Showing Compound Card for Cannabigerovarinic acid (CDB000005)

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Record Information
Version1.0
Created at2020-03-19 00:34:51 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000005
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabigerovarinic acid
DescriptionCannabigerovarinic 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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC20H28O4
Average Molecular Weight332.44
Monoisotopic Molecular Weight332.1988
IUPAC Name3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid
Traditional Name3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-propylbenzoic acid
CAS Registry NumberNot Available
SMILES
CCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1C(O)=O
InChI Identifier
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+
InChI KeyFAVCTJGKHFHFHJ-GXDHUFHOSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Aromatic monoterpenoid
  • Hydroxybenzoic acid
  • Salicylic acid
  • Salicylic acid or derivatives
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Benzoic acid
  • Phenylpropane
  • Benzoyl
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.61ALOGPS
logP6.46ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity99.56 m³·mol⁻¹ChemAxon
Polarizability38.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCannabigerovarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerovarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerovarinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerovarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerovarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerovarinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerovarinic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound59444383
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. 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. [PubMed:30814733 ]
  2. 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. [PubMed:30718485 ]
  3. 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. [PubMed:19578847 ]
  4. 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. [PubMed:15240312 ]
  5. 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. [PubMed:29480337 ]