3.3.2.9 (1R,2R)-1,2-epoxy-1-phenyl-1-propane 88% inhibition at 0.8 mM 35208 3.3.2.9 (1S,2S)-1,2-epoxy-1-phenyl-1-propane 89% inhibition at 0.8 mM 35207 3.3.2.9 (2R,3R)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane 9.0% inhibition at 0.1 mM 35206 3.3.2.9 (2R,3R)-3-(4-nitrophenyl)glycidol 8.2% inhibition at 0.2 mM 57820 3.3.2.9 (2S,3S)-1-benzyloxy-2,3-epoxy-3-(4-nitrophenyl)propane 11% inhibition at 0.1 mM 35205 3.3.2.9 (2S,3S)-3-(4-nitrophenyl)glycidol 17% inhibition at 0.2 mM 57819 3.3.2.9 (2S,3S)-p-nitrophenyl-glycidol - 104008 3.3.2.9 (9E)-octadec-9-enamide - 15188 3.3.2.9 (S)-1-(1-phenylethyl)-3-(3-phenylpropyl)urea 15.4% inhibition at 0.01 mM 235732 3.3.2.9 1,1,1-trichloro-2,3-epoxypropane - 75077 3.3.2.9 1,1,1-Trichloropropene 2,3-oxide - 5227 3.3.2.9 1,1,1-trichloropropene oxide - 57849 3.3.2.9 1,1,1-trichloropropene-2,3-oxide - 239379 3.3.2.9 1,1,1-trifluoro-2-propanone - 104135 3.3.2.9 1,1-diphenyloxirane - 31996 3.3.2.9 1,3-dicyclohexylurea - 188244 3.3.2.9 1,3-diphenylurea - 201314 3.3.2.9 1-chloro-2,3-epoxypropane non-competitive inhibitor 48410 3.3.2.9 1-isopropyl-1-phenyloxirane - 32008 3.3.2.9 1-methyl-1-phenyloxirane - 21440 3.3.2.9 1-methylcyclohexene oxide - 32011 3.3.2.9 1-trichloropropene oxide - 48432 3.3.2.9 10-hydroxystearamide - 201309 3.3.2.9 12-hydroxyoctadecanamide - 15189 3.3.2.9 2-(nonylsulfanyl)propanamide - 15187 3.3.2.9 2-Bromo-4'-nitroacetophenone - 4468 3.3.2.9 2-nonylsulfanyl-propionamide - 75078 3.3.2.9 3,3,3-trichloropropene oxide - 13120 3.3.2.9 3,3,3-trifluoropropene oxide - 32057 3.3.2.9 3,3-dimethylbutene oxide - 32058 3.3.2.9 3-(decylthio)-1,1,1-trifluoropropan-2-one moderate inhibition 201313 3.3.2.9 3-(dodecylthio)-1,1,1-trifluoropropan-2-one moderate inhibition 201312 3.3.2.9 3-(octylthio)-1,1,1-trifluoropropan-2-one moderate inhibition 201311 3.3.2.9 3-methylbutene 1,2-oxide - 32072 3.3.2.9 3-methylcyclohexene oxide - 32073 3.3.2.9 3-phenylpropene 1,2-oxide - 32075 3.3.2.9 4-Chlorophenyl-2,3-epoxypropyl ether competitive 91674 3.3.2.9 4-Phenylchalcone oxide - 9061 3.3.2.9 5,5'-dithiobis(2-nitrobenzoic acid) - 221 3.3.2.9 7-oxabicyclo[4.1.0]heptane IC50 is 0.0022 mM 35223 3.3.2.9 Al3+ slight inhibition at 1 mM 264 3.3.2.9 androstene oxide inhibits hydration of estroxide and styrene 7,8-oxide 48826 3.3.2.9 Ba2+ 15% inhibition at 1 mM 111 3.3.2.9 Ba2+ slight inhibition at 1 mM 111 3.3.2.9 beta-dimethylstyrene oxide - 239378 3.3.2.9 Ca2+ 20% inhibition at 1 mM 15 3.3.2.9 Ca2+ 25% inhibition at 1 mM 15 3.3.2.9 Ca2+ slight inhibition at 1 mM 15 3.3.2.9 Cd2+ 20% inhibition at 1 mM 52 3.3.2.9 Cd2+ 70% inhibition at 1 mM 52 3.3.2.9 Cd2+ 5 mM, 14% residual activity 52 3.3.2.9 Chalcone oxide - 3805 3.3.2.9 cis-2-methyl-1-phenyloxirane - 32175 3.3.2.9 cis-beta-methylstyrene oxide - 108788 