3.3.2.9 (3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O - Homo sapiens (3-[4-[([[3-(hydroxymethyl)oxetan-3-yl]methyl]amino)methyl]phenoxy]azetidin-1-yl)[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone - ? 434938 3.3.2.9 (3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O - Homo sapiens ? - ? 434939 3.3.2.9 (3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O - Homo sapiens [3-(4-[[3,3-bis(hydroxymethyl)azetidin-1-yl]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone - ? 434940 3.3.2.9 (5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O - Mus musculus (5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid - ? 410671 3.3.2.9 (5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O - Mus musculus C57BL/6 (5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid - ? 410671 3.3.2.9 (5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O - Oryctolagus cuniculus (5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid - ? 403050 3.3.2.9 (5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O - Mus musculus (5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid - ? 410672 3.3.2.9 (5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O - Mus musculus C57BL/6 (5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid - ? 410672 3.3.2.9 (5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O - Mus musculus (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid - ? 410673 3.3.2.9 (5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O - Mus musculus C57BL/6 (5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid - ? 410673 3.3.2.9 (8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O - Mus musculus (8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid - ? 410675 3.3.2.9 (8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O - Mus musculus C57BL/6 (8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid - ? 410675 3.3.2.9 (exo)-2,3-epoxynorbornane + H2O - Rattus norvegicus ? - ? 140218 3.3.2.9 (R)-1,2-epoxybutane + H2O very limited preference for hydrolysis of the (R)-enantiomer Phanerodontia chrysosporium (2R)-butane-1,2-diol - ? 440444 3.3.2.9 (R)-1,2-epoxyhexane + H2O - Rhodotorula glutinis n-2-hydroxyhexanol - ? 371384 3.3.2.9 (R)-epichlorhydrin + H2O very limited preference for hydrolysis of the (S)-enantiomer Phanerodontia chrysosporium (R)-3-chloro-1,2-propanediol - ? 440450 3.3.2.9 (R)-glycidyl tosylate + H2O very limited preference for hydrolysis of the (R)-enantiomer Phanerodontia chrysosporium (2R)-4-(4-methylbenzene-1-sulfonyl)butane-1,2,4-triol - ? 440451 3.3.2.9 (R)-styrene oxide + H2O - Rhodotorula glutinis (1R)-1-phenylethane-1,2-diol - ? 371394 3.3.2.9 (R)-styrene oxide + H2O - Homo sapiens (1R)-1-phenylethane-1,2-diol - ? 371394 3.3.2.9 (R)-styrene oxide + H2O - Mus musculus (1R)-1-phenylethane-1,2-diol - ? 371394 3.3.2.9 (R)-styrene oxide + H2O R-enantiomer is preferred Mugil cephalus (1R)-1-phenylethane-1,2-diol - ? 371394 3.3.2.9 (R)-styrene oxide + H2O preferential hydrolysis of the (R)-enantiomer Phanerodontia chrysosporium (R)-styrene glycol - ? 430817 3.3.2.9 (S)-1,2-epoxybutane + H2O very limited preference for hydrolysis of the (R)-enantiomer Phanerodontia chrysosporium (2S)-butane-1,2-diol - ? 440454 3.3.2.9 (S)-1,2-epoxyhexane + H2O - Rhodotorula glutinis n-2-hydroxyhexanol - ? 371402 3.3.2.9 (S)-epichlorhydrin + H2O very limited preference for hydrolysis of the (S)-enantiomer Phanerodontia chrysosporium (S)-3-chloro-1,2-propanediol - ? 440460 3.3.2.9 (S)-glycidyl tosylate + H2O very limited preference for hydrolysis of the (R)-enantiomer Phanerodontia chrysosporium (2S)-4-(4-methylbenzene-1-sulfonyl)butane-1,2,4-triol - ? 440461 3.3.2.9 (S)-styrene oxide + H2O - Rhodotorula glutinis 1,2-diphenylethane-1,2-diol - ? 371424 3.3.2.9 1,10-phenanthroline 5,6-oxide + H2O - Rattus norvegicus ? - ? 140191 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Cavia porcellus ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Mus musculus ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Rattus norvegicus ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Sus scrofa ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Oryctolagus cuniculus ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Pigeon ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - Felis catus ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - toad ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - trout ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O - quail ? - ? 140140 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O excellent and selective substrate for mEH Mus musculus 1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6,7-diol - ? 403163 3.3.2.9 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O excellent and selective substrate for mEH Homo sapiens 1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6,7-diol - ? 403163 3.3.2.9 1,2-epoxybutane + H2O - Rattus norvegicus 2-hydroxy-n-butanol - ? 140201 3.3.2.9 1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O - Homo sapiens 2-([[(4-methoxyphenyl)methyl](methyl)amino]methyl)-2-methylpropane-1,3-diol - ir 449137 3.3.2.9 1-methyl-1-phenyloxirane + H2O - Homo sapiens ? - ? 140173 3.3.2.9 11,12-epoxyeicosatrienoate + H2O - Homo sapiens 11,12-hydroxyeicosatrienoate - ? 449163 3.3.2.9 14,15-epoxyeicosatrienoic acid + H2O - Homalodisca vitripennis ? - ? 431277 3.3.2.9 16,17-epoxyandrost-4-en-3-one + H2O high activity Mus musculus 16,17-dihydroxyandrost-4-en-3-one - ? 378413 3.3.2.9 16,17-epoxyandrost-4-en-3-one + H2O high activity Homo sapiens 16,17-dihydroxyandrost-4-en-3-one - ? 378413 3.3.2.9 16,17-epoxyandrost-4-en-3-one + H2O high activity Rattus norvegicus 16,17-dihydroxyandrost-4-en-3-one - ? 378413 3.3.2.9 16alpha,17alpha-epoxyandrosten-3-one + H2O endogenous substrate of mEH Mus musculus ? - ? 