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CHEBI:3472 - cathenamine

ChEBI IDCHEBI:3472
ChEBI Namecathenamine
Stars
DefinitionA yohimban alkaloid with formula C21H22N2O3, produced by Catharanthus roseus and Rauvolfia serpentina plant species.
Last Modified7 July 2022
DownloadsMolfile
FormulaC21H22N2O3
Net Charge0
Average Mass350.418
Monoisotopic Mass350.16304
SMILES[H][C@]12C[C@@]3([H])c4nc5ccccc5c4CCN3C=C1[C@H](C)OC=C2C(=O)OC
InChIInChI=1S/C21H22N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,10-12,15,19,22H,7-9H2,1-2H3/t12-,15-,19-/m0/s1
InChIKeyBXTHVTLKWJZGAA-ODYMNIRHSA-N
Species of MetaboliteComponentSourceComments
Rauvolfia serpentina (ncbitaxon:4060) - PubMed (11985599)
Catharanthus roseus (ncbitaxon:4058) cell suspension culture (BTO:0000221) DOI (10.1039/C39770000164)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
cathenamine (CHEBI:3472) has role plant metabolite (CHEBI:76924)
cathenamine (CHEBI:3472) is a methyl ester (CHEBI:25248)
cathenamine (CHEBI:3472) is a organic heteropentacyclic compound (CHEBI:38164)
cathenamine (CHEBI:3472) is a yohimban alkaloid (CHEBI:27358)
IUPAC Name 
methyl 19α-methyl-16,17,20,21-tetradehydro-18-oxayohimban-16-carboxylate
Synonyms  Source
(−)-cathenamineChEBI
20,21-didehydroajmalicineChEBI
16,17,20,21-tetradehydro-19α-methyl-18-oxayohimban-16-carboxylic acid methyl esterChEBI
UniProt Name  Source
cathenamineUniProt
Manual XrefsDatabases
C11680KEGG COMPOUND
C00051784KNApSAcK
CPD-21552MetaCyc
Registry NumbersSources
CAS:63661-74-5KEGG COMPOUND
Citations