Application | Comment | Organism |
---|---|---|
drug development | the enzyme is an attractive target for blocking menaquinone biosynthesis as an antibacterial strategy | Escherichia coli |
drug development | the enzyme is an attractive target for blocking menaquinone biosynthesis as an antibacterial strategy | Mycobacterium tuberculosis |
Inhibitors | Comment | Organism | Structure |
---|---|---|---|
5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | - |
Escherichia coli | |
5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | - |
Mycobacterium tuberculosis | |
5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | - |
Staphylococcus aureus | |
5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | - |
Escherichia coli | |
5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | - |
Mycobacterium tuberculosis | |
5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | - |
Staphylococcus aureus | |
5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine | - |
Escherichia coli | |
5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine | - |
Mycobacterium tuberculosis | |
5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine | - |
Staphylococcus aureus | |
5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine | - |
Escherichia coli | |
5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine | - |
Mycobacterium tuberculosis | |
5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine | - |
Staphylococcus aureus | |
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine | - |
Escherichia coli | |
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine | - |
Mycobacterium tuberculosis | |
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine | - |
Staphylococcus aureus | |
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine | - |
Escherichia coli | |
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine | - |
Mycobacterium tuberculosis | |
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine | - |
Staphylococcus aureus | |
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine | - |
Escherichia coli | |
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine | - |
Mycobacterium tuberculosis | |
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine | - |
Staphylococcus aureus | |
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine | - |
Escherichia coli | |
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine | - |
Mycobacterium tuberculosis | |
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine | - |
Staphylococcus aureus | |
5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine | - |
Escherichia coli | |
5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine | - |
Mycobacterium tuberculosis | |
5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine | - |
Staphylococcus aureus | |
5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine | hydrolytically unstable at the acyl sulfamate moiety | Escherichia coli | |
5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine | - |
Mycobacterium tuberculosis | |
5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine | hydrolytically unstable at the acyl sulfamate moiety | Staphylococcus aureus | |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | - |
Escherichia coli | |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | sulfonyladenosine analogue of the cognate reaction intermediate, o-succinylbenzoate-AMP, competitive inhibitor of mtMenE with respect to ATP and a noncompetitive inhibitor with respect to 2-succinylbenzoate | Mycobacterium tuberculosis | |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | sulfonyladenosine analogue of the cognate reaction intermediate, o-succinylbenzoate-AMP. Putative active site residues, Arg222 and Ser302, may interact with the 2-succinylbenzoate aromatic carboxylate and bind the 2-succinylbenzoate ketone oxygen, respectively, computational docking of 2-succinylbenzoate-AMP with the unliganded crystal structure of saMenE | Staphylococcus aureus | |
5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine | - |
Escherichia coli | |
5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine | - |
Mycobacterium tuberculosis | |
5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine | - |
Staphylococcus aureus | |
additional information | structure-function relationship of o-succinylbenzoate-AMP sulfonyladenosine analogue inhibitors, overview | Mycobacterium tuberculosis |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
ATP + 2-succinylbenzoate + CoA | Staphylococcus aureus | - |
AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | - |
? | |
ATP + 2-succinylbenzoate + CoA | Escherichia coli | - |
AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | - |
? | |
ATP + 2-succinylbenzoate + CoA | Mycobacterium tuberculosis | - |
AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Escherichia coli | - |
- |
- |
Mycobacterium tuberculosis | - |
- |
- |
Staphylococcus aureus | - |
- |
- |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | bi uni uni bi ping-pong kinetic mechanism | Staphylococcus aureus | |
ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | bi uni uni bi ping-pong kinetic mechanism | Escherichia coli | |
ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | bi uni uni bi ping-pong kinetic mechanism | Mycobacterium tuberculosis |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
ATP + 2-succinylbenzoate + CoA | - |
Staphylococcus aureus | AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | - |
? | |
ATP + 2-succinylbenzoate + CoA | - |
Escherichia coli | AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | - |
? | |
ATP + 2-succinylbenzoate + CoA | - |
Mycobacterium tuberculosis | AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA | - |
? |
Synonyms | Comment | Organism |
---|---|---|
MenE | - |
Staphylococcus aureus |
MenE | - |
Escherichia coli |
MenE | - |
Mycobacterium tuberculosis |
o-succinylbenzoate-CoA synthetase | - |
Staphylococcus aureus |
o-succinylbenzoate-CoA synthetase | - |
Escherichia coli |
o-succinylbenzoate-CoA synthetase | - |
Mycobacterium tuberculosis |
OSB-CoA synthetase | - |
Staphylococcus aureus |
OSB-CoA synthetase | - |
Escherichia coli |
OSB-CoA synthetase | - |
Mycobacterium tuberculosis |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
ATP | - |
Staphylococcus aureus | |
ATP | - |
Escherichia coli | |
ATP | - |
Mycobacterium tuberculosis |
Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
---|---|---|---|---|---|
0.0054 | - |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | versus ATP, pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
0.0112 | - |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | versus 2-succinylbenzoate, pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
0.022 | - |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | pH and temperature not specified in the publication | Staphylococcus aureus | |
0.128 | - |
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine | pH and temperature not specified in the publication | Escherichia coli |
IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
---|---|---|---|---|---|
0.00016 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | |
0.0002 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine | |
0.00024 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine | |
0.00033 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | |
0.00057 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | |
0.00063 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine | |
0.0057 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine | |
0.0142 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine | |
0.0235 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine | |
0.0246 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine | |
0.0316 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | |
0.0341 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine | |
0.038 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine | |
0.0457 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine | |
0.0544 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | |
0.085 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine | |
0.101 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine | |
0.106 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine | |
0.117 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Staphylococcus aureus | 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Escherichia coli | 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine | |
0.2 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine |
General Information | Comment | Organism |
---|---|---|
additional information | the basic residue, Arg222, may interact with the aromatic carboxylate of 2-succinylbenzoate | Staphylococcus aureus |
additional information | the basic residue, Arg222, may interact with the aromatic carboxylate of 2-succinylbenzoate | Escherichia coli |
additional information | the basic residue, Arg222, may interact with the aromatic carboxylate of 2-succinylbenzoate | Mycobacterium tuberculosis |
physiological function | the enzyme is essential in Escherichia coli and is involved in menaquinone biosynthesis | Escherichia coli |
physiological function | the enzyme is essential in Mycobacterium tuberculosis and is involved in menaquinone biosynthesis | Mycobacterium tuberculosis |
physiological function | the enzyme is important in Mycobacterium tuberculosis | Staphylococcus aureus |