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(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
(4-hydroxyphenyl)-pyruvate + O2
homogentisate + CO2
-
-
-
-
?
2-thienylpyruvate + O2
? + CO2
-
-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
3-thienylpyruvate + O2
3-carboxymethyl-3-thiolene-2-one + CO2
-
-
-
?
4-fluorophenylpyruvate + O2
4-fluoro-2-hydroxyphenylacetate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
2,5-dihydroxyphenylacetate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
4-hydroxytetrafluorophenylpyruvate + O2
? + CO2
-
-
-
-
?
4-methylphenylpyruvate + O2
? + CO2
-
poor substrate
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
additional information
?
-
(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
-
-
-
?
(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
-
-
-
-
?
3,4-dihydroxyphenylpyruvate + O2
? + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
4-hydroxyphenylpyruvate dioxygenase does not use phenolpyruvate as a substrate in normal plant metabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
evidence against participation of a quinol as a free intermediate
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme is involved in production of homogentisate, the aromatic precursor of all phenylquinones
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Frog
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
activity with the keto-form of 4-hydroxyphenylpyruvate is 40times higher than with the enol tautomer
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
key enzyme involved in tyrosine catabolism, congenital 4-hydroxyphenylpyruvate dioxygenase deficiency is a rare, relatively benign condition known as hereditary type III tyrosinemia
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
the conversion of 4-hydroxyphenyl-pyruvate to homogentisate involves oxidative decarboxylation, side-chain migration and aromatic hydroxylation in a single catalytic cycle. The 4-HPPD reaction is unusual in that the 2-oxoacid and prime substrate moieties are contained within the same molecule
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
second step of oxidative tyrosine catabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
second step of oxidative tyrosine catabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
hppD is transcriptionally activated by HpdA and repressed by HpdR
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
best substrate
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme participates in catabolism of tyrosine
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
-
-
the wild-type enzyme produces 85% homogentisate and 15% 4-hydroxyphenylacetate
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
-
-
the wild-type enzyme produces 90% homogentisate, 1% quinolacetate, and 9% 4-hydroxyphenylacetate
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
-
-
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
at 10% of the activity with 4-hydroxyphenylpyruvate
-
-
?
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
-
substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed
-
-
?
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
-
substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed
-
-
?
additional information
?
-
no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate
-
-
?
additional information
?
-
-
no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate
-
-
?
additional information
?
-
no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate
-
-
?
additional information
?
-
-
HpdR positively regulates hpdA expression through direct binding to the HpdA promoter within a region containing two conserved direct repeat sequences. HpdR-dependent hpdA transcription occurs in the presence of 4-hydroxyphenylpyruvate, tyrosine, and phenylalanine, as well as during starvation
-
-
?
additional information
?
-
-
Single turnover kinetics are observed spectrophotometrically by mixing equal volumes of the anaerobic enzyme-substrate complex and solutions containing molecular oxygen in the presence of saturating HPP using a stopped-flow spectrophotometer. k1 = 7.4 x 100000 /M/s, k2 = 74 /s, k3 = 13.2 /s, k4 = 1.6 /s, indicating the accumulation of three catalytic intermediates. The kinetic data observed with substrate substituted with deutererons for aromatic protons are not significantly different from those observed with the proteo substrate. The final phase in catalysis (k4), decreases to 0.7 /s in the presence of deuterium oxide solvent, indicating the involvement of a solvent-derived proton in this step.
-
-
?
