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Literature summary extracted from

  • Wang, D.W.; Lin, H.Y.; Cao, R.J.; Chen, T.; Wu, F.X.; Hao, G.F.; Chen, Q.; Yang, W.C.; Yang, G.F.
    Synthesis and herbicidal activity of triketone-quinoline hybrids as novel 4-hydroxyphenylpyruvate dioxygenase inhibitors (2015), J. Agric. Food Chem., 63, 5587-5596 .
    View publication on PubMed

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 2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
 Arabidopsis thaliana
1.13.11.27 3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
1.13.11.27 mesotrione
-
 Arabidopsis thaliana
1.13.11.27 additional information design, synthesis, and herbicidal activity of triketone-quinoline hybrids as 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview. Computational modeling and CoMSIA analysis 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 AtHPPD
-
 Arabidopsis thaliana
1.13.11.27 HPD
-
 Arabidopsis thaliana
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 0.000007
-
 3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000007
-
 3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000011
-
 2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000013
-
 mesotrione pH 7.0, 30°C, recombinant His-tagged enzyme Arabidopsis thaliana
1.13.11.27 0.000014
-
 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000025
-
 2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000029
-
 2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000062
-
 3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 0.000072
-
 2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000075
-
 3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 0.000076
-
 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 0.000213
-
 2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana
1.13.11.27 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 Arabidopsis thaliana