403309 3.3.2.9 16alpha,17alpha-epoxyandrosten-3-one + H2O endogenous substrate of mEH Homo sapiens ? - ? 403309 3.3.2.9 2,3-epoxypropyl ether + H2O - Cavia porcellus ? - ? 140165 3.3.2.9 2,3-epoxypropyl-p-methoxyphenyl ether + H2O - Rattus norvegicus ? - ? 140185 3.3.2.9 2,3-epoxypropyl-p-methoxyphenyl ether + H2O - Rattus norvegicus 3-(3-methoxyphenoxy)propane-1,2-diol - ? 140213 3.3.2.9 2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine + H2O - Homo sapiens 2-([[2-(4-methoxyphenyl)ethyl](methyl)amino]methyl)-2-methylpropane-1,3-diol - ir 449196 3.3.2.9 2-arachidonoylglycerol + H2O - Homo sapiens arachidonic acid + glycerol - ? 364031 3.3.2.9 2-bromoethylene oxide + H2O - Rattus norvegicus ? - ? 140212 3.3.2.9 2-chloroethylene oxide + H2O - Homo sapiens ? - ? 140186 3.3.2.9 2-chloroethylene oxide + H2O - Rattus norvegicus ? - ? 140186 3.3.2.9 3,3,3-trichloropropylene oxide + H2O - Rattus norvegicus ? - ? 140183 3.3.2.9 3-methylcholanthrene 11,12-oxide + H2O - Homo sapiens ? - ? 140179 3.3.2.9 3-methylcholanthrene 11,12-oxide + H2O - Rattus norvegicus ? - ? 140179 3.3.2.9 4-chlorophenyl 2,3-epoxypropyl ether + H2O - Cavia porcellus ? - ? 140164 3.3.2.9 4-chlorophenyl 2,3-epoxypropyl ether + H2O - Rattus norvegicus ? - ? 140164 3.3.2.9 4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate + H2O - Homo sapiens ? - ? 416317 3.3.2.9 4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate + H2O - Rattus norvegicus ? - ? 416317 3.3.2.9 4-nitrophenyl 3-(oxiran-2-yl)propanoate + H2O - Homo sapiens ? - ? 416357 3.3.2.9 4-nitrophenyl 3-(oxiran-2-yl)propanoate + H2O - Rattus norvegicus ? - ? 416357 3.3.2.9 4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate + H2O - Homo sapiens ? - ? 416362 3.3.2.9 4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate + H2O - Rattus norvegicus ? - ? 416362 3.3.2.9 4-nitrostyrene 7,8-oxide + H2O i.e. PNSO Homo sapiens 1-(4-nitro)phenyl-ethane-1,2-diol - ? 379056 3.3.2.9 4-vinylcyclohexene + H2O - Rattus norvegicus ? - ? 416424 3.3.2.9 4-vinylcyclohexene diepoxide + H2O - Mus musculus 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane - ? 403976 3.3.2.9 4-vinylcyclohexene diepoxide + H2O - Rattus norvegicus 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane - ? 403976 3.3.2.9 4-vinylcyclohexene diepoxide + H2O - Mus musculus 129S1/SvImJ 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane - ? 403976 3.3.2.9 4-vinylcyclohexene diepoxide + H2O - Rattus norvegicus Fischer 344 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane - ? 403976 3.3.2.9 4-vinylcyclohexene dioxide + H2O low activity Rattus norvegicus ? - ? 140217 3.3.2.9 7,12-dimethylbenz[a]anthracene + 3 H2O - Rattus norvegicus 7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide - ? 416461 3.3.2.9 7,12-dimethylbenz[a]anthracene + 3 H2O - Mus musculus 7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide - ? 416461 3.3.2.9 7,12-dimethylbenz[a]anthracene + 3 H2O - Mus musculus 7,12-dimethylbenz[a]anthra-3,4-diol-1,2-epoxide - ? 448398 3.3.2.9 7,12-dimethylbenz[a]anthracene + H2O - Homo sapiens ? - ? 431440 3.3.2.9 7-glycidoxycoumarin + H2O - Canis lupus familiaris ? - ? 140205 3.3.2.9 7-glycidoxycoumarin + H2O substrate is a stable epoxide Mus musculus 7-(1',2'-dihydroxy-3'-propoxy)coumarin - ? 379082 3.3.2.9 7-methylbenzanthracene-5,6-oxide + H2O - Rattus norvegicus ? - ? 140181 3.3.2.9 7-methylbenzoanthracene + H2O - Rattus norvegicus ? - ? 140180 3.3.2.9 aflatoxin-B1-8,9-exo-epoxide + H2O - Mus musculus ? - ? 404242 3.3.2.9 aflatoxin-B1-8,9-exo-epoxide + H2O - Homo sapiens ? - ? 404242 3.3.2.9 allylbenzene + H2O - Cavia porcellus 3-phenylpropane-1,2-diol - ? 379172 3.3.2.9 allylbenzene + H2O - Mus musculus 3-phenylpropane-1,2-diol - ? 379172 3.3.2.9 allylbenzene + H2O - Rattus norvegicus 3-phenylpropane-1,2-diol - ? 379172 3.3.2.9 androstene oxide + H2O - Homo sapiens ? - ? 140143 3.3.2.9 androstene oxide + H2O - Rattus norvegicus ? - ? 140143 3.3.2.9 androstene oxide + H2O - Homo sapiens androstene diol - ? 449565 3.3.2.9 benzene + H2O - Homo sapiens ? - ? 449633 3.3.2.9 benzene oxide + H2O - Rattus norvegicus ? - ? 140141 3.3.2.9 benzo(a)pyrene 4,5-oxide + H2O - Homo sapiens ? - ? 431648 3.3.2.9 benzoanthracene 5,6-oxide + H2O - Homo sapiens ? - ? 140134 3.3.2.9 benzoanthracene 5,6-oxide + H2O - Rattus norvegicus ? - ? 140134 3.3.2.9 benzoanthracene-9,10-oxide + H2O - Rattus norvegicus ? - ? 140138 3.3.2.9 benzopyrene 11,12-oxide + H2O - Rattus norvegicus ? - ? 140132 3.3.2.9 benzopyrene 4,5-oxide + H2O - Cavia porcellus (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Mus musculus (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Homo sapiens (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Rattus norvegicus (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Sus scrofa (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Oryctolagus cuniculus (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Pigeon (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - Felis catus (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - toad (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - trout (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 4,5-oxide + H2O - quail (-)benzopyrene 4,5-dihydrodiol - ? 140129 3.3.2.9 benzopyrene 7,8-oxide + H2O - Homo sapiens ? - ? 140130 3.3.2.9 benzopyrene 7,8-oxide + H2O - Rattus norvegicus ? - ? 140130 3.3.2.9 benzopyrene 9,10-oxide + H2O - Rattus norvegicus ? - ? 140131 3.3.2.9 benzo[a]pyrene 5-oxide + H2O - Homo sapiens ? - ? 404477 3.3.2.9 benzo[a]pyrene 5-oxide + H2O - Rattus norvegicus ? - ? 404477 3.3.2.9 benzo[a]pyrene 7,8-oxide + H2O - Homo sapiens benzo[a]pyrene 7,8-diol - ? 449642 3.3.2.9 benzo[a]pyrene-7,8-epoxide + H2O - Mus musculus benzo[a]pyrene-7,8-dihydrodiol - ? 