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CHEBI:37665 - sarmentogenin

ChEBI IDCHEBI:37665
ChEBI Namesarmentogenin
Stars
DefinitionA member of the class of cardenolides that is 5β-card-20(22)-enolide which is substituted by hydroxy groups at the 3β, 11α, and 14β positions.
Last Modified19 March 2025
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC23H34O5
Net Charge0
Average Mass390.520
Monoisotopic Mass390.24062
SMILES[H][C@]12CC[C@@]3([H])[C@@]4(O)CC[C@H](C5=CC(=O)OC5)[C@@]4(C)C[C@@H](O)[C@]3([H])[C@@]1(C)CC[C@H](O)C2
InChIInChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-20(21)18(25)11-22(2)16(6-8-23(17,22)27)13-9-19(26)28-12-13/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18-,20-,21+,22-,23+/m1/s1
InChIKeyFLMSQRUGSHIKCT-DDZQJACLSA-N
Species of MetaboliteComponentSourceComments
Mallotus nudiflorus (ncbitaxon:300977) bark (BTO:0001301) DOI (10.1002/hlca.200590219) Found in stem bark
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
sarmentogenin (CHEBI:37665) has parent hydride 5β-cardanolide (CHEBI:35542)
sarmentogenin (CHEBI:37665) has role plant metabolite (CHEBI:76924)
sarmentogenin (CHEBI:37665) is a 11α-hydroxy steroid (CHEBI:19129)
sarmentogenin (CHEBI:37665) is a 14β-hydroxy steroid (CHEBI:36862)
sarmentogenin (CHEBI:37665) is a 3β-hydroxy steroid (CHEBI:36836)
sarmentogenin (CHEBI:37665) is a cardenolides (CHEBI:74634)
Incoming Relation(s)
divaricoside (CHEBI:4668) has functional parent sarmentogenin (CHEBI:37665)
rhodexin A (CHEBI:27481) has functional parent sarmentogenin (CHEBI:37665)
IUPAC Name 
3β,11α,14-trihydroxy-5β-card-20(22)-enolide
Synonym  Source
11-alpha-HydroxydigitoxigeninChemIDplus
Manual XrefsDatabases
LMST01120024LIPID MAPS
Registry NumbersSources
Reaxys:96477Reaxys
CAS:76-28-8ChemIDplus
Citations