Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-03-18 23:23:59 UTC |
---|
Updated at | 2020-12-07 19:07:04 UTC |
---|
CannabisDB ID | CDB000079 |
---|
Secondary Accession Numbers | Not Available |
---|
Cannabis Compound Identification |
---|
Common Name | Guaiol |
---|
Description | 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 ) |
---|
Structure | |
---|
Synonyms | Not Available |
---|
Chemical Formula | C15H26O |
---|
Average Molecular Weight | 222.37 |
---|
Monoisotopic Molecular Weight | 222.1984 |
---|
IUPAC Name | 2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol |
---|
Traditional Name | 2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol |
---|
CAS Registry Number | 489-86-1 |
---|
SMILES | C[C@H]1CCC2=C1C[C@H](CC[C@@H]2C)C(C)(C)O |
---|
InChI Identifier | 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 |
---|
InChI Key | TWVJWDMOZJXUID-SRVKXCTJSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Sesquiterpenoids |
---|
Direct Parent | Sesquiterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Sesquiterpenoid
- Tertiary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
|
---|
Molecular Framework | Aliphatic homopolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
|
Role | Industrial application: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 92 °C | Wikipedia | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | Not Available | Not Available |
|
---|
Predicted Properties | [] |
---|
Spectra |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | Guaiol, non-derivatized, GC-MS Spectrum | splash10-0btc-7900000000-8740930d4a3e89faacce | Spectrum | Predicted GC-MS | Guaiol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum |
|
---|
NMR | Not Available |
---|
Pathways |
---|
Pathways | Not Available |
---|
Protein Targets |
---|
Enzymes | Not Available |
---|
Transporters | Not Available |
---|
Metal Bindings | Not Available |
---|
Receptors | Not Available |
---|
Transcriptional Factors | Not Available |
---|
Concentrations Data |
---|
| |
8-Ball Kush | Detected and Quantified | 1.439 mg/g dry wt | | details | 9 Lb Hammer | Detected and Quantified | 0.100 mg/g dry wt | | details | 9 Lb Hammer | Detected and Quantified | 0.1 mg/g dry wt | | details | Adonis | Detected and Quantified | 0.081 mg/g dry wt | | details | Alien Sour Apple | Detected and Quantified | 0.079 mg/g dry wt | | details | Black Boss | Detected and Quantified | 0.573 mg/g dry wt | | details | Blue Dream | Detected and Quantified | 0.138 mg/g dry wt | | details | Blue Dream | Detected and Quantified | 0.154 mg/g dry wt | | details | Blue Dream | Detected and Quantified | 0.897 mg/g dry wt | | details | Blue Dream | Detected and Quantified | 0.917 mg/g dry wt | | details | Bob Marley | Detected and Quantified | 0.521 mg/g dry wt | | details | Chemdawg | Detected and Quantified | 0.099 mg/g dry wt | | details | Chemdawg #4 | Detected and Quantified | 0.080 mg/g dry wt | | details | Chemdawg #4 | Detected and Quantified | 0.100 mg/g dry wt | | details | Chemdawg #4 | Detected and Quantified | 0.08 mg/g dry wt | | details | Chemdawg #4 | Detected and Quantified | 0.1 mg/g dry wt | | details | Cookies and Cream | Detected and Quantified | 0.056 mg/g dry wt | | details | Dairy Queen | Detected and Quantified | 0.314 mg/g dry wt | | details | Dark Shadow Haze | Detected and Quantified | 0.116 mg/g dry wt | | details | FLO | Detected and Quantified | 0.054 mg/g dry wt | | details | Goji OG | Detected and Quantified | 0.753 mg/g dry wt | | details | Golden Cobra | Detected and Quantified | 0.218 mg/g dry wt | | details | Golden Sage | Detected and Quantified | 0.063 mg/g dry wt | | details | Gorilla Glue | Detected and Quantified | 0.143 mg/g dry wt | | details | Gorilla Glue #4 | Detected and Quantified | 0.093 mg/g dry wt | | details | Grape Stomper | Detected and Quantified | 0.075 mg/g dry wt | | details | Grizzly Kush | Detected and Quantified | 0.071 mg/g dry wt | | details | Hash Plant | Detected and Quantified | 0.660 mg/g dry wt | | details | Hash Plant | Detected and Quantified | 0.900 mg/g dry wt | | details | Hash Plant | Detected and Quantified | 0.66 mg/g dry wt | | details | Hash Plant | Detected and Quantified | 0.9 mg/g dry wt | | details | Hemlock | Detected