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CHEBI:69107 - withalongolide B

ChEBI IDCHEBI:69107
ChEBI Namewithalongolide B
Stars
DefinitionA withanolide that is 27-deoxywithaferin A substituted by a hydroxy group at position 19. Isolated from Physalis longifolia, it exhibits antineoplastic activity.
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(CO)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@H](C)[C@@]1([H])CC(C)=C(C)C(=O)O1
InChIInChI=1S/C28H38O6/c1-14-11-21(33-25(32)15(14)2)16(3)18-5-6-19-17-12-24-28(34-24)23(31)8-7-22(30)27(28,13-29)20(17)9-10-26(18,19)4/h7-8,16-21,23-24,29,31H,5-6,9-13H2,1-4H3/t16-,17-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
InChIKeyOZBFGYQTKGOIKC-NSYRIIBJSA-N
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 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)
withalongolide B (CHEBI:69107) has functional parent withaferin A (CHEBI:69120)
withalongolide B (CHEBI:69107) has role antineoplastic agent (CHEBI:35610)
withalongolide B (CHEBI:69107) is a 4-hydroxy steroid (CHEBI:62846)
withalongolide B (CHEBI:69107) is a enone (CHEBI:51689)
withalongolide B (CHEBI:69107) is a epoxy steroid (CHEBI:145217)
withalongolide B (CHEBI:69107) is a ergostanoid (CHEBI:50403)
withalongolide B (CHEBI:69107) is a primary alcohol (CHEBI:15734)
withalongolide B (CHEBI:69107) is a secondary alcohol (CHEBI:35681)
withalongolide B (CHEBI:69107) is a withanolide (CHEBI:74716)
withalongolide B (CHEBI:69107) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4β,5β,6β,22R)-4,19-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Registry NumbersSources
Reaxys:22217707Reaxys
Citations