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

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

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ChEBI ID	CHEBI:65852
ChEBI Name	(22E,24R)-5α,8α-epidioxyergosta-6,9,22-triene-3β-ol-3-O-β-D-glucopyranoside
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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.
Last Modified	14 April 2015
Downloads	Molfile

Formula	C34H52O8
Net Charge	0
Average Mass	588.782
Monoisotopic Mass	588.36622
SMILES	[H][C@@]1(O[C@H]2CC[C@]3(C)C4=CC[C@@]5(C)[C@@]([H])(CC[C@]5([H])[C@H](C)/C=C/[C@H](C)C(C)C)[C@@]45C=C[C@]3(C2)OO5)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
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

Species of Metabolite	Component	Source	Comments
Chlorophyllum molybdites (ncbitaxon:34430)	fruit (BTO:0000486)	PubMed (11515573)

Roles Classification

Chemical Role:	oxidising agent A substance that removes electrons from another reactant in a redox reaction.
Biological Roles:	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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	(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 Numbers	Sources
Reaxys:9031469	Reaxys

Citations