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Literature summary for 1.14.13.8 extracted from
- Oxidative activation of thiacetazone by the Mycobacterium tuberculosis flavin monooxygenase EtaA and human FMO1 and FMO3 (2006), Chem. Res. Toxicol., 19, 443-449.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| expression of His-tagged EtaA in Escherichia coli strain DH5alpha | Mycobacterium tuberculosis |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| additional information | - |
additional information | steady-state kinetics | Mycobacterium tuberculosis | |
| 0.131 | - |
thiacetazone | recombinant EtaA, pH 9.0, 37°C, thiacetazone sulfinic acid formation | Mycobacterium tuberculosis |  |
| 0.147 | - |
thiacetazone | recombinant EtaA, pH 9.0, 37°C, thiacetazone carbodiimide formation | Mycobacterium tuberculosis | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| ethionamide + NADPH + O2 + H+ | Mycobacterium tuberculosis | bioactivation by EtaA | 2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O | - |
? | |
| ethionamide + NADPH + O2 + H+ | Homo sapiens | bioactivation by isozymes FMO1 and FMO3 | 2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 H+ + 2 O2 | Mycobacterium tuberculosis | bioactivation by EtaA | thiacetazone carbodiimide + 2 NADP+ + 2 H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 H+ + 2 O2 | Homo sapiens | bioactivation by isozymes FMO1 and FMO3, two-step process | thiacetazone carbodiimide + 2 NADP+ + 2 H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 O2 | Mycobacterium tuberculosis | bioactivation by EtaA | (E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | - |
isozymes FMO1 and FMO3 | - |
| Mycobacterium tuberculosis | - |
gene etaA or RV3854c | - |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant His-tagged EtaA from Escherichia coli strain DH5alpha by nickel affinity chromatography | Mycobacterium tuberculosis |
Specific Activity [micromol/min/mg]
| Specific Activity Minimum [µmol/min/mg] | Specific Activity Maximum [µmol/min/mg] | Comment | Organism |
|---|---|---|---|
| additional information | - |
- |
Homo sapiens |
| additional information | - |
- |
Mycobacterium tuberculosis |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| ethionamide + NADPH + O2 + H+ | bioactivation by EtaA | Mycobacterium tuberculosis | 2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O | - |
? | |
| ethionamide + NADPH + O2 + H+ | bioactivation by isozymes FMO1 and FMO3 | Homo sapiens | 2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O | - |
? | |
| ethionamide + NADPH + O2 + H+ | a thioamide-containing second line antitubercular prodrug | Homo sapiens | 2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O | - |
? | |
| ethionamide + NADPH + O2 + H+ | a thioamide-containing second line antitubercular prodrug | Mycobacterium tuberculosis | 2-ethyl-N-hydroxypyridine-4-carbothioamide + NADP+ + H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 H+ + 2 O2 | bioactivation by EtaA | Mycobacterium tuberculosis | thiacetazone carbodiimide + 2 NADP+ + 2 H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 H+ + 2 O2 | bioactivation by isozymes FMO1 and FMO3, two-step process | Homo sapiens | thiacetazone carbodiimide + 2 NADP+ + 2 H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 H+ + 2 O2 | a thiourea-containing second line antitubercular prodrug | Homo sapiens | thiacetazone carbodiimide + 2 NADP+ + 2 H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 H+ + 2 O2 | a thiourea-containing second line antitubercular prodrug | Mycobacterium tuberculosis | thiacetazone carbodiimide + 2 NADP+ + 2 H2O | - |
? | |
| thiacetazone + 2 NADPH + 2 O2 | bioactivation by EtaA | Mycobacterium tuberculosis | (E)-{(2E)-[4-(acetylamino)benzylidene]hydrazinylidene}(amino)methanesulfinic acid + 2 NADP+ + H2O | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| EtaA | - |
Mycobacterium tuberculosis |
| FMO | - |
Homo sapiens |
| FMO | - |
Mycobacterium tuberculosis |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | - |
assay at | Homo sapiens |
| 37 | - |
assay at | Mycobacterium tuberculosis |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.048 | - |
thiacetazone | recombinant EtaA, pH 9.0, 37°C, thiacetazone carbodiimide formation | Mycobacterium tuberculosis | |
| 0.085 | - |
thiacetazone | recombinant EtaA, pH 9.0, 37°C, thiacetazone sulfinic acid formation | Mycobacterium tuberculosis | |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 9 | - |
- |
Homo sapiens |
| 9 | - |
- |
Mycobacterium tuberculosis |
pH Range
| pH Minimum | pH Maximum | Comment | Organism |
|---|---|---|---|
| 6.5 | 10 | pH profile | Mycobacterium tuberculosis |
| 6.5 | 10 | isozyme FMO1, pH profile | Homo sapiens |
| 7.5 | 10 | isozyme FMO3, pH profile | Homo sapiens |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| FAD | - |
Homo sapiens | |
| FAD | - |
Mycobacterium tuberculosis | |
| NADPH | - |
Homo sapiens | |
| NADPH | - |
Mycobacterium tuberculosis | |
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