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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 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 ID CHEBI:65622
ChEBI ASCII Name 3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyloxy]cholest-5-en-22-one
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C45H72O18
Net Charge 0
Average Mass 901.04240
Monoisotopic Mass 900.47187
InChI InChI=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
InChIKey FOCIGGVGHNGKRW-SWPAXGJUSA-N
SMILES [H][C@@]12CC=C3C[C@H](CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])C[C@H](O[C@@H]2OC[C@H](O)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2OC(C)=O)[C@]1(O)[C@@H](C)C(=O)CCC(C)C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Ornithogalum thyrsoides (NCBI:txid484172) Found in bulb (BTO:0000159). See: PubMed
Galtonia candicans (NCBI:txid81751) Found in bulb (BTO:0000159). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via 3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyloxy]cholest-5-en-22-one )
(via saponin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
(via 3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyloxy]cholest-5-en-22-one )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
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 Waiting for Citations Types Sources
11515577 PubMed citation Europe PMC
12398536 PubMed citation Europe PMC
Last Modified
30 July 2013