KEGG   ENZYME: 3.3.2.11
Entry
EC 3.3.2.11                 Enzyme                                 
Name
cholesterol-5,6-oxide hydrolase;
cholesterol-epoxide hydrolase;
ChEH
Class
Hydrolases;
Acting on ether bonds;
Ether hydrolases
Sysname
5,6alpha-epoxy-5alpha-cholestan-3beta-ol hydrolase
Reaction(IUBMB)
(1) 5,6alpha-epoxy-5alpha-cholestan-3beta-ol + H2O = 5alpha-cholestane-3beta,5alpha,6beta-triol [RN:R07597];
(2) 5,6beta-epoxy-5beta-cholestan-3beta-ol + H2O = 5alpha-cholestane-3beta,5alpha,6beta-triol [RN:R04792]
Reaction(KEGG)
R04792 R07597
Substrate
5,6alpha-epoxy-5alpha-cholestan-3beta-ol [CPD:C15992];
H2O [CPD:C00001];
5,6beta-epoxy-5beta-cholestan-3beta-ol [CPD:C05418]
Product
5alpha-cholestane-3beta,5alpha,6beta-triol
Comment
The activity has been attributed to the microsomal antiestrogen binding site, a complex formed by EC 5.3.3.5, cholestenol Delta-isomerase, and EC 1.3.1.21, 7-dehydrocholesterol reductase [6]. Both 5,6alpha-epoxy-5alpha-cholestan-3beta-ol and 5,6beta-epoxy-5beta-cholestan-3beta-ol are substrates [3]. The product is a competitive inhibitor of the reaction. In vertebrates, five epoxide-hydrolase enzymes have been identified to date: EC 3.3.2.6 (leukotriene-A4 hydrolase), EC 3.3.2.7 (hepoxilin-epoxide hydrolase), EC 3.3.2.9 (microsomal epoxide hydrolase), EC 3.3.2.10 (soluble epoxide hydrolase) and EC 3.3.2.11 (cholesterol-5,6-oxide hydrolase) [3].
History
EC 3.3.2.11 created 2006, modified 2024
Reference
1  [PMID:6401984]
  Authors
Levin W, Michaud DP, Thomas PE, Jerina DM.
  Title
Distinct rat hepatic microsomal epoxide hydrolases catalyze the hydration of cholesterol 5,6 alpha-oxide and certain xenobiotic alkene and arene oxides.
  Journal
Arch Biochem Biophys 220:485-94 (1983)
DOI:10.1016/0003-9861(83)90439-3
Reference
2  [PMID:6690087]
  Authors
Oesch F, Timms CW, Walker CH, Guenthner TM, Sparrow A, Watabe T, Wolf CR.
  Title
Existence of multiple forms of microsomal epoxide hydrolases with radically different substrate specificities.
  Journal
Carcinogenesis 5:7-9 (1984)
DOI:10.1093/carcin/5.1.7
Reference
3  [PMID:3941086]
  Authors
Sevanian A, McLeod LL.
  Title
Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase.
  Journal
J Biol Chem 261:54-9 (1986)
Reference
4  [PMID:11154734]
  Authors
Fretland AJ, Omiecinski CJ.
  Title
Epoxide hydrolases: biochemistry and molecular biology.
  Journal
Chem Biol Interact 129:41-59 (2000)
DOI:10.1016/S0009-2797(00)00197-6
Reference
5  [PMID:15748653]
  Authors
Newman JW, Morisseau C, Hammock BD.
  Title
Epoxide hydrolases: their roles and interactions with lipid metabolism.
  Journal
Prog Lipid Res 44:1-51 (2005)
DOI:10.1016/j.plipres.2004.10.001
Reference
6  [PMID:20615952]
  Authors
de Medina P, Paillasse MR, Segala G, Poirot M, Silvente-Poirot S.
  Title
Identification and pharmacological characterization of cholesterol-5,6-epoxide hydrolase as a target for tamoxifen and AEBS ligands.
  Journal
Proc Natl Acad Sci U S A 107:13520-5 (2010)
DOI:10.1073/pnas.1002922107
Other DBs
ExplorEnz - The Enzyme Database: 3.3.2.11
IUBMB Enzyme Nomenclature: 3.3.2.11
ExPASy - ENZYME nomenclature database: 3.3.2.11
BRENDA, the Enzyme Database: 3.3.2.11

  All links  
Protein sequence (59)   
   UniProt (12)   
   SWISS-PROT (9)   
   RefSeq(pep) (38)   
DNA sequence (42)   
   RefSeq(nuc) (40)   
   GenBank (1)   
   EMBL (1)   
Protein domain (6)   
   InterPro (6)   
All databases (107)   

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