Information on EC 3.5.1.108 - UDP-3-O-acyl-N-acetylglucosamine deacetylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.5.1.108
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RECOMMENDED NAME
GeneOntology No.
UDP-3-O-acyl-N-acetylglucosamine deacetylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O = UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
lipid IVA biosynthesis
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Lipopolysaccharide biosynthesis
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Metabolic pathways
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lipid A biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetylglucosamine amidohydrolase
A zinc protein. The enzyme catalyses a committed step in the biosynthesis of lipid A.
CAS REGISTRY NUMBER
COMMENTARY hide
157971-99-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
different isolates, gene lpxC
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Manually annotated by BRENDA team
D22
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Manually annotated by BRENDA team
R477
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Manually annotated by BRENDA team
gene lpxC
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-
Manually annotated by BRENDA team
different isolates, gene lpxC
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-(2-acetamino)-2-deoxy-3-O-[2-(hexylamino)-1-methyl-2-oxoethyl]-D-glucopyranose + H2O
UDP-2-amino-2-deoxy-3-O-[2-(hexylamino)-1-methyl-2-oxoethyl]-D-glucopyranose + acetate
show the reaction diagram
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a homogenous fluorescence-based assay is developed that uses UDP–3-O-(N-hexyl-propionamide)-N-acetylglucosamine as a surrogate substrate. This surrogate can be prepared from commercially available UDP-GlcNAc by enzymatic conversion to UDP-MurNAc, which is then chemically coupled to n-hexylamine. Following the LpxC reaction, the free amine of the deacetylation product can be derivatized by fluorescamine, thus generating a fluorescent signal
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?
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine + H2O
UDP-3-((R)-3-hydroxytetradecanoyl)-alpha-D-glucosamine + acetate
show the reaction diagram
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-
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?
UDP-3-O-((3R)-3-hydroxydecanoyl)-N-acetylglucosamine + H2O
UDP-3-O-((3R)-3-hydroxydecanoyl)glucosamine + acetate
show the reaction diagram
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-
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-
?
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O
UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
show the reaction diagram
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O
UDP-3-O-((R)-3-hydroxymyristoyl)glucosamine + acetate
show the reaction diagram
UDP-3-O-(N-hexyl-propionamide)-N-acetylglucosamine + H2O
?
show the reaction diagram
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?
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
show the reaction diagram
UDP-N-acetylglucosamine + H2O
UDP-D-glucosamine + acetate
show the reaction diagram
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kcat/KM fo UDP-N-acetylglucosamine is 5000000-fold lower than the kcat/Km for UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O
UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
show the reaction diagram
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O
UDP-3-O-((R)-3-hydroxymyristoyl)glucosamine + acetate
show the reaction diagram
UDP-3-O-[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine + H2O
UDP-3-O-[(3R)-3-hydroxymyristoyl]-alpha-D-glucosamine + acetate
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
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incubation of apo-LpxC (0.125 mM) with stoichiometric amounts of Mn2+, Co2+, and Ni2+ reactivates apo-LpxC to varying degrees (Co2+, Ni2+ > Zn2+ > Mn2+)
Ni2+
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incubation of apo-LpxC (0.125 mM) with stoichiometric amounts of Mn2+, Co2+, and Ni2+ reactivates apo-LpxC to varying degrees (Co2+, Ni2+ > Zn2+ > Mn2+)
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2R)-4-([1,1'-biphenyl]-4-yl)-N-hydroxy-2-(methanesulfonyl)-2-methylbutanamide
(2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-(methanesulfonyl)-2-methylbutanamide
(2R)-N-hydroxy-2-(methanesulfonyl)-2-methyl-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanamide
(2R)-N-hydroxy-2-(methanesulfonyl)-2-methyl-4-(4-oxo-7-phenylquinazolin-3(4H)-yl)butanamide
(2R)-N-hydroxy-2-[(naphthalene-2-sulfonyl)methyl]-3-(naphthalen-2-yl)propanamide
A0A0J9X1N6
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(2R)-N-hydroxy-3-naphthalen-2-yl-2-[(naphthalen-2-ylsulfonyl)amino]propanamide
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potent inhibitor, shows antibacterial activity against a wide range of Gram-negative pathogens, binding mode
(2S,3R,4S,5R)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
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(2S,3R,4S,5R)-5-(1-hexyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
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(2S,3R,4S,5R)-5-[1-[(4-fluorophenyl)methyl]-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxyoxolane-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-[[4-(trifluoromethyl)phenyl]methyl]-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(2-(4-[2-(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(octa-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
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(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[2-(4-(2-[4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-5-[1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-((4-[(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenethyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-[4-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[(4-([4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]tetrahydrofuran-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-(4-phenylbuta-1,3-diyn-1-yl)phenyl]oxolane-2-carboxamide
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(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-([4-[(morpholin-4-yl)methyl]phenyl]ethynyl)phenyl]oxolane-2-carboxamide
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(3-(4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanethiol
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(3R,5R)-3-hydroxy-5-(2-(hydroxyamino)-2-oxoethyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yl tetradecanoate
(4R)-2-(3,4-dimethoxy-5-propylphenyl)-N-hydroxy-4,5-dihydro-1,3-oxazole-4-carboxamide
(4R)-N-hydroxy-2-(4-methoxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxamide
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i.e. L-159,692
(4R)-N-hydroxy-2-tricyclo[3.3.1.1-3,7]dec-1-yl-4,5-dihydro-1,3-oxazole-4-carboxamide
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1 microg/ml, high inhibitory activity
(R)-(hydroxyamino)((R)-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrothiazol-4-yl)methanol
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(R)-2-(1-butyl-1H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(2-bromophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, nearly complete loss of activity
(R)-2-(2-butyl-2H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(3,4-dichlorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, exellent biological activity
(R)-2-(3,4-difluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, exellent biological activity
(R)-2-(3,4-dimethoxy-5-propylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-2-(3,5-dichlorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(R)-2-(3,5-difluoro-4-methoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, good activity
(R)-2-(3,5-difluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(R)-2-(3,5-dimethoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 67% inhibition
(R)-2-(3-(dichloromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-2-(3-bromo-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, exellent biological activity
(R)-2-(3-chloro-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, exellent biological activity
(R)-2-(3-cyanophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-2-(3-ethoxy-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, slight lower inhibitory activity than (R)-2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
(R)-2-(3-fluoro-5-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, good activity
(R)-2-(4-(3-fluorobenzyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(4-(allyloxy)-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(4-(dimethylamino)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(4-(hexyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 86% inhibition
(R)-2-(4-(hydroxycarbamoyl)-4,5-dihydrooxazol-2-yl)benzyl benzoate
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1 microg/ml, nearly complete loss of activity
(R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide
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(R)-2-(4-chloro-3-nitrophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
(R)-2-(4-fluoro-3-methylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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(R)-2-(4-fluoro-3-nitrophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-2-(4-tert-butylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 58% inhibition
(R)-2-(biphenyl-4-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 69% inhibition
(R)-2-decyl-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, high inhibitory activity
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide
(R)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-2-isopropyl-4-oxobutanamide
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(R)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-2-methyl-4-oxobutanamide
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(R)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
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(R)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-1H-indazole-3-carboxamide
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(R)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-4-methoxy-3-propyl-5-(trifluoromethoxy)benzamide
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(R)-N-hydroxy-2-(1H-indazol-3-yl)-4,5-dihydrooxazole-4-carboxamide
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(R)-N-hydroxy-2-(2,3,5-trifluoro-4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, good activity
(R)-N-hydroxy-2-(2-methylprop-1-enyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(R)-N-hydroxy-2-(3,4,5-triethoxyphenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 72% inhibition
(R)-N-hydroxy-2-(3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, exellent inhibitory activity
(R)-N-hydroxy-2-(3-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 44% inhibition
(R)-N-hydroxy-2-(4-((3-nitrophenoxy)methyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
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(R)-N-hydroxy-2-(4-(3-nitrobenzyloxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
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(R)-N-hydroxy-2-(4-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-N-hydroxy-2-(4-hydroxyphenyl)-4,5-dihydrooxazole-4-carboxamide
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(R)-N-hydroxy-2-(4-methoxy-3,5-dimethylphenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, 71% inhibition
(R)-N-hydroxy-2-(4-methoxy-3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
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(R)-N-hydroxy-2-(4-methoxy-3-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-N-hydroxy-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
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(R)-N-hydroxy-2-(4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-N-hydroxy-2-(4-methyl-3-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-N-hydroxy-2-(4-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml
(R)-N-hydroxy-2-p-tolyl-4,5-dihydrothiazole-4-carboxamide
-
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(R,E)-2-(2-chlorostyryl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(R,E)-N-hydroxy-2-(3-(trifluoromethyl)styryl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(R,E)-N-hydroxy-2-(4-nitrostyryl)-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(R,E)-N-hydroxy-2-styryl-4,5-dihydrooxazole-4-carboxamide
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1 microg/ml, moderate activity
(S)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
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(S)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-5-methyl-4,5-dihydroisoxazole-5-carboxamide
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(S)-3-(4-methoxyphenyl)-4,5-dihydro-isoxazole-5-carboxylic acid hydroxyamide
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(S)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-2-methyl-4-oxobutanamide
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(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
1,5-anhydro-2-C-(carboxymethyl-N-hydroxyamide)-2-deoxy-3-O-myristoyl-D-glucitol
1,5-anhydro-2-deoxy-2-[(2Z)-2-hydroxy-2-(hydroxyimino)ethyl]-3-O-tetradecanoyl-L-mannitol
A0A0J9X1N6
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1,5-anhydro-2-deoxy-2-[2-(hydroxyamino)-2-oxoethyl]-3-O-tetradecanoyl-D-glucitol
