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

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ChEBI Name 16β-[(α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
ChEBI ID CHEBI:65628
ChEBI ASCII Name 16beta-[(alpha-L-arabinopyranosyl)oxy]-3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxycholest-5-en-22-one
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C38H62O13
Net Charge 0
Average Mass 726.89110
Monoisotopic Mass 726.41904
InChI InChI=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
InChIKey NQDDCCOUDFVXKO-DAVJFRSBSA-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]2O)[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 16beta-[(alpha-L-arabinopyranosyl)oxy]-3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxycholest-5-en-22-one )
(via saponin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
(via 16beta-[(alpha-L-arabinopyranosyl)oxy]-3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxycholest-5-en-22-one )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-D-glucoside (CHEBI:22798)
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)
IUPAC Name
(3β,16β,20R)-16-(α-L-arabinopyranosyloxy)-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
31 July 2013