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2.7.1.20: adenosine kinase

This is an abbreviated version!
For detailed information about adenosine kinase, go to the full flat file.

Word Map on EC 2.7.1.20

Reaction

ATP
+
adenosine
=
ADP
 +
AMP

Synonyms

adenosine kinase (phosphorylating), ADK, AdK-L, AdK-S, Ado kinase, AdoK, AK, ATP:adenosine 5'-phosphotransferase, CpAK, hADK, kinase, adenosine (phosphorylating), LdAdK, MGG_06270, Rv2202c, Tb927.6.2360, TbAK

ECTree

     2 Transferases
         2.7 Transferring phosphorus-containing groups
             2.7.1 Phosphotransferases with an alcohol group as acceptor
                2.7.1.20 adenosine kinase

Inhibitors

Inhibitors on EC 2.7.1.20 - adenosine kinase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-6-ethyl-6-[4-[(2,6-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,3,5,6-tetrafluorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,3-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,4-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,4-difluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,5-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,5-dimethoxyphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2,6-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-chloro-4-fluorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-chloro-4-iodophenyloxy)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-chloro-4-iodophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
6.5% inhibition at 0.015 mM
(+/-)-6-ethyl-6-[4-[(2-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]thiazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-fluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-imidazolylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-methyl-6-chlorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-pyrazylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-pyridylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(2-pyrimidylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3,4-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-chloro-4-fluorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-fluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-methoxyphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-methylphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-trifluoromethoxyphenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo [1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(3-trifluoromethylphenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(4-bromophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(4-ethynylphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
16% inhibition at 0.015 mM
(+/-)-6-ethyl-6-[4-[(4-fluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
13% inhibition at 0.015 mM
(+/-)-6-ethyl-6-[4-[(4-iodophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(4-iodophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]thiazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(4-methoxyphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(4-nitrophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(4-trifluoromethoxyphenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[(phenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
15% inhibition at 0.015 mM
(+/-)-6-ethyl-6-[4-[3-(2-diethylaminoethyl)phenoxymethyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[3-(2-hydroxye)thylphenoxymethyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[3-(2-pyrrolidin-1-ylethyl)phenoxymethyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[[4-[2-(trimethylsilyl)ethynyl]phenylthio]-methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-ethyl-6-[4-[[4-[2-(trimethylsilyl)ethynyl]phenylthio]-methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]thiazepin-7-one
