cytisine (CHEBI:4055)

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ChEBI Name	cytisine

ChEBI ID	CHEBI:4055

Definition	An organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking.

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

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Formula

C11H14N2O

Net Charge

Average Mass

190.24170

Monoisotopic Mass

190.11061

InChI

InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1

InChIKey

ANJTVLIZGCUXLD-DTWKUNHWSA-N

SMILES

O=c1cccc2[C@H]3CNC[C@H](C3)Cn12

Metabolite of Species	Details
Fabaceae (NCBI:txid3803)	See: PubMed
Laburnum anagyroides (NCBI:txid49828)	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. nicotinic acetylcholine receptor agonist An agonist that selectively binds to and activates a nicotinic acetylcholine receptor. phytotoxin Any toxin produced by a plant. 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):	nicotinic acetylcholine receptor agonist An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.

ChEBI Ontology
Outgoing	cytisine (CHEBI:4055) has role nicotinic acetylcholine receptor agonist (CHEBI:47958) cytisine (CHEBI:4055) has role phytotoxin (CHEBI:38231) cytisine (CHEBI:4055) has role plant metabolite (CHEBI:76924) cytisine (CHEBI:4055) is a alkaloid (CHEBI:22315) cytisine (CHEBI:4055) is a bridged compound (CHEBI:35990) cytisine (CHEBI:4055) is a lactam (CHEBI:24995) cytisine (CHEBI:4055) is a organic heterotricyclic compound (CHEBI:26979) cytisine (CHEBI:4055) is a secondary amino compound (CHEBI:50995)

IUPAC Name

(1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one

Last Modified

25 February 2016