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CHEBI:67078 - Δ9-tetrahydrocannabinolic acid

ChEBI IDCHEBI:67078
ChEBI NameΔ9-tetrahydrocannabinolic acid
Stars
ASCII NameDelta(9)-tetrahydrocannabinolic acid
DefinitionA diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. A biosynthetic precursor to Δ9-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.
Last Modified23 August 2012
SubmitterSteve
DownloadsMolfile
FormulaC22H30O4
Net Charge0
Average Mass358.478
Monoisotopic Mass358.21441
SMILES[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)Oc1cc(CCCCC)c(C(=O)O)c(O)c12
InChIInChI=1S/C22H30O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h11-12,15-16,23H,5-10H2,1-4H3,(H,24,25)/t15-,16-/m1/s1
InChIKeyUCONUSSAWGCZMV-HZPDHXFCSA-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.
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.
Applications:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
biomarker  A substance used as an indicator of a biological state.
ChEBI Ontology
Outgoing Relation(s)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) has role anti-inflammatory agent (CHEBI:67079)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) has role biomarker (CHEBI:59163)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) has role metabolite (CHEBI:25212)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) has role neuroprotective agent (CHEBI:63726)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) is a benzochromene (CHEBI:38920)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) is a diterpenoid (CHEBI:23849)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) is a hydroxy monocarboxylic acid (CHEBI:35868)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) is a phytocannabinoid (CHEBI:67196)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) is a polyketide (CHEBI:26188)
Δ9-tetrahydrocannabinolic acid (CHEBI:67078) is conjugate acid of Δ9-tetrahydrocannabinolate (CHEBI:66963)
Incoming Relation(s)
Δ9-tetrahydrocannabinolate (CHEBI:66963) is conjugate base of Δ9-tetrahydrocannabinolic acid (CHEBI:67078)
IUPAC Name 
(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carboxylic acid
Synonyms  Source
9-Carboxy-delta(9)-thcChemIDplus
delta(9)-Tetrahydrocannabinolic acidChemIDplus
9-Carboxy-thcChemIDplus
Manual XrefsDatabases
CPD-7169MetaCyc
Registry NumbersSources
Reaxys:1397267Reaxys
CAS:23978-85-0ChemIDplus
Citations