3.3.2.9 cis-stilbene oxide - 4232 3.3.2.9 Co2+ 20% inhibition at 1 mM 23 3.3.2.9 Co2+ 25% inhibition at 1 mM 23 3.3.2.9 Cu2+ - 19 3.3.2.9 Cu2+ slight inhibition at 1 mM 19 3.3.2.9 Cu2+ 25% inhibition at 1 mM 19 3.3.2.9 cyclohexane oxide - 57850 3.3.2.9 Cyclohexene oxide - 3996 3.3.2.9 Cyclohexene oxide inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide 3996 3.3.2.9 Cyclohexene oxide using a post-natal day 4 Fischer 344 rat whole ovary culture system, inhibition of mEH using cyclohexene oxide during 4-vinylcyclohexene exposure results in a greater loss of primordial and small primary follicles relative to 4-vinylcyclohexene-treated ovaries. Also, relative to controls, mEH mRNA is increased on day 4 of 4-vinylcyclohexene exposure, followed by increased mEH protein after 6 days. Inhibition of PI3K signaling increases mEH mRNA and protein expression 3996 3.3.2.9 Cyclohexene oxide a post-natal day 4 Fischer 344 rat whole ovary culture system inhibition of mEH using cyclohexene oxide during VCD exposure results in a greater loss of primordial and small primary follicles relative to VCD-treated ovaries 3996 3.3.2.9 elaidamide mixed inhibition type 7648 3.3.2.9 elaidamide - 7648 3.3.2.9 elaidamide most potent inhibitor, has a mix of competitive and non-competitive inhibition kinetics 7648 3.3.2.9 Emulgen 911 0.1%, 53% inhibition 9392 3.3.2.9 Emulgen 911 slight inhibition 9392 3.3.2.9 estroxide inhibits hydration of androstene oxide and styrenen 7,8-oxide 44109 3.3.2.9 H2O2 5 mM, 79% residual activity 22 3.3.2.9 Hg2+ 90% inhibition at 1 mM 33 3.3.2.9 Hg2+ over 90% inhibition at 1 mM 33 3.3.2.9 Hg2+ 70% inhibition at 1 mM 33 3.3.2.9 Hg2+ 5 mM, 36% residual activity 33 3.3.2.9 indene 1,2-oxide - 21619 3.3.2.9 iodoacetamide 0.1 mM, 15% inhibition 67 3.3.2.9 iodoacetamide - 67 3.3.2.9 juvenile hormone I competitive 7215 3.3.2.9 Lipid above the critrical micelle concentration gives kinetic pattern that mimics competitive inhibition 3254 3.3.2.9 Lubrol 0.025% 6679 3.3.2.9 Lubrol Lubrol PX; phospholipid reverses the inhibition 6679 3.3.2.9 Lubrol Lubrol PX 6679 3.3.2.9 m-bromostyrene oxide - 32280 3.3.2.9 m-nitrostyrene oxide - 32283 3.3.2.9 Mersalyl 0.09 mM, 13% inhibition 1982 3.3.2.9 methoxyarachidonyl fluorophosphate - 201310 3.3.2.9 methyl-p-epoxymethylbenzoate - 32290 3.3.2.9 Metyrapone strong inhibition of hydration of benzopyrene 11,12-oxide and dibenzoanthracene 5,6-oxide 990 3.3.2.9 Mg2+ 30% inhibition at 1 mM 6 3.3.2.9 Mg2+ 10% inhibition at 1 mM 6 3.3.2.9 Mn2+ 10% inhibition at 1 mM 11 3.3.2.9 Mn2+ 20% inhibition at 1 mM 11 3.3.2.9 additional information 5,6alpha-epoxy-5alpha-cholestan-3beta-ol causes down-regulation of the enzyme, no effect by cholestyramine and clofibrate 2 3.3.2.9 additional information no inhibition by 3-phenylglycidol