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Information on EC 2.7.1.20 - adenosine kinase and Organism(s) Mycobacterium tuberculosis and UniProt Accession A5U4N0

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EC Tree
IUBMB Comments
2-Aminoadenosine can also act as acceptor.
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Select one or more organisms in this record: ?
This record set is specific for:
Mycobacterium tuberculosis
UNIPROT: A5U4N0
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The taxonomic range for the selected organisms is: Mycobacterium tuberculosis
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Reaction Schemes
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ATP
+
adenosine
=
ADP
+
AMP
+
=
+
Synonyms
adenosine kinase, adk, ado kinase, adk-l, adk-s, rv2202c, atp:adenosine 5'-phosphotransferase, ldadk, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
adenosine kinase (phosphorylating)
-
-
-
-
Ado kinase
kinase, adenosine (phosphorylating)
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phospho group transfer
-
-
-
-
PATHWAY SOURCE
PATHWAYS
-
-
SYSTEMATIC NAME
IUBMB Comments
ATP:adenosine 5'-phosphotransferase
2-Aminoadenosine can also act as acceptor.
CAS REGISTRY NUMBER
COMMENTARY hide
9027-72-9
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
ATP + 2-methyladenosine
ADP + 2-methyl-AMP
show the reaction diagram
ATP + adenosine
ADP + AMP
show the reaction diagram
dGTP + adenosine
dGDP + AMP
show the reaction diagram
4.7fold higher activity compared to ATP
-
-
?
GTP + adenosine
GDP + AMP
show the reaction diagram
2.5fold higher activity compared to ATP
-
-
?
ATP + 2'-deoxy-2,2'-difluoro-adenosine
ADP + 2'-deoxy-2,2'-difluoro-AMP
show the reaction diagram
0.5% of the activity with adenosine
-
-
?
ATP + 2'-deoxy-adenosine
ADP + 2'-deoxy-AMP
show the reaction diagram
0.3% of the activity with adenosine
-
-
?
ATP + 2,3-difluoro-3-deaza-7-iso-adenosine
ADP + 2,3-difluoro-3-deaza-7-iso-AMP
show the reaction diagram
-
0.03% of the activity with adenosine
-
-
?
ATP + 2,3-difluoro-3-deaza-7-isoadenosine
ADP + 2,3-difluoro-3-deaza-7-isoadenosine 5'-phosphate
show the reaction diagram
-
specific activity1 1 nM/mg/min
-
-
?
ATP + 2,3-difluoro-3-deaza-adenosine
ADP + 2,3-difluoro-3-deaza-AMP
show the reaction diagram
-
2.2% of the activity with adenosine
-
-
?
ATP + 2,3-difluoro-3-deazaadenosine
ADP + 2,3-difluoro-3-deazaadenosine 5'-phosphate
show the reaction diagram
-
specific activity 81 nM/mg/min
-
-
?
ATP + 2-amino-carbocyclic-adenosine
ADP + 2-amino-carbocyclic-AMP
show the reaction diagram
0.4% of the activity with adenosine
-
-
?
ATP + 2-azaadenosine
ADP + 2-azaadenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 2-chloro-adenosine
ADP + 2-chloro-AMP
show the reaction diagram
11.5% of the activity with adenosine
-
-
?
ATP + 2-chloroadenosine
ADP + 2-chloroadenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 2-fluoro-3-deaza-adenosine
ADP + 2-fluoro-3-deaza-AMP
show the reaction diagram
-
1.7% of the activity with adenosine
-
-
?
ATP + 2-fluoro-3-deazaadenosine
ADP + 2-fluoro-3-deazaadenosine 5'-phosphate
show the reaction diagram
-
specific activity 63 nM/mg/min
-
-
?
ATP + 2-fluoro-9-[beta-D-arabinofuranosyl]-adenine
ADP + 2-fluoro-9-[beta-D-arabinofuranosyl]-AMP
show the reaction diagram
0.9% of the activity with adenosine
-
-
?
