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Showing Compound cannabigerolate (FDB030712)

Record Information
Version1.0
Creation date2015-05-07 19:53:17 UTC
Update date2020-09-17 15:29:34 UTC
Primary IDFDB030712
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecannabigerolate
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).
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-(3,7-Dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoateGenerator
Cannabigerolic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
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
Chemical FormulaC22H32O4
IUPAC name3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid
InChI IdentifierInChI=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
Isomeric SMILESCCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O
Average Molecular Weight360.494
Monoisotopic Molecular Weight360.23005951
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MScannabigerolate, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabigerolate, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabigerolate, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabigerolate, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabigerolate, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabigerolate, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MScannabigerolate, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xu-0119000000-b8e5c06544056dd55091Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05to-6957000000-cb8ac2f7deabc706cd56Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-9330000000-c7e7b332c6c5845bc49bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aor-0009000000-f612500589c166d6bd84Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0119000000-9843f3bdf4bed8e477cfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-1974000000-f64241ac053166d0e6daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2029000000-15e29defeb1cc4528edcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-9183000000-626fa32d60f248181dfdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-ca31895d0fab30e1ae60Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0009000000-1d04fad9fcf034954bb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0119000000-a0af8bbe8d2db5c09ac5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a71-1491000000-78b3b6f8d3f55214d92dSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference