1.0 2020-03-19 00:34:37 UTC 2020-11-18 16:35:09 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). 3-(3,7-Dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoate 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 26459938 FDB030712 3082240 Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis 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