-1-yl]propan-2-ol alpha,alpha,4-Trimethyl-3-cyclohexene-1-methanol alpha-Terpinenol alpha-Terpineole alpha-Terpinol L-alpha-Terpineol Lily OF valley Terpenol Terpineol Terpineol schlechthin DL-alpha-Terpineol alpha-Terpineol, sodium salt p-Menth-1-en-8-ol D-alpha-Terpineol (S)-a-Terpineol (S)-Α-terpineol alpha-Terpineol C10H18O 154.25 154.1358 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol (+)-α-terpineol 7785-53-7 CC1=CC[C@@H](CC1)C(C)(C)O InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1 WUOACPNHFRMFPN-VIFPVBQESA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Hydrocarbon derivatives Monocyclic monoterpenoids Tertiary alcohols Alcohol Aliphatic homomonocyclic compound Hydrocarbon derivative Monocyclic monoterpenoid Organic oxygen compound Organooxygen compound P-menthane monoterpenoid Tertiary alcohol Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids alpha-terpineol water_solubility 0.71 mg/mL at 25 °C logp 2.98 LI,J & PERDUE,EM (1995) melting_point 37.5 °C logp 3.17 ALOGPS logs -2.00 ALOGPS logp 2.17 ChemAxon pka_strongest_acidic 19.4 ChemAxon pka_strongest_basic -0.87 ChemAxon iupac 2-[(1R)-4-methylcyclohex-3-en-1-yl]propan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1=CC[C@@H](CC1)C(C)(C)O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3/t9-/m0/s1 ChemAxon inchikey WUOACPNHFRMFPN-VIFPVBQESA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 48.46 ChemAxon polarizability 19.07 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 390927 FDB014552 442501 C09902 300 C00029674 Terpineol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:42 UTC 2020-08-04 22:28:21 UTC CDB000559 o-Xylene Ortho-xylene, o-xylene or 1,2-dimethylbenzen is a member of the class of organic compounds called xylenes. Xylenes are aromatic compounds that contain a benzene ring carrying two methyl groups at different positions around the ring. There are three types of xylene isomers, ortho, meta and para xylene. O-Xylene is a clear, colorless, highly flammable liquid that is not soluble in water. Most o-xylene is produced through the cracking of peteroleum. O-xylene is largely used in the production of phthalic anhydride, which is a precursor to many materials, drugs, and other chemicals (doi:10.1002/14356007.a28_433). O-Xylene has a geranium-like odor. In the plant kingdom o-xylene is found in black walnuts and papaya. It has also been detected, but not quantified in several different foods, such as pepper (C. annuum), green bell peppers, parsley, yellow bell peppers, and red bell peppers. Exposure to xylene can occur via inhalation, ingestion, eye or skin contact. It is primarily metabolized in the liver by oxidation of a methyl group and conjugation with glycine to yield methyl hippuric acid, which is then excreted in the urine. Smaller amounts are eliminated unchanged in the exhaled air (PMID: 21180450). If xylene is ingested one's mouth should be rinsed, and vomiting should not be induced. Exposure of pure xylene to eyes can cause redness and pain. Xylenes are not acutely toxic, for example the LD50 (rat, oral) is 4300 mg/kg. o-Xylene is one of the aromatic benzenoids identified in Cannabis sativa (PMID: 6991645). 1,2-Dimethylbenzene 1,2-Dimethylbenzol 2-Xylene 3,4-Xylene O-Dimethylbenzene O-Methyltoluene O-Xylol ORTHO-xylene 1,2-Xylene C8H10 106.17 106.0783 1,2-xylene ortho-xylene CC1=CC=CC=C1C InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 CTQNGGLPUBDAKN-UHFFFAOYSA-N belongs to the class of organic compounds known as o-xylenes. These are aromatic compounds that contain a o-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 2-positions. o-Xylenes Organic compounds Benzenoids Benzene and substituted derivatives Xylenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon O-xylene Unsaturated hydrocarbon an aromatic compound xylene logp 3.16 ALOGPS logs -2.71 ALOGPS logp 3 ChemAxon iupac 1,2-xylene ChemAxon average_mass 106.17 ChemAxon mono_mass 106.0783 ChemAxon smiles CC1=CC=CC=C1C ChemAxon formula C8H10 ChemAxon inchi InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 ChemAxon inchikey CTQNGGLPUBDAKN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 36.14 ChemAxon polarizability 12.96 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6967 7237 FDB005819 C07212 CPD-1421 O-Xylene 28063 Kandyala R, Raghavendra SP, Rajasekharan ST: Xylene: An overview of its health hazards and preventive measures. J Oral Maxillofac Pathol. 2010 Jan;14(1):1-5. doi: 10.4103/0973-029X.64299. 21180450 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:49 UTC 2020-08-04 22:28:21 UTC CDB000561 Aromadendrene Aromadendrene or Alloaromadendrene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Aromadendrene is possibly neutral. Aromadendrene is one of the terpenoids that are found in the cannabis plant only in trace amount. (PMID: 6991645) C15H24 204.36 204.1878 (1aR,4aR,7S,7aR,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene (1aR,4aR,7S,7aR,7bS)-1,1,7-trimethyl-4-methylidene-octahydro-1aH-cyclopropa[e]azulene 25246-27-9 C[C@H]1CC[C@@H]2[C@@H]1[C@H]1[C@@H](CCC2=C)C1(C)C InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12+,13+,14+/m0/s1 ITYNGVSTWVVPIC-ODXJTPSBSA-N belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5,10-cycloaromadendrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Guaianes Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons 5,10-cycloaromadendrane sesquiterpenoid Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Guaiane sesquiterpenoid Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 3.70 ALOGPS logs -4.94 ALOGPS logp 4.15 ChemAxon iupac (1aR,4aR,7S,7aR,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H]1CC[C@@H]2[C@@H]1[C@H]1[C@@H](CCC2=C)C1(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12+,13+,14+/m0/s1 ChemAxon inchikey ITYNGVSTWVVPIC-ODXJTPSBSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.7 ChemAxon polarizability 25.98 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 91753588 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:43:51 UTC 2020-08-04 22:28:21 UTC CDB000562 Benzaldehyde Benzaldehyde, also known as benzenecarbonal or benzenemethylal, belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Benzaldehyde is a colorless liquid with a characteristic almond-like odor. It is a strong, sweet, and almond tasting compound. Benzaldehyde is found, on average, in the highest concentration within a few different foods, such as black walnuts, almonds, and corns and in a lower concentration in safflowers, kohlrabis, and ceylon cinnamons. Benzaldehyde has also been detected, but not quantified in, Mexican oregano, winter savories, strawberries, lingonberries, and common persimmons. Benzaldehyde has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Benzaldehyde is an aromatic aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance. It is currently used in only seven cosmetic products, with the highest reported used concentration of 0.5 %, in perfumes. Benzaldehyde is a ‚ÄúGenerally Regarded As Safe‚Äù (GRAS) food additive in the U.S.A. and is accepted as a flavoring substance in the European Union. Although there is limited data available in regards of potential skin irritation and sensitization caused by benzaldehyde, the available data on the safety of the use of benzoic acid is currently used to support the safe use of benzaldehyde. (PMID: 16835129, Int J Toxicol. 2006;25 Suppl 1:11-27.). This is because benzaldehyde rapidly metabolizes to benzoic acid in the skin, rendering the available dermal irritation and sensitization data on the latter sufficient to support the safety of Benzaldehyde. Benzaldehyde is absorbed through the skin and by the lungs, distributes to all well-perfused organs, but does not accumulate in any specific tissue type. After being metabolized to benzoic acid, conjugates are formed with glycine or glucuronic acid, and excreted in the urine. Several studies have suggested that benzaldehyde can have carcinostatic or antitumor properties (https://doi.org/10.1080/00021369.1978.10863185). Overall, at the concentrations used in cosmetics, benzaldehyde is not considered a carcinogenic risk to humans. Artificial almond oil Benzanoaldehyde Benzene carbaldehyde Benzene carboxaldehyde Benzenecarbonal Benzenecarboxaldehyde Benzenemethylal Benzoic acid aldehyde Benzoic aldehyde Benzylaldehyde Ethereal oil OF bitter almonds Phenylformaldehyde Phenylmethanal Synthetic oil OF bitter almond Benzoate aldehyde Almond artificial essential oil Artificial bitter almond oil Artificial essential oil OF almond Benzadehyde Benzaldehyde FFC Benzene methylal Benzoate Benzoic acid Benzoyl hydride Benzyaldehyde BEZ Caswell no. 076 FEMA no. 2127 Oil OF bitter almond Phenylmethanal benzenecarboxaldehyde Benzaldehyde, formyl-(14)C-labeled C7H6O 106.12 106.0419 benzaldehyde benzaldehyde 100-52-7 O=CC1=CC=CC=C1 InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H HUMNYLRZRPPJDN-UHFFFAOYSA-N belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-). Benzoyl derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoyl derivatives Aromatic homomonocyclic compounds Benzaldehydes Hydrocarbon derivatives Organic oxides Aldehyde Aromatic homomonocyclic compound Aryl-aldehyde Benzaldehyde Benzoyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound an aryl aldehyde benzaldehydes water_solubility 6.95 mg/mL at 25 °C logp 1.48 HANSCH,C ET AL. (1995) melting_point -26 °C boiling_point 178.1 °C Wikipedia logp 1.60 ALOGPS logs -1.29 ALOGPS logp 1.69 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac benzaldehyde ChemAxon average_mass 106.12 ChemAxon mono_mass 106.0419 ChemAxon smiles O=CC1=CC=CC=C1 ChemAxon formula C7H6O ChemAxon inchi InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H ChemAxon inchikey HUMNYLRZRPPJDN-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 32.64 ChemAxon polarizability 11.02 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB014661 235 240 C00261 17169 BENZALDEHYDE C00034452 Benzaldehyde Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Andersen A: Final report on the safety assessment of benzaldehyde. Int J Toxicol. 2006;25 Suppl 1:11-27. doi: 10.1080/10915810600716612. 16835129 1.0 2020-03-19 00:43:55 UTC 2020-08-04 22:28:22 UTC CDB000563 Benzonitrile Benzonitrile, also known as cyanobenzene or phenyl cyanide, belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet almond odour. It is mainly used as a precursor to the resin benzoguanamine. Benzonitrile is a rancid tasting compound and it has been detected, but not quantified, in a few different foods, such as cherry and garden tomato. Benzonitrile is a potentially toxic compound to humans. Benzonitrile is a useful solvent and a versatile precursor to many derivatives such as benzamides and Diphenylketimine. It is produced by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at 400 to 450 ¬∞C (752 to 842 ¬∞F) (doi:10.1002/14356007.a03_555). Benzonitrile has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) and is a constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). Benzonitrile is volatilized during the combustion of cannabis. Benzenenitrile Benzoic acid nitrile C6H5-CN Cyanobenzene Phenyl cyanide Benzoate nitrile C7H5N 103.12 103.0422 benzonitrile benzonitrile 100-47-0 N#CC1=CC=CC=C1 InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H JFDZBHWFFUWGJE-UHFFFAOYSA-N belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent. Benzonitriles Organic compounds Benzenoids Benzene and substituted derivatives Benzonitriles Aromatic homomonocyclic compounds Hydrocarbon derivatives Nitriles Organopnictogen compounds Aromatic homomonocyclic compound Benzonitrile Carbonitrile Hydrocarbon derivative Nitrile Organic nitrogen compound Organonitrogen compound Organopnictogen compound benzenes nitrile water_solubility <0.5 g/100 mL at 22 °C Wikipedia melting_point −13 °C Wikipedia boiling_point 188 to 191 °C Wikipedia logp 1.55 ALOGPS logs -1.05 ALOGPS logp 1.83 ChemAxon iupac benzonitrile ChemAxon average_mass 103.12 ChemAxon mono_mass 103.0422 ChemAxon smiles N#CC1=CC=CC=C1 ChemAxon formula C7H5N ChemAxon inchi InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H ChemAxon inchikey JFDZBHWFFUWGJE-UHFFFAOYSA-N ChemAxon polar_surface_area 23.79 ChemAxon refractivity 31.78 ChemAxon polarizability 10.83 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB029710 7505 C09814 27991 CPD-15582 Benzonitrile Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:43:58 UTC 2020-08-04 22:28:22 UTC CDB000564 Benzophenone Benzophenone, also known as alpha-oxoditane or diphenyl ketone, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. The chemical formula of benzophenone is (C6H5)2CO, generally abbreviated to Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is found in fruits, such as grapes. It is used as an additive in flavorings or perfumes for "sweet-woody-geranium‚Äù-like notes. Benzophenone is a common photosensitizer in photochemistry. It crosses from the S1 state into the triplet state with nearly 100% efficiency. The resulting diradical will subtract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. Benzophenone can be used as a photo initiator in UV-curing applications such as inks, imaging, and clear coatings in the printing industry. Benzophenone can also serve as a preservative from ultraviolet (UV) light, preventing damage to scents and colors in products such as perfumes and soaps. Although it is considered as "essentially nontoxic‚Äù, benzophenone has been found to be an endocrine disruptor capable of binding to the pregnane X receptor (PMID: 14613717). Benzophenone has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) and is a constituent of marijuana smoke (https://doi.org/10.1007/978-1-59259-947-9_2). alpha-Oxodiphenylmethane alpha-Oxoditane Benzoylbenzene Diphenyl ketone DIPHENYLMETHANONE PH2CO a-Oxodiphenylmethane Α-oxodiphenylmethane a-Oxoditane Α-oxoditane 1DZP Adjutan 6016 ADK stab 1413 alpha -Oxodiphenylmethane alpha -Oxoditane Benzopheneone BENZOPHENONE (8ci) Benzophenone (diphenyl-ketone) Benzoyl-benzene BZQ Di(phenyl)methanone Diphenyl-methanon Diphenyl-methanone Diphenylketone Diphenylmethanone, 9ci FEMA 2134 Kayacure BP Ketone, diphenyl METHANONE, diphenyl- (9ci) Phenyl ketone C13H10O 182.22 182.0732 diphenylmethanone benzophenone 119-61-9 O=C(C1=CC=CC=C1)C1=CC=CC=C1 InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H RWCCWEUUXYIKHB-UHFFFAOYSA-N belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Benzophenones Organic compounds Benzenoids Benzene and substituted derivatives Benzophenones Aromatic homomonocyclic compounds Aryl-phenylketones Benzoyl derivatives Diphenylmethanes Hydrocarbon derivatives Organic oxides Aromatic homomonocyclic compound Aryl ketone Aryl-phenylketone Benzophenone Benzoyl Diphenylmethane Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound benzophenones water_solubility 0.137 mg/mL at 25 °C logp 3.18 melting_point 26 °C boiling_point 305.4 °C Wikipedia logp 3.03 ALOGPS logs -3.66 ALOGPS logp 3.43 ChemAxon pka_strongest_basic -7.5 ChemAxon iupac diphenylmethanone ChemAxon average_mass 182.22 ChemAxon mono_mass 182.0732 ChemAxon smiles O=C(C1=CC=CC=C1)C1=CC=CC=C1 ChemAxon formula C13H10O ChemAxon inchi InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H ChemAxon inchikey RWCCWEUUXYIKHB-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 56.63 ChemAxon polarizability 20.19 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB01878 FDB008753 2991 BZQ 3102 41308 C06354 Benzophenone Mikamo E, Harada S, Nishikawa J, Nishihara T: Endocrine disruptors induce cytochrome P450 by affecting transcriptional regulation via pregnane X receptor. Toxicol Appl Pharmacol. 2003 Nov 15;193(1):66-72. doi: 10.1016/j.taap.2003.08.001. 14613717 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:01 UTC 2020-07-31 20:34:13 UTC CDB000565 Benzphetamine Benzphetamine, also known as didrex, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Benzphetamine is a very strong basic compound (based on its pKa). Benzphetamine is a potentially toxic compound. It is a sympathomimetic agent with properties similar to dextroamphetamine. Benzphetamine is a drug used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222). Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals in the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors. Benzphetamine is only found in individuals that have used or taken this drug. Interestingly, benzphetamine has been reported to be detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499) (+)-Benzphetamine (+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine (+)-N-Benzyl-N,alpha-dimethylphenethylamine (AlphaS)-N,alpha-dimethylphenethylamine (S)-(+)-Benzphetamine (S)-(+)-N-Benzyl-N,alpha-dimethylphenethylamine (S)-Benzphetamine Benzaphetamine Benzfetamina Benzfetamine Benzfetaminum Benzylamphetamine D-N-Methyl-N-benzyl-beta-phenylisopropylamine N-Methyl-1-phenyl-N-(phenylmethyl)propan-2-amine (+)-N,a-Dimethyl-N-(phenylmethyl)-benzeneethanamine (+)-N,Α-dimethyl-N-(phenylmethyl)-benzeneethanamine (+)-N-Benzyl-N,a-dimethylphenethylamine (+)-N-Benzyl-N,α-dimethylphenethylamine (AlphaS)-N,a-dimethylphenethylamine (AlphaS)-N,α-dimethylphenethylamine (S)-(+)-N-Benzyl-N,a-dimethylphenethylamine (S)-(+)-N-Benzyl-N,α-dimethylphenethylamine D-N-Methyl-N-benzyl-b-phenylisopropylamine D-N-Methyl-N-benzyl-β-phenylisopropylamine Pfizer brand OF benzfetamine hydrochloride Didrex C17H21N 239.36 239.1674 benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine benzphetamine 156-08-1 C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1 InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1 YXKTVDFXDRQTKV-HNNXBMFYSA-N belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Amphetamines and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic homomonocyclic compounds Aralkylamines Benzylamines Hydrocarbon derivatives Organopnictogen compounds Phenylmethylamines Phenylpropanes Trialkylamines Amine Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Benzylamine Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Phenylmethylamine Phenylpropane Tertiary aliphatic amine Tertiary amine amphetamines tertiary amine water_solubility 2.33e-02 g/L logp 4.1 melting_point 152 - 153 °C logp 3.72 ALOGPS logs -4.01 ALOGPS logp 4.34 ChemAxon pka_strongest_basic 9.72 ChemAxon iupac benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine ChemAxon average_mass 239.36 ChemAxon mono_mass 239.1674 ChemAxon smiles C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1 ChemAxon formula C17H21N ChemAxon inchi InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1 ChemAxon inchikey YXKTVDFXDRQTKV-HNNXBMFYSA-N ChemAxon polar_surface_area 3.24 ChemAxon refractivity 78.39 ChemAxon polarizability 29.03 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB00865 5311017 4470556 3044 C07538 Benzphetamine Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:09 UTC 2020-07-07 15:59:36 UTC CDB000567 Benzyl formate Benzyl formate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl formate is an aromatic compound with the molecular formula C8H8O2. Benzyl formate is an almond, apricot, and black tea tasting compound. It is used in perfumery and food flavouring. Benzyl formate has been detected, but not quantified, in a few different foods, such as coffee and coffee products, fruits, and tea. Benzyl formate has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Benzyl formic acid Benzyl alcohol, formate Benzyl formiat Benzyl methanoate Benzylester kyseliny mravenci BZO Carbobenzoxy group CBZ FEMA 2145 Formic acid benzyl ester Formic acid, benzyl ester Formic acid, phenylmethyl ester Phenylmercury stearate Phenylmethyl formate PHQ Benzylformic acid Formate benzyl ester Benzyl formate C8H8O2 136.15 136.0524 benzyl formate benzyl formate 104-57-4 O=COCC1=CC=CC=C1 InChI=1S/C8H8O2/c9-7-10-6-8-4-2-1-3-5-8/h1-5,7H,6H2 UYWQUFXKFGHYNT-UHFFFAOYSA-N belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyloxycarbonyls Organic compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls Aromatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aromatic homomonocyclic compound Benzyloxycarbonyl Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound a carboxylic ester carboxylic ester logp 1.72 ALOGPS logs -1.79 ALOGPS logp 1.6 ChemAxon pka_strongest_basic -6.8 ChemAxon iupac benzyl formate ChemAxon average_mass 136.15 ChemAxon mono_mass 136.0524 ChemAxon smiles O=COCC1=CC=CC=C1 ChemAxon formula C8H8O2 ChemAxon inchi InChI=1S/C8H8O2/c9-7-10-6-8-4-2-1-3-5-8/h1-5,7H,6H2 ChemAxon inchikey UYWQUFXKFGHYNT-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 37.53 ChemAxon polarizability 13.97 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C05613 7422 DB04569 FDB021450 7708 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:14 UTC 2020-08-04 22:28:22 UTC CDB000568 Benzyl nitrile Benzyl nitrile or Benzeneacetonitrile, also known as benzyl cyanide or alpha-cyanotoluene, belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group. Benzeneacetonitrile is found, on average, in the highest concentration within kohlrabis and peppermints. Benzeneacetonitrile has also been detected, but not quantified, in several different foods, such as cabbages, cauliflowers, garden and cherry tomato. Benzeneacetonitrile has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). It is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Benzeneacetonitrile is a potentially toxic compound. Benzyl nitrile is a colorless oily aromatic liquid and an important precursor to numerous compounds in organic chemistry. Benzyl nitrile is a useful precursor to numerous drugs with recreational use potential. Benzyl nitrile can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide and by oxidative decarboxylation of phenylalanine. (Cyanomethyl)benzene 2-Phenylacetonitrile alpha-Cyanotoluene alpha-Tolunitrile Benzyl cyanide Benzyl nitrile a-Cyanotoluene Α-cyanotoluene a-Tolunitrile Α-tolunitrile .omega.