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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
-
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0.0013
(2,6-difluoro-4-hydroxyphenyl)pyruvate
-
-
0.000102
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5,7-dichlorobenzofuran-2-yl)methanone
30°C, pH not specified in the publication
-
0.000099
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5-nitrobenzofuran-2-yl)methanone
30°C, pH not specified in the publication
-
0.000223
(5,7-dichlorobenzofuran-2-yl)(5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanone
30°C, pH not specified in the publication
-
0.000458
1-benzyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000355
1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000028
1-butyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000019
1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000045
1-ethyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000047
1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000005
1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000203 - 0.000327
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
0.000139
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000082
2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000029
2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000304
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000076
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0000098
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
-
0.000025
2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0001
2-(5,7-dichlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
30°C, pH not specified in the publication
-
0.000074
2-(5-chlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
30°C, pH not specified in the publication
-
0.000017
2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021 - 0.000055
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
0.000014
2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000011
2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000222
2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000011
2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000041
2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000291
2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000072
2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000626
2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000055
2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0000039
2-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
pH not specified in the publication, 25°C
-
0.000113
2-[(2,3-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000088
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000066
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000242
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.004803
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000197
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000043
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000121
2-[(2,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000045
2-[(2,6-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000034
2-[(2-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002141
2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001143
2-[(2-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000267
2-[(3,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000956
2-[(3,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000075
2-[(3-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000078
2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000351
2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002001
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00011
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000037
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000031
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000029
2-[(4-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000208 - 0.000547
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
0.000213
2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000189
2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00393
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002831
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000369
2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000161
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000059
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0000242
3-(2,6-dimethylphenyl)-1-methyl-6-(2-oxidanyl-6-oxidanylidene-cyclohexen-1-yl)carbonyl-quinazoline-2,4-dione
pH 7, 25°C
-
0.000087
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000011
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000024
3-(2-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000109
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00009
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000015
3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000023
3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021
3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000086
3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
3-(2-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000081
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00017
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000079
3-(2-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000015
3-(2-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000008
3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000007
3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000025
3-(3,4-dichlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000093
3-(3-bbromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000014
3-(3-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000033
3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000027
3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000173
3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00001
3-(3-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00009
3-(3-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00002
3-(3-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00013
3-(4-bromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000018
3-(4-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000177
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000032
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000115
3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000023
3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000237
3-(4-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
3-(4-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000219
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00004
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000247
3-(4-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000034
3-(4-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000007
3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000016
3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000028
3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000039
3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000009
3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000074
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000298
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000099
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000024
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00003
3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000341
3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000062
3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000171
3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000095
3-hydroxy-2-(5-nitrobenzofuran-2-carbonyl)cyclohex-2-en-1-one
30°C, pH not specified in the publication
-
0.001243
3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000075
3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000184
3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000077
3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000894
3-hydroxy-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000045
3-hydroxy-2-[(2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000623
3-hydroxy-2-[(3-methylphenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000301
3-hydroxy-2-[(4-methoxyphenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000069
3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000988
3-hydroxy-2-[(4-methylphenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000055
3-hydroxy-2-[(pentafluorophenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000035
3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000009
3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000132
3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00002
3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000215
3-hydroxy-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000253
3-hydroxy-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000598
3-hydroxy-2-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000134
3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000561
3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000544
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000354
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001052
3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001133
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000079
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.005571
3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001596
3-hydroxy-5,5-dimethyl-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003556
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003662
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001298
3-hydroxy-5-methyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003615
3-hydroxy-5-methyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000007
3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.4 - 1.9
4-hydroxyphenylpyruvate
0.000112
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000408
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000245
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000038
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000054
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
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000043
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000668
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000024
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000067
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000042
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000039
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000032
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000141
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000017
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000033
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000015
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000627
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000074
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000248
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000156
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000207
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000238
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000031
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(3-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00016
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000013
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000058
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000025
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000019
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-phenylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000038
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000034
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(3-methoxyphenyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00006
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002335
6-[2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000815
6-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003152
7-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]-2H-1-benzopyran-2-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.006
isoxaflutole
pH 6, 35°C
0.0000045 - 0.0236
mesotrione
0.0000064 - 0.000046
nitisinone
0.014
pentafluorophenylpyruvate
-
-
0.0137
pinocembrin
-
pH and temperature not specified in the publication
0.0000044
pyrasulfotole
pH not specified in the publication, 25°C
-
0.00000096 - 0.007
sulcotrione
0.001 - 0.0058
tembotrione
0.15
thiophenol oxalate
-
-
0.0025
topramezone
pH 6, 35°C
additional information
additional information
-
0.000203
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
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000327
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
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000055
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000208
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000547
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.4
4-hydroxyphenylpyruvate
-
about, enzyme form 3
0.7
4-hydroxyphenylpyruvate
-
about, enzyme form 2
1.9
4-hydroxyphenylpyruvate
pH 7.0, 50°C
0.0000045
mesotrione
pH not specified in the publication, 25°C
0.0000046
mesotrione
pH 7, 25°C
0.00001
mesotrione
pH 7, 30°C
0.000013
mesotrione
pH 7.0, 30°C, recombinant His-tagged enzyme
0.000013
mesotrione
-
pH 7.0, 30°C, recombinant His-tagged enzyme
0.000013
mesotrione
pH 7.0, 30°C, recombinant His-tagged enzyme
0.00002
mesotrione
30°C, pH not specified in the publication
0.000068 - 0.0236
mesotrione
dependent on the system used, overview. pH and temperature not specified in the publication
0.0013
mesotrione
pH 6, 35°C
0.0000064
nitisinone
pH 7, 25°C
0.000037
nitisinone
pH 7.0, 30°C, recombinant His-tagged enzyme
0.000046
nitisinone
pH 7, 30°C
0.00000096
sulcotrione
pH 7, 25°C
0.007
sulcotrione
pH 7, 30°C
0.001
tembotrione
pH 6, 35°C
0.0058
tembotrione
pH 7, 30°C
additional information
additional information
-
-
-
additional information
additional information
-
-
-
additional information
additional information
-
-
-
additional information
additional information
inhibition kinetics
-
additional information
additional information
-
inhibition kinetics
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.00094
1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021
1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00013
1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00064
1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00017
1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00093
1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00013
1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00022
1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00097
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00074
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000039
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00015
1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00099
1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00068
2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione
Homo sapiens
pH 7.0, 30°C, recombinant His-tagged enzyme
0.00009
2-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00011
2-[(2-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.0001
2-[(3-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00011
2-[(4-bromo-2-fluorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00012
2-[(4-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.000063
2-[3-[(2,4-dichlorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
Homo sapiens
pH 7, 30°C
-
0.000095
2-[3-[(2,4-difluorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
Homo sapiens
pH 7, 30°C
-
0.000068
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
Homo sapiens
pH 7, 30°C
-
0.000068
2-[3-[(4-bromo-2-fluorophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
Homo sapiens
-
pH 7, 30°C
-
0.000047
2-[3-[(4-bromophenyl)methoxy]-2-nitrobenzoyl]-3-hydroxycyclohex-2-en-1-one
Homo sapiens
pH 7, 30°C
-
0.000091
2-[3-[(4-bromophenyl)methoxy]benzoyl]-3-hydroxycyclohex-2-en-1-one
Homo sapiens
pH 7, 30°C
-
0.00097
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00088
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000064
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000273
3-hydroxy-2-(3,5,6-trichloro-4-((4-chlorobenzyl)amino)picolinoyl)cyclohex-2-en-1-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.000047
3-hydroxy-2-(3,5,6-trichloro-4-((4-isopropylbenzyl)amino)picolinoyl)cyclohex-2-en-1-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.000077
3-hydroxy-2-(3,5,6-trichloro-4-((4-methylbenzyl)amino)-picolinoyl)cyclohex-2-en-1-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.00007
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
Homo sapiens
pH 7, 30°C
-
0.00007
3-hydroxy-2-[3-[(4-methylphenyl)methoxy]-2-nitrobenzoyl]cyclohex-2-en-1-one
Homo sapiens
-
pH 7, 30°C
-
0.00675
4-(2,4-dichlorobenzyl)-1,3-dimethyl-5-hydroxypyrazole
Coptis japonica var. dissecta
recombinant enzyme
0.00017
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00227
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6-trimethyl-6-(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00041
4-(3-cyclohexylpropanoyl)-5-methoxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.000019
4-decanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00025
4-dodecanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00096
4-hexanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00249
4-hydroxy-6-methyl-3-[(2E)-3-phenylprop-2-enoyl]-2H-pyran-2-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.00072
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00271
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00094
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00119
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00099
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00103
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00004
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00014
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000061
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000077
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0001
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-[(3-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00025
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000059
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0143
5-hydroxy-2,2,6,6-tetramethyl-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.0189
5-hydroxy-2,2,6,6-tetramethyl-4-(2-phenylacetyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.0118
5-hydroxy-2,2,6,6-tetramethyl-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00075
5-hydroxy-2,2,6,6-tetramethyl-4-(3-phenylpropanoyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
grandiflorone, most active naturally occurring beta-triketone
0.00031
5-hydroxy-2,2,6,6-tetramethyl-4-palmitoylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.0445
5-hydroxy-4-isobutyryl-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
0.00234
benzobicyclon hydrolysate
Coptis japonica var. dissecta
recombinant enzyme
0.0000051 - 0.000043
bicyclopyrone
0.0001
Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000012 - 0.00002
DAS 645
0.00067
enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0000013 - 0.0087
isoxaflutole
0.0000018 - 0.0042
mesotrione
0.000085
nitisonone
Homo sapiens
pH 7, 30°C
-
0.0731
pinocembrin
Sus scrofa
-
pH and temperature not specified in the publication
0.0014
pyrasulfotole
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.0000017 - 0.000094
sulcotrione
0.0000022 - 0.0025
tembotrione
0.0001
tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0000013 - 0.0052
topramezone
additional information
3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate
0.0000051
bicyclopyrone
Arabidopsis thaliana
wild-type, pH 7, 20°C
0.000015
bicyclopyrone
Arabidopsis thaliana
mutant M335H/P336A/E363Q, pH 7, 20°C
0.000023
bicyclopyrone
Zea mays
-
pH 7, 20°C
0.000043
bicyclopyrone
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.000012
DAS 645
Arabidopsis thaliana
pH and temperature not specified in the publication
0.00002
DAS 645
Rattus norvegicus
below, pH and temperature not specified in the publication
0.0000013
isoxaflutole
Arabidopsis thaliana
wild-type, pH 7, 20°C
0.0000025
isoxaflutole
Arabidopsis thaliana
mutant M335H/P336A/E363Q, pH 7, 20°C
0.0000075
isoxaflutole
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.000042
isoxaflutole
Zea mays
-
pH 7, 20°C
0.0087
isoxaflutole
Sphingobium sp.