-
-
(+/-)-6-[4-[(2-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-[4-[(3-trifluoromethylphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(+/-)-6-[4-[(phenylthio)methyl]phenyl]-6,7-dihydrobenzo-[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(-)-6-ethyl-6-[4-[(2,6-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
-
-
(1R,2R,3S,4R,5S)-4-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 82.5% inhibition
(1R,2R,3S,4R,5S)-4-(4-anilino-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 85.4% inhibition
(1R,2S,3R,4R,5S)-1-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(aminomethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 50.9% inhibition
(1R,2S,3R,4R,5S)-1-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(azidomethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 80.5% inhibition
(1R,2S,3R,4R,5S)-1-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 58.2% inhibition
(1R,2S,3R,4R,5S)-1-(4-anilino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 85.1% inhibition
(1R,2S,3R,4R,5S)-1-(4-anilino-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 88.3% inhibition
(1R,2S,3R,4R,5S)-1-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-(hydroxymethyl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 76.5% inhibition
(1R,2S,3R,4S,5S)-1-(4-anilino-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-methylbicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 88.1% inhibition
(1R,2S,3R,4S,5S)-1-[4-(4-fluoroanilino)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-4-methylbicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 86.9% inhibition
(1R,2S,3R,4S,5S)-1-[4-anilino-5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-4-methylbicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 78.4% inhibition
(1R,2S,3R,4S,5S)-4-amino-1-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)bicyclo[3.1.0]hexane-2,3-diol
0.05 mM, 60.4% inhibition
(1R,2S,3R,5R)-3-(6-(4-([1,1'-biphenyl]-4-yl)piperazin-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
-
(1S,2R,3S,5R)-3-amino-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclopentane-1,2-diol
0.05 mM, 88.4% inhibition
(2R,3R,4R)-2-[5-phenyl-4-(phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]tetrahydrofuran-3,4-diol
-
(2R,3R,4S,5R)-2-(6-(4-(4-(1-(difluoromethyl)-1H-pyrazol-4-yl)phenyl)piperazin-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
-
(2R,3R,4S,5R)-2-(6-(4-([1,1'-biphenyl]-4-yl)piperazin-1-yl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
-
(2R,3R,4S,5R)-2-(6-([1,1'-biphenyl]-4-ylethynyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
-
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diol
-
compound displays very significant antimycobacterial activity, IC50 value 0.3 microM, but shows the highest cytotoxicity of the compounds tested. Compound only weakly inhibits in vitro adenosine kinase
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(3'-(morpholinomethyl)-[1,1'-biphenyl]-4-yl)piperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(4'-(2-hydroxypropan-2-yl)-[1,1'-biphenyl]-4-yl)piperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
-
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)piperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
-
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(4-(6-(trifluoromethyl)pyridin-3-yl)phenyl)piperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(4-(6-methoxypyridin-3-yl)phenyl)piperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
-
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(phenylethynyl)phenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
-
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-phenylpiperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[4-(1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]tetrahydrofuran-3,4-diol
-
compound exhibits moderate antimycobacterial activity, IC50 value 15.6 microM, accompanied by preferentialinhibition of adenosine kinase and low cytotoxicity
(2S,3S,4R,5R)-2-amino-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diol
-
-
1-(4-fluorobenzyloxy)-adenosine
-
0.1 mM, 10-90% inhibition
1-deaza-2-amino-6-chloropurine riboside
-
0.1 mM, 10-90% inhibition
10-(dimethylamino)-6-phenylpyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one
-
-
2',3',5'-tri-O-acetyl-adenosine
10-90% inhibition at 0.1 mM
2',3'-isopropylidene adenosine
-
weak inhibition
2'-deoxy-2,2'-difluoro-adenosine
10-90% inhibition at 0.1 mM
2'-deoxy-adenosine
10-90% inhibition at 0.1 mM
2'-deoxyadenosine
2'-deoxycoformycin
-
0.1 mM, 10-90% inhibition
2'-O-methyl-adenosine
10-90% inhibition at 0.1 mM
2,3-difluoro-3-deaza-7-iso-adenosine
2,3-difluoro-3-deaza-7-isoadenosine
-
0.1 mM, 18% inhibition of phosphorylation of adenosine
2,3-difluoro-3-deaza-adenosine
-
0.1 mM, 12% inhibition
2,3-difluoro-3-deazaadenosine
-
0.1 mM, 12% inhibition of phosphorylation of adenosine
2,4,6-trimethyl-6-benzylthioinosine
-
-
2,4-dichloro-6-benzylthioinosine
-
-
2,5'-anhydroformycin
-
-
2,N6-dimethyladenosine
-
0.1 mM, 10-90% inhibition
2,O6-dimethylinosine
-
0.01 mM, 10-90% inhibition
2-(1-ethyn-1-yl)-adenosine
-
0.1 mM, 10-90% inhibition
2-amino-6-oxypurine riboside
-
0.1 mM, 10-90% inhibition
2-Aminoadenosine
-
0.1 mM, 10-90% inhibition
2-azaadenosine
-
0.01 mM, 10-90% inhibition
2-azido-O6-methylinosine
2-azidoadenosine
-
0.01 mM, 10-90% inhibition
2-bromoadenosine
-
0.01 mM, 10-90% inhibition
2-carboxyethyl phosphonic acid
-
-
2-carboxyethylphosphonic acid
-
-
2-chloro-2'-deoxy-2'-fluoro-9-[beta-D-arabinofuranosyl]-adenine
10-90% inhibition at 0.1 mM
2-chloro-2'-deoxy-2'-fluoro-adenosine
10-90% inhibition at 0.01 mM
2-chloro-2'-deoxy-adenosine
10-90% inhibition at 0.1 mM
2-chloro-4'-thio-adenosine
10-90% inhibition at 0.1 mM
2-chloro-6-benzylthioinosine
-
-
2-chloro-6-fluoro-6-benzylthioinosine
-
-
2-chloro-6-methoxypurine riboside
-
0.01 mM, 10-90% inhibition
2-chloro-adenosine
10-90% inhibition at 0.01 mM
2-chloroadenosine
2-chloropurine riboside
-
0.1 mM, 10-90% inhibition
2-ethyladenosine
-
0.1 mM, 10-90% inhibition
2-fluoro-3-deaza-adenosine
2-fluoro-3-deaza-N6-methyl-adenosine
2-fluoro-3-deazaadenosine
2-fluoro-4-(benzofuran-2-yl)-7-(beta-d-ribofuranosyl)-7H-pyrrolo-[2,3-d]pyrimidine
-
potent and selective inhibition, moderate effect against whole cells. MIC value 62.5 microM
2-fluoro-6-benzylthioinosine
-
-
2-fluoro-8-azaadenosine
-
0.01 mM, 10-90% inhibition
2-fluoro-9-[beta-D-arabinofuranosyl]-adenine
10-90% inhibition at 0.1 mM
2-fluoro-adenosine
2-fluoroadenosine
2-hydroxyadenosine
-
0.1 mM, 10-90% inhibition
2-methyl-6-benzylthioinosine
-
-
2-methyl-6-oxypurine riboside
-
0.001 mM, 10-90% inhibition
2-methyl-adenosine
10-90% inhibition at 0.1 mM
2-methyl-N6-benzoyladenosine
-
0.1 mM, 10-90% inhibition
2-methyl-N6-octyladenosine
-
0.01 mM, 10-90% inhibition
2-methyl-S6-phenyl-6-mercaptopurine riboside
-
0.1 mM, 10-90% inhibition
2-methyladenosine
-
0.1 mM, 10-90% inhibition
2-Phenylethylureidopurine ribonucleoside
-
competitive inhibition
2-tert-butyl-4H-benzo[1,2,4]thiadiazine-3-thione
-
36% inhibition at 0.002 mM, 68% inhibition at 0.004 mM, 83% inhibition at 0.01 mM
2-[2-(3,4-dihydroxy-phenyl)-5-phenyl-1H-imidazol-4-yl]-fluoren-9-one
-
87% inhibition at 0.002 mM, 89% inhibition at 0.004 mM, 96% inhibition at 0.01 mM
2-[3-(1H-benzoimidazol-2-yl)-6-methoxy-chromen-2-ylideneamino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid amide
