1.0 2020-03-19 00:35:46 UTC 2020-11-18 16:35:09 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 57566924 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