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CHEBI:9260 - 15α-stemmadenine

ChEBI IDCHEBI:9260
ChEBI Name15α-stemmadenine
Stars
ASCII Name15alpha-stemmadenine
DefinitionA monoterpenoid indole alkaloid with formula C21H26N2O3, isolated from several plant species including Rhazya stricta , Tabernaemontana dichotoma and Aspidosperma pyricollum.
Last Modified11 December 2018
DownloadsMolfile
FormulaC21H26N2O3
Net Charge0
Average Mass354.450
Monoisotopic Mass354.19434
SMILES[H][C@@]12CCN(CCc3c(nc4ccccc34)[C@@]1(CO)C(=O)OC)C/C2=C/C
InChIInChI=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
InChIKeyMBXJCHZRHROMQA-OSZHWHEXSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Rhazya stricta (ncbitaxon:396313) leaf (BTO:0000713) PubMed (3373227)
Tabernaemontana dichotoma (IPNI:82089-1) seed (PO:0009010) PubMed (4021514)
Aspidosperma pyricollum (IPNI:22033-2) - Article (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.)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
stemmadeninChemIDplus
(+)-stemmadenineChemIDplus
15-α-stemmadenineChEBI
15α-stemmadenineChEBI
Manual XrefsDatabases
C11691KEGG COMPOUND
C00026041KNApSAcK
StemmadenineWikipedia
CPD-21546MetaCyc
Registry NumbersSources
CAS:10012-73-4KEGG COMPOUND
CAS:10012-73-4ChemIDplus
Citations