-
20% inhibition at 0.002 mM, 56% inhibition at 0.004 mM, 81% inhibition at 0.01 mM; 20% inhibition at 0.020 mM, 56% inhibition at 0.040 mM, 81% inhibition at 0.1 mM
3'-deoxy-3'-azido-adenosine
-
10-90% inhibition at 0.1 mM
3'-deoxyadenosine
3,4-dichloro-6-benzylthioinosine
-
-
3-chloro-3-deaza-adenosine
3-chloro-3-deazaadenosine
3-deaza-adenosine
-
0.1 mM, 6% inhibition
3-deazaadenosine
3-fluoro-3-deaza-adenosine
-
0.1 mM, 12% inhibition
3-fluoro-3-deazaadenosine
-
0.1 mM, 12% inhibition of phosphorylation of adenosine
3-methyl-6-benzylthioinosine
-
-
3-nitro-6-benzylthioinosine
-
-
3-trifluoromethyl-6-benzylthioinosine
-
-
3-[3-(4-hydroxy-phenyl)-4-oxo-2-thioxo-thiazolidin-5-ylidene]-1-methyl-1,3,3a,7a-tetrahydro-indol-2-one
-
68% at 0.020 mM, 88% inhibition at 0.04 mM, 98% inhibition at 0.1 mM; 68% inhibition at 0.002 mM, 88% inhibition at 0.004 mM, 98% inhibition at 0.01 mM
3-[5,6-bis-(4-methoxy-phenyl)-furo[2,3-d]pyrimidin-4-ylamino]-propan-1-ol
-
86% inhibition at 0.002 mM, 87% inhibition at 0.004 mM, 89% inhibition at 0.01 mM
3-[beta-D-ribofuranosyl]-adenine
10-90% inhibition at 0.01 mM
4,5'-anhydroformycin
-
-
4-(1H-pyrazol-4-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
4-(furan-2-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
4-(furan-3-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
4-acetoxy-6-benzylthioinosine
-
-
4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido[2,3-d]pyrimidine
-
-
4-Amino-5-imidazolecarboxamide riboside
-
-
4-amino-5-iodo-7-(4'-C-spirocyclopropyl-beta-D-erythropentofuranosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 600 nM
4-amino-5-iodo-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]-pyrimidine
-
IC50: 6 nM
4-amino-5-iodo-7beta-D-ribofuranosyl-7H-pyrrole(2,3-d)-pyrimidine
-
100% inhibition
4-bromo-6-benzylthioinosine
-
-
4-chloro-6-benzylthioinosine
-
-
4-cyano-6-benzylthioinosine
-
-
4-fluoro-6-benzylthioinosine
-
-
4-methoxy-6-benzylthioinosine
-
-
4-methyl-6-benzylthioinosine
-
-
4-N-(2-methoxyphenyl)amino-5-(4-ethoxyphenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 5.3 nM
4-N-(3,4-ethylenedioxyphenyl)amino-5-(2-methylphenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 1 nM
4-N-(3,4-ethylenedioxyphenyl)amino-5-phenyl-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 4 nM
4-N-(3-ethoxyphenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 2 nM
4-N-(4-bromophenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 5 nM
4-N-(4-cyanophenyl)amino-5-(4-chlorophenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 7 nM
4-N-(4-cyanophenyl)amino-5-(4-ethoxyphenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 2 nM
4-N-(4-ethoxyphenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 3 nM
4-N-(4-fluorophenyl)amino-5-(3-aminophenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 10 nM
4-N-(4-fluorophenyl)amino-5-phenyl-7-(4'-C-spirocyclopropyl-beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 0.3 nM
4-N-(4-fluorophenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 6 nM
4-N-phenylamino-5-phenyl-7-(5'-deoxy-4'-C-methyl-beta-D-ribo-furanosyl)pyrrolo[2,3-d]pyrimidine
-
IC50: 4000 nM
4-N-phenylamino-5-phenyl-7-(beta-D-erythro-furanosyl)-pyrrolo[2,3-d]pyrimidine
-
IC50: 4 nM
4-nitro-6-benzylthioguanosine
-
0.2 mM, partial inhibition
4-nitro-6-benzylthioinosine
4-tert-butyl-6-benzylthioinosine
-
-
4-trifluoromethoxy-6-benzylthioinosine
-
-
5'-amino-5'-deoxy-adenosine
5'-amino-5'-deoxyadenosine
-
adenosine phosphorylation is inhibited by 100fold excess of the inhibitor
5'-carboxamido-adenosine
10-90% inhibition at 0.1 mM
5'-Deoxy-5'-aminoadenosine
-
strong, kinetic studies
5'-deoxy-5-iodotubercidin
-
following systemic administration, adenosine kinase inhibitors can alleviate acute thermal nociception as measured by the hot-plate test in mice
5'-deoxy-adenosine
10-90% inhibition at 0.01 mM
5'-deoxyadenosine
5-benzyl-6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]pyrimidin-4-amine
-
5-fluoro-4-(furan-2-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
5-fluoro-4-(furan-3-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
5-fluoro-7-(beta-D-ribofuranosyl)-4-(thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
5-fluoro-7-(beta-D-ribofuranosyl)-4-(thiophen-3-yl)-7H-pyrrolo[2,3-d]pyrimidine
5-iodo-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
0.05 mM, 88.3% inhibition
5-iodotubercidin
5-[4-(dimethylamino)phenyl]-6-{[6-(morpholin-4-yl)pyridin-3-yl]ethynyl}pyrimidin-4-amine
-
6,8-bis(anilin-N-yl)-9-(beta-D-ribofuranosyl)purine
-
IC50: 90 nM
6,8-bis(indolin-N-yl)-9-(beta-D-ribofuranosyl)purine
-
IC50: 2000 nM
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
binds to a putative allosteric site
6-benzylmercaptopurine riboside
6-benzylthioinosine
-
-
6-bromopurine riboside
-
0.01 mM, 10-90% inhibition
6-Chloropurine riboside
-
0.01 mM, 10-90% inhibition
6-cyclopentyloxypurine riboside
6-dimethylaminopurine riboside
-
-
6-ethyl-6-(3-methylphenyl)pyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
-
-
6-ethyl-6-(4-methylphenyl)pyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
-
-
6-ethyl-6-phenylpyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
-
-
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
binds to a putative allosteric site
6-fluoro-8-aminopurine riboside
-
0.1 mM, 10-90% inhibition
6-fluoromethylpurine riboside
-
0.01 mM, 10-90% inhibition
6-gamma,gamma-dimethylallylaminopurine riboside
-
90% inhibition
6-indolin-N-yl-8-chloro-9-(beta-D-ribofuranosyl)purine
-
IC50: 480 nM
6-indolin-N-yl-8-iodo-9-(beta-D-ribofuranosyl)purine
-
IC50: 1000 nM
6-indolin-N-yl-8-methylthio-9-(beta-D-ribofuranosyl)-purine
-
IC50: 150 nM
6-indolin-N-yl-8-vinyl-9-(beta-D-ribofuranosyl)purine
-
IC50: 60 nM
6-iodopurine riboside
-
0.1 mM, 10-90% inhibition
6-mercaptopurine riboside
6-methoxypurine riboside
6-methyl-purine riboside
10-90% inhibition at 0.01 mM
6-methylaminopurine riboside
-
-
6-Methylmercaptopurine riboside
6-methylmercaptopurine riboside phosphate
6-methylpurine riboside
-
0.01 mM, 10-90% inhibition
6-nitrobenzylmercaptopurine riboside
6-phenyl-6,7-dihydropyrrolo[2,1-d][1,5]benzothiazepin-7-yl acetate
-
-
6-phenyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepin-7-yl acetate
-
-
6-phenylpyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one
-
-
6-phenylpyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
-
-
6-Ureidopurine ribonucleosides
-
-
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
binds to a putative allosteric site
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]-5-(2-phenylethyl)pyrimidin-4-amine
-
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]-5-(3-phenylpropyl)pyrimidin-4-amine
-
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]-5-(4-phenylbutyl)pyrimidin-4-amine
-
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]pyrimidin-4-amine hydrate (1:1)
-
7-(2-naphthyl)-7-deazaadenine
7-(3-dibenzo[b,d]furanyl)-7-deazaadenine
submicromolar Mycobacterium tuberculosis-specific inhibitor, and active against Mycobacterium tuberculosis strains with a MIC of 4 microM
7-(beta-D-ribofuranosyl)-4-(1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
7-(beta-D-ribofuranosyl)-4-(thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
7-(beta-D-ribofuranosyl)-4-(thiophen-3-yl)-7H-pyrrolo[2,3-d]pyrimidine
7-beta-D-ribofuranosyl-pyrrolo-(2,3-d)-pyrimidine
-
competitive with respect to 6-methylmercaptopurine riboside and noncompetitive with respect to ATP
7-cyano-7-deazaadenosine
