EC Number | Application | Comment | Organism |
---|---|---|---|
4.1.3.36 | drug development | the enzyme is a target for development of antibacterial agents | Mycobacterium tuberculosis |
EC Number | Inhibitors | Comment | Organism | Structure |
---|---|---|---|---|
4.1.3.36 | 2-CoA-4-(2,4-dichlorophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(2-bromophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(2-chlorophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(2-fluorophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(2-iodophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(2-methoxyphenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(2-nitrophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(3-chlorophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(4-dichlorophenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 2-CoA-4-(4-methoxyphenyl)-4-oxobutanoic acid | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 3-(2,4-dichlorophenyl)-3-oxopropyl-CoA | weak inhibition | Mycobacterium tuberculosis | |
4.1.3.36 | 4-(2,4-dichlorophenyl)-4-oxobutanoyl-CoA | - |
Mycobacterium tuberculosis | |
4.1.3.36 | 4-(2-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | half-life at 25°C, pH 7.4, is 0.4 h | Mycobacterium tuberculosis | |
4.1.3.36 | 4-(2-methoxyphenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | half-life at 25°C, pH 7.4, is 11.6 h | Mycobacterium tuberculosis | |
4.1.3.36 | 4-(4-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | half-life at 25°C, pH 7.4, is 6.8 h | Mycobacterium tuberculosis | |
4.1.3.36 | 4-(4-fluorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | half-life at 25°C, pH 7.4, is 12.2 h | Mycobacterium tuberculosis | |
4.1.3.36 | 4-oxo-2-[[(1S)-1-phenylethyl]amino]-4-[2-(trifluoromethyl)phenyl]butanoic acid | half-life at 25°C, pH 7.4, is 0.2 h | Mycobacterium tuberculosis | |
4.1.3.36 | 4-oxo-4-chlorophenylbutenoyl methyl ester | penetrates the cell where it is hydrolyzed and reacts with CoA to generate the active antibacterial compound, mechanism, overview | Mycobacterium tuberculosis | |
4.1.3.36 | 4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid | half-life at 25°C, pH 7.4, is 11.6 h | Mycobacterium tuberculosis | |
4.1.3.36 | additional information | 2-amino-4-oxo-4-phenylbutanoate inhibitors are unstable in solution and eliminate to form the corresponding 4-oxo-4-phenylbut-2-enoates that then react with CoA in situ to form nanomolar inhibitors of MenB. The potency of these compounds results from interaction of the CoA adduct carboxylate with the MenB oxyanion hole, a conserved structural motif in the crotonase superfamily. No inhibition by 1548L21 at 0.3 mM | Mycobacterium tuberculosis |
EC Number | Organism | UniProt | Comment | Textmining |
---|---|---|---|---|
4.1.3.36 | Mycobacterium tuberculosis | P9WNP5 | - |
- |
4.1.3.36 | Mycobacterium tuberculosis H37Rv | P9WNP5 | - |
- |
EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|---|
4.1.3.36 | o-succinylbenzoate + CoA | catalyzes an intramolecular Claisen condensation reaction leading to the formation of 1,4-dihydroxy-2-naphthoyl-CoA from o-succinylbenzoate, the enzyme substrate is chemically unstable | Mycobacterium tuberculosis | 1,4-dihydroxy-2-naphthoyl-CoA + H2O | - |
? | |
4.1.3.36 | o-succinylbenzoate + CoA | catalyzes an intramolecular Claisen condensation reaction leading to the formation of 1,4-dihydroxy-2-naphthoyl-CoA from o-succinylbenzoate, the enzyme substrate is chemically unstable | Mycobacterium tuberculosis H37Rv | 1,4-dihydroxy-2-naphthoyl-CoA + H2O | - |
? |
EC Number | Synonyms | Comment | Organism |
---|---|---|---|
4.1.3.36 | DHNA-CoA synthase | - |
Mycobacterium tuberculosis |
4.1.3.36 | MenB | - |
Mycobacterium tuberculosis |
EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|---|
4.1.3.36 | 25 | - |
assay at | Mycobacterium tuberculosis |
EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|---|
4.1.3.36 | 7.4 | - |
assay at | Mycobacterium tuberculosis |
EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|---|
4.1.3.36 | 0.000049 | - |
2-CoA-4-(2,4-dichlorophenyl)-4-oxobutanoic acid | pH 7.4, 25°C | Mycobacterium tuberculosis | |
4.1.3.36 | 0.000097 | - |
2-CoA-4-(2-chlorophenyl)-4-oxobutanoic acid | pH 7.4, 25°C | Mycobacterium tuberculosis | |
4.1.3.36 | 0.00035 | - |
2-CoA-4-(4-dichlorophenyl)-4-oxobutanoic acid | pH 7.4, 25°C | Mycobacterium tuberculosis |
EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|---|
4.1.3.36 | 0.000103 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2-chlorophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.000106 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2,4-dichlorophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.000135 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2-bromophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.000154 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2-nitrophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.000204 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2-fluorophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.000421 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2-iodophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.00047 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(4-dichlorophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.0022 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-(2,4-dichlorophenyl)-4-oxobutanoyl-CoA | |
4.1.3.36 | 0.0032 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-oxo-2-[[(1S)-1-phenylethyl]amino]-4-[2-(trifluoromethyl)phenyl]butanoic acid | |
4.1.3.36 | 0.0084 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-(2-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | |
4.1.3.36 | 0.0121 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(2-methoxyphenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.0141 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(3-chlorophenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.0144 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-(4-fluorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | |
4.1.3.36 | 0.0335 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 2-CoA-4-(4-methoxyphenyl)-4-oxobutanoic acid | |
4.1.3.36 | 0.0527 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid | |
4.1.3.36 | 0.12 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-(2-methoxyphenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid | |
4.1.3.36 | 0.4 | - |
above, pH 7.4, 25°C | Mycobacterium tuberculosis | 3-(2,4-dichlorophenyl)-3-oxopropyl-CoA | |
4.1.3.36 | 117 | - |
pH 7.4, 25°C | Mycobacterium tuberculosis | 4-(4-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid |