Entry
Name
microsomal epoxide hydrolase;
microsomal oxirane/oxetane 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;
EPHX1 (gene name)
Class
Hydrolases;
Acting on ether bonds;
Ether hydrolases
BRITE hierarchy
Sysname
cis-stilbene-oxide hydrolase
Reaction(IUBMB)
(1) cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol [RN:
R07627 ];
(2) 1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O = 2-({[(4-methoxyphenyl)methyl](methyl)amino}methyl)-2-methylpropane-1,3-diol [RN:
R11930 ]
Reaction(KEGG)
Substrate
cis-stilbene oxide [CPD:
C16014 ];
H2O [CPD:
C00001 ];
1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine [CPD:
C21775 ]
Product
(1R,2R)-1,2-diphenylethane-1,2-diol;
2-({[(4-methoxyphenyl)methyl](methyl)amino}methyl)-2-methylpropane-1,3-diol [CPD:
C21776 ]
Comment
This is a key hepatic enzyme that catalyses the hydrolytic ring opening of oxiranes (epoxides) and oxetanes to give the corresponding diols. The enzyme is involved in the metabolism of numerous substrates including the stereoselective hydrolytic ring opening of 7-oxabicyclo[4.1.0]hepta-2,4-dienes (arene oxides) to the corresponding trans-dihydrodiols. The reaction proceeds via a triad mechanism and involves the formation of an hydroxyalkyl-enzyme intermediate. Five epoxide-hydrolase enzymes have been identified in vertebrates 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).
History
EC 3.3.2.9 created 2006 (EC 3.3.2.3 created 1978, modified 1999, part incorporated 2006), modified 2017
Pathway
ec00980 Metabolism of xenobiotics by cytochrome P450
Orthology
K01253 microsomal epoxide hydrolase
Genes
PON : 100173792(EPHX1) 100437687 129050146
PPYG : 129044266(EPHX1) 129044281
ANU : 117722048 117722080(Ephx1)
CGE : 100750792(Ephx1) 100758590
MAUA : 101835523 121137159
MORG : 121435840 121435939
MFOT : 126502146 126502147
AAMP : 119827559 119828107
CCAN : 109691482 109691483
NSU : 110571396(EPHX1) 123323815
TVP : 118845616 118845679 118846549 118848514
GGA : 421321(EPHX1) 421447(EPHX1L)
PCOC : 116229249 116231009(EPHX1)
MGP : 100539493 100545721(EPHX1)
CJO : 107311037(EPHX1) 107311272
TPAI : 128086988(EPHX1) 128088795
LMUT : 125688586 125690026(EPHX1)
NMEL : 110395399(EPHX1) 110396838
APLA : 101790722 101801005(EPHX1)
ACYG : 106029739 106031535(EPHX1)
CATA : 118253352(EPHX1) 118254315
AFUL : 116487216(EPHX1) 116487912
TGU : 100222959(EPHX1) 100227392
LSR : 110477509(EPHX1) 110477916
SCAN : 103817382 103819288(EPHX1)
PMOA : 120505979(EPHX1) 120506812
OTC : 121335741 121346931(EPHX1)
PRUF : 121357056(EPHX1) 121358526
GFR : 102041759(EPHX1) 102042334
FAB : 101806940(EPHX1) 101814529
OMA : 130250644 130251392(EPHX1)
PHI : 102100615 102109472(EPHX1)
PMAJ : 107201686 107201817(EPHX1)
CCAE : 111926266(EPHX1) 111926954
CCW : 104684354 104685565(EPHX1)
CBRC : 103612689(EPHX1) 103624121
ETL : 114059335 114073697(EPHX1)
ZAB : 102060438 102070896(EPHX1)
ZLE : 135445732 135446061(EPHX1)
SVG : 106853010 106853915(EPHX1)
MMEA : 130575999 130578661(EPHX1)
HRT : 120750675 120750700(EPHX1)
SATI : 136359328 136359558(EPHX1)
FPG : 101912868 101914944(EPHX1)
FCH : 102050687 102059804(EPHX1)
CCRI : 104161930(EPHX1) 104164844
NNT : 104405042(EPHX1) 104406829
SHAB : 115613418 115613509(EPHX1)
ACUN : 113478105(EPHX1) 113478705
TALA : 104363663 104368663(EPHX1)
ACHC : 115349892(EPHX1) 115350316
HALD : 104314305 104325460(EPHX1)
HLE : 104838144(EPHX1) 104840322
AGEN : 126051650 126052582
CSTI : 104553225(EPHX1) 104557585
LDI : 104348936(EPHX1) 104350292
MNB : 103775848 103777511(EPHX1)
DPUB : 104299949 104300896(EPHX1)
AVIT : 104267999(EPHX1) 104268224
PCRI : 104024981 104031194(EPHX1)
PCAO : 104043305(EPHX1) 104050640
AFOR : 103898883(EPHX1) 103902677
FGA : 104070751 104073957(EPHX1)
CLV : 102085632(EPHX1) 102092641
PGUU : 104458493(EPHX1) 104459025
PLET : 104618973(EPHX1) 104619723
CMAC : 104481879(EPHX1) 104486566
CUCA : 104056265 104067037(EPHX1)
TEO : 104370184(EPHX1) 104373427
BREG : 104637062 104637550(EPHX1)
OHA : 104329296 104331963(EPHX1)
ACAR : 104518807 104527715
CPEA : 104386207(EPHX1) 104396428
CVF : 104282324 104294655(EPHX1)
RTD : 128906503(EPHX1) 128907507
AAM : 106482713(EPHX1) 106485556
AROW : 112963396(EPHX1) 112973398
NPD : 112942790(EPHX1) 112957521
DNE : 112980038(EPHX1) 112997146
SCAM : 104151569(EPHX1) 104151692
ASN : 102368835(EPHX1) 102386213
AMJ : 102571832 102577262(EPHX1)
CPOO : 109319775(EPHX1) 109319862
PSS : 102456152 102457257(EPHX1)
CMY : 102934448(EPHX1) 102942209
CCAY : 125633687(EPHX1) 125633785
DCC : 119852686(EPHX1) 119853587
CPIC : 101936865(EPHX1) 101949762
TST : 117874510(EPHX1) 117874592
CABI : 116819064 116823869(EPHX1)
MRV : 120400560(EPHX1) 120400786
ACS : 100554472 100555586(ephx1)
ASAO : 132761291 132761373(EPHX1)
SUND : 121915364(EPHX1) 121934079
CTIG : 120307226(EPHX1) 120307716
TSR : 106541570 106542798(EPHX1)
PGUT : 117671761(EPHX1) 117671857
PTEX : 113433034(EPHX1) 113433158
NSS : 113420395(EPHX1) 113420917
VKO : 123025614(EPHX1) 123032030
PMUA : 114594523 114594618(EPHX1)
PRAF : 128410969 128411072(EPHX1)
ZVI : 118081778 118083220(EPHX1)
HCG : 128348556 128350086(EPHX1)
STOW : 125425855 125437417(EPHX1)
XLA : 108716563 432100(ephx1.L)
XTR : 100158543(ephx1) 105946059
NPR : 108787057(EPHX1) 108802126
RTEM : 120937855(EPHX1) 120938076 120938077
BBUF : 120999601(EPHX1) 120999807 120999808 120999809
BGAR : 122931001 122931002 122931003 122934641(EPHX1)
MUO : 115465310(EPHX1) 115465422
GSH : 117357613(EPHX1) 117358061
CAUA : 113062837 113063108 113120712
CGIB : 127938440 127983838
PTET : 122324509 122324778(ephx1)
MASI : 127410303 127415710
MANU : 129429137 129429138
CHAR : 105900083(ephx1) 105909349
LCO : 104918259 104918311(ephx1)
TBEN : 117489081(ephx1) 117499680(ephx5)
CGOB : 115003531(ephx1) 115020096
PGEO : 117439870(ephx1) 117459885(ephx5)
GACU : 117536607(ephx1) 117553133(ephx5)
