CHEBI:63168 - perakine

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ChEBI Name perakine
ChEBI ID CHEBI:63168
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-formyl 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 C21H22N2O3
Net Charge 0
Average Mass 350.41100
Monoisotopic Mass 350.163
InChI InChI=1S/C21H22N2O3/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/h3-6,9-10,12-13,16-18,20H,7-8H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1
InChIKey GDXJMOGWONJRHL-FXRWJBKJSA-N
SMILES [H][C@@]12C[C@H]3[C@@H](C=O)[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 perakine (CHEBI:63168) has parent hydride ajmalan (CHEBI:37673)
perakine (CHEBI:63168) is a indole alkaloid (CHEBI:38958)
IUPAC Name
(6S,8S,9R,10R,11aS,12aR)-9-formyl-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-17-(acetyloxy)-21-methyl-18-norajmalan-19-al IUBMB
perakine UniProt
raucaffrine IUBMB
Registry Numbers Types Sources
11003614 Reaxys Registry Number Reaxys
4382-56-3 CAS Registry Number ChemIDplus
6491402 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12141861 PubMed citation Europe PMC
17142919 PubMed citation Europe PMC
18409028 PubMed citation Europe PMC
19775092 PubMed citation Europe PMC
5020328 PubMed citation Europe PMC
Last Modified
05 December 2011