CHEBI:67078 - Δ9-tetrahydrocannabinolic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name Δ9-tetrahydrocannabinolic acid
ChEBI ID CHEBI:67078
ChEBI ASCII Name Delta(9)-tetrahydrocannabinolic acid
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB6705020, eMolecules:518145, eMolecules:883971, ZINC000006661227
Download Molfile XML SDF
Formula C22H30O4
Net Charge 0
Average Mass 358.47120
Monoisotopic Mass 358.21441
InChI InChI=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
InChIKey UCONUSSAWGCZMV-HZPDHXFCSA-N
SMILES [H][C@@]12CCC(C)=C[C@@]1([H])c1c(O)c(C(O)=O)c(CCCCC)cc1OC2(C)C
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 )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
9-Carboxy-delta(9)-thc ChemIDplus
9-Carboxy-thc ChemIDplus
delta(9)-Tetrahydrocannabinolic acid ChemIDplus
Manual Xref Database
CPD-7169 MetaCyc
View more database links
Registry Numbers Types Sources
1397267 Reaxys Registry Number Reaxys
23978-85-0 CAS Registry Number ChemIDplus
Citations Types Sources
15190053 PubMed citation Europe PMC
16511162 PubMed citation Europe PMC
Last Modified
23 August 2012