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CHEBI:69120 - withaferin A

ChEBI IDCHEBI:69120
ChEBI Namewithaferin A
Stars
DefinitionA withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4β,5β,6β,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.
Secondary ChEBI IDCHEBI:10040
Last Modified29 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@H](C)[C@@]1([H])CC(C)=C(CO)C(=O)O1
InChIInChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
InChIKeyDBRXOUCRJQVYJQ-CKNDUULBSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Physalis longifolia (ncbitaxon:161495) aerial part (BTO:0001658) PubMed (22098611) CH2Cl2-MeOH(1:1) extract of the air-dried aerial parts
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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)
withaferin A (CHEBI:69120) has role antineoplastic agent (CHEBI:35610)
withaferin A (CHEBI:69120) has role apoptosis inducer (CHEBI:68495)
withaferin A (CHEBI:69120) is a 27-hydroxy steroid (CHEBI:37914)
withaferin A (CHEBI:69120) is a 4-hydroxy steroid (CHEBI:62846)
withaferin A (CHEBI:69120) is a enone (CHEBI:51689)
withaferin A (CHEBI:69120) is a epoxy steroid (CHEBI:145217)
withaferin A (CHEBI:69120) is a ergostanoid (CHEBI:50403)
withaferin A (CHEBI:69120) is a primary alcohol (CHEBI:15734)
withaferin A (CHEBI:69120) is a secondary alcohol (CHEBI:35681)
withaferin A (CHEBI:69120) is a withanolide (CHEBI:74716)
withaferin A (CHEBI:69120) is a δ-lactone (CHEBI:18946)
Incoming Relation(s)
2,3-dihydro-3β-O-sulfate withaferin A (CHEBI:69123) has functional parent withaferin A (CHEBI:69120)
2,3-dihydro-3β-methoxy withaferin A (CHEBI:69121) has functional parent withaferin A (CHEBI:69120)
2,3-dihydrowithaferin A (CHEBI:69124) has functional parent withaferin A (CHEBI:69120)
sitoindoside IX (CHEBI:69119) has functional parent withaferin A (CHEBI:69120)
withalongolide A (CHEBI:69106) has functional parent withaferin A (CHEBI:69120)
withalongolide B (CHEBI:69107) has functional parent withaferin A (CHEBI:69120)
withalongolide C (CHEBI:69108) has functional parent withaferin A (CHEBI:69120)
withalongolide G (CHEBI:69126) has functional parent withaferin A (CHEBI:69120)
withalongolide H (CHEBI:69112) has functional parent withaferin A (CHEBI:69120)
IUPAC Name 
(4β,5β,6β,22R)-4,27-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Synonyms  Source
Withaferin AKEGG COMPOUND
4β,27-dihydroxy-1-oxo-5β,6β-epoxywitha-2,24-dienolideChEBI
Manual XrefsDatabases
C08841KEGG COMPOUND
Withaferin_AWikipedia
WO2010030395Patent
WO2010053655Patent
C00003676KNApSAcK
Registry NumbersSources
Reaxys:6284722Reaxys
CAS:5119-48-2KEGG COMPOUND
CAS:5119-48-2ChemIDplus
Citations