3beta-[(O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-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 (CHEBI:65625)

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CHEBI:65625 - 3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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 ID	CHEBI:65625
ChEBI Name	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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
Stars
ASCII Name	3beta-[(O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-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 isolated from Ornithogalum thyrsoides and has been shown to exhibit cytotoxic activity.
Last Modified	30 July 2013
Downloads	Molfile

Formula	C66H100O31
Net Charge	0
Average Mass	1389.495
Monoisotopic Mass	1388.62486
SMILES	[H][C@@]1(O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](O[C@H]4CC[C@@]5(C)C(=CC[C@@]6([H])[C@]7([H])C[C@H](O[C@@H]8OC[C@H](O)[C@H](O[C@@H]9OC[C@@H](O)[C@H](O)[C@H]9OC(=O)c9ccc(OC)c(OC)c9)[C@H]8OC(C)=O)[C@](O)([C@@H](C)C(=O)CCC(C)C)[C@@]7(C)CC[C@@]65[H])C4)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C66H100O31/c1-27(2)9-13-36(70)28(3)66(83)44(94-63-57(89-29(4)69)54(38(72)25-87-63)96-62-56(45(73)37(71)24-86-62)95-58(82)30-10-14-39(84-7)40(19-30)85-8)21-35-33-12-11-31-20-32(15-17-64(31,5)34(33)16-18-65(35,66)6)90-60-51(79)49(77)47(75)43(93-60)26-88-59-53(81)50(78)55(42(23-68)92-59)97-61-52(80)48(76)46(74)41(22-67)91-61/h10-11,14,19,27-28,32-35,37-38,41-57,59-63,67-68,71-81,83H,9,12-13,15-18,20-26H2,1-8H3/t28-,32-,33+,34-,35-,37+,38-,41+,42+,43+,44-,45-,46+,47+,48-,49-,50+,51+,52+,53+,54-,55+,56+,57+,59+,60+,61-,62-,63-,64-,65-,66+/m0/s1
InChIKey	ZFJWITSYHMOZQR-KWGNHGRXSA-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-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) has functional parent 3,4-dimethoxybenzoic acid (CHEBI:296881)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) has role antineoplastic agent (CHEBI:35610)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) has role metabolite (CHEBI:25212)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) is a 17-hydroxy steroid (CHEBI:36838)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) is a acetate ester (CHEBI:47622)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) is a benzoate ester (CHEBI:36054)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) is a cholestanoid (CHEBI:50401)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) is a steroid saponin (CHEBI:61655)
	3β-[(O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-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:65625) is a β-D-glucoside (CHEBI:22798)

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-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside

Citations