Showing Compound Card for Cannabigerolic acid (CDB000018)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:34:37 UTC
Updated at2020-11-18 16:35:09 UTC
CannabisDB IDCDB000018
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCannabigerolic acid
DescriptionCannabigerolic 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 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(3,7-Dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoateGenerator
Cannabigerolic acidGenerator
Chemical FormulaC22H32O4
Average Molecular Weight360.49
Monoisotopic Molecular Weight360.2301
IUPAC Name3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid
Traditional Name3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid
CAS Registry Number25555-57-1
SMILES
CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O
InChI Identifier
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)
InChI KeySEEZIOZEUUMJME-UHFFFAOYSA-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
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Benzoic acid
  • Benzoyl
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • 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
logP5.31ALOGPS
logP7.35ChemAxon
logS-4.5ALOGPS
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 Count10ChemAxon
Refractivity108.77 m³·mol⁻¹ChemAxon
Polarizability42.63 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-MSCannabigerolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCannabigerolic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0009000000-f612500589c166d6bd842015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0119000000-9843f3bdf4bed8e477cf2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1974000000-f64241ac053166d0e6da2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0009000000-1d04fad9fcf034954bb12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0119000000-a0af8bbe8d2db5c09ac52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a71-1491000000-78b3b6f8d3f55214d92d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xu-0119000000-b8e5c06544056dd550912015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05to-6957000000-cb8ac2f7deabc706cd562015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-9330000000-c7e7b332c6c5845bc49b2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2029000000-15e29defeb1cc4528edc2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-9183000000-626fa32d60f248181dfd2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-ca31895d0fab30e1ae602021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.128 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.115 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.123 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.122 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.451 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.166 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0304284
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030712
KNApSAcK IDNot Available
Chemspider ID26459938
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3082240
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. 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. [PubMed:6991645 ]
  2. 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. [PubMed:28694184 ]