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Literature summary 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

Application

EC Number Application Comment Organism
1.13.11.27 agriculture 4-hydroxyphenylpyruvate dioxygenase is one of the most promising target sites for herbicide discovery Arabidopsis thaliana
1.13.11.27 drug development 4-hydroxyphenylpyruvate dioxygenase is one of the most promising target sites for herbicide discovery Arabidopsis thaliana

Cloned(Commentary)

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.27 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
1.13.11.27 1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
 Arabidopsis thaliana
1.13.11.27 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione binding mode Arabidopsis thaliana
1.13.11.27 benzobicyclone
-
 Arabidopsis thaliana
1.13.11.27 bicyclopyrone
-
 Arabidopsis thaliana
1.13.11.27 mesotrione
-
 Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 sulcotrione
-
 Arabidopsis thaliana
1.13.11.27 tefuryltrione
-
 Arabidopsis thaliana
1.13.11.27 tembotrione
-
 Arabidopsis thaliana

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.13.11.27 Fe2+ required Arabidopsis thaliana

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.11.27 4-hydroxyphenylpyruvate + O2 Arabidopsis thaliana
-
 homogentisate + CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.27 Arabidopsis thaliana P93836
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.27 4-hydroxyphenylpyruvate + O2
-
 Arabidopsis thaliana homogentisate + CO2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.27 HPPD
-
 Arabidopsis thaliana

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.13.11.27 30
-
 assay at Arabidopsis thaliana

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.13.11.27 7
-
 assay at Arabidopsis thaliana

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.13.11.27 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
1.13.11.27 0.000013
-
 mesotrione pH 7.0, 30°C, recombinant His-tagged enzyme Arabidopsis thaliana
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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
1.13.11.27 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

EC Number General Information Comment Organism
1.13.11.27 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