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the X-ray crystal structure of LpxC complexed with TU-514 allows for a detailed examination of the coordination geometry of the catalytic zinc ion and other enzyme-inhibitor interactions in the active site. The hydroxamate group of TU-514 forms a bidentate chelate complex with the zinc ion and makes hydrogen bond interactions with conserved active site residues E78, H265, and T191. The inhibitor C-4 hydroxyl group makes direct hydrogen bond interactions with E197 and H58. Finally, the C-3 myristate moiety of the inhibitor binds in the hydrophobic tunnel of the active site
2,3-dihydroxy-benzaldehyde O-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-oxime
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weak inhibitor
2,4-dihydroxy-benzaldehyde O-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-oxime
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2-(1-butyl-1H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(2-butyl-2H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3,4-bis(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-N-hydroxyacetamide
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2-(3-allyl-5-fluoro-4-methoxy-2-methylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3-bromo-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3-bromo-5-fluoro-4-methoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3-chloro-4-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
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2-(3-chloro-5-fluoro-1H-indol-2-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3-ethoxy-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
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2-(3-fluoro-4-(2-(trifluoromethyl)benzyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
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2-(3-fluoro-4-(3-(trifluoromethyl)benzyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(3-fluoro-4-(3-methylbenzyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
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2-(3-fluoro-5-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(3-fluorobenzyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(allyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(allyloxy)-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(allyloxy)-3-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(but-3-enyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(but-3-enyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(but-3-enyloxy)phenyl)-N-hydroxy-4,5-dihydrothiazole-4-carboxamide
-
-
2-(4-(dimethylamino)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-(heptyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-acetamidophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-acetylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-bromophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-butylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-5,6-dihydro-4H-1,3-oxazine-4-carboxamide
-
-
2-(4-fluoro-3-methylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-fluoro-3-propylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(4-fluorophenyl)-N-hydroxy-4,5-dihydrothiazole-4-carboxamide
-
-
2-(5-fluoro-1H-indol-2-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
-
-
2-(5-fluoro-1H-indol-2-yl)-N-hydroxy-5,6-dihydro-4H-1,3-oxazine-4-carboxamide
-
-
2-mercapto-1-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]ethanone
-
racemate
2-thioacetyl-1-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]ethanone
-
racemate
2-[[4-(diethylamino)-2-hydroxyphenyl]carbonyl]benzoic acid
-
compound shows good activity against Escherichia coli and Pseudomonas aeruginosa
3,4,5-trihydroxy-benzaldehyde O-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-oxime
-
weak inhibitor, contains a 5 position hydroxyl and exhibits greatly reduced inhibitory potency
3,4-dihydroxy-benzaldehyde O-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-oxime
-
50 microM, 49% inhibition
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide
-
-
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid
-
-
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
-
-
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-5-methyl-4,5-dihydroisoxazole-5-carboxamide
-
-
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-5-propyl-4,5-dihydroisoxazole-5-carboxamide
-
-
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-N-methyl-4,5-dihydroisoxazole-5-carboxamide
-
-
3-(4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl(methyl)phosphinic acid
-
-
3-ethoxy-4-fluoro-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)benzamide
-
-
4-(3-(cyclopentyloxy)-4-methoxyphenyl)-4-oxobutanoic acid
-
-
4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-4-oxobutanamide
-
-
4-(allyloxy)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-3-(trifluoromethoxy)benzamide
-
-
4-(but-3-enyloxy)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)benzamide
-
-
4-({4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
4-({4-[(4-{[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl}phenyl)ethynyl]phenoxy}methyl)-N-hydroxyoxane-4-carboxamide
4-({[4-(4-chlorophenoxy)phenyl]sulfanyl}methyl)-N-hydroxyoxane-4-carboxamide
4-fluoro-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)benzamide
-
-
4-[(4-{2-[(dimethylamino)methyl]morpholin-4-yl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
4-[(4-{[4-({2-[(dimethylamino)methyl]morpholin-4-yl}methyl)phenyl]ethynyl}phenoxy)methyl]-N-hydroxyoxane-4-carboxamide
4-{[4-(4-acetylpiperazin-1-yl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
4-{[4-({4-[(4-acetylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}-N-hydroxyoxane-4-carboxamide
5'-O-[(E)-(2,3,4-trihydroxybenzylidene)amino]uridine
5'-O-[(E)-(3,4-dihydroxybenzylidene)amino]uridine
6-(1H-benzimidazol-1-yl)-N-hydroxy-5-[4-([6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]ethynyl)phenyl]pyridine-3-carboxamide
crystal structure of inhibitor B bound to the enzyme
Ciprofloxacin
dipicolinic acid
-
0.02 mM, complete inhibition
meropenem
N'-formyl-3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carbohydrazide
-
-
N,4-dihydroxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
N-(((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-2-((Z)-2,3,4-trihydroxybenzylideneaminooxy)acetamide
-
-
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide
N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-1H-indazole-3-carboxamide
-
-
N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-4-(trifluoromethoxy)benzamide
-
-
N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-4-methoxy-3-propyl-5-(trifluoromethoxy)benzamide
-
-
N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-4-methylbenzamide
-
-
N-ethylmaleimide
-
1 mM, complete inhibition
