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CHEBI:69106 - withalongolide A

ChEBI IDCHEBI:69106
ChEBI Namewithalongolide A
Stars
DefinitionA withanolide that is withaferin A substituted by a hydroxy group at position 19. Isolated from Physalis longifolia, it exhibits antineoplastic activitiy.
Last Modified29 October 2019
DownloadsMolfile
FormulaC28H38O7
Net Charge0
Average Mass486.605
Monoisotopic Mass486.26175
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(CO)C(=O)O1
InChIInChI=1S/C28H38O7/c1-14-10-21(34-25(33)17(14)12-29)15(2)18-4-5-19-16-11-24-28(35-24)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h6-7,15-16,18-21,23-24,29-30,32H,4-5,8-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
InChIKeyFJMXKFSOKLFYRC-CKNDUULBSA-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 Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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 A (CHEBI:69106) has functional parent withaferin A (CHEBI:69120)
withalongolide A (CHEBI:69106) has role antineoplastic agent (CHEBI:35610)
withalongolide A (CHEBI:69106) has role plant metabolite (CHEBI:76924)
withalongolide A (CHEBI:69106) is a 19-hydroxy steroid (CHEBI:36842)
withalongolide A (CHEBI:69106) is a 27-hydroxy steroid (CHEBI:37914)
withalongolide A (CHEBI:69106) is a 4-hydroxy steroid (CHEBI:62846)
withalongolide A (CHEBI:69106) is a enone (CHEBI:51689)
withalongolide A (CHEBI:69106) is a epoxy steroid (CHEBI:145217)
withalongolide A (CHEBI:69106) is a ergostanoid (CHEBI:50403)
withalongolide A (CHEBI:69106) is a primary alcohol (CHEBI:15734)
withalongolide A (CHEBI:69106) is a secondary alcohol (CHEBI:35681)
withalongolide A (CHEBI:69106) is a withanolide (CHEBI:74716)
withalongolide A (CHEBI:69106) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4β,5β,6β,22R)-4,19,27-trihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Synonym  Source
19-hydroxywithaferin AChEBI
Registry NumbersSources
Reaxys:22217708Reaxys
Citations