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(2,6-difluoro-4-hydroxyphenyl)pyruvate
-
competitive, most potent
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5,7-dichlorobenzofuran-2-yl)methanone
-
-
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5-nitrobenzofuran-2-yl)methanone
compound displays excellent herbicidal activity
-
(5,7-dichlorobenzofuran-2-yl)(5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanone
compound displays excellent herbicidal activity
-
1,2-dihydroxybenzene
-
0.019 mM, 50% inhibition, uncompetitive
1,2-dihydroxybenzene-3,5-disulfonic acid
-
inhibition is prevented by ascorbate but not reversed by enol-4-hydroxyphenylpyruvate
1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
1,4-benzoquinone
-
0.25 mM, 50% inhibition, competitive
1,4-dihydroxybenzene
-
4.7 mM, 50% inhibition
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
1-(2'-thenonyl)-3,3,3-trifluoroacetone
-
0.0049 mM, 50% inhibition
1-(2'-thionyl)-3,3,3-trifluoroacetone
-
-
1-(2-chloropyridin-3-yl)-2-(2-oxo-1,3-oxazolidin-3-yl)ethane-1,2-dione
-
-
1-(furan-2-ylcarbonyl)pyrrolidine-2,5-dione
-
-
1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-benzyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
binding mode
1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-butyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
1-ethyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
binding mode
1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one
-
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
-
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]pyrrolidine-2,5-dione
-
-
1-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione
-
-
1-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione
-
-
1-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione
-
-
2,4-Dihydroxybenzoate
-
4.2 mM, 50% inhibition, noncompetitive
2,4-Dihydroxyphenylpyruvate
-
competitive
2,5-Dihydroxybenzoate
-
2.6 mM, 50% inhibition, noncompetitive
2,5-dihydroxyphenylacetate
-
50% inhibition above 10 mM, noncompetitive
2,5-dihydroxyphenylacetic acid lactone
-
50% inhibition above 10 mM, competitive
2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile
-
2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(2-chloro-4-methane sulfonylbenzoyl)-1,3-cyclohexanedione
competitive inhibitor
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(2-nitro-4-(trifluoromethyl)benzoyl)-1,3-cyclohexanedione
-
(NTBC), binding constant of 937 microM
2-(2-nitro-4-chlorobenzoyl)-5-(2-methoxyethyl)cyclohexane-1,3-dione
-
-
2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione
NTBC, a commercial HPPD inhibitor in clinical use
2-(5,7-dichlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
2-(5-chlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(furan-2-ylcarbonyl)-1H-isoindole-1,3(2H)-dione
-
-
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
-
2-Hydroxybenzaldehyde
-
competitive
2-Hydroxyphenylpyruvate
-
competitive
2-mercaptoethanol
10 mM, 65% inhibition
2-thienylpyruvate
-
mechanism-based inhibitor
2-[(2,3-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2,6-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
2-[(2-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(3,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(3,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(3-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(3-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(4-bromo-2-fluorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(4-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(4-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one
-
2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
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
2-[3-[(2,4-dichlorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[3-[(2,4-difluorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[3-[(3,5-dimethylphenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[3-[(4-bromo-2-fluorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[3-[(4-bromophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[3-[(4-bromophenyl)methoxy]benzoyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate
-
3,4-dihydroxybenzoate
-
0.24 mM, 50% inhibition, noncompetitive
3,4-Dihydroxyphenylacetate
-
0.75 mM, 50% inhibition, noncompetitive
3,5-diiodo-4-hydroxyphenylpyruvate
-
0.25 mM, 50% inhibition, competitive
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
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
-
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione
-
3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
-
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
3-(2-hydroxyphenyl)propionate
-