pH 6, 35°C
0.0000018
mesotrione
Arabidopsis thaliana
wild-type, pH 7, 20°C
0.0000027
mesotrione
Arabidopsis thaliana
mutant M335H/P336A/E363Q, pH 7, 20°C
0.0000068
mesotrione
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.000027
mesotrione
Arabidopsis thaliana
pH and temperature not specified in the publication
0.000062
mesotrione
Zea mays
-
pH 7, 20°C
0.00023
mesotrione
Arabidopsis thaliana
pH not specified in the publication, 25°C
0.000273
mesotrione
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
0.0042
mesotrione
Sphingobium sp.
pH 6, 35°C
0.00004
NTBC
Rattus norvegicus
pH and temperature not specified in the publication
0.00005
NTBC
Arabidopsis thaliana
pH and temperature not specified in the publication
0.0000017
sulcotrione
Arabidopsis thaliana
wild-type, pH 7, 20°C
0.0000041
sulcotrione
Arabidopsis thaliana
mutant M335H/P336A/E363Q, pH 7, 20°C
0.000012
sulcotrione
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.000022
sulcotrione
Arabidopsis thaliana
pH and temperature not specified in the publication
0.000094
sulcotrione
Zea mays
-
pH 7, 20°C
0.0000022
tembotrione
Arabidopsis thaliana
wild-type, pH 7, 20°C
0.000004
tembotrione
Arabidopsis thaliana
mutant M335H/P336A/E363Q, pH 7, 20°C
0.0000087
tembotrione
Zea mays
-
pH 7, 20°C
0.00001
tembotrione
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.0025
tembotrione
Sphingobium sp.
pH 6, 35°C
0.0000013
topramezone
Arabidopsis thaliana
wild-type, pH 7, 20°C
0.0000016
topramezone
Arabidopsis thaliana
mutant M335H/P336A/E363Q, pH 7, 20°C
0.0000061
topramezone
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.0000072
topramezone
Zea mays
-
pH 7, 20°C
0.000015
topramezone
Setaria faberi
-
enzyme isolated from Setaria faberi
0.000023
topramezone
Setaria faberi
-
enzyme recombinantly expressed in Arabidopsis thaliana
0.0052
topramezone
Sphingobium sp.
pH 6, 35°C
additional information
3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate
Arabidopsis thaliana
IC50 value above 50 microM
additional information
3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one
Arabidopsis thaliana
IC50 value above 50 microM
additional information
3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
4-acetyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
4-acetyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
additional information
Arabidopsis thaliana
IC50 values: 0.015 mg/ml for manuka oil, 0.00402 mg/ml for triketone-rich fraction, 0.00314 mg/ml for leptospermone and 0.00022 mg/ml for grandiflorone
-
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evolution
-
4-hydroxyphenylpyruvate dioxygenase and hydroxymandelate synthase, HMS, EC 1.13.11.46, catalyze similar reactions using the same substrates, 4-hydroxyphenylpyruvate and dioxygen. Initially, both enzymes reduce and activate dioxygen in order to decarboxylate 4-hydroxyphenylpyruvate, yielding 4-hydroxyphenylacetate, CO2, and an activated oxo intermediate Both enzymes then hydroxylate 4-hydroxyphenylacetate but do so in different positions
evolution
the enzyme belongs to the non-haem Fe(II)/2-oxoacid-dependent oxygenase superfamily, which couples the oxidative decarboxylation of a 2-oxoacid (most commonly a-ketoglutarate) to the oxidation of the prime substrate
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
-
malfunction
deficiency in active 4-HPPD in humans results in type III tyrosinemia, a rare autosomal recessive disorder
malfunction
inhibition of HPPD can effectively alleviate the symptoms of type I tyrosinemia
malfunction
mutant plants with null alleles of HPPD are reported to exhibit a lethal photobleaching phenotype. MsHPPD expression in three MsHPPD-overexpressing transgenic lines and wild-type, overview
malfunction
neutrophil preparations from a patient with tyrosinemia type III, with inherited deficiency of 4-hydroxyphenylpyruvate dioxygenase (HPPD), exhibit a far higher NO release than controls, when NO is estimated in terms of nitrite content in the suspending media. L-tyrosine increases nitrite release and accumulation in suspending media of U-937 cells, a human monoblast-like lymphoma cell line which displays many characteristics of macrophages, including the expression of inducible and endothelial nitric oxide synthases. The increase of nitrite release by patient's neutrophils might be related to the presence of high L-tyrosine concentrations in the blood samples rather than to HPPD deficiency of in these cells
malfunction
when HPPD is inhibited, the plant is severely damaged by sunlight, becoming bleached and eventually undergoing necrosis and death. HPPD inhibitors are termed bleaching herbicides
metabolism
-
inhibition mechanism of 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
metabolism
enzyme 4-HPPD catalyzes the second step in the pathway of tyrosine catabolism, the conversion of 4-hydroxyphenyl-pyruvate to homogentisate
metabolism
second step of oxidative tyrosine catabolism
metabolism
4-ydroxyphenylpyruvate dioxygenase (HPPD) is an essential enzyme in tyrosine catabolism
metabolism
