1.0 2020-03-18 23:23:59 UTC 2020-12-07 19:07:04 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 75693449 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