-cyanotoluene Acetic acid, phenyl-nitrile alpha -Cyanotoluene alpha -Tolunitrile alpha-Cyano-toluene Benzeneacetonitrile, 9ci Benzylkyanid Benzylnitrile Cyanophenylmethane Enzylcyanide Laquo omegaraquo -cyanotoluene Omega-cyanotoluene Phenacetonitrile Phenyl acetyl nitrile Phenyl-acetonitrile Phenylacetonitrile Phenylacetonitrile, liquid Benzeneacetonitrile C8H7N 117.15 117.0578 2-phenylacetonitrile phenylacetonitrile 140-29-4 N#CCC1=CC=CC=C1 InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 SUSQOBVLVYHIEX-UHFFFAOYSA-N belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group. Benzyl cyanides Organic compounds Benzenoids Benzene and substituted derivatives Benzyl cyanides Aromatic homomonocyclic compounds Hydrocarbon derivatives Nitriles Organopnictogen compounds Aromatic homomonocyclic compound Benzyl-cyanide Carbonitrile Hydrocarbon derivative Nitrile Organic nitrogen compound Organonitrogen compound Organopnictogen compound a small molecule benzenes nitrile water_solubility 0.1 mg/mL at 25 °C logp 1.56 melting_point -23.8 °C logp 1.42 ALOGPS logs -1.23 ALOGPS logp 1.67 ChemAxon pka_strongest_acidic 14.33 ChemAxon iupac 2-phenylacetonitrile ChemAxon average_mass 117.15 ChemAxon mono_mass 117.0578 ChemAxon smiles N#CCC1=CC=CC=C1 ChemAxon formula C8H7N ChemAxon inchi InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2 ChemAxon inchikey SUSQOBVLVYHIEX-UHFFFAOYSA-N ChemAxon polar_surface_area 23.79 ChemAxon refractivity 36.34 ChemAxon polarizability 12.75 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012457 13839308 8794 C16074 25979 C00007674 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:16 UTC 2020-08-04 22:28:22 UTC CDB000569 beta-Cedrene Œ≤-Cedrene, also known as cedrone, is a member of the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ≤-Cedrene is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Œ≤-Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known cedrene isomers, namely Œ±- and Œ≤-cedrene, which differ in the position of a double bond. Œ≤-Cedrene has been found in sweet basil and it has also been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645; PMID: 26657499). (-)-alpha-Cedrene (1S,2R,5S,7S)-2,6,6,8-Tetramethyltricyclo[5.3.1.0(1,5)]undec-8-ene [3R-(3alpha,3Abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene (-)-a-Cedrene (-)-Α-cedrene [3R-(3a,3Abeta,7b,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene [3R-(3Α,3abeta,7β,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulene a-Cedrene Α-cedrene alpha-Cedrene beta-Cedrene Cedrone Cedrene C15H24 204.35 204.1878 (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene 469-61-4 C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC=C3C InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1 IRAQOCYXUMOFCW-OSFYFWSMSA-N belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Cedrane and isocedrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cedrane sesquiterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Cedrane and isocedrane sesquiterpenoids bridged compound polycyclic olefin sesquiterpene logp 5.18 ALOGPS logs -5.11 ALOGPS logp 4.1 ChemAxon iupac (1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene ChemAxon average_mass 204.35 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC=C3C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1 ChemAxon inchikey IRAQOCYXUMOFCW-OSFYFWSMSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.69 ChemAxon polarizability 25.63 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 4936353 FDB003904 10216 6431015 C09630 C00003111 CPD-8776 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:23 UTC 2020-08-04 22:28:22 UTC CDB000571 beta-Irone Œ≤-Irone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-Irone is an isomer of Irone. Irones typically have a sweet floral, iris, woody, ionone, odor. Œ≤-Irone has been detected as a volatile component in cannabis plant samples (PMID: 26657499). (+)-b-Irone (+)-Β-irone C14H22O 206.33 206.1671 (3E)-4-[(5R)-2,5,6,6-tetramethylcyclohex-1-en-1-yl]but-3-en-2-one (3E)-4-[(5R)-2,5,6,6-tetramethylcyclohex-1-en-1-yl]but-3-en-2-one 35124-15-3 C[C@@H]1CCC(C)=C(\C=C\C(C)=O)C1(C)C InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h8-9,11H,6-7H2,1-5H3/b9-8+/t11-/m1/s1 BGKCUGPVLVNPSG-ANYFNZRUSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Acryloyl compounds Enones Hydrocarbon derivatives Ketones Organic oxides Acryloyl-group Aliphatic homomonocyclic compound Alpha,beta-unsaturated ketone Carbonyl group Cyclofarsesane sesquiterpenoid Enone Hydrocarbon derivative Ionone derivative Ketone Megastigmane sesquiterpenoid Organic oxide Organic oxygen compound Organooxygen compound Sesquiterpenoid logp 4.29 ALOGPS logs -3.48 ALOGPS logp 3.56 ChemAxon pka_strongest_acidic 19.71 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac (3E)-4-[(5R)-2,5,6,6-tetramethylcyclohex-1-en-1-yl]but-3-en-2-one ChemAxon average_mass 206.33 ChemAxon mono_mass 206.1671 ChemAxon smiles C[C@@H]1CCC(C)=C(\C=C\C(C)=O)C1(C)C ChemAxon formula C14H22O ChemAxon inchi InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h8-9,11H,6-7H2,1-5H3/b9-8+/t11-/m1/s1 ChemAxon inchikey BGKCUGPVLVNPSG-ANYFNZRUSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 66.37 ChemAxon polarizability 25.15 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 10219919 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:26 UTC 2020-07-07 15:59:39 UTC CDB000572 Beta-maaliene Beta-maaliene belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Beta-maalinene is a sesquiterpenoid found in the essential oil from root of Dahurian angelica (PMID: 21657081) and also as a volatile component of cannabis samples (PMID: 26657499). b-Maaliene Β-maaliene C15H24 204.36 204.1878 (1aR,3aS,7bS)-1,1,3a,7-tetramethyl-1H,1aH,2H,3H,3aH,4H,5H,6H,7bH-cyclopropa[a]naphthalene (1aR,3aS,7bS)-1,1,3a,7-tetramethyl-1aH,2H,3H,4H,5H,6H,7bH-cyclopropa[a]naphthalene CC1=C2[C@H]3[C@@H](CC[C@]2(C)CCC1)C3(C)C InChI=1S/C15H24/c1-10-6-5-8-15(4)9-7-11-13(12(10)15)14(11,2)3/h11,13H,5-9H2,1-4H3/t11-,13-,15+/m1/s1 UPGLJTCDRBIZKP-KYOSRNDESA-N belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 4.51 ALOGPS logs -4.25 ALOGPS logp 4.06 ChemAxon iupac (1aR,3aS,7bS)-1,1,3a,7-tetramethyl-1H,1aH,2H,3H,3aH,4H,5H,6H,7bH-cyclopropa[a]naphthalene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC1=C2[C@H]3[C@@H](CC[C@]2(C)CCC1)C3(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-6-5-8-15(4)9-7-11-13(12(10)15)14(11,2)3/h11,13H,5-9H2,1-4H3/t11-,13-,15+/m1/s1 ChemAxon inchikey UPGLJTCDRBIZKP-KYOSRNDESA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 65.43 ChemAxon polarizability 25.77 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 132831 101596917 C00029818 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Zhao A, Yang X, Yang X, Wang W, Tao H: [GC-MS analysis of essential oil from root of Angelica dahurica cv. Qibaizhi]. Zhongguo Zhong Yao Za Zhi. 2011 Mar;36(5):603-7. 21657081 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:28 UTC 2020-09-11 20:08:25 UTC CDB000573 beta-Myrcene Œ≤-Myrcene or myrcene is an acyclic monoterpene. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Œ≤-Myrcene is a significant component of the essential oil of several plants, including allspice, bay, cannabis, hops, houttuynia, lemon grass, mango, myrcia, verbena, west indian bay tree, and cardamom. It is also the main component of wild thyme, the leaves of which contain up to 40% by weight of myrcene. Industrially, it is produced mainly semi-synthetically from myrcia, from which it gets its name. Myrcene has been detected as a volatile component in cannabis plant samples (PMID: 26657499) and its essential oils (PMID: 6991645). Œ≤-Myrcene is the most abundant monoterpene in Cannabis and it has analgesic, anti-inflammatory, antibiotic, and antimutagenic activities. Œ≤-Myrcene is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Œ≤-Myrcene is a flavouring agent and it is used in the perfumery industry. It has a pleasant odor but is rarely used directly. It is a key intermediate in the production of several fragrances such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. 7-Methyl-3-methyleneocta-1,6-diene Myrcene 2-Methyl-6-methylene-2,7-octadiene 3-Methylene-7-methyl-1, 6-octadiene 3-Methylene-7-methyl-1,6-octadiene 7-Methyl-3-methylene-1,6-octadiene (beta -myrcene) 7-Methyl-3-methylene-1,6-octadiene (myrcene) 7-Methyl-3-methylene-octa-1,6-diene 7-Methyl-3-methyleneoctadiene-(1,6) 7-Methyl-3-methylideneocta-1,6-diene b-Geraniolene b-Myrcene beta-Mircene beta-Myrcene FEMA 2762 2-Methyl-6-methylene-1,7-octadiene β-Myrcene 7-Methyl-3-methylene-1,6-octadiene beta-Geraniolene β-Geraniolene C10H16 136.24 136.1252 7-methyl-3-methylideneocta-1,6-diene α-myrcene 123-35-3 CC(C)=CCCC(=C)C=C InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3 UAHWPYUMFXYFJY-UHFFFAOYSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Alkatrienes Branched unsaturated hydrocarbons Unsaturated aliphatic hydrocarbons Acyclic monoterpenoid Acyclic olefin Aliphatic acyclic compound Alkatriene Branched unsaturated hydrocarbon Hydrocarbon Olefin Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes a monoterpenoid monoterpene water_solubility 0.0056 mg/mL at 25 °C logp 4.17 melting_point < -10 °C logp 4.32 ALOGPS logs -3.25 ALOGPS logp 3.54 ChemAxon iupac 7-methyl-3-methylideneocta-1,6-diene ChemAxon average_mass 136.24 ChemAxon mono_mass 136.1252 ChemAxon smiles CC(C)=CCCC(=C)C=C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3 ChemAxon inchikey UAHWPYUMFXYFJY-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 48.38 ChemAxon polarizability 17.53 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB017400 C06074 17221 31253 28993 C00000853 CPD-4888 Myrcene Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. 17467679 1.0 2020-03-19 00:44:33 UTC 2020-08-04 22:28:22 UTC CDB000575 beta-Chamigrene Œ≤-Chamigrene, also known as (S)-isochamigrene or chamigrene, belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Chamigranes have predominantly been isolated from algae, although they have also been reported to occur in plants. Œ≤-chamigrene has been found in lovage and in cannabis samples (PMID: 26657499). C15H24 204.36 204.1878 (6S)-3,7,7-trimethyl-11-methylidenespiro[5.5]undec-2-ene (+)-β-chamigrene 18431-82-8 CC1=CC[C@]2(CC1)C(=C)CCCC2(C)C InChI=1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h7H,2,5-6,8-11H2,1,3-4H3/t15-/m0/s1 WLNGPDPILFYWKF-HNNXBMFYSA-N logp 6.03 ALOGPS logs -5.08 ALOGPS logp 4.53 ChemAxon iupac (6S)-3,7,7-trimethyl-11-methylidenespiro[5.5]undec-2-ene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles CC1=CC[C@]2(CC1)C(=C)CCCC2(C)C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h7H,2,5-6,8-11H2,1,3-4H3/t15-/m0/s1 ChemAxon inchikey WLNGPDPILFYWKF-HNNXBMFYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.38 ChemAxon polarizability 25.75 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:36 UTC 2020-06-29 20:41:10 UTC CDB000576 Betahistine Betahistine belongs to the class of organic compounds known as aminoalkylpyridines. Aminoalkylpyridines are molecules that include a pyridine substituted by a 2-(methylamino)ethyl group at position 2. Betahistine is an antivertigo drug first used for treating vertigo associated with Meniere's disease. It is also commonly used for patients with balance disorders. Betahistine is only found in individuals that have used or taken this drug. Betahistine primarily acts as a histamine H1-agonist with 0.07 times the activity of histamine. Stimulating the H1-receptors in the inner ear causes a vasodilatory effect and increased permeability in the blood vessels which results in reduced endolymphatic pressure. Betahistine is believed to act by reducing the asymmetrical functioning of sensory vestibular organs as well as by increasing vestibulocochlear blood flow. Doing so aids in decreasing symptoms of vertigo and balance disorders. Betahistine also acts as a histamine H3-receptor antagonist which causes an increased output of histamine from histaminergic nerve endings which can further increase the direct H1-agonist activity. Furthermore, H3-receptor antagonism increases the levels of neurotransmitters such as serotonin in the brainstem, which inhibits the activity of vestibular nuclei, helping to restore proper balance and decrease in vertigo symptoms. Betahistine has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 2-(beta-Methylaminoethyl)pyridine 2-[2-(Methylamino)ethyl]pyridine [2-(2-Pyridyl)ethyl]methylamine Betahistina Betahistinum N-Methyl-2-(2-pyridinyl)ethanamine N-Methyl-2-pyridineethanamine Vestibo 2-(b-Methylaminoethyl)pyridine 2-(Β-methylaminoethyl)pyridine Betahistin stada Betahistine mesylate Betahistine methanesulphonate Betavert By vertin Dihydrobromide, betahistine Ergha brand OF betahistine hydrochloride Mesylate, betahistine Serc Solvay brand OF betahistine hydrochloride Stadapharm brand OF betahistine mesylate Vertigon Betahistin al Betahistin ratiopharm Betahistine methanesulfonate By-vertin Dexo brand OF betahistine mesylate Dihydrochloride, betahistine Eurim brand OF betahistine hydrochloride Hennig brand OF betahistine mesylate Medopharm brand OF betahistine mesylate Melopat Unimed brand OF betahistine hydrochloride Aequamen Altana pharma brand OF betahistine mesylate Betahistine dihydrobromide Betaserc Bouchara brand OF betahistine hydrochloride Fides ecopharma brand OF betahistine hydrochloride Fidium Methanesulfonate, betahistine Methanesulphonate, betahistine Ribrain Ratiopharm brand OF betahistine mesylate Aliud brand OF betahistine mesylate Betahistin-ratiopharm Betahistine biphar Betahistine dihydrochloride Betahistine hydrochloride Byk gulden brand OF betahistine hydrochloride Extovyl Gerard brand OF betahistine hydrochloride Hydrochloride, betahistine Lectil Mersilon PT 9 PT-9 PT9 Vasomotal C8H12N2 136.19 136.1 methyl[2-(pyridin-2-yl)ethyl]amine betahistine 5638-76-6 CNCCC1=CC=CC=N1 InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3 UUQMNUMQCIQDMZ-UHFFFAOYSA-N belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Aralkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aromatic heteromonocyclic compounds Azacyclic compounds Dialkylamines Heteroaromatic compounds Hydrocarbon derivatives Organopnictogen compounds Pyridines and derivatives Aralkylamine Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organoheterocyclic compound Organopnictogen compound Pyridine Secondary aliphatic amine Secondary amine aminoalkylpyridine secondary amino compound logp 0.59 ALOGPS logs -0.44 ALOGPS logp 0.63 ChemAxon pka_strongest_basic 9.77 ChemAxon iupac methyl[2-(pyridin-2-yl)ethyl]amine ChemAxon average_mass 136.19 ChemAxon mono_mass 136.1 ChemAxon smiles CNCCC1=CC=CC=N1 ChemAxon formula C8H12N2 ChemAxon inchi InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3 ChemAxon inchikey UUQMNUMQCIQDMZ-UHFFFAOYSA-N ChemAxon polar_surface_area 24.92 ChemAxon refractivity 41.33 ChemAxon polarizability 15.85 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB06698 2276 35677 2366 Betahistine Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:39 UTC 2020-06-29 20:41:10 UTC CDB000577 Betazole Betazole, also known as histalog or 96791, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. Betazole is a histamine H2 agonist, which is used clinically to test gastric secretory function. Gastritis can be diagnosed given late absence of gastric acid which is unresponsive to betazole stimulation. In humans, betazole is involved in betazole action pathway. Betazole can be used as a gastric secretory stimulant instead of histamine with the advantage of not provoking side effects and thus not requiring the use of antihistaminic compounds. Betazole is only found in individuals that have used or taken this drug. Surprisingly, betazole has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 1H-Pyrazole-3-ethanamine 2-(1H-Pyrazol-5-yl)ethanamine 2-(3-Pyrazolyl)ethylamine 3-(2-Aminoethyl)pyrazole 3-(beta-Aminoethyl)pyrazole Ametazole Betazol Betazolum 3-(b-Aminoethyl)pyrazole 3-(Β-aminoethyl)pyrazole Betazolo Histalog 96791, Lilly Lilly 96791 Betazole monohydrochloride Monohydrochloride, betazole Betazole dihydrochloride Dihydrochloride, betazole C5H9N3 111.15 111.0796 2-(1H-pyrazol-3-yl)ethan-1-amine betazole 105-20-4 NCCC1=NNC=C1 InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8) JXDFEQONERDKSS-UHFFFAOYSA-N belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 2-arylethylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aromatic heteromonocyclic compounds Aralkylamines Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Pyrazoles 2-arylethylamine Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Organoheterocyclic compound Organopnictogen compound Primary aliphatic amine Pyrazole primary amino compound pyrazoles water_solubility 1.56e+02 g/L logp 0.1 melting_point < 25 °C logp -0.64 ALOGPS logs 0.15 ALOGPS logp -0.28 ChemAxon pka_strongest_acidic 15.16 ChemAxon pka_strongest_basic 9.56 ChemAxon iupac 2-(1H-pyrazol-3-yl)ethan-1-amine ChemAxon average_mass 111.15 ChemAxon mono_mass 111.0796 ChemAxon smiles NCCC1=NNC=C1 ChemAxon formula C5H9N3 ChemAxon inchi InChI=1S/C5H9N3/c6-3-1-5-2-4-7-8-5/h2,4H,1,3,6H2,(H,7,8) ChemAxon inchikey JXDFEQONERDKSS-UHFFFAOYSA-N ChemAxon polar_surface_area 54.7 ChemAxon refractivity 32.4 ChemAxon polarizability 12.05 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB00272 7455 59170 7741 Betazole Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:41 UTC 2020-07-24 23:30:08 UTC CDB000578 Butane Butane, also known as N-butane belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Butane is possibly neutral. Butane is a gas at room temperature and atmospheric pressure. Butanes are highly flammable, colorless, easily liquefied gases that quickly vaporize at room temperature. It was discovered by the chemist Edward Frankland in 1849. It was found dissolved in crude petroleum in 1864 by Edmund Ronalds, who was the first to describe its properties. There are two known structural