N-hydroxy-2-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(1H-indazol-3-yl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(2-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(3-(trifluoromethyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(3-propyl-4,5-bis(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4'-propylbiphenyl-4-yl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-((3-nitrophenoxy)methyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-(3-methylbut-2-enyloxy)-3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-(3-nitrobenzyloxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-(trifluoromethoxy)phenyl)-4,5-dihydrothiazole-4-carboxamide
-
-
N-hydroxy-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-hydroxyphenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-iodophenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-methoxy-3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrothiazole-4-carboxamide
-
-
N-hydroxy-2-(4-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-4,5-dihydrothiazole-4-carboxamide
-
-
N-hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-p-tolyl-4,5-dihydrooxazole-4-carboxamide
-
-
N-hydroxy-2-p-tolyl-4,5-dihydrothiazole-4-carboxamide
-
-
N-hydroxy-2-p-tolyl-5,6-dihydro-4H-1,3-oxazine-4-carboxamide
-
-
N-hydroxy-4-({4-[(4-{[4-(propan-2-yl)piperazin-1-yl]methyl}phenyl)ethynyl]phenoxy}methyl)oxane-4-carboxamide
N-hydroxy-4-({4-[4-(propan-2-yl)piperazin-1-yl]phenoxy}methyl)oxane-4-carboxamide
N-hydroxy-4-({[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenyl]sulfanyl}methyl)oxane-4-carboxamide
N-hydroxy-4-methoxy-1-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}cyclohexane-1-carboxamide
N-hydroxy-4-[(4-{4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}phenoxy)methyl]oxane-4-carboxamide
N-hydroxy-4-[(4-{[4-({4-[2-(1H-imidazol-1-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)-2-oxoethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
N-hydroxy-4-[(4-{[4-({4-[2-(morpholin-4-yl)ethyl]piperazin-1-yl}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
N-hydroxy-4-[(4-{[4-({[(4-methoxyphenyl)methyl]amino}methyl)phenyl]ethynyl}phenoxy)methyl]oxane-4-carboxamide
N-hydroxy-4-{[4-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzene-1-sulfinyl]methyl}oxane-4-carboxamide
N-hydroxy-4-{[4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenoxy]methyl}oxane-4-carboxamide
N-hydroxy-6-(1H-imidazol-1-yl)-5-[4-([6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]ethynyl)phenyl]pyridine-3-carboxamide
-
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-((4-[(morpholin-4-yl)methyl]phenyl)ethynyl)benzamide
-
-
-
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-(4-phenylbuta-1,3-diyn-1-yl)benzamide
A0A0J9X1N6
-
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-([6-[(morpholin-4-yl)methyl]pyridin-3-yl]ethynyl)benzamide
-
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzamide
N-[3-amino-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[4-(phenylethynyl)phenyl]piperazine-1-carboxamide
-
compound shows good activity against Escherichia coli and Pseudomonas aeruginosa
N-[3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-(phenylethynyl)benzamide
-
compound shows good activity against Escherichia coli and Pseudomonas aeruginosa
N-[3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[4-(phenylethynyl)phenyl]piperidine-1-carboxamide
-
compound shows good activity against Escherichia coli and Pseudomonas aeruginosa
N-[3-hydroxy-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-[4-(phenylethynyl)phenyl]piperazine-1-carboxamide
-
compound shows good activity against Escherichia coli and Pseudomonas aeruginosa
RS-130830
-
tobramycin
[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphonic acid
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
-
addition of bovine serum albumin slightly increases activity
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.367
UDP-(2-acetamino)-2-deoxy-3-O-[2-(hexylamino)-1-methyl-2-oxoethyl]-D-glucopyranose
-
pH 6.0, 30°C
0.00032 - 0.0007
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine
0.00019 - 0.011
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.5 - 8.83
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine
0.00096 - 3.3
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine
0.36
UDP-3-O-(N-hexyl-propionamide)-N-acetylglucosamine
Escherichia coli
-
pH 6.0, 30°C
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.98
UDP-(2-acetamino)-2-deoxy-3-O-[2-(hexylamino)-1-methyl-2-oxoethyl]-D-glucopyranose
Escherichia coli
-
pH 6.0, 30°C
75823
2833 - 16500
UDP-3-((R)-3-hydroxytetradecanoyl)-N-acetyl-alpha-D-glucosamine
9763
0.52 - 7895
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine
2060
0.00028
UDP-N-acetylglucosamine
Escherichia coli
-
pH 5.7, 30°C
383
additional information
additional information
2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0147
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
-
above, pH 6.0, 37°C
-
0.00402 - 0.0044
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-(4-phenylbuta-1,3-diyn-1-yl)phenyl]oxolane-2-carboxamide
0.00065
(3R,5R)-3-hydroxy-5-(2-(hydroxyamino)-2-oxoethyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yl tetradecanoate
0.00002 - 0.0058
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide
0.00005 - 0.38
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
0.054
5'-O-[(E)-(2,3,4-trihydroxybenzylidene)amino]uridine
-
-
0.000002 - 0.00034
N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide
0.000008
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-((4-[(morpholin-4-yl)methyl]phenyl)ethynyl)benzamide
-
pH 6.0, 37°C
-
additional information
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
-
Ki value is higher than 500 microM
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000001 - 0.000041
(2R)-4-([1,1'-biphenyl]-4-yl)-N-hydroxy-2-(methanesulfonyl)-2-methylbutanamide
0.000000069 - 0.000183
(2R)-4-[4-(2-fluoro-4-methoxyphenyl)-2-oxopyridin-1(2H)-yl]-N-hydroxy-2-(methanesulfonyl)-2-methylbutanamide
0.00000068 - 0.00011
(2R)-N-hydroxy-2-(methanesulfonyl)-2-methyl-4-(2-oxo-4-phenylpyridin-1(2H)-yl)butanamide
0.00000023
(2R)-N-hydroxy-2-(methanesulfonyl)-2-methyl-4-(4-oxo-7-phenylquinazolin-3(4H)-yl)butanamide
Pseudomonas aeruginosa
P47205
pH and temperature not specified in the publication
0.2
(2S,3R,4S,5R)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-5-(1-hexyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxyoxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-5-[1-[(4-fluorophenyl)methyl]-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxyoxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(1-[[4-(trifluoromethyl)phenyl]methyl]-1H-1,2,3-triazol-4-yl)oxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(2-(4-[2-(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
-
