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Information on EC 2.7.1.20 - adenosine kinase and Organism(s) Homo sapiens
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2.7.1.20 adenosine kinaseIUBMB Comments
2-Aminoadenosine can also act as acceptor.
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Word Map
- 2.7.1.20
- nucleoside
- deaminase
- purine
- amp
- adenylate
- inosine
-
salvage
- hypoxanthine
- epilepsy
-
phosphoribosyltransferase
- 5'-nucleotidase
- 5-iodotubercidin
- riboside
- deoxyadenosine
- s-adenosylhomocysteine
- deoxycytidine
- aicar
-
anticonvulsant
- tubercidin
- dipyridamole
-
neuromodulator
- ehna
-
2\'-deoxycoformycin
-
ecto-5\'-nucleotidase
- ribokinase
-
erythro-9-2-hydroxy-3-nonyl
-
adenosinergic
- 6-methylmercaptopurine
-
3hadenosine
- 2-chloroadenosine
- coformycin
-
nitrobenzylthioinosine
-
epileptogenesis
-
hypoxanthine-guanine
-
transmethylation
-
adenosine-induced
- hgprt
-
kinase-deficient
- 2'-deoxyadenosine
-
adenosine-mediated
-
3.5.4.4
- deoxycoformycin
-
non-nucleoside
- analysis
-
2.4.2.8
- 9-beta-d-arabinofuranosyladenine
-
n6-cyclopentyladenosine
-
erythro-9-2-hydroxy-3-nonyladenine
-
dado
- ara-a
- medicine
- diagnostics
-
rephosphorylation
- pharmacology
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
adenosine kinase, adk, ado kinase, adk-l, adk-s, rv2202c, atp:adenosine 5'-phosphotransferase, ldadk, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
adenosine kinase (phosphorylating)
-
-
-
-
ADK
kinase, adenosine (phosphorylating)
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phospho group transfer
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
ATP:adenosine 5'-phosphotransferase
2-Aminoadenosine can also act as acceptor.
CAS REGISTRY NUMBER
COMMENTARY
9027-72-9
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
ATP + 2,3-difluoro-3-deaza-7-iso-adenosine
ADP + 2,3-difluoro-3-deaza-7-iso-AMP
-
0.2% of the activity with adenosine
-
-
?
ATP + 2,3-difluoro-3-deaza-7-isoadenosine
ADP + 2,3-difluoro-3-deaza-7-isoadenosine 5'-phosphate
-
specific activity: 5 nM/mg/min
-
-
?
ATP + 2,3-difluoro-3-deaza-adenosine
ADP + 2,3-difluoro-3-deaza-AMP
-
0.2% of the activity with adenosine
-
-
?
ATP + 2,3-difluoro-3-deazaadenosine
ADP + 2,3-difluoro-3-deazaadenosine 5'-phosphate
-
specific activity: 1 nM/mg/min
-
-
?
ATP + 2-amino-carbocyclic-adenosine
?
-
35.8% of the activity with adenosine
-
-
?
ATP + 3-fluoro-3-deaza-adenosine
ADP + 3-fluoro-3-deaza-AMP
-
0.04% of the activity with adenosine
-
-
?
ATP + 3-fluoro-3-deazaadenosine
ADP + 3-fluoro-3-deazaadenosine 5'-phosphate
-
specific activity: 1 nM/mg/min
-
-
?
ATP + 3-[beta-D-ribofuranosyl]-adenine
?
-
11.2% of the activity with adenosine
-
-
?
ATP + 6-bromopurine riboside
ADP + 6-bromopurine riboside 5'-phosphate
-
-
-
-
?
ATP + 6-chloropurine riboside
ADP + 6-chloropurine riboside 5'-phosphate
-
-
-
-
?
ATP + 6-fluoromethylpurine riboside
ADP + 6-fluoromethylpurine riboside 5'-phosphate
-
-
-
-
?
ATP + 8-aza-9-deazaadenosine
ADP + 8-aza-9-deazaadenosine 5'-phosphate
-
-
-
-
?
ATP + 9-[alpha-L-lyxofuranosyl]-adenine
?
-
15% of the activity with adenosine
-
-
?
ATP + 9-[beta-D-arabinofuranosyl]-adenine
?
-
0.25% of the activity with adenosine
-
-
?
ATP + 9-[beta-D-ribofuranosyl]-purine
ADP + 9-[beta-D-ribofuranosyl]-purine 5'-phosphate
-
-
-
-
?
ATP + N1-oxy-N6-methyladenosine
ADP + N1-oxy-N6-methyladenosine 5'-phosphate
-
-
-
-
?
additional information
?
-
-
hypoxia inducible factor 1-alpha-dependent repression of adenosine kinase attenuates hypoxia-induced vascular leak
-
-
?
