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Literature summary for 2.7.7.53 extracted from

  • Goetz, K.H.; Hacker, S.M.; Mayer, D.; Duerig, J.N.; Stenger, S.; Marx, A.
    Inhibitors of the diadenosine tetraphosphate phosphorylase Rv2613c of Mycobacterium tuberculosis (2017), ACS Chem. Biol., 12, 2682-2689 .
    View publication on PubMed
Search for more literature for 2.7.7.53

Inhibitors

Inhibitors Comment Organism Structure
(11aR,13S,14R,15S,15aR)-2,3,4,5,6,7-hexahydroxy-9,17-dioxo-9,11,11a,13,14,15,15a,17-octahydrodibenzo[g,i]pyrano[3,2-b][1,5]dioxacycloundecine-13,14,15-triyl tris(3,4,5-trihydroxybenzoate) 29.96% activity remaining Mycobacterium tuberculosis
1,2,3,4,6-pentakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose 35.81% activity remaining Mycobacterium tuberculosis
1,2,3,6-tetrakis-O-(3,4,5-trihydroxybenzoyl)-beta-D-glucopyranose 47.50% activity remaining Mycobacterium tuberculosis
10-(3,4-dimethoxyphenyl)-7,7-dimethyl-7,8,10,10a-tetrahydro-6H-indeno[1,2-b]quinoline-9,11-dione 24.76% activity remaining Mycobacterium tuberculosis
2-(4-chlorobenzene-1-sulfonyl)-3-(methylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile 1.59% activity remaining Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(3-ethylanilino)-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(3-methoxyanilino)-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(3-methylanilino)-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(benzylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(ethylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(methylsulfanyl)-3-(3-nitroanilino)propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(methylsulfanyl)-3-(3-propylanilino)propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[2-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[3-(propan-2-yl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile docking structure Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[4-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-(propylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-[(3,3-dimethylcyclohexa-1,5-dien-1-yl)amino]-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-[(prop-2-en-1-yl)sulfanyl]-3-[3-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-[(propan-2-yl)sulfanyl]-3-[3-(trifluoromethyl)anilino]propanenitrile
-
 Mycobacterium tuberculosis
2-(benzenesulfonyl)-3-[[3,3-bis(trifluoromethyl)cyclohexa-1,5-dien-1-yl]amino]-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
2-amino-3-[(E)-([2-[(4-chlorophenyl)sulfanyl]phenyl]methylidene)amino]butanedinitrile 46.29% activity remaining Mycobacterium tuberculosis
2-amino-4-(3,4-dimethoxyphenyl)-7-methyl-3-nitro-4H,5H-pyrano[4,3-b]pyran-5-one 48.50% activity remaining Mycobacterium tuberculosis
2-amino-5-(4-ethoxyphenyl)-5,11-dihydro-3H-indeno[2',1':5,6]pyrido[2,3-d]pyrimidine-4,6-dione 48.87% activity remaining Mycobacterium tuberculosis
2-ethoxyethyl 4-(3-bromo-4-methoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate 31.80% activity remaining Mycobacterium tuberculosis
2-iodo-5-[(4-methylphenyl)methyl]pyridin-3-ol 29.63% activity remaining Mycobacterium tuberculosis
2-[(2-[[2-(3-fluoro-4-nitroanilino)-2-oxoethyl]sulfanyl]-1,3-benzothiazol-6-yl)carbamoyl]benzoic acid 43.56% activity remaining Mycobacterium tuberculosis
2-[[6-amino-4-(2-chlorophenyl)-3,5-dicyanopyridin-2-yl]sulfanyl]-N-benzylacetamide 42.76% activity remaining Mycobacterium tuberculosis
3-(3-chloro-4-hydroxy-5-methoxyphenyl)-2,3,6,7,8,9-hexahydro-5H-[1]benzothieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidin-5-one 43.92% activity remaining Mycobacterium tuberculosis
3-anilino-2-(4-chlorobenzene-1-sulfonyl)-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
3-anilino-2-(benzenesulfonyl)-3-(methylsulfanyl)propanenitrile
-
 Mycobacterium tuberculosis
3-[[2-(benzenesulfonyl)-2-cyano-1-(methylsulfanyl)ethyl]amino]benzonitrile
-
 Mycobacterium tuberculosis
4-([[9-(3,4-dimethoxyphenyl)-8-oxo-4,5,6,7,8,9-hexahydro[1,2,4]triazolo[5,1-b]quinazolin-2-yl]sulfanyl]methyl)benzoic acid 33.53% activity remaining Mycobacterium tuberculosis
5,5',6,6',8,8'-hexahydroxy-2,2'-dimethyl-2,2',3,3'-tetrahydro-4H,4'H-[9,9'-binaphtho[2,3-b]pyran]-4,4'-dione no activity remaining Mycobacterium tuberculosis
5-(2,4-dichlorophenyl)-2-methyl-2,3,5,6-tetrahydro-4H-pyrano[2,3-a][4,7]phenanthrolin-4-one 42.23% activity remaining Mycobacterium tuberculosis
7-(4-chlorophenyl)-1,7-dimethyl-N-[2-(morpholin-4-yl)ethyl]-9-oxo-8,9-dihydro-7H-furo[3,2-f][1]benzopyran-2-carboxamide 32.08% activity remaining Mycobacterium tuberculosis
7-(4-fluorophenyl)-1,7-dimethyl-9-oxo-N-propyl-8,9-dihydro-7H-furo[3,2-f][1]benzopyran-2-carboxamide 48.72% activity remaining Mycobacterium tuberculosis
7-(4-fluorophenyl)-1,7-dimethyl-N-[3-(morpholin-4-yl)propyl]-9-oxo-8,9-dihydro-7H-furo[3,2-f][1]benzopyran-2-carboxamide 47.73% activity remaining Mycobacterium tuberculosis
ethyl 4-[2,5-bis(sulfanylidene)-4,5-dihydro[1,3]thiazolo[4',5':4,5]pyrimido[1,6-a]benzimidazol-3(2H)-yl]benzoate 42.80% activity remaining Mycobacterium tuberculosis
methyl 3-[[2-(benzenesulfonyl)-2-cyano-1-(methylsulfanyl)ethyl]amino]benzoate
-
 Mycobacterium tuberculosis
methylsulfanylacrylonitril
-
 Mycobacterium tuberculosis
additional information inhibitor library screening, cytotoxicity analysis, overview Mycobacterium tuberculosis
[(5E)-5-[[2-(4-carbamoylpiperidin-1-yl)-9-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid 28.09% activity remaining Mycobacterium tuberculosis

