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Literature summary for 1.13.11.27 extracted from

  • Wang, D.W.; Lin, H.Y.; Cao, R.J.; Ming, Z.Z.; Chen, T.; Hao, G.F.; Yang, W.C.; Yang, G.F.
    Design, synthesis and herbicidal activity of novel quinazoline-2,4-diones as 4-hydroxyphenylpyruvate dioxygenase inhibitors (2015), Pest Manag. Sci., 71, 1122-1132 .
    View publication on PubMed
Search for more literature for 1.13.11.27

Application

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(Commentary)

Cloned (Comment) Organism
gene HPD, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Arabidopsis thaliana

Inhibitors

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

Metals/Ions Comment Organism Structure
Fe2+ required Arabidopsis thaliana

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4-hydroxyphenylpyruvate + O2 Arabidopsis thaliana
-
 homogentisate + CO2
-
 ?

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana P93836
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration Arabidopsis thaliana

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-hydroxyphenylpyruvate + O2
-
 Arabidopsis thaliana homogentisate + CO2
-
 ?

Synonyms

Synonyms Comment Organism
HPPD
-
 Arabidopsis thaliana

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
 assay at Arabidopsis thaliana

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
 assay at Arabidopsis thaliana

Ki Value [mM]

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

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