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CHEBI:69108 - withalongolide C

Default Structure
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:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
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