Application | Comment | Organism |
---|---|---|
agriculture | 4-hydroxyphenylpyruvate dioxygenase is one of the most promising target sites for herbicide discovery | Arabidopsis thaliana |
drug development | 4-hydroxyphenylpyruvate dioxygenase is one of the most promising target sites for herbicide discovery | Arabidopsis thaliana |
Cloned (Comment) | Organism |
---|---|
gene HPD, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) | Arabidopsis thaliana |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
1-benzyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | binding mode | Arabidopsis thaliana | |
1-butyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
1-ethyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | binding mode | Arabidopsis thaliana | |
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 | - |
Arabidopsis thaliana | |
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
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 | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | binding mode | Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione | - |
Arabidopsis thaliana | |
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione | binding mode | Arabidopsis thaliana | |
benzobicyclone | - |
Arabidopsis thaliana | |
bicyclopyrone | - |
Arabidopsis thaliana | |
mesotrione | - |
Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
sulcotrione | - |
Arabidopsis thaliana | |
tefuryltrione | - |
Arabidopsis thaliana | |
tembotrione | - |
Arabidopsis thaliana |
Metals/Ions | Comment | Organism | Structure |
---|---|---|---|
Fe2+ | required | Arabidopsis thaliana |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
4-hydroxyphenylpyruvate + O2 | Arabidopsis thaliana | - |
homogentisate + CO2 | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Arabidopsis thaliana | P93836 | - |
- |
Purification (Comment) | Organism |
---|---|
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration | Arabidopsis thaliana |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
4-hydroxyphenylpyruvate + O2 | - |
Arabidopsis thaliana | homogentisate + CO2 | - |
? |
Synonyms | Comment | Organism |
---|---|---|
HPPD | - |
Arabidopsis thaliana |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
30 | - |
assay at | Arabidopsis thaliana |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
7 | - |
assay at | Arabidopsis thaliana |
Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|
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 | Arabidopsis thaliana | |
0.000013 | - |
mesotrione | pH 7.0, 30°C, recombinant His-tagged enzyme | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana | |
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 | Arabidopsis thaliana |
General Information | Comment | Organism |
---|---|---|
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 | Arabidopsis thaliana |