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CHEBI:69119 - sitoindoside IX

ChEBI IDCHEBI:69119
ChEBI Namesitoindoside IX
Stars
DefinitionA withanolide saponin that consists of withaferin A attached to a β-D-glucopyranosyl residue at position 27 via a glycosidic linkage. Isolated from Physalis longifolia, it exhibits antineoplastic activity.
Last Modified29 October 2019
DownloadsMolfile
FormulaC34H48O11
Net Charge0
Average Mass632.747
Monoisotopic Mass632.31966
SMILES[H][C@@]12C[C@H]3O[C@]34[C@@H](O)C=CC(=O)[C@]4(C)[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@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)O1
InChIInChI=1S/C34H48O11/c1-15-11-22(43-30(41)18(15)14-42-31-29(40)28(39)27(38)23(13-35)44-31)16(2)19-5-6-20-17-12-26-34(45-26)25(37)8-7-24(36)33(34,4)21(17)9-10-32(19,20)3/h7-8,16-17,19-23,25-29,31,35,37-40H,5-6,9-14H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,25-,26+,27+,28-,29+,31+,32+,33-,34+/m0/s1
InChIKeyWKCJIGSUKSPCKI-WNXUODGFSA-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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
sitoindoside IX (CHEBI:69119) has functional parent withaferin A (CHEBI:69120)
sitoindoside IX (CHEBI:69119) has role antineoplastic agent (CHEBI:35610)
sitoindoside IX (CHEBI:69119) has role plant metabolite (CHEBI:76924)
sitoindoside IX (CHEBI:69119) is a 4-hydroxy steroid (CHEBI:62846)
sitoindoside IX (CHEBI:69119) is a enone (CHEBI:51689)
sitoindoside IX (CHEBI:69119) is a epoxy steroid (CHEBI:145217)
sitoindoside IX (CHEBI:69119) is a ergostanoid (CHEBI:50403)
sitoindoside IX (CHEBI:69119) is a monosaccharide derivative (CHEBI:63367)
sitoindoside IX (CHEBI:69119) is a secondary alcohol (CHEBI:35681)
sitoindoside IX (CHEBI:69119) is a withanolide saponin (CHEBI:76344)
sitoindoside IX (CHEBI:69119) is a β-D-glucoside (CHEBI:22798)
sitoindoside IX (CHEBI:69119) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(4β,5β,6β,22R)-4-hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl β-D-glucopyranoside
Synonym  Source
27-O-β-D-glucopyranosylwithaferin AChEBI
Registry NumbersSources
Reaxys:8605359Reaxys
CAS:118853-45-5ChemIDplus
Citations