7-deaza-7-carboxamidoadenosine
-
0.01 mM, 10-90% inhibition
7-deaza-carbocyclic-adenosine
10-90% inhibition at 0.1 mM
7-deazaadenosine
-
0.01 mM, 10-90% inhibition
7-Deazainosine
-
-
7-iodo-7-deazaadenosine
7-[4-([1,1'-biphenyl]-4-yl)piperazin-1-yl]-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine
-
7-[alpha-D-arabinofuranosyl]-adenine
10-90% inhibition at 0.1 mM
7-[alpha-D-ribofuranosyl]-adenine
10-90% inhibition at 0.1 mM
8-acetylenyl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)-purine
-
IC50: 1000 nM
8-aminopurine riboside
-
0.1 mM, 10-90% inhibition
8-anilin-N-yl-6-indolin-N-yl-9-(5-deoxy-beta-D-ribofuranosyl)purine
-
IC50: 200 nM
8-anilin-N-yl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)-purine
-
IC50: 19 nM
8-aza-2'-deoxy-adenosine
10-90% inhibition at 0.1 mM
8-aza-8-[beta-D-ribofuranosyl]-adenine
10-90% inhibition at 0.1 mM
8-aza-9-deazaadenosine
8-aza-adenosine
10-90% inhibition at 0.01 mM, competitive inhibitor
8-aza-carbocyclic-adenosine
8-azaadenosine
8-azaguanosine
-
weak inhibition
8-azidoadenosine
-
0.1 mM, 10-90% inhibition
8-azidopurine riboside
-
0.1 mM, 10-90% inhibition
8-Bromoadenosine
-
0.1 mM, 10-90% inhibition
8-bromopurine riboside
-
0.1 mM, 10-90% inhibition
8-chloroadenosine
-
0.1 mM, 10-90% inhibition
8-chloropurine riboside
-
0.1 mM, 10-90% inhibition
8-dimethylaminopurine riboside
-
0.1 mM, 10-90% inhibition
8-ethyl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)purine
-
IC50: 230 nM
8-furan-2-yl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)-purine
-
IC50: 2900 mM
8-hydroxypurine riboside
-
0.1 mM, 10-90% inhibition
8-mercaptopurine riboside
-
0.1 mM, 10-90% inhibition
8-methoxypurine riboside
-
0.1 mM, 10-90% inhibition
9-(2-deoxy-beta-D-erythropentopyranosyl)-adenine
10-90% inhibition at 0.1 mM
9-deazaadenosine
-
0.01 mM, 10-90% inhibition
9-[alpha-D-ribofuranosyl]-adenine
10-90% inhibition at 0.1 mM
9-[alpha-L-lyxofuranosyl]-2-fluoro-adenine
10-90% inhibition at 0.1 mM
9-[alpha-L-lyxofuranosyl]-adenine
10-90% inhibition at 0.1 mM
9-[beta-D-5-methyl-(allo)-ribofuranosyl]-2-fluoro-adenine
10-90% inhibition at 0.01 mM
9-[beta-D-5-methyl-(allo)-ribofuranosyl]-6-methyl-purine
10-90% inhibition at 0.01 mM
9-[beta-D-5-methyl-(talo)-ribofuranosyl]-2-fluoro-adenine
10-90% inhibition at 0.1 mM
9-[beta-D-5-methyl-(talo)-ribofuranosyl]-6-methyl-purine
10-90% inhibition at 0.1 mM
9-[beta-D-ribofuranosyl]purine
-
0.1 mM, 10-90% inhibition
adenosine
adenosine-5'-pentaphospho-5'-adenosine
adenosine-5'-tetraphospho-5'-adenosine
adenosine-N1-oxide
-
0.1 mM, 10-90% inhibition
aristeromycin
10-90% inhibition at 0.1 mM
ATP-analogs
-
-
Begomovirus AL2
-
Begomovirus protein expressed in infected tobacco plants inactivates the adenosine kinase
-
Bisadenylyl polyphosphates
carbocyclic 6-(2,3,4-trimethylbenzylthio)inosine
-
-
carbocyclic 6-(2,4-dichlorobenzylthio)inosine
-
-
carbocyclic 6-(2-chloro-6-fluorobenzylthio)inosine
-
-
carbocyclic 6-(2-chlorobenzylthio)inosine
-
-
carbocyclic 6-(2-fluorobenzylthio)inosine
-
-
carbocyclic 6-(2-methylbenzylthio)inosine
-
-
carbocyclic 6-(3,4-dichlorobenzylthio)inosine
-
-
carbocyclic 6-(3-methylbenzylthio)inosine
-
-
carbocyclic 6-(3-nitrobenzylthio)inosine
-
-
carbocyclic 6-(3-trifluoromethylbenzylthio)inosine
-
-
carbocyclic 6-(4-bromobenzylthio)inosine
-
-
carbocyclic 6-(4-chlorobenzylthio)inosine
-
-
carbocyclic 6-(4-cyanobenzylthio)inosine
-
weakest inhibitor
carbocyclic 6-(4-fluorobenzylthio)inosine
-
-
carbocyclic 6-(4-methoxybenzylthio)inosine
-
-
carbocyclic 6-(4-methoxycarbonylbenzylthio)inosine
-
-
carbocyclic 6-(4-methylbenzylthio)inosine
-
-
carbocyclic 6-(4-methylsulfonylbenzylthio)inosine
-
-
carbocyclic 6-(4-nitrobenzylthio)inosine
-
-
carbocyclic 6-(4-trifluoromethoxybenzylthio)inosine
