CHEBI:142656 - 15β-stemmadenine

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ChEBI Name 15β-stemmadenine
ChEBI ID CHEBI:142656
ChEBI ASCII Name 15beta-stemmadenine
Definition A monoterpenoid indole alkaloid with forumula C21H26N2O3, isolated from the fruits of Tabernaemontana heyneana.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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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+/m1/s1
InChIKey MBXJCHZRHROMQA-YVDMJPQFSA-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
Tabernaemontana heyneana (IPNI:82149-1) Found in fruit (BTO:0000486). See: Grover, R.K., Srivastva, S., Kulshreshtha, D.K. and Roy, R. (2002) A new stereoisomer of stemmadenine alkaloid from Tabernaemontana heyneana. Magnetic Resonance in Chemistry, 40, 474-476.
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 15β-stemmadenine (CHEBI:142656) has role plant metabolite (CHEBI:76924)
15β-stemmadenine (CHEBI:142656) is a methyl ester (CHEBI:25248)
15β-stemmadenine (CHEBI:142656) is a monoterpenoid indole alkaloid (CHEBI:65323)
15β-stemmadenine (CHEBI:142656) is a organic heterotetracyclic compound (CHEBI:38163)
15β-stemmadenine (CHEBI:142656) is a primary alcohol (CHEBI:15734)
IUPAC Name
methyl (5E,6R,7S)-5-ethylidene-7-(hydroxymethyl)-1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole-7-carboxylate
Synonyms Sources
15-β-stemmadenine ChEBI
15β-stemmadenine ChEBI
Last Modified
27 November 2018
General Comment
2018-11-27 Relevant Article: Grover, R.K., Srivastva, S., Kulshreshtha, D.K. and Roy, R. (2002) A new stereoisomer of stemmadenine alkaloid from Tabernaemontana heyneana. Magnetic Resonance in Chemistry, 40, 474-476.