1.13.11.27 (2,6-difluoro-4-hydroxyphenyl)pyruvate competitive, most potent 49562 1.13.11.27 (3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5,7-dichlorobenzofuran-2-yl)methanone - 260757 1.13.11.27 (3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5-nitrobenzofuran-2-yl)methanone compound displays excellent herbicidal activity 260758 1.13.11.27 (5,7-dichlorobenzofuran-2-yl)(5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanone compound displays excellent herbicidal activity 260811 1.13.11.27 1,10-phenanthroline - 62 1.13.11.27 1,10-phenanthroline 0.01 mM, 50% inhibition 62 1.13.11.27 1,2-dihydroxybenzene 0.019 mM, 50% inhibition, uncompetitive 10458 1.13.11.27 1,2-dihydroxybenzene-3,5-disulfonic acid inhibition is prevented by ascorbate but not reversed by enol-4-hydroxyphenylpyruvate 107545 1.13.11.27 1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one - 219959 1.13.11.27 1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one - 219942 1.13.11.27 1,4-benzoquinone 0.25 mM, 50% inhibition, competitive 315 1.13.11.27 1,4-dihydroxybenzene 4.7 mM, 50% inhibition 10460 1.13.11.27 1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole 50% inhibition at 7 nM 55823 1.13.11.27 1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole 50% inhibition below 20 nM 55823 1.13.11.27 1-(2'-thenonyl)-3,3,3-trifluoroacetone 0.0049 mM, 50% inhibition 107851 1.13.11.27 1-(2'-thionyl)-3,3,3-trifluoroacetone - 107852 1.13.11.27 1-(2-chloropyridin-3-yl)-2-(2-oxo-1,3-oxazolidin-3-yl)ethane-1,2-dione - 260938 1.13.11.27 1-(furan-2-ylcarbonyl)pyrrolidine-2,5-dione - 260970 1.13.11.27 1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219939 1.13.11.27 1-benzyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219876 1.13.11.27 1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode 219859 1.13.11.27 1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219950 1.13.11.27 1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219932 1.13.11.27 1-butyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219873 1.13.11.27 1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219856 1.13.11.27 1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219952 1.13.11.27 1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219934 1.13.11.27 1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one - 219945 1.13.11.27 1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219954 1.13.11.27 1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one - 219961 1.13.11.27 1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219936 1.13.11.27 1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one - 219946 1.13.11.27 1-ethyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219871 1.13.11.27 1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219864 1.13.11.27 1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode 219854 1.13.11.27 1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one - 219944 1.13.11.27 1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one - 219955 1.13.11.27 1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219877 1.13.11.27 1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219860 1.13.11.27 1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]pyrrolidine-2,5-dione - 260983 1.13.11.27 1-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione - 261008 1.13.11.27 1-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione - 261009 1.13.11.27 1-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione - 261010 1.13.11.27 2,2'-bipyridyl - 1706 1.13.11.27 2,2'-bipyridyl 1.8 mM, 50% inhibition 1706 1.13.11.27 2,2'-bipyridyl 0.32 mM, 50% inhibition 1706 1.13.11.27 2,4-Dihydroxybenzoate 4.2 mM, 50% inhibition, noncompetitive 1909 1.13.11.27 2,4-Dihydroxyphenylpyruvate competitive 90834 1.13.11.27 2,5-Dihydroxybenzoate 2.6 mM, 50% inhibition, noncompetitive 2065 1.13.11.27 2,5-dihydroxyphenylacetate 50% inhibition above 10 mM, noncompetitive 9304 1.13.11.27 2,5-dihydroxyphenylacetic acid lactone 50% inhibition above 10 mM, competitive 107997 1.13.11.27 2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile - 220040 1.13.11.27 2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one - 219985 1.13.11.27 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219966 1.13.11.27 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one - 219984 1.13.11.27 2-(2-chloro-4-methane sulfonylbenzoyl)-1,3-cyclohexanedione competitive inhibitor 155079 1.13.11.27 2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione potent linear competitive inhibitor 16758 1.13.11.27 2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione - 16758 1.13.11.27 2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione rapid inactivation of the enzyme by the formation of an enzyme-inhibitor complex that dissociates with recovery of enzyme activity 16758 1.13.11.27 