CHEBI:65621 - 3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one

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ChEBI Name 3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one
ChEBI ID CHEBI:65621
ChEBI ASCII Name 3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]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-[2-O-(3,4-dimethoxybenzoyl)-β-D-xylopyranosyl]-α-L-arabinopyranosyl residue at position 16 via a glycosidic linkage. Isolated from Ornithogalum thyrsoides and Galtonia candicans, it exhibits antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C54H80O21
Net Charge 0
Average Mass 1065.20040
Monoisotopic Mass 1064.51921
InChI InChI=1S/C54H80O21/c1-25(2)9-13-34(57)26(3)54(65)40(21-33-31-12-11-29-20-30(15-17-52(29,5)32(31)16-18-53(33,54)6)71-49-44(63)43(62)42(61)39(22-55)72-49)73-51-47(70-27(4)56)45(36(59)24-69-51)75-50-46(41(60)35(58)23-68-50)74-48(64)28-10-14-37(66-7)38(19-28)67-8/h10-11,14,19,25-26,30-33,35-36,39-47,49-51,55,58-63,65H,9,12-13,15-18,20-24H2,1-8H3/t26-,30-,31+,32-,33-,35+,36-,39+,40-,41-,42+,43-,44+,45-,46+,47+,49+,50-,51-,52-,53-,54+/m0/s1
InChIKey LCNZQZQWMXUXKA-MKWWFOLFSA-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]3OC(=O)c3ccc(OC)c(OC)c3)[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-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]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-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) has functional parent 3,4-dimethoxybenzoic acid (CHEBI:296881)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) has role antineoplastic agent (CHEBI:35610)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) has role metabolite (CHEBI:25212)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) is a β-D-glucoside (CHEBI:22798)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) is a 17-hydroxy steroid (CHEBI:36838)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) is a acetate ester (CHEBI:47622)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) is a benzoate ester (CHEBI:36054)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) is a cholestanoid (CHEBI:50401)
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4-dimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65621) is a steroid saponin (CHEBI:61655)
IUPAC Name
(3β,16β,20R)-16-({2-O-acetyl-3-O-[2-O-(3,4-dimethoxybenzoyl)-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