CHEBI:65853 - 5α,8α-epidioxysterol

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ChEBI Name 5α,8α-epidioxysterol
ChEBI ID CHEBI:65853
ChEBI ASCII Name 5alpha,8alpha-epidioxysterol
Definition A 3β-sterol that consists of 24-methylcholest-6-en-3β-ol with a peroxy group between positions 5 and 8 and a methylene group between positions 22 and 23. An antineoplastic agent isolated from Sinularia sp.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H46O3
Net Charge 0
Average Mass 442.67370
Monoisotopic Mass 442.34470
InChI InChI=1S/C29H46O3/c1-17(2)18(3)21-15-22(21)19(4)23-7-8-24-26(23,5)11-10-25-27(6)12-9-20(30)16-28(27)13-14-29(24,25)32-31-28/h13-14,17-25,30H,7-12,15-16H2,1-6H3/t18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,28-,29+/m1/s1
InChIKey FYNMKNFAKCHMLL-PPXWZDJSSA-N
SMILES [H][C@@]1(C[C@]1([H])[C@@H](C)[C@@]1([H])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)C(C)C
Metabolite of Species Details
Sinularia (NCBI:txid51814) 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-epidioxysterol (CHEBI:65853) has role antineoplastic agent (CHEBI:35610)
5α,8α-epidioxysterol (CHEBI:65853) has role metabolite (CHEBI:25212)
5α,8α-epidioxysterol (CHEBI:65853) is a 3β-sterol (CHEBI:35348)
5α,8α-epidioxysterol (CHEBI:65853) is a cyclopropanes (CHEBI:51454)
5α,8α-epidioxysterol (CHEBI:65853) is a organic peroxide (CHEBI:25702)
IUPAC Name
(3S,5S,8S,9R,10R,13R,14R,17R)-10,13-dimethyl-17-[(1R)-1-{(1R,2R)-2-[(2R)-3-methylbutan-2-yl]cyclopropyl}ethyl]-1,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-2H-5,8-epidioxycyclopenta[a]phenanthren-3-ol
Synonym Source
22R,23R,24R-5α,8α-epidioxy-22,23-methylene-24-methylcholest-6-en-3β-ol ChEBI
Registry Number Type Source
20596441 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10650100 PubMed citation Europe PMC
Last Modified
03 October 2012