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CHEBI:65853 - 5α,8α-epidioxysterol

ChEBI IDCHEBI:65853
ChEBI Name5α,8α-epidioxysterol
Stars
ASCII Name5alpha,8alpha-epidioxysterol
DefinitionA 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.
Last Modified3 October 2012
DownloadsMolfile
FormulaC29H46O3
Net Charge0
Average Mass442.684
Monoisotopic Mass442.34470
SMILES[H][C@@]12CC[C@]([H])([C@H](C)[C@@]3([H])C[C@]3([H])[C@H](C)C(C)C)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)C[C@]34C=C[C@]21OO4
InChIInChI=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
InChIKeyFYNMKNFAKCHMLL-PPXWZDJSSA-N
Species of MetaboliteComponentSourceComments
Sinularia (ncbitaxon:51814) - PubMed (10650100)
Roles Classification
Chemical Role:
oxidising agent  A substance that removes electrons from another reactant in a redox reaction.
Biological Role:
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)
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-olChEBI
Registry NumbersSources
Reaxys:20596441Reaxys
Citations