enantiomers, inhibitor synthesis, overview, inhibition mechanisms, overview 2 3.3.2.9 additional information no inhibition by 5,6alpha-imino-5alpha-cholestane-3beta-ol 2 3.3.2.9 additional information no inhibition by isoquinoline, 7-oxocholesterol, 7-oxocholestanol, and 6-oxocholestanol 2 3.3.2.9 additional information HNF3 negatively regulates the transactivation of E1 promoter by GATA-4 in hepatoma cells 2 3.3.2.9 additional information suppression of enzyme expression by glucocorticoid, interacting with the 5'-flanking sequence, and by dexamethasone, gadolinium chloride, acriflavine, lipopolysaccharide, gem-di-, trans-di-, tri- and tetra-substituted epoxides are either low turnover substrates or inhibitors 2 3.3.2.9 additional information suppression of enzyme expression by dexamethasone, gadolinium chloride, acriflavine, lipopolysaccharide 2 3.3.2.9 additional information quantitative structure-activity relationships in epoxides inhibiting EH activity, molecular modelling, kinetics, overview 2 3.3.2.9 additional information metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions 2 3.3.2.9 additional information no inhibition by Co2+ at 1 mM, metal chelators like 1,10-phenanthroline, 1,7-phenanthroline, EDTA, EGTA, and dipicolinic acid preserve enzyme activity in presence of metal ions 2 3.3.2.9 additional information not inhibitory: 3-octylthio-1,1,1-trifluoro-2-propanone; not inhibitory: 3-octylthio-1,1,1-trifluoro-2-propanone; not inhibitory: 3-octylthio-1,1,1-trifluoro-2-propanone 2 3.3.2.9 additional information not inhibited by trans-4-[4-(1-adamantylcarbamoylamino)cyclohexyloxy] benzoic acid 2 3.3.2.9 additional information not inhibitory: EDTA 2 3.3.2.9 additional information enantioselective urea inhibitors of soluble epoxide hydrolase (sEH, EC 3.3.2.9) have mostly no inhibitory effect on the microsomal epoxide hydrolase, mEH, some are slightly activating for mEH. No inhibition by 12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid (AUDA) 2 3.3.2.9 additional information no inhibition by cis-2,3-epoxybutane and 2,3-dimethyl-2,3-epoxybutane 2 3.3.2.9 N-(phenylcarbamothioyl)acetamide - 199884 3.3.2.9 N-(phenylcarbamothioyl)benzamide - 124168 3.3.2.9 N-(pyridin-4-ylcarbamothioyl)acetamide - 199895 3.3.2.9 N-(pyridin-4-ylcarbamothioyl)benzamide - 199908 3.3.2.9 N-(tert-butylcarbamothioyl)acetamide - 199894 3.3.2.9 N-(tert-butylcarbamothioyl)benzamide - 199907 3.3.2.9 N-acetyl-N'-adamantyl thiourea - 201316 3.3.2.9 N-acetyl-N'-[(3-trifluoromethyl-4-bromo)phenyl] thiourea - 201315 3.3.2.9 N-benzoyl-N'-adamantyl thiourea - 201318 3.3.2.9 N-benzoyl-N'-[(3-trifluoromethyl-4-bromo)phenyl] thiourea - 201317 3.3.2.9 n-octene 1,2-oxide - 32342 3.3.2.9 N-[(2,6-dichlorophenyl)carbamothioyl]acetamide - 199888 3.3.2.9 