CHEBI:4055 - cytisine

ChEBI IDCHEBI:4055
ChEBI Namecytisine
Stars
DefinitionAn 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.
Last Modified25 February 2016
DownloadsMolfile
FormulaC11H14N2O
Net Charge0
Average Mass190.246
Monoisotopic Mass190.11061
SMILESO=c1cccc2n1C[C@@H]1CNC[C@H]2C1
InChIInChI=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
InChIKeyANJTVLIZGCUXLD-DTWKUNHWSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Fabaceae (ncbitaxon:3803) - PubMed (22978215)
Laburnum anagyroides (ncbitaxon:49828) - PubMed (23022271)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
nicotinic acetylcholine receptor agonist  An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
phytotoxin  Any toxin produced by a plant.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
nicotinic acetylcholine receptor agonist  An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
ChEBI Ontology
Outgoing Relation(s)
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
Synonyms  Source
baptitoxinChemIDplus
baptitoxineChemIDplus
(−)-cytisineChEBI
laburninChemIDplus
sophorinChemIDplus
sophorineChemIDplus
Manual XrefsDatabases
C00002218KNApSAcK
C10763KEGG COMPOUND
C5EPDBeChem
CytisineWikipedia
D07770KEGG DRUG
LSM-25650LINCS
Registry NumbersSources
Reaxys:83882Reaxys
CAS:485-35-8NIST Chemistry WebBook
CAS:485-35-8ChemIDplus
CAS:485-35-8KEGG COMPOUND
Citations