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Literature summary extracted from

  • He, X.; Alian, A.; Ortiz de Montellano, P.
    Inhibition of the Mycobacterium tuberculosis enoyl acyl carrier protein reductase InhA by arylamides (2007), Bioorg. Med. Chem., 15, 6649-6658 .
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.3.1.9 the crystal structure of the enzyme in complex with the inhibitor N-(4-methylbenzoyl)-4-benzylpiperidine reveals the binding mode of the inhibitor within the active site Mycobacterium tuberculosis
1.3.1.118 the crystal structure of the enzyme in complex with the inhibitor N-(4-methylbenzoyl)-4-benzylpiperidine reveals the binding mode of the inhibitor within the active site Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.1.9 (1H-indol-5-yl)[4-[(4-methylphenyl)(phenyl)methyl]piperazin-1-yl]methanone 0.015 mM, 74% inhibition Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl) piperazin-1-yl)-(4-methylbenzyl)-methanone 0.015 mM, 99% inhibition Mycobacterium tuberculosis
1.3.1.9 (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(1H-indole-5-carbonyl)-methanone 0.015 mM, 84% inhibition Mycobacterium tuberculosis
1.3.1.9 (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(4-methylbenzyl)-methanone 0.015 mM, 83% inhibition Mycobacterium tuberculosis
1.3.1.9 (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-benzyl-methanone 0.015 mM, 81% inhibition Mycobacterium tuberculosis
1.3.1.9 (4-methylphenyl)[4-[(4-methylphenyl)(phenyl)methyl]piperazin-1-yl]methanone 0.015 mM, 77% inhibition Mycobacterium tuberculosis
1.3.1.9 [4-(9H-fluoren-9-yl) piperazin-1-yl]-benzyl-methanone 0.015 mM, 97% inhibition Mycobacterium tuberculosis
1.3.1.9 [4-(9H-fluoren-9-yl)piperazin-1-yl](1H-indol-5-yl)methanone 0.015 mM, 94% inhibition Mycobacterium tuberculosis
1.3.1.9 [4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl](1H-indol-5-yl)methanone 0.015 mM, 67% inhibition Mycobacterium tuberculosis
1.3.1.9 [4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl](4-methylphenyl)methanone 0.015 mM, 74% inhibition Mycobacterium tuberculosis
1.3.1.9 [4-[(4-fluorophenyl)(phenyl)methyl]piperazin-1-yl](1H-indol-5-yl)methanone 0.015 mM, 81% inhibition Mycobacterium tuberculosis
1.3.1.9 [4-[(4-fluorophenyl)(phenyl)methyl]piperazin-1-yl](phenyl)methanone 0.015 mM, 81% inhibition Mycobacterium tuberculosis
1.3.1.118 (1H-indol-5-yl)[4-[(4-methylphenyl)(phenyl)methyl]piperazin-1-yl]methanone 0.015 mM, 74% inhibition Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl) piperazin-1-yl)-(4-methylbenzyl)-methanone 0.015 mM, 99% inhibition Mycobacterium tuberculosis
1.3.1.118 (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(1H-indole-5-carbonyl)-methanone 0.015 mM, 84% inhibition Mycobacterium tuberculosis
1.3.1.118 (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(4-methylbenzyl)-methanone 0.015 mM, 83% inhibition Mycobacterium tuberculosis
1.3.1.118 (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-benzyl-methanone 0.015 mM, 81% inhibition Mycobacterium tuberculosis
1.3.1.118 (4-methylphenyl)[4-[(4-methylphenyl)(phenyl)methyl]piperazin-1-yl]methanone 0.015 mM, 77% inhibition Mycobacterium tuberculosis
1.3.1.118 [4-(9H-fluoren-9-yl) piperazin-1-yl]-benzyl-methanone 0.015 mM, 97% inhibition Mycobacterium tuberculosis
1.3.1.118 [4-(9H-fluoren-9-yl)piperazin-1-yl](1H-indol-5-yl)methanone 0.015 mM, 94% inhibition Mycobacterium tuberculosis
1.3.1.118 [4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl](1H-indol-5-yl)methanone 0.015 mM, 67% inhibition Mycobacterium tuberculosis
1.3.1.118 [4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl](4-methylphenyl)methanone 0.015 mM, 74% inhibition Mycobacterium tuberculosis
1.3.1.118 [4-[(4-fluorophenyl)(phenyl)methyl]piperazin-1-yl](1H-indol-5-yl)methanone 0.015 mM, 81% inhibition Mycobacterium tuberculosis
1.3.1.118 [4-[(4-fluorophenyl)(phenyl)methyl]piperazin-1-yl](phenyl)methanone 0.015 mM, 81% inhibition Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.9 Mycobacterium tuberculosis P9WGR1
-
-
1.3.1.9 Mycobacterium tuberculosis ATCC 25618 P9WGR1
-
-
1.3.1.118 Mycobacterium tuberculosis P9WGR1 cf. EC 1.3.1.9
-
1.3.1.118 Mycobacterium tuberculosis ATCC 25618 P9WGR1 cf. EC 1.3.1.9
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.9 trans-2-octenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis octanoyl-CoA + NAD+
-
 ?
1.3.1.9 trans-2-octenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis ATCC 25618 octanoyl-CoA + NAD+
-
 ?
1.3.1.118 trans-2-octenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis octanoyl-CoA + NAD+
-
 ?
1.3.1.118 trans-2-octenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis ATCC 25618 octanoyl-CoA + NAD+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.1.9 enoyl acyl carrier protein reductase InhA
-
 Mycobacterium tuberculosis
1.3.1.118 enoyl acyl carrier protein reductase InhA
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.3.1.9 0.00009
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis [4-(9H-fluoren-9-yl) piperazin-1-yl]-benzyl-methanone
1.3.1.9 0.0002
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis [4-(9H-fluoren-9-yl)piperazin-1-yl](1H-indol-5-yl)methanone
1.3.1.9 0.0004
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(9H-fluoren-9-yl) piperazin-1-yl)-(4-methylbenzyl)-methanone
1.3.1.9 0.00104
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(1H-indole-5-carbonyl)-methanone
1.3.1.9 0.00189
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(4-methylbenzyl)-methanone
1.3.1.9 0.00204
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-benzyl-methanone
1.3.1.118 0.00009
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis [4-(9H-fluoren-9-yl) piperazin-1-yl]-benzyl-methanone
1.3.1.118 0.0002
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis [4-(9H-fluoren-9-yl)piperazin-1-yl](1H-indol-5-yl)methanone
1.3.1.118 0.0004
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(9H-fluoren-9-yl) piperazin-1-yl)-(4-methylbenzyl)-methanone
1.3.1.118 0.00104
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(1H-indole-5-carbonyl)-methanone
1.3.1.118 0.00189
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(4-methylbenzyl)-methanone
1.3.1.118 0.00204
-
 23°C, pH not specified in the publication Mycobacterium tuberculosis (4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-benzyl-methanone

General Information

EC Number General Information Comment Organism
1.3.1.9 metabolism the enzyme is involved in the type II fatty acid biosynthesis pathway of Mycobacterium tuberculosis Mycobacterium tuberculosis
1.3.1.118 metabolism the enzyme is involved in the type II fatty acid biosynthesis pathway of Mycobacterium tuberculosis Mycobacterium tuberculosis