ATP + 2-fluoro-adenosine
ADP + 2-fluoro-AMP
show the reaction diagram
52% of the activity with adenosine
-
-
?
ATP + 2-fluoroadenosine
ADP + 2-fluoroadenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 2-methyl-adenosine
ADP + 2-methyl-AMP
show the reaction diagram
2% of the activity with adenosine
-
-
?
ATP + 3-deazaadenosine
ADP + 3-deaza-AMP
show the reaction diagram
-
0.03% of the activity with adenosine
-
-
?
ATP + 3-deazaadenosine
ADP + 3-deazaadenosine 5'-phosphate
show the reaction diagram
-
specific activity 1 nM/mg/min
-
-
?
ATP + 3-fluoro-3-deaza-adenosine
ADP + 3-fluoro-3-deaza-AMP
show the reaction diagram
-
0.4% of the activity with adenosine
-
-
?
ATP + 3-fluoro-3-deazaadenosine
ADP + 3-fluoro-3-deazaadenosine 5'-phosphate
show the reaction diagram
-
specific activity 16 nM/mg/min
-
-
?
ATP + 3-[beta-D-ribofuranosyl]-adenine
ADP + 3-[beta-D-ribofuranosyl]-AMP
show the reaction diagram
0.7% of the activity with adenosine
-
-
?
ATP + 6-methyl-purine riboside
ADP + 6-methylpurine-D-riboside 5'-phosphate
show the reaction diagram
2.75% of the activity with adenosine
-
-
?
ATP + 8-aza-9-deazaadenosine
ADP + 8-aza-9-deazaadenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 8-aza-adenosine
ADP + 8-aza-AMP
show the reaction diagram
4% of the activity with adenosine
-
-
?
ATP + 8-aza-carbocyclic-adenosine
ADP + 8-aza-carbocyclic-AMP
show the reaction diagram
4% of the activity with adenosine
-
-
?
ATP + 9-[alpha-L-lyxofuranosyl]-2-fluoro-adenine
ADP + 9-[alpha-L-lyxofuranosyl]-2-fluoro-AMP
show the reaction diagram
3.3% of the activity with adenosine
-
-
?
ATP + 9-[alpha-L-lyxofuranosyl]-adenine
ADP + 9-[alpha-L-lyxofuranosyl]-AMP
show the reaction diagram
3.8% of the activity with adenosine
-
-
?
ATP + 9-[beta-D-5-methyl-(allo)-ribofuranosyl]-2-fluoro-adenine
ADP + 9-[beta-D-5-methyl-(allo)-ribofuranosyl]-2-fluoro-AMP
show the reaction diagram
0.1% of the activity with adenosine
-
-
?
ATP + 9-[beta-D-arabinofuranosyl]-adenine
ADP + 9-[beta-D-arabinofuranosyl]-adenine 5'-phosphate
show the reaction diagram
0.6% of the activity with adenosine
-
-
?
ATP + adenosine
ADP + AMP
show the reaction diagram
ATP + aristeromycin
ADP + aristeromycin 5'-phosphate
show the reaction diagram
37.5% of the activity with adenosine
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
ATP + 2-methyladenosine
ADP + 2-methyl-AMP
show the reaction diagram
activation of 2-mehyladenosine
-
-
?
ATP + adenosine
ADP + AMP
show the reaction diagram
purine salvage enzyme
-
-
?