EMAC : 134859195(ephx5) 134876952(ephx1)
ELY : 117248410(ephx5) 117271285(ephx1)
EFO : 125897156(ephx1) 125903794(ephx5)
PLEP : 121954425(ephx5) 121955668(ephx1) 121964048
SLUC : 116051469(ephx5) 116065557(ephx1)
ECRA : 117960017(ephx5) 117961646(ephx1)
ESP : 116705706 116705884(ephx1)
PFLV : 114571843 114573297(ephx1)
GAT : 120807746(ephx1) 120820603(ephx5)
PPUG : 119194870(ephx1) 119214299(ephx5)
AFB : 129092092(ephx5) 129107120(ephx1)
CLUM : 117727545(ephx1) 117743845(ephx5)
PSWI : 130202368 130203056 130207069(ephx5)
CANA : 137779690(ephx5) 137785945(ephx1)
CVE : 137871140(ephx1) 137883177(ephx5)
MSAM : 119909018(ephx1) 119916924(ephx5) 119918272
SCHU : 122863157(ephx1) 122884001(ephx5)
CUD : 121506648(ephx1) 121510636 121510637 121510638
ALAT : 119012274(ephx1) 119033157 119033158
ASTR : 137603608(ephx5) 137613282(ephx1)
MZE : 101463752 101487605(ephx1)
ONL : 100693015(ephx1) 100711364 100711636
OAU : 116314224(ephx1) 116318528
OLA : 101166982 101172051(ephx1)
OML : 112141000(ephx1) 112161741(ephx5)
CSAI : 133418422(ephx1) 133463478(ephx5)
XMA : 102229129 102230310(ephx1)
XCO : 114138263 114158698(ephx1)
XHE : 116713645 116734282(ephx1)
GAF : 122824815(ephx1) 122842946(ephx5)
PPRL : 129359987(ephx5) 129369188(ephx1)
CTUL : 119797626(ephx5) 119797636(ephx1)
GMU : 124859323(ephx5) 124881512(ephx1)
KMR : 108233942(ephx5) 108246518(ephx1)
ALIM : 106515907 106532950(ephx1)
NWH : 119417756(ephx5) 119417998(ephx1)
AOCE : 111583489(ephx1) 111585235
MCEP : 124999376(ephx1) 125019156(ephx5)
LCF : 108877099(ephx5) 108901766
SDU : 111220582 111239530(ephx1)
XGL : 120788741(ephx1) 120796290(ephx5)
SSCV : 125978755(ephx5) 125990183(ephx1)
SBIA : 133496267(ephx1) 133509465(ephx5)
PEE : 133409921(ephx5) 133416960(ephx1)
PTAO : 133468425(ephx1) 133485561(ephx5)
SJO : 128372653(ephx5) 128377137(ephx1)
SASA : 106571450 106607860
STRU : 115174737 115192170 115201724
OTW : 112250359(ephx1) 112261919
OMY : 110499486(ephx5) 110499548 110522278 110529658
OGO : 123990800 123995128 124040433(ephx5)
ONE : 115107806 115118720 115139362 115144473
OKI : 109866501 109870261 109870264 109900267
OKE : 118357678 118386954 118397798 118402703(ephx5)
SALP : 111954385 111973113
SNH : 120019006 120024146 120029362 120029363 120029925 120029926
CCLU : 121547755(ephx5) 121548868 121552613
AANG : 118217958(ephx5) 118230719(ephx1)
LOC : 102682886(ephx1) 102687913
PSPA : 121315717 121315718
ARUT : 117402351(ephx5) 117402598
BFO : 118403733 118403746 118404497 118404498 118404531 118418327
BBEL : 109476326 109476397
ARUN : 117300781 117300797 117300816 117307114
AJC : 117103745 117114357 117116249
PCHN : 125032423 125032480 125032492
PMOO : 119596527 119596966
DPTE : 113797953 113798526
ABRU : 129961830 129972631
LPOL : 106458781 106473233 106477280
PMEO : 129585230 129589033 129591709 129591716
CEL : CELE_W01A11.1(W01A11.1)
AMIL : 114972824 114974329
NTE : NEUTE1DRAFT122640(NEUTE1DRAFT_122640)
