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CHEBI:63167 - raucaffrinoline

ChEBI IDCHEBI:63167
ChEBI Nameraucaffrinoline
Stars
DefinitionAn indole alkaloid having a ajmalan-type skeleton and characterised by a 17α-acetoxy group, a 21β-methyl group, loss of the 1-methyl group with associated unsaturation at N(1)=C(2), and a 20α-hydroxymethyl group in place of the 20β-ethyl side-chain.
Last Modified5 December 2011
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC21H24N2O3
Net Charge0
Average Mass352.434
Monoisotopic Mass352.17869
SMILES[H][C@@]12C[C@@H]3C4[C@@H](OC(C)=O)[C@@]5(C[C@@H]4N1[C@@H](C)[C@@H]3CO)C2=Nc1ccccc15
InChIInChI=1S/C21H24N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,10,12-13,16-18,20,24H,7-9H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1
InChIKeyXIMPCXFLDSKALH-FXRWJBKJSA-N
Roles Classification
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)
raucaffrinoline (CHEBI:63167) has parent hydride ajmalan (CHEBI:37673)
raucaffrinoline (CHEBI:63167) is a indole alkaloid (CHEBI:38958)
IUPAC Name 
(6S,8S,9R,10S,11aS,12aR)-9-(hydroxymethyl)-8-methyl-8,9,10,11,11a,12-hexahydro-6H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizin-13-yl acetate
Synonym  Source
(17R,20α,21β)-1,2-didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetateIUBMB
UniProt Name  Source
raucaffrinolineUniProt
Registry NumbersSources
Reaxys:7002801Reaxys
Reaxys:9294799Reaxys
Citations