ATP + adenosine
ADP + AMP
-
pyrimidine nucleoside triphosphates are less efficient than purine derivatives, deoxyribonucleotides less efficient than ribonucleotides
-
-
?
ATP + adenosine
ADP + AMP
intracellular adenosine, which is controlled by the key molecular regulator adenosine kinase, influences endothelial inflammation and vascular inflammatory diseases
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
hypoxia inducible factor 1-alpha-dependent repression of adenosine kinase attenuates hypoxia-induced vascular leak
-
-
?
ATP + adenosine
ADP + AMP
intracellular adenosine, which is controlled by the key molecular regulator adenosine kinase, influences endothelial inflammation and vascular inflammatory diseases
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Co2+
Fe2+
Mg2+
Mn2+
Ni2+
additional information
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
(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,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-(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-phenylpiperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
-
2,3-difluoro-3-deaza-7-isoadenosine
-
0.1 mM, 18% inhibition of phosphorylation of adenosine
2,3-difluoro-3-deazaadenosine
-
0.1 mM, 12% inhibition of phosphorylation of adenosine
2-fluoro-3-deaza-N6-methyl-adenosine
-
0.1 mM, 13% inhibition; 0.1 mM, 13% inhibition of phosphorylation of adenosine
2-fluoro-3-deazaadenosine
-
0.1 mM, 9% inhibition of phosphorylation of adenosine
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-chloro-3-deazaadenosine
-
0.1 mM, 9% inhibition of phosphorylation of adenosine
3-fluoro-3-deazaadenosine
-
0.1 mM, 12% inhibition of phosphorylation of adenosine
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
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-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
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-[4-(dimethylamino)phenyl]-6-{[6-(morpholin-4-yl)pyridin-3-yl]ethynyl}pyrimidin-4-amine
-
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-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
binds to a putative allosteric site
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
most active compound against Mycobacterium tuberculosis strain My331/88 and drug-resistant strain Praha 131 in vitro, MIC is 2 or 4 microM, respectively, cytotoxic to human cells
8-anilin-N-yl-6-indolin-N-yl-9-(5-deoxy-beta-D-ribofuranosyl)purine
-
IC50: 200 nM
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
MgADP-
-
product inhibition, linear, noncompetitive with respect to MgATP2- and adenosine
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
adenosine
-
pH and Mg2+ dependent, most severe at pH 7.4, less inhibition at pH 8.0 and no inhibition at pH 6.5
AMP
-
competitive with respect to adenosine and noncompetitive with respect to ATP
additional information
-
at pH 5.5, with equimolar concentrations of ATP and Mg2+ from 0.2 to 1 mM there is no inhibition by adenosine over a range of 0 to 0.02 mM; product inhibition study
-
additional information
-
a CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues
-
additional information
synthesis of 7-(het)aryl-7-deazaadenine ribonucleosides bearing small and bulky substituents in position 7. Compounds bearing smaller substituents inhibit both human and Mycobacterium tuberculosis ADK and are cytotoxic, whereas several bulky derivatives are specific inhibitors of the Mycobacterium tuberculosis enzyme and are not cytotoxic
-
additional information
-
synthesis of 7-(het)aryl-7-deazaadenine ribonucleosides bearing small and bulky substituents in position 7. Compounds bearing smaller substituents inhibit both human and Mycobacterium tuberculosis ADK and are cytotoxic, whereas several bulky derivatives are specific inhibitors of the Mycobacterium tuberculosis enzyme and are not cytotoxic
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00041
(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
pH 7.5, temperature not specified in the publication
0.0016
(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
pH 7.5, temperature not specified in the publication
0.0051
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-phenylpiperazin-1-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
pH 7.5, temperature not specified in the publication
0.0059 - 0.045
adenosine
-
pH 7.4, 37ºC, at variable AMP and Mg2+ concentrations
0.14
AMP
-
pH 7.4, 37ºC, at variable adenosine and saturating MgATP2- concentration
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0075
(+)-6-ethyl-6-[4-[(2,6-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.008
(+/-)-6-ethyl-6-[4-[(2,3,5,6-tetrafluorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.003
(+/-)-6-ethyl-6-[4-[(2,3-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0225
(+/-)-6-ethyl-6-[4-[(2,4-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.01
(+/-)-6-ethyl-6-[4-[(2,4-difluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.014
(+/-)-6-ethyl-6-[4-[(2,5-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.035
(+/-)-6-ethyl-6-[4-[(2,5-dimethoxyphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.02
(+/-)-6-ethyl-6-[4-[(2,6-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0025
(+/-)-6-ethyl-6-[4-[(2-chloro-4-fluorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0012
