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Literature summary extracted from

  • Nie, Z.; Perretta, C.; Lu, J.; Su, Y.; Margosiak, S.; Gajiwala, K.S.; Cortez, J.; Nikulin, V.; Yager, K.M.; Appelt, K.; Chu, S.
    Structure-based design, synthesis, and study of potent inhibitors of beta-ketoacyl-acyl carrier protein synthase III as potential antimicrobial agents (2005), J. Med. Chem., 48, 1596-1609.
    View publication on PubMed

Application

EC Number Application Comment Organism
2.3.1.180 drug development the highly conserved enzyme is an attractive target for antimicrobial inhibitor design Enterococcus faecalis

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.3.1.180 purified recombinant free enzyme, hanging drop vapour diffusion method, 20 mg/ml protein at 15°C with 0.2 M lithium sulfate, 0.1 M Bis-Tris, pH 6.5, 25% PEG 3350, enzyme mutant D36A/E37A with 2-[4-(3,5-dimethylpiperidin-1-yl)-3-phenoxybenzoylamino]benzoic acid, in 25% PEG 3350, 0.2 M ammonium sulfate, and 0.1 M Bis-Tris, pH 5.5, X-ray diffraction structure determination and analysis at 1.8 A resolution Enterococcus faecalis

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.3.1.180 14-bromo-3-diethylsulfamoyl-5-methylbenzoic acid
-
Enterococcus faecalis
2.3.1.180 2-(3-bromobenzoylamino)benzoic acid methyl ester
-
Enterococcus faecalis
2.3.1.180 2-(3-diethylsulfamoyl-4-fluorobenzoylamino)benzoic acid IC50 is 0.0084 mM Enterococcus faecalis
2.3.1.180 2-(3-diethylsulfamoyl-4-methoxybenzoylamino)benzoic acid IC50 is 0.0114 mM Enterococcus faecalis
2.3.1.180 2-(3-diethylsulfamoyl-4-phenoxybenzoylamino)benzoic acid IC50 is 0.0061 mM Enterococcus faecalis
2.3.1.180 2-(3-diethylsulfamoyl-4-piperidin-1-ylbenzoylamino)benzoic acid IC50 is 0.0022 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxy-4-piperazin-1-ylbenzoylamino)benzoic acid IC50 is 0.185 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxy-4-piperidin-1-ylbenzoylamino)benzoic acid IC50 is 0.00029 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxy-4-pyridin-3-ylbenzoylamino)benzoic acid IC50 is 0.00011 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxy-4-thiomorpholin-4-ylbenzoylamino)benzoic acid IC50 is 0.0012 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxybenzoylamino)benzoic acid IC50 is 0.0027 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxybenzoylamino)nicotinic acid IC50 is above 1.0 mM Enterococcus faecalis
2.3.1.180 2-(3-phenoxybenzoylamino)thiophene-3-carboxylic acid IC50 is 0.043 mM Enterococcus faecalis
2.3.1.180 2-(4-bromo-3-diethylsulfamoyl-5-methylbenzoylamino)-benzoic acid IC50 is 0.16 mM Enterococcus faecalis
2.3.1.180 2-(4-bromo-3-diethylsulfamoylbenzoylamino)-benzoic acid IC50 is 0.0016 mM Enterococcus faecalis
2.3.1.180 2-(4-bromo-3-phenoxybenzoylamino)-6-hydroxybenzoic acid IC50 is 0.000062 mM Enterococcus faecalis
2.3.1.180 2-(4-bromo-3-phenoxybenzoylamino)-6-methoxybenzoic acid
-
Enterococcus faecalis
2.3.1.180 2-(4-bromo-3-phenoxybenzoylamino)benzoic acid IC50 is 0.0011 mM Enterococcus faecalis
2.3.1.180 2-(4-bromo-3-phenoxybenzoylamino)benzoic acid methyl ester
-
Enterococcus faecalis
2.3.1.180 2-(4-cyclopentylmethoxy-3-diethylsulfamoylbenzoylamino)benzoic acid IC50 is 0.0021 mM Enterococcus faecalis
2.3.1.180 2-(4-fluoro-3-phenoxybenzoylamino)benzoic acid IC50 is 0.0038 mM Enterococcus faecalis
2.3.1.180 2-(4-fluoro-3-phenoxybenzoylamino)benzoic acid methyl ester
-
Enterococcus faecalis
2.3.1.180 2-(4-morpholin-4-yl-3-phenoxybenzoylamino)benzoic acid IC50 is 0.0032 mM Enterococcus faecalis
2.3.1.180 2-fluoro-6-(3-phenoxybenzoylamino)benzoic acid IC50 is 0.006 mM Enterococcus faecalis
2.3.1.180 2-hydroxy-6-(3-phenoxybenzoylamino)benzoic acid IC50 is 0.00041 mM Enterococcus faecalis
2.3.1.180 2-hydroxy-6-[(2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.000004 mM Enterococcus faecalis
2.3.1.180 2-[(2',4'-difluoro-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00016 mM Enterococcus faecalis
