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Literature summary for 1.13.11.27 extracted from

  • Wang, D.W.; Lin, H.Y.; He, B.; Wu, F.X.; Chen, T.; Chen, Q.; Yang, W.C.; Yang, G.F.
    An efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors (2016), J. Agric. Food Chem., 64, 8986-8993 .
    View publication on PubMed
Search for more literature for 1.13.11.27

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
2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile
-
 Arabidopsis thaliana
2-[(2,3-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2,6-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(2-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(3,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(3,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(3-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(3-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(4-methoxyphenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(4-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[(pentafluorophenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-5,5-dimethyl-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-5-methyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
3-hydroxy-5-methyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
 Arabidopsis thaliana
6-[2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
 Arabidopsis thaliana
6-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
 Arabidopsis thaliana
7-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]-2H-1-benzopyran-2-one
-
 Arabidopsis thaliana
mesotrione
-
 Arabidopsis thaliana
additional information efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview 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
AtHPPD
-
 Arabidopsis thaliana
HPD
-
 Arabidopsis thaliana
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
0.000013
-
 mesotrione pH 7.0, 30°C, recombinant His-tagged enzyme Arabidopsis thaliana
0.000029
-
 2-[(4-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000031
-
 2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000034
-
 2-[(2-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
0.000043
-
 2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000045
-
 3-hydroxy-2-[(2-nitrophenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000045
-
 2-[(2,6-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000055
-
 3-hydroxy-2-[(pentafluorophenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000066
-
 2-[(2,4-dibromophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000069
-
 3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000075
-
 2-[(3-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000077
-
 3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000078
-
 2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
0.000113
-
 2-[(2,3-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000121
-
 2-[(2,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000134
-
 3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000184
-
 3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000189
-
 2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000197
-
 2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000208
-
 2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000215
-
 3-hydroxy-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
0.000253
-
 3-hydroxy-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000267
-
 2-[(3,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000301
-
 3-hydroxy-2-[(4-methoxyphenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000351
-
 2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000354
-
 3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000369
-
 2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000544
-
 3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000547
-
 2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000561
-
 3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000598
-
 3-hydroxy-2-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000623
-
 3-hydroxy-2-[(3-methylphenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
0.000894
-
 3-hydroxy-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000956
-
 2-[(3,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.000988
-
 3-hydroxy-2-[(4-methylphenoxy)acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.001052
-
 3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
0.001143
-
 2-[(2-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
0.001243
-
 3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
0.002141
-
 2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
0.002831
-
 2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
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 Arabidopsis thaliana
0.005571
-
 3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one recombinant His-tagged enzyme, pH 7.0, 30°C Arabidopsis thaliana