(+/-)-6-ethyl-6-[4-[(2-chloro-4-iodophenyloxy)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.002
(+/-)-6-ethyl-6-[4-[(2-chloro-4-iodophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.001
(+/-)-6-ethyl-6-[4-[(2-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.005
(+/-)-6-ethyl-6-[4-[(2-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]thiazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0045
(+/-)-6-ethyl-6-[4-[(2-fluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0035
(+/-)-6-ethyl-6-[4-[(2-imidazolylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.003
(+/-)-6-ethyl-6-[4-[(2-methyl-6-chlorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.007
(+/-)-6-ethyl-6-[4-[(2-pyrazylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0045
(+/-)-6-ethyl-6-[4-[(2-pyridylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.007
(+/-)-6-ethyl-6-[4-[(2-pyrimidylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.01
(+/-)-6-ethyl-6-[4-[(3,4-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.011
(+/-)-6-ethyl-6-[4-[(3-chloro-4-fluorophenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0035
(+/-)-6-ethyl-6-[4-[(3-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.004
(+/-)-6-ethyl-6-[4-[(3-fluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0125
(+/-)-6-ethyl-6-[4-[(3-methoxyphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0214
(+/-)-6-ethyl-6-[4-[(3-methylphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0032
(+/-)-6-ethyl-6-[4-[(3-trifluoromethoxyphenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo [1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0025
(+/-)-6-ethyl-6-[4-[(3-trifluoromethylphenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.002
(+/-)-6-ethyl-6-[4-[(4-bromophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.015
(+/-)-6-ethyl-6-[4-[(4-ethynylphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.001
(+/-)-6-ethyl-6-[4-[(4-fluorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0025
(+/-)-6-ethyl-6-[4-[(4-iodophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0022
(+/-)-6-ethyl-6-[4-[(4-iodophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]thiazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.014
(+/-)-6-ethyl-6-[4-[(4-methoxyphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0062
(+/-)-6-ethyl-6-[4-[(4-nitrophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0067
(+/-)-6-ethyl-6-[4-[(4-trifluoromethoxyphenylthio)methyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0012
(+/-)-6-ethyl-6-[4-[(phenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.2
(+/-)-6-ethyl-6-[4-[3-(2-diethylaminoethyl)phenoxymethyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.008
(+/-)-6-ethyl-6-[4-[3-(2-hydroxye)thylphenoxymethyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.15
(+/-)-6-ethyl-6-[4-[3-(2-pyrrolidin-1-ylethyl)phenoxymethyl]-phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.01
(+/-)-6-ethyl-6-[4-[[4-[2-(trimethylsilyl)ethynyl]phenylthio]-methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.002
(+/-)-6-ethyl-6-[4-[[4-[2-(trimethylsilyl)ethynyl]phenylthio]-methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]thiazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0044
(+/-)-6-[4-[(2-chlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.009
(+/-)-6-[4-[(3-trifluoromethylphenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.004
(+/-)-6-[4-[(phenylthio)methyl]phenyl]-6,7-dihydrobenzo-[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.04
(-)-6-ethyl-6-[4-[(2,6-dichlorophenylthio)methyl]phenyl]-6,7-dihydrobenzo[b]pyrrolo[1,2-d][1,4]oxazepin-7-one
Homo sapiens
-
at pH 7.5 and 37°C
0.00224
(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
Homo sapiens
37°C, pH not specified in the publication
0.00014
(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
Homo sapiens
37°C, pH not specified in the publication
0.00538
(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
Homo sapiens
37°C, pH not specified in the publication
0.00334
(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
Homo sapiens
37°C, pH not specified in the publication
0.000114
(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
Homo sapiens
37°C, pH not specified in the publication
0.00601
(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
Homo sapiens
37°C, pH not specified in the publication
0.000088
(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
Homo sapiens
37°C, pH not specified in the publication
0.00011
(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
Homo sapiens
37°C, pH not specified in the publication
0.000115
(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
Homo sapiens
37°C, pH not specified in the publication
0.000048
(1S,2R,3S,5R)-3-amino-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclopentane-1,2-diol
Homo sapiens
37°C, pH not specified in the publication
1
10-(dimethylamino)-6-phenylpyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one
Homo sapiens
-
IC50 above 1 mM, at pH 7.5 and 37°C
0.005
4-(1H-pyrazol-4-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.005 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0013
4-(furan-2-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.01
