CHEBI:9119 - serpentine

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ChEBI Name serpentine
ChEBI ID CHEBI:9119
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formulae C21H20N2O3
C21H20N2O3
Net Charge 0
Average Mass 348.396
Monoisotopic Mass 348.14739
InChI InChI=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
InChIKey WYTGDNHDOZPMIW-VBNZEHGJSA-N
SMILES [C@]12([C@@H](OC=C([C@]1(CC=3[N+](C2)=CC=C4C5=CC=CC=C5[N-]C34)[H])C(=O)OC)C)[H]
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 )
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ChEBI Ontology
Outgoing 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 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 Sources
(19α)-3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyloxayohimbanium ChemIDplus
(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-ide IUPAC
methyl (19α)-19-methyl-3,4,5,6,16,17-hexadehydrooxayohimban-4-ium-1-ide-16-carboxylate IUPAC
Serpentine KEGG COMPOUND
Serpentine (alkaloid) KEGG COMPOUND
Manual Xrefs Databases
C00001769 KNApSAcK
C09241 KEGG COMPOUND
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Registry Numbers Types Sources
18786-24-8 CAS Registry Number KEGG COMPOUND
18786-24-8 CAS Registry Number ChemIDplus
5421116 Beilstein Registry Number Beilstein
Last Modified
07 January 2019
General Comments
2007-09-20 Should not be confused with serpentine minerals (CHEBI:46670).
2011-07-20 Serpentine (alkaloid) is obtained from the roots of Rauvolfia serpentina.