enzyme HPPD is the first committed enzyme involved in the biosynthesis of vitamin E. Vitamin E is not a single compound, but rather the collective name for a group of eight lipid-soluble antioxidants consisting of a polar chromanol head group and a hydrophobic prenyl tail, which are derived from the methylerythritol-4-phosphate (MEP) and shikimate pathways. Four of these compounds are termed tocopherols, and the other four are termed tocotrienols, and depending on the saturation level of the hydrophobic tail and also the number and position of the methyl groups on the chromanol ring, members of the vitamin E group are classified into alpha-, beta-, gamma- and delta-forms. In plants, the production of HGA is the first step in tocopherol synthesis, and homogentisic acid (HGA) is synthesized from p-hydroxyphenyl pyruvate (HPP) in a reaction catalyzed by enzyme HPPD
metabolism
hydroxyphenylpyruvate dioxygenase catalyzes the second step in the pathway of L-tyrosine catabolism, the conversion of 4-hydroxyphenylpyruvate to homogentisate
metabolism
-
suggested hydroxylation mechanisms for HMS and HPPD and pathways leading to alternative products: oxepinone and quinolacetate
metabolism
-
the enzyme is involved in the second step of the tyrosine degradation pathway, catalyzing the conversion of 4-hydroxyphenylpyruvate to homogentisate
metabolism
-
the enzyme is ivolved in the tyrosine catabolic pathway, it catalyzes the synthesis of the central compound homogentisate and plays an important role, overview
metabolism
-
suggested hydroxylation mechanisms for HMS and HPPD and pathways leading to alternative products: oxepinone and quinolacetate
-
metabolism
-
second step of oxidative tyrosine catabolism
-
physiological function
Vitis vinifera x Vitis vinifera
-
involved in aromatic amino acid metabolism
physiological function
-
involved in aromatic amino acid metabolism
physiological function
4-hydroxyphenylpyruvate dioxygenase is involved in vitamin E biosynthesis and abscisic acid-mediated seed germination in Medicago sativa. MsHPPD functions not only in the vitamin E biosynthetic pathway, but also plays a critical role in seed germination via affecting abscisic acid biosynthesis and signaling, overview. HPPD is essential for plant viability
physiological function
-
enzyme HPPD activity is one of the key factors influencing the production of tocopherols, overview
physiological function
-
enzyme HPPD is upregulated during the hyphal to yeast morphological transition that occurs when Paracoccidiodes brasiliensis fungus becomes pathogeneic
physiological function
the enzyme catalyzes the synthesis of homogentisate, a precursor of plastoquinone, a diene-dione molecule, that serves as a lipid soluble electron carrier linking photosystems and shuttling electrons through the electron transport chain. Homogentiate is also the precursor to tocopherols (vitamin E) that serve as antioxidants and plant hormones. As such photosynthetic life is inseparably dependent on tyrosine catabolism and nature has developed a number of allelopathic molecules that target HPPD and thus homogenetisate production
physiological function
heterologous expression results in thermosensitive pigmentation in Escherichia coli. The thermolability of HppD is responsible for the temperature-dependent melanization of Aeromonas salmonicida subsp. salmonicida
physiological function
HPD promotes tyrosine catabolism leading to increased acetyl-CoA levels, the source of histone acetylation, and also stimulates histone deacetylase 10 translocation from the nucleus into the cytoplasm mediated by tumor suppressor liver kinase B1-AMP-activated protein kinase signaling
physiological function
-
Hppd participates in the catabolism of tyrosine and promotes pyomelanin production in Escherichia coli BL21. Injcetion of Apostichopus japonicus with the Hppd shows significantly stimulatory effects on the expression of oxidative stress related genes catalase, glutathione S-transferase, glutathione peroxidase, heat shock protein 70. At 48 h, the expression level of cytochrome P450 is down-regulated compared with cells treated with BSA
physiological function
-
L-tyrosine catabolism plays a key role in pigment production in the test bacteria. The isolate produces deep brown pigments belonging to the pyomelanin group
physiological function
L-tyrosine catabolism plays a key role in pigment production in the test bacteria. The isolate produces deep brown pigments belonging to the pyomelanin group
physiological function
L-tyrosine catabolism plays a key role in pigment production in the test bacteria. The isolate produces deep brown pigments belonging to the pyomelanin group
additional information
-
substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Residues Ser201, Asn216, Gln225, Gln239, and Gln309 are important for catalysis
additional information
-
substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Residues Ser201, Asn216, Gln226, Gln230, and Gln305 are important for catalysis
additional information
-
substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Residues Ser260, Asn275, Gln286, Gln300, and Gln372 are important for catalysis
additional information
-
substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Three different models of HPP binding within the Arabidopsis thaliana HPPD active site. Residues Ser246, Asn261, Gln272, Gln286, and Gln358 are important for catalysis
additional information
the disordered C-terminal tail of the enzyme, which is extended C-terminus compared to other 4-HPPD enzymes, plays an important role in catalysis with a critical role of residue Q375 in orientating the tail and ensuring the conformation of the terminal alpha-helix to maintain the integrity of the active site for catalysis. The active site of 4-HPPD is enclosed by a C-terminal alpha-helix which is assumed to function as a gate which controls access of substrate. Interactions provided by Q375 to hold the terminal helix and the tail in proper position are critical for isolating the active site from solvent during catalysis, enzyme structure modeling, overview
additional information
-
the disordered C-terminal tail of the enzyme, which is extended C-terminus compared to other 4-HPPD enzymes, plays an important role in catalysis with a critical role of residue Q375 in orientating the tail and ensuring the conformation of the terminal alpha-helix to maintain the integrity of the active site for catalysis. The active site of 4-HPPD is enclosed by a C-terminal alpha-helix which is assumed to function as a gate which controls access of substrate. Interactions provided by Q375 to hold the terminal helix and the tail in proper position are critical for isolating the active site from solvent during catalysis, enzyme structure modeling, overview
additional information
enzyme molecular docking study using crystal structure PDB ID 1SQI
additional information
enzyme molecular docking study using crystal structure PDB ID 1TG5. Three amino acid residues compose the active site: Gln358, His205 and Phe398
additional information
-
enzyme structure analysis, overview
additional information
-
enzyme structure analysis, overview
additional information
enzyme structure analysis, overview
additional information
enzyme structure analysis, overview
additional information
enzyme structure analysis, overview
additional information
-
molecular dynamics simulations are performed for the HPPD-Fe(IV)=O-hydroxyphenylacetate complex in order to obtain a reliable starting structure for quantum mechanics/molecular mechanics calculations of ring hydroxylation and coupled rearrangement reactions catalyzed by the enzyme HPPD, structure of HPPD-Fe(II)-acetate complex, structure homology modeling, overview
additional information
-
molecular dynamics simulations are performed for the HPPD-Fe(IV)=O-hydroxyphenylacetate complex in order to obtain a reliable starting structure for quantum mechanics/molecular mechanics calculations of ring hydroxylation and coupled rearrangement reactions catalyzed by the enzyme HPPD, structure of HPPD-Fe(II)-acetate complex, structure homology modeling, overview
-
additional information
-
enzyme structure analysis, overview
-
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L119P
mutation increases the thermostability of the enzyme
P103Q
mutation increases the thermostability of the enzyme
P103Q/L119P
mutation enables recombinant Escherichia coli strains to form melanin at 30°C and 37°C
P117L
Escherichia coli cells expressing the mutant form pigment at all tested temperatures
Q101P
Escherichia coli cells expressing the mutant fail to form pigment at all 37°C
Q101P/P117L
Escherichia coli cells expressing the mutant form pigment at all tested temperatures
S18T
mutation increases the thermostability of the enzyme
S18T/L119P
mutation enables recombinant Escherichia coli strains to form melanin at 30°C
S18T/P103Q
mutation enables recombinant Escherichia coli strains to form melanin at 30°C and 37°C
S18T/P103Q/L119P
mutation enables recombinant Escherichia coli strains to form melanin at 30°C and 37°C
T16S
Escherichia coli cells expressing the mutant form pigment at all tested temperatures
T16S/P117L
Escherichia coli cells expressing the mutant form pigment at all tested temperatures
T16S/Q101P
Escherichia coli cells expressing the mutant form pigment at all tested temperatures
T16S/Q101P/P117L
Escherichia coli cells expressing the mutant completely lose melanin formation ability at 30°C and 37°C
F381A
residue is involved in substrate binding
M335H/P336A/E363Q
residues 336 and 363 are substituted by the corresponding residues of Zea mays HPPD, more than twofold increase in IC50 for sulcotrione and tembotrione. Increased herbicide tolerance compared to wild-type matches with a clear shift in the free energy profile toward favoring the closed helix H11 state
M335H/P336A/P339T/T341D/E363Q/E426Q
substitutions correspond to residues found in Zea mays. The mutant has a clear preference for the closed H11 state
N261D
-
site-directed mutagenesis, during the reaction mechanism, the last 1,2 rearrangement is blocked in S246A HPPD mutant, so that an arene oxide-derived intermediate is released as an alternative product, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
N282A
residue is involved in substrate binding
N423A
residue is involved in substrate binding