2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one - 219978 1.13.11.27 2-(2-nitro-4-(trifluoromethyl)benzoyl)-1,3-cyclohexanedione (NTBC), binding constant of 937 microM 135218 1.13.11.27 2-(2-nitro-4-chlorobenzoyl)-5-(2-methoxyethyl)cyclohexane-1,3-dione - 108019 1.13.11.27 2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione NTBC, a commercial HPPD inhibitor in clinical use 219930 1.13.11.27 2-(5,7-dichlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one - 261097 1.13.11.27 2-(5-chlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one - 261098 1.13.11.27 2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219989 1.13.11.27 2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219965 1.13.11.27 2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219995 1.13.11.27 2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one - 219987 1.13.11.27 2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219969 1.13.11.27 2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219994 1.13.11.27 2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219973 1.13.11.27 2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219972 1.13.11.27 2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one - 219986 1.13.11.27 2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219971 1.13.11.27 2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one - 219967 1.13.11.27 2-(furan-2-ylcarbonyl)-1H-isoindole-1,3(2H)-dione - 261108 1.13.11.27 2-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione showed the highest HPPD inhibitory activity of the compounds tested 261140 1.13.11.27 2-Hydroxybenzaldehyde competitive 3590 1.13.11.27 2-hydroxyphenylacetate product inhibition 6428 1.13.11.27 2-hydroxyphenylacetate 10 mM, 50% inhibition, noncompetitive 6428 1.13.11.27 2-hydroxyphenylacetate - 6428 1.13.11.27 2-Hydroxyphenylpyruvate competitive 91064 1.13.11.27 2-mercaptoethanol 10 mM, 65% inhibition 63 1.13.11.27 2-thienylpyruvate mechanism-based inhibitor 32522 1.13.11.27 2-[(2,3-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220019 1.13.11.27 2-[(2,4-dibromophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one - 220029 1.13.11.27 2-[(2,4-dibromophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220028 1.13.11.27 2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one - 220027 1.13.11.27 2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one - 220026 1.13.11.27 2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one - 220025 1.13.11.27 2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220020 1.13.11.27 2-[(2,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220021 1.13.11.27 2-[(2,6-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220022 1.13.11.27 2-[(2-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220037 1.13.11.27 2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one - 220010 1.13.11.27 2-[(2-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220009 1.13.11.27 2-[(2-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione - 261183 1.13.11.27 2-[(3,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220023 1.13.11.27 2-[(3,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220024 1.13.11.27 2-[(3-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220011 1.13.11.27 2-[(3-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione - 261185 1.13.11.27 2-[(4-bromo-2-fluorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione - 261187 1.13.11.27 2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220035 1.13.11.27 2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220038 1.13.11.27 2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one - 220034 1.13.11.27 2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one - 220033 1.13.11.27 2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one - 220032 1.13.11.27 2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220031 1.13.11.27 2-[(4-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220012 1.13.11.27 2-[(4-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione - 261188 1.13.11.27 2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one - 220030 1.13.11.27 2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one - 219980 1.13.11.27 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione mechanism of binding, enzyme-Fe(II)-inhibitor complex does not oxidize, dissociation rate constant is essentially zero 23285 1.13.11.27 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione - 23285 1.13.11.27 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione is a selective and efficient herbicide that can be applied as a medicine in a hereditary metabolic disease - tyrosinemia type I 23285 1.13.11.27 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione herbicide, drug to treat inborn defects of tyrosine catabolism, specifically type I tyrosinemia