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(octa-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.107
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
-
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(2-phenylethyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]oxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.2
(2S,3R,4S,5R)-N,3,4-trihydroxy-5-[2-(4-(2-[4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
-
0.2
(2S,3R,4S,5S)-5-(1-benzyl-1H-1,2,3-triazol-4-yl)-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.2
(2S,3R,4S,5S)-5-[1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-N,3,4-trihydroxytetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-((4-[(4-methoxyphenyl)ethynyl]phenyl)ethynyl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
-
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenethyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-phenyl-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(1-[4-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
-
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-(phenylbuta-1,3-diyn-1-yl)tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-([4-(phenylethynyl)phenyl]ethynyl)tetrahydrofuran-2-carboxamide, (2S,3R,4S,5S)-N,3,4-trihydroxy-5-[(4-([4-(trifluoromethyl)phenyl]ethynyl)phenyl)ethynyl]tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
-
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]tetrahydrofuran-2-carboxamide
Escherichia coli
-
above, pH 6.0, 37°C
0.0305 - 0.032
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-(4-phenylbuta-1,3-diyn-1-yl)phenyl]oxolane-2-carboxamide
0.2
(2S,3R,4S,5S)-N,3,4-trihydroxy-5-[4-([4-[(morpholin-4-yl)methyl]phenyl]ethynyl)phenyl]oxolane-2-carboxamide
Escherichia coli
-
pH 6.0, 37°C
0.022
(3-(4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanethiol
Escherichia coli
-
pH 6.0, 30°C
26 - 75
(4R)-2-(3,4-dimethoxy-5-propylphenyl)-N-hydroxy-4,5-dihydro-1,3-oxazole-4-carboxamide
2500 - 2600
(4R)-N-hydroxy-2-(4-methoxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxamide
0.0178
(R)-(hydroxyamino)((R)-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrothiazol-4-yl)methanol
Pseudomonas aeruginosa
-
-
0.01
(R)-2-(1-butyl-1H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.012
(R)-2-(2-butyl-2H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.000097
(R)-2-(3,4-dimethoxy-5-propylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Escherichia coli
-
-
0.00033
(R)-2-(3,5-difluoro-4-methoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Escherichia coli
-
-
0.0068
(R)-2-(3,5-difluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Escherichia coli
-
-
0.001
(R)-2-(3-ethoxy-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00025
(R)-2-(4-(3-fluorobenzyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0022
(R)-2-(4-(allyloxy)-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0049
(R)-2-(4-(dimethylamino)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00075
(R)-2-(4-(hexyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Escherichia coli
-
-
0.0004
(R)-2-(4-bromophenylsulfonamido)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxypropanamide
Escherichia coli
-
-
0.025
(R)-2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0012
(R)-2-(4-fluoro-3-methylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00016
(R)-3-(5,8-dihydronaphthalen-2-yl)-N-hydroxy-2-(naphthalene-2-sulfonamido)propanamide
Escherichia coli
-
-
0.138
(R)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-2-isopropyl-4-oxobutanamide
Pseudomonas aeruginosa
-
-
0.00891
(R)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-2-methyl-4-oxobutanamide
Pseudomonas aeruginosa
-
-
0.003
(R)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
Escherichia coli
-
pH 6.0, 30°C
0.013
(R)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-1H-indazole-3-carboxamide
Pseudomonas aeruginosa
-
-
0.0055
(R)-N-hydroxy-2-(1H-indazol-3-yl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0016
(R)-N-hydroxy-2-(2,3,5-trifluoro-4-methoxyphenyl)-4,5-dihydrooxazole-4-carboxamide
Escherichia coli
-
-
0.00056
(R)-N-hydroxy-2-(4-((3-nitrophenoxy)methyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.001
(R)-N-hydroxy-2-(4-(3-nitrobenzyloxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00016
(R)-N-hydroxy-2-(4-methoxy-3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0005
(R)-N-hydroxy-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0385
(R)-N-hydroxy-2-p-tolyl-4,5-dihydrothiazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0162
(S)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.0229
(S)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-5-methyl-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.00437
(S)-3-(4-methoxyphenyl)-4,5-dihydro-isoxazole-5-carboxylic acid hydroxyamide
Escherichia coli
-
pH 6.0, 30°C
0.00891
(S)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-2-methyl-4-oxobutanamide
Pseudomonas aeruginosa
-
-
0.00044
(S)-N-(1-(2-(3,4-dimethoxy-5-propylphenyl)-4,5-dihydrooxazol-4-yl)vinyl)hydroxylamine
Escherichia coli
-
-
0.01
2-(1-butyl-1H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.012
2-(2-butyl-2H-indazol-3-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.000162
2-(3,4-bis(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0204
2-(3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-N-hydroxyacetamide
Pseudomonas aeruginosa
-
-
0.001 - 0.0033
2-(3-allyl-5-fluoro-4-methoxy-2-methylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0049 - 0.00501
2-(3-bromo-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.009 - 0.00912
2-(3-bromo-5-fluoro-4-methoxyphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.03 - 0.0302
2-(3-chloro-4-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0003 - 0.00159
2-(3-chloro-5-fluoro-1H-indol-2-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.001 - 0.0468
2-(3-ethoxy-4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0096
2-(3-fluoro-4-(2-(trifluoromethyl)benzyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00084
2-(3-fluoro-4-(3-(trifluoromethyl)benzyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.000851
2-(3-fluoro-4-(3-methylbenzyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.025 - 0.0251
2-(3-fluoro-5-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.00025 - 0.000251
2-(4-(3-fluorobenzyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.00012
2-(4-(allyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0022 - 0.00223
2-(4-(allyloxy)-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0014
2-(4-(allyloxy)-3-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00035 - 0.000355
2-(4-(but-3-enyloxy)-3-(trifluoromethoxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0056 - 0.00562
2-(4-(but-3-enyloxy)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0587 - 0.0589
2-(4-(but-3-enyloxy)phenyl)-N-hydroxy-4,5-dihydrothiazole-4-carboxamide
