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CHEBI:65622 - 3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one

ChEBI IDCHEBI:65622
ChEBI Name3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one
Stars
ASCII Name3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyloxy]cholest-5-en-22-one
DefinitionA steroid saponin that is 3,16,17-trihydroxycholest-5-en-22-one attached to a β-D-glucopyranosyl residue at position 3 and a 2-O-acetyl-3-O-(β-D-xylopyranosyl)-α-L-arabinopyranosyl residue at position 16 via a glycosidic linkage. Isolated from Ornithogalum thyrsoides and Galtonia candicans, it exhibits cytotoxic activity.
Last Modified30 July 2013
DownloadsMolfile
FormulaC45H72O18
Net Charge0
Average Mass901.053
Monoisotopic Mass900.47187
SMILES[H][C@@]12CC=C3C[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@](O)([C@@H](C)C(=O)CCC(C)C)[C@@H](O[C@@H]3OC[C@H](O)[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@H]3OC(C)=O)C[C@@]21[H]
InChIInChI=1S/C45H72O18/c1-20(2)7-10-28(48)21(3)45(56)32(62-42-39(59-22(4)47)38(30(50)19-58-42)63-40-36(54)33(51)29(49)18-57-40)16-27-25-9-8-23-15-24(11-13-43(23,5)26(25)12-14-44(27,45)6)60-41-37(55)35(53)34(52)31(17-46)61-41/h8,20-21,24-27,29-42,46,49-56H,7,9-19H2,1-6H3/t21-,24-,25+,26-,27-,29+,30-,31+,32-,33-,34+,35-,36+,37+,38-,39+,40-,41+,42-,43-,44-,45+/m0/s1
InChIKeyFOCIGGVGHNGKRW-SWPAXGJUSA-N
Species of MetaboliteComponentSourceComments
Galtonia candicans (ncbitaxon:81751) bulb (BTO:0000159) PubMed (11515577)
Ornithogalum thyrsoides (ncbitaxon:484172) bulb (BTO:0000159) PubMed (12398536)
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.
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)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) has role antineoplastic agent (CHEBI:35610)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) has role metabolite (CHEBI:25212)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) is a 17-hydroxy steroid (CHEBI:36838)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) is a acetate ester (CHEBI:47622)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) is a cholestanoid (CHEBI:50401)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) is a steroid saponin (CHEBI:61655)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyloxy]cholest-5-en-22-one (CHEBI:65622) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(3β,16β,20R)-16-{[2-O-acetyl-3-O-(β-D-xylopyranosyl)-α-L-arabinopyranosyl]oxy}-17-hydroxy-22-oxocholest-5-en-3-yl β-D-glucopyranoside
Citations