and alkaptonuria 23285 1.13.11.27 2-[2-nitro-4-(trifluoromethyl)benzoyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione 50 nM, 50% inhibition, tight-binding reversible inhibitor, rapid inactivation by the formation of an enzyme-inhibitor complex that dissociates extremely slowly with recovery of enzyme activity 108027 1.13.11.27 2-[3-[(2,4-dichlorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one - 261201 1.13.11.27 2-[3-[(2,4-difluorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one - 261202 1.13.11.27 2-[3-[(3,5-dimethylphenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one - 261204 1.13.11.27 2-[3-[(4-bromo-2-fluorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one - 261205 1.13.11.27 2-[3-[(4-bromophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one - 261206 1.13.11.27 2-[3-[(4-bromophenyl)methoxy]benzoyl]-3-hydroxycyclohex-2-en-1-one - 261207 1.13.11.27 2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one - 220055 1.13.11.27 2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one - 220054 1.13.11.27 2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one - 220053 1.13.11.27 2-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione - 261226 1.13.11.27 2-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione - 261227 1.13.11.27 2-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione - 261228 1.13.11.27 2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one - 220057 1.13.11.27 3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate - 76259 1.13.11.27 3,4-dihydroxybenzoate 0.24 mM, 50% inhibition, noncompetitive 736 1.13.11.27 3,4-Dihydroxyphenylacetate 0.75 mM, 50% inhibition, noncompetitive 838 1.13.11.27 3,5-diiodo-4-hydroxyphenylpyruvate 0.25 mM, 50% inhibition, competitive 10497 1.13.11.27 3-(2,4-dimethylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219899 1.13.11.27 3-(2,4-dimethylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219929 1.13.11.27 3-(2,6-dimethylphenyl)-1-methyl-6-(2-oxidanyl-6-oxidanylidene-cyclohexen-1-yl)carbonyl-quinazoline-2,4-dione competitive inhibitor with respect to HPPA with the characteristic of slow binding and lower potency against human enzyme 261258 1.13.11.27 3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219902 1.13.11.27 3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219925 1.13.11.27 3-(2-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219908 1.13.11.27 3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219904 1.13.11.27 3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219928 1.13.11.27 3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione - 219853 1.13.11.27 3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione - 219867 1.13.11.27 3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione - 219849 1.13.11.27 3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219886 1.13.11.27 3-(2-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219907 1.13.11.27 3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione - 76260 1.13.11.27 3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219900 1.13.11.27 3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219927 1.13.11.27 3-(2-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219889 1.13.11.27 3-(2-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219906 1.13.11.27 3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile - 220000 1.13.11.27 3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile - 219999 1.13.11.27 3-(2-hydroxyphenyl)propionate 50% inhibition above 10 mM, competitive 49764 1.13.11.27 3-(3,4-dichlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219926 1.13.11.27 3-(3-bbromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219892 1.13.11.27 3-(3-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219913 1.13.11.27 3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione - 219866 1.13.11.27 3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione - 219848 1.13.11.27 3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219891 1.13.11.27 3-(3-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219912 1.13.11.27 3-(3-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219893 1.13.11.27 3-(3-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219911 1.13.11.27 3-(4-bromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219896 1.13.11.27 3-(4-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219919 1.13.11.27 3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219903 1.13.11.27 3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219923 1.13.11.27 3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione - 219865 1.13.11.27 3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione - 219847 1.13.11.27 3-(4-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219898 1.13.11.27 3-(4-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219918 