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(E)-3-fluorophosphoenolpyruvate
(hydroxymethyl)phosphonic acid
i.e. CID-21680357
(S)-2-[2-(naphthalene-1-sulfonylamino)-5-(naphthalene-1-sulfonyloxy)-benzoylamino]-pentanedioic acid
competitive with UDP-N-acetylglucosamine
(S)-2-[2-(naphthalene-1-sulfonylamino)-5-(naphthalene-1-sulfonyloxy)-benzoylamino]-succinic acid
-
(Z)-3-fluorophosphoenolpyruvate
2-(4-methylpiperazin-1-yl)-3,4-dihydronaphthalen-1(2H)-one
2-bromo-5-[(Z)-2-bromo-2-nitroethenyl]furan
-
-
2-chloro-3-(4-methoxyphenoxy)naphthalene-1,4-dione
-
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
2-oxo-1,3-benzoxathiol-6-yl sulfamate
2-[4-(2-hydroxyethyl)piperazin-1-yl]-3,4-dihydronaphthalen-1(2H)-one
2-[4-(2-hydroxyethyl)piperazin-1-yl]-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one
3-Bromopyruvate
-
irreversible, inhibitory effect is increased by UDP-GlcNAc
3-methylidenedihydrofuran-2(3H)-one
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
5,5'-dithiobis(2-nitrobenzoic acid)
-
complete inhibition at 0.01 M; i.e. DTNB
5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
5-hydroxy-1,3-benzoxathiol-2-one
5-hydroxy-7-(3-methylphenyl)-1,3-benzoxathiol-2-one
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
5-hydroxybenzo[d][1,3]oxathiol-2-one
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
5-methoxy-1,3-benzoxathiole
5-methoxybenzo[d][1,3]oxathiol-2-one
6,7-dimethoxy-2-[4-(2-phenylethyl)piperazin-1-yl]-3,4-dihydronaphthalen-1(2H)-one
6-chloro-7-(4-methoxyphenoxy)quinoline-5,8-dione
-
-
7-(4-fluorophenyl)-5-hydroxy-1,3-benzoxathiol-2-one
7-chloro-6-(4-hydroxyphenoxy)quinoline-5,8-dione
HESFWYLPHQSY
-
i.e. PEP 1354. the peptide seems to prevent the closure of the Pro114-123 loop and, consequently, the open-closed transition of the MurA structure
iodoacetamide
-
inhibition by alkylation of the active site Cys155, pH-dependent, no alkylation below pH 7.0, maximum alkylation at pH 9.0
methyl 1,4-dihydroxynaphthalene-2-carboxylate
-
-
orientin
mixed type inhibition
oxalic acid
i.e. AB-00005001
oxamic acid
i.e. ZINC04658565
p-chloromercuribenzoate
-
-
PEP 1354 peptide
-
competitive inhibitor
-
PGE-553828
-
competitive against UDP-GlcNAc; inhibition mechanism, kinetics
-
phosphoenol-2-ketovalerate
-
-
phosphoenolpyruvate
-
about 65% residual activity at 2.5 mM
quercetin-3-O-D-glucuronide
uncompetitive inhibition
Tartronic acid
i.e. ZINC901335
Trypsin
wild-type and mutant C115S, no protection via individually binding of substrates or inhibitor fosfomycin, but via binding of both, the 2 substrates and inhibitor fosfomycin
-
UDP-N-acetylmuramic acid-L-Ala
-
weak
UDP-N-acetylmuramic acid-L-Ala-D-Glu
UDP-N-acetylmuramyl-L-Ala-D-Glu-meso-alpha,epsilon-diaminopimelic acid
uridine diphospho-N-acetylmuramyl-L-Ala-D-gamma-Glu-meso-alpha,epsilon-diaminopimelic-acid-D-Ala-D-Ala
(+)-6-tuliposide B
-
35% residual activity at 0.1 mM
(+)-6-tuliposide B
-
25% residual activity at 0.1 mM
(+)-tulipalin B
-
3.3% residual activity at 0.1 mM
(+)-tulipalin B
-
2.5% residual activity at 0.1 mM
(-)-tulipalin B
-
3.7% residual activity at 0.1 mM
(-)-tulipalin B
-
2.8% residual activity at 0.1 mM
(E)-3-fluorophosphoenolpyruvate
-
pseudosubstrate, formation of a tetrahedral intermediate in the reaction pathway, investigation of chirality of the intermediate stereospecifically formed at the active site in D2O
(E)-3-fluorophosphoenolpyruvate
-
formation of 2 reaction intermediates: a covalent phosphofluorolactyl-enzyme adduct and a free phosphofluorolactyl-UDP-GlcNAc tetrahedral adduct; inactivation; kinetics
(Z)-3-fluorophosphoenolpyruvate
-
pseudosubstrate, formation of a tetrahedral intermediate in the reaction pathway, investigation of chirality of the intermediate stereospecifically formed at the active site in D2O
(Z)-3-fluorophosphoenolpyruvate
-
