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CHEBI:69126 - withalongolide G

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:
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 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