Any feedback?
Please rate this page
(all_enzymes.php)
(0/150)

BRENDA support

1.3.1.118: meromycolic acid enoyl-[acyl-carrier-protein] reductase

This is an abbreviated version!
For detailed information about meromycolic acid enoyl-[acyl-carrier-protein] reductase, go to the full flat file.

Word Map on EC 1.3.1.118

Reaction

a meromycolyl-[acyl-carrier protein]
+
NAD+
=
a trans-DELTA2-meromycolyl-[acyl-carrier protein]
+
NADH
+
H+

Synonyms

2-trans-enoyl-ACP reductase, 2-trans-enoyl-ACP(CoA) reductase, 2-trans-enoyl-acyl carrier protein reductase, enoyl acyl carrier protein reductase, enoyl acyl carrier protein reductase InhA, enoyl-ACP reductase, enoyl-ACP reductase InhA, enoyl-acyl carrier protein reductase, FAS-II enoyl reductase, FASII enoyl-ACP reductase, InhA, InhA Protein, MtInhA

ECTree

     1 Oxidoreductases
         1.3 Acting on the CH-CH group of donors
             1.3.1 With NAD+ or NADP+ as acceptor
                1.3.1.118 meromycolic acid enoyl-[acyl-carrier-protein] reductase

Inhibitors

Inhibitors on EC 1.3.1.118 - meromycolic acid enoyl-[acyl-carrier-protein] reductase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1H-indol-5-yl)[4-[(4-methylphenyl)(phenyl)methyl]piperazin-1-yl]methanone
0.015 mM, 74% inhibition
(4-(9H-fluoren-9-yl) piperazin-1-yl)-(4-methylbenzyl)-methanone
0.015 mM, 99% inhibition
(4-(9H-fluoren-9-yl)piperazin-1-yl) (2,5-difluorophenyl)methanone
uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (2-fluorophenyl)methanone
uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (3-fluorophenyl)methanone
uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA
(4-(9H-Fluoren-9-yl)piperazin-1-yl) (3-tolyl)methanone
uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (4-chlorophenyl)methanone
uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (4-fluorophenyl)methanone
uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (4-methoxyphenyl)methanone
uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (4-tolyl)methanone
uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl) (phenyl)methanone
uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA
(4-(9H-fluoren-9-yl)piperazin-1-yl)(indolin-5-yl)methanone
i.e. Genz10850
(4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(1H-indole-5-carbonyl)-methanone
0.015 mM, 84% inhibition
(4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-(4-methylbenzyl)-methanone
0.015 mM, 83% inhibition
(4-(bis(4-fluorophenyl)methyl)piperazin-1-yl)-benzyl-methanone
0.015 mM, 81% inhibition
(4-benzylpiperidin-1-yl)(4-methylphenyl)methanone
-
(4-benzylpiperidin-1-yl)(p-tolyl)methanone
-
(4-methylphenyl)[4-[(4-methylphenyl)(phenyl)methyl]piperazin-1-yl]methanone
0.015 mM, 77% inhibition
1-(2-furoyl)-4-[3-(2-ethylphenoxy)benzyl]piperazine
-
39.5% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-(2-methylphenoxy)benzyl]piperazine
-
41.2% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-(phenoxy)benzyl]piperazine
-
KES4, potent inhibitor, 68% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-[2-(sec-butyl)phenoxy]benzyl]piperazine
-
48.8% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-[2-(tert-butyl)phenoxy]benzyl]piperazine
-
66.5% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-[3-(tert-butyl)phenoxy]benzyl]piperazine
-
63.9% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-[3-(trifluoromethyl)phenoxy]benzyl]piperazine
-
45.4% residual activity at 0.05 mM
-
1-(2-furoyl)-4-[3-[4-(methoxycarbonylmethyl)phenoxy]benzyl]piperazine
-
83.4% residual activity at 0.05 mM
-
1-cyclohexyl-N-(2,5-dimethylphenyl)-5-oxopyrrolidine-3-carboxamide
-
1-cyclohexyl-N-(3,5-dichlorophenyl)-5-oxopyrrolidine-3-carboxamide
-
1-cyclohexyl-N-(5'-hydroxy-[1,1':4',1''-terphenyl]-2'-yl)-5-oxopyrrolidine-3-carboxamide
-
2-(2-bromophenoxy)-5-hexylphenol
-
2-(2-chloro-4-fluorophenyl)-N-(4-((3,5-dimethyl-1H-pyrazol-1-yl)-methyl)phenyl)acetamide
-
2-(2-chlorophenoxy)-5-hexylphenol
-
2-(2-chlorophenoxy)-5-[(4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl]phenol
-
2-(2-fluorophenoxy)-5-hexylphenol
-
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
2-(2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
2-(2-methylphenoxy)-5-[[4-(3-methylphenyl)-1H-1,2,3-triazol-1-yl]methyl]phenol
-
2-(4-hexyl-2-hydroxyphenoxy)benzonitrile
-
2-(4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
