CHEBI:69120 - withaferin A

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ChEBI Name withaferin A
ChEBI ID CHEBI:69120
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:10040
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Formula C28H38O6
Net Charge 0
Average Mass 470.59770
Monoisotopic Mass 470.267
InChI InChI=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
InChIKey DBRXOUCRJQVYJQ-CKNDUULBSA-N
SMILES C[C@@H]([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC(C)=C(CO)C(=O)O1
Metabolite of Species Details
Physalis longifolia (NCBI:txid161495) Found in aerial part (BTO:0001658). CH2Cl2-MeOH(1:1) extract of the air-dried aerial parts See: PubMed
Roles Classification
Biological Role(s): 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.
(via withanolide )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 δ-lactone (CHEBI:18946)
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 epoxide (CHEBI:32955)
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)
Incoming 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 Sources
4β,27-dihydroxy-1-oxo-5β,6β-epoxywitha-2,24-dienolide ChEBI
Withaferin A KEGG COMPOUND
Manual Xrefs Databases
C00003676 KNApSAcK
C08841 KEGG COMPOUND
Withaferin_A Wikipedia
WO2010030395 Patent
WO2010053655 Patent
View more database links
Registry Numbers Types Sources
5119-48-2 CAS Registry Number KEGG COMPOUND
5119-48-2 CAS Registry Number ChemIDplus
6284722 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22098611 PubMed citation Europe PMC
22935676 PubMed citation Europe PMC
22989414 PubMed citation Europe PMC
23107437 PubMed citation Europe PMC
23129310 PubMed citation Europe PMC
23318585 PubMed citation Europe PMC
23821767 PubMed citation Europe PMC
Last Modified
28 July 2014