1.13.11.27 3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219901 1.13.11.27 3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219924 1.13.11.27 3-(4-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219894 1.13.11.27 3-(4-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one - 219917 1.13.11.27 3-(furan-2-ylcarbonyl)-1,3-oxazolidin-2-one - 261300 1.13.11.27 3-(furan-2-ylcarbonyl)-1,3-thiazolidin-2-one - 261301 1.13.11.27 3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one - 76262 1.13.11.27 3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one - 219960 1.13.11.27 3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one - 219958 1.13.11.27 3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one - 219943 1.13.11.27 3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one - 219941 1.13.11.27 3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one - 219996 1.13.11.27 3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one - 219993 1.13.11.27 3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one - 219992 1.13.11.27 3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one - 219991 1.13.11.27 3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one - 219977 1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one - 219976 1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one - 219974 1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one - 219975 1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one - 219983 1.13.11.27 3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one - 219982 1.13.11.27 3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one - 219968 1.13.11.27 3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one - 219981 1.13.11.27 3-hydroxy-2-(3,5,6-trichloro-4-((4-chlorobenzyl)amino)picolinoyl)cyclohex-2-en-1-one compound displays excellent greenhouse herbicidal effects at 150 g of active ingredient/ha after postemergence treatment and show superior weed-controlling efficacy against Setaria viridis 261311 1.13.11.27 3-hydroxy-2-(3,5,6-trichloro-4-((4-isopropylbenzyl)amino)picolinoyl)cyclohex-2-en-1-one an additional pi-pi stacking interaction with Phe-392 and hydrophobic contacts with Met335 and Pro384 are detected in AtHPPD upon the binding. Compound displays excellent greenhouse herbicidal effects at 150 g of active ingredient/ha after postemergence treatment 261312 1.13.11.27 3-hydroxy-2-(3,5,6-trichloro-4-((4-methylbenzyl)amino)-picolinoyl)cyclohex-2-en-1-one compound displays excellent greenhouse herbicidal effects at 150 g of active ingredient/ha after postemergence treatment 261313 1.13.11.27 3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one - 219979 1.13.11.27 3-hydroxy-2-(5-nitrobenzofuran-2-carbonyl)cyclohex-2-en-1-one - 261314 1.13.11.27 3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one - 220001 1.13.11.27 3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one binding free energy -19.81 kcal/mol, residue groups including Val207, Leu244, His287, Ala289, Phe371, Glu373, Lys400, and Phe403 participate in the binding 220001 1.13.11.27 3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one - 219964 1.13.11.27 3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one - 220041 1.13.11.27 3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one - 220036 1.13.11.27 3-hydroxy-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one - 220003 1.13.11.27 3-hydroxy-2-[(2-nitrophenoxy)acetyl]cyclohex-2-en-1-one - 220016 1.13.11.27 3-hydroxy-2-[(3-methylphenoxy)acetyl]cyclohex-2-en-1-one - 220005 1.13.11.27 3-hydroxy-2-[(4-methoxyphenoxy)acetyl]cyclohex-2-en-1-one - 220007 1.13.11.27 3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]cyclohex-2-en-1-one - 220039 1.13.11.27 3-hydroxy-2-[(4-methylphenoxy)acetyl]cyclohex-2-en-1-one - 220006 1.13.11.27 3-hydroxy-2-[(pentafluorophenoxy)acetyl]cyclohex-2-en-1-one - 220042 1.13.11.27 3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one - 219990 1.13.11.27 3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one - 219988 1.13.11.27 3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one - 219970 1.13.11.27 3-hydroxy-2-[3-[(4-isopropylphenyl)methoxy]-2-nitrobenzoyl]cyclohex-2-en-1-one - 261315 1.13.11.27 3-hydroxy-2-[3-[(4-methylphenyl)methoxy]-2-nitrobenzoyl]cyclohex-2-en-1-one - 261316 1.13.11.27 3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one - 219998 1.13.11.27 3-hydroxy-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one - 220043 1.13.11.27 3-hydroxy-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one - 220047 1.13.11.27 3-hydroxy-2-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one - 220008 1.13.11.27 3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one - 220013 1.13.11.27 3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one - 220014 1.13.11.27 