formation of 2 reaction intermediates: a covalent phosphofluorolactyl-enzyme adduct and a free phosphofluorolactyl-UDP-GlcNAc tetrahedral adduct; inactivation; kinetics
(Z)-3-fluorophosphoenolpyruvate
-
kinetics, mutant C115D; wild-type and mutant C115D, competitive against phosphoenolpyruvate
1-tuliposide A
potent inhibitor
1-tuliposide A
potent inhibitor
1-tuliposide A
potent inhibitor
1-tuliposide A
-
potent inhibitor
1-tuliposide A
-
potent inhibitor
1-tuliposide A
-
potent inhibitor
1-tuliposide B
potent inhibitor
1-tuliposide B
potent inhibitor
1-tuliposide B
potent inhibitor
1-tuliposide B
-
potent inhibitor
1-tuliposide B
-
potent inhibitor
1-tuliposide B
-
potent inhibitor
2-(4-methylpiperazin-1-yl)-3,4-dihydronaphthalen-1(2H)-one
-
2-(4-methylpiperazin-1-yl)-3,4-dihydronaphthalen-1(2H)-one
-
-
2-(4-methylpiperazin-1-yl)-3,4-dihydronaphthalen-1(2H)-one
-
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
-
2-oxo-1,3-benzoxathiol-5-yl (3-chlorophenyl)carbamate
-
-
2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
-
-
2-oxo-1,3-benzoxathiol-5-yl methylcarbamate
-
-
2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
-
-
2-oxo-1,3-benzoxathiol-5-yl pyridine-4-carboxylate
-
-
2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl 4-nitrobenzenesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl benzenesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl methanesulfonate
-
-
2-oxo-1,3-benzoxathiol-6-yl sulfamate
-
-
2-oxo-1,3-benzoxathiol-6-yl sulfamate
-
-
2-[4-(2-hydroxyethyl)piperazin-1-yl]-3,4-dihydronaphthalen-1(2H)-one
-
2-[4-(2-hydroxyethyl)piperazin-1-yl]-3,4-dihydronaphthalen-1(2H)-one
-
-
2-[4-(2-hydroxyethyl)piperazin-1-yl]-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one
-
2-[4-(2-hydroxyethyl)piperazin-1-yl]-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one
-
-
3-methylidenedihydrofuran-2(3H)-one
-
54% residual activity at 0.1 mM
3-methylidenedihydrofuran-2(3H)-one
-
87% residual activity at 0.1 mM
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
-
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
-
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
-
4,7-dichloro-5-hydroxy-1,3-benzoxathiol-2-one
-
-
5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
-
-
5,7-dibromo-6-hydroxy-1,3-benzoxathiol-2-one
-
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
-
5-(prop-2-en-1-yloxy)-1,3-benzoxathiol-2-one
-
-
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
-
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
-
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
-
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
-
-
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
-
-
5-bromo-2-oxo-1,3-benzoxathiol-6-yl phenyl carbonate
-
-
5-hydroxy-1,3-benzoxathiol-2-one
-
5-hydroxy-1,3-benzoxathiol-2-one
-
5-hydroxy-1,3-benzoxathiol-2-one
-
5-hydroxy-1,3-benzoxathiol-2-one
-
-
5-hydroxy-1,3-benzoxathiol-2-one
-
-
5-hydroxy-1,3-benzoxathiol-2-one
-
-
5-hydroxy-7-(3-methylphenyl)-1,3-benzoxathiol-2-one
-
-
5-hydroxy-7-(3-methylphenyl)-1,3-benzoxathiol-2-one
-
slight inhibition at 0.12 mM
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
-
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
-
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
-
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
slight inhibition at 0.12 mM
5-hydroxy-7-(4-methoxyphenyl)-1,3-benzoxathiol-2-one
-
-
5-hydroxybenzo[d][1,3]oxathiol-2-one
-
-
5-hydroxybenzo[d][1,3]oxathiol-2-one
-
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
-
5-hydroxynaphtho[1,2-d][1,3]oxathiol-2-one
-
-
5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
-
-
5-hydroxynaphtho[2,1-d][1,3]oxathiol-2-one
-
-
5-methoxy-1,3-benzoxathiole
-
-
5-methoxy-1,3-benzoxathiole
-
slight inhibition at 0.12 mM
5-methoxybenzo[d][1,3]oxathiol-2-one
-
-
5-methoxybenzo[d][1,3]oxathiol-2-one
-
-
6,7-dimethoxy-2-[4-(2-phenylethyl)piperazin-1-yl]-3,4-dihydronaphthalen-1(2H)-one
-