404478 3.3.2.9 benzo[a]pyrene-7,8-epoxide + H2O - Homo sapiens benzo[a]pyrene-7,8-dihydrodiol - ? 404478 3.3.2.9 benz[a]anthracene 5,6-oxide + H2O - Rattus norvegicus 5,6-dihydro-chrysene-5,6-diol - ? 379545 3.3.2.9 benz[a]pyrene 4,5-oxide + H2O - Homo sapiens 4,5-dihydro-benzo[def]chrysene-4,5-diol - ? 379546 3.3.2.9 bisnorsqualene oxide + H2O - Cavia porcellus ? - ? 140168 3.3.2.9 butadiene + H2O - Homo sapiens butadienol - ? 449718 3.3.2.9 butadiene monoxide + H2O low activity Rattus norvegicus ? - ? 140215 3.3.2.9 carbamazepine-10,11-epoxide + H2O - Mus musculus ? - ? 404591 3.3.2.9 carbamazepine-10,11-epoxide + H2O - Homo sapiens ? - ? 404591 3.3.2.9 cis-8-ethylstyrene 7,8-oxide + H2O - Homo sapiens ? - ? 140207 3.3.2.9 cis-stilbene oxide + H2O - Cavia porcellus ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Mus musculus ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Homo sapiens ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Rattus norvegicus ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Oryctolagus cuniculus ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Macaca mulatta ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Cricetinae ? - ? 140145 3.3.2.9 cis-stilbene oxide + H2O - Drosophila melanogaster 1,2-diphenylethane-1,2-diol - ? 372734 3.3.2.9 cis-stilbene oxide + H2O - Mus musculus (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Homo sapiens (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Rattus norvegicus (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Oryctolagus cuniculus (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Macaca mulatta (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Homalodisca vitripennis (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Heliothis virescens (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O the recombinant enzyme expressed in Escherichia coli acts stereospecifically on the the (R)-styrene Danio rerio (+)-(1R,2R)-1,2-diphenylethane-1,2-diol - ? 378653 3.3.2.9 cis-stilbene oxide + H2O - Mus musculus (1R,2R)-1,2-diphenylethane-1,2-diol - ? 379602 3.3.2.9 cis-stilbene oxide + H2O - Homo sapiens (1R,2R)-1,2-diphenylethane-1,2-diol - ? 379602 3.3.2.9 cis-stilbene oxide + H2O - Rattus norvegicus (1R,2R)-1,2-diphenylethane-1,2-diol - ? 379602 3.3.2.9 cis-stilbene oxide + H2O - Mus musculus B6C3F1 (1R,2R)-1,2-diphenylethane-1,2-diol - ? 379602 3.3.2.9 cis-stilbene oxide + H2O - Mus musculus 129S1/SvImJ (1R,2R)-1,2-diphenylethane-1,2-diol - ? 379602 3.3.2.9 clofibrate + H2O - Mus musculus ? - ? 140162 3.3.2.9 clofibrate + H2O - Homo sapiens ? - ? 140162 3.3.2.9 clofibrate + H2O - Rattus norvegicus ? - ? 140162 3.3.2.9 clofibrate + H2O - Oryctolagus cuniculus ? - ? 140162 3.3.2.9 clofibrate + H2O - Macaca mulatta ? - ? 140162 3.3.2.9 cyano(2-methoxynaphthalen-6-yl)methyl trans-(2-(3-phenyloxiran-2-yl))acetate + H2O - Heliothis virescens ? - ? 431747 3.3.2.9 cyano(2-methoxynaphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl)acetate + H2O - Heliothis virescens ? - ? 431749 3.3.2.9 cyano(2-methoxynaphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl)acetate + H2O - Karenia brevis ? - ? 431749 3.3.2.9 cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O synthetic fluorescent substrate Homo sapiens ? - ? 416803 3.3.2.9 cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O synthetic fluorescent substrate Rattus norvegicus ? - ? 416803 3.3.2.9 cyano(6-methoxy-naphthalen-2-yl)methyl oxiran-2-ylmethyl carbonate + H2O - Heliothis virescens ? - ? 431750 3.3.2.9 cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl]carbonate + H2O - Heliothis virescens ? - ? 431751 3.3.2.9 cyano-(6-methoxy-naphthalen-2-yl)-methyl 3,3-dimethyl-oxiranylmethyl carbonate + H2O - Heliothis virescens ? - ? 431753 3.3.2.9 cyano-(6-methoxy-naphthalen-2-yl)-methyl trans-((3-ethyl-oxiran-2-yl)methyl) carbonate + H2O - Heliothis virescens ? - ? 431754 3.3.2.9 cyano-(6-methoxynaphthalen-2-yl)methyl trans-2-pentenylacetate + H2O prepared from trans-styrylacetic acid and 7-methoxy-2-naphthaldehyde. Enzyme EH catalyzed hydrolysis of the epoxide substrate produces an intermediate diol which lactonizes to release a fluorescent reporter after hydrolysis of the intermediate cyanohydrin Karenia brevis ? - ? 449790 3.3.2.9 cyclododecene-1,2-oxide + H2O - Rattus norvegicus ? - ? 140177 3.3.2.9 cyclohexene + H2O - Homo sapiens cyclohexadiol - ? 449795 3.3.2.9 cyclohexene oxide + H2O - Homo sapiens ? - ? 140175 3.3.2.9 cyclohexene-1,2-oxide + H2O - Rattus norvegicus ? - ? 140176 3.3.2.9 cytochrome P450 isoform 1B1 + H2O - Mus musculus 7,12-dimethylbenz(a)anthracene-3,4-diol - ? 404755 3.3.2.9 cytochrome P450 isoform 1B1 + H2O - Mus musculus 129S1/SvImJ 7,12-dimethylbenz(a)anthracene-3,4-diol - ? 404755 3.3.2.9 di(2-ethylhexyl)phthalate + H2O - Mus musculus ? - ? 140163 3.3.2.9 di(2-ethylhexyl)phthalate + H2O - Homo sapiens ? - ? 140163 3.3.2.9 di(2-ethylhexyl)phthalate + H2O - Rattus norvegicus ? - ? 140163 3.3.2.9 di(2-ethylhexyl)phthalate + H2O - Oryctolagus cuniculus ? - ? 140163 3.3.2.9 di(2-ethylhexyl)phthalate + H2O - Macaca mulatta ? - ? 140163 3.3.2.9 dibenzanthracene 5,6-oxide + H2O - Homo sapiens ? - ? 140136 3.3.2.9 dibenzanthracene 5,6-oxide + H2O - Rattus norvegicus ? - ? 140136 3.3.2.9 dibenzoanthracene + H2O - Rattus norvegicus ? - ? 140135 3.3.2.9 dl-1,3-butadiene diepoxide + H2O low activity Rattus norvegicus ? - ? 140216 3.3.2.9 epibromhydrin + H2O - Rattus norvegicus ? - ? 140196 3.3.2.9 epichlorhydrin + H2O - Rattus norvegicus 3-chloro-1,2-propanediol - ? 140195 3.3.2.9 epifluorohydrin + H2O - Rattus norvegicus ? - ? 140197 3.3.2.9 epoxy-stearic acid + H2O highly enantiospecific reaction, low activity Homo sapiens ? - ? 379721 3.3.2.9 epoxyestratrienol + H2O - Homo sapiens ? - ? 