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ADP + ATP Mycobacterium tuberculosis
-
 phosphate + P1,P4-bis(5'-adenosyl)tetraphosphate
-
 ?
ADP + ATP Mycobacterium tuberculosis H37Rv
-
 phosphate + P1,P4-bis(5'-adenosyl)tetraphosphate
-
 ?
ADP + ATP Mycobacterium tuberculosis ATCC 25618
-
 phosphate + P1,P4-bis(5'-adenosyl)tetraphosphate
-
 ?

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WMK9
-
-
Mycobacterium tuberculosis ATCC 25618 P9WMK9
-
-
Mycobacterium tuberculosis H37Rv P9WMK9
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ADP + ATP
-
 Mycobacterium tuberculosis phosphate + P1,P4-bis(5'-adenosyl)tetraphosphate
-
 ?
ADP + ATP
-
 Mycobacterium tuberculosis H37Rv phosphate + P1,P4-bis(5'-adenosyl)tetraphosphate
-
 ?
ADP + ATP
-
 Mycobacterium tuberculosis ATCC 25618 phosphate + P1,P4-bis(5'-adenosyl)tetraphosphate
-
 ?

Synonyms

Synonyms Comment Organism
Rv2613c
-
 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
8
-
 assay at Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00012
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
0.00047
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(propylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
0.00057
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(3-ethylanilino)-3-(methylsulfanyl)propanenitrile
0.0008
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(benzylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
0.00094
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-[(propan-2-yl)sulfanyl]-3-[3-(trifluoromethyl)anilino]propanenitrile
0.00096
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(methylsulfanyl)-3-(3-propylanilino)propanenitrile
0.0013
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(methylsulfanyl)-3-(3-nitroanilino)propanenitrile
0.00147
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-[(prop-2-en-1-yl)sulfanyl]-3-[3-(trifluoromethyl)anilino]propanenitrile
0.00177
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[3-(propan-2-yl)anilino]propanenitrile
0.00182
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(ethylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
0.00251
-
 pH 8.0, 25°C Mycobacterium tuberculosis 3-[[2-(benzenesulfonyl)-2-cyano-1-(methylsulfanyl)ethyl]amino]benzonitrile
0.00462
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(3-methylanilino)-3-(methylsulfanyl)propanenitrile
0.0113
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(3-methoxyanilino)-3-(methylsulfanyl)propanenitrile
0.0163
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[4-(trifluoromethyl)anilino]propanenitrile
0.02
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(4-chlorobenzene-1-sulfonyl)-3-(methylsulfanyl)-3-[3-(trifluoromethyl)anilino]propanenitrile
0.0218
-
 pH 8.0, 25°C Mycobacterium tuberculosis methyl 3-[[2-(benzenesulfonyl)-2-cyano-1-(methylsulfanyl)ethyl]amino]benzoate
0.03
-
 pH 8.0, 25°C Mycobacterium tuberculosis 3-anilino-2-(benzenesulfonyl)-3-(methylsulfanyl)propanenitrile
0.1
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-(methylsulfanyl)-3-[2-(trifluoromethyl)anilino]propanenitrile
0.1
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-[(3,3-dimethylcyclohexa-1,5-dien-1-yl)amino]-3-(methylsulfanyl)propanenitrile
0.1
-
 pH 8.0, 25°C Mycobacterium tuberculosis 2-(benzenesulfonyl)-3-[[3,3-bis(trifluoromethyl)cyclohexa-1,5-dien-1-yl]amino]-3-(methylsulfanyl)propanenitrile
0.1
-
 pH 8.0, 25°C Mycobacterium tuberculosis 3-anilino-2-(4-chlorobenzene-1-sulfonyl)-3-(methylsulfanyl)propanenitrile

General Information

General Information Comment Organism
additional information analysis of the binding of product Ap4A in the active site of the enzyme and docking studies with the crystal structure of Rv2613c (PDB ID 3ANO). Docking model. Active site histidine residues are His151, His153, and His155 Mycobacterium tuberculosis