1.0 2020-03-19 00:34:51 UTC 2020-11-18 16:35:09 UTC CDB000005 Cannabigerovarinic acid Cannabigerovarinic acid (CBGVA) is the C3 analogue of cannabigerolic acid (CBGA). CBGVA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabigerovarinic acid is a dihydroxybenzoic acid derived from divarinic acid on which the hydrogen at position 3 is substituted by a geranyl group. Cannabigerovarinic acid is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from divarinic 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, cannabigerovarinic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups substituting the benzene ring. Cannabigerovarinic acid is a key biosynthetic precursor of C3-cannabinoids. Cannabigerovarinic acid is an important cannabinoid found in cannabis and due to its biosynthetic relationship to other compounds efforts have been addressed to find alternative ways of producing it (in yeast; PMID: 30814733). A cell free system was developed to produces cannabinoids, including cannabigerovarinic acid, from glucose by supplying several enzymes that create isoprenylate derivatives and these prenylated cannabinoid intermediates (PMID: 30718485). The yeast and cell free systems produce these important natural products that are difficult to make or purify from living organisms. Cannabigerovarinate C20H28O4 332.44 332.1988 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O InChI=1S/C20H28O4/c1-5-7-15-12-17(21)16(19(22)18(15)20(23)24)11-10-14(4)9-6-8-13(2)3/h8,10,12,21-22H,5-7,9,11H2,1-4H3,(H,23,24)/b14-10+ FAVCTJGKHFHFHJ-GXDHUFHOSA-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 Monocyclic monoterpenoids Organic oxides Organooxygen compounds Phenylpropanes 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 Monocyclic monoterpenoid Monoterpenoid Organic oxide Organic oxygen compound Organooxygen compound Phenol Phenylpropane Resorcinol Salicylic acid Salicylic acid or derivatives Vinylogous acid logp 4.61 ALOGPS logs -4.27 ALOGPS logp 6.46 ChemAxon pka_strongest_acidic 2.92 ChemAxon pka_strongest_basic -5.8 ChemAxon iupac 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid ChemAxon average_mass 332.44 ChemAxon mono_mass 332.1988 ChemAxon smiles CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O ChemAxon formula C20H28O4 ChemAxon inchi InChI=1S/C20H28O4/c1-5-7-15-12-17(21)16(19(22)18(15)20(23)24)11-10-14(4)9-6-8-13(2)3/h8,10,12,21-22H,5-7,9,11H2,1-4H3,(H,23,24)/b14-10+ ChemAxon inchikey FAVCTJGKHFHFHJ-GXDHUFHOSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 99.56 ChemAxon polarizability 38.37 ChemAxon rotatable_bond_count 8 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 68003859 59444383 Luo X, Reiter MA, d'Espaux L, Wong J, Denby CM, Lechner A, Zhang Y, Grzybowski AT, Harth S, Lin W, Lee H, Yu C, Shin J, Deng K, Benites VT, Wang G, Baidoo EEK, Chen Y, Dev I, Petzold CJ, Keasling JD: Complete biosynthesis of cannabinoids and their unnatural analogues in yeast. Nature. 2019 Mar;567(7746):123-126. doi: 10.1038/s41586-019-0978-9. Epub 2019 Feb 27. 30814733 Valliere MA, Korman TP, Woodall NB, Khitrov GA, Taylor RE, Baker D, Bowie JU: A cell-free platform for the prenylation of natural products and application to cannabinoid production. Nat Commun. 2019 Feb 4;10(1):565. doi: 10.1038/s41467-019-08448-y. 30718485 Song SH, Vieille C: Recent advances in the biological production of mannitol. Appl Microbiol Biotechnol. 2009 Aug;84(1):55-62. doi: 10.1007/s00253-009-2086-5. Epub 2009 Jul 4. 19578847 Wisselink HW, Mars AE, van der Meer P, Eggink G, Hugenholtz J: Metabolic engineering of mannitol production in Lactococcus lactis: influence of overexpression of mannitol 1-phosphate dehydrogenase in different genetic backgrounds. Appl Environ Microbiol. 2004 Jul;70(7):4286-92. doi: 10.1128/AEM.70.7.4286-4292.2004. 15240312 Zhang M, Gu L, Cheng C, Ma J, Xin F, Liu J, Wu H, Jiang M: Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies. World J Microbiol Biotechnol. 2018 Feb 26;34(3):41. doi: 10.1007/s11274-018-2425-8. 29480337