CHEBI:63167 - raucaffrinoline

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ChEBI Name raucaffrinoline
ChEBI ID CHEBI:63167
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H24N2O3
Net Charge 0
Average Mass 352.42690
Monoisotopic Mass 352.179
InChI InChI=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
InChIKey XIMPCXFLDSKALH-FXRWJBKJSA-N
SMILES [H][C@@]12C[C@H]3[C@@H](CO)[C@H](C)N1[C@H]1C[C@@]4([C@H](OC(C)=O)C31)c1ccccc1N=C24
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Synonyms Sources
(17R,20α,21β)-1,2-didehydro-1-demethyl-19-hydroxy-21-methyl-18-norajmalan-17-yl acetate IUBMB
raucaffrinoline UniProt
Registry Numbers Types Sources
7002801 Reaxys Registry Number Reaxys
9294799 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12031452 PubMed citation Europe PMC
12141861 PubMed citation Europe PMC
17142919 PubMed citation Europe PMC
19775092 PubMed citation Europe PMC
5020328 PubMed citation Europe PMC
Last Modified
05 December 2011