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Literature summary for 1.3.1.9 extracted from

  • Kitagawa, H.; Kumura, K.; Takahata, S.; Iida, M.; Atsumi, K.
    4-Pyridone derivatives as new inhibitors of bacterial enoyl-ACP reductase FabI (2007), Bioorg. Med. Chem., 15, 1106-1116.
    View publication on PubMed
Search for more literature for 1.3.1.9

Application

Application Comment Organism
medicine antibacterial target Staphylococcus aureus
medicine antibacterial target Escherichia coli

Cloned(Commentary)

Cloned (Comment) Organism
fabI gene from Escherichia coli DH5alpha was cloned into pBAD/Myc-His B vector for expression of the protein in Escherichia coli TOP10 cells Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(E)-1-benzyl-2-methyl-3-[2-(pyridin-3-yl)vinyl]-4-pyridone IC50: higher than 0.100 mM Escherichia coli
1,3-bis(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.0084 mM Escherichia coli
1,3-bis(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 32 Staphylococcus aureus
1,3-dibenzyl-2-methyl-4-pyridone IC50: 0.020 mM Escherichia coli
1,3-dibenzyl-2-methyl-4-pyridone MIC (microg/mL): 64 Staphylococcus aureus
1-(4-aminobenzyl)-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00029 mM Escherichia coli
1-(4-aminobenzyl)-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 1 Staphylococcus aureus
1-benzyl-2-butyl-3-(2,6-dichlorobenzyl)-4-pyridone IC50: 0.0045 mM Escherichia coli
1-benzyl-2-butyl-3-(2,6-dichlorobenzyl)-4-pyridone MIC (microg/ml): 32 Staphylococcus aureus
1-benzyl-2-methyl-3-(2,4,6-trichlorobenzyl)-4-pyridone IC50: 0.0015 mM Escherichia coli
1-benzyl-2-methyl-3-(2,4,6-trichlorobenzyl)-4-pyridone MIC (microg/ml): 8 Staphylococcus aureus
1-benzyl-2-methyl-3-phenyl-4-pyridone IC50: 0.0029 mM Escherichia coli
1-benzyl-2-methyl-3-vinyl-4-pyridone IC50: higher than 0.100 mM Escherichia coli
1-benzyl-2-methyl-3-[2-(pyridin-3-yl)ethyl]-4-pyridone IC50: higher than 0.100 mM Escherichia coli
1-benzyl-3-(2,4-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.0020 mM Escherichia coli
1-benzyl-3-(2,4-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 32 Staphylococcus aureus
1-benzyl-3-(2,6-dichlorobenzyl)-2-ethyl-4-pyridone IC50: 0.00078 mM Escherichia coli
1-benzyl-3-(2,6-dichlorobenzyl)-2-ethyl-4-pyridone MIC (microg/ml): 8 Staphylococcus aureus
1-benzyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00030 mM Escherichia coli
1-benzyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 0.5 Staphylococcus aureus
1-benzyl-3-(2,6-difluorobenzyl)-2-methyl-4-pyridone IC50: 0.0027 mM Escherichia coli
1-benzyl-3-(2,6-difluorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 4 Staphylococcus aureus
1-benzyl-3-(2,6-dimethylbenzyl)-2-methyl-4-pyridone IC50: 0.0043 mM Escherichia coli
1-benzyl-3-(2,6-dimethylbenzyl)-2-methyl-4-pyridone MIC (microg/ml): 16 Staphylococcus aureus
1-benzyl-3-(2-chloro-6-fluorobenzyl)-2-methyl-4-pyridone IC50: 0.00039 mM Escherichia coli
1-benzyl-3-(2-chloro-6-fluorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 2 Staphylococcus aureus
1-benzyl-3-(2-chlorobenzyl)-2-methyl-4-pyridone IC50: 0.0042 mM Escherichia coli
1-benzyl-3-(2-chlorobenzyl)-2-methyl-4-pyridone MIC (microg/mL): 64 Staphylococcus aureus
1-benzyl-3-butyl-2-methyl-4-pyridone IC50: 0.061 mM Escherichia coli