-
-
carbocyclic 6-(p-methoxycarbonylbenzylthio)inosine
-
-
carbocyclic 6-benzylthioinosine
-
-
clodronate
-
inhibits adenosine kinase activity in a dose-dependent manner in the presence of 10 mM phosphate
coformycin
-
-
Curtovirus L2
-
Curtovirus protein expressed in infected tobacco plants inactivates the adenosine kinase
-
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-benzofuryl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-furyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thiazolyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thienyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thienyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-furyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-furyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-thienyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-thienyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(4-dibenzofuryl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(4-pyrazolyl)-7 H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
cyclohexyl-(2-thiophen-2-ylimidazo[1,2-a]pyrazin-3-yl)-amine
-
40% inhibition at 0.002 mM, 61% inhibition at 0.004 mM, 78% inhibition at 0.01 mM; 40%inhibition at 0.02 mM, 61% inhibition at 0.040 mM, 78% inhibition at 0.1 mM
cyclopentyl-(2-thiophen-2-ylimidazo[1,2-a]pyrazin-3-yl)-amine
-
57% at 0.020 mM, 66% inhibition at 0.04 mM, 73% inhibition at 0.1 mM; 57% inhibition at 0.002 mM, 66% inhibition at 0.004 mM, 73% inhibition at 0.01 mM
cytidine
-
0.1 mM, 10-90% inhibition
deoxyadenosine
Deoxycoformycin
-
-
deoxyguanosine
deoxymethylthioadenosine
-
weak inhibition
diethylphosphonoacetic acid
-
-
dipyridamole
-
at low adenosine levels
DTNB
-
substrates protect
etidronate
-
inhibits adenosine kinase activity in a dose-dependent manner in the presence of 10 mM phosphate
Formycin A
-
at very high concentrations, kinetics
GDP
-
non competitive with respect to adenosine and competitive with respect to ATP
geminivirus AL2
-
geminivirus L2
-
guanosine
Hg2+
-
strong inhibition, reducing agent reverses
iodotubercidin
K+
-
inhibition by increasing concentrations
methylphosphonic acid
-
-
MgADP-
-
product inhibition, linear, noncompetitive with respect to MgATP2- and adenosine
MgATP2-
-
above 1 mM
Mn2+
-
strong inhibition above 1 mM
N-(5,6-diphenyl-furo[2,3-d]pyrimidin-4-yl)-propionamide
-
40% inhibition at 0.002 mM, 61% inhibition at 0.004 mM, 78% inhibition at 0.01 mM
N-(phosphonomethyl)-glycine
-
-
N-(phosphonomethyl)iminodiacetic acid
-
-
N-phosphomethyl glycine
-
-
N-phosphomethyl iminodiacetic acid
-
-
N1-benzyladenosine
N1-ethyladenosine
N1-methyladenosine
N1-oxy-N6-methyladenosine
-
0.1 mM, 10-90% inhibition
N6-aminoadenosine
-
0.1 mM, 10-90% inhibition
N6-delta2-isopentenyl-adenosine
-
competitive with respect to adenosine
Na+
-
inhibition by increasing concentrations
NH4+
-
slight inhibition
NSC 113939
-
-
NSC 113940
-
-
Nucleoside analogs
-
overview
Nucleosides
p-hydroxymercuribenzoate
P1,P3-di(adenosine-5')triphosphate
-
-
P1,P4-di(adenosine-5')tetraphosphate
-
-
P1,P5-di(adenosine-5')pentaphosphate
-
Phenylglyoxal
-
inhibition levels of wild-type and mutant enzymes, overview
Phosphonoacetic acid
Polyclonal antibodies to adenosine kinase from Leishmania donovani
-
not from other eukaryotic sources
-
S-adenosylhomocysteine
-
97% inhibition
tubercidin
uridine
Xanthosine
-
weak inhibition
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-phenyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-2-yl]methyl octadecyl hydrogen phosphate
-
octadecylphosphate prodrug designed as lipophilic derivatives with increased penetration through the mycobacterial cell wall, no antimycobacterial activity
additional information
-