50% inhibition above 10 mM, competitive
3-(3,4-dichlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(3-bbromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(3-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(3-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(3-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(3-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-bromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
3-(4-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(4-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
3-(furan-2-ylcarbonyl)-1,3-oxazolidin-2-one
-
-
3-(furan-2-ylcarbonyl)-1,3-thiazolidin-2-one
-
-
3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one
-
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
-
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
-
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
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
-
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
-
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
-
3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-(5-nitrobenzofuran-2-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one
3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(3-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(4-methoxyphenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(4-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(pentafluorophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
3-hydroxy-2-[3-[(4-isopropylphenyl)methoxy]-2-nitrobenzoyl]cyclohex-2-en-1-one
-
-
3-hydroxy-2-[3-[(4-methylphenyl)methoxy]-2-nitrobenzoyl]cyclohex-2-en-1-one
-
-
3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one
-
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-4-phenyl-2-furanone
-
0.0005 mM, 50% inhibition, may serve as a lead compound for further design of more potent inhibitors
3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one
3-hydroxy-5,5-dimethyl-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-5-methyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-5-methyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxyphenylpyruvate
-
competitive
3-methoxy-4-hydroxyphenylacetate
-
0.25 mM, 50% inhibition, competitive
3-methoxy-4-hydroxyphenylpyruvate
-
competitive
3-thienylpyruvate
-
mechanism-based inhibitor
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
-
3-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]-1,3-oxazolidin-2-one
-
-
3-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]-1,3-thiazolidin-2-one
-
-
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
-
3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one
-
-
3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one
-
-
3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one
-
-
3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one
-
-
3-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one
-
-
3-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one
-
-
4-(2,4-dichlorobenzyl)-1,3-dimethyl-5-hydroxypyrazole
-
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6-trimethyl-6-(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
4-(3-cyclohexylpropanoyl)-5-methoxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-acetyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-aminophenylpyruvate
-
competitive
4-decanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
4-dodecanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-hexanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
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
-
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
-
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
-
4-hydroxybenzaldehyde
-
50% inhibition above 10 mM, noncompetitive
4-hydroxytetrafluorophenylpyruvate
-
mechanism-based inhibitor
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-[(3-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
5-hydroxy-2,2,6,6-tetramethyl-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
-
5-hydroxy-2,2,6,6-tetramethyl-4-(2-phenylacetyl)cyclohex-4-ene-1,3-dione
-
5-hydroxy-2,2,6,6-tetramethyl-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione
-
5-hydroxy-2,2,6,6-tetramethyl-4-(3-phenylpropanoyl)cyclohex-4-ene-1,3-dione
-
5-hydroxy-2,2,6,6-tetramethyl-4-palmitoylcyclohex-4-ene-1,3-dione
-
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
5-hydroxy-4-isobutyryl-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
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
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
binding mode
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
binding mode
