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1.13.11.27: 4-hydroxyphenylpyruvate dioxygenase

This is an abbreviated version!
For detailed information about 4-hydroxyphenylpyruvate dioxygenase, go to the full flat file.

Word Map on EC 1.13.11.27

Reaction

4-hydroxyphenylpyruvate
+
O2
=
homogentisate
 +
CO2

Synonyms

4-HPPD, 4-hydroxyphenylpyruvare dioxygenase, 4-hydroxyphenylpyruvate dioxygenase, 4-hydroxyphenylpyruvic acid dioxygenase, 4HPPD, ASJ32_19370, At-HPPD, AtHPPD, AvHPPD-03, EC 1.14.2.2, EC 1.99.1.14, formerly, F Alloantigen, F protein, F-antigen homolog, HPD, hpdA, HPPD, HPPDase, Legiolysin, MsHPPD, oxygenase, 4-hydroxyphenylpyruvate di-, p-hydroxyphenyl pyruvate dioxygenase, p-hydroxyphenylpyruvate dioxygenase, p-hydroxyphenylpyruvate hydroxylase, p-hydroxyphenylpyruvate oxidase, p-hydroxyphenylpyruvic acid hydroxylase, p-hydroxyphenylpyruvic hydroxylase, p-hydroxyphenylpyruvic oxidase, PTO1369, Pt_Hpd, T-cell reactive protein, TF-AG, YS103B

ECTree

     1 Oxidoreductases
         1.13 Acting on single donors with incorporation of molecular oxygen (oxygenases)
             1.13.11 With incorporation of two atoms of oxygen
                1.13.11.27 4-hydroxyphenylpyruvate dioxygenase

Inhibitors

Inhibitors on EC 1.13.11.27 - 4-hydroxyphenylpyruvate dioxygenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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
-
1,10-phenanthroline
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
-
-
2,2'-bipyridyl
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-hydroxyphenylacetate
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-hydroxyphenylpyruvate
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
bathophenanthroline
benzobicyclon hydrolysate
-
bicyclopyrone
Ca2+
10 mM, 16% inhibition
citrate
-
-
Co2+
10 mM, 32% inhibition
Cu2+
10 mM, complete inhibition
Cupferron
Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
DAS 645
DAS 869
DEPC
1 mM, no residual activity
diethyl dicarbonate
-
5 mM, 50% inhibition
diethyldithiocarbamate
diketonitrile of isoxaflutole
-
half-site reactivity, nearly irreversible
Dithizone
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
Fe2+-chelators
-
-
-
homogentisate
isoxaflutole
K+
10 mM, 6% inhibition
L-Phe
-
10 mM, 50% inhibition, competitive
mesotrione
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
nitisinone
nitisonone
-
-
o-hydroxyphenylpyruvate
-
competitive inhibitor of 4-hydroxyphenylpyruvate
oxaloacetate
-
10 mM, 50% inhibition, noncompetitive
pentafluorophenylpyruvate
-
competitive
phenylglyoxalate
-
50% inhibition above 10 mM, competitive
phenylpyruvate
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
pyrasulfotole
-
-
pyridoxal 5'-phosphate
-
2 mM, 50% inhibition
pyruvate
-
50% inhibition above 10 mM, competitive
SDS
2% (w/v), complete inhibition
sulcotrione
tembotrione
tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
thiophenol oxalate
-
-
thiophenyl oxalate
-
competitive
Tiron
-
0.4 mM, 50% inhibition
topramezone
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
additional information
-