2-(4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
2-(4-[[4-(2-bromoethyl)-1H-1,2,3-triazol-1-yl]methyl]-2-hydroxyphenoxy)benzonitrile
-
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(2-chloro-5-(trifluoromethyl)phenyl)acetamide
-
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(5-nitrothiazol-2-yl)acetamide
-
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(6-nitrobenzo[d]thiazol-2-yl)acetamide
-
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(furan-2-ylmethyl)acetamide
-
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-(thiophen-2-ylmethyl)acetamide
-
2-(6-chloro-4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide
-
2-(ethanesulfonyl)-6-[2-[(E)-(hydroxyimino)methyl]-4-(trifluoromethyl)phenoxy]-2,3,1-benzodiazaborinin-1(2H)-ol
-
2-(ethanesulfonyl)-7-[2-[(Z)-(hydroxyimino)methyl]-4-(trifluoromethyl)phenoxy]-2,3,1-benzodiazaborinin-1(2H)-ol
diazaborine, in vitro bactericidal activity against replicating bacteria active against several drug-resistant clinical isolates. AN12855 binds to and inhibits the substrate-binding site of InhA in a cofactor-independent manner. It shows good drug exposure after i.v. and oral delivery, with 53% oral bioavailability. Delivered orally, AN12855 exhibits dose-dependent efficacy in both an acute and chronic murine model of tuberculosis infection. AN12855 is a promising candidate for the development of new antitubercular agents
2-(o-tolyloxy)-5-hexylphenol
i.e. PT70, slow, tight binding inhibitor. It binds preferentially to the enzyme/NAD+x01complex and has a residence time of 24 min on the target, which is 14000 times longer than that of the rapid reversible inhibitor from which it is derived. The 1.8 A crystal structure of the ternary complex between InhA, NAD+, and PT70 reveals the molecular details of enzyme inhibitor recognition and supports the hypothesis that slow onset inhibition is coupled to ordering of an active site loop, which leads to the closure of the substrate-binding pocket
2-hexadecynoyl-CoA
-
-
2-octadecynoyl-CoA
-
-
2-[2-hydroxy-4-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]phenoxy]benzonitrile
-
2-[4-[(4-cyclohexyl-1H-1,2,3-triazol-1-yl)methyl]-2-hydroxyphenoxy]benzonitrile
-
2-[4-[(4-cyclopentyl-1H-1,2,3-triazol-1-yl)methyl]-2-hydroxyphenoxy]benzonitrile
-
2-[4-[(4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl]-2-hydroxyphenoxy]benzonitrile
-
2-[4-[(4-ethyl-1H-1,2,3-triazol-1-yl)methyl]-2-hydroxyphenoxy]benzonitrile
-
4-(trifluoromethyl)-2-(4,5-dihydro-4-(2,4-dinitrophenyl)pyrazol-1-yl)pyrimidine
i.e. Genz8575
4-[[1-hydroxy-2-(methanesulfonyl)-1,2-dihydro-2,3,1-benzodiazaborinin-7-yl]oxy]benzonitrile
-
5-butyl-2-phenoxyphenol
-
5-ethyl-2-phenoxyphenol
-
5-hexyl-2-(2-methylphenoxy)phenol
-
5-hexyl-2-phenoxyphenol
-
5-octyl-2-phenoxyphenol
-
5-pentyl-2-phenoxyphenol
-
5-tetradecyl-2-phenoxyphenol
-
5-[(4-cyclopropyl-1H-1,2,3-triazol-1-yl)methyl]-2-(2-methylphenoxy)phenol
-
5-[(4-ethyl-1H-1,2,3-triazol-1-yl)methyl]-2-(2-methylphenoxy)phenol
-
5-[2-[(E)-(hydroxyimino)methyl]phenoxy]-2,1-benzoxaborol-1(3H)-ol
-
5-[[4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl]methyl]-2-(2-methylphenoxy)phenol
-
6-[4-(trifluoromethyl)phenoxy]-2,1-benzoxaborol-1(3H)-ol
-
7-[2-[(Z)-(hydroxyimino)methyl]-4-(trifluoromethyl)phenoxy]-2-(methanesulfonyl)-2,3,1-benzodiazaborinin-1(2H)-ol
-
9H-fluoren-9-yl-piperazine
-
-
-
Ethionamide
isoniazid
isoniazid-coenzyme adduct
-
inhibition by several types of isoniazid-coenzyme adducts coexisting in solution is discussed in relation with the structure of the coenzyme, the stereochemistry of the adducts, and their existence as both open and cyclic forms
-
isoniazid-NADP
competitive
N-((4-bromo-1-ethyl-1H-pyrazol-5-yl)methyl)-4-((3,5-dimethyl-1Hpyrazol-1-yl)methyl)benzamide
-
N-(2,3-dichlorophenyl)-4-(1H-pyrrol-1-yl)benzamide
anti-tuberculosis activity
N-(2-aminophenyl)-4-(1H-pyrrol-1-yl)benzamide
anti-tuberculosis activity
N-(2-bromobenzyl)-4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]benzamide
-
N-(2-chloro-4-fluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(2-chloro-4-fluorobenzyl)-4-((4-methylthiazol-2-yl)methyl)-benzamide
-
N-(2-chloro-5-(2-phenylacetamido)benzyl)-4-((3,5-dimethyl-1Hpyrazol-1-yl)methyl)benzamide
-