2.3.1.180 2-[(2-diethylsulfamoyl-biphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.0016 mM Enterococcus faecalis
2.3.1.180 2-[(2-phenoxy-3'-trifluoromethoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00047 mM Enterococcus faecalis
2.3.1.180 2-[(2-phenoxy-4'-trifluoromethylbiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.000096 mM Enterococcus faecalis
2.3.1.180 2-[(2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.000056 mM Enterococcus faecalis
2.3.1.180 2-[(3',4'-difluoro-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00033 mM Enterococcus faecalis
2.3.1.180 2-[(3'-chloro-4'-fluoro-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00057 mM Enterococcus faecalis
2.3.1.180 2-[(3'-isopropyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00079 mM Enterococcus faecalis
2.3.1.180 2-[(4'-chloro-3'-methyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00025 mM Enterococcus faecalis
2.3.1.180 2-[(4'-ethoxy-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00022 mM Enterococcus faecalis
2.3.1.180 2-[(4'-fluoro-3'-methyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00024 mM Enterococcus faecalis
2.3.1.180 2-[(4'-hydroxy-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00041 mM Enterococcus faecalis
2.3.1.180 2-[(4'-methanesulfonyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.000028 mM Enterococcus faecalis
2.3.1.180 2-[(4'-methyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid IC50 is 0.00016 mM Enterococcus faecalis
2.3.1.180 2-[3-(3-carboxyphenoxy)benzoylamino]benzoic acid IC50 is 0.0037 mM Enterococcus faecalis
2.3.1.180 2-[3-(4-carboxyphenoxy)benzoylamino]benzoic acid IC50 is 0.0044 mM Enterococcus faecalis
2.3.1.180 2-[3-(4-fluorophenoxy)benzoylamino]benzoic acid IC50 is 0.005 mM Enterococcus faecalis
2.3.1.180 2-[3-(pyridin-4-yloxy)benzoylamino]benzoic acid IC50 is 0.010 mM Enterococcus faecalis
2.3.1.180 2-[3-phenoxy-4-(1H-pyrazol-4-yl)benzoylamino]benzoic acid IC50 is 0.022 mM Enterococcus faecalis
2.3.1.180 2-[4-(3,5-dimethylpiperazin-1-yl)-3-phenoxybenzoylamino]benzoic acid IC50 is 0.038 mM Enterococcus faecalis
2.3.1.180 2-[4-(3,5-dimethylpiperidin-1-yl)-3-phenoxybenzoylamino]benzoic acid IC50 is 0.00027 mM Enterococcus faecalis
2.3.1.180 2-[4-(4-methylpiperazin-1-yl)-3-phenoxybenzoylamino]benzoic acid IC50 is 0.025 mM Enterococcus faecalis
2.3.1.180 3-(3-phenoxybenzoylamino)pyridine-2-carboxylic acid IC50 is 0.290 mM Enterococcus faecalis
2.3.1.180 3-(3-phenoxybenzoylamino)thiophene-2-carboxylic acid IC50 is 0.0101 mM Enterococcus faecalis
2.3.1.180 3-diethylsulfamoyl-4-fluorobenzoic acid
-
Enterococcus faecalis
2.3.1.180 3-diethylsulfamoyl-4-methoxybenzoic acid
-
Enterococcus faecalis
2.3.1.180 4'-(2-carboxyphenylcarbamoyl)-2'-phenoxybiphenyl-4-carboxylic acid IC50 is 0.0021 mM Enterococcus faecalis
2.3.1.180 4-bromo-3-diethylsulfamoylbenzoic acid
-
Enterococcus faecalis
2.3.1.180 4-bromo-3-phenoxybenzoic acid
-
Enterococcus faecalis
2.3.1.180 4-fluoro-3-phenoxybenzoic acid
-
Enterococcus faecalis
2.3.1.180 methyl 4-bromo-3-hydroxybenzoate
-
Enterococcus faecalis
2.3.1.180 additional information inhibitor design by computational chemistry, antibacterial potency of inhibitors, overview Enterococcus faecalis
2.3.1.180 pyridin-4-yloxybenzoic acid
-
Enterococcus faecalis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.180 acetyl-CoA + malonyl-[acyl-carrier protein] Enterococcus faecalis the enzyme initiates the fatty acid biosynthesis acetoacetyl-[acyl-carrier protein] + CoA + CO2
-
?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.180 Enterococcus faecalis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.180 acetyl-CoA + malonyl-[acyl-carrier protein]
-
Enterococcus faecalis acetoacetyl-[acyl-carrier protein] + CoA + CO2
-
?
2.3.1.180 acetyl-CoA + malonyl-[acyl-carrier protein] the enzyme initiates the fatty acid biosynthesis Enterococcus faecalis acetoacetyl-[acyl-carrier protein] + CoA + CO2
-
?