448567 3.3.2.9 epoxyestratrienol + H2O - Homo sapiens dihydroxyestratrienol - ? 449896 3.3.2.9 estroxide + H2O - Homo sapiens ? - ? 140142 3.3.2.9 estroxide + H2O - Rattus norvegicus ? - ? 140142 3.3.2.9 estroxide + H2O 16alpha,17alpha-epoxyestratrienol Rattus norvegicus ? - ? 140142 3.3.2.9 ethylene oxide + H2O - Mus musculus ethane-1,2-diol - ? 405100 3.3.2.9 ethylene oxide + H2O - Homo sapiens ethane-1,2-diol - ? 405100 3.3.2.9 ethylene oxide + H2O - Homo sapiens ethylene glycol - ? 449902 3.3.2.9 glycidyl methacrylate + H2O low activity Rattus norvegicus ? - ? 140184 3.3.2.9 indene 1,2-oxide + H2O - Homo sapiens ? - ? 140174 3.3.2.9 indene-1,2-oxide + H2O - Cavia porcellus ? - ? 140167 3.3.2.9 juvenile hormone I + H2O - Manduca sexta ? - ? 140209 3.3.2.9 juvenile hormone II + H2O - Manduca sexta ? - ? 140210 3.3.2.9 juvenile hormone III + H2O - Manduca sexta ? - ? 140211 3.3.2.9 juvenile hormone III + H2O - Tribolium castaneum ? - ? 140211 3.3.2.9 juvenile hormone III + H2O - Homalodisca vitripennis ? - ? 140211 3.3.2.9 juvenile hormone III + H2O poor substrate Heliothis virescens ? - ? 140211 3.3.2.9 additional information - Cavia porcellus ? - ? 89 3.3.2.9 additional information - Mus musculus ? - ? 89 3.3.2.9 additional information - Homo sapiens ? - ? 89 3.3.2.9 additional information - Rattus norvegicus ? - ? 89 3.3.2.9 additional information substrate specificity Homo sapiens ? - ? 89 3.3.2.9 additional information enzyme is induced by a number of xenobiotics, the enzyme is thought to play a detoxifying role by preventing epoxides from reacting irreversibly with critical cellular macromolecules. Some evidence exists to support the hypothesis that microsomal epoxide hydrolase is closely associated with at least certain forms of cytochrome P-450, such association may influence the functional role of the microsomal epoxide hydrolase in the various pathways of bioactivation Cavia porcellus ? - ? 89 3.3.2.9 additional information enzyme is induced by a number of xenobiotics, the enzyme is thought to play a detoxifying role by preventing epoxides from reacting irreversibly with critical cellular macromolecules. Some evidence exists to support the hypothesis that microsomal epoxide hydrolase is closely associated with at least certain forms of cytochrome P-450, such association may influence the functional role of the microsomal epoxide hydrolase in the various pathways of bioactivation Mus musculus ? - ? 89 3.3.2.9 additional information enzyme is induced by a number of xenobiotics, the enzyme is thought to play a detoxifying role by preventing epoxides from reacting irreversibly with critical cellular macromolecules. Some evidence exists to support the hypothesis that microsomal epoxide hydrolase is closely associated with at least certain forms of cytochrome P-450, such association may influence the functional role of the microsomal epoxide hydrolase in the various pathways of bioactivation Homo sapiens ? - ? 89 3.3.2.9 additional information enzyme is induced by a number of xenobiotics, the enzyme is thought to play a detoxifying role by preventing epoxides from reacting irreversibly with critical cellular macromolecules. Some evidence exists to support the hypothesis that microsomal epoxide hydrolase is closely associated with at least certain forms of cytochrome P-450, such association may influence the functional role of the microsomal epoxide hydrolase in the various pathways of bioactivation Rattus norvegicus ? - ? 89 3.3.2.9 additional information the enzyme may play a significant role in the secondary metabolism of juvenile hormone acid generated by juvenile hormone esterase Manduca sexta ? - ? 89 3.3.2.9 additional information the enzyme plays an important role in the metabolism of various xenobiotic compounds including the polycyclic aromatic hydrocarbon carcinogens. It is specifically involved in the formation of the ultimate carcinogen of benzopyrene Mus musculus ? - ? 89 3.3.2.9 additional information induced about threefold by 5 mM phenobarbital Trypanosoma cruzi ? - ? 89 3.3.2.9 additional information involved in the biotransformation of epoxides produced from either xeno- or endobiotics. The diols produced are generally detoxification products but in several instances, such as 9,10-epoxybenzopyrene-7,8-diol, they are very potent mutagens and possible carcinogens. The enzyme is induced by phenobarbital Homo sapiens ? - ? 89 3.3.2.9 additional information the enzyme is expected to play a purely protective role with respect to epoxides metabolically produced from pharmaceutical drugs Homo sapiens ? - ? 89 3.3.2.9 additional information role in benzopyrene-induced mutagenesis and carcinogenesis Rattus norvegicus ? - ? 89 3.3.2.9 additional information enzyme is involved in the metabolism of steroids, the microsomal enzyme plays a central role in both the inactivation of primary mutagenic and carcinogenic metabolites of polycyclic aromatic hydrocarbons, and in activating these metabolites to even more toxic or mutagenic secondary products, enzyme production is induced by 3-methylcholanthrene, phenobarbital, trans-stilbene oxide, 2(3)-tert-butyl-4-hydroxyanisol or 2-acetylaminofluorene Rattus norvegicus ? - ? 89 3.3.2.9 additional information potent and selective induction by trans-stilbene oxide Rattus norvegicus ? - ? 89 3.3.2.9 additional information probably represents an important factor in the control of reactive epoxides Mus musculus ? - ? 89 3.3.2.9 additional information the enzyme in Drosophila melanogaster is involved in xenobiotic biotransformation, but not in juvenile hormone metabolism Drosophila melanogaster ? - ? 89 3.3.2.9 additional information genetic polymorphisms of the enzyme are responsible for varying susceptibility of cigarette smoking humans to chronic obstructive pulmonary disease, COPD Homo sapiens ? - ? 