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CHEBI:69108 - withalongolide C

ChEBI IDCHEBI:69108
ChEBI Namewithalongolide C
Stars
DefinitionA withanolide that is withaferin A substituted by a hydroxy group at position 11. Isolated from Physalis longifolia, it exhibits antineoplastic activity.
Last Modified29 October 2019
DownloadsMolfile
FormulaC28H38O7
Net Charge0
Average Mass486.605
Monoisotopic Mass486.26175
SMILES[H][C@@]12CC[C@]([H])([C@H](C)[C@@]3([H])CC(C)=C(CO)C(=O)O3)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H]2O[C@]23[C@@H](O)C=CC(=O)[C@@]31C
InChIInChI=1S/C28H38O7/c1-13-9-20(34-25(33)16(13)12-29)14(2)17-5-6-18-15-10-23-28(35-23)22(32)8-7-21(31)27(28,4)24(15)19(30)11-26(17,18)3/h7-8,14-15,17-20,22-24,29-30,32H,5-6,9-12H2,1-4H3/t14-,15-,17+,18-,19-,20+,22-,23+,24+,26+,27+,28+/m0/s1
InChIKeyUPRPPTFVJBNIPP-VAPFTTHESA-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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 C (CHEBI:69108) has functional parent withaferin A (CHEBI:69120)
withalongolide C (CHEBI:69108) has role antineoplastic agent (CHEBI:35610)
withalongolide C (CHEBI:69108) has role metabolite (CHEBI:25212)
withalongolide C (CHEBI:69108) has role plant metabolite (CHEBI:76924)
withalongolide C (CHEBI:69108) is a 11β-hydroxy steroid (CHEBI:35346)
withalongolide C (CHEBI:69108) is a 27-hydroxy steroid (CHEBI:37914)
withalongolide C (CHEBI:69108) is a 4-hydroxy steroid (CHEBI:62846)
withalongolide C (CHEBI:69108) is a enone (CHEBI:51689)
withalongolide C (CHEBI:69108) is a epoxy steroid (CHEBI:145217)
withalongolide C (CHEBI:69108) is a ergostanoid (CHEBI:50403)
withalongolide C (CHEBI:69108) is a primary alcohol (CHEBI:15734)
withalongolide C (CHEBI:69108) is a secondary alcohol (CHEBI:35681)
withalongolide C (CHEBI:69108) is a withanolide (CHEBI:74716)
withalongolide C (CHEBI:69108) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4β,5β,6β,11β,22R)-4,11,27-trihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione
Synonym  Source
11β-hydroxywithaferin AChEBI
Registry NumbersSources
Reaxys:22217709Reaxys
Citations