P315R/R328A/L347M
mutations induce an 8fold increase in the value of k4 in respect of mesotrione
Q272E
-
site-directed mutagenesis, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
Q286E
-
site-directed mutagenesis, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
Q293A
residue is involved in substrate binding
Q307A
residue is involved in substrate binding
Q358E
-
site-directed mutagenesis, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
S246A
-
site-directed mutagenesis, during the reaction mechanism, the last 1,2 rearrangement is blocked in S246A HPPD mutant, so that an arene oxide-derived intermediate is released as an alternative product, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
S267A
residue is involved in substrate binding
A327R/L359M
-
about 90% of wild-type activity
G411A
-
about 15% of wild-type activity
G413W
-
about 20% of wild-type activity
L359M
-
about 80% of wild-type activity
V218I/A327R/I340E/L359M
-
about 165% of wild-type activity
V218I/A327R/I340E/L359M/G411A
-
about 6% of wild-type activity
V218I/A327R/L359M
-
about 80% of wild-type activity
V218L/A327R/I340E/L359M
-
about 170% of wild-type activity
N275D
-
site-directed mutagenesis
Q286E
-
site-directed mutagenesis
Q300E
-
site-directed mutagenesis
Q372E
-
site-directed mutagenesis
S260A
-
site-directed mutagenesis
E12A
2fold decrease in catalytic efficiency
E254D
site-directed mutagenesis, the mutant shows 5% remaining activity compared to the wild-type enzyme
K10A
2fold decrease in catalytic efficiency
L224A
binding ability of the mutant to nitisinone is significantly weaker than that of wild-type
N363A
about 20% of wild-type activity
N363D
about 6% of wild-type activity
N363Q
about 7% of wild-type activity
P11A
30% increase in catalytic efficiency
Q251E
almost complete loss of activity
Q265E
about 5% of wild-type activity
Q334A
relative activity and substrate-binding affinity are preserved
Q334A/N363D
about 5% of wild-type activity
Q334A/N363Q
about 3% of wild-type activity
Q334N
about 3% of wild-type activity
Q334N/N363Q
about 2% of wild-type activity
Q375N
site-directed mutagenesis, the mutant shows that a solvent accessible channel opens to the putative substrate binding site, suggesting this is responsible for the complete loss of activity, modeling, overview. Inactive mutant
Q375N/R378K
site-directed mutagenesis, inactive mutant
R378K
site-directed mutagenesis, the mutant shows 5% remaining activity compared to the wild-type enzyme
Y221A
binding ability of the mutant to nitisinone is significantly weaker than that of wild-type
P214T
-
site-directed mutagenesis, during hte reaction mechanism, the last 1,2 rearrangement is blocked in S246A HPPD mutant, so that an arene oxide-derived intermediate is released as an alternative product
synthesis
-
recombinant Escherichia coli expression HppD can produce pyomelanin at levels up to 315.5 mg/l (13.1 mg/l/h) in 24 h. Highest pyomelanin production is achieved when L-tyrosine and 0.5mM Cu2+ are supplemented into LB medium
E322R
-
mutant shows improved resistance to topramezone, with about 98% of wild-type activity, and displays increased resistance to mesotrione
K249R
-
mutant shows improved resistance to topramezone, with about 98% of wild-type activity, and displays increased resistance to mesotrione and DKN, i.e. the active ingredient of isoxaflutole
F337I
0.67 of wild-type activity
F341Y
16.9% of wild-type activity
F364I
-
site-directed mutagenesis, the mutant enzyme produces 47% homogentisate, 15% 4-hydroxyphenylacetate, and 19% quinolacetate, which differs from the wild-type activity
N216I
0.15% of wild-type activity
N216I/F337I/F341Y
inactive
N245D
-
site-directed mutagenesis, the mutant enzyme produces 52% homogentisate and 26.8% 4-hydroxyphenylacetate, and 21.2% quinolacetate, which differs from the wild-type activity
N245I
-
site-directed mutagenesis, the mutant enzyme produces 13% homogentisate and 87% 4-hydroxyphenylacetate, which differs from the wild-type activity
P214T
1.6% of wild-type activity
P214T/F337I/F341Y
inactive
P214T/N216I/F337I
inactive
P214T/N216I/F337I/F341Y
inactive
P214T/N216I/F341Y
inactive
N245S
-
site-directed mutagenesis, the mutant produces quinolacetic acid as reaction product
-
M335H/P336A/E363Q
-
residues 336 and 363 are substituted by the corresponding residues of Zea mays HPPD, more than twofold increase in IC50 for sulcotrione and tembotrione. Increased herbicide tolerance compared to wild-type matches with a clear shift in the free energy profile toward favoring the closed helix H11 state
M335H/P336A/P339T/T341D/E363Q/E426Q
-
substitutions correspond to residues found in Zea mays. The mutant has a clear preference for the closed H11 state
N245Q
-
site-directed mutagenesis, the mutant enzyme produces 44.5% homogentisate and 52% 4-hydroxyphenylacetate, and 4% quinolacetate, which differs from the wild-type activity
N245Q
-
site-directed mutagenesis, the mutant enzyme produces 52% homogentisate and 45% 4-hydroxyphenylacetate, and 3% quinolacetate, which differs from the wild-type activity
N245S
-