89 3.3.2.9 additional information key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level, the enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport, the enzyme is part of a multi-transport system at the cell surface Homo sapiens ? - ? 89 3.3.2.9 additional information key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level. The enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport. The enzyme is part of a multi-transport system at the cell surface Mus musculus ? - ? 89 3.3.2.9 additional information the enzyme activity in diabetic and in fasted rats is reduced by 60-71%, key enzyme in the metabolism of environmental contaminants being responsible for xenobiotic transformations, regulation of the enzyme occurs at transcriptional, translational, and post-translational level, the enzyme is also involved in cytoprotection and steroid metabolism, as well as in cellular responses to glucose metabolism and in Na+-dependent bile acid transport, the enzyme is part of a multi-transport system at the cell surface Rattus norvegicus ? - ? 89 3.3.2.9 additional information the enzyme is a phase II biotransformation enzyme which detoxifies epoxides, including carcinogens such as polycyclic aromatic hydrocarbons found in cigarette smoke and cooked meats, enzyme polymorphisms are not associated with colon cancer risk Homo sapiens ? - ? 89 3.3.2.9 additional information the enzyme is critical for biotransformations in xenobiotic metabolism and detoxification Homo sapiens ? - ? 89 3.3.2.9 additional information the enzyme is critical for biotransformations in xenobiotic metabolism and detoxification Rattus norvegicus ? - ? 89 3.3.2.9 additional information the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide Rattus norvegicus ? - ? 89 3.3.2.9 additional information the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide, enzyme deficiency leads to acute and severe phenytoin toxicity in vivo, the enzyme is involved in transport of bile acids in the liver Homo sapiens ? - ? 89 3.3.2.9 additional information the enzyme is involved in xenobiotic metabolism and detoxification, e.g. of 1,3-butadiene oxide, styrene oxide, and benzo[a]pyrene-4,5-oxide, the enzyme is important in sexual development Mus musculus ? - ? 89 3.3.2.9 additional information the enzyme metabolizes xenobiotic epoxides Rattus norvegicus ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Rattus norvegicus ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Triticum aestivum ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Zea mays ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Solanum tuberosum ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Nicotiana tabacum ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Glycine max ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Apium graveolens ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Oryza sativa ? - ? 89 3.3.2.9 additional information enantioselectivity with fatty acid epoxide substrates Musa x paradisiaca ? - ? 89 3.3.2.9 additional information mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids Homo sapiens ? - ? 89 3.3.2.9 additional information mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids, the enzyme acts as an antiestrogen binding site subunit Mus musculus ? - ? 89 3.3.2.9 additional information mEH prefers mono- and cis-substituted epoxides, low but highly enantioselective activity with epoxy fatty acids, the enzyme acts as an antiestrogen binding site subunit Rattus norvegicus ? - ? 89 3.3.2.9 additional information no activity with 5,6alpha-epoxy-5alpha-cholestan-3beta-ol and 5,6beta-epoxy-5alpha-cholestan-3beta-ol Rattus norvegicus ? - ? 89 3.3.2.9 additional information substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic systems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-valus, fatty acid and ester epoxides are hydrated very quickly Macaca mulatta ? - ? 89 3.3.2.9 additional information substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic sytems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-values, fatty acid and ester epoxides are hydrated very quickly Mus musculus ? - ? 89 3.3.2.9 additional information substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic sytems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-values, fatty acid and ester epoxides are hydrated very quickly Homo sapiens ? - ? 89 3.3.2.9 additional information substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic sytems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-values, fatty acid and ester epoxides are hydrated very quickly Rattus norvegicus ? - ? 89 3.3.2.9 additional information substrate specificity, no activity with 1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene,i.e. HEOM, 2-acetylaminofluorene, arochlor 1254, and benzopyrene 4,5-oxide, the cytosolic enzyme hydrates epoxides on cyclic sytems very slowly, but hydrates a wide variety of aliphatic epoxides rapidly, trisubstituted terpenoid epoxides show low Km-values, fatty acid and ester epoxides are hydrated very quickly Oryctolagus cuniculus ? - ? 89 3.3.2.9 additional information the enzyme is distinct from the microsomal epoxide hydrolase EC 3.3.2.11, which specifically utilizes 5,6alpha-epoxy-5alpha-cholestan-3beta-ol, that is no substrate for EC 3.3.2.9 Rattus norvegicus ? - ? 89 3.3.2.9 additional information the enzyme shows a broad substrate specificity, all epoxides with a trisubstituted oxirane ring are no or poor substrates, no activity with 5,6alpha-epoxy-5alpha-cholestan-3beta-ol Rattus norvegicus ? - ? 89 3.3.2.9 additional information the enzyme shows a broad substrate specificity, all epoxides with a trisubstituted oxirane ring are no or poor substrates, no activity with 5,6alpha-epoxy-5alpha-cholestan-3beta-ol Oryctolagus cuniculus ? - ? 