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(3-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-phenylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(3-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
6-[2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
6-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
7-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]-2H-1-benzopyran-2-one
-
8-Hydroxyquinoline-5-sulfonic acid
-
560 nM, 50% inhibition
Acetopyruvate
-
0.33 mM, 50% inhibition, competitive
Al3+
10 mM, 7% inhibition
Bathocuproine
-
3 mM, 50% inhibition
benzobicyclon hydrolysate
-
Ca2+
10 mM, 16% inhibition
Co2+
10 mM, 32% inhibition
Cu2+
10 mM, complete inhibition
Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
DEPC
1 mM, no residual activity
diethyl dicarbonate
-
5 mM, 50% inhibition
diketonitrile of isoxaflutole
-
half-site reactivity, nearly irreversible
DL-3,4-dihydroxyphenylalanine
-
0.32 mM, 50% inhibition, noncompetitive
DL-4-hydroxyphenyllactate
-
50% inhibition above 10 mM, competitive
DL-Epinephrine
-
0.17 mM, 50% inhibition, noncompetitive
DTT
10 mM, 61% inhibition
enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
ethanol
-
5% v/v, 50% inhibition, complete loss of activity at 20% v/v
L-Phe
-
10 mM, 50% inhibition, competitive
methyl 3-chloro-4-[(2-oxo-1,3-oxazolidin-3-yl)carbonyl]benzenesulfinate
-
-
methyl 3-nitro-4-[(2-oxo-1,3-oxazolidin-3-yl)carbonyl]benzenesulfinate
-
-
methyl 3-nitro-4-[(2-oxo-1,3-thiazolidin-3-yl)carbonyl]benzenesulfinate
-
-
Mg2+
10 mM, 18% inhibition
Mn2+
10 mM, 97% inhibition
Na+
10 mM, 14% inhibition
Ni2+
10 mM, 28% inhibition
o-hydroxyphenylpyruvate
-
competitive inhibitor of 4-hydroxyphenylpyruvate
oxaloacetate
-
10 mM, 50% inhibition, noncompetitive
pentafluorophenylpyruvate
-
competitive
phenylglyoxalate
-
50% inhibition above 10 mM, competitive
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
pyridoxal 5'-phosphate
-
2 mM, 50% inhibition
pyruvate
-
50% inhibition above 10 mM, competitive
SDS
2% (w/v), complete inhibition
tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
thiophenyl oxalate
-
competitive
Tiron
-
0.4 mM, 50% inhibition
trans-4-hydroxycinnamate
-
50% inhibition above 10 mM, competitive
triketone-rich fraction
-
-
Urea
1 M, 3% inhibition. 3 M, 42% inhibition. 5 M, 56% inhibition
YCl3
-
1 mM, 50% inhibition
Zn2+
10 mM, 65% inhibition
[1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone
50% inhibition at 12 nM
1,10-phenanthroline
-
-
1,10-phenanthroline
-
0.01 mM, 50% inhibition
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
50% inhibition at 7 nM
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
50% inhibition below 20 nM
2,2'-bipyridyl
-
-
2,2'-bipyridyl
-
1.8 mM, 50% inhibition
2,2'-bipyridyl
-
0.32 mM, 50% inhibition
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
-
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
potent linear competitive inhibitor
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
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
-
2-hydroxyphenylacetate
-
-
2-hydroxyphenylacetate
-
product inhibition
2-hydroxyphenylacetate
-
10 mM, 50% inhibition, noncompetitive
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
2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
herbicide, drug to treat inborn defects of tyrosine catabolism, specifically type I tyrosinemia and alkaptonuria
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
2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
-
3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one
-
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
3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one
-
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
4-hydroxyphenylpyruvate
-
enzyme form 2 and 3, no substrate inhibition is observed for enzyme form 1
4-hydroxyphenylpyruvate
-
-
4-hydroxyphenylpyruvate
substrate inhibition
4-hydroxyphenylpyruvate
-
above 0.2 mM; substrate inhibition
4-hydroxyphenylpyruvate
-
substrate inhibition
4-hydroxyphenylpyruvate
-
interaction of enol-4-hydroxyphenylpyruvate with enzyme-bound Fe3+, formed by autooxidation, causes the substrate inhibition
4-hydroxyphenylpyruvate
-
above 0.2 mM
4-hydroxyphenylpyruvate
-
-
bathophenanthroline
-
-
bathophenanthroline
-
0.018 mM, 50% inhibition; reactivation to 30% by dialysis and to 60% by addition to Fe2+
bathophenanthroline
-
0.012 mM, 50% inhibition
bicyclopyrone
-
Cupferron
-
-
Cupferron
-
0.0011 mM, 50% inhibition
Cupferron
-
0.0071 mM, 50% inhibition
DAS 645
strong inhibition
DAS 869
-
DAS 869
strong inhibition
diethyldithiocarbamate
-
-
diethyldithiocarbamate
-
0.0049 mM, 50% inhibition; restored by dialysis
diethyldithiocarbamate
-
-
diethyldithiocarbamate
-
0.0021 mM, 50% inhibition
Dithizone
-
-
Dithizone
-
0.14 mM, 50% inhibition
EDTA
10 mM, 76% inhibition
EDTA