ATP + adenosine
ADP + AMP
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
dependent on, optimal at 10-50 mM MgCl2, inhibitory above 50 mM
additional information
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
adenosine
substrate inhibition above 0.005 mM, 25% inhibition at 0.025 mM
iodotubercidin
competitive
Mg2+
dependent on, optimal at 10-50 mM MgCl2, inhibitory above 50 mM
(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
-
(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
1-(4-fluorobenzyloxy)-adenosine
-
0.1 mM, 10-90% inhibition
1-deaza-2-amino-6-chloropurine riboside
-
0.1 mM, 10-90% inhibition
2',3',5'-tri-O-acetyl-adenosine
10-90% inhibition at 0.1 mM
2'-deoxy-2,2'-difluoro-adenosine
10-90% inhibition at 0.1 mM
2'-deoxy-adenosine
10-90% inhibition at 0.1 mM
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
-
0.1 mM, 4% inhibition
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
-
0.001 mM, 10-90% inhibition
2-azidoadenosine
-
0.01 mM, 10-90% inhibition
2-bromoadenosine
-
0.01 mM, 10-90% inhibition
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-methoxypurine riboside
-
0.01 mM, 10-90% inhibition
2-chloro-adenosine
10-90% inhibition at 0.01 mM
2-chloroadenosine
-
0.01 mM, 10-90% inhibition
2-chloropurine riboside
-
0.1 mM, 10-90% inhibition
2-ethyladenosine
-
0.1 mM, 10-90% inhibition
2-fluoro-3-deaza-adenosine
-
0.1 mM, 16% inhibition
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-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
10-90% inhibition at 0.001 mM, competitive inhibitor
2-fluoroadenosine
-
0.001 mM, 10-90% inhibition
2-hydroxyadenosine
-
0.1 mM, 10-90% inhibition
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
3-chloro-3-deaza-adenosine
-
0.1 mM, 71% inhibition
3-chloro-3-deazaadenosine
-
0.1 mM, 71% inhibition of phosphorylation of adenosine
3-deazaadenosine
-
0.1 mM, 10-90% inhibition
3-[beta-D-ribofuranosyl]-adenine
10-90% inhibition at 0.01 mM
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
-
-
5'-amino-5'-deoxy-adenosine
10-90% inhibition at 0.001 mM, competitive inhibitor
5'-carboxamido-adenosine
10-90% inhibition at 0.1 mM
5'-deoxy-adenosine
10-90% inhibition at 0.01 mM
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
-
-
6-benzylmercaptopurine riboside
-
0.001 mM, 10-90% inhibition
6-bromopurine riboside
-
0.01 mM, 10-90% inhibition
6-Chloropurine riboside
-
0.01 mM, 10-90% inhibition
6-cyclopentyloxypurine riboside
-
0.001 mM, 10-90% inhibition
6-fluoro-8-aminopurine riboside
-
0.1 mM, 10-90% inhibition
6-fluoromethylpurine riboside
-
0.01 mM, 10-90% inhibition
6-iodopurine riboside
-
0.1 mM, 10-90% inhibition
6-mercaptopurine riboside
-
0.1 mM, 10-90% inhibition
6-methoxypurine riboside
-
0.001 mM, 10-90% inhibition
6-methyl-purine riboside
10-90% inhibition at 0.01 mM
6-Methylmercaptopurine riboside
-
0.001 mM, 10-90% inhibition
6-methylpurine riboside
-
0.01 mM, 10-90% inhibition
6-nitrobenzylmercaptopurine riboside
-
0.001 mM, 10-90% inhibition
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
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-cyano-7-deazaadenosine
-
0.001 mM, 10-90% inhibition
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-iodo-7-deazaadenosine
-
0.001 mM, 10-90% inhibition
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-aminopurine riboside
-
0.1 mM, 10-90% inhibition
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
-
0.01 mM, 10-90% inhibition
8-aza-adenosine
10-90% inhibition at 0.01 mM, competitive inhibitor
8-aza-carbocyclic-adenosine
10-90% inhibition at 0.1 mM
8-azaadenosine
-
0.01 mM, 10-90% 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-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-N1-oxide
-
0.1 mM, 10-90% inhibition
aristeromycin
10-90% inhibition at 0.1 mM
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
-
-
cytidine
-
0.1 mM, 10-90% inhibition
N1-benzyladenosine
-
0.001 mM, 10-90% inhibition
N1-ethyladenosine
-
0.1 mM, 10-90% inhibition
N1-methyladenosine
-
0.001 mM, 10-90% inhibition
N1-oxy-N6-methyladenosine
-
0.1 mM, 10-90% inhibition
N6-aminoadenosine
-
0.1 mM, 10-90% inhibition
uridine
-
0.1 mM, 10-90% 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
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.079 - 0.709
2-methyladenosine
0.0008 - 0.0034
adenosine
1.1
ATP
native enzyme, pH 8.0, 37°C
1.71
adenosine
pH 7.5, temperature not specified in the publication
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00021
iodotubercidin
pH 8.0, 37°C
0.0000275
(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
pH 7.5, temperature not specified in the publication
0.000023
(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
pH 7.5, temperature not specified in the publication
0.0000053