0.0049 - 0.00501
2-(4-(dimethylamino)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.018 - 0.0182
2-(4-acetylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0027
2-(4-bromophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0073 - 0.007413
2-(4-butylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0013 - 0.00132
2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0212
2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-hydroxy-5,6-dihydro-4H-1,3-oxazine-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0012
2-(4-fluoro-3-methylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.000955 - 0.00096
2-(4-fluoro-3-propylphenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.006 - 0.00603
2-(4-fluorophenyl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
0.0625
2-(4-fluorophenyl)-N-hydroxy-4,5-dihydrothiazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0016
2-(5-fluoro-1H-indol-2-yl)-N-hydroxy-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0312
2-(5-fluoro-1H-indol-2-yl)-N-hydroxy-5,6-dihydro-4H-1,3-oxazine-4-carboxamide
Pseudomonas aeruginosa
-
-
0.027
2-mercapto-1-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]ethanone
Escherichia coli
-
racemate, pH 6.0, 30°C
0.012
2-thioacetyl-1-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]ethanone
Escherichia coli
-
racemate, pH 6.0, 30°C
0.000002
2-[[4-(diethylamino)-2-hydroxyphenyl]carbonyl]benzoic acid
Escherichia coli
-
pH not specified in the publication, temperature not specified in the publication
0.03
3,4-dihydroxy-benzaldehyde O-[5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-oxime
Escherichia coli
-
-
0.0138
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.0162
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid
Pseudomonas aeruginosa
-
-
0.479
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.0263
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-5-methyl-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.00661
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-5-propyl-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.00427
3-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-N-methyl-4,5-dihydroisoxazole-5-carboxamide
Pseudomonas aeruginosa
-
-
0.17
3-(4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl(methyl)phosphinic acid
Escherichia coli
-
pH 6.0, 30°C
0.046
3-ethoxy-4-fluoro-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)benzamide
Pseudomonas aeruginosa
-
-
0.00427
4-(3-(cyclopentyloxy)-4-methoxyphenyl)-4-oxobutanoic acid
Pseudomonas aeruginosa
-
-
0.0148
4-(3-(cyclopentyloxy)-4-methoxyphenyl)-N-hydroxy-4-oxobutanamide
Pseudomonas aeruginosa
-
-
0.0075 - 0.00759
4-(allyloxy)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-3-(trifluoromethoxy)benzamide
0.0039 - 0.00398
4-(but-3-enyloxy)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)benzamide
0.027
5'-O-[(E)-(2,3,4-trihydroxybenzylidene)amino]uridine
Escherichia coli
-
-
0.00000048
6-(1H-benzimidazol-1-yl)-N-hydroxy-5-[4-([6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]ethynyl)phenyl]pyridine-3-carboxamide
Pseudomonas aeruginosa
P47205
pH and temperature not specified in the publication
0.4
N'-formyl-3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carbohydrazide
Escherichia coli
-
pH 6.0, 30°C
0.12
N-(((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-2-((Z)-2,3,4-trihydroxybenzylideneaminooxy)acetamide
Escherichia coli
-
-
0.0129 - 0.013
N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-1H-indazole-3-carboxamide
0.00154
N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-4-(trifluoromethoxy)benzamide
Pseudomonas aeruginosa
-
-
0.0055 - 0.00562
N-hydroxy-2-(1H-indazol-3-yl)-4,5-dihydrooxazole-4-carboxamide
0.006 - 0.00603
N-hydroxy-2-(3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
0.0025 - 0.00251
N-hydroxy-2-(3-(trifluoromethyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
0.0005 - 0.000501
N-hydroxy-2-(3-propyl-4,5-bis(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
0.00028 - 0.000282
N-hydroxy-2-(4'-propylbiphenyl-4-yl)-4,5-dihydrooxazole-4-carboxamide
0.00056 - 0.000562
N-hydroxy-2-(4-((3-nitrophenoxy)methyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
0.00019
N-hydroxy-2-(4-(3-methylbut-2-enyloxy)-3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.001
N-hydroxy-2-(4-(3-nitrobenzyloxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.005 - 0.00501
N-hydroxy-2-(4-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
0.0217
N-hydroxy-2-(4-(trifluoromethoxy)phenyl)-4,5-dihydrothiazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0078 - 0.00794
N-hydroxy-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazole-4-carboxamide
0.0055
N-hydroxy-2-(4-iodophenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.00016
N-hydroxy-2-(4-methoxy-3-(trifluoromethoxy)phenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0178
N-hydroxy-2-(4-methoxy-3-propyl-5-(trifluoromethoxy)phenyl)-4,5-dihydrothiazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.0054
N-hydroxy-2-(4-nitrophenyl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.01
N-hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)-4,5-dihydrooxazole-4-carboxamide
Pseudomonas aeruginosa
-
-
0.02 - 0.0204
N-hydroxy-2-p-tolyl-4,5-dihydrooxazole-4-carboxamide
0.0385 - 0.0389
N-hydroxy-2-p-tolyl-4,5-dihydrothiazole-4-carboxamide
0.00000064
N-hydroxy-6-(1H-imidazol-1-yl)-5-[4-([6-[(4-methylpiperazin-1-yl)methyl]pyridin-3-yl]ethynyl)phenyl]pyridine-3-carboxamide
Pseudomonas aeruginosa
P47205
pH and temperature not specified in the publication
0.00006
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-((4-[(morpholin-4-yl)methyl]phenyl)ethynyl)benzamide
Escherichia coli
-
pH 6.0, 37°C
-
0.00000063
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-([6-[(morpholin-4-yl)methyl]pyridin-3-yl]ethynyl)benzamide
Pseudomonas aeruginosa
P47205
pH and temperature not specified in the publication
0.0000006
N-[3-amino-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[4-(phenylethynyl)phenyl]piperazine-1-carboxamide
Escherichia coli
-
pH not specified in the publication, temperature not specified in the publication
0.0000024
N-[3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-(phenylethynyl)benzamide
Escherichia coli
-
pH not specified in the publication, temperature not specified in the publication
0.0000138
N-[3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[4-(phenylethynyl)phenyl]piperidine-1-carboxamide
Escherichia coli
-
pH not specified in the publication, temperature not specified in the publication
0.0000003
N-[3-hydroxy-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]-4-[4-(phenylethynyl)phenyl]piperazine-1-carboxamide
Escherichia coli
-
pH not specified in the publication, temperature not specified in the publication
0.007 - 0.024
Zn2+
0.004
[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphonic acid