4-(furan-3-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.01 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0006
4-amino-5-iodo-7-(4'-C-spirocyclopropyl-beta-D-erythropentofuranosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 600 nM
0.000006
4-amino-5-iodo-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]-pyrimidine
Homo sapiens
-
IC50: 6 nM
0.0000053
4-N-(2-methoxyphenyl)amino-5-(4-ethoxyphenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 5.3 nM
0.000001
4-N-(3,4-ethylenedioxyphenyl)amino-5-(2-methylphenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 1 nM
0.000004
4-N-(3,4-ethylenedioxyphenyl)amino-5-phenyl-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 4 nM
0.000002
4-N-(3-ethoxyphenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 2 nM
0.000005
4-N-(4-bromophenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 5 nM
0.000007
4-N-(4-cyanophenyl)amino-5-(4-chlorophenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 7 nM
0.000002
4-N-(4-cyanophenyl)amino-5-(4-ethoxyphenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 2 nM
0.000003
4-N-(4-ethoxyphenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 3 nM
0.00001
4-N-(4-fluorophenyl)amino-5-(3-aminophenyl)-7-(beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 10 nM
0.0000003
4-N-(4-fluorophenyl)amino-5-phenyl-7-(4'-C-spirocyclopropyl-beta-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 0.3 nM
0.000006
4-N-(4-fluorophenyl)amino-5-phenyl-7-(beta-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 6 nM
0.004
4-N-phenylamino-5-phenyl-7-(5'-deoxy-4'-C-methyl-beta-D-ribo-furanosyl)pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 4000 nM
0.000004
4-N-phenylamino-5-phenyl-7-(beta-D-erythro-furanosyl)-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50: 4 nM
0.00004
5-benzyl-6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]pyrimidin-4-amine
Homo sapiens
pH and temperature not specified in the publication
0.0013
5-fluoro-4-(furan-2-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.01
5-fluoro-4-(furan-3-yl)-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.01 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0011
5-fluoro-7-(beta-D-ribofuranosyl)-4-(thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.01
5-fluoro-7-(beta-D-ribofuranosyl)-4-(thiophen-3-yl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.01 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00082
5-iodo-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Homo sapiens
37°C, pH not specified in the publication
0.0008 - 0.0133
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
0.15
6-ethyl-6-(3-methylphenyl)pyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
Homo sapiens
-
at pH 7.5 and 37°C
0.08
6-ethyl-6-(4-methylphenyl)pyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
Homo sapiens
-
at pH 7.5 and 37°C
0.085
6-ethyl-6-phenylpyrrolo[2,1-d][1,5]benzoxazepin-7(6H)-one
Homo sapiens
-
at pH 7.5 and 37°C
0.0012 - 0.0118
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
0.00015
6-indolin-N-yl-8-methylthio-9-(beta-D-ribofuranosyl)-purine
Homo sapiens
-
IC50: 150 nM
0.0012 - 0.061
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
0.0000045
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]-5-(2-phenylethyl)pyrimidin-4-amine
Homo sapiens
pH and temperature not specified in the publication
0.0000025
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]-5-(3-phenylpropyl)pyrimidin-4-amine
Homo sapiens
pH and temperature not specified in the publication
0.000038
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]-5-(4-phenylbutyl)pyrimidin-4-amine
Homo sapiens
pH and temperature not specified in the publication
0.00012
6-[[6-(morpholin-4-yl)pyridin-3-yl]ethynyl]pyrimidin-4-amine hydrate (1:1)
Homo sapiens
pH and temperature not specified in the publication
0.005
7-(beta-D-ribofuranosyl)-4-(1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.005 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.002
7-(beta-D-ribofuranosyl)-4-(thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.002 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.01
7-(beta-D-ribofuranosyl)-4-(thiophen-3-yl)-7H-pyrrolo[2,3-d]pyrimidine
Homo sapiens
-
IC50 above 0.01 mM, in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.001
8-acetylenyl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)-purine
Homo sapiens
-
IC50: 1000 nM
0.0002
8-anilin-N-yl-6-indolin-N-yl-9-(5-deoxy-beta-D-ribofuranosyl)purine
Homo sapiens
-
IC50: 200 nM
0.000019
8-anilin-N-yl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)-purine
Homo sapiens
-
IC50: 19 nM
2900
8-furan-2-yl-6-indolin-N-yl-9-(beta-D-ribofuranosyl)-purine
Homo sapiens
-
IC50: 2900 mM
0.000037
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-benzofuryl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00011
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-furyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00032
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00063
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thiazolyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00086
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thienyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.000083
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thienyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0036
