11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (CHEBI:77273)

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ChEBI Name	11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol

ChEBI ID	CHEBI:77273

ChEBI ASCII Name	11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol

Definition	A phytocannabinoid that is Δ⁹-tetrahydrocannabinol in which the C-11 methyl has been fully oxidised to a carboxy group. Further enzymatic oxidation product of 11-hydroxy-Δ⁹-tetrahydrocannabinol.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	eMolecules:976824, ZINC000001996369

Download	Molfile XML SDF

Wikipedia	License
Citraconic acid is an organic compound with the formula CH3C2H(CO2H)2. It is a white solid. The alkene is cis. The related trans alkene is called mesaconic acid. It is one of the pyrocitric acids formed upon the heating of citric acid. Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature. In the laboratory, citraconic acid can be produced by thermal isomerization of itaconic acid anhydride to give citraconic anhydride, which can be hydrolyzed to citraconic acid. The required itaconic acid anhydride is obtained by dry distillation of citric acid.
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Formula

C21H28O4

Net Charge

Average Mass

344.44460

Monoisotopic Mass

344.19876

InChI

InChI=1S/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h10-12,15-16,22H,4-9H2,1-3H3,(H,23,24)/t15-,16-/m1/s1

InChIKey

YOVRGSHRZRJTLZ-HZPDHXFCSA-N

SMILES

CCCCCc1cc(O)c2[C@@H]3C=C(CC[C@H]3C(C)(C)Oc2c1)C(O)=O

Roles Classification
Biological Role(s):	human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. 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 )

ChEBI Ontology
Outgoing	11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol (CHEBI:77273) has functional parent Δ⁹-tetrahydrocannabinol (CHEBI:66964) 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol (CHEBI:77273) has role human xenobiotic metabolite (CHEBI:76967) 11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol (CHEBI:77273) is a phytocannabinoid (CHEBI:67196)

IUPAC Name

(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid

Synonyms	Sources
(6aR,10aR)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic acid	ChEBI
11-COOH-THC	ChEBI
11-nor-9-carboxy-delta-9-tetrahydrocannabinol	ChEBI
11-nor-9-carboxy-THC	ChEBI
THC-11-oic acid	ChEBI
THC-COOH	ChEBI

Last Modified

07 February 2014