3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4,5-trimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620)

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CHEBI:65620 - 3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one

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ChEBI ID	CHEBI:65620
ChEBI Name	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one
Stars
ASCII Name	3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4,5-trimethoxybenzoyl-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-(3,4,5-trimethoxybenzoyl)-β-D-xylopyranosyl]-α-L-arabinopyranosyl residue at position 16 via a glycosidic linkage. Isolated from Ornithogalum thyrsoides, it exhibits antineoplastic activity.
Last Modified	30 July 2013
Downloads	Molfile

Formula	C55H82O22
Net Charge	0
Average Mass	1095.239
Monoisotopic Mass	1094.52977
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]4OC(=O)c4cc(OC)c(OC)c(OC)c4)[C@H]3OC(C)=O)C[C@@]21[H]
InChI	InChI=1S/C55H82O22/c1-25(2)10-13-34(58)26(3)55(66)40(21-33-31-12-11-29-20-30(14-16-53(29,5)32(31)15-17-54(33,55)6)73-50-44(64)43(63)42(62)39(22-56)74-50)75-52-48(72-27(4)57)45(36(60)24-71-52)77-51-47(41(61)35(59)23-70-51)76-49(65)28-18-37(67-7)46(69-9)38(19-28)68-8/h11,18-19,25-26,30-33,35-36,39-45,47-48,50-52,56,59-64,66H,10,12-17,20-24H2,1-9H3/t26-,30-,31+,32-,33-,35+,36-,39+,40-,41-,42+,43-,44+,45-,47+,48+,50+,51-,52-,53-,54-,55+/m0/s1
InChIKey	FLAULGUSZSPUPV-FDKPUIKUSA-N

Species of Metabolite	Component	Source	Comments
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-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) has functional parent 3,4,5-trimethoxybenzoic acid (CHEBI:454991)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) has role antineoplastic agent (CHEBI:35610)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) has role metabolite (CHEBI:25212)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) is a 17-hydroxy steroid (CHEBI:36838)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) is a acetate ester (CHEBI:47622)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) is a benzoate ester (CHEBI:36054)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) is a cholestanoid (CHEBI:50401)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) is a steroid saponin (CHEBI:61655)
	3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one (CHEBI:65620) is a β-D-glucoside (CHEBI:22798)

IUPAC Name
(3β,16β,20R)-16-({2-O-acetyl-3-O-[2-O-(3,4,5-trimethoxybenzoyl)-β-D-xylopyranosyl]-α-L-arabinopyranosyl}oxy)-17-hydroxy-22-oxocholest-5-en-3-yl β-D-glucopyranoside

Synonym	Source
3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxy-16β-[(O-(2-O-3,4,5-trimethoxybenzoyl-β-D-xylopyranosyl)-(1→3)-2-O-acetyl-α-L-arabinopyranosyl)oxy]cholest-5-en-22-one	ChEBI

Citations