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CHEBI:69126 - withalongolide G

Default Structure
ChEBI IDCHEBI:69126
ChEBI Namewithalongolide G
Stars
DefinitionA withanolide that is 2,3-dihydrowithaferin A substituted by a hydroxy group at position 19 and a sulfoxy group at position 3. Isolated from Physalis longifolia, it exhibits antineoplastic activity.
Last Modified29 October 2019
DownloadsMolfile
FormulaC28H40O11S
Net Charge0
Average Mass584.684
Monoisotopic Mass584.22913
SMILES[H][C@@]12C[C@H]3O[C@]34[C@@H](O)[C@@H](OS(=O)(=O)O)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/C28H40O11S/c1-13-8-20(37-25(33)16(13)11-29)14(2)17-4-5-18-15-9-23-28(38-23)24(32)21(39-40(34,35)36)10-22(31)27(28,12-30)19(15)6-7-26(17,18)3/h14-15,17-21,23-24,29-30,32H,4-12H2,1-3H3,(H,34,35,36)/t14-,15-,17+,18-,19-,20+,21-,23+,24-,26+,27-,28-/m0/s1
InChIKeyCOBSTJNYJHEYIM-WQWZRYHASA-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 G (CHEBI:69126) has functional parent withaferin A (CHEBI:69120)
withalongolide G (CHEBI:69126) has role antineoplastic agent (CHEBI:35610)
withalongolide G (CHEBI:69126) has role metabolite (CHEBI:25212)
withalongolide G (CHEBI:69126) has role plant metabolite (CHEBI:76924)
withalongolide G (CHEBI:69126) is a 19-hydroxy steroid (CHEBI:36842)
withalongolide G (CHEBI:69126) is a 27-hydroxy steroid (CHEBI:37914)
withalongolide G (CHEBI:69126) is a 4-hydroxy steroid (CHEBI:62846)
withalongolide G (CHEBI:69126) is a epoxy steroid (CHEBI:145217)
withalongolide G (CHEBI:69126) is a ergostanoid (CHEBI:50403)
withalongolide G (CHEBI:69126) is a primary alcohol (CHEBI:15734)
withalongolide G (CHEBI:69126) is a secondary alcohol (CHEBI:35681)
withalongolide G (CHEBI:69126) is a steroid sulfate (CHEBI:16158)
withalongolide G (CHEBI:69126) is a withanolide (CHEBI:74716)
withalongolide G (CHEBI:69126) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(3β,4β,5β,6β,22R)-4,19,27-trihydroxy-1,26-dioxo-5,6:22,26-diepoxyergost-24-en-3-yl hydrogen sulfate
Synonym  Source
2,3-dihydro-19-hydroxy-3β-O-sulfatewithaferin AChEBI
Registry NumbersSources
Reaxys:22217716Reaxys
Citations