CHEBI:65851 - 5α,8α-epidioxycholest-6-en-3β-ol

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ChEBI Name 5α,8α-epidioxycholest-6-en-3β-ol
ChEBI ID CHEBI:65851
ChEBI ASCII Name 5alpha,8alpha-epidioxycholest-6-en-3beta-ol
Definition A cholestanoid that is cholest-6-ene substituted by a β-hydroxy group at position 3 and a peroxy group between positions 5 and 8 (the 5α,8α stereoisomer). Isolated from the sea urchin Diadema setosum, it exhibits cytotoxicity against variuos cancer cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H44O3
Net Charge 0
Average Mass 416.63650
Monoisotopic Mass 416.32905
InChI InChI=1S/C27H44O3/c1-18(2)7-6-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)30-29-26/h15-16,18-23,28H,6-14,17H2,1-5H3/t19-,20+,21-,22-,23-,24-,25-,26-,27+/m1/s1
InChIKey FOISYVRNZSWLHL-MEKQHADNSA-N
SMILES [H][C@@]1(CC[C@]2([H])[C@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)C[C@@]33OO[C@@]21C=C3)[C@H](C)CCCC(C)C
Metabolite of Species Details
Diadema setosum (NCBI:txid31175) Found in body wall (BTO:0000139). 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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5α,8α-epidioxycholest-6-en-3β-ol (CHEBI:65851) has role antineoplastic agent (CHEBI:35610)
5α,8α-epidioxycholest-6-en-3β-ol (CHEBI:65851) has role metabolite (CHEBI:25212)
5α,8α-epidioxycholest-6-en-3β-ol (CHEBI:65851) is a 3β-sterol (CHEBI:35348)
5α,8α-epidioxycholest-6-en-3β-ol (CHEBI:65851) is a cholestanoid (CHEBI:50401)
5α,8α-epidioxycholest-6-en-3β-ol (CHEBI:65851) is a organic peroxide (CHEBI:25702)
IUPAC Name
(3S,5S,8S,9R,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
Manual Xref Database
9604856 ChemSpider
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Registry Number Type Source
46010 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15357000 PubMed citation Europe PMC
Last Modified
21 January 2013