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Literature summary for 1.13.11.27 extracted from
- Synthesis and herbicidal activity of triketone-quinoline hybrids as novel 4-hydroxyphenylpyruvate dioxygenase inhibitors (2015), J. Agric. Food Chem., 63, 5587-5596 .
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-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one | - |
Arabidopsis thaliana |  |
| 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile | - |
Arabidopsis thaliana | |
| 3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| 3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one | - |
Arabidopsis thaliana | |
| mesotrione | - |
Arabidopsis thaliana | |
| 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)
| 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 |
|---|---|---|---|---|---|
| 0.000007 | - |
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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 0.000013 | - |
mesotrione | pH 7.0, 30°C, recombinant His-tagged enzyme | Arabidopsis thaliana | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 0.000075 | - |
3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one | recombinant His-tagged enzyme, pH 7.0, 30°C | Arabidopsis thaliana | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
| 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 | |
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