ecgonine benzoate (CHEBI:41001)

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ChEBI Name	ecgonine benzoate

ChEBI ID	CHEBI:41001

Definition	A benzoate ester metabolite of cocaine formed by hydrolysis of the methyl ester group, catalysed by carboxylesterases.

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

Secondary ChEBI IDs	CHEBI:3041

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Formula

C16H19NO4

Net Charge

Average Mass

289.32640

Monoisotopic Mass

289.13141

InChI

InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1

InChIKey

GVGYEFKIHJTNQZ-RFQIPJPRSA-N

SMILES

[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)c1ccccc1)C(O)=O)N2C

Roles Classification
Biological Role(s):	marine xenobiotic metabolite Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. human xenobiotic metabolite Any human metabolite produced by metabolism of a xenobiotic compound in humans. epitope The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

ChEBI Ontology
Outgoing	ecgonine benzoate (CHEBI:41001) has functional parent ecgonine (CHEBI:4743) ecgonine benzoate (CHEBI:41001) has role epitope (CHEBI:53000) ecgonine benzoate (CHEBI:41001) has role human xenobiotic metabolite (CHEBI:76967) ecgonine benzoate (CHEBI:41001) has role marine xenobiotic metabolite (CHEBI:83399) ecgonine benzoate (CHEBI:41001) has role plant metabolite (CHEBI:76924) ecgonine benzoate (CHEBI:41001) is a benzoate ester (CHEBI:36054) ecgonine benzoate (CHEBI:41001) is a tropane alkaloid (CHEBI:37332)

IUPAC Name

(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Synonyms	Sources
(-)-benzoylecgonine	DrugBank
(1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid	PDBeChem
3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	NIST Chemistry WebBook
BCG	DrugBank
BEG	DrugBank
Benzoylecgonine	ChemIDplus
O-Benzoyl-(-)-ecgonine	NIST Chemistry WebBook
O-benzoylecgonine	ChemIDplus

Last Modified

19 November 2014