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CHEBI:3469 - catharanthine

ChEBI IDCHEBI:3469
ChEBI Namecatharanthine
Stars
DefinitionAn organic heteropentacyclic compound and monoterpenoid indole alkaloid produced by the medicinal plant Catharanthus roseus via strictosidine.
Last Modified6 March 2020
DownloadsMolfile
FormulaC21H24N2O2
Net Charge0
Average Mass336.435
Monoisotopic Mass336.18378
SMILES[H][C@]12C=C(CC)[C@@]3([H])N(CCc4c(nc5ccccc45)[C@@]3(C(=O)OC)C1)C2
InChIInChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1
InChIKeyCMKFQVZJOWHHDV-NQZBTDCJSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Catharanthus roseus (ncbitaxon:4058) leaf (BTO:0000713) PubMed (17909486)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
catharanthine (CHEBI:3469) is a alkaloid ester (CHEBI:38481)
catharanthine (CHEBI:3469) is a bridged compound (CHEBI:35990)
catharanthine (CHEBI:3469) is a methyl ester (CHEBI:25248)
catharanthine (CHEBI:3469) is a monoterpenoid indole alkaloid (CHEBI:65323)
catharanthine (CHEBI:3469) is a organic heteropentacyclic compound (CHEBI:38164)
catharanthine (CHEBI:3469) is a tertiary amino compound (CHEBI:50996)
catharanthine (CHEBI:3469) is conjugate base of catharanthine(1+) (CHEBI:142675)
Incoming Relation(s)
catharanthine(1+) (CHEBI:142675) is conjugate acid of catharanthine (CHEBI:3469)
IUPAC Name 
methyl (2α,18β)-3,4-didehydroibogamine-18-carboxylate
Manual XrefsDatabases
C00001704KNApSAcK
C09107KEGG COMPOUND
CatharanthineWikipedia
CPD-7859MetaCyc
Registry NumbersSources
CAS:2468-21-5KEGG COMPOUND
Citations