N-[(2,6-dichlorophenyl)carbamothioyl]benzamide - 199901 3.3.2.9 N-[(2,6-diethoxyphenyl)carbamothioyl]acetamide - 199889 3.3.2.9 N-[(2,6-diethoxyphenyl)carbamothioyl]benzamide - 199902 3.3.2.9 N-[(2-methoxy-4-methylphenyl)carbamothioyl]acetamide - 199891 3.3.2.9 N-[(2-methoxy-4-methylphenyl)carbamothioyl]benzamide - 199904 3.3.2.9 N-[(2-methoxy-4-nitrophenyl)carbamothioyl]acetamide - 199890 3.3.2.9 N-[(2-methoxy-4-nitrophenyl)carbamothioyl]benzamide - 199903 3.3.2.9 N-[(2-methylphenyl)carbamothioyl]acetamide - 199885 3.3.2.9 N-[(2-methylphenyl)carbamothioyl]benzamide - 199898 3.3.2.9 N-[(4-bromonaphthalen-1-yl)carbamothioyl]acetamide - 199896 3.3.2.9 N-[(4-bromonaphthalen-1-yl)carbamothioyl]benzamide - 199909 3.3.2.9 N-[(4-bromophenyl)carbamothioyl]acetamide - 199887 3.3.2.9 N-[(4-bromophenyl)carbamothioyl]benzamide - 199900 3.3.2.9 N-[(4-chlorophenyl)carbamothioyl]acetamide - 199886 3.3.2.9 N-[(4-chlorophenyl)carbamothioyl]benzamide - 199899 3.3.2.9 N-[(4-phenoxyphenyl)carbamothioyl]acetamide - 199892 3.3.2.9 N-[(4-phenoxyphenyl)carbamothioyl]benzamide - 199905 3.3.2.9 N-[[4-(morpholin-4-yl)phenyl]carbamothioyl]acetamide - 201319 3.3.2.9 N-[[4-(morpholin-4-yl)phenyl]carbamothioyl]benzamide - 201320 3.3.2.9 naphthalene 1,2-oxide - 13206 3.3.2.9 Ni2+ 30% inhibition at 1 mM 38 3.3.2.9 omega-bromo-nitro-acetophenone - 49313 3.3.2.9 p-bromostyrene oxide - 32369 3.3.2.9 p-chlorophenyl 2,3-epoxypropyl ether - 32370 3.3.2.9 p-hydroxymercuribenzoate 0.1 mM, 15% inhibition 98 3.3.2.9 p-hydroxymercuribenzoate - 98 3.3.2.9 p-nitrostyrene oxide - 16713 3.3.2.9 p-phenylstyrene oxide - 32377 3.3.2.9 Pb2+ 10% inhibition at 1 mM 139 3.3.2.9 Pb2+ 30% inhibition at 1 mM 139 3.3.2.9 progabide low micromolar inhibitor 33227 3.3.2.9 progabide less than 20% residual activity at 0.02 mM 33227 3.3.2.9 propene oxide - 32392 3.3.2.9 sodium cholate inhibits hydration of estroxide and androstene oxide 1209 3.3.2.9 sodium deoxycholate inhibits hydration of estroxide and androstene oxide 549 3.3.2.9 styrene 7,8-oxide inhibits hydration of estroxide and androstene oxide 12692 3.3.2.9 styrene oxide - 2222 3.3.2.9 trans-beta-methylstyrene oxide - 32418 3.3.2.9 trans-stilbene oxide inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide 3367 3.3.2.9 trichloropropene oxide inhibits hydration of estroxide, androstene oxide and styrene 7,8-oxide 7465 3.3.2.9 trichloropropene oxide - 7465 3.3.2.9 Tween-80 0.025% 2672 3.3.2.9 Tween-80 inhibits hydration of estroxide and androstene oxide 2672 3.3.2.9 urea derivatives - 35224 3.3.2.9 valpromide - 11511 3.3.2.9 valpromide low micromolar inhibitor 11511 3.3.2.9 valpromide 50% inhibition at 0.01 mM 11511 3.3.2.9 Zn2+ 80% inhibition at 1 mM 14 3.3.2.9 Zn2+ over 90% inhibition at 1 mM 14 3.3.2.9 Zn2+ 5 mM, 41% residual activity 14