CHEBI:17037 - (19E)-geissoschizine

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ChEBI Name (19E)-geissoschizine
ChEBI ID CHEBI:17037
ChEBI ASCII Name (19E)-geissoschizine
Definition An indole alkaloid with formula C21H24N2O3. It is a biosynthetic precursor for a variety of monoterpenoid indole alkaloids.
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 352.434
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-KGZWXYIYSA-N
SMILES [H][C@@]12C[C@H](\C(=C\O)C(=O)OC)\C(CN1CCC1=C2NC2=CC=CC=C12)=C/C
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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 (19E)-geissoschizine (CHEBI:17037) has role plant metabolite (CHEBI:76924)
(19E)-geissoschizine (CHEBI:17037) is a enol (CHEBI:33823)
(19E)-geissoschizine (CHEBI:17037) is a indole alkaloid (CHEBI:38958)
(19E)-geissoschizine (CHEBI:17037) is a methyl ester (CHEBI:25248)
(19E)-geissoschizine (CHEBI:17037) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming 4,21-dehydrogeissoschizine (CHEBI:17294) has functional parent (19E)-geissoschizine (CHEBI:17037)
IUPAC Name
methyl (16Z,19E)-17-hydroxycoryna-16,19-dien-16-carboxylate
Synonyms Sources
(+)-geissoschizine ChEBI
(16Z,19E)-17-hydroxy-16-methoxycarbonyl-16,19-didehydro-corynane ChEBI
(19E)-geissoschizine UniProt
19E-geissoschizine ChEBI
Corynan-16-carboxylic acid, 16,17,19,20-tetradehydro-17-hydroxy-, methyl ester, (16Z,19E)- ChEBI
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
12683825 PubMed citation Europe PMC
28467090 PubMed citation Europe PMC
28754932 PubMed citation Europe PMC
29147812 PubMed citation Europe PMC
29511102 PubMed citation Europe PMC
29575642 PubMed citation Europe PMC
29942076 PubMed citation Europe PMC
Last Modified
01 July 2022
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.