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CHEBI:10041 - withanolide D

ChEBI IDCHEBI:10041
ChEBI Namewithanolide D
Stars
DefinitionA withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4β,5β,6β,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity.
Secondary ChEBI IDCHEBI:66324
Last Modified28 October 2019
DownloadsMolfile
FormulaC28H38O6
Net Charge0
Average Mass470.606
Monoisotopic Mass470.26684
SMILES[H][C@@]12C[C@H]3O[C@]34[C@@H](O)C=CC(=O)[C@]4(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@@](C)(O)[C@@]1([H])CC(C)=C(C)C(=O)O1
InChIInChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28+/m0/s1
InChIKeySASUFNRGCZMRFD-JCUIILOWSA-N
Species of MetaboliteComponentSourceComments
Tubocapsicum anomalum (ncbitaxon:180580) - PubMed (17417907)
Withania somnifera (ncbitaxon:126910) leaf (BTO:0000713) DOI (10.1016/0031-9422(75)85035-7)
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
withanolide D (CHEBI:10041) has role antineoplastic agent (CHEBI:35610)
withanolide D (CHEBI:10041) is a 20-hydroxy steroid (CHEBI:36854)
withanolide D (CHEBI:10041) is a 4-hydroxy steroid (CHEBI:62846)
withanolide D (CHEBI:10041) is a enone (CHEBI:51689)
withanolide D (CHEBI:10041) is a epoxy steroid (CHEBI:145217)
withanolide D (CHEBI:10041) is a ergostanoid (CHEBI:50403)
withanolide D (CHEBI:10041) is a secondary alcohol (CHEBI:35681)
withanolide D (CHEBI:10041) is a tertiary alcohol (CHEBI:26878)
withanolide D (CHEBI:10041) is a withanolide (CHEBI:74716)
withanolide D (CHEBI:10041) is a δ-lactone (CHEBI:18946)
Incoming Relation(s)
17α-hydroxywithanolide D (CHEBI:66329) has functional parent withanolide D (CHEBI:10041)
IUPAC Name 
(4β,5β,6β,22R)-4,20-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Synonyms  Source
Withanolide DKEGG COMPOUND
4β,20α-dihydroxy-1-oxo-5β,6β-epoxy-20S,22R-witha-2,24-dienolideChEBI
Manual XrefsDatabases
C08842KEGG COMPOUND
C00003677KNApSAcK
Registry NumbersSources
Reaxys:5173298Reaxys
CAS:30655-48-2KEGG COMPOUND
CAS:30655-48-2ChemIDplus
Citations