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Literature summary extracted from

  • Rotta, M.; Pissinate, K.; Villela, A.; Back, D.; Timmers, L.; Bachega, J.; De Souza, O.; Santos, D.; Basso, L.; Machado, P.
    Piperazine derivatives Synthesis, inhibition of the Mycobacterium tuberculosis enoyl-acyl carrier protein reductase and SAR studies (2015), Eur. J. Med. Chem., 90, 436-447 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (2,5-difluorophenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (2-fluorophenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (3-fluorophenyl)methanone uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-Fluoren-9-yl)piperazin-1-yl) (3-tolyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-chlorophenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-fluorophenyl)methanone uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-methoxyphenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-tolyl)methanone uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 (4-(9H-fluoren-9-yl)piperazin-1-yl) (phenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.9 additional information a series of piperazine derivatives is synthesized and screened as MtInhA inhibitors, which results in the identification of compounds with IC50 values in the submicromolar range Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (2,5-difluorophenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (2-fluorophenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (3-fluorophenyl)methanone uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-Fluoren-9-yl)piperazin-1-yl) (3-tolyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-chlorophenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-fluorophenyl)methanone uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-methoxyphenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-tolyl)methanone uncompetitive versus NADH, competitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 (4-(9H-fluoren-9-yl)piperazin-1-yl) (phenyl)methanone uncompetitive versus NADH, noncompetitive versus trans-2-dodecenoyl-CoA Mycobacterium tuberculosis
1.3.1.118 additional information a series of piperazine derivatives is synthesized and screened as MtInhA inhibitors, which results in the identification of compounds with IC50 values in the submicromolar range 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
-
-
1.3.1.118 Mycobacterium tuberculosis ATCC 25618 P9WGR1
-
-

Substrates and Products (Substrate)

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

Synonyms

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

Cofactor

EC Number Cofactor Comment Organism Structure
1.3.1.9 NADH
-
 Mycobacterium tuberculosis
1.3.1.118 NADH
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.3.1.9 0.000183
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (phenyl)methanone
1.3.1.9 0.000222
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-tolyl)methanone
1.3.1.9 0.00024
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (3-fluorophenyl)methanone
1.3.1.9 0.00025
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-Fluoren-9-yl)piperazin-1-yl) (3-tolyl)methanone
1.3.1.9 0.000361
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (2-fluorophenyl)methanone
1.3.1.9 0.000397
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-fluorophenyl)methanone
1.3.1.9 0.00157
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (2,5-difluorophenyl)methanone
1.3.1.9 0.00169
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-chlorophenyl)methanone
1.3.1.9 0.0029
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-methoxyphenyl)methanone
1.3.1.118 0.000183
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (phenyl)methanone
1.3.1.118 0.000222
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-tolyl)methanone
1.3.1.118 0.00024
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (3-fluorophenyl)methanone
1.3.1.118 0.00025
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-Fluoren-9-yl)piperazin-1-yl) (3-tolyl)methanone
1.3.1.118 0.000361
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (2-fluorophenyl)methanone
1.3.1.118 0.000397
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-fluorophenyl)methanone
1.3.1.118 0.00157
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (2,5-difluorophenyl)methanone
1.3.1.118 0.00169
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-chlorophenyl)methanone
1.3.1.118 0.0029
-
 pH 7.0, 25°C Mycobacterium tuberculosis (4-(9H-fluoren-9-yl)piperazin-1-yl) (4-methoxyphenyl)methanone

General Information

EC Number General Information Comment Organism
1.3.1.9 metabolism the enzyme is a member of the mycobacterial type II dissociated fatty acid biosynthesis system Mycobacterium tuberculosis
1.3.1.118 metabolism the enzyme is a member of the mycobacterial type II dissociated fatty acid biosynthesis system Mycobacterium tuberculosis