BRENDA - Enzyme Database show
show all sequences of 2.4.99.B6

Discovery of new Gram-negative antivirulence drugs: structure and properties of novel E. coli WaaC inhibitors

Moreau, F.; Desroy, N.; Genevard, J.M.; Vongsouthi, V.; Gerusz, V.; Le Fralliec, G.; Oliveira, C.; Floquet, S.; Denis, A.; Escaich, S.; Wolf, K.; Busemann, M.; Aschenbrenner, A.; Bioorg. Med. Chem. Lett. 18, 4022-4026 (2008)

Data extracted from this reference:

Application
Application
Commentary
Organism
medicine
the enzyme represent a promising and attractive target for the discovery of new Gram-negative antibacterial drugs based on antivirulence mechanisms
Escherichia coli
Inhibitors
Inhibitors
Commentary
Organism
Structure
2-aryl-5-methyl-4-(5-aryl-furan-2-yl-methylene)-2,4-dihydro-pyrazol-3-one
micromolar inhibitors are identified by virtual screening, promising lead series for further optimization as antivirulence drug
Escherichia coli
3-[(4Z)-4-([5-[3-(methoxycarbonyl)phenyl]furan-2-yl]methylidene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
3-[(4Z)-4-[[5-(3-acetylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
3-[(4Z)-4-[[5-(3-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
3-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
4-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-methylbenzoic acid
-
Escherichia coli
4-[(4Z)-3-methyl-5-oxo-4-[(5-phenylfuran-2-yl)methylidene]-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
4-[(4Z)-4-[[5-(3-carbamoylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
4-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
5-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
-
Escherichia coli
5-(5-[(Z)-[1-(4-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
-
Escherichia coli
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Escherichia coli
P24173
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ADP-L-glycero-beta-D-manno-heptose + lipopolysaccahride from Salmonella minnesota R595
-
727135
Escherichia coli
ADP + ?
-
-
-
?
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.001
-
5-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.002
-
3-[(4Z)-4-[[5-(3-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.003
-
3-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.0031
-
5-(5-[(Z)-[1-(4-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.015
-
3-[(4Z)-4-[[5-(3-acetylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.018
-
4-[(4Z)-4-[[5-(3-carbamoylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.031
-
4-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-methylbenzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.049
-
3-[(4Z)-4-([5-[3-(methoxycarbonyl)phenyl]furan-2-yl]methylidene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.051
-
4-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.055
-
4-[(4Z)-3-methyl-5-oxo-4-[(5-phenylfuran-2-yl)methylidene]-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
Application (protein specific)
Application
Commentary
Organism
medicine
the enzyme represent a promising and attractive target for the discovery of new Gram-negative antibacterial drugs based on antivirulence mechanisms
Escherichia coli
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2-aryl-5-methyl-4-(5-aryl-furan-2-yl-methylene)-2,4-dihydro-pyrazol-3-one
micromolar inhibitors are identified by virtual screening, promising lead series for further optimization as antivirulence drug
Escherichia coli
3-[(4Z)-4-([5-[3-(methoxycarbonyl)phenyl]furan-2-yl]methylidene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
3-[(4Z)-4-[[5-(3-acetylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
3-[(4Z)-4-[[5-(3-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
3-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
4-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-methylbenzoic acid
-
Escherichia coli
4-[(4Z)-3-methyl-5-oxo-4-[(5-phenylfuran-2-yl)methylidene]-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
4-[(4Z)-4-[[5-(3-carbamoylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
4-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
-
Escherichia coli
5-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
-
Escherichia coli
5-(5-[(Z)-[1-(4-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
-
Escherichia coli
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.001
-
5-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.002
-
3-[(4Z)-4-[[5-(3-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.003
-
3-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.0031
-
5-(5-[(Z)-[1-(4-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-chlorobenzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.015
-
3-[(4Z)-4-[[5-(3-acetylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.018
-
4-[(4Z)-4-[[5-(3-carbamoylphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.031
-
4-(5-[(Z)-[1-(3-carboxyphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene]methyl]furan-2-yl)-2-methylbenzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.049
-
3-[(4Z)-4-([5-[3-(methoxycarbonyl)phenyl]furan-2-yl]methylidene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.051
-
4-[(4Z)-4-[[5-(4-carboxyphenyl)furan-2-yl]methylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
0.055
-
4-[(4Z)-3-methyl-5-oxo-4-[(5-phenylfuran-2-yl)methylidene]-4,5-dihydro-1H-pyrazol-1-yl]benzoic acid
pH and temperature not specified in the publication
Escherichia coli
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ADP-L-glycero-beta-D-manno-heptose + lipopolysaccahride from Salmonella minnesota R595
-
727135
Escherichia coli
ADP + ?
-
-
-
?
Other publictions for EC 2.4.99.B6
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
737682
Czyzyk
Escherichia coli heptosyltrans ...
Escherichia coli
Biochemistry
52
5158-5160
2013
-
-
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726955
Czyzyk
Lipopolysaccharide biosynthesi ...
Escherichia coli
Biochemistry
50
10570-10572
2011
-
-
-
-
-
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-
8
-
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-
1
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2
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6
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8
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8
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1
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6
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8
-
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1
1
-
8
8
727326
Durka
The inhibition of liposacchari ...
Escherichia coli
Chemistry
18
641-651
2011
-
-
-
-
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1
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1
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-
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1
1
-
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-
727135
Moreau
Discovery of new Gram-negative ...
Escherichia coli
Bioorg. Med. Chem. Lett.
18
4022-4026
2008
-
1
-
-
-
-
11
-
-
-
-
-
-
1
-
-
-
-
-
-
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1
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10
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1
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11
10
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1
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728139
Grizot
Structure of the Escherichia c ...
Escherichia coli
J. Mol. Biol.
363
383-394
2006
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1
-
1
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1
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1
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1
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1
1
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1
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1
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1
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1
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1
1
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1
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1
1
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1
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1
1
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728049
Gronow
Characterization of the physio ...
Escherichia coli
J. Endotoxin Res.
7
263-270
2001
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1
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3
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2
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727413
Gronow
Comparative functional charact ...
Escherichia coli
Eur. J. Biochem.
267
6602-6611
2000
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-
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3
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2
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1
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1
1
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2
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1
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1
1
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727824
Kadrmas
Enzymatic synthesis of lipopol ...
Escherichia coli
J. Biol. Chem.
273
2799-2807
1998
1
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1
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1
2
1
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2
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1
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1
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3
1
1
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1
1
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1
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1
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1
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1
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1
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