isomers of Butane including n-Butane and iso-Butane. Normal butane can be used for gasoline blending, as a fuel gas, fragrance extraction solvent, either alone or in a mixture with propane, and as a feedstock for the manufacture of ethylene and butadiene, a key ingredient of synthetic rubber. Inhalation of butane can cause euphoria, drowsiness, unconsciousness, asphyxia, cardiac arrhythmia, fluctuations in blood pressure and temporary memory loss, when abused directly from a highly pressurized container, and can result in death from asphyxiation and ventricular fibrillation. e 943a e-943a e943a N-Butan N-Butane N-C4H10 R-600 C4H10 58.12 58.0783 butane butane 106-97-8 CCCC InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3 IJDNQMDRQITEOD-UHFFFAOYSA-N belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Acyclic alkane Aliphatic acyclic compound Alkane alkane water_solubility 61 mg / L at 20 °C Wikipedia logp 2.745 Wikipedia melting_point −140 to −134 °C Wikipedia boiling_point −1 to 1 °C Wikipedia logp 2.81 ALOGPS logs -1.91 ALOGPS logp 2.24 ChemAxon iupac butane ChemAxon average_mass 58.12 ChemAxon mono_mass 58.0783 ChemAxon smiles CCCC ChemAxon formula C4H10 ChemAxon inchi InChI=1S/C4H10/c1-3-4-2/h3-4H2,1-2H3 ChemAxon inchikey IJDNQMDRQITEOD-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 20.21 ChemAxon polarizability 8.28 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB03689 7843 37808 FDB000759 Butane 1.0 2020-03-19 00:44:46 UTC 2020-07-07 15:59:43 UTC CDB000579 Butyl formate Butyl formate, also known as butyl methanoate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carboxyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). A formate ester resulting from the formal condensation of formic acid with the hydroxy group of butan-1-ol. Butyl formate is a brandy, fruity, and plum tasting compound. Butyl formate has been detected, but not quantified, in blackcurrants and pineapples. Butyl formate has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Butyl methanoate FEMA 2916 FEMA no. 2196 Formic acid butyl ester Formic acid, butyl ester N-Butyl formate N-Butyl methanoate Butyl methanoic acid Formate butyl ester Formate, butyl ester N-Butyl formic acid N-Butyl methanoic acid Butyl formic acid Butylester kyseliny mravenci Hcoo(CH2)3ch3 C5H10O2 102.13 102.0681 butyl formate N-butylformate 592-84-7 CCCCOC=O InChI=1S/C5H10O2/c1-2-3-4-7-5-6/h5H,2-4H2,1H3 NMJJFJNHVMGPGM-UHFFFAOYSA-N belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Carboxylic acid esters Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound water_solubility 7.56 mg/mL at 27 °C melting_point -91.5 °C logp 1.53 ALOGPS logs -0.70 ALOGPS logp 1.2 ChemAxon pka_strongest_basic -6.8 ChemAxon iupac butyl formate ChemAxon average_mass 102.13 ChemAxon mono_mass 102.0681 ChemAxon smiles CCCCOC=O ChemAxon formula C5H10O2 ChemAxon inchi InChI=1S/C5H10O2/c1-2-3-4-7-5-6/h5H,2-4H2,1H3 ChemAxon inchikey NMJJFJNHVMGPGM-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 26.8 ChemAxon polarizability 11.33 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB020353 11125 11614 88514 CPD-18956 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:48 UTC 2020-08-04 22:28:22 UTC CDB000580 Carbofuran Carbofuran, also known as furadan belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Carbofuran is a potentially toxic compound and is, in fact, one of the most toxic carbamate pesticides. It is manufactured by the reaction of methyl isocyanate with 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran. In one study, the exposure of rats to sublethal amounts of carbofuran decreased testosterone by 88%, while the levels of progesterone, cortisol, and estradiol were significantly increased (1279%, 202%, and 150%, respectively) (PMID: 20021136). The use of carbofuran on human consumable crops is currently banned in the U.S.A, Canada and the European Union. Carbofuran is a structural mimic of the neurohormone melatonin and could directly bind to MT2 melatonin receptor (Ki = 1.7 uM) (PMID: 28027439). Disruption of melatonin signaling could impact the circadian rhythm balance and is linked to elevated risk of developing diabetes. Carbofuran has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamate 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamate Furadan 2,2-Dimethyl-2,3-dihydro-7-benzofuranyl N-methylcarbamic acid 2,3-Dihydro-2,2-dimethylbenzofuran-7-yl methylcarbamic acid 2, 3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate 2, 3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate 2,2-Dimethyl-2,2-dihydrobenzofuranyl-7 N-methylcarbamate 2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl methylcarbamate 2,2-Dimethyl-2,3-dihydrobenzoduranyl-7-N-methylcarbamate 2,2-Dimethyl-7-coumaranyl N-methylcarbamate 2,3-Dihydro-2,2-dimethyl-7-benzofuranol methylcarbamate 2,3-Dihydro-2,2-dimethyl-7-benzofuranol N-methylcarbamate 2,3-Dihydro-2,2-dimethyl-7-benzofuranol, methylcarbamATE 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate 2,3-Dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, 9ci 2,3-Dihydro-2,2-dimethylbenzofuranyl-7-N-methylcarbamate 7-Benzofurano, 2,3-dihydro-2,2-dimethyl, methylcarbamate 7-Benzofuranol, 2,3-dihydro-2,2-dimethyl-, methylcarbamate Bay 70143 Brifur Carbodan Carbofuran (pesticide/fertilizer mixture) Carbofuran mixture Carbofurane Chinufur Crisfuran Curaterr FMC 10242 Furacarb Furadan 3g Furadan 4F Furadan 75 WP Furadan g Furadane Furodan Karbofuranu Kenofuran NEX Niagaral 242 Pillarfuran Rampart Sipcam uk carbosip 5g Tripart nex Yaltox Bayer 70143 70143, Bayer C12H15NO3 221.25 221.1052 1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid furadan 4F 1563-66-2 CN=C(O)OC1=CC=CC2=C1OC(C)(C)C2 InChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14) DUEPRVBVGDRKAG-UHFFFAOYSA-N belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Coumarans Organic compounds Organoheterocyclic compounds Coumarans Aromatic heteropolycyclic compounds Alkyl aryl ethers Benzenoids Carboximidic acids and derivatives Hydrocarbon derivatives Imines Organopnictogen compounds Oxacyclic compounds Propargyl-type 1,3-dipolar organic compounds Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Carboximidic acid derivative Coumaran Ether Hydrocarbon derivative Imine Organic 1,3-dipolar compound Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Propargyl-type 1,3-dipolar organic compound 1-benzofurans Carbamate insecticides carbamate ester water_solubility 0.32 mg/mL at 25°C logp 2.32 melting_point 150 - 152°C logp 2.78 ALOGPS logs -3.12 ALOGPS logp 2.62 ChemAxon pka_strongest_acidic 3.78 ChemAxon pka_strongest_basic 2.16 ChemAxon iupac 1-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-N-methylmethanimidic acid ChemAxon average_mass 221.25 ChemAxon mono_mass 221.1052 ChemAxon smiles CN=C(O)OC1=CC=CC2=C1OC(C)(C)C2 ChemAxon formula C12H15NO3 ChemAxon inchi InChI=1S/C12H15NO3/c1-12(2)7-8-5-4-6-9(10(8)16-12)15-11(14)13-3/h4-6H,7H2,1-3H3,(H,13,14) ChemAxon inchikey DUEPRVBVGDRKAG-UHFFFAOYSA-N ChemAxon polar_surface_area 51.05 ChemAxon refractivity 60.12 ChemAxon polarizability 23.28 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008443 2468 2566 C14291 34611 Carbofuran Popovska-Gorevski M, Dubocovich ML, Rajnarayanan RV: Carbamate Insecticides Target Human Melatonin Receptors. Chem Res Toxicol. 2017 Feb 20;30(2):574-582. doi: 10.1021/acs.chemrestox.6b00301. Epub 2017 Jan 11. 28027439 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 Moulins JR, Blais M, Montsion K, Tully J, Mohan W, Gagnon M, McRitchie T, Kwong K, Snider N, Blais DR: Multiresidue Method of Analysis of Pesticides in Medical Cannabis. J AOAC Int. 2018 Nov 1;101(6):1948-1960. doi: 10.5740/jaoacint.17-0495. Epub 2018 May 29. 29843862 Goad RT, Goad JT, Atieh BH, Gupta RC: Carbofuran-induced endocrine disruption in adult male rats. Toxicol Mech Methods. 2004;14(4):233-9. doi: 10.1080/15376520490434476. 20021136 1.0 2020-03-19 00:44:52 UTC 2020-07-24 23:30:15 UTC CDB000581 Cedryl acetate Cedryl acetate belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cedryl acetate is the acetylated derivative of cedrol. Cedrol is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety, bearing a tertiary hydroxyl group. Cedryl acetate is a pale-yellow viscous liquid to solid and has a sharp dry woody odor. Cedrol has been reported to show antiseptic, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal activities (PMID 25343299). Additionally, cedrol seems to be a potent attractant for female mosquitos during oviposition, which could make cedrol useful in the design of bait traps (PMID: 25885703). Cedrol acetate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Cedryl acetic acid C17H28O2 264.41 264.2089 (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate 77-54-3 C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)OC(C)=O InChI=1S/C17H28O2/c1-11-6-7-13-15(3,4)14-10-17(11,13)9-8-16(14,5)19-12(2)18/h11,13-14H,6-10H2,1-5H3/t11-,13+,14-,16-,17+/m1/s1 HQKQRXZEXPXXIG-DTWJZALFSA-N belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. Cedrane and isocedrane sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cedrane sesquiterpenoid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 4.47 ALOGPS logs -5.61 ALOGPS logp 3.63 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undecan-8-yl acetate ChemAxon average_mass 264.41 ChemAxon mono_mass 264.2089 ChemAxon smiles C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC[C@@]3(C)OC(C)=O ChemAxon formula C17H28O2 ChemAxon inchi InChI=1S/C17H28O2/c1-11-6-7-13-15(3,4)14-10-17(11,13)9-8-16(14,5)19-12(2)18/h11,13-14H,6-10H2,1-5H3/t11-,13+,14-,16-,17+/m1/s1 ChemAxon inchikey HQKQRXZEXPXXIG-DTWJZALFSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 75.68 ChemAxon polarizability 31.26 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 13918856 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Jeong HU, Kwon SS, Kong TY, Kim JH, Lee HS: Inhibitory effects of cedrol, beta-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomes. J Toxicol Environ Health A. 2014;77(22-24):1522-32. doi: 10.1080/15287394.2014.955906. 25343299 Lindh JM, Okal MN, Herrera-Varela M, Borg-Karlson AK, Torto B, Lindsay SW, Fillinger U: Discovery of an oviposition attractant for gravid malaria vectors of the Anopheles gambiae species complex. Malar J. 2015 Mar 20;14:119. doi: 10.1186/s12936-015-0636-0. 25885703 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:54 UTC 2020-09-11 20:08:29 UTC CDB000582 cis-2-pinanol Cis-2-Pinanol is an organic compound and a derivative of pinane, on which a hydrogen atom has been replaced by a hydroxyl group on position C-2. Cis-2-Pinanol with the molecular formula C10H18O is biochemically a bicyclic monoterpenenoid. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cis-2-Pinanol is one of two isomers of 2-Pinanol. Cis-2-Pinanol is a colorless crystal with a camphor-like odor. It is produced industrially by the catalytic hydrogenation of 2-pinane hydroperoxide. Cis-2-Pinanol can also be obtained directly from pinane by air oxidation in the presence of alkalis, such as sodium hydroxide, at 80 ‚Äì 100 ¬∞C (https://doi.org/10.1002/14356007.a26_205). Cis-2-pinanol has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). C10H18O 154.25 154.1358 (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 4948-28-1 CC1(C)[C@@H]2C[C@H]1[C@@](C)(O)CC2 InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10-/m0/s1 YYWZKGZIIKPPJZ-XKSSXDPKSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Tertiary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Pinane monoterpenoid Tertiary alcohol logp 2.56 ALOGPS logs -2.27 ALOGPS logp 1.89 ChemAxon pka_strongest_acidic 19.91 ChemAxon pka_strongest_basic -0.65 ChemAxon iupac (1R,2S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@@H]2C[C@H]1[C@@](C)(O)CC2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10-/m0/s1 ChemAxon inchikey YYWZKGZIIKPPJZ-XKSSXDPKSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.55 ChemAxon polarizability 18.54 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6428289 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:44:59 UTC 2020-07-24 23:30:15 UTC CDB000583 Cis-Hex-3-en-1-ol Cis-Hex-3-en-1-ol or (Z)-3-Hexen-1-ol, also known as (3Z)-hex-3-en-1-ol or leaf alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, (Z)-3-hexen-1-ol is considered to be a fatty alcohol lipid molecule. (Z)-3-Hexen-1-ol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a colorless oily liquid with an intense grassy-green odor of freshly cut green grass and leaves. Cis-Hex-3-en-1-ol is produced in small amounts by most plants and it acts as an attractant to many predatory insects. Cis-3-hexen-1-ol has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Cis-3-Hexen-1-ol is a very important aroma compound that is used in fruit and vegetable flavors and in perfumes. 3-Hexen-1-ol cis-3-Hexen-1-ol 3-Hexen-1-ol, (Z)-isomer 3-Hexen-1-ol, (e)-isomer cis-3-Hexenol C6H12O 100.16 100.0888 hex-3-en-1-ol 3-hexenol 928-96-1 CCC=CCCO InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3 UFLHIIWVXFIJGU-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Fatty alcohols Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic acyclic compounds Hydrocarbon derivatives Primary alcohols Alcohol Aliphatic acyclic compound Fatty alcohol Hydrocarbon derivative Organic oxygen compound Organooxygen compound Primary alcohol an alcohol logp 1.69 ALOGPS logs -0.79 ALOGPS logp 1.33 ChemAxon pka_strongest_acidic 16.79 ChemAxon pka_strongest_basic -2 ChemAxon iupac hex-3-en-1-ol ChemAxon average_mass 100.16 ChemAxon mono_mass 100.0888 ChemAxon smiles CCC=CCCO ChemAxon formula C6H12O ChemAxon inchi InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3 ChemAxon inchikey UFLHIIWVXFIJGU-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 32.45 ChemAxon polarizability 12.46 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004107 10993 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:02 UTC 2020-07-07 15:59:46 UTC CDB000584 Citronellolformate Citronellol formate, or Citronellyl formate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Most fatty alcohols in nature are found as waxes which are esters with fatty acids and fatty alcohols. They are produced by bacteria, plants and animals for purposes of buoyancy, as source of metabolic water and energy, biosonar lenses (marine mammals) and for thermal insulation in the form of waxes (in plants and insects). Citronellol formate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citronellyl formate is used a flavouring ingredient. It has also been identified in plants such as citrus and in the essential oils of geranium, mandarin, satsuma, kumquat and other species. Citronellol formate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). C11H20O2 184.28 184.1463 (3R)-3,7-dimethyloct-6-en-1-yl formate (3R)-3,7-dimethyloct-6-en-1-yl formate C[C@@H](CCOC=O)CCC=C(C)C InChI=1S/C11H20O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,9,11H,4,6-8H2,1-3H3/t11-/m1/s1 DZNVIZQPWLDQHI-LLVKDONJSA-N belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Fatty alcohol esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohol esters Aliphatic acyclic compounds Acyclic monoterpenoids Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Acyclic monoterpenoid Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty alcohol ester Hydrocarbon derivative Monocarboxylic acid or derivatives Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound logp 3.86 ALOGPS logs -3.13 ALOGPS logp 3.14 ChemAxon pka_strongest_basic -6.8 ChemAxon iupac (3R)-3,7-dimethyloct-6-en-1-yl formate ChemAxon average_mass 184.28 ChemAxon mono_mass 184.1463 ChemAxon smiles C[C@@H](CCOC=O)CCC=C(C)C ChemAxon formula C11H20O2 ChemAxon inchi InChI=1S/C11H20O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,9,11H,4,6-8H2,1-3H3/t11-/m1/s1 ChemAxon inchikey DZNVIZQPWLDQHI-LLVKDONJSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 55.15 ChemAxon polarizability 22.31 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 38989047 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:07 UTC 2020-07-24 23:30:15 UTC CDB000585 Citronellyl acetate Citronellyl acetate, also known as Citronellol acetate or beta-citronellol acetate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl acetate is the acetate ester of citronellol. Citronellyl acetate exists as a clear, transparent liquid. It is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citronellyl acetate has a floral, rose, fruity, citrus aroma with a fruity, pear and apple-like taste. It is an approved food additive and can be used in apple, pear, banana and berry flavours. Citronellyl acetate is naturally produced by many plants and is found in carrot seeds, celery, citronella, black currants, ginger, grapefruit, lemons, mushrooms, orange, passion fruit, black pepper and wine. It is found in highest concentration in wild carrots, carrots, and lemons and in a lower concentration in mandarin orange (clementine, tangerine). Citronellyl acetate is one of several esters found in cannabis plants (PMID: 6991645). C12H22O2 198.31 198.162 (3S)-3,7-dimethyloct-6-en-1-yl acetate (3S)-3,7-dimethyloct-6-en-1-yl acetate 67601-05-2 C[C@H](CCOC(C)=O)CCC=C(C)C InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3/t11-/m0/s1 JOZKFWLRHCDGJA-NSHDSACASA-N belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Fatty alcohol esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohol esters Aliphatic acyclic compounds Acyclic monoterpenoids Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Acyclic monoterpenoid Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty alcohol ester Hydrocarbon derivative Monocarboxylic acid or derivatives Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound logp 4.13 ALOGPS logs -3.46 ALOGPS logp 3.19 ChemAxon pka_strongest_basic -7 ChemAxon iupac (3S)-3,7-dimethyloct-6-en-1-yl acetate ChemAxon average_mass 198.31 ChemAxon mono_mass 198.162 ChemAxon smiles C[C@H](CCOC(C)=O)CCC=C(C)C ChemAxon formula C12H22O2 ChemAxon inchi InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3/t11-/m0/s1 ChemAxon inchikey JOZKFWLRHCDGJA-NSHDSACASA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 59.64 ChemAxon polarizability 24.41 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6999975 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:45:10 UTC 2020-08-04 22:28:22 UTC CDB000586 Cumene Cumene or Isopropylbenzene, also known as 2-phenylpropane or cumol, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 ¬∞C. Cumene is produced commercially by Friedel‚ÄìCrafts alkylation of benzene with propylene. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals such as phenol and acetone. Isopropylbenzene is also found naturally in many plant foods, such as ceylon cinnamon, herbs and spices, cumin, and ginger. Cumene has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). (1-Methylethyl)benzene 2-Phenylpropane (1-Methylethyl)-benzene (1-Methylethyl)benzene (cumene) (Methylethyl)benzene (Propan-2-yl)benzene 1-Methylethyl-benzene 1-Methylethylbenzene, 9ci 2-Fenilpropano 2-Fenyl-propaan 2-Phenyl-propane Benzene, (1-methylethyl)-, oxidized, polyphenyl residues Benzene, (1-methylethyl)-, oxidized, sulfurized by-products Benzene, isopropyl Benzene,isopropyl cumol Cumeen Cumene CUMENE (cumene hydroperoxide (80-15-9)) Cumol I-propyl-benzene I-propylbenzene Iso-propylbenzene (cumene) Isopropilbenzene Isopropyl-benzene Isopropyl-benzol Isopropylbenzeen Isopropylbenzen Isopropylbenzol Oxidized cumene polyphenyl residues Phenol bottoms Polyphenyl residue Propane, 2-phenyl Sulfurized by-product OF cumene oxidation Isopropylbenzene C9H12 120.19 120.0939 (propan-2-yl)benzene cumene 98-82-8 CC(C)C1=CC=CC=C1 InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 RWGFKTVRMDUZSP-UHFFFAOYSA-N belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. Cumenes Organic compounds Benzenoids Benzene and substituted derivatives Cumenes Aromatic homomonocyclic compounds Aromatic hydrocarbons Phenylpropanes Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Cumene Hydrocarbon Phenylpropane Unsaturated hydrocarbon alkylbenzene an aromatic compound water_solubility 0.0613 mg/mL at 25 °C logp 3.66 melting_point -96.9 °C boiling_point 152 °C Wikipedia logp 3.67 ALOGPS logs -3.51 ALOGPS logp 3.22 ChemAxon iupac (propan-2-yl)benzene ChemAxon average_mass 120.19 ChemAxon mono_mass 120.0939 ChemAxon smiles CC(C)C1=CC=CC=C1 ChemAxon formula C9H12 ChemAxon inchi InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 ChemAxon inchikey RWGFKTVRMDUZSP-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 40.25 ChemAxon polarizability 14.82 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012268 7128 C14396 34656 7406 CPD0-2360 Cumene Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:14 UTC 2020-07-07 15:59:48 UTC CDB000587 Cuminaldehyde Cuminaldehyde belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cuminaldehyde, or 4-isopropylbenzaldehyde, is a natural organic compound with the molecular formula C10 H12O. It is a benzaldehyde with an isopropyl group in the 4-position. Cuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. Cuminaldehyde is a volatile compound representative of the cumin aroma. It has been detected to be present in trace amounts in the blood and milk of ewes fed with cumin seed (PMID: 8738023). In mammals, cuminaldehyde is metabolized by reduction but not by oxidation (PMID: 2815827). Cuminaldehyde is a constituent of the essential oils of eucalyptus, myrrh, cassia, and cumin, among others. It has a pleasant smell and contributes to the aroma of these oils. Cuminaldehyde has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Cuminaldehyde can also be synthesized by the reduction of 4-isopropylbenzoyl chloride or by the formylation of cumene. It is used commercially in perfumes and other cosmetics. 4-Isopropylbenzaldehyde Cumaldehyde Cumic aldehyde Cuminic aldehyde Cuminyl aldehyde p-Cumic aldehyde p-Isopropylbenzaldehyde p-Isopropylbenzenecarboxaldehyde 4-(1-Methylethyl)benzaldehyde 4-Isopropylbenzenecarboxylate Cuminal Cuminal p-(1-methylethyl)benzaldehyde p-Cuminic aldehyde p-Isopropyl benzaldehyde p-Isopropyl-benzaldehyde C10H12O 148.21 148.0888 4-(propan-2-yl)benzaldehyde cuminaldehyde 122-03-2 CC(C)C1=CC=C(C=O)C=C1 InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 WTWBUQJHJGUZCY-UHFFFAOYSA-N belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Aromatic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aromatic homomonocyclic compounds Benzaldehydes Benzoyl derivatives Cumenes Hydrocarbon derivatives Monocyclic monoterpenoids Organic oxides Phenylpropanes Aldehyde Aromatic homomonocyclic compound Aromatic monoterpenoid Aryl-aldehyde Benzaldehyde Benzenoid Benzoyl Cumene Hydrocarbon derivative Monocyclic benzene moiety Monocyclic monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound P-cymene Phenylpropane Cyclic monoterpenes a small molecule benzaldehydes boiling_point 235.5 °C logp 2.73 ALOGPS logs -3.01 ALOGPS logp 2.93 ChemAxon pka_strongest_basic -7.1 ChemAxon iupac 4-(propan-2-yl)benzaldehyde ChemAxon average_mass 148.21 ChemAxon mono_mass 148.0888 ChemAxon smiles CC(C)C1=CC=C(C=O)C=C1 ChemAxon formula C10H12O ChemAxon inchi InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3 ChemAxon inchikey WTWBUQJHJGUZCY-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 46.83 ChemAxon polarizability 17.06 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C06577 FDB008724 21106431 326 28671 C00003039 CPD-1003 Cuminaldehyde Desage M, Schaal B, Soubeyrand J, Orgeur P, Brazier JL: Gas chromatographic-mass spectrometric method to characterise the transfer of dietary odorous compounds into plasma and milk. J Chromatogr B Biomed Appl. 1996 Apr 12;678(2):205-10. doi: 10.1016/0378-4347(95)00527-7. 8738023 Ishida T, Toyota M, Asakawa Y: Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. Xenobiotica. 1989 Aug;19(8):843-55. doi: 10.3109/00498258909043145. 2815827 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:19 UTC 2020-06-29 20:41:12 UTC CDB000588 Decanal Decanal, also known as n-decyl aldehyde or caprinaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, decanal is considered to be a fatty aldehyde lipid molecule. Decanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Decanal is a sweet, aldehydic, and citrus tasting compound. Decanal is found, on average, in the highest concentration within a few different foods, such as corianders, dills, and gingers and in a lower concentration in limes, sweet oranges, and safflowers. Decanal has also been detected, but not quantified in, several different foods, such as fishes, cauliflowers, citrus, fats and oils, and lemon grass. This could make decanal a potential biomarker for the consumption of these foods. Decanal is a potentially toxic compound. Decanal, with regard to humans, has been found to be associated with several diseases such as uremia, asthma, and perillyl alcohol administration for cancer treatment; decanal has also been linked to the inborn metabolic disorder celiac disease. Decanal occurs naturally and is used in fragrances and flavoring. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Decanal is one of several aldehydes that are found in cannabis plants (PMID: 6991645). Decanal occurs naturally and is used in fragrances and flavoring. Decanal occurs in nature and is an important component in citrus along with octanal, citral, and sinensal. Decanal is also an important component of buckwheat odour. 1-Decanal 1-Decyl aldehyde Capraldehyde Caprinaldehyde Decanaldehyde N-Decaldehyde N-Decanal N-Decyl aldehyde 1-Decanal(mixed isomers) Aldehyde C10 C-10 Aldehyde Capric aldehyde Caprinic aldehyde Decaldehyde Decanal (acd/name 4.0) Decyl aldehyde Decylic aldehyde N-Decanal (capric aldehyde) Decanal C10H20O 156.27 156.1514 decanal decanal 112-31-2 CCCCCCCCCC=O InChI=1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h10H,2-9H2,1H3 KSMVZQYAVGTKIV-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Medium-chain aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-hydrogen aldehydes Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Alpha-hydrogen aldehyde Hydrocarbon derivative Medium-chain aldehyde Organic oxide Fatty aldehydes Fatty aldehydes a fatty aldehyde fatty aldehyde melting_point -5 °C boiling_point 207 to 209 °C Wikipedia logp 4.44 ALOGPS logs -4.31 ALOGPS logp 3.43 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac decanal ChemAxon average_mass 156.27 ChemAxon mono_mass 156.1514 ChemAxon smiles CCCCCCCCCC=O ChemAxon formula C10H20O ChemAxon inchi InChI=1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h10H,2-9H2,1H3 ChemAxon inchikey KSMVZQYAVGTKIV-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 48.55 ChemAxon polarizability 20.66 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012768 7883 8175 C12307 31457 C00030804 CPD-8490 Decanal Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 1.0 2020-03-19 00:45:22 UTC 2020-09-11 20:08:26 UTC CDB000589 Delta-3-carene Delta-3-Carene or 3-Carene is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine with a content as high as 42% depending on the source. Carene has a sweet and pungent odor. best described as fir needles, musky earth, and damp woodlands combination. Delta-3-Carene is one of the monoterpenes that are known in the cannabis plant. (PMID: 6991645) (-)-alpha-Carene (-)-Delta(3)-Carene (-)-3-Carene Car-3-ene (-)-a-Carene (-)-Α-carene (-)-Δ(3)-carene (+)-a-Carene (+)-Α-carene (+)-3-Carene (+)-Car-3-ene (+)-Carene (+)-delta(3)-Carene (+)-Delta3-Carene (1S)-(+)-3-Carene (1S)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene (1S,6R)-(+)-3-Carene (1S,6R)-3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene (S)-(+)-3-Carene Isodiprene 3-Carene 3-Carene, (S)-(cis)-isomer 3-Carene, (R)-isomer delta-3-Carene delta(3)-Carene delta3-Carene C10H16 136.23 136.1252 (1R,6S)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene (-)-delta(3)-carene 20296-50-8 CC1=CC[C@H]2[C@@H](C1)C2(C)C InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m0/s1 BQOFWKZOCNGFEC-DTWKUNHWSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Carane monoterpenoid Cyclic olefin Hydrocarbon Olefin Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Bicyclic monoterpenoids Bicyclic monoterpenoids Cyclic monoterpenes car-3-ene logp 3.64 ALOGPS logs -2.96 ALOGPS logp 2.8 ChemAxon iupac (1R,6S)-3,7,7-trimethylbicyclo[4.1.0]hept-3-ene ChemAxon average_mass 136.23 ChemAxon mono_mass 136.1252 ChemAxon smiles CC1=CC[C@H]2[C@@H](C1)C2(C)C ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9+/m0/s1 ChemAxon inchikey BQOFWKZOCNGFEC-DTWKUNHWSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 44.72 ChemAxon polarizability 17.33 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013714 443156 391428 C00011045 C09839 3381 1.0 2020-03-19 00:45:26 UTC 2020-06-29 20:41:12 UTC CDB000590 Diacetone alcohol Diacetone alcohol, sometimes referred to as DAA, belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Diacetone alcohol is an organic compound with the chemical formula CH3C(O)CH2C(OH)(CH3)2. Diacetone alcohol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It is a colorless liquid, used as a solvent and a common synthetic intermediate used for the preparation of other compounds. Diacetone alcohol is found in the highest concentration in cow milk but it has also been detected, not quantified, in several different foods, such as fruits, mung beans, papaya, and soybeans Diacetone alcohol has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Diacetone alcohol is commercially used in cellulose ester lacquers, particularly of the brushing type, where it produces brilliant gloss and a hard film and where its lack of odor is desirable. It is used in lacquer thinners, dopes, wood stains, wood preservatives and printing pastes, in coating compositions for paper and textiles, permanent markers, in making artificial silk and leather, in imitation gold leaf, in celluloid cements, as a preservative for animal tissue, in metal cleaning compounds, in the manufacture of photographic film, and in hydraulic brake fluids, where it is usually mixed with an equal volume of castor oil. 2-Methyl-2-pentanol-4-one 4-Hydroxy-2-keto-4-methylpentane 4-Hydroxy-4-methyl-2-pentanone 4-Hydroxy-4-methylpentan-2-one Acetonyldimethylcarbinol Diacetonalkohol Diacetone-alcool Diacetonyl alcohol Dimethyl acetonyl carbinol (CH3)2C(OH)CH2C(O)CH3 2-Hydroxy-2-methyl-4-pentanone 2-Methyl-3-pentanol-4-one 4-Hydroxy-4-methyl pentan-2-one 4-Hydroxy-4-methyl-pentan-2-ON 4-Hydroxy-4-methylpentanone 4-Hydroxy-4-methylpentanone-2 4-Idrossi-4-metil-pentan-2-one 4-Methyl-2-pentanon-4-ol 4-Methyl-4-hydroxy-2-pentanone Diacetonalcohol Diacetonalcool Diacetone Diacetonealcool Diketone alcohol Hydroxy-4-methyl-2-pentanone Pyranton Pyranton a Pyraton Tyranton Diacetone alcohol C6H12O2 116.16 116.0837 4-hydroxy-4-methylpentan-2-one diacetone alcohol 123-42-2 CC(=O)CC(C)(C)O InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3 SWXVUIWOUIDPGS-UHFFFAOYSA-N belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group. Beta-hydroxy ketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Tertiary alcohols Alcohol Aliphatic acyclic compound Beta-hydroxy ketone Hydrocarbon derivative Organic oxide Tertiary alcohol Oxygenated hydrocarbons beta-hydroxy ketone water_solubility 1000 mg/mL at 25 °C melting_point -44 °C boiling_point 166 °C Wikipedia logp 0.04 ALOGPS logs 0.10 ALOGPS logp 0.22 ChemAxon pka_strongest_acidic 15.21 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 4-hydroxy-4-methylpentan-2-one ChemAxon average_mass 116.16 ChemAxon mono_mass 116.0837 ChemAxon smiles CC(=O)CC(C)(C)O ChemAxon formula C6H12O2 ChemAxon inchi InChI=1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3 ChemAxon inchikey SWXVUIWOUIDPGS-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 31.65 ChemAxon polarizability 12.76 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008104 13838151 31256 55381 Diacetone_alcohol Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:29 UTC 2020-07-07 15:59:51 UTC CDB000591 Dibutyl phthalate Dibutyl phthalate, also known as DBP or butyl phthalic acid, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is a paint tasting, colorless oil, although commercial samples are often yellow. Metabolism of dibutyl phthalate proceeds mainly by nonspecific esterases in the gastrointestinal tract, which hydrolyze one of the butyl ester bonds to yield mono-n-butyl phthalate, the primary toxic metabolite. Dibutyl phthalate is absorbed via oral, inhalation, and dermal routes. It is rapidly distributed and cleared from the body. Mono-butyl phthalate is conjugated with glucuronic acid via glucuronosyltransferase and excreted in the urine. Dibutyl phthalate is a potentially toxic compound. The most characteristic effect of dibutyl phthalate on mammals is testicular atrophy. Animal studies have shown that dibutyl phthalate can affect the reproductive ability by decreasing sperm count and causing birth defects. DBT has also exhibited toxic effects in liver mitochondria by uncoupling energy-linked processes and inhibiting the succinate dehydrogenase. Adverse effects from dibutyl phthalate exposure have not yet been reported in humans. Dibutyl phthalate is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. DBP is also used as an ectoparasiticide. Dibutyl phthalate, and other phthalates, are often reported as components of natural products extracts. However, due to their high solubility in organic solvents (e.g. ethanol, ethers, dichloromethane, and benzene) they are most likely a contaminant analyte, introduced into the sample through the use of plastics during sample preparation or from contaminated solvents, especially in gas chromatography analyses. Dibuthyl phtalate has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 1,2-Benzenedicarboxylic acid dibutyl ester Benzene-O-dicarboxylic acid di-N-butyl ester Benzenedicarboxylic acid dibutyl ester Butyl phthalate DBP Di-N-butyl phthalate Dibutyl 1,2-benzenedicarboxylate Dibutyl O-phthalate Dibutyl-O-phthalate N-Butyl phthalate O-Benzenedicarboxylic acid dibutyl ester Phthalic acid di-N-butyl ester Phthalic acid dibutyl ester 1,2-Benzenedicarboxylate dibutyl ester Benzene-O-dicarboxylate di-N-butyl ester Benzenedicarboxylate dibutyl ester Butyl phthalic acid Di-N-butyl phthalic acid Dibutyl 1,2-benzenedicarboxylic acid Dibutyl O-phthalic acid Dibutyl-O-phthalic acid N-Butyl phthalic acid O-Benzenedicarboxylate dibutyl ester Phthalate di-N-butyl ester Phthalate dibutyl ester Dibutyl phthalic acid 1,2-Benzenedicarboxylic acid, 1,2-dibutyl ester 1,2-Benzenedicarboxylic acid, dibutyl ester Araldite 502 Benzene-O-dicarboxylic acid, di-N-butyl ester Benzenedicarboxylic acid, dibutyl ester BUFA Celluflex DPB DBP (Ester) Di N butyl phthalate Di-N-butyl phthalate (dbup) Di-N-butylester kyseliny ftalove Di-N-butylorthophthalate Dibutyl 1, 2-benzenedicarboxylate Dibutyl ester OF 1,2-benzenedicarboxylic acid Dibutyl phthalated Dibutyl-1,2-benzenedicarboxylate Dibutyl-phthalate Dibutyll phthalate Dibutylphthatlate Elaol Ergoplast FDB Ersoplast fda Genoplast b Hatcol DBP Hexaplas m/b Kodaflex DBP Morflex 240 N-Butylphthalate O-Benzenedicarboxylic acid, dibutyl ester Ortho-dibutyl phthalate Phthalate, butyl Phthalate, di-N-butyl Phthalate, dibutyl Phthalic acid, dibutyl ester Polycizer DBP Rapidcelltrade markp RC Plasticizer DBP Staflex DBP Uniflex DBP Unimoll DB Uniplex 150 Witcizer 300 Dibutylphthalic acid C16H22O4 278.34 278.1518 1,2-dibutyl benzene-1,2-dicarboxylate dibutyl-phthalate 84-74-2 CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 DOIRQSBPFJWKBE-UHFFFAOYSA-N belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoic acid esters Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds Benzoyl derivatives Carboxylic acid esters Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organooxygen compounds Aromatic homomonocyclic compound Benzoate ester Benzoyl Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Insect repellents Phthalates diester phthalate ester water_solubility 0.0112 mg/mL at 25 °C logp 4.50 melting_point 35 °C boiling_point 340 °C Wikipedia logp 4.53 ALOGPS logs -4.67 ALOGPS logp 4.63 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac 1,2-dibutyl benzene-1,2-dicarboxylate ChemAxon average_mass 278.34 ChemAxon mono_mass 278.1518 ChemAxon smiles CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC ChemAxon formula C16H22O4 ChemAxon inchi InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 ChemAxon inchikey DOIRQSBPFJWKBE-UHFFFAOYSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 77.86 ChemAxon polarizability 32.15 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB011261 13837319 3026 DB13716 C14214 Dibutyl_phthalate 34687 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:33 UTC 2020-07-07 15:59:52 UTC CDB000592 Diethyl Phthalate Diethyl phthalate, also known as 1,2-diethyl phthalate or DEP, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Diethyl phthalate is hydrolyzed to its monoester derivative by diethyl phthalic acid hydrolase. Diethyl phthalate is a potentially toxic compound. It is a clear liquid at room temperature, and it is only slightly denser than liquid water. When burned, DEP produces toxic gases. Many organic molecules are soluble in it and it is therefore often used to bind cosmetics and fragrances. It is industrially used as a plasticizer, detergent bases and aerosol sprays. Diethyl phthalate is produced by the reaction of phthalic anhydride with ethanol in the presence of a catalytic amount of concentrated sulfuric acid. Diethyl phthalate, and other phthalates, are often reported as components of natural products extracts. However, due to their high solubility in organic solvents (e.g. ethanol, ethers, dichloromethane, and benzene) they are most likely a contaminant analyte, introduced into the sample through the use of plastics during sample preparation or from contaminated solvents, especially in gas chromatography analyses. Diethyl phtalate has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 1,2-Benzenedicarboxylic acid diethyl ester 1,2-Diethyl phthalate DEP Diethyl 1,2-benzenedicarboxylate Diethyl benzene-1,2-dicarboxylate Diethyl O-phthalate Ethyl phthalate O-Benzenedicarboxylic acid diethyl ester O-Bis(ethoxycarbonyl)benzene Phthalic acid diethyl ester Phthalsaeurediaethylester 1,2-Benzenedicarboxylate diethyl ester 1,2-Diethyl phthalic acid Diethyl 1,2-benzenedicarboxylic acid Diethyl benzene-1,2-dicarboxylic acid Diethyl O-phthalic acid Ethyl phthalic acid O-Benzenedicarboxylate diethyl ester Phthalate diethyl ester Diethyl phthalate Diethyl phthalic acid C12H14O4 222.24 222.0892 1,2-diethyl benzene-1,2-dicarboxylate diethyl phthalate CCOC(=O)C1=CC=CC=C1C(=O)OCC InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3 FLKPEMZONWLCSK-UHFFFAOYSA-N belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoic acid esters Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds Benzoyl derivatives Carboxylic acid esters Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organooxygen compounds Aromatic homomonocyclic compound Benzoate ester Benzoyl Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Phthalates diester ethyl ester phthalate ester logp 2.60 ALOGPS logs -2.76 ALOGPS logp 2.69 ChemAxon pka_strongest_basic -6.7 ChemAxon iupac 1,2-diethyl benzene-1,2-dicarboxylate ChemAxon average_mass 222.24 ChemAxon mono_mass 222.0892 ChemAxon smiles CCOC(=O)C1=CC=CC=C1C(=O)OCC ChemAxon formula C12H14O4 ChemAxon inchi InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3 ChemAxon inchikey FLKPEMZONWLCSK-UHFFFAOYSA-N ChemAxon polar_surface_area 52.6 ChemAxon refractivity 59.61 ChemAxon polarizability 23.16 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6781 C14175 34698 C00042472 Diethyl_phthalate Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:36 