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CHEBI:67081 - cannabigerolic acid

ChEBI IDCHEBI:67081
ChEBI Namecannabigerolic acid
Stars
DefinitionA 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.
Last Modified6 August 2014
SubmitterSteve
DownloadsMolfile
FormulaC22H32O4
Net Charge0
Average Mass360.494
Monoisotopic Mass360.23006
SMILESCCCCCc1cc(O)c(C/C=C(\C)CCC=C(C)C)c(O)c1C(=O)O
InChIInChI=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+
InChIKeySEEZIOZEUUMJME-FOWTUZBSSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
cannabinoid receptor agonist  An agonist that binds to and activates cannabinoid receptors.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
cannabigerolate (CHEBI:66962) is conjugate base of cannabigerolic acid (CHEBI:67081)
IUPAC Name 
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 acidChemIDplus
Manual XrefsDatabases
CPD-7166MetaCyc
US2011021617Patent
WO2011017798Patent
US2011038958Patent
GB2468828Patent
WO2009087351Patent
GB2456183Patent
Registry NumbersSources
Reaxys:2820770Reaxys
CAS:25555-57-1ChemIDplus
Citations