1-benzyl-3-butyl-2-methyl-4-pyridone MIC (microg/ml): higher than 128 Staphylococcus aureus
1-butyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00031 mM Escherichia coli
1-butyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 2 Staphylococcus aureus
1-cyclohexylmethyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00022 mM Escherichia coli
1-cyclohexylmethyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 0.25 Staphylococcus aureus
1-decyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00022 mM Escherichia coli
1-decyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 32 Staphylococcus aureus
3-(2,6-dichlorobenzyl)-1,2-dimethyl-4-pyridone IC50: 0.011 mM Escherichia coli
3-(2,6-dichlorobenzyl)-1,2-dimethyl-4-pyridone MIC (microg/ml): higher than 128 Staphylococcus aureus
3-(2,6-dichlorobenzyl)-1-(4-nitrobenzyl)-2-methyl-4-pyridone IC50: 0.0018 mM Escherichia coli
3-(2,6-dichlorobenzyl)-1-(4-nitrobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 16 Staphylococcus aureus
3-(2,6-dichlorobenzyl)-1-(5-hydroxypentyl)-2-methyl-4-pyridone IC50: 0.0018 mM Escherichia coli
3-(2,6-dichlorobenzyl)-1-(5-hydroxypentyl)-2-methyl-4-pyridone MIC (microg/ml): 8 Staphylococcus aureus
3-(2,6-dichlorobenzyl)-1-furfuryl-2-methyl-4-pyridone IC50: 0.00047 mM Escherichia coli
3-(2,6-dichlorobenzyl)-1-furfuryl-2-methyl-4-pyridone MIC (microg/ml): 2 Staphylococcus aureus
3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.120 mM Escherichia coli
3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): higher than 64 Staphylococcus aureus
3-cyclohexylmethyl-1-benzyl-2-methyl-4-pyridone IC50: 0.00040 mM Escherichia coli
3-cyclohexylmethyl-1-benzyl-2-methyl-4-pyridone MIC (microg/ml): 32 Staphylococcus aureus
4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzamide IC50: 0.0025 mM Escherichia coli
4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzamide MIC (microg/ml): 32 Staphylococcus aureus
4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzoic acid IC50: 0.022 mM Escherichia coli
4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzoic acid MIC (microg/ml): higher than 128 Staphylococcus aureus
5-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]pentanoic acid IC50: 0.110 mM Escherichia coli
6-butyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00038 mM Escherichia coli
6-butyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 8 Staphylococcus aureus
6-cyclohexylmethyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone IC50: 0.00029 mM Escherichia coli
6-cyclohexylmethyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone MIC (microg/ml): 2 Staphylococcus aureus
lead compound MIC (microg/mL): 64 Staphylococcus aureus
methyl 4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzoate IC50: 0.00030 mM Escherichia coli
methyl 4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzoate MIC (microg/ml): higher than 128 Staphylococcus aureus
triclosan IC50: 0.00051 mM Escherichia coli
triclosan MIC (microg/ml): 0.125 Staphylococcus aureus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
acyl-[acyl-carrier protein] + NAD+ Staphylococcus aureus
-
 trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?
acyl-[acyl-carrier protein] + NAD+ Escherichia coli
-
 trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Staphylococcus aureus
-
-
-