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-furyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0027
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-furyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00097
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-thienyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.00029
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-thienyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0018
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(4-dibenzofuryl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0031
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(4-pyrazolyl)-7 H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Homo sapiens
-
in 50 mM HEPES (pH 6.2), 10 mM KCl, 1 mM MgCl2, temperature not specified in the publication
0.0008
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant Q78A, pH 7.5, 37°C
0.001
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
wild-type, pH 7.5, 37°C
0.003
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant H107A, pH 7.5, 37°C
0.0036
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant Q74A, pH 7.5, 37°C
0.0037
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant K341A, pH 7.5, 37°C
0.0133
6-(4-[[(2-chlorophenyl)sulfanyl]methyl]phenyl)-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant F338A, pH 7.5, 37°C
0.0012
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
wild-type, pH 7.5, 37°C
0.002
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant Q78A, pH 7.5, 37°C
0.0026
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant H107A, pH 7.5, 37°C
0.0035
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant K341A, pH 7.5, 37°C
0.0064
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant Q74A, pH 7.5, 37°C
0.0118
6-ethyl-6-[4-[(phenylsulfanyl)methyl]phenyl]-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant F338A, pH 7.5, 37°C
0.0012
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
wild-type, pH 7.5, 37°C
0.0023
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant Q78A, pH 7.5, 37°C
0.0033
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant H107A, pH 7.5, 37°C
0.0198
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant K341A, pH 7.5, 37°C
0.0203
6-[4-[(2-chloro-4-iodophenoxy)methyl]phenyl]-6-ethyl-6,7-dihydropyrrolo[2,1-d][1,5]benzoxazepine
Homo sapiens
mutant Q74A, pH 7.5, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5 - 9.3
-
about half-maximal activity at pH 5 and pH 9.3, about 80% of maximal activity at pH 6.7, adenosine as substrate
6.5 - 9.3
-
about half-maximal activity at pH 6.5 and pH 9.3, deoxyadenosine as substrate
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
adenosine kinase gene expression is significantly higher in cancer than in normal-appearing tissue
-
T-lymphoblast cell lines MILT 4F, CCRF CEM and RPMI 8402, B-lymphoblast cell lines BALL 1 and EBV (Epstein-Barr-virus)-transformed B-lymphoblast
-
surgically resected human epileptic cortical specimens from Rasmussen encephalitis patients
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug target
adenosine kinase inhibitors raise endogenous adenosine levels, particularly in disease states, and have potential for treatment of seizures, neurodegeneration, and inflammation
malfunction
case report of a patient with adenosine kinase deletion with phenotypes (schizophrenia, parkinsonism, epilepsy) that are predicted when adenosine kinase function is disrupted
physiological function
physiological function
the expression of adenosine kinase in ribavirin-sensitive Orl-8 cells is significantly higher than that in ribavirin-resistant Or-6 cells harboring hepatitis C virus RNA. Ectopic adenosine kinase expression in Or-6 cells converts them from an ribavirin-resistant to an ribavirin-sensitive phenotype, and inhibition of adenosine kinase abolishes the activity of ribavirin. The differential adenosine kinase expression between is not the result of genetic polymorphisms in the adeosine kinase gene promoter region and is not mediated by a microRNA control mechanism. The 5' untranslated region of adenosine kinase messenger RNA in Orl-8 cells is longer than that in OR6 cells, and only a long 5' UTR possesses internal ribosome entry site activity
physiological function
intracellular adenosine, which is controlled by the key molecular regulator adenosine kinase, influences endothelial inflammation and vascular inflammatory diseases
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ADK_HUMAN
362
0
40545
Swiss-Prot
other Location (Reliability: 1)
A0A5F9ZH76_HUMAN
37
0
4214
TrEMBL
other Location (Reliability: 1)
A0A5K1VW54_HUMAN
347
0
38753
TrEMBL
other Location (Reliability: 1)
A0A5F9ZH83_HUMAN
99
0
10901
TrEMBL
other Location (Reliability: 2)
A0A5F9ZH31_HUMAN
294
0
33358
TrEMBL
other Location (Reliability: 1)
A0A140VJE0_HUMAN
345
0
38703
TrEMBL
other Location (Reliability: 2)
A0A5K1VW94_HUMAN
356
0
39959
TrEMBL
other Location (Reliability: 2)
A0A5F9ZGZ8_HUMAN
179
0
20216
TrEMBL
other Location (Reliability: 3)
Q86U79_HUMAN
345
0
38737
TrEMBL
other Location (Reliability: 2)
A0A5F9ZHJ1_HUMAN
270
0
30167
TrEMBL
other Location (Reliability: 2)
A0A5F9ZH72_HUMAN
229
0
25942
TrEMBL
other Location (Reliability: 2)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
monomer
the active form of AK is a monomer, which is composed of an alphabetaalpha sandwich domain and a smaller lid domain
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
structures of complexes of Mycobacterium tuberculosis and human ADKs with 7-ethynyl-7-deazaadenosine show differences in inhibitor interactions in the adenosine binding sites. Inhibitors are readily accommodated into the ATP and adenosine binding sites of Mycobacterium tuberculosis ADK, whereas they bind preferentially into the adenosine site of human ADK
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F338A
mutant displays reduced susceptibility to non-nucleoside inhibitors, while maintaining comparable affinity for nucleoside inhibitors to the wild-type enzyme
H107A
mutant displays reduced susceptibility to non-nucleoside inhibitors, while maintaining comparable affinity for nucleoside inhibitors to the wild-type enzyme
K341A
mutant displays reduced susceptibility to non-nucleoside inhibitors, while maintaining comparable affinity for nucleoside inhibitors to the wild-type enzyme
Q74A
mutant displays reduced susceptibility to non-nucleoside inhibitors, while maintaining comparable affinity for nucleoside inhibitors to the wild-type enzyme
Q74A/F338A
mutant displays reduced susceptibility to non-nucleoside inhibitors, while maintaining comparable affinity for nucleoside inhibitors to the wild-type enzyme
Q78A
mutant displays reduced susceptibility to non-nucleoside inhibitors, while maintaining comparable affinity for nucleoside inhibitors to the wild-type enzyme
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
progressive decrease in activity at pH 7.5 and 8.5, no activity at pH 4.5
641083
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
very unstable in dilute solution. Addition of albumin to reaction mixture in dilute enzyme preparations increases activity. MgATP2-, 1 mM, adenosine 5 mM, and 20% glycerol stabilize on a short term basis at 4ºC. Repeated freeze-thawing inactivates dilute enzyme solutions
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, glycerol, dithiothreitol and adenosine stabilize. 20% glycerol, t1/2 20 days, 75% loss of activity within 60 days. Without glycerol, t1/2 3 days. -70°C to 4°C, 0.01 mg protein/ml, 75 to 95% loss of activity within days
-
4ºC, dithiothreitol or high concentration of salt, stable. Rapid loss of activity at 4ºC with low concentration of salt, recovered when redialyzed against dithiothreitol
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate fractionation, affinity chromatography, gel filtration and chromatography on DEAE-cellulose
-
chromatography on CM-cellulose, chromatography on DEAE-Sephacel and affinity chromatography
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
-
ADK has emerged as a novel target to predict and to prevent epileptogenesis. High levels of ADK expression (e.g. as a long-term consequence of traumatic brain injury) are expected to be predictive for subsequent epileptogenesis. This means that the determination of ADK expression levels in brain, e.g. by using ADK-selective PET or SPECT ligands, has high diagnostic value. On the other hand, prevention of epileptogenesis by focal reconstitution of the adenosine system is an important therapeutic goal
medicine
-
lentiviral expression of anti-adenosine kinase miRNA constitutes a versatile tool to generate therapeutically effective adenosine releasing mesenchymal stem cells, thus representing a model system to generate patient identical autologous adult stem cell grafts
medicine
-
upregulation of adenosine kinase is a common pathologic hallmark of Rasmussen encephalitis. Focal astrogliosis and marked expression of adenosine kinase are observed in the lesions of Rasmussen encephalitis. Significantly greater adenosine kinase expression in Rasmussen encephalitis versus controls and greater enzymatic activity for adenosine kinase are found
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yamada, Y.; Goto, H.; Ogasawara, N.
Purine nucleoside kinases in human T- and B-lymphoblasts
Biochim. Biophys. Acta
761
34-40
1983
Homo sapiens
Hawkins, C.F.; Bagnara, A.S.
Adenosine kinase from human erythrocytes: kinetic studies and characterization of adenosine binding sites
Biochemistry
26
1982-1987
1987
Homo sapiens
Andres, C.M.; Fox, I.H.
Purification and properties of human placental adenosine kinase
J. Biol. Chem.
254
11388-11393
1979
Homo sapiens
Palella, T.D.; Andres, C.M.; Fox, I.H.
Human placental adenosine kinase. Kinetic mechanism and inhibition
J. Biol. Chem.
255
5264-5269
1980
Homo sapiens
Yamada, Y.; Goto, H.; Ogasawara, N.
Adenosine kinase from human liver
Biochim. Biophys. Acta
660
36-43
1981
Homo sapiens
Bone, R.; Cheng, Y.C.; Wolfenden, R.
Inhibition of adenosine and thymidylate kinases by bisubstrate analogs
J. Biol. Chem.
261
16410-16413
1986
Homo sapiens
Carson, D.A.; Kaye, J.; Seegmiller, J.E.
Lymphospecific toxicity in adenosine deaminase deficiency and purine nucleoside phosphorylase deficiency: possible role of nucleoside kinase(s)
Proc. Natl. Acad. Sci. USA
74
5677-5681
1977
Homo sapiens
Mathews, I.I.; Erion, M.D.; Ealick, S.E.
Structure of human adenosine kinase at 1.5.ANG. resolution
Biochemistry
37
15607-15620
1998
Homo sapiens (P55263), Homo sapiens
Long, M.C.; Parker, W.B.
