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Literature summary for 1.3.1.9 extracted from

  • Guardia, A.; Gulten, G.; Fernandez, R.; Gomez, J.; Wang, F.; Convery, M.; Blanco, D.; Martinez, M.; Perez-Herran, E.; Alonso, M.; Ortega, F.; Rullas, J.; Calvo, D.; Mata, L.; Young, R.; Sacchettini, J.; Mendoza-Losana, A.; Remuinan, M.
    N-Benzyl-4-((heteroaryl)methyl)benzamides a new class of direct NADH-dependent 2-trans enoyl-acyl carrier protein reductase (InhA) inhibitors with antitubercular activity (2016), ChemMedChem, 11, 687-701 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli (BL21) Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
2-(2-chloro-4-fluorophenyl)-N-(4-((3,5-dimethyl-1H-pyrazol-1-yl)-methyl)phenyl)acetamide
-
Mycobacterium tuberculosis
N-((4-bromo-1-ethyl-1H-pyrazol-5-yl)methyl)-4-((3,5-dimethyl-1Hpyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-bromobenzyl)-4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]benzamide
-
Mycobacterium tuberculosis
N-(2-chloro-4-fluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-chloro-4-fluorobenzyl)-4-((4-methylthiazol-2-yl)methyl)-benzamide
-
Mycobacterium tuberculosis
N-(2-chloro-5-(2-phenylacetamido)benzyl)-4-((3,5-dimethyl-1Hpyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-chloro-5-(3-phenylureido)benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-chloro-5-aminobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-chlorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-nitrobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(2-trifluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-benzamide
-
Mycobacterium tuberculosis
N-(3-bromobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(3-chlorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(3-methanesulfonybenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)-methyl)benzamide
-
Mycobacterium tuberculosis
N-(3-propan-2-yloxybenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(4-fluoro-2-(trifluoromethyl)benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(4-fluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-(benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(2-methyl-1,3-thiazol-4-yl)methyl]benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(3-methyl-1H-pyrazol-1-yl)methyl]benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)-oxy]benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)methyl]benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)sulfanyl]benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(dimethyl-1,3-thiazol-2-yl)methyl]benzamide
-
Mycobacterium tuberculosis
N-[(2-chloro-4-fluorophenyl)methyl]-4-[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]benzamide
-
Mycobacterium tuberculosis
N-[(4-fluorophenyl)methyl]-4-[[2-methyl-5-(2,2,2-trifluoroethyl)furan-3-yl]methyl]benzamide
-
Mycobacterium tuberculosis

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WGR1
-
-
Mycobacterium tuberculosis ATCC 25618 P9WGR1
-
-

Purification (Commentary)

Purification (Comment) Organism
-
Mycobacterium tuberculosis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
trans-2-dodecenoyl-CoA + NADH + H+
-
Mycobacterium tuberculosis dodecanoyl-CoA + NAD+
-
?
trans-2-dodecenoyl-CoA + NADH + H+
-
Mycobacterium tuberculosis ATCC 25618 dodecanoyl-CoA + NAD+
-
?

Synonyms

Synonyms Comment Organism
InhA
-
Mycobacterium tuberculosis

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Mycobacterium tuberculosis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.8
-
assay at Mycobacterium tuberculosis

Cofactor

Cofactor Comment Organism Structure
NADH
-
Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00004
-
pH 6.8, 25°C Mycobacterium tuberculosis 2-(2-chloro-4-fluorophenyl)-N-(4-((3,5-dimethyl-1H-pyrazol-1-yl)-methyl)phenyl)acetamide
0.00005
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)methyl]benzamide
0.00006
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)sulfanyl]benzamide
0.00006
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-4-fluorobenzyl)-4-((4-methylthiazol-2-yl)methyl)-benzamide
0.00008
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(2-phenylacetamido)benzyl)-4-((3,5-dimethyl-1Hpyrazol-1-yl)methyl)benzamide
0.00009
-
pH 6.8, 25°C Mycobacterium tuberculosis N-((4-bromo-1-ethyl-1H-pyrazol-5-yl)methyl)-4-((3,5-dimethyl-1Hpyrazol-1-yl)methyl)benzamide
0.00009
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-(3-phenylureido)benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.00009
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(2-methyl-1,3-thiazol-4-yl)methyl]benzamide
0.00012
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(4-fluorophenyl)methyl]-4-[[2-methyl-5-(2,2,2-trifluoroethyl)furan-3-yl]methyl]benzamide
0.00025
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(4-fluorophenyl)methyl]-4-[[2-methyl-5-(2,2,2-trifluoroethyl)furan-3-yl]methyl]benzamide
0.00025
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(2-methyl-1,3-thiazol-4-yl)methyl]benzamide
0.00032
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]benzamide
0.00035
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-5-aminobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.0005
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chloro-4-fluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.0005
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(3-methyl-1H-pyrazol-1-yl)methyl]benzamide
0.00054
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-bromobenzyl)-4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]benzamide
0.001
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-trifluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-benzamide
0.00126
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-chlorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.0014
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(dimethyl-1,3-thiazol-2-yl)methyl]benzamide
0.00158
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(3-propan-2-yloxybenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.00158
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(3-bromobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.00158
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(3-chlorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.00251
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(2-nitrobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.00251
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(3-methanesulfonybenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)-methyl)benzamide
0.0031
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(4-fluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
0.00325
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(2-methyl-1,3-thiazol-4-yl)methyl]benzamide
0.0034
-
pH 6.8, 25°C Mycobacterium tuberculosis N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)-oxy]benzamide
0.00593
-
pH 6.8, 25°C Mycobacterium tuberculosis N-(benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide