CHEBI:9260 - 15α-stemmadenine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 15α-stemmadenine
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
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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
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.
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 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)
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
CPD-21546 MetaCyc
Stemmadenine Wikipedia
View more database links
Registry Numbers Types Sources
10012-73-4 CAS Registry Number KEGG COMPOUND
10012-73-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
28006917 PubMed citation Europe PMC
29511102 PubMed citation Europe PMC
3373227 PubMed citation Europe PMC
4021514 PubMed citation Europe PMC
5812148 PubMed citation Europe PMC
IND43628567 Agricola citation Europe PMC
Last Modified
11 December 2018
General Comment
2018-11-27 A separate entry exists for the 15β stereoisomer (please see CHEBI: 142656).