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CHEBI:65629 - 16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one

ChEBI IDCHEBI:65629
ChEBI Name16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one
Stars
ASCII Name16beta-[(O-(2-O-(E)-cinnamoyl-beta-D-xylopyranosyl)-(1->2)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]-3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxycholest-5-en-22-one
DefinitionA steroid saponin isolated from Ornithogalum saundersiae and Galtonia candicans and has been shown to exhibit cytotoxic activity.
Last Modified31 July 2013
DownloadsMolfile
FormulaC54H78O19
Net Charge0
Average Mass1031.199
Monoisotopic Mass1030.51373
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)/C=C/c4ccccc4)[C@H]3OC(C)=O)C[C@@]21[H]
InChIInChI=1S/C54H78O19/c1-27(2)12-16-36(57)28(3)54(65)40(23-35-33-15-14-31-22-32(18-20-52(31,5)34(33)19-21-53(35,54)6)69-49-45(64)44(63)43(62)39(24-55)70-49)71-51-48(68-29(4)56)46(38(59)26-67-51)73-50-47(42(61)37(58)25-66-50)72-41(60)17-13-30-10-8-7-9-11-30/h7-11,13-14,17,27-28,32-35,37-40,42-51,55,58-59,61-65H,12,15-16,18-26H2,1-6H3/b17-13+/t28-,32-,33+,34-,35-,37+,38-,39+,40-,42-,43+,44-,45+,46-,47+,48+,49+,50-,51-,52-,53-,54+/m0/s1
InChIKeyXPJVFNVOMZCPBQ-QLOXOBCISA-N
Species of MetaboliteComponentSourceComments
Ornithogalum saundersiae (ncbitaxon:484171) bulb (BTO:0000159) DOI (10.1016/S0960-894X(97)00071-1)
Galtonia candicans (ncbitaxon:81751) bulb (BTO:0000159) PubMed (11515577)
Roles Classification
Biological Role:
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-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) has functional parent trans-cinnamic acid (CHEBI:35697)
16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) has role antineoplastic agent (CHEBI:35610)
16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) has role metabolite (CHEBI:25212)
16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) is a 17-hydroxy steroid (CHEBI:36838)
16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) is a acetate ester (CHEBI:47622)
16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) is a cinnamate ester (CHEBI:36087)
16β-[(O-(2-O-(E)-cinnamoyl-β-D-xylopyranosyl)-(1→2)-2-O-acetyl-α-L-arabinopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-17α-hydroxycholest-5-en-22-one (CHEBI:65629) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(3β,16β,20R)-16-[(2-O-acetyl-3-O-{2-O-[(2E)-3-phenylprop-2-enoyl]-β-D-xylopyranosyl}-α-L-arabinopyranosyl)oxy]-17-hydroxy-22-oxocholest-5-en-3-yl β-D-glucopyranoside
Citations