CHEBI:65855 - 16,23-epoxy-5β-cholestane triglycoside

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ChEBI Name 16,23-epoxy-5β-cholestane triglycoside
ChEBI ID CHEBI:65855
ChEBI ASCII Name 16,23-epoxy-5beta-cholestane triglycoside
Definition A sterol 3-β-D-glucoside that is 16,23-epoxycholest-24-ene-3,22-diol substituted by a 6-deoxy-α-L-mannopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl moiety at position 3 via a glycosidic linkage (the 3β,5β,16β,22R,23S stereoisomer). Isolated from bulbs of Ornithogalum saundersiae, it exhibits inhibitory activity on proliferation of human peripheral blood lymphocytes.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C45H74O17
Net Charge 0
Average Mass 887.05890
Monoisotopic Mass 886.49260
InChI InChI=1S/C45H74O17/c1-18(2)13-27-31(48)19(3)30-26(58-27)15-25-23-8-7-21-14-22(9-11-44(21,5)24(23)10-12-45(25,30)6)57-42-39(36(53)33(50)28(16-46)59-42)62-43-40(37(54)34(51)29(17-47)60-43)61-41-38(55)35(52)32(49)20(4)56-41/h13,19-43,46-55H,7-12,14-17H2,1-6H3/t19-,20-,21+,22-,23+,24-,25-,26-,27-,28+,29+,30-,31+,32-,33+,34+,35+,36-,37-,38+,39+,40+,41-,42+,43-,44-,45-/m0/s1
InChIKey AJNYRTVTKHEZMG-BYMWGYRGSA-N
SMILES [H][C@]1(O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]1([H])O[C@H]1CC[C@@]2(C)[C@]([H])(CC[C@]3([H])[C@]2([H])CC[C@@]2(C)[C@@]3([H])C[C@]3([H])O[C@@H](C=C(C)C)[C@H](O)[C@@H](C)[C@]23[H])C1
Metabolite of Species Details
Ornithogalum saundersiae (NCBI:txid484171) 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 saponin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) has role antineoplastic agent (CHEBI:35610)
16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) has role metabolite (CHEBI:25212)
16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) is a 22-hydroxy steroid (CHEBI:36863)
16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) is a cholestanoid (CHEBI:50401)
16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) is a cyclic ether (CHEBI:37407)
16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) is a sterol 3-β-D-glucoside (CHEBI:37424)
16,23-epoxy-5β-cholestane triglycoside (CHEBI:65855) is a trisaccharide derivative (CHEBI:63571)
IUPAC Name
(3β,5β,16β,22R,23S)-22-hydroxy-16,23-epoxycholest-24-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside
Registry Number Type Source
8184507 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
7586067 PubMed citation Europe PMC
Last Modified
21 January 2013