6,7-dimethoxy-2-[4-(2-phenylethyl)piperazin-1-yl]-3,4-dihydronaphthalen-1(2H)-one
-
-
7-(4-fluorophenyl)-5-hydroxy-1,3-benzoxathiol-2-one
-
-
7-(4-fluorophenyl)-5-hydroxy-1,3-benzoxathiol-2-one
-
slight inhibition at 0.12 mM
7-chloro-6-(4-hydroxyphenoxy)quinoline-5,8-dione
-
-
7-chloro-6-(4-hydroxyphenoxy)quinoline-5,8-dione
-
-
cnicin
sesquiterpene lactone. The enzyme catalyzes the formation of a covalent adduct between cnicin and substrate UDP-N-acetylglucosamine via an anti-Michael 1,3-addition of UDP-N-acetylglucosamine to an alpha,beta-unsaturated carbonyl function in cnicin thus forming a noncovalent suicide inhibitor
cnicine
-
Co2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
Cu2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
Cu2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
cynaropicrin
-
diarylmethane
-
ebselen
-
ebselen
inhibitor covalently modifies the cysteine residue near the active site-loop of MurA, modification changes the open conformation of MurA to a more closed configuration, when compound is incubated for 30 min with dithiothreitol, its inhibitory activity against Haemophilus influenzae MurA is completely eliminated
epi-(+)-6-tuliposide B
-
19% residual activity at 0.1 mM
epi-(+)-6-tuliposide B
-
17% residual activity at 0.1 mM
Fe2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
Fe2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
fosfomycin
-
50 mM, 3fold inhibition
fosfomycin
-
resistant to fosfomycin inhibition due to exchange of cysteine for aspartate in the active site
fosfomycin
-
irreversible, active site SH-group is involved
fosfomycin
-
alkylates Cys115
fosfomycin
-
binds covalently to Cys115
fosfomycin
irreversible, alkylation of C115
fosfomycin
-
selectively inhibited by fosfomycin, which forms a covalent bond to the sulfhydryl group of the catalytically relevant Cys115 residue
fosfomycin
irreversible inhibitor
fosfomycin
-
alkylates Cys115; competitive against phosphoenolpyruvate; inhibits the wild-type, mutant C155D is completely resistant; t1/2 for inactivation of the wild-type enzyme: 6 s
fosfomycin
-
binds covalently to Cys115
fosfomycin
-
binding study by isothermal titration calorimetry; binds covalently to Cys115
fosfomycin
-
selectively inhibited by fosfomycin, which forms a covalent bond to the sulfhydryl group of the catalytically relevant Cys115 residue
fosfomycin
enolpyruvyl UDP-GlcNAc synthase is an antimicrobial target that is inhibited by the antibiotic fosfomycin
fosfomycin
irreversible inhibitor
fosfomycin
-
irreversible inhibition
fosfomycin
acting competitively as an analogue of phosphoenolpyruvate
fosfomycin
-
more than 90% inhibition at 0.2 mM
fosfomycin
irreversible inhibitor
fosfomycin
-
irreversible inhibitor
fosfomycin
-
despite low level expression during normal growth, murZ expression is strongly induced up to 6fold following exposure to inhibitors of peptidoglycan biosynthesis, minimum inhibitory concentration is 4 mg/ml; the naturally occurring antibiotic, which is an analogue of phosphoenolpyruvate, irreversibly inhibits the majority of MurA enzymes, fosfomycin minimum inhibitory concentration is 8 mg/ml, peptidoglycan content is reduced by approximately 25% following inactivation of murA
fosfomycin
-
irreversible inhibitor
fosfomycin
-
irreversible inhibitor
fosfomycin
-
about 50% residual activity at 50 mM
HESFWYLPHHQSY
competitive inhibition
HESFWYLPHHQSY
competitive inhibition
HESFWYLPHHQSY
-
competitive inhibition
HESFWYLPHHQSY
competitive inhibition
HESFWYLPHHQSY
-
competitive inhibition
HESFWYLPHHQSY
-
competitive inhibition
HESFWYLPHHQSY
-
competitive inhibition
imidazole
-
MnCl2
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
MnCl2
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
N-ethylmaleimide
-
-
N-ethylmaleimide
-
complete inhibition at 0.2 M
phosphonomycin
-
