CHEBI:17037 - geissoschizine

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ChEBI Name geissoschizine
ChEBI ID CHEBI:17037
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:5282, CHEBI:14292, CHEBI:24201
Supplier Information
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Formula C21H24N2O3
Net Charge 0
Average Mass 352.428
Monoisotopic Mass 352.17869
InChI InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,12,16,19,22,24H,8-11H2,1-2H3/b13-3-,17-12+/t16-,19-/m0/s1
InChIKey WKWHYFHGTWZCLM-PICGZERYSA-N
SMILES C=12[C@]3(N(C/C(/[C@H](C3)/C(=C\O)/C(=O)OC)=C/C)CCC1C4=CC=CC=C4N2)[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 )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing geissoschizine (CHEBI:17037) is a enol (CHEBI:33823)
geissoschizine (CHEBI:17037) is a indole alkaloid (CHEBI:38958)
geissoschizine (CHEBI:17037) is a methyl ester (CHEBI:25248)
geissoschizine (CHEBI:17037) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming 4,21-dehydrogeissoschizine (CHEBI:17294) has functional parent geissoschizine (CHEBI:17037)
IUPAC Name
methyl (16E,19E)-16-(hydroxymethylene)coryn-19-en-17-oate
Synonyms Sources
(16E,19E)-17-hydroxy-16-methoxycarbonyl-16,19-didehydro-corynane ChEBI
(19S)-geissoschizine UniProt
Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16E,19E)- ChemIDplus
Geissoschizine KEGG COMPOUND
Manual Xrefs Databases
C00051968 KNApSAcK
C02151 KEGG COMPOUND
GEISSOSCHIZINE MetaCyc
View more database links
Registry Numbers Types Sources
439-66-7 CAS Registry Number KEGG COMPOUND
439-66-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10822538 PubMed citation Europe PMC
28754932 PubMed citation Europe PMC
29575642 PubMed citation Europe PMC
29942076 PubMed citation Europe PMC
Last Modified
23 November 2018
General Comment
2018-11-21 Relevant articles: (1) Rapoport, H., Windgassen, R.J., Hughes, N.A. and Onak, T.P. (1959) The structure of geissoschizine. J. Am. Chem. Soc., 12, 3166-3167. (2) Takayama, H., Watanabe, T., Seki, H., Aimi, N. and Sakai, S. (1992) Geissoschizine revisited - definite proof of its stereostructure. Tetrahedron Letters, 33(45), 6831-6834.