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Literature summary extracted from

  • Van Poecke, S.; Munier-Lehmann, H.; Helynck, O.; Froeyen, M.; Van Calenbergh, S.
    Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase (2011), Bioorg. Med. Chem., 19, 7603-7611.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.7.4.9 1-(((2R,3S,5S)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)methyl)-3-(((2S,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)methyl)urea
-
 Mycobacterium tuberculosis
2.7.4.9 2',5'-dideoxy-5'-(4-phenyl-1H-1,2,3-triazol-1-yl)-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 2',5'-dideoxy-5'-([[3-(trifluoromethyl)phenyl]carbamoyl]amino)-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 3',5'-diazido-2',3',5'-trideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 3'-(4-chlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-4-thio-beta-D-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 3'-(4-chlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-alpha-D-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 3'-azido-3'-deoxy-4-thio-beta-D-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 3'-azido-3'-deoxy-alpha-D-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 3'-[([[4-chloro-3-(trifluoromethyl)phenyl]carbamothioyl]amino)methyl]-2',3'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-(4-benzyl-1H-1,2,3-triazol-1-yl)-2',5'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-(4-chlorophenyl-1,2,3-triazol-1-yl)-5'-deoxy-alpha-D-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-(4-chlorophenyl-1,2,3-triazol-1-yl)-5'-deoxy-beta-D-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-([[4-chloro-3-(trifluoromethyl)phenyl]carbamothioyl]amino)-2',5'-dideoxy-3,4-dihydro-alpha-thymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-([[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl]amino)-2',5'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-azido-2',5'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-[4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl]-2',5'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-[5-(2-aminobenzyl)-1H-1,2,3-triazol-1-yl]-2',5'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5'-[5-amino-4-[4-chloro-3-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl]-2',5'-dideoxy-3,4-dihydrothymidine
-
 Mycobacterium tuberculosis
2.7.4.9 5-(5'-amino-5'-deoxy-beta-D-thymidin-5'-N-yl)-1-(4-chloro-3-trifluoromethylphenyl)-tetrazole
-
 Mycobacterium tuberculosis
2.7.4.9 additional information not inhibited by N-(5'-deoxy-4-thio-alpha-D-thymidin-5'-yl)-N'-phenylthiourea Mycobacterium tuberculosis
2.7.4.9 N-(5'-deoxy-4-thio-alpha-D-thymidin-5'-yl)-N'-(3-trifluoromethyl-4-chlorophenyl)thiourea
-
 Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
2.7.4.9 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.7.4.9 ATP + dTMP
-
 Mycobacterium tuberculosis ADP + dTDP
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.7.4.9 thymidine monophosphate kinase
-
 Mycobacterium tuberculosis
2.7.4.9 TMPK
-
 Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.7.4.9 0.00017
-
 N-(5'-deoxy-4-thio-alpha-D-thymidin-5'-yl)-N'-(3-trifluoromethyl-4-chlorophenyl)thiourea in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0006
-
 5'-([[4-chloro-3-(trifluoromethyl)phenyl]carbamothioyl]amino)-2',5'-dideoxy-3,4-dihydro-alpha-thymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0021
-
 5'-[4-(4-chlorophenyl)-1H-1,2,3-triazol-1-yl]-2',5'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0023
-
 5'-[5-(2-aminobenzyl)-1H-1,2,3-triazol-1-yl]-2',5'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0027
-
 5'-(4-benzyl-1H-1,2,3-triazol-1-yl)-2',5'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0028
-
 2',5'-dideoxy-5'-([[3-(trifluoromethyl)phenyl]carbamoyl]amino)-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0042
-
 2',5'-dideoxy-5'-(4-phenyl-1H-1,2,3-triazol-1-yl)-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.005
-
 3'-[([[4-chloro-3-(trifluoromethyl)phenyl]carbamothioyl]amino)methyl]-2',3'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.006
-
 3'-azido-3'-deoxy-alpha-D-thymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.009
-
 5'-(4-chlorophenyl-1,2,3-triazol-1-yl)-5'-deoxy-alpha-D-thymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0099
-
 5'-([[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl]amino)-2',5'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.015
-
 3'-(4-chlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-4-thio-beta-D-thymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.0265
-
 5'-azido-2',5'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.028
-
 3',5'-diazido-2',3',5'-trideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.035
-
 3'-(4-chlorophenyl-1,2,3-triazol-1-yl)-3'-deoxy-alpha-D-thymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.037
-
 1-(((2R,3S,5S)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)methyl)-3-(((2S,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)methyl)urea in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.045
-
 5'-[5-amino-4-[4-chloro-3-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-yl]-2',5'-dideoxy-3,4-dihydrothymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.073
-
 5-(5'-amino-5'-deoxy-beta-D-thymidin-5'-N-yl)-1-(4-chloro-3-trifluoromethylphenyl)-tetrazole in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.1
-
 3'-azido-3'-deoxy-4-thio-beta-D-thymidine Ki above 0.1 mM, in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis
2.7.4.9 0.201
-
 5'-(4-chlorophenyl-1,2,3-triazol-1-yl)-5'-deoxy-beta-D-thymidine in 50 mM Tris-HCl, pH 7.4, 50 mM KCl, 2 mM MgCl2, at 37°C Mycobacterium tuberculosis