KEGG   ENZYME: 3.3.2.9Help
Entry
EC 3.3.2.9                  Enzyme                                 

Name
microsomal epoxide hydrolase;
epoxide hydratase (ambiguous);
microsomal epoxide hydratase (ambiguous);
epoxide hydrase;
microsomal epoxide hydrase;
arene-oxide hydratase (ambiguous);
benzo[a]pyrene-4,5-oxide hydratase;
benzo(a)pyrene-4,5-epoxide hydratase;
aryl epoxide hydrase (ambiguous);
cis-epoxide hydrolase;
mEH
Class
Hydrolases;
Acting on ether bonds;
Ether hydrolases
BRITE hierarchy
Sysname
cis-stilbene-oxide hydrolase
Reaction(IUBMB)
cis-stilbene oxide + H2O = (+)-(1R,2R)-1,2-diphenylethane-1,2-diol [RN:R07627]
Reaction(KEGG)
Substrate
cis-stilbene oxide [CPD:C16014];
H2O [CPD:C00001]
Product
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol [CPD:C16015]
Comment
This is a key hepatic enzyme that is involved in the metabolism of numerous xenobiotics, such as 1,3-butadiene oxide, styrene oxide and the polycyclic aromatic hydrocarbon benzo[a]pyrene 4,5-oxide [5--7]. In a series of oxiranes with a lipophilic substituent of sufficient size (styrene oxides), monosubstituted as well as 1,1- and cis-1,2-disubstituted oxiranes serve as substrates or inhibitors of the enzyme. However, trans-1,2-disubstituted, tri-and tetra-substituted oxiranes are not substrates [9]. The reaction involves the formation of an hydroxyalkyl---enzyme intermediate [10]. 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) [7].
History
EC 3.3.2.9 created 2006 (EC 3.3.2.3 part-incorporated 2006)
Pathway
Metabolism of xenobiotics by cytochrome P450
Orthology
K01253  
microsomal epoxide hydrolase
Genes
HSA: 
2052(EPHX1)
PTR: 
457777(EPHX1)
PPS: 
100995858(EPHX1)
GGO: 
101130068(EPHX1)
PON: 
100173792(EPHX1)
MCC: 
700180(EPHX1)
MCF: 
MMU: 
13849(Ephx1)
RNO: 
25315(Ephx1)
CGE: 
HGL: 
101725522(Ephx1)
TUP: 
102495357(EPHX1)
CFA: 
480113(EPHX1)
AML: 
100477671(EPHX1)
FCA: 
101085519(EPHX1)
PTG: 
102949568(EPHX1)
BTA: 
535293(EPHX1)
BOM: 
102267623(EPHX1)
PHD: 
102316040(EPHX1)
CHX: 
100860945(EPHX1)
SSC: 
397639(EPHX1)
CFR: 
102519415(EPHX1)
BACU: 
103003233(EPHX1)
ECB: 
100054269(EPHX1)
MYB: 
102263401(EPHX1)
MYD: 
102767193(EPHX1)
PALE: 
102883919(EPHX1)
MDO: 
100025778(EPHX1)
SHR: 
100925093(EPHX1)
OAA: 
100081956(EPHX1)
GGA: 
421321(EPHX1) 421447
MGP: 
TGU: 
FAB: 
PHI: 
APLA: 
FPG: 
101914944(EPHX1)
FCH: 
102059804(EPHX1)
CLV: 
102085632(EPHX1)
ASN: 
102368835(EPHX1)
PSS: 
102457257(EPHX1)
ACS: 
XLA: 
432100(ephx1)
XTR: 
100158543(ephx1)
DRE: 
394043(ephx1)
TRU: 
MZE: 
OLA: 
XMA: 
LCM: 
102353239(EPHX1)
BFO: 
CIN: 
SPU: 
CEL: 
CELE_W01A11.1(W01A11.1)
CBR: 
BMY: 
LOA: 
TSP: 
NVE: 
TAD: 
PIC: 
MGR: 
ANI: 
AFM: 
ANG: 
ANI_1_312144(An16g02170)
CNE: 
UMA: 
REH: 
H16_A1767(h16_A1767) H16_A1793(h16_A1793)
BUR: 
BRA: 
BBT: 
HNE: 
GBE: 
PUB: 
SAR11_0803(ephX1)
BCL: 
MBB: 
BCG_1185(ephC) BCG_1977(ephB) BCG_3200c(mesTb) BCG_3201c(mesTa) BCG_3728(ephE)
MSM: 
AAU: 
FRA: 
FAL: 
SEN: 
STP: 
 » show all
Taxonomy
Reference
1
  Authors
Jakoby, W.B. and Fjellstedt, T.A.
  Title
Epoxidases.
  Journal
In: Boyer, P.D. (Ed.), The Enzymes, 3rd ed., vol. 7, Academic Press, New York, 1972, p. 199-212.
Reference
2  [PMID:240858]
  Authors
Lu AY, Ryan D, Jerina DM, Daly JW, Levin W.
  Title
Liver microsomal expoxide hydrase. Solubilization, purification, and characterization.
  Journal
J. Biol. Chem. 250 (1975) 8283-8.
  Organism
Homo sapiens, Rattus norvegicus, Cavia porcellus
Reference
3  [PMID:4463951]
  Authors
Oesch F.
  Title
Purification and specificity of a human microsomal epoxide hydratase.
  Journal
Biochem. J. 139 (1974) 77-88.
  Organism
Homo sapiens
Reference
4  [PMID:4998715]
  Authors
Oesch F, Daly J.
  Title
Solubilization, purification, and properties of a hepatic epoxide hydrase.
  Journal
Biochim. Biophys. Acta. 227 (1971) 692-7.
  Organism
Cavia porcellus
Reference
5  [PMID:7986671]
  Authors
Bellucci G, Chiappe C, Ingrosso G.
  Title
Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides.
  Journal
Chirality. 6 (1994) 577-82.
  Organism
Oryctolagus cuniculus
Reference
6  [PMID:15822179]
  Authors
Morisseau C, Hammock BD.
  Title
Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles.
  Journal
Annu. Rev. Pharmacol. Toxicol. 45 (2005) 311-33.
  Organism
Homo sapiens, Rattus norvegicus
Reference
7  [PMID:11154734]
  Authors
Fretland AJ, Omiecinski CJ.
  Title
Epoxide hydrolases: biochemistry and molecular biology.
  Journal
Chem. Biol. Interact. 129 (2000) 41-59.
  Organism
Rattus norvegicus
Reference
8  [PMID:4584115]
  Authors
Oesch F.
  Title
Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds.
  Journal
Xenobiotica. 3 (1973) 305-40.
  Organism
Homo sapiens, Macaca mulatta, Mus musculus, Rattus norvegicus, Sus scofa, Cavia porcellus, Oryctolagus cuniculus
Reference
9  [PMID:8199297]
  Authors
Lacourciere GM, Armstrong RN.
  Title
Microsomal and soluble epoxide hydrolases are members of the same family of C-X bond hydrolase enzymes.
  Journal
Chem. Res. Toxicol. 7 (1994) 121-4.
  Organism
Rattus norvegicus
Reference
10 [PMID:15748653]
  Authors
Newman JW, Morisseau C, Hammock BD.
  Title
Epoxide hydrolases: their roles and interactions with lipid metabolism.
  Journal
Prog. Lipid. Res. 44 (2005) 1-51.
  Organism
Homo sapiens, Rattus norvegicus
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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