UTC 2020-07-07 15:59:52 UTC CDB000593 Dimethylbenzylcarbinyl acetate Dimethylbenzylcarbinyl acetate belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Dimethylbenzylcarbinyl acetate appears as a white to pale yellow crystalline solid. It is a sweet, berry, and floral tasting compound and it is used as a flavouring agent. It also has a floral, jasmine and rose-like odour and it is used in perfumery. Dimethylbenzylcarbinyl acetate has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 2-Methyl-1-phenyl-2-propanyl acetic acid 1,1-Dimethyl-2-phenylethyl acetate 2-Benzyl-2-propyl acetate alpha, alpha-Dimethylphenethyl alcohol, acetate alpha,alpha-Dimethylbenzeneethyl acetate alpha,alpha-Dimethylphenethyl acetate alpha,alpha-Dimethylphenethyl alcohol, acetate Benzeneethanol, alpha,alpha-dimethyl-, 1-acetate Benzeneethanol, alpha,alpha-dimethyl-, acetate Benzyl dimethyl carbinyl acetate Benzyldimethyl carbinyl acetate Benzyldimethylcarbinol acetate Benzyldimethylcarbinyl acetate Benzylpropyl acetate Dimethyl benzyl carbinyl acetate Dimethylbenzyl carbinol acetate Dimethylbenzylcarbinol acetate Dimethylbenzylcarbinyl acetate Dmbca FEMA 2392 Phenethyl alcohol, alpha,alpha-dimethyl-, acetate 2-Methyl-1-phenylpropan-2-yl acetic acid C12H16O2 192.25 192.115 2-methyl-1-phenylpropan-2-yl acetate 2-methyl-1-phenylpropan-2-yl acetate 151-05-3 CC(=O)OC(C)(C)CC1=CC=CC=C1 InChI=1S/C12H16O2/c1-10(13)14-12(2,3)9-11-7-5-4-6-8-11/h4-8H,9H2,1-3H3 FLUWAIIVLCVEKF-UHFFFAOYSA-N belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenylpropanes Organic compounds Benzenoids Benzene and substituted derivatives Phenylpropanes Aromatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aromatic homomonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Phenylpropane melting_point 30 °C logp 3.40 ALOGPS logs -3.72 ALOGPS logp 2.63 ChemAxon pka_strongest_basic -7 ChemAxon iupac 2-methyl-1-phenylpropan-2-yl acetate ChemAxon average_mass 192.25 ChemAxon mono_mass 192.115 ChemAxon smiles CC(=O)OC(C)(C)CC1=CC=CC=C1 ChemAxon formula C12H16O2 ChemAxon inchi InChI=1S/C12H16O2/c1-10(13)14-12(2,3)9-11-7-5-4-6-8-11/h4-8H,9H2,1-3H3 ChemAxon inchikey FLUWAIIVLCVEKF-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 55.84 ChemAxon polarizability 21.63 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008188 8673 9024 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:39 UTC 2020-07-10 00:17:45 UTC CDB000594 Dimethylpyrazine Dimethylpyrazine or 2,3-Dimethylpyrazine, also known as 2,3-DMP, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that contains two nitrogen atoms, at positions 1 and 4, and four carbon atoms. Dimethylpyrazine is a moderately basic compound (based on its pKa). It is an almond, butter, and caramel tasting compound and it has been detected, but not quantified, in several different foods, such as soybeans, nuts, green vegetables, cereals and cereal products, and tortilla chips. Dimethylpyrazine is a component of the aroma of roasted sesame seeds. Alkylpyrazines are also formed during the cooking of some foods via the Maillard reaction. Dimethylpyrazine has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 2,3-Dimethylpyrazine is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 23-Dimethyl-pyrazine 2,3-Dimethyl-1,4-diazine 2,3-Dimethyl-pyrazine FEMA 3271 2,3-DMP Pyrazine C6H8N2 108.14 108.0687 2,3-dimethylpyrazine pyrazine, 2,3-dimethyl- 5910-89-4 CC1=NC=CN=C1C InChI=1S/C6H8N2/c1-5-6(2)8-4-3-7-5/h3-4H,1-2H3 OXQOBQJCDNLAPO-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Pyrazines Organic compounds Organoheterocyclic compounds Diazines Pyrazines Aromatic heteromonocyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyrazine logp 0.54 logp 0.63 ALOGPS logs 0.22 ALOGPS logp -0.2 ChemAxon pka_strongest_basic 1.62 ChemAxon iupac 2,3-dimethylpyrazine ChemAxon average_mass 108.14 ChemAxon mono_mass 108.0687 ChemAxon smiles CC1=NC=CN=C1C ChemAxon formula C6H8N2 ChemAxon inchi InChI=1S/C6H8N2/c1-5-6(2)8-4-3-7-5/h3-4H,1-2H3 ChemAxon inchikey OXQOBQJCDNLAPO-UHFFFAOYSA-N ChemAxon polar_surface_area 25.78 ChemAxon refractivity 30.93 ChemAxon polarizability 11.75 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB010958 20843 22201 Alkylpyrazine Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:42 UTC 2020-08-04 22:28:23 UTC CDB000595 Dimethylsulfide Dimethylsulfide, also known as methyl thioether or 2-thiapropane, belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups. Dimethylsulfide is a sulfur containing organic chemical compound with a disagreeable odor. It is produced in its vapor form while cooking certain vegetables, notably corn, cabbage, and seafood. It is also an indication of bacterial infection in malt production and brewing. Dimethylsulfide is a breakdown product of dimethylsulfoniopropionate and is also produced by the bacterial metabolism of methanethiol. Dimethylsulfide flammable liquid with a boiling point of 37 ¬∞C. It can also be found as a microbial metabolite from bacteria from the genera Bradyrhizobium, Cyanothece, Escherichia, Pseudomonas and Rhizobiaceae (PMID: 25807229). Dimethylsulfide is the most abundant biological sulfur compound emitted to the atmosphere. Emission occurs over the oceans by phytoplankton. Dimethyl sulfide, dimethyl disulfide, and dimethyl trisulfide have been found among the volatiles given off by the fly-attracting plant known as dead-horse arum (Helicodiceros muscivorus). Dimethyl sulfide has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). (METHYLsulfanyl)methane 2-Thiapropane [SMe2] Dimethyl sulphide DMS Methyl sulfide Methyl thioether (METHYLsulphanyl)methane Dimethyl sulfide Methyl sulphide Dimethylsulphide Dimethyl sulfoxide(reduced) Methylthiomethane 2-Thiopropane Dimethyl monosulfide Dimethyl sulfide (natural) Dimethyl thioether Dimethylsulfid Methanethiomethane Methyl monosulfide Methylthiomethyl radical MSM Reduced-dmso Thiobis-methane Thiopropane C2H6S 62.13 62.019 (methylsulfanyl)methane dimethyl sulfide 75-18-3 CSC InChI=1S/C2H6S/c1-3-2/h1-2H3 QMMFVYPAHWMCMS-UHFFFAOYSA-N belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups. Dialkylthioethers Organic compounds Organosulfur compounds Thioethers Dialkylthioethers Aliphatic acyclic compounds Hydrocarbon derivatives Sulfenyl compounds Aliphatic acyclic compound Dialkylthioether Hydrocarbon derivative Sulfenyl compound aliphatic sulfide an organosulfur compound water_solubility 22 mg/mL at 25 °C logp 0.977 Wikipedia melting_point -98.3 °C boiling_point 35 to 41 °C Wikipedia logp 0.59 ALOGPS logs -0.53 ALOGPS logp 1.22 ChemAxon iupac (methylsulfanyl)methane ChemAxon average_mass 62.13 ChemAxon mono_mass 62.019 ChemAxon smiles CSC ChemAxon formula C2H6S ChemAxon inchi InChI=1S/C2H6S/c1-3-2/h1-2H3 ChemAxon inchikey QMMFVYPAHWMCMS-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 18.89 ChemAxon polarizability 7.24 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003591 C00580 1068 1039 17437 CPD-7670 Dimethyl_sulfide 6603 Carrion O, Curson ARJ, Kumaresan D, Fu Y, Lang AS, Mercade E, Todd JD: A novel pathway producing dimethylsulphide in bacteria is widespread in soil environments. Nat Commun. 2015 Mar 25;6:6579. doi: 10.1038/ncomms7579. 25807229 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:45 UTC 2020-06-29 20:41:13 UTC CDB000596 Dimethylsulfone Dimethyl sulfone (DMSO2), also known as sulfonylbismethane, belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group, with the general structure RS(=O)2R' (R,R' =alkyl, aryl). It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages and it is marketed as a dietary supplement. This colorless solid features a sulfonyl functional group and is considered relatively inert chemically. Dimethyl sulfone reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. Dimethyl sulfone is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a metabolite occurring in plasma and cerebrospinal fluid of normal humans. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism (PMID: 15996001). It is sometimes used as a cutting agent for illicitly manufactured methamphetamine. Because of its polarity and thermal stability, Dimethyl sulfone is used industrially as a high-temperature solvent for both inorganic and organic substances. Dimethyl sulfone is also commonly found in the atmosphere above marine areas, where it is used as a carbon source by the airborne bacteria Afipia (PMID: 23359712). It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Dimethyl sulphone Methylsulfonylmethane Sulfonylbismethane Sulphonylbismethane Methylsulphonylmethane (Methylsulfonyl)methane Dimethylsulfone Lignisul MSM Methyl sulfone Opti MSM Sulfonylbis-methane Methyl sulfonmethane Dimethyl sulfone, 13C-labeled Sulphonyldimethane Dimethyl sulfone C2H6O2S 94.13 94.0089 methanesulfonylmethane methylsulfonylmethane 67-71-0 CS(C)(=O)=O InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3 HHVIBTZHLRERCL-UHFFFAOYSA-N belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms. Sulfones Organic compounds Organosulfur compounds Sulfonyls Sulfones Aliphatic acyclic compounds Hydrocarbon derivatives Organic oxides Aliphatic acyclic compound Hydrocarbon derivative Organic oxide Organic oxygen compound Sulfone a sulfone sulfone logp -1.41 HANSCH,C ET AL. (1995) melting_point 109 °C boiling_point 248 °C Wikipedia logp -0.95 ALOGPS logs -0.23 ALOGPS logp -1.3 ChemAxon iupac methanesulfonylmethane ChemAxon average_mass 94.13 ChemAxon mono_mass 94.0089 ChemAxon smiles CS(C)(=O)=O ChemAxon formula C2H6O2S ChemAxon inchi InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3 ChemAxon inchikey HHVIBTZHLRERCL-UHFFFAOYSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 20.53 ChemAxon polarizability 8.6 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5978 FDB006725 6213 9349 C11142 Methylsulfonylmethane 7236 Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6. doi: 10.1002/nbm.966. 15996001 DeLeon-Rodriguez N, Lathem TL, Rodriguez-R LM, Barazesh JM, Anderson BE, Beyersdorf AJ, Ziemba LD, Bergin M, Nenes A, Konstantinidis KT: Microbiome of the upper troposphere: species composition and prevalence, effects of tropical storms, and atmospheric implications. Proc Natl Acad Sci U S A. 2013 Feb 12;110(7):2575-80. doi: 10.1073/pnas.1212089110. Epub 2013 Jan 28. 23359712 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:51 UTC 2020-08-04 22:28:23 UTC CDB000598 Durene Durene also known as 1,2,4,5-tetramethylbenzene, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 ¬∞C), reflecting its high molecular symmetry. It is a component of coal tar and was first prepared from pseudocumene in 1870. It is produced by methylation of other methylated benzene compounds such as p-xylene and pseudocumene (DOI: 10.15227/orgsyn.010.0032). Durene is a colourless solid with a sweet odor. It is also a sweet and rancid tasting compound. Durene has been detected, but not quantified, in sweet cherries. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 2,5-Dimethyl-p-xylene Durol Durene C10H14 134.22 134.1096 1,2,4,5-tetramethylbenzene durene 95-93-2 CC1=CC(C)=C(C)C=C1C InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 SQNZJJAZBFDUTD-UHFFFAOYSA-N belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene and substituted derivatives Organic compounds Benzenoids Benzene and substituted derivatives Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Monocyclic benzene moiety Unsaturated hydrocarbon tetramethylbenzene melting_point 79.2 °C Wikipedia boiling_point 192 °C at 760mmHg Wikipedia logp 4.05 ALOGPS logs -3.65 ALOGPS logp 4.03 ChemAxon iupac 1,2,4,5-tetramethylbenzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CC1=CC(C)=C(C)C=C1C ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 ChemAxon inchikey SQNZJJAZBFDUTD-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.22 ChemAxon polarizability 17.15 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 7269 FDB029672 C14534 38978 Durene Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:54 UTC 2020-07-07 15:59:56 UTC CDB000599 Dyclocaine Dyclocaine or Dyclonine, also known as diclonina or dycloninum, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by an alkyl and a phenyl group. Dyclocaine is a potentially toxic compound. It is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray. Dyclonine is only found in individuals that have used or taken this drug. Dyclonine blocks both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). 1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanone 2-(1-Piperidyl)ethyl p-butoxyphenyl ketone 3-Piperidino-4'-butoxypropiophenone 4'-Butoxy-3-piperidinopropiophenone 4-Butoxy-beta-piperidinopropiophenone 4-N-Butoxy-beta-(1-piperidyl)propiophenone Diclonina Dycloninum 4-Butoxy-b-piperidinopropiophenone 4-Butoxy-β-piperidinopropiophenone 4-N-Butoxy-b-(1-piperidyl)propiophenone 4-N-Butoxy-β-(1-piperidyl)propiophenone Sucrets Tanac Dyclone Dyclonine hydrochloride Dyclonine HCL C18H27NO2 289.41 289.2042 1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one dyclonine 586-60-7 CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1 InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3 BZEWSEKUUPWQDQ-UHFFFAOYSA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic heteromonocyclic compounds Alkyl aryl ethers Aryl alkyl ketones Azacyclic compounds Benzoyl derivatives Beta-amino ketones Hydrocarbon derivatives Organic oxides Organopnictogen compounds Phenol ethers Phenoxy compounds Piperidines Trialkylamines Alkyl aryl ether Alkyl-phenylketone Amine Aromatic heteromonocyclic compound Aryl alkyl ketone Azacycle Benzenoid Benzoyl Beta-aminoketone Ether Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Phenol ether Phenoxy compound Piperidine Tertiary aliphatic amine Tertiary amine aromatic ketone piperidines water_solubility 4.60e-02 g/L logp 3.7 logp 4.11 ALOGPS logs -3.80 ALOGPS logp 3.68 ChemAxon pka_strongest_acidic 15.88 ChemAxon pka_strongest_basic 8.36 ChemAxon iupac 1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one ChemAxon average_mass 289.41 ChemAxon mono_mass 289.2042 ChemAxon smiles CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1 ChemAxon formula C18H27NO2 ChemAxon inchi InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3 ChemAxon inchikey BZEWSEKUUPWQDQ-UHFFFAOYSA-N ChemAxon polar_surface_area 29.54 ChemAxon refractivity 87.07 ChemAxon polarizability 35.14 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB00645 3180 3068 4724 C07881 Dyclonine Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:45:56 UTC 2020-06-29 20:41:13 UTC CDB000600 Estragole Estragole or 1-Methoxy-4-(2-propenyl) benzene, also known as methylchavicol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Its chemical structure consists of a benzene ring substituted with a methoxy group and an allyl group. It is a colorless liquid, although impure samples can appear yellow. Estragole is a sweet, alcohol, and anise tasting compound. It is used in the preparation of fragrances. Estragole has also been found as a component of various trees and plants, including turpentine (pine oil), anise, fennel, bay, tarragon, and basil. It has also been found in lower concentrations in star anises, hyssops, and tarragons. Estragole has also been detected, but not quantified, in several different foods, such as ceylon cinnamons, dills, sweet bay, gingers, and pepper (spice). Estragole has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Methylchavicol 1-Allyl-4-methoxybenzene 1-Methoxy-4-(2-propen-1-yl)-benzene 1-Methoxy-4-(2-propen-1-yl)benzene 1-Methoxy-4-(2-propenyl)-benzene 1-Methoxy-4-(2-propenyl)benzene, 9ci 1-Methoxy-4-prop-2-enylbenzene 3-(p-Methoxyphenyl)propene 4-Allyl-1-methoxybenzene 4-Allylanisole 4-Allylmethoxybenzene 4-Methoxyallylbenzene Benzene, 1-methoxy, 4-prop-2-enyl BENZENE,1-allyl,4-methoxy methylchavicol Chavicol methyl ether Chavicyl methyl ether Esdragol Esdragole Esdragon Estragol Estragol (methylchavicol) Estragole Ether, p-allylphenyl methyl FEMA 2411 Isoanethole Isoanthethole Methyl chavicol Methyl chavicole Methyl chavicole (estragole) Methyl-chavicol O-Methyl-chavicol p-Allyl-anisole p-Allylanisole p-Allylmethoxybenzene p-Allylphenyl methyl ether p-Methoxyallylbenzene Para-allylanisole (estragole) Tarragon Terragon 1-Methoxy-4-(2-propenyl)benzene 3-(4-Methoxyphenyl)-1-propene 3-(4-Methoxyphenyl)propene 3-(p-Methoxyphenyl)-1-propene Esteragol Estragenole O-Methylchavicol C10H12O 148.2 148.0888 1-methoxy-4-(prop-2-en-1-yl)benzene tarragon 140-67-0 COC1=CC=C(CC=C)C=C1 InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 ZFMSMUAANRJZFM-UHFFFAOYSA-N belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anisoles Organic compounds Benzenoids Phenol ethers Anisoles Aromatic homomonocyclic compounds Alkyl aryl ethers Hydrocarbon derivatives Methoxybenzenes Phenoxy compounds Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenoxy compound Monolignols an aromatic compound olefinic compound water_solubility 0.178 mg/mL at 25 °C boiling_point 216 °C Wikipedia logp 3.23 ALOGPS logs -3.30 ALOGPS logp 2.91 ChemAxon pka_strongest_basic -4.8 ChemAxon iupac 1-methoxy-4-(prop-2-en-1-yl)benzene ChemAxon average_mass 148.2 ChemAxon mono_mass 148.0888 ChemAxon smiles COC1=CC=C(CC=C)C=C1 ChemAxon formula C10H12O ChemAxon inchi InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3 ChemAxon inchikey ZFMSMUAANRJZFM-UHFFFAOYSA-N ChemAxon polar_surface_area 9.23 ChemAxon refractivity 46.81 ChemAxon polarizability 16.95 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012392 13850247 649 8815 C00002740 C10452 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:05 UTC 2020-07-24 23:30:08 UTC CDB000602 Ethylene oxide Ethylene Oxide, also known as 1,2-epoxyethane or aethylenoxid, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three atom rings (one oxygen and two carbon atoms). Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. It is industrially produced by oxidation of ethylene in the presence of a silver catalyst. Ethylene oxide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Ethylene oxide is used for making a wide range of products. It is also used for the sterilization surgical equipment or supplies that require sterile conditions but are heat sensitive or unable to be placed inside an autoclave. Ehtylene oxide is also considered a plant growth regulator and signalling molecule, being directly linked to the maturation and senescence of some plant organs and fruits. Ethylene oxide has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). 1,2-Epoxyaethan 1,2-Epoxyethane Aethylenoxid Amprolene Anprolene Anproline Dihydrooxirene Dimethylene oxide Epoxyethane Ethene oxide Ethylene oxide ETO Oxacyclopropane Oxane Oxidoethane Oxyde d'ethylene Oxyfume Oxide, ethylene C2H4O 44.05 44.0262 oxirane ethylene oxide 184288-32-2 C1CO1 InChI=1S/C2H4O/c1-2-3-1/h1-2H2 IAYPIBMASNFSPL-UHFFFAOYSA-N belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Epoxides Organic compounds Organoheterocyclic compounds Epoxides Aliphatic heteromonocyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteromonocyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Oxirane oxacycle saturated organic heteromonocyclic parent melting_point −112.46 °C Wikipedia boiling_point 10.4 °C Wikipedia logp -0.47 ALOGPS logs 0.82 ALOGPS logp -0.047 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac oxirane ChemAxon average_mass 44.05 ChemAxon mono_mass 44.0262 ChemAxon smiles C1CO1 ChemAxon formula C2H4O ChemAxon inchi InChI=1S/C2H4O/c1-2-3-1/h1-2H2 ChemAxon inchikey IAYPIBMASNFSPL-UHFFFAOYSA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 11.04 ChemAxon polarizability 4.42 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003358 C06548 27561 6354 Oxirane Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:07 UTC 2020-08-04 22:28:23 UTC CDB000603 Ethylenediamine Ethylenediamine also known as EDDI or 1,2-diaminoethane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Ethylenediamine is an organic compound with the formula C2H4(NH2)2. It is a colorless liquid with an ammonia-like odor is a strongly basic amine. It is a widely used building block in chemical synthesis, with approximately 700,000 tonnes produced in 2017. Ethylenediamine readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health. Ethylenediamine is produced industrially by treating 1,2-dichloroethane with ammonia under pressure at 180 ¬∞C in an aqueous medium (https://doi.org/10.1002/14356007.a02_001). It is used as a precursor to chelation agents, drugs, and agrochemicals. Ethylenediamine, because it contains two amine groups, is a widely used precursor to various polymers. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). EDDI Ethylenediamine Ethylenediamine dihydrogen iodide Ethylenediamine sulfate Ethylenediamine, 3H-labeled CPD Ethyl diamine Ethane-1,2-diamine Ethylenediamine dihydrobromide 1,2-Diaminoethane Ethylenediamine (1:1) sulfite Ethylenediamine conjugate acid 1,2-Ethanediamine Edamine Ethylenediamine (1:1) sulfate Ethylenediamine hydrochloride Ethylenediamine monohydrochloride Ethylenediamine dihydrochloride Ethylenediamine phosphate Ethylenediamine dinitrate C2H10I2N2 315.93 315.8933 ethane-1,2-diamine dihydroiodide ethylenediamine dihydroiodide 8023-01-6 I.I.NCCN InChI=1S/C2H8N2.2HI/c3-1-2-4;;/h1-4H2;2*1H IWNWLPUNKAYUAW-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Monoalkylamines Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Aliphatic acyclic compounds Hydrocarbon derivatives Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine organic molecular entity logp 0.0 Wikipedia melting_point 8 °C Wikipedia boiling_point 116 °C Wikipedia logp -1.77 ALOGPS logs 0.97 ALOGPS logp -1.4 ChemAxon pka_strongest_basic 9.69 ChemAxon iupac ethane-1,2-diamine dihydroiodide ChemAxon average_mass 315.93 ChemAxon mono_mass 315.8933 ChemAxon smiles I.I.NCCN ChemAxon formula C2H10I2N2 ChemAxon inchi InChI=1S/C2H8N2.2HI/c3-1-2-4;;/h1-4H2;2*1H ChemAxon inchikey IWNWLPUNKAYUAW-UHFFFAOYSA-N ChemAxon polar_surface_area 52.04 ChemAxon refractivity 17.87 ChemAxon polarizability 7.08 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21921 C18382 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:10 UTC 2020-07-24 23:30:08 UTC CDB000604 Ethylenimine Ethylenimine, also known as aziridine or azacyclopropane, belongs to the class of organic compounds known as aziridines. These are organic compounds containing a saturated three-member heterocycle with one amino group and two methylene groups. Ethylenimine is a very strong basic compound (based on its pKa). Ethylenimine consists of a three-membered heterocycle (CH2)2NH. It is a colorless, toxic, volatile liquid that is of significant practical interest. Ethylen imine is produced industrially from aminoethanol via two related routes. The Nippon Shokubai process requires an oxide catalyst and high temperatures to affect the dehydration. In the Wenker synthesis, the aminoethanol is converted to the sulfate ester, which undergoes base-induced sulfate elimination. Older methods entailed amination of 1,2-dichloroethane and cyclization of 2-chloroethylamine. Ethylenimine has been reported to be found in soybean and wild celery. It has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Azacyclopropane Dimethyleneimine EI Ethyleneimine Ethylenimine Aziridine, conjugate acid C2H5N 43.07 43.0422 aziridine aziridine 81210-08-4 C1CN1 InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2 NOWKCMXCCJGMRR-UHFFFAOYSA-N belongs to the class of organic compounds known as aziridines. These are organic compounds containing a saturated three-member heterocycle with one amino group and two methylene groups. Aziridines Organic compounds Organoheterocyclic compounds Aziridines Aliphatic heteromonocyclic compounds Azacyclic compounds Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Aliphatic heteromonocyclic compound Amine Azacycle Aziridine Hydrocarbon derivative Organic nitrogen compound Organonitrogen compound Organopnictogen compound Secondary aliphatic amine Secondary amine azacycloalkane aziridines saturated organic heteromonocyclic parent melting_point −77.9 °C Wikipedia boiling_point 56 °C Wikipedia logp -1.07 ALOGPS logs 1.17 ALOGPS logp -0.36 ChemAxon pka_strongest_basic 8.04 ChemAxon iupac aziridine ChemAxon average_mass 43.07 ChemAxon mono_mass 43.0422 ChemAxon smiles C1CN1 ChemAxon formula C2H5N ChemAxon inchi InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2 ChemAxon inchikey NOWKCMXCCJGMRR-UHFFFAOYSA-N ChemAxon polar_surface_area 12.03 ChemAxon refractivity 12.72 ChemAxon polarizability 4.9 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB003941 9033 C11687 30969 Glucosidases Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:18 UTC 2020-07-07 15:59:59 UTC CDB000606 Eugenyl acetate Eugenyl acetate, also known as acetyleugenol, is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. Eugenyl acetate is constituted by a benzene ring, substituted by a methoxy group acetoxy group in position 1, a methoxy group in position 2 and a propenoil moiety in position 4. It is the acetylated derivative of eugenol. Eugenyl acetate is a sweet, carnation, and clove tasting compound. It is found in the highest concentration in a few different foods, such as cloves, ceylon cinnamons, and sweet bay. It has also been detected, but not quantified, in nutmegs, herbs and spices, cumins, star anises, and lemon balms. Eugenyl acetate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). 1,3,4-Eugenol acetate 1-Acetoxy-2-methoxy-4-allylbenzene 2-Methoxy-4-(2-propen-1-yl)phenyl acetate 2-Methoxy-4-(2-propenyl)phenyl acetate 4-Allyl-2-methoxyphenol acetate 4-Allyl-2-methoxyphenyl acetate Aceto eugenol Acetyl eugenol Acetyleugenol Eugenol acetate Eugenyl acetate FEMA 2469 Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetate Phenol, 2-methoxy-4-(2-propenyl)-, acetate Phenol, 4-allyl-2-methoxy-, acetate (2-Methoxy-4-prop-2-enylphenyl) acetate 2-Methoxy-4-(2-propenyl)phenol acetate Aceteugenol O-Acetyleugenol C12H14O3 206.24 206.0943 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate eugenyl acetate 93-28-7 COC1=C(OC(C)=O)C=CC(CC=C)=C1 InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3 SCCDQYPEOIRVGX-UHFFFAOYSA-N belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Phenol esters Organic compounds Benzenoids Phenol esters Aromatic homomonocyclic compounds Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Methoxybenzenes Monocarboxylic acids and derivatives Organic oxides Phenoxy compounds Alkyl aryl ether Anisole Aromatic homomonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Ether Hydrocarbon derivative Methoxybenzene Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol ester Phenol ether Phenoxy compound benzoate ester phenols melting_point 30 - 31 °C logp 3.00 ALOGPS logs -3.14 ALOGPS logp 2.52 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxy-4-(prop-2-en-1-yl)phenyl acetate ChemAxon average_mass 206.24 ChemAxon mono_mass 206.0943 ChemAxon smiles COC1=C(OC(C)=O)C=CC(CC=C)=C1 ChemAxon formula C12H14O3 ChemAxon inchi InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3 ChemAxon inchikey SCCDQYPEOIRVGX-UHFFFAOYSA-N ChemAxon polar_surface_area 35.53 ChemAxon refractivity 57.94 ChemAxon polarizability 22.28 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012393 6869 647 7136 C14567 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:23 UTC 2020-09-11 20:08:28 UTC CDB000607 Fenchyl alcohol Fenchyl alcohol, also known as fenchol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings. Fenchol or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. It is a colorless or white solid. It occurs widely in nature. The naturally occurring enantiopure (1R)-endo-(+)-fenchol is used extensively in perfumery. Fenchol gives basil its characteristic scent (DOI: https://doi.org/10.1515/znc-2007-7-808) and comprises 15.9% of the volatile oils of some species of Aster (https://doi.org/10.1016/j.foodchem.2006.03.021). Fenchyl alcohol has also been detected as a volatile component in cannabis plant samples ( PMID: 6991645, 26657499). 1,3,3-Trimethyl-2-norbornanol endo-Fenchol Fenchol Fenchol, ((endo)-(+-))-isomer Fenchol, ((exo)-(+-))-isomer Fenchol, (1R-endo)-isomer Fenchol, (1S-endo)-isomer Fenchol, (1S-exo)-isomer Fenchol, (endo)-isomer Fenchol, (exo)-isomer Fenchyl alcohol C10H18O 154.25 154.1358 (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 2217-02-9 CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 IAIHUHQCLTYTSF-OYNCUSHFSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols Alcohol Aliphatic homopolycyclic compound Bicyclic monoterpenoid Cyclic alcohol Fenchane monoterpenoid Hydrocarbon derivative Organic oxygen compound Organooxygen compound Secondary alcohol melting_point 39 to 45 °C Wikipedia boiling_point 201 °C Wikipedia logp 2.30 ALOGPS logs -2.25 ALOGPS logp 2.15 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac (1R,2R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol ChemAxon average_mass 154.25 ChemAxon mono_mass 154.1358 ChemAxon smiles CC1(C)[C@H]2CC[C@](C)(C2)[C@H]1O ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 ChemAxon inchikey IAIHUHQCLTYTSF-OYNCUSHFSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 45.16 ChemAxon polarizability 18.51 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 6997371 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:25 UTC 2020-06-30 15:36:08 UTC CDB000608 Formic acid Formic acid, also known as methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced through the oxidation of methanol. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a by-product in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer. Urinary formate is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465). Formic acid has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Acide formique Ameisensaeure Aminic acid Bilorin Formylic acid H-COOH HCO2H HCOOH Hydrogen carboxylic acid Methanoic acid Methoic acid Aminate Formylate Hydrogen carboxylate Methanoate Methoate Formate Add-F Ameisensaure Collo-bueglatt Collo-didax Formira Formisoton Methanoic acid monomer Myrmicyl Sodium formate Sybest Wonderbond hardener m 600l Calcium formate Cobalt(II) formate dihydrate Formic acid, aluminum salt Formic acid, copper salt Formic acid, cromium (+3) salt Lithium formate Ammonium formate Formic acid, ammonium (4:1) salt Formic acid, ammonium salt Formic acid, calcium salt Formic acid, copper (+2) salt Formic acid, lead (+2) salt Formic acid, lead salt Formic acid, nickel salt Formic acid, potassium salt Formic acid, strontium salt Mafusol Ammonium tetraformate Formic acid, 14C-labeled Formic acid, cobalt (+2) salt Formic acid, copper, ammonium salt Formic acid, sodium salt Formic acid, sodium salt, 14C-labeled Formic acid, ammonium (2:1) salt Formic acid, cadmium salt Formic acid, cesium salt Formic acid, copper, nickel salt Formic acid, cromium (+3), sodium (4:1:1) salt Formic acid, lithium salt Formic acid, magnesium salt Formic acid, nickel (+2) salt Formic acid, rubidium salt Formic acid, sodium salt, 13C-labeled Formic acid, thallium (+1) salt Formic acid, zinc salt Nickel formate dihydrate Aluminum formate Potassium formate Strontium formate Lead formate Nickel formate Chromic formate Cobaltous formate Cupric formate Magnesium formate Zinc formate CH2O2 46.03 46.0055 formic acid formic acid 64-18-6 OC=O InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) BDAGIHXWWSANSR-UHFFFAOYSA-N belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Carboxylic acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acids Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Saturated fatty acids Straight chain fatty acids monocarboxylic acid water_solubility 1000.0 mg/mL logp -0.54 HANSCH,C ET AL. (1995) melting_point 8.4 °C boiling_point 100.8 °C Wikipedia logp -0.47 ALOGPS logs 1.02 ALOGPS logp -0.27 ChemAxon pka_strongest_acidic 4.27 ChemAxon iupac formic acid ChemAxon average_mass 46.03 ChemAxon mono_mass 46.0055 ChemAxon smiles OC=O ChemAxon formula CH2O2 ChemAxon inchi InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) ChemAxon inchikey BDAGIHXWWSANSR-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 8.15 ChemAxon polarizability 3.37 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon C00058 DB01942 FDB012804 30751 284 C00001182 FORMATE Formic_acid Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31. 22292465 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:29 UTC 2020-08-04 22:28:23 UTC CDB000609 Furfural Furfural, also known as 2-furaldehyde or 2-furyl-methanal, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. It is an aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group. It is a colorless liquid, although commercial samples are often brown. It is a product of the dehydration of sugars, as occur in a variety of agricultural by-products, including corncobs, oat, wheat bran, and sawdust. Furfural was first isolated in 1821 by the German chemist Johann Wolfgang D√∂bereiner, who produced a small sample as a by-product of formic acid synthesis. Furfural dissolves readily in most polar organic solvents, but it is only slightly soluble in either water or alkanes. Furfural has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Furfural is a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 2-Formylfuran 2-Furaldehyde 2-Furanaldehyde 2-Furancarbonal 2-Furyl-methanal 2-Furylcarboxaldehyde Furaldehyde 2-Formyl furan 2-Formylofuran 2-Furaldehyde, 8ci 2-Furancarboxyaldehyde 2-Furfural 2-Furfuraldehyde 2-Furylaldehyde 2-Furylaldehyde xypropane 2-Furylmethanal a-Furfuraldehyde a-Furole alpha-Furfuraldehyde alpha-Furole FEMA 2489 Fural Furale Furan-2-aldehyde Furan-2-carbaldehyde Furan-2-carboxaldehyde Furancarbonal Furfural Furfuraldehyde Furfurale Furfuralu Furfurol Furfurole Furfurylaldehyde Furol Furole Furyl-methanal 2-Furancarboxaldehyde C5H4O2 96.08 96.0211 furan-2-carbaldehyde bran oil 98-01-1 O=CC1=CC=CO1 InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H HYBBIBNJHNGZAN-UHFFFAOYSA-N belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. Aryl-aldehydes Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic heteromonocyclic compounds Furans Heteroaromatic compounds Hydrocarbon derivatives Organic oxides Oxacyclic compounds Aromatic heteromonocyclic compound Aryl-aldehyde Furan Heteroaromatic compound Hydrocarbon derivative Organic oxide Organoheterocyclic compound Oxacycle a small molecule aldehyde furans water_solubility 74.1 mg/mL at 25 °C logp 0.41 melting_point -37 °C boiling_point 162 °C Wikipedia logp 0.43 ALOGPS logs -0.79 ALOGPS logp 0.75 ChemAxon pka_strongest_basic -3 ChemAxon iupac furan-2-carbaldehyde ChemAxon average_mass 96.08 ChemAxon mono_mass 96.0211 ChemAxon smiles O=CC1=CC=CO1 ChemAxon formula C5H4O2 ChemAxon inchi InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H ChemAxon inchikey HYBBIBNJHNGZAN-UHFFFAOYSA-N ChemAxon polar_surface_area 30.21 ChemAxon refractivity 25.03 ChemAxon polarizability 8.87 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB004219 7362 13863629 C00030331 C14279 CPD0-2357 Furfural FU2 34768 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:32 UTC 2020-07-24 23:30:19 UTC CDB000610 Furfurylmethylamphetamine Furfurylmethylamphetamine or Furfenorex, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. It is an anorexic drug used in the treatment of obesity (PMID: 2874966). One of its metabolites was methamphetamine and has been withdrawn from the market due to abuse potential (PMID: 12024689). It is also a stimulant, which enhances the central nervous system activity by mimicking the action of brain neurotransmitters and, due to the ability to increase awareness and counteract fatigue, is misused by athletes participating in sports that require high levels of physical and mental endurances (DOI: 10.1002/9781118533956). Furfurylmethylamphetamine has also been detected as a volatile component in cannabis plant samples obtained from police seizures (PMID: 26657499). C15H19NO 229.32 229.1467 [(furan-2-yl)methyl](methyl)[(2S)-1-phenylpropan-2-yl]amine (furan-2-ylmethyl)(methyl)[(2S)-1-phenylpropan-2-yl]amine 3776-93-0 C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CO1 InChI=1S/C15H19NO/c1-13(11-14-7-4-3-5-8-14)16(2)12-15-9-6-10-17-15/h3-10,13H,11-12H2,1-2H3/t13-/m0/s1 DLGIIZAHQPTVCJ-ZDUSSCGKSA-N belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Amphetamines and derivatives Organic compounds Benzenoids Benzene and substituted derivatives Phenethylamines Aromatic heteromonocyclic compounds Aralkylamines Furans Heteroaromatic compounds Hydrocarbon derivatives Organooxygen compounds Oxacyclic compounds Phenylpropanes Trialkylamines Amine Amphetamine or derivatives Aralkylamine Aromatic heteromonocyclic compound Furan Heteroaromatic compound Hydrocarbon derivative Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Oxacycle Phenylpropane Tertiary aliphatic amine Tertiary amine logp 3.61 ALOGPS logs -3.63 ALOGPS logp 3.4 ChemAxon pka_strongest_basic 8.76 ChemAxon iupac [(furan-2-yl)methyl](methyl)[(2S)-1-phenylpropan-2-yl]amine ChemAxon average_mass 229.32 ChemAxon mono_mass 229.1467 ChemAxon smiles C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CO1 ChemAxon formula C15H19NO ChemAxon inchi InChI=1S/C15H19NO/c1-13(11-14-7-4-3-5-8-14)16(2)12-15-9-6-10-17-15/h3-10,13H,11-12H2,1-2H3/t13-/m0/s1 ChemAxon inchikey DLGIIZAHQPTVCJ-ZDUSSCGKSA-N ChemAxon polar_surface_area 16.38 ChemAxon refractivity 70.78 ChemAxon polarizability 25.63 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 71777433 Harris LS: The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology. Drug Alcohol Depend. 1986 Jun;17(2-3):107-18. doi: 10.1016/0376-8716(86)90002-5. 2874966 Cody JT: Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results. J Occup Environ Med. 2002 May;44(5):435-50. doi: 10.1097/00043764-200205000-00012. 12024689 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:35 UTC 2020-08-04 22:28:23 UTC CDB000611 gamma-Gurjunene Œ≥-Gurjunene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Œ≥-Gurjunene has been detected as a volatile component in cannabis plant samples ( PMID: 6991645, 26657499). It was also identified in the shoots and nutlets of Carya illinoinensis (Pecan) (6.69% - 11.3% relative to total volatile compounds) (PMID: 21604354), the essential oil of Baccharis L. species (1.1 ‚Äì 23.6% relative to total volatile compounds) (DOI: 10.1007/s00606-005-0296-6), the essential oil of Hypericum montbretii Spach (6.1-11.6% relative to total oil content) (DOI: 10.15547/ast.2018.03.050), the essential oil of Psidium L. (Guava) (PMID: 31286378). C15H24 204.36 204.1878 (1S,3aS,4R,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene (1S,3aS,4R,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene 22567-17-5 C[C@H]1CC[C@H]2[C@H](C)CC[C@H](C=C12)C(C)=C InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h9,11-14H,1,5-8H2,2-4H3/t11-,12+,13-,14+/m1/s1 DUYRYUZIBGFLDD-RQJABVFESA-N logp 5.73 ALOGPS logs -4.57 ALOGPS logp 4.51 ChemAxon iupac (1S,3aS,4R,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene ChemAxon average_mass 204.36 ChemAxon mono_mass 204.1878 ChemAxon smiles C[C@H]1CC[C@H]2[C@H](C)CC[C@H](C=C12)C(C)=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h9,11-14H,1,5-8H2,2-4H3/t11-,12+,13-,14+/m1/s1 ChemAxon inchikey DUYRYUZIBGFLDD-RQJABVFESA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 67.53 ChemAxon polarizability 26.27 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 131705829 Lukowski A, Maderek E, Giertych MJ, Karolewski P: Sex Ratio and Body Mass of Adult Herbivorous Beetles Depend on Time of Occurrence and Light Conditions. PLoS One. 2015 Dec 14;10(12):e0144718. doi: 10.1371/journal.pone.0144718. eCollection 2015. 26657564 Corella-Madueno MA, Harris MK, Fu-Castillo AA, Martinez-Tellez MA, Valenzuela-Soto EM, Galvez-Ruiz JC, Vargas-Arispuro I: Volatiles emitted by Carya illinoinensis (Wang.) K. Koch as a prelude for semiochemical investigations to focus on Acrobasis nuxvorella Nuenzig (Lepidoptera: Pyralidae). Pest Manag Sci. 2011 Dec;67(12):1522-7. doi: 10.1002/ps.2205. Epub 2011 May 20. 