Structure-activity relationship for nucleoside analogs as inhibitors or substrates of adenosine kinase from Mycobacterium tuberculosis. I. Modifications to the adenine moiety
Biochem. Pharmacol.
71
1671-1682
2006
Homo sapiens, Mycobacterium tuberculosis
Kumarapperuma, S.C.; Sun, Y.; Jeselnik, M.; Chung, K.; Parker, W.B.; Jonsson, C.B.; Arterburn, J.B.
Structural effects on the phosphorylation of 3-substituted 1-beta-D-ribofuranosyl-1,2,4-triazoles by human adenosine kinase
Bioorg. Med. Chem. Lett.
17
3203-3207
2007
Homo sapiens
Long, M.C.; Allan, P.W.; Luo, M.Z.; Liu, M.C.; Sartorelli, A.C.; Parker, W.B.
Evaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth
J. Antimicrob. Chemother.
59
118-121
2007
Homo sapiens, Mycobacterium tuberculosis
Bookser, B.C.; Matelich, M.C.; Ollis, K.; Ugarkar, B.G.
Adenosine kinase inhibitors. 4. 6,8-disubstituted purine nucleoside derivatives. Synthesis, conformation, and enzyme inhibition
J. Med. Chem.
48
3389-3399
2005
Homo sapiens
Boyer, S.H.; Ugarkar, B.G.; Solbach, J.; Kopcho, J.; Matelich, M.C.; Ollis, K.; Gomez-Galeno, J.E.; Mendonca, R.; Tsuchiya, M.; Nagahisa, A.; Nakane, M.; Wiesner, J.B.; Erion, M.D.
Adenosine kinase inhibitors. 5. Synthesis, enzyme inhibition, and analgesic activity of diaryl-erythro-furanosyltubercidin analogues
J. Med. Chem.
48
6430-6441
2005
Homo sapiens
Park, J.; Vaidyanathan, G.; Singh, B.; Gupta, R.S.
Identification and biochemical studies on novel non-nucleoside inhibitors of the enzyme adenosine kinase
Protein J.
26
203-212
2007
Homo sapiens
Long, M.C.; Shaddix, S.C.; Moukha-Chafiq, O.; Maddry, J.A.; Nagy, L.; Parker, W.B.
Structure-activity relationship for adenosine kinase from Mycobacterium tuberculosis II. Modifications to the ribofuranosyl moiety
Biochem. Pharmacol.
75
1588-1600
2008
Homo sapiens, Mycobacterium tuberculosis (P9WID5), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WID5)
Caballero, J.; Fernandez, M.; Gonzalez-Nilo, F.D.
A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues
Bioorg. Med. Chem.
16
5103-5108
2008
Homo sapiens
Morote-Garcia, J.C.; Rosenberger, P.; Kuhlicke, J.; Eltzschig, H.K.
HIF-1-dependent repression of adenosine kinase attenuates hypoxia-induced vascular leak
Blood
111
5571-5580
2008
Homo sapiens
Park, J.; Gupta, R.S.
Adenosine kinase and ribokinase - the RK family of proteins
Cell. Mol. Life Sci.
65
2875-2896
2008
Arabidopsis thaliana, Saccharomyces cerevisiae, Caenorhabditis elegans, Drosophila melanogaster, Leishmania donovani, Schizosaccharomyces pombe, Spinacia oleracea, Trypanosoma brucei, Homo sapiens (P55263)
Ren, G.; Li, T.; Lan, J.Q.; Wilz, A.; Simon, R.P.; Boison, D.
Lentiviral RNAi-induced downregulation of adenosine kinase in human mesenchymal stem cell grafts: a novel perspective for seizure control
Exp. Neurol.
208
26-37
2007
Homo sapiens
Giglioni, S.; Leoncini, R.; Aceto, E.; Chessa, A.; Civitelli, S.; Bernini, A.; Tanzini, G.; Carraro, F.; Pucci, A.; Vannoni, D.
Adenosine kinase gene expression in human colorectal cancer
Nucleosides Nucleotides Nucleic Acids
27
750-754
2008
Homo sapiens
Boison, D.
The adenosine kinase hypothesis of epileptogenesis
Prog. Neurobiol.
84
249-262
2008
Homo sapiens
Spacilova, P.; Naus, P.; Pohl, R.; Votruba, I.; Snasel, J.; Zabranska, H.; Pichova, I.; Ameral, R.; Birkus, G.; Cihlar, T.; Hocek, M.
CycloSal-phosphate pronucleotides of cytostatic 6-(Het)aryl-7-deazapurine ribonucleosides: Synthesis, cytostatic activity, and inhibition of adenosine kinases
ChemMedChem
5
1386-1396
2010
Homo sapiens, Mycobacterium tuberculosis
Dong, L.; Shi, J.; Wang, J.; Liu, Y.
