CHEBI:65852 - (22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside

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ChEBI Name (22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside
ChEBI ID CHEBI:65852
ChEBI ASCII Name (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9,22-triene-3beta-ol-3-O-beta-D-glucopyranoside
Definition A sterol 3-β-D-glucoside that is ergosta-6,9,22-triene-3β-ol with a peroxy group between positions 5 and 8 and is substituted by a β-D-glucopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from the fruit bodies of Chlorophyllum molybdites, it exhibits cytotoxicity against Kato III cells.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C34H52O8
Net Charge 0
Average Mass 588.77190
Monoisotopic Mass 588.36622
InChI InChI=1S/C34H52O8/c1-19(2)20(3)7-8-21(4)23-9-10-25-31(23,5)13-12-26-32(6)14-11-22(17-33(32)15-16-34(25,26)42-41-33)39-30-29(38)28(37)27(36)24(18-35)40-30/h7-8,12,15-16,19-25,27-30,35-38H,9-11,13-14,17-18H2,1-6H3/b8-7+/t20-,21+,22-,23+,24+,25+,27+,28-,29+,30+,31+,32+,33+,34-/m0/s1
InChIKey PIUDVAYSOWOHCO-UFXGVOTHSA-N
SMILES [H][C@@]1(O[C@H]2CC[C@]3(C)C4=CC[C@]5(C)[C@]([H])(CC[C@@]5([H])[C@]44OO[C@@]3(C2)C=C4)[C@H](C)\C=C\[C@H](C)C(C)C)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Metabolite of Species Details
Chlorophyllum molybdites (NCBI:txid34430) Found in fruit (BTO:0000486). See: PubMed
Roles Classification
Chemical Role(s): oxidising agent
A substance that removes electrons from another reactant in a redox reaction.
(via peroxides )
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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 (22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (CHEBI:65852) has role antineoplastic agent (CHEBI:35610)
(22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (CHEBI:65852) has role fungal metabolite (CHEBI:76946)
(22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (CHEBI:65852) is a cholestanoid (CHEBI:50401)
(22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (CHEBI:65852) is a monosaccharide derivative (CHEBI:63367)
(22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (CHEBI:65852) is a organic peroxide (CHEBI:25702)
(22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside (CHEBI:65852) is a sterol 3-β-D-glucoside (CHEBI:37424)
IUPAC Name
(3S,5S,8S,10R,13R,14R,17R)-17-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,3,4,10,12,13,14,15,16,17-decahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-yl β-D-glucopyranoside
Registry Number Type Source
9031469 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11515573 PubMed citation Europe PMC
Last Modified
14 April 2015