21604354 Vasconcelos LC, de Souza Santos E, de Oliveira Bernardes C, da Silva Ferreira MF, Ferreira A, Tuler AC, Carvalho JAM, Pinheiro PF, Praca-Fontes MM: Phytochemical analysis and effect of the essential oil of Psidium L. species on the initial development and mitotic activity of plants. Environ Sci Pollut Res Int. 2019 Sep;26(25):26216-26228. doi: 10.1007/s11356-019-05912-6. Epub 2019 Jul 8. 31286378 Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. 19932496 Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. 17710406 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:37 UTC 2020-08-04 22:28:23 UTC CDB000612 gamma-Hexalactone Œ≥-Hexalactone also known as Œ≥-Caprolactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with one oxygen atom, four carbon atoms, and a ketone group on the carbon adjacent to the oxygen atom. Thus, Œ≥-caprolactone is considered to be a fatty ester lipid molecule. Œ≥-caprolactone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Œ≥-Caprolactone is occasionally found as a volatile component of human urine. In some cases, differences up to one order of magnitude are observed. Œ≥-Caprolactone has also been found in the polar fraction of human blood. Œ≥-Caprolactone has been detected, but not quantified, in several different plants, such as potato, cereals and cereal products, pomes, alcoholic beverages, and fruits. Œ≥-Caprolactone has been detected as a volatile component in cannabis plant samples (PMID: 26657499). C6H10O2 114.14 114.0681 (5S)-5-ethyloxolan-2-one (5S)-5-ethyloxolan-2-one 41035-07-8 CC[C@H]1CCC(=O)O1 InChI=1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3/t5-/m0/s1 JBFHTYHTHYHCDJ-YFKPBYRVSA-N belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Gamma butyrolactones Organic compounds Organoheterocyclic compounds Lactones Gamma butyrolactones Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Oxolanes Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Gamma butyrolactone Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Oxolane logp 0.77 ALOGPS logs -0.71 ALOGPS logp 1.09 ChemAxon pka_strongest_basic -7 ChemAxon iupac (5S)-5-ethyloxolan-2-one ChemAxon average_mass 114.14 ChemAxon mono_mass 114.0681 ChemAxon smiles CC[C@H]1CCC(=O)O1 ChemAxon formula C6H10O2 ChemAxon inchi InChI=1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3/t5-/m0/s1 ChemAxon inchikey JBFHTYHTHYHCDJ-YFKPBYRVSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 29.25 ChemAxon polarizability 12.22 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 5325911 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:41 UTC 2020-07-07 16:00:03 UTC CDB000613 Hexanoic acid, methyl ester Methyl hexanoate, also known as Hexanoic acid, methyl ester, belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. Methyl hexanoate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Methyl hexanoate is a sweet, ether, and fresh tasting compound. It has been detected, but not quantified, in several different foods, such as garden tomato, cereals and cereal products, potato, blackberries, and pineapples. It is also present in wine grapes, melon, raspberry, blackberry, plum, quince, apple brandy, wines, bourbon vanilla, coffee, black tea, potato, tomato, cheeses, rye bread, meats and other foodstuffs. Methyl hexanoate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Caproic acid, methyl ester Hexanoic acid, methyl ester Methyl caproate Methyl capronate Methyl hexoate Methyl hexylate Methyl N-hexanoate Caproate, methyl ester Hexanoate, methyl ester Methyl caproic acid Methyl capronic acid Methyl hexoic acid Methyl hexylic acid Methyl N-hexanoic acid Methyl hexanoic acid Caproic acid methyl ester FEMA 2708 Hexanoic acid,methyl ester Methyl ester OF hexanoic acid Methyl N-hexoate N-Caproic acid methyl ester Hexanoic acid methyl ester C7H14O2 130.18 130.0994 methyl hexanoate methyl hexanoate 106-70-7 CCCCCC(=O)OC InChI=1S/C7H14O2/c1-3-4-5-6-7(8)9-2/h3-6H2,1-2H3 NUKZAGXMHTUAFE-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Fatty acid methyl esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Carbonyl compounds Hydrocarbon derivatives Methyl esters Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid methyl ester Hydrocarbon derivative Methyl ester Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters fatty acid methyl ester water_solubility 1.33 mg/mL at 20 °C melting_point -71 °C logp 2.38 ALOGPS logs -1.76 ALOGPS logp 1.96 ChemAxon pka_strongest_basic -7 ChemAxon iupac methyl hexanoate ChemAxon average_mass 130.18 ChemAxon mono_mass 130.0994 ChemAxon smiles CCCCCC(=O)OC ChemAxon formula C7H14O2 ChemAxon inchi InChI=1S/C7H14O2/c1-3-4-5-6-7(8)9-2/h3-6H2,1-2H3 ChemAxon inchikey NUKZAGXMHTUAFE-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 35.84 ChemAxon polarizability 15.27 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB013896 7536 77322 7824 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:45 UTC 2020-07-10 00:17:46 UTC CDB000614 Hexanoic acid, propyl ester Hexanoic acid, propyl ester or propyl hexanoate, also known as propyl caproate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. A hexanoate ester obtained by the formal condensation of the carboxyl group of hexanoic acid (caproic acid) with propan-1-ol. Hexanoic acid, propyl ester is a very hydrophobic molecule, practically insoluble in water. Propyl hexanoate is a sweet, fruity, and green tasting compound. It has been detected, but not quantified, in several different foods, such as alcoholic beverages, milk and milk products, fruits, asian pears, and sweet cherries. Propyl hexanoate has also been detected as a volatile component in cannabis plant samples (PMID: 26657499). Hexanoic acid is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). Caproic acid propyl ester Caproyl acid propyl ester Hexanoic acid propyl ester N-Propyl hexanoaten Propyl caproate Caproate propyl ester Hexanoate propyl ester Propyl caproic acid Propyl hexanoic acid FEMA 2949 Hexanoic acid, propyl ester N-Propyl hexanoate N-Propyl N-hexanoate Propionyl hexanoic acid C9H18O2 158.24 158.1307 propyl hexanoate propyl hexanoate 626-77-7 CCCCCC(=O)OCCC InChI=1S/C9H18O2/c1-3-5-6-7-9(10)11-8-4-2/h3-8H2,1-2H3 HTUIWRWYYVBCFT-UHFFFAOYSA-N belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Fatty acid esters Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Wax monoesters fatty acid ester melting_point -69 °C logp 3.30 ALOGPS logs -2.61 ALOGPS logp 2.84 ChemAxon pka_strongest_basic -7 ChemAxon iupac propyl hexanoate ChemAxon average_mass 158.24 ChemAxon mono_mass 158.1307 ChemAxon smiles CCCCCC(=O)OCCC ChemAxon formula C9H18O2 ChemAxon inchi InChI=1S/C9H18O2/c1-3-5-6-7-9(10)11-8-4-2/h3-8H2,1-2H3 ChemAxon inchikey HTUIWRWYYVBCFT-UHFFFAOYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 45.12 ChemAxon polarizability 19.4 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012451 11790 12293 87365 Propyl hexanoate Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:47 UTC 2020-08-04 22:28:23 UTC CDB000615 Hexestrol Hexestrol also known as hexanestrol, hexoestrol, and dihydrodiethylstilbestrol, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Along with diethylstilbestrol, hexestrol is one of the most potent known estrogens (PMID: 21013428). It is a synthetic nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol which was used to treat estrogen deficiency. Hexestrol has been available and used in ester forms, such as hexestrol diacetate, hexestrol dicaprylate, hexestrol diphosphate, and hexestrol dipropionate. When compared to estradiol, hexestrol has approximately 302% and 234% of the affinity the estrogen receptors ERŒ± and ERŒ≤, respectively (PMID: 9048584). Hexestrol has also been found in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). HEXESTROL diphosphATE sodium HEXESTROL diphosphoric acid sodium 4,4'-(Diethylideneethylene)diphenol Dienestrol, (e,e)-isomer Dienoestrol ortho Brand OF dienestrol ortho Dienestrol Synestrol Dienestrol, (Z,e)-isomer Dienestrol, (Z,Z)-isomer Oestrasid Dienestrol Dihydrodiethylstilbestrol Hexestrol, (r*,r*)-(+-)-isomer Hexestrol, (r*,s*)-isomer Hexestrol, (R-(r*,r*))-isomer Hexestrol, (S-(r*,r*))-isomer C18H22O2 270.37 270.162 4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol hexestrol 84-16-2 CC[C@@H]([C@@H](CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+ PBBGSZCBWVPOOL-HDICACEKSA-N belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Stilbenes Organic compounds Phenylpropanoids and polyketides Stilbenes Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Hydrocarbon derivatives Organooxygen compounds Phenylpropanes 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Phenylpropane Stilbene logp 4.98 ALOGPS logs -4.29 ALOGPS logp 5.37 ChemAxon pka_strongest_acidic 9.93 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 4-[(3R,4S)-4-(4-hydroxyphenyl)hexan-3-yl]phenol ChemAxon average_mass 270.37 ChemAxon mono_mass 270.162 ChemAxon smiles CC[C@@H]([C@@H](CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1 ChemAxon formula C18H22O2 ChemAxon inchi InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+ ChemAxon inchikey PBBGSZCBWVPOOL-HDICACEKSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 82.66 ChemAxon polarizability 31.31 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon DB07931 192197 Hexestrol SOLMSSEN UV: Synthetic estrogens and the relation between their structure and their activity. Chem Rev. 1945 Dec;37:481-598. doi: 10.1021/cr60118a004. 21013428 Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. doi: 10.1210/endo.138.3.4979. 9048584 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:50 UTC 2020-06-30 16:41:10 UTC CDB000616 Hydrazine Hydrazine is an inorganic chemical compound with the formula N2H4. It is a colourless liquid with an ammonia-like odor and it is derived from the same industrial chemical processes used to manufacture ammonia. However, hydrazine has physical properties that are more similar to those of water. Direct alkylation of hydrazines with alkyl halides in the presence of base affords alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on level of substitution (same as in ordinary amines). The reduction of hydrazones to hydrazines presents a clean path for the production of 1,1-dialkylated hydrazines. Being bifunctional, with two amines, hydrazine is a key building block for the preparation of many heterocyclic compounds via condensation with a range of difunctional electrophiles. With 2,4-pentanedione, it condenses to give the 3,5-dimethylpyrazole. In the Einhorn-Brunner reaction, hydrazines react with imides to give triazoles. Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, it is used as an antioxidant, an oxygen scavenger, and a corrosion inhibitor in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in electroless nickel plating and plutonium extraction from nuclear reactor waste. Hidrazine has been reported to occur naturally in tabaco and it was detected in the smoke of cigarettes (PMID: 4840592). Hydrazine has also been reported as a volatile component of cannabis samples seized by police (PMID: 26657499). Diamine H2NNH2 Hydrazin N2H4 Nitrogen hydride Amerzine Catalyzed hydrazine Diamide Diazane HDZ Hydrazine (anhydrous) Hydrazine (hydrazine sulfate) Hydrazine (hydrazine sulphate) Hydrazine base Hydrazine solution Hydrazines Hydrazyna Levoxine Oxytreat 35 Scav-ox II Zerox Hydrazine mononitrate Hydrazine phosphate (2:1) Segidrin Hydrazine dihydrochloride Hydrazine monohydrate Hydrazine sulfate Hydrazine tartrate Hydrazine phosphate (1:1) Hydrazine sulfate (2:1) Hydrazine hydrate Hydrazine nitrate Hydrazine sulfate (1:1) monosodium salt H4N2 32.05 32.0374 hydrazine hydrazine 302-01-2 NN InChI=1S/H4N2/c1-2/h1-2H2 OAKJQQAXSVQMHS-UHFFFAOYSA-N belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'. Homogeneous other non-metal compounds Inorganic compounds Homogeneous non-metal compounds Homogeneous other non-metal compounds Hydrazines and derivatives Homogeneous other non metal Hydrazine derivative a small molecule azane hydrazines water_solubility 1000 mg/mL logp -2.07 HANSCH,C ET AL. (1995) melting_point 2 °C boiling_point 114 °C Wikipedia logp -1 ChemAxon pka_strongest_basic 5.4 ChemAxon iupac hydrazine ChemAxon average_mass 32.05 ChemAxon mono_mass 32.0374 ChemAxon smiles NN ChemAxon formula H4N2 ChemAxon inchi InChI=1S/H4N2/c1-2/h1-2H2 ChemAxon inchikey OAKJQQAXSVQMHS-UHFFFAOYSA-N ChemAxon polar_surface_area 52.04 ChemAxon refractivity 10.57 ChemAxon polarizability 3.25 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 8960 FDB013394 9321 C05361 15571 4-HYDROXYMETHYLPHENYLHYDRAZINE Hydrazine Liu YY, Schmeltz I, Hoffmann D: Chemical studies on tobacco smoke. Quantitative analysis of hydrazine in tobacco and cigarette smoke. Anal Chem. 1974 Jun;46(7):885-9. doi: 10.1021/ac60343a046. 4840592 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:53 UTC 2020-07-24 23:30:08 UTC CDB000617 Isobornyl thiocyanoacetate Isobornyl thiocyanoacetate, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. It is a yellow oily liquid with a terpene-like odor. Isobornyl thiocyanoacetate is practically insoluble in water but it is very soluble in alcohol, benzene, chloroform, and ether. Isobornyl thiocyanoacetate or thanite is an insecticide, used to control ants, houseflies. It is used as fungicide to preserve industrial products such as glue, leather, paints, dyes, paper, and synthetic textile materials. Isobornyl thiocyanoacetate has been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499). Isobornyl thiocyanoacetic acid Isobornyl thiocyanoacetate, (exo)-isomer Thanite C13H19NO2S 253.36 253.1136 (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-(cyanosulfanyl)acetate (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl (cyanosulfanyl)acetate 115-31-1 CC1(C)[C@@H]2CC[C@]1(C)[C@H](C2)OC(=O)CSC#N InChI=1S/C13H19NO2S/c1-12(2)9-4-5-13(12,3)10(6-9)16-11(15)7-17-8-14/h9-10H,4-7H2,1-3H3/t9-,10+,13-/m1/s1 IXEVGHXRXDBAOB-GBIKHYSHSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Sulfenyl compounds Thiocyanates Aliphatic homopolycyclic compound Bicyclic monoterpenoid Bornane monoterpenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Sulfenyl compound Thiocyanate logp 3.45 ALOGPS logs -3.52 ALOGPS logp 2.71 ChemAxon pka_strongest_basic -7.2 ChemAxon iupac (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-(cyanosulfanyl)acetate ChemAxon average_mass 253.36 ChemAxon mono_mass 253.1136 ChemAxon smiles CC1(C)[C@@H]2CC[C@]1(C)[C@H](C2)OC(=O)CSC#N ChemAxon formula C13H19NO2S ChemAxon inchi InChI=1S/C13H19NO2S/c1-12(2)9-4-5-13(12,3)10(6-9)16-11(15)7-17-8-14/h9-10H,4-7H2,1-3H3/t9-,10+,13-/m1/s1 ChemAxon inchikey IXEVGHXRXDBAOB-GBIKHYSHSA-N ChemAxon polar_surface_area 50.09 ChemAxon refractivity 68.05 ChemAxon polarizability 38.95 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 220601 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:46:56 UTC 2020-07-24 23:30:08 UTC CDB000618 Isobutane Isobutane or 2-Methylpropane, also known as (CH3)2ch-CH3, belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. It is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. It is the simplest alkane with a tertiary carbon. Propellant/aerating agent used in foods. Recent concerns with depletion of the ozone layer by freon gases have led to increased use of isobutane as a gas for refrigeration systems, especially in domestic refrigerators and freezers, and as a propellant in aerosol sprays. When used as a refrigerant or a propellant, isobutane is also known as R-600a. Some portable camp stoves use a mixture of isobutane with propane, usually 80:20. Isobutane is used as a feedstock in the petrochemical industry, for example in the synthesis of isooctane. Its UN number (for hazardous substances see shipping) is UN 1969. Isobutane is the R group for the amino acid leucine. Isobutane is obtained by isomerization of butane. (CH3)2ch-CH3 e943b R-600a C4H10 58.12 58.0783 2-methylpropane isobutane 75-28-5 CC(C)C InChI=1S/C4H10/c1-4(2)3/h4H,1-3H3 NNPPMTNAJDCUHE-UHFFFAOYSA-N belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2. Branched alkanes Organic compounds Hydrocarbons Saturated hydrocarbons Alkanes Aliphatic acyclic compounds Aliphatic acyclic compound Branched alkane alkane water_solubility 48.9 mg/L at 25 °C Wikipedia melting_point −159.42 °C Wikipedia boiling_point −11.7 °C Wikipedia logp 2.16 ALOGPS logs -1.74 ALOGPS logp 2.08 ChemAxon iupac 2-methylpropane ChemAxon average_mass 58.12 ChemAxon mono_mass 58.0783 ChemAxon smiles CC(C)C ChemAxon formula C4H10 ChemAxon inchi InChI=1S/C4H10/c1-4(2)3/h4H,1-3H3 ChemAxon inchikey NNPPMTNAJDCUHE-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 20.15 ChemAxon polarizability 8.18 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB000755 DBMET01512 6360 30363 Isobutane 1.0 2020-03-19 00:46:59 UTC 2020-07-10 00:17:46 UTC CDB000619 Isoquinoline Isoquinoline, also known as 2-benzazine, belongs to the class of organic compounds known as isoquinolines and derivatives. Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. Isoquinoline is a weak basic compound (based on its pKa). Being an analog of pyridine, isoquinoline is a weak base, with a pKb of 8.6. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3. Isoquinoline is a colorless hygroscopic liquid at room temperature with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes as platelets that poorly soluble in water but dissolve well in organic solvents such as ethanol, acetone, and diethyl ether. It is also soluble in diluted acids, due to the formation of the protonated salt derivative. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine and morphine. The isoquinoline ring in these natural compounds derives from the aromatic amino acid tyrosine. Isoquinoline has also been detected in the volatile fraction of Cannabis sativa samples, obtained from police seizures (PMID: 26657499). Isoquinoline is also found in cannabis smoke and is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). 2-Benzazine Benzo[c]pyridine Isochinolin 2-Azanaphthalene 2-Benzanine 3,4-Benzopyridine Benzo(c)pyridine Benzopyridine beta -Quinoline beta-Quinoline FEMA 2978 ISQ Isoquinoline sulfate (1:1) Isoquinoline hydrobromide Isoquinoline hydrochloride Isoquinoline hydroiodide Isoquinoline conjugate acid C9H7N 129.16 129.0578 isoquinoline isoquinoline 119-65-3 C1=CC=C2C=NC=CC2=C1 InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H AWJUIBRHMBBTKR-UHFFFAOYSA-N belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. Isoquinolines and derivatives Organic compounds Organoheterocyclic compounds Isoquinolines and derivatives Aromatic heteropolycyclic compounds Azacyclic compounds Benzenoids Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Pyridines and derivatives Aromatic heteropolycyclic compound Azacycle Benzenoid Heteroaromatic compound Hydrocarbon derivative Isoquinoline Organic nitrogen compound Organonitrogen compound Organopnictogen compound Pyridine a small molecule azaarene isoquinolines mancude organic heterobicyclic parent ortho-fused heteroarene water_solubility 4.52 mg/mL at 25 °C logp 2.08 melting_point 25.5 - 26 °C boiling_point 242 °C Wikipedia logp 2.14 ALOGPS logs -1.66 ALOGPS logp 1.75 ChemAxon pka_strongest_basic 5.26 ChemAxon iupac isoquinoline ChemAxon average_mass 129.16 ChemAxon mono_mass 129.0578 ChemAxon smiles C1=CC=C2C=NC=CC2=C1 ChemAxon formula C9H7N ChemAxon inchi InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H ChemAxon inchikey AWJUIBRHMBBTKR-UHFFFAOYSA-N ChemAxon polar_surface_area 12.89 ChemAxon refractivity 40.35 ChemAxon polarizability 13.85 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB012557 8405 8098 16092 ISQ C06323 DB04329 ISOQUINOLINE Isoquinoline Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:02 UTC 2020-08-04 22:28:23 UTC CDB000620 Limonene dioxide Limonene dioxide or Limonene diepoxide belongs to the class of organic compounds known as menthane monoterpenoids. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Menthanes are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and an isopropyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Limonene dioxide is the di-epoxylated derivative of limonene. Limonene is a colorless liquid and is the major component in the oil of citrus fruit peels. Limonene is common as a dietary supplement and as a fragrance ingredient for cosmetics products. Limonene dioxide has been detected as a volatile component in cannabis plant samples (PMID: 26657499). C10H16O2 168.24 168.115 (1S,4S,6R)-1-methyl-4-[(2S)-2-methyloxiran-2-yl]-7-oxabicyclo[4.1.0]heptane (1S,4S,6R)-1-methyl-4-[(2S)-2-methyloxiran-2-yl]-7-oxabicyclo[4.1.0]heptane 96-08-2 C[C@@]1(CO1)[C@H]1CC[C@]2(C)O[C@@H]2C1 InChI=1S/C10H16O2/c1-9-4-3-7(5-8(9)12-9)10(2)6-11-10/h7-8H,3-6H2,1-2H3/t7-,8+,9-,10+/m0/s1 RBHIUNHSNSQJNG-QCLAVDOMSA-N logp 1.44 ALOGPS logs -1.91 ALOGPS logp 1.39 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (1S,4S,6R)-1-methyl-4-[(2S)-2-methyloxiran-2-yl]-7-oxabicyclo[4.1.0]heptane ChemAxon average_mass 168.24 ChemAxon mono_mass 168.115 ChemAxon smiles C[C@@]1(CO1)[C@H]1CC[C@]2(C)O[C@@H]2C1 ChemAxon formula C10H16O2 ChemAxon inchi InChI=1S/C10H16O2/c1-9-4-3-7(5-8(9)12-9)10(2)6-11-10/h7-8H,3-6H2,1-2H3/t7-,8+,9-,10+/m0/s1 ChemAxon inchikey RBHIUNHSNSQJNG-QCLAVDOMSA-N ChemAxon polar_surface_area 25.06 ChemAxon refractivity 45.26 ChemAxon polarizability 18.66 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 121492667 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:05 UTC 2020-08-04 22:28:23 UTC CDB000621 Linalyl acetate Linalyl acetate belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of monoterpenes. Linalyl acetate occurs naturally and is found in many flowers and spices. It can be isolated from numerous plants and essential oils, such as clary sage, lavender, lemon, cardamom. It is also one of the principal components of the essential oils of bergamot and lavender. Chemically, it is the acetate ester of linalool, and the two often occur in conjunction. Linalyl acetate is a flavouring ingredient and it tastes similar to how it smells, with a pleasant fruity odor reminiscent of bergamot mint oil. It is found in Eau de Cologne mint. As a volatile terpene, linalyl acetate is also combustible. Linalyl acetate has been detected as a volatile component in cannabis plant samples (PMID: 26657499). (+-)-3,7-Dimethylocta-1,6-dien-3-yl acetate Acetic acid linalool ester Bergamiol Bergamot mint oil (+-)-3,7-Dimethylocta-1,6-dien-3-yl acetic acid Acetate linalool ester (-)-Linalyl acetic acid (-)-Linalyl acetate (R)-Linalyl acetic acid R-(-)-Linalyl acetate R-Linalyl acetate l-Linalyl acetate (-)-(R)-3-Acetoxy-3,7-dimethylocta-1,6-diene Linalool acetate (±)-Linaloyl acetate (±)-Linalyl acetate 1,5-Dimethyl-1-vinyl-4-hexenyl acetate 3,7-Dimethyl-1,6-octadien-3-yl acetate 3,7-Dimethylocta-1,6-dien-3-yl acetate 3-Acetoxy-3,7-dimethyl-1,6-octadiene Bergamol dl-Linalool acetate C12H20O2 196.29 196.1463 (3R)-3,7-dimethylocta-1,6-dien-3-yl acetate (+-)-linalyl acetate 16509-46-9 CC(C)=CCC[C@@](C)(OC(C)=O)C=C InChI=1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3/t12-/m0/s1 UWKAYLJWKGQEPM-LBPRGKRZSA-N belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Acyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Acyclic monoterpenoid Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound 3,7-dimethylocta-1,6-dien-3-yl acetate Acyclic monoterpenoids Acyclic monoterpenoids Linear monoterpenes boiling_point 220 °C Wikipedia logp 4.03 ALOGPS logs -3.51 ALOGPS logp 3.09 ChemAxon pka_strongest_basic -7 ChemAxon iupac (3R)-3,7-dimethylocta-1,6-dien-3-yl acetate ChemAxon average_mass 196.29 ChemAxon mono_mass 196.1463 ChemAxon smiles CC(C)=CCC[C@@](C)(OC(C)=O)C=C ChemAxon formula C12H20O2 ChemAxon inchi InChI=1S/C12H20O2/c1-6-12(5,14-11(4)13)9-7-8-10(2)3/h6,8H,1,7,9H2,2-5H3/t12-/m0/s1 ChemAxon inchikey UWKAYLJWKGQEPM-LBPRGKRZSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 59.36 ChemAxon polarizability 23.13 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB006042 442474 C09863 6469 C00003048 Linalyl_acetate Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:09 UTC 2020-08-04 22:28:23 UTC CDB000622 lsoamyl alcohol Isoamyl alcohol or Isopentanol, also known as isopentyl alcohol or iso-amylalkohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the alcohol functional group, attached to a primary carbon, with the general structure RCOH (R=alkyl, aryl). Isoamyl alcohol is a very hydrophobic molecule, practically insoluble in water but readily soluble in organic solvents such as methanol, ethanol and ethyl acetate. Thus, isopentanol is considered to be a fatty alcohol lipidic molecule. Isopentyl alcohol is one of several isomers of amyl alcohol. It is a by-product of gut microbial fermentation (PMID: 17452087). Isopentanol is an alcoholic, banana, and burnt tasting compound. Due to its flavour and aroma, it is an ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. Isoamyl alcohol can be produced by 3-methylbutanal reductase (EC 1.1.1.265) from 3-methylbutanal. In alcoholic beverages, isopentyl alcohol is also the major higher chain alcohol and it is present in cider, mead, beer, wine, and spirits to varying degrees, being a product of the fermentation of starches. Isopentanol has been shown to induce expression of CYP3A and CYP2E1 in human liver (PMID: 7574728). Isoamyl alcohol has been detected as a volatile component in cannabis plant samples (PMID: 26657499). 1-HYDROXY-3-methylbutane 2-Methyl-4-butanol 3-Methyl-1-butanol 3-Methylbutanol Alcool isoamylique I-amyl alcohol Iso-amylalkohol Isoamyl alcohol Isobutylcarbinol Isopentan-1-ol Isopentyl alcohol Isopentylalkohol Primary isoamyl alcohol 3-Methyl-butan-(1)-ol 3-Methyl-butanol 3-Methylbutan-1-ol 3-MethylbutanoI Butan-1-ol, 3-methyl Fermentation amyl alcohol Fusel oil Iso-amyl alcohol Isoamyl alcohol (3-methyl butanol) Isoamyl alcohol (natural) Isoamyl alkohol Isoamylalcohol Isoamylol Isobutyl carbinol Methyl-3-butan-1-ol Isopentyl alcohol, barium salt Isopentyl alcohol, magnesium salt Isopentyl alcohol, sodium salt Isopentyl alcohol, lead (2+) salt Isopentyl alcohol, potassium salt Isopentyl alcohol, strontium salt Isopentyl alcohol, 1-(14)C-labeled Isopentanol C5H12O 88.15 88.0888 3-methylbutan-1-ol isoamyl alcohol 123-51-3 CC(C)CCO InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 PHTQWCKDNZKARW-UHFFFAOYSA-N belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Primary alcohols Organic compounds Organic oxygen compounds Organooxygen compounds Alcohols and polyols Aliphatic acyclic compounds Hydrocarbon derivatives Aliphatic acyclic compound Hydrocarbon derivative Primary alcohol Fatty alcohols a small molecule alkyl alcohol primary alcohol water_solubility 26.7 mg/mL at 25 °C logp 1.16 HANSCH,C ET AL. (1995) melting_point -117.2 °C logp 1.33 ALOGPS logs -0.37 ALOGPS logp 1.09 ChemAxon pka_strongest_acidic 17.17 ChemAxon pka_strongest_basic -1.9 ChemAxon iupac 3-methylbutan-1-ol ChemAxon average_mass 88.15 ChemAxon mono_mass 88.0888 ChemAxon smiles CC(C)CCO ChemAxon formula C5H12O ChemAxon inchi InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 ChemAxon inchikey PHTQWCKDNZKARW-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 26.68 ChemAxon polarizability 11.03 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon FDB008131 29000 31260 DB02296 C07328 15837 CPD-7032 Isoamyl alcohol IP3 Boumba VA, Ziavrou KS, Vougiouklakis T: Biochemical pathways generating post-mortem volatile compounds co-detected during forensic ethanol analyses. Forensic Sci Int. 2008 Jan 30;174(2-3):133-51. doi: 10.1016/j.forsciint.2007.03.018. Epub 2007 Apr 23. 17452087 Kostrubsky VE, Strom SC, Wood SG, Wrighton SA, Sinclair PR, Sinclair JF: Ethanol and isopentanol increase CYP3A and CYP2E in primary cultures of human hepatocytes. Arch Biochem Biophys. 1995 Oct 1;322(2):516-20. doi: 10.1006/abbi.1995.1495. 7574728 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:11 UTC 2020-07-24 23:30:08 UTC CDB000623 lsobornyl acetate Isobornyl acetate, also known as pichtosin, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Isobornyl acetate has been detected in the oils of valerian root (PMID: 1438515) and in the essential oil of Thyme obtained by steam distillation (https://doi.org/10.1016/j.fitote.2007.11.004). It is also a volatile component of cannabis plant samples (PMID: 26657499). Isobornyl acetic acid Pichtosin C12H20O2 196.29 196.1463 (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate 125-12-2 CC(=O)O[C@H]1C[C@H]2CC[C@@]1(C)C2(C)C InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10+,12-/m1/s1 KGEKLUUHTZCSIP-JFGNBEQYSA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homopolycyclic compound Bicyclic monoterpenoid Bornane monoterpenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound logp 3.50 ALOGPS logs -3.51 ALOGPS logp 2.43 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate ChemAxon average_mass 196.29 ChemAxon mono_mass 196.1463 ChemAxon smiles CC(=O)O[C@H]1C[C@H]2CC[C@@]1(C)C2(C)C ChemAxon formula C12H20O2 ChemAxon inchi InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10+,12-/m1/s1 ChemAxon inchikey KGEKLUUHTZCSIP-JFGNBEQYSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 54.47 ChemAxon polarizability 11.03 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 247573 Buchbauer G, Jager W, Jirovetz L, Meyer F, Dietrich H: [Effects of valerian root oil, borneol, isoborneol, bornyl acetate and isobornyl acetate on the motility of laboratory animals (mice) after inhalation]. Pharmazie. 1992 Aug;47(8):620-2. 1438515 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:18 UTC 2020-07-24 23:30:08 UTC CDB000625 lsobutyrophenone Isobutyrophenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Isobutyrophenone is a colorless to pale yellow clear liquid. It is a very hydrophobic molecule, practically insoluble in water but readily soluble in organic solvents such as methanol, ethanol and ethyl acetate. It has also been detected as a volatile component of cannabis samples (PMID: 26657499). C10H12O 148.21 148.0888 2-methyl-1-phenylpropan-1-one 2-methyl-1-phenylpropan-1-one 611-70-1 CC(C)C(=O)C1=CC=CC=C1 InChI=1S/C10H12O/c1-8(2)10(11)9-6-4-3-5-7-9/h3-8H,1-2H3 BSMGLVDZZMBWQB-UHFFFAOYSA-N belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Alkyl-phenylketones Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aromatic homomonocyclic compounds Aryl alkyl ketones Benzoyl derivatives Hydrocarbon derivatives Organic oxides Phenylpropanes Alkyl-phenylketone Aromatic homomonocyclic compound Aryl alkyl ketone Benzenoid Benzoyl Hydrocarbon derivative Monocyclic benzene moiety Organic oxide Phenylpropane logp 2.54 ALOGPS logs -2.44 ALOGPS logp 2.77 ChemAxon pka_strongest_acidic 17.21 ChemAxon pka_strongest_basic -7.5 ChemAxon iupac 2-methyl-1-phenylpropan-1-one ChemAxon average_mass 148.21 ChemAxon mono_mass 148.0888 ChemAxon smiles CC(C)C(=O)C1=CC=CC=C1 ChemAxon formula C10H12O ChemAxon inchi InChI=1S/C10H12O/c1-8(2)10(11)9-6-4-3-5-7-9/h3-8H,1-2H3 ChemAxon inchikey BSMGLVDZZMBWQB-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 45.66 ChemAxon polarizability 16.98 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 69144 Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:20 UTC 2020-08-04 22:28:23 UTC CDB000626 Methyl isocyanate  Isocyanatomethane or methyl isocyanate, also known as iso-cyanatomethane or methyl carbonimide, belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOCN or its hydrocarbyl derivatives RN=C=O. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Isocyanatomethane is a colorless, poisonous, lachrymatory (tearing agent), flammable liquid. It is soluble in water, but it also reacts with it. Isocyanatomethane is an intermediate in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As a highly toxic and irritating material, it is extremely hazardous to human health. Cyanide is an inhibitor of the cytochrome C oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). As a result, the electron transport chain is disrupted, and the cell can no longer aerobically produce ATP for energy. Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Isocyanatomethane has been detected in the volatile fraction of Cannabis sativa samples, obtained from police seizures (PMID: 26657499). Iso-cyanatomethane Isocyanate de methyle Isocyanatomethane Methyl carbonimide Methyl isocyanide Methylcarbylamine MIC Isocyanic acid de methyle Methyl isocyanic acid Methylisocyanate C2H3NO 57.05 57.0215 isocyanatomethane methyl isocyanate 30108-95-3 CN=C=O InChI=1S/C2H3NO/c1-3-2-4/h1H3 HAMGRBXTJNITHG-UHFFFAOYSA-N belongs to the class of organic compounds known as isocyanates. These are organic compounds containing the isocyanic acid tautomer, HN=C=O, of cyanic acid, HOC#N or its hydrocarbyl derivatives RN=C=O. Isocyanates Organic compounds Organic nitrogen compounds Organonitrogen compounds Isocyanates Aliphatic acyclic compounds Hydrocarbon derivatives Imines Organic oxides Organooxygen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Hydrocarbon derivative Imine Isocyanate Organic 1,3-dipolar compound Organic oxide Organic oxygen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound isocyanates logp -0.24 ALOGPS logs -0.19 ALOGPS logp -0.043 ChemAxon pka_strongest_basic -5.1 ChemAxon iupac isocyanatomethane ChemAxon average_mass 57.05 ChemAxon mono_mass 57.0215 ChemAxon smiles CN=C=O ChemAxon formula C2H3NO ChemAxon inchi InChI=1S/C2H3NO/c1-3-2-4/h1H3 ChemAxon inchikey HAMGRBXTJNITHG-UHFFFAOYSA-N ChemAxon polar_surface_area 29.43 ChemAxon refractivity 13.34 ChemAxon polarizability 5.05 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 12228 59059 DB12765 Methyl isocyanate Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:26 UTC 2020-08-04 22:28:23 UTC CDB000627 lsodurene Isodurene or 1,2,3,5-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid, nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Isodurene is a tetramethylated derivative of benzene. Industrially, isodurene can be isolated from the reformed fraction of oil refineries. It may also be produced by methylation of toluene, xylenes and trimethylbenzenes (https://doi.org/10.1002/14356007.a13_227). Isodurene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene). Durene, isodurene and prehnitene have been found to only be slightly toxic on an acute toxicology basis and pose an acute health hazard only when ingested in excessive quantities (https://doi.org/10.3109/01480547809105016). Isodurene has been detected in the volatile fraction of Cannabis sativa samples, obtained from police seizures (PMID: 26657499). 1235-Tetramethylbenzene Isodurene C10H14 134.22 134.1096 1,2,3,5-tetramethylbenzene 1,2,3,5-tetramethylbenzene 527-53-7 CC1=CC(C)=C(C)C(C)=C1 InChI=1S/C10H14/c1-7-5-8(2)10(4)9(3)6-7/h5-6H,1-4H3 BFIMMTCNYPIMRN-UHFFFAOYSA-N belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Benzene and substituted derivatives Organic compounds Benzenoids Benzene and substituted derivatives Aromatic homomonocyclic compounds Aromatic hydrocarbons Unsaturated hydrocarbons Aromatic homomonocyclic compound Aromatic hydrocarbon Hydrocarbon Monocyclic benzene moiety Unsaturated hydrocarbon logp 4.06 ALOGPS logs -3.64 ALOGPS logp 4.03 ChemAxon iupac 1,2,3,5-tetramethylbenzene ChemAxon average_mass 134.22 ChemAxon mono_mass 134.1096 ChemAxon smiles CC1=CC(C)=C(C)C(C)=C1 ChemAxon formula C10H14 ChemAxon inchi InChI=1S/C10H14/c1-7-5-8(2)10(4)9(3)6-7/h5-6H,1-4H3 ChemAxon inchikey BFIMMTCNYPIMRN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.22 ChemAxon polarizability 17.15 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. 26657499 1.0 2020-03-19 00:47:29 UTC 2020-08-04 22:28:23 UTC CDB000628 lsoeugenol Isoeugenol is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It also known as propenylgualacol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as ‚ÄúFragrance‚Äù rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID: 10554062). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric. Isoeugenol is also a component of wood smoke and liquid smoke. It is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Isoeugenol (specifically the acetate ester) has also been used in the production of vanillin. Isoeugenol is one of several non-cannabinoid phenols found in cannabis plants (PMID: 6991645). (e)-2-Methoxy-4-(prop-1-enyl)phenol 2-Methoxy-4-[(1E)-1-propenyl]phenol 2-Methoxy-4-propenylphenol 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene 3-Methoxy-4-hydroxypropenylbenzene 4-Hydroxy-3-methoxy-1-propenylbenzene iso-Eugenol 2 Isoeugenol (I) Isoeugenol e Isoeugenol trans-form Propenylgualacol trans-2-Methoxy-4-(1-propenyl)phenol trans-2-Methoxy-4-propenylphenol trans-4-Propenylgualacol trans-P-Propenylquaiacol (e)-2-Methoxy-4- (1-propenyl)-phenol (e)-2-Methoxy-4-(1-propenyl)-phenol (e)-2-Methoxy-4-propenyl-phenol (E)-Isoeugenol 1-(3-Methoxy-4-hydroxyphenyl)-1-propane 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene 2-Methoxy-4-(1-propenyl)-phenol 2-Methoxy-4-(1-propenyl)phenol 2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0) 2-Methoxy-4-propenyl-phenol 2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene 4-Hydroxy-3-methoxypropenylbenzene trans-Isoeugenol Isoeugenol, (e)-isomer Isoeugenol 2-Methoxy-4-(prop-1-en-1-yl)phenol (E)-2-Methoxy-4-(1-propenyl)phenol (E)-2-Methoxy-4-(prop-1-en-1-yl)phenol 1-(3-Methoxy-4-hydroxyphenyl)-1-propene 2-Methoxy-4(E)-1-propenylphenol 2-Methoxy-4-(1-propen-1-yl)phenol 2-Methoxy-4-(1E)-1-propen-1-ylphenol 2-Methoxy-4-[(E)-1-propenyl]phenol 3-Methoxy-4-hydroxy-1-propenylbenzene 4-(1-Propenyl) Guaiacol 4-Hydroxy-3-methoxy-beta-methylstyrene 4-Hydroxy-3-methoxy-β-methylstyrene 4-Propenylguaiacol iso-Eugenol trans-4-Propenylguaiacol trans-p-Propenylguaiacol C10H12O2 164.2 164.0837 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol isoeugenol 5932-68-3 COC1=C(O)C=CC(\C=C\C)=C1 InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+ BJIOGJUNALELMI-ONEGZZNKSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyphenols Organic compounds Benzenoids Phenols Methoxyphenols Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Hydrocarbon derivatives Methoxybenzenes Phenoxy compounds Styrenes 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Styrene isoeugenol logp 3.04 GRIFFIN,S ET AL. (1999) melting_point -10 °C logp 2.79 ALOGPS logs -2.08 ALOGPS logp 2.64 ChemAxon pka_strongest_acidic 10.01 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol ChemAxon average_mass 164.2 ChemAxon mono_mass 164.0837 ChemAxon smiles COC1=C(O)C=CC(\C=C\C)=C1 ChemAxon formula C10H12O2 ChemAxon inchi InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+ ChemAxon inchikey BJIOGJUNALELMI-ONEGZZNKSA-N ChemAxon polar_surface_area 29.46 ChemAxon refractivity 49.86 ChemAxon polarizability 18.3 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 21106129 FDB012403 853433 C10469 50545 C00000620 ISOEUGENOL Isoeugenol Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. 6991645 White IR, Johansen JD, Arnau EG, Lepoittevin JP, Rastogi S, Bruze M, Andersen KE, Frosch PJ, Goossens A, Menne T: Isoeugenol is an important contact allergen: can it be safely replaced with isoeugenyl acetate? Contact Dermatitis. 1999 Nov;41(5):272-5. doi: 10.1111/j.1600-0536.1999.tb06160.x. 10554062 1.0 2020-03-19 00:47:34 UTC 2020-08-04 22:28:23 UTC CDB000629 lsoprene Isoprene, also known as 2-methyl-1,3-butadiene, belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. It is a common organic compound with the formula CH2=C(CH3)‚àíCH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber. C. G. Williams named the compound in 1860 after obtaining it from thermal decomposition (pyrolysis) of natural rubber. He correctly deduced the empirical formula C5H8 (https://doi.org/10.1098/rspl.1859.0101). Isoprene is produced and emitted by many species of trees (major prod