Literature summary for 2.3.1.180 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.

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Application

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

Crystallization (Commentary)

Crystallization (Comment)	Organism
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

Crystallization (Comment)

Organism

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

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism	UniProt	Comment	Textmining
Enterococcus faecalis	-	-	-

Substrates and Products (Substrate)

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

Synonyms

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

pH Optimum

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

IC50 Value

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