1 mM, no residual activity
Fe2+
-
1 mM, 30% inhibition
Fe2+
10 mM, 82% inhibition
H2O2
-
10 nM, 60% inhibition. 0.001 mM, complete inhibition
H2O2
-
0.01 mM-1 mM, 5-15% inhibition
H2O2
-
10 mM, 30% inhibition
homogentisate
-
-
homogentisate
-
product inhibition
isoxaflutole
-
mesotrione
-
-
mesotrione
-
binding constant of 602 microM
mesotrione
mesotrione is an extremely potent competitive inhibitor of this enzyme
mesotrione
slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase
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
mesotrione
-
low inhibition, the isozyme is resistant to this herbicide
mesotrione
molecular docking and molecular dynamics simulation estimate the interacting regions of HPPD with mesotrione using structure PDB ID 3ISQ
mesotrione
binding free energy -12.26 kcal/mol
mesotrione
low inhibition
nitisinone
i.e. orfadin or NTBC, an effective herbicide
nitisinone
i.e. 2-[2-nitro-4-(trifluoromethyl) benzoyl]-1,3-cyclohexanedione, slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase
nitisinone
NBTC, in clinical use
nitisinone
binding free energy -10.97 kcal/mol. Residues Tyr221 and Leu224 are involved in the interaction between nitisinone and HPPD
nitisinone
-
i.e. orfadin or NTBC, addition of NTBC halts the morphology transition and stems pathogenesis in this organism
nitisinone
i.e. orfadin or NTBC, bidentate coordination of NTBC with the HPPD active site ferrous ion, enzyme-bound crystal structure, overview
NTBC
tauromers
NTBC
tauromers, strong inhibition of the two tautomers
phenylpyruvate
-
competitive
phenylpyruvate
-
non-competitive inhibition with 4-hydroxyphenylpyruvate as substrate
phenylpyruvate
-
0.53 mM, 50% inhibition, competitive
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).
sulcotrione
strong inhibition
sulcotrione
slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase
sulcotrione
binding free energy -8.07 kcal/mol
sulcotrione
low inhibition
tembotrione
-
tembotrione
binding free energy -8.51 kcal/mol
topramezone
-
additional information
high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors
-
additional information
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
design, synthesis, and herbicidal activity of triketone-quinoline hybrids as 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview. Computational modeling and CoMSIA analysis
-
additional information
-
design, synthesis, and herbicidal activity of triketone-quinoline hybrids as 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview. Computational modeling and CoMSIA analysis
-
additional information
efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview
-
additional information
-
efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview
-
additional information
enzyme inhibition mechanisms and binding structures, molecular docking study, overview
-
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
-
additional information
in silico structure-based virtual screening of four commercial databases to find inhibitors
-
additional information
in silico analization of 2-(aryloxyacetyl)cyclohexane-1,3-diones derivatives as valid HPPD inhibitors
-
additional information
-
the enzyme is molecular target of new families of potent herbicides
-
additional information
inhibition mechanism of enzyme HPPD, detailed overview
-
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
-
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
-
additional information
synthesis of pyrazole-benzimidazolone hybrids from DNS869 and droperidol, bioevaluation of pyrazole-benzimidazolone hybrids as human 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview
-
additional information
-
synthesis of pyrazole-benzimidazolone hybrids from DNS869 and droperidol, bioevaluation of pyrazole-benzimidazolone hybrids as human 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview
-
additional information
hydrophobicity-oriented drug design strategy based on the interactions between HPPD and the commercial drug NTBC to idientify inhibitors
-
additional information
-
hydrophobicity-oriented drug design strategy based on the interactions between HPPD and the commercial drug NTBC to idientify inhibitors
-
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
-
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
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
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
-
additional information
enzyme inhibition mechanisms and binding structures, molecular docking study, overview
-
additional information
not inhibitory at 1 mM: urea, PMSF
-
additional information
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
-
neither epoxybenzoaquinone ester nor 2-hydroxy-3-phenyl-3-butenoic acid is an inhibitor
-