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

ChEBI IDCHEBI:65851
ChEBI Name5α,8α-epidioxycholest-6-en-3β-ol
Stars
ASCII Name5alpha,8alpha-epidioxycholest-6-en-3beta-ol
DefinitionA 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.
Last Modified21 January 2013
DownloadsMolfile
FormulaC27H44O3
Net Charge0
Average Mass416.646
Monoisotopic Mass416.32905
SMILES[H][C@@]12CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)C[C@]34C=C[C@]21OO4
InChIInChI=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
InChIKeyFOISYVRNZSWLHL-MEKQHADNSA-N
Species of MetaboliteComponentSourceComments
Diadema setosum (ncbitaxon:31175) body wall (BTO:0000139) PubMed (15357000)
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-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 XrefsDatabases
9604856ChemSpider
Registry NumbersSources
Reaxys:46010Reaxys
Citations