89 3.3.2.9 additional information wide substrate specificity, epoxide-containing glycerol-phospholipids are poor substrates, the enzyme prefers mono- and cis-1,2-disubstituted epoxides as substrates, while gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors, the enzyme has a tamaoxifen binding site Homo sapiens ? - ? 89 3.3.2.9 additional information wide substrate specificity, the enzyme prefers mono- and cis-1,2-disubstituted epoxides as substrates, while gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors Mus musculus ? - ? 89 3.3.2.9 additional information wide substrate specificity, the enzyme prefers mono- and cis-1,2-disubstituted epoxides as substrates, while gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors Rattus norvegicus ? - ? 89 3.3.2.9 additional information EPHX1 detoxifies genotoxic compounds and participates in the removal of reactive oxygen species Homo sapiens ? - ? 89 3.3.2.9 additional information mEH is capable of inactivating a large number of structurally different, highly reactive epoxides and hence is an important part of the enzymatic defence of our organism against adverse effects of foreign compounds Mus musculus ? - ? 89 3.3.2.9 additional information mEH is capable of inactivating a large number of structurally different, highly reactive epoxides and hence is an important part of the enzymatic defence of our organism against adverse effects of foreign compounds Homo sapiens ? - ? 89 3.3.2.9 additional information mEH mediates the transport of bile acid in the liver Mus musculus ? - ? 89 3.3.2.9 additional information mEH mediates the transport of bile acid in the liver Homo sapiens ? - ? 89 3.3.2.9 additional information mEH prefers mono- and cis-1,2-disubstituted epoxides, while gem-di-, trans-di-, tri- and tetrasubstituted epoxides are low-turnover substrates or inhibitors Mus musculus ? - ? 89 3.3.2.9 additional information mEH prefers mono- and cis-1,2-disubstituted epoxides, while gem-di-, trans-di-, tri- and tetrasubstituted epoxides are low-turnover substrates or inhibitors Homo sapiens ? - ? 89 3.3.2.9 additional information not active with trans-1,3-diphenylpropene oxide Rattus norvegicus ? - ? 89 3.3.2.9 additional information no activity with 14,15-epoxyexicosatrienoic acid Homo sapiens ? - ? 89 3.3.2.9 additional information no activity with trans-stilbene oxide Homalodisca vitripennis ? - ? 89 3.3.2.9 additional information the enzyme exhibits broad hydrolytic activity toward several racemic epoxides including styrene oxide, epichlorohydrin, and 1,2-epoxybutane Phanerodontia chrysosporium ? - ? 89 3.3.2.9 additional information enzyme mEH in collaboration with cytochrome-P-450 (CYP) converts benzo(a)pyrene to more reactive intermediate, benzo(a)pyrene-7,8-dihydrodiol 8,9-epoxide (benzo(a)pyrene diolepoxide, BPDE) which displays higher mutagenic and carcinogenic potential than its substrate Homo sapiens ? - ? 89 3.3.2.9 additional information oxetanes are a nonepoxide class of substrates for human mEH, which is known to catalyze the hydrolytic ring opening of electrophilic and potentially toxic epoxide-containing drugs, drug metabolites, and exogenous organochemicals Homo sapiens ? - ? 89 3.3.2.9 additional information stereoselective hydrolysis of epoxyeicosatrienoic acids (EETs) by sEH Oryctolagus cuniculus ? - ? 89 3.3.2.9 additional information the enzyme converts epoxides to diols and is able to either detoxify or bioactivate a wide range of substrates. The prototypical EPHX1 reaction involves conversion of epoxides to trans-dihydrodiols. EPHX1 more readily converts xenobiotics than endogenous substrates Homo sapiens ? - ? 89 3.3.2.9 additional information EPHX1 has a broad substrate specificity. It also metabolizes endocannabinoid 2-arachidonoylglycerol to free arachidonic acid and glycerol Homo sapiens ? - ? 89 3.3.2.9 additional information microsomal epoxide hydrolase (mEH) has a wide substrate specificity Mus musculus ? - ? 89 3.3.2.9 additional information microsomal epoxide hydrolase (mEH) has wide a substrate specificity Rattus norvegicus ? - ? 89 3.3.2.9 additional information no activity with [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[methyl(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(3-methyloxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone, 2-(4-methoxyphenyl)-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine, and 2-(4-methoxyphenyl)-N-methyl-N-[(oxetan-3-yl)methyl]ethan-1-amine Homo sapiens ? - ? 89 3.3.2.9 additional information the enzyme has the potential to catalyze the critical endo-tet cyclization of epoxy alcohols via a endo-tet cyclization, mechanism, overview. Reaction of polyepoxide pre-momensin to momensin, a polyether, or of another polyepoxide to brevetoxin B Karenia brevis ? - ? 89 3.3.2.9 additional information the microsomal epoxide hydrolase (EPHX1) is inactive with cis- or trans-allylic epoxides, such as 9R,10R-trans-epoxy-13R-hydroxy-octadeca-11E-enoic acid, 9R,10S-cis-epoxy-13R-hydroxyoctadeca-11E-enoic acid, 12,13-trans-epoxy-octadeca-9E-enoic acid, and 12,13-cis-epoxy-octadeca-9E-enoic acid, in contrast to the soluble epoxide hydrolase, (EPHX2 and EPHX3, EC 3.3.2.10) Homo sapiens ? - ? 89 3.3.2.9 additional information microsomal epoxide hydrolase (mEH) has wide a substrate specificity Rattus norvegicus Fischer 344 ? - ? 89 3.3.2.9 naphthalene 1,2-oxide + H2O - Homo sapiens naphthalene 1,2-diol - ? 380127 3.3.2.9 naphthalene-1,2-oxide + H2O - Cavia porcellus ? - ? 140171 3.3.2.9 naphthalene-1,2-oxide + H2O - Homo sapiens ? - ? 140171 3.3.2.9 naphthalene-1,2-oxide + H2O - Rattus norvegicus ? - ? 140171 3.3.2.9 octene 1,2-oxide + H2O - Homo sapiens ? - ? 140148 3.3.2.9 octene 1,2-oxide + H2O - Rattus norvegicus ? - ? 