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Literature summary for 2.5.1.7 extracted from

  • Miller, K.; Dunsmore, C.J.; Leeds, J.A.; Patching, S.G.; Sachdeva, M.; Blake, K.L.; Stubbings, W.J.; Simmons, K.J.; Henderson, P.J.; De Los Angeles, J.; Fishwick, C.W.; Chopra, I.
    Benzothioxalone derivatives as novel inhibitors of UDP-N-acetylglucosamine enolpyruvyl transferases (MurA and MurZ) (2010), J. Antimicrob. Chemother., 65, 2566-2573.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
-
Staphylococcus aureus
-
Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
Staphylococcus aureus
2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
-
Staphylococcus aureus
2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
-
Staphylococcus aureus
2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
-
Staphylococcus aureus
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
Staphylococcus aureus
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
Staphylococcus aureus
2-oxo-1,3-benzoxathiol-6-yl sulfamate
-
Escherichia coli
2-oxo-1,3-benzoxathiol-6-yl sulfamate
-
Staphylococcus aureus
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
Escherichia coli
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
Staphylococcus aureus
5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
-
Escherichia coli
5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
-
Staphylococcus aureus
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
Escherichia coli
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
Staphylococcus aureus
5-hydroxy-7-(3-methylphenyl)-1,3-benzoxathiol-2-one
-
Escherichia coli
5-hydroxy-7-(3-methylphenyl)-1,3-benzoxathiol-2-one slight inhibition at 0.12 mM Staphylococcus aureus
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
Escherichia coli
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one slight inhibition at 0.12 mM Staphylococcus aureus
5-hydroxybenzo[d][1,3]oxathiol-2-one
-
Escherichia coli
5-hydroxybenzo[d][1,3]oxathiol-2-one
-
Staphylococcus aureus
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
Escherichia coli
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
Staphylococcus aureus
5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
-
Escherichia coli
5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
-
Staphylococcus aureus
5-methoxy-1,3-benzoxathiole
-
Escherichia coli
5-methoxy-1,3-benzoxathiole slight inhibition at 0.12 mM Staphylococcus aureus
5-methoxybenzo[d][1,3]oxathiol-2-one
-
Escherichia coli
5-methoxybenzo[d][1,3]oxathiol-2-one
-
Staphylococcus aureus
7-(4-fluorophenyl)-5-hydroxy-1,3-benzoxathiol-2-one
-
Escherichia coli
7-(4-fluorophenyl)-5-hydroxy-1,3-benzoxathiol-2-one slight inhibition at 0.12 mM Staphylococcus aureus
fosfomycin
-
Escherichia coli
fosfomycin
-
Staphylococcus aureus

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Escherichia coli JM109
-
-
-
Staphylococcus aureus
-
-
-
Staphylococcus aureus SH1000
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine
-
Staphylococcus aureus UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + phosphate
-
r
phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine
-
Escherichia coli UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + phosphate
-
r
phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine
-
Escherichia coli JM109 UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + phosphate
-
r
phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine
-
Staphylococcus aureus SH1000 UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + phosphate
-
r

Synonyms

Synonyms Comment Organism
MurA
-
Staphylococcus aureus
MurA
-
Escherichia coli
UDP-N-acetylglucosamine enolpyruvyl transferase
-
Staphylococcus aureus
UDP-N-acetylglucosamine enolpyruvyl transferase
-
Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00025
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-6-yl sulfamate
0.00028
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
0.00046
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
0.00046
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
0.00053
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-hydroxybenzo[d][1,3]oxathiol-2-one
0.00058
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
0.00058
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
0.0006
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli fosfomycin
0.00076
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
0.00095
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
0.00109
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
0.00113
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
0.00125
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus fosfomycin
0.00155
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
0.00196
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
0.00239
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-6-yl sulfamate
0.00243
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-6-yl sulfamate
0.00286
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
0.00286
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
0.0031
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
0.00349
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
0.00515
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
0.00645
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-methoxybenzo[d][1,3]oxathiol-2-one
0.00668
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
0.00727
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-hydroxy-7-(3-methylphenyl)-1,3-benzoxathiol-2-one
0.00801
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
0.00801
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
0.00951
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
0.01079
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
0.01428
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 5-methoxy-1,3-benzoxathiole
0.01794
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 2-oxo-1,3-benzoxathiol-6-yl sulfamate
0.01854
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Escherichia coli 7-(4-fluorophenyl)-5-hydroxy-1,3-benzoxathiol-2-one
0.02431
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
0.02479
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 5-methoxybenzo[d][1,3]oxathiol-2-one
0.02609
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
0.02707
-
in 50 mM Tris-HCl, pH 7.9, at 37°C Staphylococcus aureus 5-hydroxybenzo[d][1,3]oxathiol-2-one