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Literature summary for 1.3.5.2 extracted from
- Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes synthesis, cytotoxicity, lipophilicity and molecular docking studies (2020), Bioorg. Chem., 105, 104373 .
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 2-(2,3-bis(benzyloxy)phenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(2,4-bis(benzyloxy)phenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(2,4-dimethoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3,4-bis(benzyloxy)phenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3,4-dibutoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3,4-dihydroxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3,4-diisobutoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3,4-dimethoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3,4-dipropoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(3-methoxy-4-propoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(4-(benzyloxy)-3-methoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(4-butoxy-3-methoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(4-hydroxy-3-methoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 2-(4-isobutoxy-3-methoxyphenyl)quinoline-4-carboxylic acid | - |
Homo sapiens | |
| 6-fluoro-2-[2-methyl-4-phenoxy-5-(propan-2-yl)phenyl]quinoline-4-carboxylic acid | i.e. C44 | Homo sapiens | |
| brequinar | - |
Homo sapiens |  |
| leflunomide | - |
Homo sapiens | |
| additional information | synthesis of a series of 2-substituted quinoline-4-carboxylic acids by Doebner reaction starting from freely available protocatechuic aldehyde and vanillin precursors. Human dihydroorotate dehydrogenase (hDHODH) is recognised as a clear molecular target for these heterocycles. All compounds are also tested for their antiproliferative potential against three cancer cells (MCF-7, A549, A375) and one normal cell line (HaCaT) to evaluate the selective cytotoxicity, overview. IC50 for cytotoxicity in in vivo assays. Molecular docking studies | Homo sapiens | |
| teriflunomide | - |
Homo sapiens | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (S)-dihydroorotate + decylubiquinone | Homo sapiens | - |
orotate + decylubiquinol | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | Q02127 | - |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (S)-dihydroorotate + decylubiquinone | - |
Homo sapiens | orotate + decylubiquinol | - |
? | |
| additional information | reduction of decylubiquinone (DUQ) is stoichiometrically equivalent to reduction of 2,6-ichloroindophenol (DCIP) resulting in the decrease in absorbance at 610 nm, which is measured | Homo sapiens | ? | - |
- |
|
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| dihydroorotate dehydrogenase | - |
Homo sapiens |
| hDHODH | - |
Homo sapiens |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 22 | - |
assay at room temperature | Homo sapiens |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 8 | - |
assay at | Homo sapiens |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| decylubiquinone | - |
Homo sapiens | |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.00001 | - |
pH 8.0, 22°C | Homo sapiens | brequinar | |
| 0.0009 | - |
pH 8.0, 22°C | Homo sapiens | leflunomide | |
| 0.148 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3,4-diisobutoxyphenyl)quinoline-4-carboxylic acid | |
| 0.153 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3,4-dibutoxyphenyl)quinoline-4-carboxylic acid | |
| 0.268 | - |
pH 8.0, 22°C | Homo sapiens | 2-(2,3-bis(benzyloxy)phenyl)quinoline-4-carboxylic acid | |
| 0.27 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3,4-bis(benzyloxy)phenyl)quinoline-4-carboxylic acid | |
| 0.34 | - |
pH 8.0, 22°C | Homo sapiens | 2-(2,4-bis(benzyloxy)phenyl)quinoline-4-carboxylic acid | |
| 0.34 | - |
pH 8.0, 22°C | Homo sapiens | 2-(4-butoxy-3-methoxyphenyl)quinoline-4-carboxylic acid | |
| 0.384 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3,4-dipropoxyphenyl)quinoline-4-carboxylic acid | |
| 0.438 | - |
pH 8.0, 22°C | Homo sapiens | 2-(4-isobutoxy-3-methoxyphenyl)quinoline-4-carboxylic acid | |
| 0.449 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3-methoxy-4-propoxyphenyl)quinoline-4-carboxylic acid | |
| 0.467 | - |
pH 8.0, 22°C | Homo sapiens | 2-(4-(benzyloxy)-3-methoxyphenyl)quinoline-4-carboxylic acid | |
| 0.944 | - |
pH 8.0, 22°C | Homo sapiens | 2-(4-hydroxy-3-methoxyphenyl)quinoline-4-carboxylic acid | |
| 1.073 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3,4-dihydroxyphenyl)quinoline-4-carboxylic acid | |
| 1.387 | - |
pH 8.0, 22°C | Homo sapiens | 2-(3,4-dimethoxyphenyl)quinoline-4-carboxylic acid | |
| 2.549 | - |
pH 8.0, 22°C | Homo sapiens | 2-(2,4-dimethoxyphenyl)quinoline-4-carboxylic acid |
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