1.0 2020-03-19 00:36:05 UTC 2020-11-18 16:35:10 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