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CHEBI:9119 - serpentine

ChEBI IDCHEBI:9119
ChEBI Nameserpentine
Stars
DefinitionAn indole alkaloid that is 18-oxayohimban dehydrogenated at positions 3, 4, 5, 6, 16 and 17 and substituted by a methyl group at the 19α position and by a methoxycarbonyl group at position 16.
Last Modified7 January 2019
DownloadsMolfile
FormulaC21H20N2O3
Net Charge0
Average Mass348.402
Monoisotopic Mass348.14739
SMILES[H][C@]12Cc3c4[n-]c5ccccc5c4cc[n+]3C[C@]1([H])[C@H](C)OC=C2C(=O)OC
InChIInChI=1S/C21H20N2O3/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/h3-8,11-12,15-16H,9-10H2,1-2H3/t12-,15-,16+/m0/s1
InChIKeyWYTGDNHDOZPMIW-VBNZEHGJSA-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)
serpentine (CHEBI:9119) has parent hydride 18-oxayohimban (CHEBI:35638)
serpentine (CHEBI:9119) is a carboxylic ester (CHEBI:33308)
serpentine (CHEBI:9119) is a iminium betaine (CHEBI:35285)
serpentine (CHEBI:9119) is a indole alkaloid (CHEBI:38958)
serpentine (CHEBI:9119) is a quinolizines (CHEBI:38063)
serpentine (CHEBI:9119) is a zwitterion (CHEBI:27369)
serpentine (CHEBI:9119) is conjugate base of serpentine(1+) (CHEBI:142531)
Incoming Relation(s)
serpentine(1+) (CHEBI:142531) is conjugate acid of serpentine (CHEBI:9119)
IUPAC Name 
methyl (19α)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide-16-carboxylate
Synonyms  Source
SerpentineKEGG COMPOUND
Serpentine (alkaloid)KEGG COMPOUND
(19α)-3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyloxayohimbaniumChemIDplus
methyl (19α)-19-methyl-3,4,5,6,16,17-hexadehydrooxayohimban-4-ium-1-ide-16-carboxylateIUPAC
(4S,4aR,14aS)-4-methyl-1-[(methyloxy)carbonyl]-4a,5,14,14a-tetrahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizin-6-ium-13-ideIUPAC
Manual XrefsDatabases
C09241KEGG COMPOUND
C00001769KNApSAcK
Registry NumbersSources
Beilstein:5421116Beilstein
CAS:18786-24-8KEGG COMPOUND
CAS:18786-24-8ChemIDplus