and Quantified | 0.066 mg/g dry wt | | details | Jabberwocky | Detected and Quantified | 1.143 mg/g dry wt | | details | Jabberwocky | Detected and Quantified | 1.425 mg/g dry wt | | details | Jack Herer | Detected and Quantified | 0.569 mg/g dry wt | | details | Kandy Kush | Detected and Quantified | 0.143 mg/g dry wt | | details | Kush Puppy | Detected and Quantified | 0.662 mg/g dry wt | | details | La Choco | Detected and Quantified | 0.961 mg/g dry wt | | details | Lemon Balm | Detected and Quantified | 0.909 mg/g dry wt | | details | Lemon Goji | Detected and Quantified | 0.124 mg/g dry wt | | details | Lemon OG | Detected and Quantified | 0.099 mg/g dry wt | | details | Lemon Sherbet | Detected and Quantified | 0.629 mg/g dry wt | | details | Lemon Skunk | Detected and Quantified | 0.062 mg/g dry wt | | details | Lemon Skunk | Detected and Quantified | 0.189 mg/g dry wt | | details | Liberty Haze | Detected and Quantified | 0.164 mg/g dry wt | | details | Lohan | Detected and Quantified | 0.057 mg/g dry wt | | details | Lucky Charms | Detected and Quantified | 0.206 mg/g dry wt | | details | Maui Haze | Detected and Quantified | 0.089 mg/g dry wt | | details | Moby Dick | Detected and Quantified | 0.406 mg/g dry wt | | details | Moonshine Ghost Trane Haze | Detected and Quantified | 0.815 mg/g dry wt | | details | Nightmare Cookie | Detected and Quantified | 0.265 mg/g dry wt | | details | Orange Skunk | Detected and Quantified | 0.873 mg/g dry wt | | details | Pineapple Skunk | Detected and Quantified | 1.544 mg/g dry wt | | details | Pipe Dream | Detected and Quantified | 0.825 mg/g dry wt | | details | Platinum Delight | Detected and Quantified | 0.171 mg/g dry wt | | details | Purple Eclipse | Detected and Quantified | 0.206 mg/g dry wt | | details | Rocket Fuel | Detected and Quantified | 1.271 mg/g dry wt | | details | Rollex OG | Detected and Quantified | 0.177 mg/g dry wt | | details | Rosetta Stone | Detected and Quantified | 0.140 mg/g dry wt | | details | Rosetta Stone | Detected and Quantified | 0.14 mg/g dry wt | | details | Sensi Star | Detected and Quantified | 0.37 mg/g dry wt | | details | Sensi Star (Pure Indica) | Detected and Quantified | 0.30 +/- 0.01 mg/g dry wt | | details | Skunk Haze | Detected and Quantified | 0.246 mg/g dry wt | | details | Skywalker OG | Detected and Quantified | 1.184 mg/g dry wt | | details | Spectrum | Detected and Quantified | 0.915 mg/g dry wt | | details | Star Bud | Detected and Quantified | 0.063 mg/g dry wt | | details | Star Killer | Detected and Quantified | 0.141 mg/g dry wt | | details | Strawberry Fields | Detected and Quantified | 0.088 mg/g dry wt | | details | Strawberry Fields | Detected and Quantified | 0.108 mg/g dry wt | | details | Sunset Sherbet | Detected and Quantified | 0.130 mg/g dry wt | | details | Sunset Sherbet | Detected and Quantified | 0.190 mg/g dry wt | | details | Sunset Sherbet | Detected and Quantified | 0.13 mg/g dry wt | | details | Sunset Sherbet | Detected and Quantified | 0.19 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.140 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.56 mg/g dry wt | | details | Tangerine Dream | Detected and Quantified | 0.14 mg/g dry wt | | details | Tangerine Dream (Sativa dominant) | Detected and Quantified | 0.49 +/- 0.02 mg/g dry wt | | details | The Sauce | Detected and Quantified | 0.264 mg/g dry wt | | details | Venom OG | Detected and Quantified | 0.170 mg/g dry wt | | details | Venom OG | Detected and Quantified | 0.17 mg/g dry wt | | details | White Widow | Detected and Quantified | 0.805 mg/g dry wt | | details | Wonder Woman | Detected and Quantified | 0.644 mg/g dry wt | | details |
|
---|
External Links |
---|
HMDB ID | Not Available |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FoodDB ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | Not Available |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 92245464 |
---|
PDB ID | Not Available |
---|
ChEBI ID | Not Available |
---|
References |
---|
General References | - 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:29352826 ]
- Liu T, Wang CJ, Xie HQ, Mu Q: Guaiol--a naturally occurring insecticidal sesquiterpene. Nat Prod Commun. 2013 Oct;8(10):1353-4. [PubMed:24354171 ]
|
---|