Theoretical studies on the conformational change of adenosine kinase induced by inhibitors
Int. J. Quantum Chem.
111
3980-3990
2011
Homo sapiens (P55263)
-
Butini, S.; Gemma, S.; Brindisi, M.; Borrelli, G.; Lossani, A.; Ponte, A.M.; Torti, A.; Maga, G.; Marinelli, L.; La Pietra, V.; Fiorini, I.; Lamponi, S.; Campiani, G.; Zisterer, D.M.; Nathwani, S.M.; Sartini, S.; La Motta, C.; Da Settimo, F.; Novellino, E.; Focher, F.
Non-nucleoside inhibitors of human adenosine kinase: synthesis, molecular modeling, and biological studies
J. Med. Chem.
54
1401-1420
2011
Homo sapiens
Savi, L.; Brindisi, M.; Alfano, G.; Butini, S.; La Pietra, V.; Novellino, E.; Marinelli, L.; Lossani, A.; Focher, F.; Cavella, C.; Campiani, G.; Gemma, S.
Site-directed mutagenesis of key residues unveiled a novel allosteric site on human adenosine kinase for pyrrolobenzoxa(thia)zepinone non-nucleoside inhibitors
Chem. Biol. Drug Des.
87
112-120
2016
Homo sapiens (P55263), Homo sapiens
Mori, K.; Hiraoka, O.; Ikeda, M.; Ariumi, Y.; Hiramoto, A.; Wataya, Y.; Kato, N.
Adenosine kinase is a key determinant for the anti-HCV activity of ribavirin
Hepatology
58
1236-1244
2013
Homo sapiens (P55263), Homo sapiens
Snasel, J.; Naus, P.; Dostal, J.; Hnizda, A.; Fanfrlik, J.; Brynda, J.; Bourderioux, A.; Dusek, M.; Dvorakova, H.; Stolarikova, J.; Zabranska, H.; Pohl, R.; Konecny, P.; Dzubak, P.; Votruba, I.; Hajduch, M.; Rezacova, P.; Veverka, V.; Hocek, M.; Pichova, I.
Structural basis for inhibition of mycobacterial and human adenosine kinase by 7-substituted 7-(het)aryl-7-deazaadenine ribonucleosides
J. Med. Chem.
57
8268-8279
2014
Homo sapiens (P55263), Homo sapiens, Mycobacterium tuberculosis (P9WID5), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WID5)
Luan, G.; Gao, Q.; Guan, Y.; Zhai, F.; Zhou, J.; Liu, C.; Chen, Y.; Yao, K.; Qi, X.; Li, T.
Upregulation of adenosine kinase in Rasmussen encephalitis
J. Neuropathol. Exp. Neurol.
72
1000-1008
2013
Homo sapiens
Kimura, H.; Kushima, I.; Yohimi, A.; Aleksic, B.; Ozaki, N.
Copy number variant in the region of adenosine kinase (ADK) and its possible contribution to schizophrenia susceptibility
Int. J. Neuropsychopharmacol.
21
405-409
2018
Homo sapiens (P55263), Homo sapiens
Toti, K.S.; Osborne, D.; Ciancetta, A.; Boison, D.; Jacobson, K.A.
South (S)- and north (N)-methanocarba-7-deazaadenosine analogues as inhibitors of human adenosine kinase
J. Med. Chem.
59
6860-6877
2016
Homo sapiens (P55263), Homo sapiens
Crespo, R.A.; Dang, Q.; Zhou, N.E.; Guthrie, L.M.; Snavely, T.C.; Dong, W.; Loesch, K.A.; Suzuki, T.; You, L.; Wang, W.; OMalley, T.; Parish, T.; Olsen, D.B.; Sacchettini, J.C.
Structure-guided drug design of 6-substituted adenosine snalogues as potent inhibitors of Mycobacterium tuberculosis adenosine kinase
J. Med. Chem.
62
4483-4499
2019
Homo sapiens (P55263), Homo sapiens, Mycobacterium tuberculosis (P9WID5), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WID5)
Xu, Y.; Wang, Y.; Yan, S.; Yang, Q.; Zhou, Y.; Zeng, X.; Liu, Z.; An, X.; Toque, H.A.; Dong, Z.; Jiang, X.; Fulton, D.J.; Weintraub, N.L.; Li, Q.; Bagi, Z.; Hong, M.; Boison, D.; Wu, C.; Huo, Y.
Regulation of endothelial intracellular adenosine via adenosine kinase epigenetically modulates vascular inflammation
Nat. Commun.
8
943
2017
Homo sapiens (P55263)
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