CHEBI:67081 - cannabigerolic acid

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ChEBI Name cannabigerolic acid
Definition A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Δ9-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C22H32O4
Net Charge 0
Average Mass 360.48710
Monoisotopic Mass 360.23006
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)/b16-12+
SMILES CCCCCc1cc(O)c(C\C=C(/C)CCC=C(C)C)c(O)c1C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via phytocannabinoid )
cannabinoid receptor agonist
An agonist that binds to and activates cannabinoid receptors.
(via cannabinoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cannabigerolic acid (CHEBI:67081) has functional parent olivetolic acid (CHEBI:66955)
cannabigerolic acid (CHEBI:67081) is a dihydroxybenzoic acid (CHEBI:23778)
cannabigerolic acid (CHEBI:67081) is a diterpenoid (CHEBI:23849)
cannabigerolic acid (CHEBI:67081) is a phytocannabinoid (CHEBI:67196)
cannabigerolic acid (CHEBI:67081) is a polyketide (CHEBI:26188)
cannabigerolic acid (CHEBI:67081) is a resorcinols (CHEBI:33572)
cannabigerolic acid (CHEBI:67081) is conjugate acid of cannabigerolate (CHEBI:66962)
Incoming cannabigerolate (CHEBI:66962) is conjugate base of cannabigerolic acid (CHEBI:67081)
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
Synonym Source
(E)-3-(3,7-Dimethyl-2,6-octadienyl)-2,4-dihydroxy-6-pentylbenzoic acid ChemIDplus
Manual Xrefs Databases
CPD-7166 MetaCyc
GB2456183 Patent
GB2468828 Patent
US2011021617 Patent
US2011038958 Patent
WO2009087351 Patent
WO2011017798 Patent
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Registry Numbers Types Sources
25555-57-1 CAS Registry Number ChemIDplus
2820770 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18283614 PubMed citation Europe PMC
18303850 PubMed citation Europe PMC
19704450 PubMed citation Europe PMC
21532172 PubMed citation Europe PMC
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22495534 PubMed citation Europe PMC
22766313 PubMed citation Europe PMC
22802619 PubMed citation Europe PMC
8663284 PubMed citation Europe PMC
9607329 PubMed citation Europe PMC
9862135 PubMed citation Europe PMC
Last Modified
06 August 2014