140148 3.3.2.9 octene 1,2-oxide + H2O - Rattus norvegicus octan-1,2-diol - ? 380168 3.3.2.9 octene-1,2-oxide + H2O - Cavia porcellus ? - ? 140166 3.3.2.9 okadaic acid + H2O - Karenia brevis ? - ? 450422 3.3.2.9 p-chlorophenyl-2,3-epoxypropylether + H2O - Rattus norvegicus ? - ? 140182 3.3.2.9 p-nitrostyrene 7,8-oxide + H2O - Homo sapiens ? - ? 140150 3.3.2.9 p-nitrostyrene 7,8-oxide + H2O - Rattus norvegicus ? - ? 140150 3.3.2.9 phenanthrene-9,10-oxide + H2O - Cavia porcellus ? - ? 140139 3.3.2.9 phenanthrene-9,10-oxide + H2O - Mus musculus ? - ? 140139 3.3.2.9 phenanthrene-9,10-oxide + H2O - Homo sapiens ? - ? 140139 3.3.2.9 phenanthrene-9,10-oxide + H2O - Rattus norvegicus ? - ? 140139 3.3.2.9 propylene oxide + H2O low activity Rattus norvegicus ? - ? 140199 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 30% enantioselective (9S,10S)-cis-diol production Apium graveolens threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 59% enantioselective (9S,10S)-cis-diol production Triticum aestivum threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 63.5% enantioselective (9S,10S)-cis-diol production Musa x paradisiaca threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 74% enantioselective (9S,10S)-cis-diol production Oryza sativa threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 90% enantioselective (9S,10S)-cis-diol production by the constitutive enzyme, 86% by the pathogen-induced enzyme Solanum tuberosum threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 94% enantioselective (9S,10S)-cis-diol production Nicotiana tabacum threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 racemic cis-9,10-epoxystearic acid + H2O 94% enantioselective (9S,10S)-cis-diol production Glycine max threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid - ? 380240 3.3.2.9 styrene + H2O - Homo sapiens ? - ? 450672 3.3.2.9 styrene 7,8-oxide + H2O - Homo sapiens styrene glycol - ? 140147 3.3.2.9 styrene 7,8-oxide + H2O - Rattus norvegicus styrene glycol - ? 140147 3.3.2.9 styrene 7,8-oxide + H2O - Homo sapiens 1-phenyl-ethane-1,2-diol - ? 380308 3.3.2.9 styrene 7,8-oxide + H2O - Rattus norvegicus 1-phenyl-ethane-1,2-diol - ? 380308 3.3.2.9 styrene epoxide + H2O - Rattus norvegicus 1-phenyl-ethane-1,2-diol - ? 380310 3.3.2.9 styrene oxide + H2O - Cavia porcellus styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Mus musculus styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Homo sapiens styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Rattus norvegicus styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Sus scrofa styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Oryctolagus cuniculus styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Pigeon styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Trypanosoma cruzi styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Felis catus styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - toad styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - trout styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - quail styrene glycol - ? 140146 3.3.2.9 styrene oxide + H2O - Cavia porcellus 1-phenylethane-1,2-diol - ? 380311 3.3.2.9 styrene oxide + H2O - Mus musculus 1-phenylethane-1,2-diol - ? 380311 3.3.2.9 styrene oxide + H2O - Homo sapiens 1-phenylethane-1,2-diol - ? 380311 3.3.2.9 styrene oxide + H2O - Rattus norvegicus 1-phenylethane-1,2-diol - ? 380311 3.3.2.9 styrene oxide + H2O recombinant enzyme, low activity Glycine max 1-phenylethane-1,2-diol - ? 380311 3.3.2.9 styrene oxide + H2O - Homo sapiens 1-phenyl-ethane-1,2-diol - ? 380312 3.3.2.9 styrene oxide + H2O - Rattus norvegicus 1-phenyl-ethane-1,2-diol - ? 380312 3.3.2.9 styrene oxide + H2O - Oryctolagus cuniculus 1-phenyl-ethane-1,2-diol - ? 380312 3.3.2.9 styrene oxide + H2O - Macaca mulatta 1-phenyl-ethane-1,2-diol - ? 380312 3.3.2.9 styrene-7,8-oxide + H2O - Mus musculus 1-phenylethane-1,2-diol - ? 406699 3.3.2.9 styrene-7,8-oxide + H2O - Homo sapiens 1-phenylethane-1,2-diol - ? 406699 3.3.2.9 trans-4,5-epoxy-hexanol exo-tet cyclization reaction Karenia brevis 1-(tetrahydrofuran-2-yl)ethanol - ? 450775 3.3.2.9 trans-4,5-epoxy-hexanol endo-tet cyclization reaction Karenia brevis 2-methyltetrahydro-2H-pyran-3-ol - ? 450776 3.3.2.9 trans-8-ethylstyrene 7,8-oxide + H2O i.e. TESO Homo sapiens ? - ? 140208 3.3.2.9 trans-9,10-epoxystearate + H2O - Mus musculus 9,10-dihydroxy-octadecanoic acid - ? 380351 3.3.2.9 trans-9,10-epoxystearate + H2O - Homo sapiens 9,10-dihydroxy-octadecanoic acid - ? 380351 3.3.2.9 trans-9,10-epoxystearate + H2O - Rattus norvegicus 9,10-dihydroxy-octadecanoic acid - ? 380351 3.3.2.9 trans-9,10-epoxystearate + H2O - Oryctolagus cuniculus 9,10-dihydroxy-octadecanoic acid - ? 380351 3.3.2.9 trans-9,10-epoxystearate + H2O - Macaca mulatta 9,10-dihydroxy-octadecanoic acid - ? 380351 3.3.2.9 trans-diphenylpropene oxide + H2O - Homalodisca vitripennis ? - ? 380355 3.3.2.9 trans-diphenylpropene oxide + H2O - Heliothis virescens ? - ? 380355 3.3.2.9 trans-ethyl styrene oxide + H2O - Mus musculus ? - ? 140157 3.3.2.9 trans-ethyl styrene oxide + H2O - Rattus norvegicus ? - ? 140157 3.3.2.9 trans-ethyl styrene oxide + H2O - Oryctolagus cuniculus ? - ? 140157 3.3.2.9 trans-ethyl styrene oxide + H2O trans-beta-ethyl styrene oxide Mus musculus ? - ? 140157 3.3.2.9 trans-stilbene oxide + H2O - Cavia porcellus ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O - Mus musculus ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O - Homo sapiens ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O - Oryctolagus cuniculus ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O - Cricetinae ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O - Heliothis virescens ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O cis-stilbene oxide hydrolase and trans-stilbene hydrolase isoenzymes are not structurally identical Macaca mulatta ? - ? 140144 3.3.2.9 trans-stilbene oxide + H2O - Mus musculus 1,2-diphenylethane-1,2-diol - ? 374749 3.3.2.9 trans-stilbene oxide + H2O - Homo sapiens 1,2-diphenylethane-1,2-diol - ? 374749 3.3.2.9 trans-stilbene oxide + H2O - Drosophila melanogaster 1,2-diphenylethane-1,2-diol - ? 374749 3.3.2.9 [3-(4-[[(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O - Homo sapiens [3-(4-[[(1,3-dihydroxypropan-2-yl)amino]methyl]phenoxy)azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone - ir 450859 3.3.2.9 [3-[4-([((3-methyloxetan-3-yl)methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O - Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone - ir 449297 3.3.2.9 [3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone + H2O - Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl](5-phenyl-1,3,4-oxadiazol-2-yl)methanone - ir 450860 3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-(4-[[(oxetan-3-yl)amino]methyl]phenoxy)azetidin-1-yl]methanone + H2O - Homo sapiens [3-(4-[[(1,3-dihydroxypropan-2-yl)amino]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone - ir 450861 3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O - Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone - ir 450862 3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O - Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl]amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone - ir 450863 3.3.2.9 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl][3-[4-([[(oxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]methanone + H2O - Homo sapiens [3-[4-([[3-hydroxy-2-(hydroxymethyl)propyl]amino]methyl)phenoxy]azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone - ir 450864 3.3.2.9 juvenile hormone III + H2O - Tribolium castaneum ? activity is less than 4 pmol/min/mg protein ? 140211 3.3.2.9 4-vinylcyclohexene + H2O - Mus musculus ? after exposure of ovary to 4-vinylcyclohexene, an inactive tetrol metabolite 4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane can be formed, potentially through detoxification action of mEH ? 416424 3.3.2.9 7,12-dimethylbenz[a]anthracene + 3 H2O - Mus musculus 7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide bioactivation reaction ? 416461 3.3.2.9 cis-(9S,10R)-epoxystearic acid + H2O - Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 39% (9R,10R)-diol and 61% (9S,10S)-diol ? 379592 3.3.2.9 cis-(9S,10R)-epoxystearic acid methyl ester + H2O - Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 48% (9R,10R)-diol and 52% (9S,10S)-diol ? 379593 3.3.2.9 cis-(9S,10R)-epoxystearic acid + H2O - Zea mays threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 52% (9R,10R)-diol and 48% (9S,10S)-diol ? 379592 3.3.2.9 cis-(9S,10R)-epoxystearic acid methyl ester + H2O - Zea mays threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 68% (9R,10R)-diol and 32% (9S,10S)-diol ? 379593 3.3.2.9 cis-(9R,10S)-epoxystearic acid methyl ester + H2O - Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 79% (9R,10R)-diol and 21% (9S,10S)-diol ? 379590 3.3.2.9 cis-(9R,10S)-epoxystearic acid + H2O - Rattus norvegicus threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 80% (9R,10R)-diol and 20% (9S,10S)-diol ? 379589 3.3.2.9 cis-(9R,10S)-epoxystearic acid methyl ester + H2O - Zea mays threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester enantioselective production of 83% (9R,10R)-diol and 17% (9S,10S)-diol ? 379590 3.3.2.9 cis-(9R,10S)-epoxystearic acid + H2O - Zea mays threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid enantioselective production of 84% (9R,10R)-diol and 16% (9S,10S)-diol ? 379589 3.3.2.9 2-methyl styrene oxide + H2O - Rattus norvegicus (2R)-2-phenylpropane-1,2-diol highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water ? 394139 3.3.2.9 4-t-butylstyrene oxide + H2O - Rattus norvegicus (1R)-1-(4-t-butylphenyl)ethane-1,2-diol highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water ? 394173 3.3.2.9 dihydronaphthalene oxide + H2O - Rattus norvegicus (1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water ? 394318 3.3.2.9 (5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O i.e. 11,12-EET Mus musculus (5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid i.e. 11,12-DHET ? 403051 3.3.2.9 (5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O i.e. 11,12-EET Homo sapiens (5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid i.e. 11,12-DHET ? 403051 3.3.2.9 cis-4,4'-dichlorostilbene oxide + H2O - Oryctolagus cuniculus (1R,2R)-1,2-bis(4-chlorophenyl)ethane-1,2-diol product identification ? 379597 3.3.2.9 cis-4,4'-diethylstilbene oxide + H2O - Oryctolagus cuniculus (1R,2R)-1,2-bis(4-ethylphenyl)ethane-1,2-diol product identification ? 379598 3.3.2.9 cis-4,4'-diisopropylstilbene oxide + H2O - Oryctolagus cuniculus (1R,2R)-1,2-bis(4-isopropylphenyl)ethane-1,2-diol product identification ? 379599 3.3.2.9 cis-4,4'-dimethylstilbene oxide + H2O - Oryctolagus cuniculus (1R,2R)-1,2-bis(4-methylphenyl)ethane-1,2-diol product identification ? 379600 3.3.2.9 racemic ethyl 3-phenylglycidate + H2O - Pseudomonas sp. (2R,3S)-ethyl 3-phenylglycidate production of (2R,3S)-ethyl 3-phenylglycidate with 95% enantiomeric excess and 26% yield in 12 h from 0.2% (w/v) of the racemat ? 380242 3.3.2.9 racemic ethyl 3-phenylglycidate + H2O - Pseudomonas sp. BZS21 (2R,3S)-ethyl 3-phenylglycidate production of (2R,3S)-ethyl 3-phenylglycidate with 95% enantiomeric excess and 26% yield in 12 h from 0.2% (w/v) of the racemat ? 380242 3.3.2.9 1-[3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one + H2O - Homo sapiens 1-[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one [3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one ir 449162