CHEBI:9260 - 15α-stemmadenine

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ChEBI Name 15α-stemmadenine
ChEBI ID CHEBI:9260
ChEBI ASCII Name 15alpha-stemmadenine
Definition A monoterpenoid indole alkaloid with formula C21H26N2O3, isolated from several plant species including Rhazya stricta, Tabernaemontana dichotoma and Aspidosperma pyricollum.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000030727473
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Formula C21H26N2O3
Net Charge 0
Average Mass 354.444
Monoisotopic Mass 354.19434
InChI InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21-/m0/s1
InChIKey MBXJCHZRHROMQA-OSZHWHEXSA-N
SMILES C12=C(C=CC=C1)NC=3[C@]([C@@]4(/C(/CN(CC4)CCC32)=C\C)[H])(C(=O)OC)CO
Metabolite of Species Details
Aspidosperma pyricollum (IPNI:22033-2) See: Carmo, H.M., Filho, R.B. and Vieiro, I.J.C. (2015) A novel alkaloid from Aspidoserma pyricollum (Apocynaceae) and complete 1H and 13C chemical shift assignments. Helv. Chim. Acta, 98, 1381-1386.
Tabernaemontana dichotoma (IPNI:82089-1) Found in seed (PO:0009010). See: PubMed
Rhazya stricta (NCBI:txid396313) Found in leaf (BTO:0000713). See: PubMed
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 )
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ChEBI Ontology
Outgoing 15α-stemmadenine (CHEBI:9260) has role plant metabolite (CHEBI:76924)
15α-stemmadenine (CHEBI:9260) is a Aspidosperma alkaloid (CHEBI:142772)
15α-stemmadenine (CHEBI:9260) is a methyl ester (CHEBI:25248)
15α-stemmadenine (CHEBI:9260) is a monoterpenoid indole alkaloid (CHEBI:65323)
15α-stemmadenine (CHEBI:9260) is a organic heterotetracyclic compound (CHEBI:38163)
15α-stemmadenine (CHEBI:9260) is a primary alcohol (CHEBI:15734)
15α-stemmadenine (CHEBI:9260) is conjugate base of 15α-stemmadenine(1+) (CHEBI:142674)
Incoming 15α-stemmadenine(1+) (CHEBI:142674) is conjugate acid of 15α-stemmadenine (CHEBI:9260)
IUPAC Name
methyl (5E,6S,7S)-5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylate
Synonyms Sources
(+)-stemmadenine ChemIDplus
15-α-stemmadenine ChEBI
15α-stemmadenine ChEBI
stemmadenin ChemIDplus
Manual Xrefs Databases
C00026041 KNApSAcK
C11691 KEGG COMPOUND
CPD-21546 MetaCyc
Stemmadenine Wikipedia
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Registry Numbers Types Sources
10012-73-4 CAS Registry Number KEGG COMPOUND
10012-73-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
11 December 2018
General Comment
2018-11-27 A separate entry exists for the 15β stereoisomer (please see CHEBI: 142656).