N-(2-chloro-5-(3-phenylureido)benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(2-chloro-5-(trifluoromethyl)phenyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(2-chloro-5-aminobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(2-chlorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(2-nitrobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(2-nitrophenyl)-4-(1H-pyrrol-1-yl)benzamide
anti-tuberculosis activity
N-(2-trifluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)-benzamide
-
N-(3-bromobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(3-chlorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(3-fluorophenyl)-4-(1H-pyrrol-1-yl)benzamide
anti-tuberculosis activity
N-(3-methanesulfonybenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)-methyl)benzamide
-
N-(3-propan-2-yloxybenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(4-chlorophenyl)-4-(1H-pyrrol-1-yl)benzamide
anti-tuberculosis activity
N-(4-fluoro-2-(trifluoromethyl)benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(4-fluorobenzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(5-nitrothiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(6-nitrobenzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(benzo[d]thiazol-2-yl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(benzo[d]thiazol-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(benzo[d]thiazol-2-yl)-2-(6-chloro-2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(benzyl)-4-((3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzamide
-
N-(furan-2-yl-methyl)-2-(4-oxoquinazolin-3(4H)-yl)acetamide
-
N-(furan-2-ylmethyl)-2-(2-methyl-4-oxoquinazolin-3(4H)-yl)acetamide
-
N-([1,1'-biphenyl]-4-yl)-1-cyclohexyl-5-oxopyrrolidine-3-carboxamide
-
N-[(1-[[3-hydroxy-4-(2-methylphenoxy)phenyl]methyl]-1H-1,2,3-triazol-4-yl)methyl]cyclopropanecarboxamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(2-methyl-1,3-thiazol-4-yl)methyl]benzamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(3-methyl-1H-pyrazol-1-yl)methyl]benzamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)-oxy]benzamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)methyl]benzamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(6-methylpyridin-2-yl)sulfanyl]benzamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[(dimethyl-1,3-thiazol-2-yl)methyl]benzamide
-
N-[(2-chloro-4-fluorophenyl)methyl]-4-[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]benzamide
-
N-[(4-fluorophenyl)methyl]-4-[[2-methyl-5-(2,2,2-trifluoroethyl)furan-3-yl]methyl]benzamide
-
NAD+
linear competitive inhibitor versus NADH
pentacyano(isoniazid)ferrate(II)
the inorganic complex inhibits both wild-type and isoniazid-resistant Ile21Val mutants of InhA and this inactivation did not require activation by KatG. Molecular dynamics simulations show that the interaction of pentacyano(isoniazid)ferrate(II) with InhA leads to macromolecular instabilities reflected in the long time necessary for simulation convergence. These instabilities are mainly due to perturbation of the substrate binding loop, particularly the partial denaturation of helices alpha6 and alpha7
prothionamide
the prodrug requires activation by EthA, a flavin-dependent monooxygenase. According to the crystal structure of InhA with bound prothionamide-NAD adduct, the propyl-isonicotinic-acyl moiety is located in a hydrophobic pocket formed by the rearrangement of the side chain of Phe149, and an aromatic ringstacking interaction with the pyridine ring
triclosan
Trp-Tyr-Trp
structure-based computer modelling approach to design a tripeptide inhibitor. Docking studies indicate that the designed peptide has potency 100 times higher than the best known inhibitor. The results suggest that the designed inhibitor is a suitable lead compound for the development of novel anti-TB drugs
[4-(9H-fluoren-9-yl) piperazin-1-yl]-benzyl-methanone
0.015 mM, 97% inhibition
[4-(9H-fluoren-9-yl)piperazin-1-yl](1H-indol-5-yl)methanone
0.015 mM, 94% inhibition
[4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl](1H-indol-5-yl)methanone
0.015 mM, 67% inhibition
[4-[(4-chlorophenyl)(phenyl)methyl]piperazin-1-yl](4-methylphenyl)methanone
0.015 mM, 74% inhibition
[4-[(4-fluorophenyl)(phenyl)methyl]piperazin-1-yl](1H-indol-5-yl)methanone
0.015 mM, 81% inhibition
[4-[(4-fluorophenyl)(phenyl)methyl]piperazin-1-yl](phenyl)methanone
0.015 mM, 81% inhibition
additional information
-