Purification (Commentary)

Purification (Comment) Organism
using a Ni-NTA agarose column Escherichia coli

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
acyl-[acyl-carrier protein] + NAD+
-
 Staphylococcus aureus trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?
acyl-[acyl-carrier protein] + NAD+
-
 Escherichia coli trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 ?
crotonyl-CoA + NADH + H+ activity assay Escherichia coli butyryl-CoA + NAD+
-
 ?

Synonyms

Synonyms Comment Organism
enoyl-ACP reductase
-
 Staphylococcus aureus
enoyl-ACP reductase
-
 Escherichia coli
enoyl-[acyl-carrier-protein] reductase
-
 Staphylococcus aureus
enoyl-[acyl-carrier-protein] reductase
-
 Escherichia coli
FabI
-
 Staphylococcus aureus
FabI
-
 Escherichia coli

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
20
-
 FabI-inhibitory activity assay at room temperature Escherichia coli
35
-
 antibacterial activity assay Staphylococcus aureus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 FabI-inhibitory activity assay Escherichia coli

Cofactor

Cofactor Comment Organism Structure
NADH
-
 Staphylococcus aureus
NADH
-
 Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00022
-
 IC50: 0.00022 mM Escherichia coli 1-decyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.00022
-
 IC50: 0.00022 mM Escherichia coli 1-cyclohexylmethyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.00029
-
 IC50: 0.00029 mM Escherichia coli 1-(4-aminobenzyl)-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.00029
-
 IC50: 0.00029 mM Escherichia coli 6-cyclohexylmethyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.0003
-
 IC50: 0.00030 mM Escherichia coli 1-benzyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.0003
-
 IC50: 0.00030 mM Escherichia coli methyl 4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzoate
0.00031
-
 IC50: 0.00031 mM Escherichia coli 1-butyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.00038
-
 IC50: 0.00038 mM Escherichia coli 6-butyl-3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.00039
-
 IC50: 0.00039 mM Escherichia coli 1-benzyl-3-(2-chloro-6-fluorobenzyl)-2-methyl-4-pyridone
0.0004
-
 IC50: 0.00040 mM Escherichia coli 3-cyclohexylmethyl-1-benzyl-2-methyl-4-pyridone
0.00047
-
 IC50: 0.00047 mM Escherichia coli 3-(2,6-dichlorobenzyl)-1-furfuryl-2-methyl-4-pyridone
0.00051
-
 IC50: 0.00051 mM Escherichia coli triclosan
0.00078
-
 IC50: 0.00078 mM Escherichia coli 1-benzyl-3-(2,6-dichlorobenzyl)-2-ethyl-4-pyridone
0.0015
-
 IC50: 0.0015 mM Escherichia coli 1-benzyl-2-methyl-3-(2,4,6-trichlorobenzyl)-4-pyridone
0.0018
-
 IC50: 0.0018 mM Escherichia coli 3-(2,6-dichlorobenzyl)-1-(5-hydroxypentyl)-2-methyl-4-pyridone
0.0018
-
 IC50: 0.0018 mM Escherichia coli 3-(2,6-dichlorobenzyl)-1-(4-nitrobenzyl)-2-methyl-4-pyridone
0.002
-
 IC50: 0.0020 mM Escherichia coli 1-benzyl-3-(2,4-dichlorobenzyl)-2-methyl-4-pyridone
0.0025
-
 IC50: 0.0025 mM Escherichia coli 4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzamide
0.0027
-
 IC50: 0.0027 mM Escherichia coli 1-benzyl-3-(2,6-difluorobenzyl)-2-methyl-4-pyridone
0.0029
-
 IC50: 0.0029 mM Escherichia coli 1-benzyl-2-methyl-3-phenyl-4-pyridone
0.0042
-
 IC50: 0.0042 mM Escherichia coli 1-benzyl-3-(2-chlorobenzyl)-2-methyl-4-pyridone
0.0043
-
 IC50: 0.0043 mM Escherichia coli 1-benzyl-3-(2,6-dimethylbenzyl)-2-methyl-4-pyridone
0.0045
-
 IC50: 0.0045 mM Escherichia coli 1-benzyl-2-butyl-3-(2,6-dichlorobenzyl)-4-pyridone
0.0084
-
 IC50: 0.0084 mM Escherichia coli 1,3-bis(2,6-dichlorobenzyl)-2-methyl-4-pyridone
0.011
-
 IC50: 0.011 mM Escherichia coli 3-(2,6-dichlorobenzyl)-1,2-dimethyl-4-pyridone
0.02
-
 IC50: 0.020 mM Escherichia coli 1,3-dibenzyl-2-methyl-4-pyridone
0.022
-
 IC50: 0.022 mM Escherichia coli 4-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]methylbenzoic acid
0.061
-
 IC50: 0.061 mM Escherichia coli 1-benzyl-3-butyl-2-methyl-4-pyridone
0.1
-
 IC50: higher than 0.100 mM Escherichia coli (E)-1-benzyl-2-methyl-3-[2-(pyridin-3-yl)vinyl]-4-pyridone
0.1
-
 IC50: higher than 0.100 mM Escherichia coli 1-benzyl-2-methyl-3-[2-(pyridin-3-yl)ethyl]-4-pyridone
0.1
-
 IC50: higher than 0.100 mM Escherichia coli 1-benzyl-2-methyl-3-vinyl-4-pyridone
0.11
-
 IC50: 0.110 mM Escherichia coli 5-[3-(2,6-dichlorobenzyl)-2-methyl-4-pyridon-1-yl]pentanoic acid
0.12
-
 IC50: 0.120 mM Escherichia coli 3-(2,6-dichlorobenzyl)-2-methyl-4-pyridone