3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one - 220018 1.13.11.27 3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one - 220017 1.13.11.27 3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one - 220015 1.13.11.27 3-hydroxy-4,4-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one - 220046 1.13.11.27 3-hydroxy-4,4-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one - 220050 1.13.11.27 3-hydroxy-4-phenyl-2-furanone 0.0005 mM, 50% inhibition, may serve as a lead compound for further design of more potent inhibitors 108304 1.13.11.27 3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one - 220002 1.13.11.27 3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one binding free energy -3.65 kcal/mol, residue groups including Val207, Leu244, Pro259, Asn261, His287, Phe360, and Phe403 participate in the binding 220002 1.13.11.27 3-hydroxy-5,5-dimethyl-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one - 220004 1.13.11.27 3-hydroxy-5,5-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one - 220045 1.13.11.27 3-hydroxy-5,5-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one - 220049 1.13.11.27 3-hydroxy-5-methyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one - 220044 1.13.11.27 3-hydroxy-5-methyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one - 220048 1.13.11.27 3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one - 219997 1.13.11.27 3-hydroxyphenylpyruvate competitive 91477 1.13.11.27 3-methoxy-4-hydroxyphenylacetate 0.25 mM, 50% inhibition, competitive 48614 1.13.11.27 3-methoxy-4-hydroxyphenylpyruvate competitive 29494 1.13.11.27 3-thienylpyruvate mechanism-based inhibitor 32535 1.13.11.27 3-[(2E)-3-(2-bromo-5-hydroxyphenyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme 261330 1.13.11.27 3-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]-1,3-oxazolidin-2-one - 261335 1.13.11.27 3-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]-1,3-thiazolidin-2-one - 261336 1.13.11.27 3-[2-chloro-4-(methanesulfonyl)benzoyl]-1,3-oxazolidin-2-one compound forms a stable bidentate interaction with the active center CoII chelation. The benzene ring is sandwiched by the phenyl rings of residues Phe381 and Phe424. The compound shows good herbicidal activities against tested weeds Echinochloa crus-galli and Abutilon juncea 261347 1.13.11.27 3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one - 261360 1.13.11.27 3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one - 261361 1.13.11.27 3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one - 261362 1.13.11.27 3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one - 261363 1.13.11.27 3-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one - 261364 1.13.11.27 3-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one - 261365 1.13.11.27 4-(2,4-dichlorobenzyl)-1,3-dimethyl-5-hydroxypyrazole - 77059 1.13.11.27 4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76253 1.13.11.27 4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6-trimethyl-6-(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione - 76258 1.13.11.27 4-(3-cyclohexylpropanoyl)-5-methoxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76254 1.13.11.27 4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76252 1.13.11.27 4-acetyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76245 1.13.11.27 4-aminophenylpyruvate competitive 108376 1.13.11.27 4-decanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76255 1.13.11.27 4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione - 76263 1.13.11.27 4-dodecanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76256 1.13.11.27 4-hexanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76251 1.13.11.27 4-hydroxy-3-[(2E)-3-(3-iodophenyl)prop-2-enoyl]-6-methyl-2H-pyran-2-one compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme 261465 1.13.11.27 4-hydroxy-3-[(2E)-3-(3-methoxyphenyl)prop-2-enoyl]-6-methyl-2H-pyran-2-one compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme 261466 1.13.11.27 4-hydroxy-6-methyl-3-[(2E)-3-phenylprop-2-enoyl]-2H-pyran-2-one compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme 261469 1.13.11.27 4-hydroxybenzaldehyde 50% inhibition above 10 mM, noncompetitive 711 1.13.11.27 4-hydroxyphenylpyruvate above 0.2 mM; substrate inhibition 423 1.13.11.27 4-hydroxyphenylpyruvate substrate inhibition 423 1.13.11.27 4-hydroxyphenylpyruvate interaction of enol-4-hydroxyphenylpyruvate with enzyme-bound Fe3+, formed by autooxidation, causes the substrate inhibition 423 1.13.11.27 4-hydroxyphenylpyruvate enzyme form 2 and 3, no substrate inhibition is observed for enzyme form 1 423 1.13.11.27 4-hydroxyphenylpyruvate - 423 1.13.11.27 4-hydroxyphenylpyruvate above 0.2 mM 423 1.13.11.27 4-hydroxytetrafluorophenylpyruvate mechanism-based inhibitor 32547 1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one - 219962 1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219951 1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219953 1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one - 219963 1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one - 219956 1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one - 219949 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one - 219947 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219933 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219935 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one - 219948 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-[(3-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione - 261550 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one - 219938 1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one - 219931 1.13.11.27 5-hydroxy-2,2,6,6-tetramethyl-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione - 76249 1.13.11.27 5-hydroxy-2,2,6,6-tetramethyl-4-(2-phenylacetyl)cyclohex-4-ene-1,3-dione - 76247 1.13.11.27 5-hydroxy-2,2,6,6-tetramethyl-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione - 76248 1.13.11.27 5-hydroxy-2,2,6,6-tetramethyl-4-(3-phenylpropanoyl)cyclohex-4-ene-1,3-dione - 76250 1.13.11.27 5-hydroxy-2,2,6,6-tetramethyl-4-palmitoylcyclohex-4-ene-1,3-dione - 76257 1.13.11.27 5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione - 76261 1.13.11.27 5-hydroxy-4-isobutyryl-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione - 76246 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219870 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219869 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219868 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione - 219874 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione - 219875 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione - 219872 1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219879 1.13.11.27 6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219863 1.13.11.27 6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219862 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219852 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219851 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode 219850 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione - 219861 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione - 219857 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione - 219858 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione - 219855 1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode 219878 1.13.11.27 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one - 219890 1.13.11.27 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one - 219887 1.13.11.27 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one - 219897 1.13.11.27 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one - 219888 1.13.11.27 6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one - 219895 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(3-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one - 219916 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one - 219922 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one - 219914 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one - 219909 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one - 219920 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-phenylquinazolin-4(3H)-one - 219905 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one - 219910 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(3-methoxyphenyl)-2-methylquinazolin-4(3H)-one - 219915 1.13.11.27 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one - 219921 1.13.11.27 6-[2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile - 220052 1.13.11.27 6-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile - 220051 1.13.11.27 7-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]-2H-1-benzopyran-2-one - 220056 1.13.11.27 8-Hydroxyquinoline-5-sulfonic acid 560 nM, 50% inhibition 3980 1.13.11.27 Acetopyruvate 0.33 mM, 50% inhibition, competitive 5925 1.13.11.27 Al3+ 10 mM, 7% inhibition 264 1.13.11.27 Bathocuproine 3 mM, 50% inhibition 6489 1.13.11.27 bathophenanthroline - 2722 1.13.11.27 bathophenanthroline 0.018 mM, 50% inhibition; reactivation to 30% by dialysis and to 60% by addition to Fe2+ 2722 1.13.11.27 bathophenanthroline 0.012 mM, 50% inhibition 2722 1.13.11.27 benzobicyclon hydrolysate - 77060 1.13.11.27 benzobicyclone - 219843 1.13.11.27 bicyclopyrone - 219846 1.13.11.27 Ca2+ 10 mM, 16% inhibition 15 1.13.11.27 citrate - 131 1.13.11.27 Co2+ 10 mM, 32% inhibition 23 1.13.11.27 Cu2+ 10 mM, complete inhibition 19 1.13.11.27 Cupferron - 3624 1.13.11.27 Cupferron 0.0011 mM, 50% inhibition 3624 1.13.11.27 Cupferron 0.0071 mM, 50% inhibition 3624 1.13.11.27 Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219940 1.13.11.27 DAS 645 strong inhibition 219884 1.13.11.27 DAS 645 low inhibition 219884 1.13.11.27 DAS 869 - 219885 1.13.11.27 DAS 869 strong inhibition 219885 1.13.11.27 DEPC 1 mM, no residual activity 24059 1.13.11.27 diethyl dicarbonate 5 mM, 50% inhibition 463 1.13.11.27 diethyldithiocarbamate - 373 1.13.11.27 diethyldithiocarbamate 0.0049 mM, 50% inhibition; restored by dialysis 373 1.13.11.27 diethyldithiocarbamate 0.0021 mM, 50% inhibition 373 1.13.11.27 diketonitrile of isoxaflutole half-site reactivity, nearly irreversible 108877 1.13.11.27 Dithizone - 20248 1.13.11.27 Dithizone 0.14 mM, 50% inhibition 20248 1.13.11.27 DL-3,4-dihydroxyphenylalanine 0.32 mM, 50% inhibition, noncompetitive 93253 1.13.11.27 DL-4-hydroxyphenyllactate 50% inhibition above 10 mM, competitive 49995 1.13.11.27 DL-Epinephrine 0.17 mM, 50% inhibition, noncompetitive 93276 1.13.11.27 DTT 10 mM, 61% inhibition 177 1.13.11.27 EDTA - 21 1.13.11.27 EDTA 10 mM, 76% inhibition 21 1.13.11.27 EDTA 1 mM, no residual activity 21 1.13.11.27 enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219957 1.13.11.27 ethanol 5% v/v, 50% inhibition, complete loss of activity at 20% v/v 69 1.13.11.27 Fe2+ 1 mM, 30% inhibition 25 1.13.11.27 Fe2+ 10 mM, 82% inhibition 25 1.13.11.27 Fe2+-chelators - 108946 1.13.11.27 grandiflorone - 143376 1.13.11.27 H2O2 0.01 mM-1 mM, 5-15% inhibition 22 1.13.11.27 H2O2 10 nM, 60% inhibition. 0.001 mM, complete inhibition 22 1.13.11.27 H2O2 10 mM, 30% inhibition 22 1.13.11.27 homogentisate product inhibition 1826 1.13.11.27 homogentisate - 1826 1.13.11.27 isoxaflutole - 219882 1.13.11.27 K+ 10 mM, 6% inhibition 39 1.13.11.27 L-Phe 10 mM, 50% inhibition, competitive 203 1.13.11.27 leptospermone - 143375 1.13.11.27 manuka oil - 143373 1.13.11.27 mesotrione binding constant of 602 microM 126073 1.13.11.27 mesotrione - 126073 1.13.11.27 mesotrione molecular docking and molecular dynamics simulation estimate the interacting regions of HPPD with mesotrione using structure PDB ID 3ISQ 126073 1.13.11.27 mesotrione low inhibition, the isozyme is resistant to this herbicide 126073 1.13.11.27 mesotrione mesotrione is an extremely potent competitive inhibitor of this enzyme 126073 1.13.11.27 mesotrione low inhibition 126073 1.13.11.27 mesotrione binding free energy -12.26 kcal/mol 126073 1.13.11.27 mesotrione slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase 126073 1.13.11.27 mesotrione binding free energy -28.34 kcal/mol, residues Val207, Leu244, Leu347, Phe398, Gly399, Phe403, and Phe407 make the greatest contribution to the binding energy 126073 1.13.11.27 methyl 3-chloro-4-[(2-oxo-1,3-oxazolidin-3-yl)carbonyl]benzenesulfinate - 261906 1.13.11.27 methyl 3-nitro-4-[(2-oxo-1,3-oxazolidin-3-yl)carbonyl]benzenesulfinate - 261907 1.13.11.27 methyl 3-nitro-4-[(2-oxo-1,3-thiazolidin-3-yl)carbonyl]benzenesulfinate - 261908 1.13.11.27 Mg2+ 10 mM, 18% inhibition 6 1.13.11.27 Mn2+ 10 mM, 97% inhibition 11 1.13.11.27 additional information neither epoxybenzoaquinone ester nor 2-hydroxy-3-phenyl-3-butenoic acid is an inhibitor 2 1.13.11.27 additional information the enzyme is molecular target of new families of potent herbicides 2 1.13.11.27 additional information [1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone, no significant inhibition up to 0.02 mM 2 1.13.11.27 additional information high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors 2 1.13.11.27 additional information inhibition mechanism of enzyme HPPD, detailed overview 2 1.13.11.27 additional information structure-based design of a series of pyrazolone-quinazolone hybrids, as a class of human 4-hydroxyphenylpyruvate dioxygenase inhibitors, synthesis, overview. Molecular modeling indicates that the interaction between the pyrazolone ring and ferrous ion, and the hydrophobic interaction of quinazolone with its surrounding residues, such as Phe347 and Phe364, contribute greatly to the high potency of these inhibitors. Compounds N-(4-methoxyphenyl)-7-nitro-2,1,3-benzoxadiazol-4-amine and 3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one can be potentially useful for the treatment of type I tyrosinemia and other diseases with defects in tyrosine degradation 2 1.13.11.27 additional information synthesis of pyrazole-benzimidazolone hybrids from DNS869 and droperidol, bioevaluation of pyrazole-benzimidazolone hybrids as human 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview 2 1.13.11.27 additional information design, synthesis, and herbicidal activity of triketone-quinoline hybrids as 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview. Computational modeling and CoMSIA analysis 2 1.13.11.27 additional information efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview 2 1.13.11.27 additional information enzyme inhibition