Escherichia coli
-
pH 6.0, 30°C
additional information
(R)-N-(3-hydroxy-1-(hydroxyamino)-1-oxopropan-2-yl)-4-methoxy-3-propyl-5-(trifluoromethoxy)benzamide
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.96
-
overproducing strain
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
assay at
5.9
-
assay at
7
-
assay at
additional information
-
affinity of EcLpxC for the product (myrUDP-GlcNH2) is determined as a function of pH to ascertain whether there are ionizations important for binding affinity. For wild-type LpxC, the KD product value increases at both low and high pH in a log-linear fashion, indicating that two ionizations affect binding affinity
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 7
-
pH 5.0: about 45% of maximal activity, pH 7.0: about 60% of maximal activity
7 - 9
-
pH 7.0: about 55% of maximal activity, pH 9.0: about 75% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
assay at
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
29000
recombinant enzyme, gel filtration
33107
1 * 33107, recombinant enzyme, mass spectrometry
33435
-
x * 33435, calculated from sequence
34000
-
x * 34000, SDS-PAGE
38600
-
x * 38600, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
1 * 33107, recombinant enzyme, mass spectrometry
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2.7 A resolution X-ray crystal structure of LpxC complexed with the substrate analogue inhibitor, 1,5-anhydro-2-C-(carboxymethyl-N-hydroxamide)-2-deoxy-3-O-myristoyl-D-glucitol, and the 2.0 A resolution structure of LpxC complexed with imidazole. The X-ray crystal structure of LpxC complexed with 1,5-anhydro-2-C-(carboxymethyl-N-hydroxamide)-2-deoxy-3-O-myristoyl-D-glucitol allows for a detailed examination of the coordination geometry of the catalytic zinc ion and other enzyme-inhibitor interactions in the active site. The hydroxamate group of 1,5-anhydro-2-C-(carboxymethyl-N-hydroxamide)-2-deoxy-3-O-myristoyl-D-glucitol forms a bidentate chelate complex with the zinc ion and makes hydrogen bond interactions with conserved active site residues E78, H265, and T191. The inhibitor C-4 hydroxyl group makes direct hydrogen bond interactions with E197 and H58. Finally, the C-3 myristate moiety of the inhibitor binds in the hydrophobic tunnel of the active site
-
Aquifex aeolicus LpxC with bound UDP-3-O-(acyl)-glucosamine and with 2 and 9, X-ray diffraction structure determination and analysis. Cocrystal structure of Aquifex aeolicus LpxC with bound product UDP-3-O-(acyl)-glucosamine and Pseudomonas aeruginosa with bound 27b docking model, overview
crystal structure of the LpxC-3-(heptyloxy)benzoate complex
-
crystallization at 21°C, a sitting drop containing 0.005 ml of protein solution (2.2 mg/ml LpxC, 25 mM Hepes (pH 7.0), 50 mM NaCl, 10 mM magnesium acetate, and 0.5 mM ZnSO4) is equilibrated against a 0.5 ml reservoir of 0.8 M NaCl/0.1 M Hepes (pH 7.0). Crystals of dimensions 0.3 * 0.1 * 0.05 mm3 appear in 5-7 days, larger crystals of dimensions 0.6 * 0.2 * 0.2 mm3 are obtained by macroseeding
-
crystals of LpxC are grown by hanging-drop vapour diffusion at 20°C, structure of recombinant UDP-3-O-acyl-N-acetylglucosamine deacetylase in complex with UDP, determined to a resolution of 2.2 A. The uracil-binding site is constructed from amino acids that are highly conserved across species. Hydrophobic associations with the Phe155 and Arg250 side chains in combination with hydrogen-bonding interactions with the main chain of Glu154 and the side chains of Tyr151 and Lys227 position the base. The phosphate and ribose groups are directed away from the active site and interact with Arg137, Lys156, Glu186 and Arg250
-
equilibrating a hanging drop containing 0.003 ml of protein solution (3 mg/ml LpxC, 100 mM HEPES, pH 7.5, 180 mM NaCl, 9-14% PEG3350, and 0.5 mM ZnSO4) and 0.003 ml of precipitant buffer (100 mM HEPES, pH 7.5, 180 mM NaCl, 9-14% PEG3350, and 0.5 mM ZnSO4) over a reservoir containing about 1 ml of precipitant buffer. Crystals with maximum dimensions of 0.3 * 0.15 * 0.15 mm3 grow within 3 days and are gradually transferred to a stabilization buffer of 100 mM sodium cacodylate, pH 6.0, 180 mM NaCl, 11-16% PEG 3350, 0.5 mM ZnSO4, and 1% glycerol. Crystals are flash-cooled in liquid nitrogen following cryoprotection with 22% glycerol and diffracted X-rays to 2.1 Å. Crystals are isomorphous with those prepared at pH 7.0 and belong to space group P6(1) with unit cell dimensions a = b = 101.3 A, c = 122.7 A
purified enzyme mutant C125S in complex with product UDP-(3-O-(R-3-hydroxymyristoyl))-glucosamine, hanging-drop vapor diffusion, mixing of 12 mg/ml protein in 20 mM HEPES, pH 7.0, 50 mM NaCl, and 0.5 mM zinc sulfate, with reservori solution containing 0.4 M NaH2PO4, 0.8 M K2HPO4, 0.2 M CAPS, pH 10.5, 50mM Li2SO4, 20°C, 3 days, X-ray diffraction structure determination and analysis at 2.59 A resolution, modeling
A0A0J9X1N6
1.9 A resolution crystal structure of LpxC complexed with (2R)-N-hydroxy-3-naphthalen-2-yl-2-[(naphthalen-2-ylsulfonyl)amino]propanamide
-
purified recombinant truncated enzyme mutant C40S in complex with inhibitor B, sitting drop vapor diffusion method, 2 days to 4 months, X-ray diffraction structure determination and analysis at 2.06 A resolution, molecular replacement, LpxC binding to the inhibitor increases protein solubility, shortens crystallization time and leads to a high-resolution crystal structure, to reduce the amount of compound needed, an overexpression strain of Escherichia coli is created lacking acrB, a critical component of the major efflux pump
X-ray diffraction structure determination and analysis
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
6 h, stable
60
-
stable for up to 20 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
purified enzyme is unstable, decay half-life of approximately 40 h
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
C193A/DELTAD284-L294 variant of LpxC
-
pulldown method to rapidly purify tagged LpxC under anaerobic conditions
-
recombinant enzyme mutant LpxC C63A by two different steps of anion exchange chromatography, and gel filtration
-
recombinant truncated enzyme mutant C40S from Escherichia coli by anion exchange and hydrophobic interaction chromatography, ultrafiltration, and gel filtration. The inhibitors remain bound to LpxC throughout purification
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
C193A/DELTAD284-L294 variant of LpxC overexpressed in Escherichia coli
-
envA is cloned into an isopropyl-1-thio-beta-D-galactopyranoside-inducible T7-based expression system
-
Escherichia coli BL21 is used as host for expression of Strep-tagged LpxC protein
-
expression in Escherichia coli
expression in Pseudomonas aeruginosa
-