Synonyms

EC Number Synonyms Comment Organism
2.3.1.180 beta-ketoacyl-ACP synthase III
-
Enterococcus faecalis
2.3.1.180 beta-ketoacyl-acyl carrier protein synthase III
-
Enterococcus faecalis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.180 7
-
assay at Enterococcus faecalis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.3.1.180 0.000004
-
IC50 is 0.000004 mM Enterococcus faecalis 2-hydroxy-6-[(2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.000028
-
IC50 is 0.000028 mM Enterococcus faecalis 2-[(4'-methanesulfonyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.000056
-
IC50 is 0.000056 mM Enterococcus faecalis 2-[(2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.000062
-
IC50 is 0.000062 mM Enterococcus faecalis 2-(4-bromo-3-phenoxybenzoylamino)-6-hydroxybenzoic acid
2.3.1.180 0.000096
-
IC50 is 0.000096 mM Enterococcus faecalis 2-[(2-phenoxy-4'-trifluoromethylbiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00011
-
IC50 is 0.00011 mM Enterococcus faecalis 2-(3-phenoxy-4-pyridin-3-ylbenzoylamino)benzoic acid
2.3.1.180 0.00016
-
IC50 is 0.00016 mM Enterococcus faecalis 2-[(4'-methyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00016
-
IC50 is 0.00016 mM Enterococcus faecalis 2-[(2',4'-difluoro-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00022
-
IC50 is 0.00022 mM Enterococcus faecalis 2-[(4'-ethoxy-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00024
-
IC50 is 0.00024 mM Enterococcus faecalis 2-[(4'-fluoro-3'-methyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00025
-
IC50 is 0.00025 mM Enterococcus faecalis 2-[(4'-chloro-3'-methyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00027
-
IC50 is 0.00027 mM Enterococcus faecalis 2-[4-(3,5-dimethylpiperidin-1-yl)-3-phenoxybenzoylamino]benzoic acid
2.3.1.180 0.00029
-
IC50 is 0.00029 mM Enterococcus faecalis 2-(3-phenoxy-4-piperidin-1-ylbenzoylamino)benzoic acid
2.3.1.180 0.00033
-
IC50 is 0.00033 mM Enterococcus faecalis 2-[(3',4'-difluoro-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00041
-
IC50 is 0.00041 mM Enterococcus faecalis 2-[(4'-hydroxy-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00041
-
IC50 is 0.00041 mM Enterococcus faecalis 2-hydroxy-6-(3-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.00047
-
IC50 is 0.00047 mM Enterococcus faecalis 2-[(2-phenoxy-3'-trifluoromethoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00057
-
IC50 is 0.00057 mM Enterococcus faecalis 2-[(3'-chloro-4'-fluoro-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.00079
-
IC50 is 0.00079 mM Enterococcus faecalis 2-[(3'-isopropyl-2-phenoxybiphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.0011
-
IC50 is 0.0011 mM Enterococcus faecalis 2-(4-bromo-3-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.0012
-
IC50 is 0.0012 mM Enterococcus faecalis 2-(3-phenoxy-4-thiomorpholin-4-ylbenzoylamino)benzoic acid
2.3.1.180 0.0016
-
IC50 is 0.0016 mM Enterococcus faecalis 2-(4-bromo-3-diethylsulfamoylbenzoylamino)-benzoic acid
2.3.1.180 0.0016
-
IC50 is 0.0016 mM Enterococcus faecalis 2-[(2-diethylsulfamoyl-biphenyl-4-carbonyl)amino]benzoic acid
2.3.1.180 0.0021
-
IC50 is 0.0021 mM Enterococcus faecalis 2-(4-cyclopentylmethoxy-3-diethylsulfamoylbenzoylamino)benzoic acid
2.3.1.180 0.0021
-
IC50 is 0.0021 mM Enterococcus faecalis 4'-(2-carboxyphenylcarbamoyl)-2'-phenoxybiphenyl-4-carboxylic acid
2.3.1.180 0.0022
-
IC50 is 0.0022 mM Enterococcus faecalis 2-(3-diethylsulfamoyl-4-piperidin-1-ylbenzoylamino)benzoic acid
2.3.1.180 0.0027
-
IC50 is 0.0027 mM Enterococcus faecalis 2-(3-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.0032
-
IC50 is 0.0032 mM Enterococcus faecalis 2-(4-morpholin-4-yl-3-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.0037
-
IC50 is 0.0037 mM Enterococcus faecalis 2-[3-(3-carboxyphenoxy)benzoylamino]benzoic acid
2.3.1.180 0.0038
-
IC50 is 0.0038 mM Enterococcus faecalis 2-(4-fluoro-3-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.0044
-
IC50 is 0.0044 mM Enterococcus faecalis 2-[3-(4-carboxyphenoxy)benzoylamino]benzoic acid
2.3.1.180 0.005
-
IC50 is 0.005 mM Enterococcus faecalis 2-[3-(4-fluorophenoxy)benzoylamino]benzoic acid
2.3.1.180 0.006
-
IC50 is 0.006 mM Enterococcus faecalis 2-fluoro-6-(3-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.0061
-
IC50 is 0.0061 mM Enterococcus faecalis 2-(3-diethylsulfamoyl-4-phenoxybenzoylamino)benzoic acid
2.3.1.180 0.0084
-
IC50 is 0.0084 mM Enterococcus faecalis 2-(3-diethylsulfamoyl-4-fluorobenzoylamino)benzoic acid
2.3.1.180 0.01
-
IC50 is 0.010 mM Enterococcus faecalis 2-[3-(pyridin-4-yloxy)benzoylamino]benzoic acid
2.3.1.180 0.0101
-
IC50 is 0.0101 mM Enterococcus faecalis 3-(3-phenoxybenzoylamino)thiophene-2-carboxylic acid
2.3.1.180 0.0114
-
IC50 is 0.0114 mM Enterococcus faecalis 2-(3-diethylsulfamoyl-4-methoxybenzoylamino)benzoic acid
2.3.1.180 0.022
-
IC50 is 0.022 mM Enterococcus faecalis 2-[3-phenoxy-4-(1H-pyrazol-4-yl)benzoylamino]benzoic acid
2.3.1.180 0.025
-
IC50 is 0.025 mM Enterococcus faecalis 2-[4-(4-methylpiperazin-1-yl)-3-phenoxybenzoylamino]benzoic acid
2.3.1.180 0.038
-
IC50 is 0.038 mM Enterococcus faecalis 2-[4-(3,5-dimethylpiperazin-1-yl)-3-phenoxybenzoylamino]benzoic acid
2.3.1.180 0.043
-
IC50 is 0.043 mM Enterococcus faecalis 2-(3-phenoxybenzoylamino)thiophene-3-carboxylic acid
2.3.1.180 0.16
-
IC50 is 0.16 mM Enterococcus faecalis 2-(4-bromo-3-diethylsulfamoyl-5-methylbenzoylamino)-benzoic acid
2.3.1.180 0.185
-
IC50 is 0.185 mM Enterococcus faecalis 2-(3-phenoxy-4-piperazin-1-ylbenzoylamino)benzoic acid
2.3.1.180 0.29
-
IC50 is 0.290 mM Enterococcus faecalis 3-(3-phenoxybenzoylamino)pyridine-2-carboxylic acid
2.3.1.180 1
-
IC50 is above 1.0 mM Enterococcus faecalis 2-(3-phenoxybenzoylamino)nicotinic acid