(-)-cotinine (CHEBI:68641)

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ChEBI Name	(−)-cotinine

ChEBI ID	CHEBI:68641

ChEBI ASCII Name	(-)-cotinine

Definition	An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.

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

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Formula

C10H12N2O

Net Charge

Average Mass

176.21510

Monoisotopic Mass

176.09496

InChI

InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

InChIKey

UIKROCXWUNQSPJ-VIFPVBQESA-N

SMILES

[H][C@]1(CCC(=O)N1C)c1cccnc1

Metabolite of Species	Details
Nicotiana tabacum (NCBI:txid4097)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	biomarker A substance used as an indicator of a biological state. antidepressant Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.

ChEBI Ontology
Outgoing	(−)-cotinine (CHEBI:68641) has role antidepressant (CHEBI:35469) (−)-cotinine (CHEBI:68641) has role biomarker (CHEBI:59163) (−)-cotinine (CHEBI:68641) has role human xenobiotic metabolite (CHEBI:76967) (−)-cotinine (CHEBI:68641) has role plant metabolite (CHEBI:76924) (−)-cotinine (CHEBI:68641) is a N-alkylpyrrolidine (CHEBI:46775) (−)-cotinine (CHEBI:68641) is a pyridines (CHEBI:26421) (−)-cotinine (CHEBI:68641) is a pyrrolidin-2-ones (CHEBI:74223) (−)-cotinine (CHEBI:68641) is a pyrrolidine alkaloid (CHEBI:26456)

Incoming	trans-3-hydroxycotinine (CHEBI:71182) has functional parent (−)-cotinine (CHEBI:68641)

IUPAC Name

(5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one

Synonyms	Sources
(S)-(-)-Cotinine	ChemIDplus
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone	ChemIDplus
(S)-Cotinine	ChemIDplus
cotinine	ChEBI

Last Modified

22 February 2017