gene envA or lpxC, functional overexpression of the first 299 amino acids out of 303 of enzyme mutant C40S in an Escherichia coli strain BL21(DE3) pLysS, and with its inhibitors in the acrB-deficient variant strain BL21(DE3) DELTAacrB pLysS or ARC5329
gene lpxC, recombinant expression of enzyme mutant LpxC C63A
-
overepression of LpxC variants in Escherichia coli
subcloned the Pseudomonas aeruginosa lpxC gene into the T7-based expression vector pET11a
-
the paLpxC (residues 1-299, C40S) is cloned from genomic DNA by polymerase chain reaction and inserted into pPW4 expression vectors. The recombinant paLpxC is overexpressed
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C193A/DELTAD284-L294
-
variant of LpxC
D105A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 56% of the specific activity of the wild-type extract
D105N
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 67% of the specific activity of the wild-type extract
D105S
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 78% of the specific activity of the wild-type extract
D246N
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 3.5% of the specific activity of the wild-type extract
D246S
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about less than 0.0005% of the specific activity of the wild-type extract
E100A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 72% of the specific activity of the wild-type extract
E100N
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 61% of the specific activity of the wild-type extract
E100S
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 83% of the specific activity of the wild-type extract
E234A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 4.8% of the specific activity of the wild-type extract
E234N
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about less than 0.0005% of the specific activity of the wild-type extract
E234S
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 6.7% of the specific activity of the wild-type extract
E78A/H265A
decrease in kcat/KM compared to wild-type Zn2+-containing enzyme
E78Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about less than 0.0005% of the specific activity of the wild-type extract
H19A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 5% of the specific activity of the wild-type extract. Contains 51% Fe2+ compared to wild-type Zn2+ content
H19Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 45% of the specific activity of the wild-type extract
H19Y
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 4.4% of the specific activity of the wild-type extract
H238A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.1% of the specific activity of the wild-type extract. Extract overexpressing H238A is stimulated approximately 20fold by the addition of ZnSO4
H265A
decrease in kcat/KM compared to wild-type Zn2+-containing enzyme
H265Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about less than 0.0005% of the specific activity of the wild-type extract
H79A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.006% of the specific activity of the wild-type extract. Contains 10% Fe2+ compared to wild-type Zn2+ content. Extract overexpressing H79A is stimulated approximately 20fold by the addition of ZnSO4
H79Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.008% of the specific activity of the wild-type extract
K227E
-
completely inactive mutant enzyme
T179A
-
LpxC mutant is less sensitive to N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide inhibition
C125A
-
as sensitive to 2,3,4-trihydroxybenzaldehyde O-((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl oxime as the wild-type enzyme
C125S
A0A0J9X1N6
site-directed mutagenesis, crystal structure analysis
C207A
-
much less sensitive to 2,3,4-trihydroxybenzaldehyde O-((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl oxime inhibition, suggesting that Cys-207 is necessary to form the E-I complex
C214N
-
as sensitive to 2,3,4-trihydroxybenzaldehyde O-((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl oxime as the wild-type enzyme
C250A
-
as sensitive to 2,3,4-trihydroxybenzaldehyde O-((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl oxime as the wild-type enzyme
C63S
-
as sensitive to 2,3,4-trihydroxybenzaldehyde O-((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl oxime as the wild-type enzyme
C65A
-
as sensitive to 2,3,4-trihydroxybenzaldehyde O-((2R,3R,4S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl oxime as the wild-type enzyme
D197A
-
site-directed mutagenesis
D197E
-
site-directed mutagenesis
D242A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 9.5% of the specific activity of the wild-type extract
D242Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.04% of the specific activity of the wild-type extract
E78A/H265A
-
14800fold decrease in kcat/KM compared to wild-type Zn2+-containing enzyme
E78Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.03% of the specific activity of the wild-type extract
F192A
-
site-directed mutagenesis
H238A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.09% of the specific activity of the wild-type extract
H265Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.02% of the specific activity of the wild-type extract
H79A
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.04% of the specific activity of the wild-type extract
H79Q
-
expressed to level comparable to wild-type LpxC. The extract overexpressing LpxC exhibits about 0.08% of the specific activity of the wild-type extract
I38T
-
lpxC gene
K143A
-
site-directed mutagenesis
K239A
-
site-directed mutagenesis
N162A
-
site-directed mutagenesis
Q202W/G210S
T191A
-
site-directed mutagenesis
I38T
-
lpxC gene
-
G17S
-
partially-inactivated LpxC mutant G17S
-
C40S
site-directed mutagenesis, crystal structure analysis
S214G
completely inhibited by 0.5 microM N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide, wild-type under the same conditions 50% inhibited
W206Q/S214G
completely inhibited by 0.5 microM N-((2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide, wild-type under the same conditions 50% inhibited
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
medicine
pharmacology
the enzyme is a target for antibiotic therapy and structure-based drug design
synthesis
-
construction of immobilized metal affinity membrane via coupling of epichlorohydrin, iminodiacetic acid, and nickel ion on a regenerated cellulose membrane. The D-hydantoin-hydrolyzing enzyme harboring a poly-His tagged residue is immobilized on the prepared membrane. By employing a membrane with nickel ion of 155.5 micromol/disc immersed in 0.1 M Tris-HCl buffer pH 8, with 0.8 M sodium chloride, an enzyme activity of 4.2 U/disc is obtained. The immobilized DHTase membrane can achieve a larger pH and thermaltolerance range than the free enzyme. 99% of enzyme activity can be retained after 15 repeated uses
Show AA Sequence (6538 entries)
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