i.e. L-cis-2-epoxypropylphosphonic acid; inhibitor binding site is distinct from active site; irreversible inactivation, requires the presence of UDP-GlcNAc
-
phosphonomycin
irreversible inactivation, requires the presence of UDP-GlcNAc
-
pyrazolopyrimidine
reversible inhibitor
pyrazolopyrimidine
reversible inhibitor
pyrazolopyrimidine
reversible inhibitor
pyrazolopyrimidine
-
reversible inhibitor
pyrazolopyrimidine
-
reversible inhibitor
pyrazolopyrimidine
-
reversible inhibitor
RWJ-110192
reversible inhibitor
RWJ-110192
reversible inhibitor
RWJ-110192
reversible inhibitor
RWJ-110192
-
reversible inhibitor
RWJ-110192
-
reversible inhibitor
RWJ-110192
-
reversible inhibitor
RWJ-140998
irreversible inhibitor
RWJ-140998
irreversible inhibitor
RWJ-140998
irreversible inhibitor
RWJ-140998
-
irreversible inhibitor
RWJ-140998
-
irreversible inhibitor
RWJ-140998
-
irreversible inhibitor
RWJ-3981
irreversible inhibitor
RWJ-3981
irreversible inhibitor
RWJ-3981
irreversible inhibitor
RWJ-3981
-
irreversible inhibitor
RWJ-3981
-
irreversible inhibitor
RWJ-3981
-
irreversible inhibitor
T6361
-
-
T6361
competitive inhibition
T6361
competitive inhibition
T6361
competitive inhibition
T6361
-
competitive inhibition
T6361
-
competitive inhibition
T6361
-
competitive inhibition
T6362
-
T6362
competitive inhibition
T6362
competitive inhibition
T6362
competitive inhibition
T6362
-
competitive inhibition
T6362
-
competitive inhibition
T6362
-
competitive inhibition
terreic acid
irreversible inhibitor
terreic acid
irreversible inhibitor
terreic acid
irreversible inhibitor
terreic acid
-
irreversible inhibitor
terreic acid
-
irreversible inhibitor
terreic acid
-
irreversible inhibitor
thimerosal
-
thimerosal
inhibitor covalently modifies the cysteine residue near the active site-loop of MurA, modification changes the open conformation of MurA to a more closed configuration, when compound is incubated for 30 min with dithiothreitol, its inhibitory activity against Haemophilus influenzae MurA is completely eliminated
thiram
-
thiram
inhibitor covalently modifies the cysteine residue near the active site-loop of MurA, modification changes the open conformation of MurA to a more closed configuration, when compound is incubated for 30 min with dithiothreitol, its inhibitory activity against Haemophilus influenzae MurA is completely eliminated
tulipaline A
-
tulipaline B
-
UDP-N-acetylmuramic acid
-
weak
UDP-N-acetylmuramic acid
-
competitive with phosphate
UDP-N-acetylmuramic acid
-
UDP-N-acetylmuramic acid
-
-
UDP-N-acetylmuramic acid-L-Ala-D-Glu
-
weak
UDP-N-acetylmuramic acid-L-Ala-D-Glu
-
no inhibition
UDP-N-acetylmuramyl-L-Ala-D-Glu-meso-alpha,epsilon-diaminopimelic acid
-
-
UDP-N-acetylmuramyl-L-Ala-D-Glu-meso-alpha,epsilon-diaminopimelic acid
-
inhibitor binding site is distinct from active site
UDP-N-acetylmuramyl-L-Ala-D-Glu-meso-alpha,epsilon-diaminopimelic acid
-
above 1 mM
uridine diphospho-N-acetylmuramyl-L-Ala-D-gamma-Glu-meso-alpha,epsilon-diaminopimelic-acid-D-Ala-D-Ala
-
-
uridine diphospho-N-acetylmuramyl-L-Ala-D-gamma-Glu-meso-alpha,epsilon-diaminopimelic-acid-D-Ala-D-Ala
-
inhibitor binding site is distinct from active site
uridine diphospho-N-acetylmuramyl-L-Ala-D-gamma-Glu-meso-alpha,epsilon-diaminopimelic-acid-D-Ala-D-Ala
-
above 1 mM
Zn2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
Zn2+
-
metal ions do not enhance the activity of enzymes, activity is inhibited by 10 mM
additional information
-
no inhibition by pyruvate and fluoropyruvate
-
additional information
inhibitors derived from 5-sulfonoxy-anthranilic acid obstruct the transition from the open and unliganded to the closed UDP-N-acetylglucosamine liganded form
-
additional information
-
no inhibition by UDP-galactose
-
additional information
insight into the catalytic mechanism and covalent inhibition by QM/MM MD simulations
-
additional information
inhibitors are identified through computational and in vitro approaches
-