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CHEBI:65628 - 16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one

ChEBI IDCHEBI:65628
ChEBI Name16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
Stars
ASCII Name16beta-[(alpha-L-arabinopyranosyl)oxy]-3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxycholest-5-en-22-one
DefinitionA steroid saponin that is (3β,16β,20R)-3,16,17-trihydroxycholest-5-en-22-one attached to a α-L-arabinopyranosyl residue at position 16 and a β-D-glucopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Ornithogalum thyrsoides and Galtonia candicans, it exhibits cytotoxic activity.
Last Modified31 July 2013
DownloadsMolfile
FormulaC38H62O13
Net Charge0
Average Mass726.901
Monoisotopic Mass726.41904
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]3O)C[C@@]21[H]
InChIInChI=1S/C38H62O13/c1-18(2)6-9-25(40)19(3)38(47)28(51-34-32(45)29(42)26(41)17-48-34)15-24-22-8-7-20-14-21(10-12-36(20,4)23(22)11-13-37(24,38)5)49-35-33(46)31(44)30(43)27(16-39)50-35/h7,18-19,21-24,26-35,39,41-47H,6,8-17H2,1-5H3/t19-,21-,22+,23-,24-,26-,27+,28-,29-,30+,31-,32+,33+,34-,35+,36-,37-,38+/m0/s1
InChIKeyNQDDCCOUDFVXKO-DAVJFRSBSA-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)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65628) has role antineoplastic agent (CHEBI:35610)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65628) has role metabolite (CHEBI:25212)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65628) is a 17-hydroxy steroid (CHEBI:36838)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65628) is a cholestanoid (CHEBI:50401)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65628) is a steroid saponin (CHEBI:61655)
16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65628) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(3β,16β,20R)-16-(α-L-arabinopyranosyloxy)-17-hydroxy-22-oxocholest-5-en-3-yl β-D-glucopyranoside
Citations