SMP : 10802655(SMAC4_04550)
PAN : PODANSg1577 PODANSg2534
PPSD : QC762_001380 QC762_700510
PPSP : QC763_001380 QC763_700510
PPSA : QC764_001380 QC764_700510
FPOA : FPOAC1_001873 FPOAC1_006228 FPOAC1_013440
FVN : FVRRES_02107 FVRRES_06832
NHE : NECHADRAFT_45915 NECHADRAFT_53192
FFC : NCS54_00980200 NCS54_01394900
FKR : NCS57_00503200 NCS57_01376900
FMU : J7337_007667 J7337_013713
TATV : 25775213(TrAtP1_008766) 25784646(TrAtP1_010175) 25784909(TrAtP1_000276)
TASP : 36609288(TrAFT101_011057) 36610727(TrAFT101_002074) 36611755(TrAFT101_002671)
MBRN : 26246650(G6M90_00g067860)
CLUP : CLUP02_04735 CLUP02_07353
CHIG : CH63R_03746 CH63R_06191 CH63R_09604
CDET : 87938675(CDEST_02172) 87940776(CDEST_04273) 87946027(CDEST_09524) 87949185(CDEST_12685)
GLZ : GLAREA_08702 GLAREA_12516
AFM : AFUA_2G14860 AFUA_3G08960
ANG : An12g08930 An16g02170(hyl1)
ALUC : AKAW2_61223A AKAW2_70182A
APUU : APUU_30512A APUU_60886A
TMF : EYB26_001367 EYB26_001374
TRG : TRUGW13939_03191 TRUGW13939_06026
PTRR : 6342899(PtrM4_115840) 6348645(PtrM4_076820)
AALT : CC77DRAFT_1022077 CC77DRAFT_801013
ARAB : EKO05_0003744 EKO05_0007025
FFU : CLAFUR5_02648 CLAFUR5_03954 CLAFUR5_04468 CLAFUR5_14183
CBET : CB0940_02999 CB0940_03071 CB0940_11798 CB0940_12212
KMG : 30160928(I203_105297)
CCAC : CcaHIS019_0301030(CcaverHIS019_0301030)
SGRA : EX895_004028 EX895_004254
» show all
Taxonomy
Reference
Authors
Oesch F, Daly J.
Title
Solubilization, purification, and properties of a hepatic epoxide hydrase.
Journal
Reference
2
Authors
Jakoby WB, Fjellstedt TA.
Title
Epoxidases.
Journal
In: Boyer PD (ed). The Enzymes. 3rd ed. Vol. 7. New York: Academic Press; 1972. p. 199-212.
Reference
Authors
Oesch F.
Title
Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds.
Journal
Reference
Authors
Oesch F.
Title
Purification and specificity of a human microsomal epoxide hydratase.
Journal
Reference
Authors
Lu AY, Ryan D, Jerina DM, Daly JW, Levin W.
Title
Liver microsomal expoxide hydrase. Solubilization, purification, and characterization.
Journal
J Biol Chem 250:8283-8 (1975)
Reference
Authors
Bellucci G, Chiappe C, Ingrosso G.
Title
Kinetics and stereochemistry of the microsomal epoxide hydrolase-catalyzed hydrolysis of cis-stilbene oxides.
Journal
Reference
Authors
Fretland AJ, Omiecinski CJ.
Title
Epoxide hydrolases: biochemistry and molecular biology.
Journal
Reference
Authors
Morisseau C, Hammock BD.
Title
Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles.
Journal
Reference
Authors
Newman JW, Morisseau C, Hammock BD.
Title
Epoxide hydrolases: their roles and interactions with lipid metabolism.
Journal
Reference
Authors
Toselli F, Fredenwall M, Svensson P, Li XQ, Johansson A, Weidolf L, Hayes MA
Title
Oxetane Substrates of Human Microsomal Epoxide Hydrolase.
Journal
Other DBs
ExplorEnz - The Enzyme Database: 3.3.2.9
ExPASy - ENZYME nomenclature database: 3.3.2.9
BRENDA, the Enzyme Database: 3.3.2.9