mechanisms and binding structures, molecular docking study, overview 2 1.13.11.27 additional information design, synthesis and herbicidal activity of quinazoline-2,4-diones as 4-hydroxyphenylpyruvate dioxygenase inhibitors with high herbicidal activity and improved cropselectivity, molecular dynamics simulations, structure-activity relationships, overview. Evaluation of herbicidal activity against against Echinochloa crus-galli, Setaria faberii, Digitaria sanguinalis, Amaranthus retroflexus, Eclipta prostrata, and Abutilon juncea 2 1.13.11.27 additional information hydrophobicity-oriented drug design strategy based on the interactions between HPPD and the commercial drug NTBC to idientify inhibitors 2 1.13.11.27 additional information formation of hHPPD-inhibitor complexes is mainly driven by van der Waals energy. Residues Ser226, Asn241, Gln265, Phe336, Phe359 and Phe364 make great contributions to binding affinities 2 1.13.11.27 additional information in silico structure-based virtual screening of four commercial databases to find inhibitors 2 1.13.11.27 additional information in silico analization of 2-(aryloxyacetyl)cyclohexane-1,3-diones derivatives as valid HPPD inhibitors 2 1.13.11.27 additional information not inhibitory at 1 mM: urea, PMSF 2 1.13.11.27 Na+ 10 mM, 14% inhibition 59 1.13.11.27 Ni2+ 10 mM, 28% inhibition 38 1.13.11.27 nitisinone i.e. orfadin or NTBC, an effective herbicide 219880 1.13.11.27 nitisinone i.e. orfadin or NTBC, addition of NTBC halts the morphology transition and stems pathogenesis in this organism 219880 1.13.11.27 nitisinone i.e. orfadin or NTBC, bidentate coordination of NTBC with the HPPD active site ferrous ion, enzyme-bound crystal structure, overview 219880 1.13.11.27 nitisinone NBTC, in clinical use 219880 1.13.11.27 nitisinone binding free energy -10.97 kcal/mol. Residues Tyr221 and Leu224 are involved in the interaction between nitisinone and HPPD 219880 1.13.11.27 nitisinone i.e. 2-[2-nitro-4-(trifluoromethyl) benzoyl]-1,3-cyclohexanedione, slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase 219880 1.13.11.27 nitisonone - 262275 1.13.11.27 NTBC tauromers 219883 1.13.11.27 NTBC tauromers, strong inhibition of the two tautomers 219883 1.13.11.27 o-hydroxyphenylpyruvate competitive inhibitor of 4-hydroxyphenylpyruvate 109341 1.13.11.27 oxaloacetate 10 mM, 50% inhibition, noncompetitive 57 1.13.11.27 pentafluorophenylpyruvate competitive 50192 1.13.11.27 phenylglyoxalate 50% inhibition above 10 mM, competitive 16804 1.13.11.27 phenylpyruvate non-competitive inhibition with 4-hydroxyphenylpyruvate as substrate 198 1.13.11.27 phenylpyruvate 0.53 mM, 50% inhibition, competitive 198 1.13.11.27 phenylpyruvate competitive 198 1.13.11.27 pinocembrin 5,7-dihydroxyflavanone, isolation from Flourensia oolepis ethanol extract, inhibition mechanism. Pinocembrin is a reversible inhibitor of the enzyme and acts as a noncompetitive inhibitor, molecular modeling studies and binding mode, overview. Comparison to other HPPD enzyme-inhibitor complexes 13785 1.13.11.27 pyrasulfotole - 262276 1.13.11.27 pyridoxal 5'-phosphate 2 mM, 50% inhibition 32 1.13.11.27 pyruvate 50% inhibition above 10 mM, competitive 31 1.13.11.27 SDS 2% (w/v), complete inhibition 124 1.13.11.27 sulcotrione for protein expressed in Escherichia coli DH5alpha (inhibition assayed without preincubation): 0 micoM sulcotrione = 100% activity, 0.5 microM sulcotrione = 58% activity left, 1.0 microM sulcotrione = 21.3% activity left, 1.5 microM sulcotrione = 2.8% activity left. Preincubation of the enzyme expressed in Escherichia coli SG13009 with sulcotrione for 15 min, significantly enhances the inhibition from 40% (1 microM sulcotrione/no preincubation) to 10% (1 microM sulcotrione/15 min preincubation). 135217 1.13.11.27 sulcotrione - 135217 1.13.11.27 sulcotrione strong inhibition 135217 1.13.11.27 sulcotrione low inhibition 135217 1.13.11.27 sulcotrione binding free energy -8.07 kcal/mol 135217 1.13.11.27 sulcotrione slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase 135217 1.13.11.27 tefuryltrione - 219844 1.13.11.27 tembotrione - 219845 1.13.11.27 tembotrione binding free energy -8.51 kcal/mol 219845 1.13.11.27 tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one - 219937 1.13.11.27 thiophenol oxalate - 50310 1.13.11.27 thiophenyl oxalate competitive 109651 1.13.11.27 Tiron 0.4 mM, 50% inhibition 1881 1.13.11.27 topramezone - 37649 1.13.11.27 trans-4-hydroxycinnamate 50% inhibition above 10 mM, competitive 30921 1.13.11.27 triketone-rich fraction - 143374 1.13.11.27 Urea 1 M, 3% inhibition. 3 M, 42% inhibition. 5 M, 56% inhibition 116 1.13.11.27 usnic acid - 219881 1.13.11.27 YCl3 1 mM, 50% inhibition 95375 1.13.11.27 Zn2+ 10 mM, 65% inhibition 14 1.13.11.27 [1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone 50% inhibition at 12 nM 122780