site-directed mutagenesis, the mutant enzyme produces 3.4% homogentisate and 6.6% 4-hydroxyphenylacetate, and 90% quinolacetate, which differs from the wild-type activity
N245S
site-directed mutagenesis, the mutant produces quinolacetic acid as reaction product
P243T
-
site-directed mutagenesis, the mutant enzyme produces 13% homogentisate, 8.7% 4-hydroxyphenylacetate, and 78% quinolacetate, which differs from the wild-type activity
P243T
-
site-directed mutagenesis, the mutant enzyme produces 8.4% homogentisate, 46.5% 4-hydroxyphenylacetate, and 45% quinolacetate, which differs from the wild-type activity
S230A
-
site-directed mutagenesis, the mutant enzyme produces 11.6% homogentisate, 30.6% 4-hydroxyphenylacetate, and 57.8% quinolacetate, which differs from the wild-type activity
S230A
-
site-directed mutagenesis, the mutant enzyme produces 7% homogentisate, 57% 4-hydroxyphenylacetate, and 36% quinolacetate, which differs from the wild-type activity
additional information
human 4-HPPD possesses an extended C-terminus compared to other 4-HPPD enzymes. Successive truncation of the disordered tail which follows the final alpha-helix results in no changes in the Km value for 4-HPP substrate but the kcat values are significantly reduced by ca. 25 to 50%. The different conformation of E254, R378 and Q375 in the final helix might be the cause of the activity loss
additional information
-
human 4-HPPD possesses an extended C-terminus compared to other 4-HPPD enzymes. Successive truncation of the disordered tail which follows the final alpha-helix results in no changes in the Km value for 4-HPP substrate but the kcat values are significantly reduced by ca. 25 to 50%. The different conformation of E254, R378 and Q375 in the final helix might be the cause of the activity loss
additional information
construction of a nanobiosensor based on HPPD for mesotrione detection. The atomic force microscope tip functionalization with HPPD immobilized in self-assembled monolayers is confirmed by fluorescence microscopy and atomic force spectroscopy. The cross-linker N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride is responsible for properly preserving the enzyme on the tip
additional information
upon removal of the 12 N-terminal residues, the kcat/Km decreases 8fold compared to wild-type. The wild-type level of activity is retained in a mutant missing the 17 N-terminal residues, with a kcat/Km 11fold higher than that of the mutant lacking 12 N-terminal residues, however, the structural stability of this mutant is lower than that of wild type
additional information
-
upon removal of the 12 N-terminal residues, the kcat/Km decreases 8fold compared to wild-type. The wild-type level of activity is retained in a mutant missing the 17 N-terminal residues, with a kcat/Km 11fold higher than that of the mutant lacking 12 N-terminal residues, however, the structural stability of this mutant is lower than that of wild type
additional information
heterologous overexpression of gene MsHPPD in Arabidopsis thaliana significantly increases the level of beta-tocotrienol and the total vitamin E content in Arabidopsis seeds. The transgenic Arabidopsis seeds exhibit an accelerated germination time, compared with wild-type seeds under normal conditions, as well as under NaCl and abscisic acid treatments. The expression level of several genes associated with abscisic acid biosynthesis (NCED3, NCED5, and NCED9) and the abscisic acid signaling pathway (RAB18, ABI3, and ABI5) are significantly downregulated in MsHPPD-overexpressing transgenic lines, as well as the total free abscisic acid content, phenotype. MsHPPD expression in three MsHPPD-overexpressing transgenic lines and wild-type, overview. Expression levels of ABA biosynthesis and ABA signaling pathway genes in MsHPPD-overexpressing transgenic Arabidopsis thaliana
additional information
-
heterologous overexpression of gene MsHPPD in Arabidopsis thaliana significantly increases the level of beta-tocotrienol and the total vitamin E content in Arabidopsis seeds. The transgenic Arabidopsis seeds exhibit an accelerated germination time, compared with wild-type seeds under normal conditions, as well as under NaCl and abscisic acid treatments. The expression level of several genes associated with abscisic acid biosynthesis (NCED3, NCED5, and NCED9) and the abscisic acid signaling pathway (RAB18, ABI3, and ABI5) are significantly downregulated in MsHPPD-overexpressing transgenic lines, as well as the total free abscisic acid content, phenotype. MsHPPD expression in three MsHPPD-overexpressing transgenic lines and wild-type, overview. Expression levels of ABA biosynthesis and ABA signaling pathway genes in MsHPPD-overexpressing transgenic Arabidopsis thaliana
additional information
construction and complementation of melA mutants of Shewanella oneidensis MR-1, in-frame deletion mutagenesis
additional information
-
construction and complementation of melA mutants of Shewanella oneidensis MR-1, in-frame deletion mutagenesis
additional information
-
construction and complementation of melA mutants of Shewanella oneidensis MR-1, in-frame deletion mutagenesis
-
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