(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
pH 7.5, temperature not specified in the publication
0.000048
(2R,3R,4S,5R)-2-(6-([1,1'-biphenyl]-4-ylethynyl)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
pH 7.5, temperature not specified in the publication
0.0000255
(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
0.0000189
(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
pH 7.5, temperature not specified in the publication
0.0000213
(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
pH 7.5, temperature not specified in the publication
0.000326
(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
0.0000185
(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
pH 7.5, temperature not specified in the publication
0.0000199
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(4-(phenylethynyl)phenyl)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
pH 7.5, temperature not specified in the publication
0.00012
(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
0.0005
2-fluoro-adenosine
-
0.0005
2-fluoroadenosine
-
-
0.0008
5'-amino-5'-deoxy-adenosine
-
0.00015
6-cyclopentyloxypurine riboside
-
-
0.00021
7-iodo-7-deazaadenosine
-
-
0.0000163
7-[4-([1,1'-biphenyl]-4-yl)piperazin-1-yl]-3-beta-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine
pH 7.5, temperature not specified in the publication
0.0058
8-aza-9-deazaadenosine
-
-
0.00019
N1-benzyladenosine
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0088
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diol
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.78
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[4-(1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]tetrahydrofuran-3,4-diol
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0000012
2-fluoro-4-(benzofuran-2-yl)-7-(beta-d-ribofuranosyl)-7H-pyrrolo-[2,3-d]pyrimidine
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0053
7-(2-naphthyl)-7-deazaadenine
Mycobacterium tuberculosis
pH 8.0, 37°C
0.0006
7-(3-dibenzo[b,d]furanyl)-7-deazaadenine
Mycobacterium tuberculosis
pH 8.0, 37°C
0.0014
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-benzofuryl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.004
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-furyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.0047
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.002
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thiazolyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.0024
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thienyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.0037
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(2-thienyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.0039
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-furyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.008
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-furyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.0037
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-thienyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.004
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(3-thienyl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.0065
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(4-dibenzofuryl)-7H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
0.025
cyclo-(3-methylsaligenyl)-beta-D-ribofuranosyl-4-(4-pyrazolyl)-7 H-pyrrolo[2,3-d]pyrimidine-5'-O-phosphate
Mycobacterium tuberculosis
-
IC50 above 0.025 mM, in 50 mM Tris-HCl (pH 8.0), 10 mM KCl, 10 mM MgCl2, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.005
wild-type strain H37Ra
0.1
enzyme in recombinant strain SRICKI
0.36
enzyme in recombinant Mycobacterium smegmatis strain SRI101
0.39
purified native enzyme
0.001
0.016
-
substrate: 3-fluoro-3-deazaadenosine
0.063
-
substrate: 2-fluoro-3-deazaadenosine
0.081
-
substrate: 2,3-difluoro-3-deazaadenosine
3.7
-
substrate: adenosine
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8 - 11
rapid decrease in activity below pH 8.0 and above pH 11.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene Rv2202c or adoK; gene Rv2202c or adoK
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
essential enzyme of Mycobacterium tuberculosis and forms part of the purine salvage pathway within mycobacteria
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
136000
native enzyme, gel filtration
34337
2 * 35000, native enzyme, SDS-PAGE, 2 * 34337, native enzyme, mass spectrometry
35000
2 * 35000, native enzyme, SDS-PAGE, 2 * 34337, native enzyme, mass spectrometry
70000
about, native enzyme, sedimentation equilibrium analysis
74840
native enzyme, light scattering analysis
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
2 * 35000, native enzyme, SDS-PAGE, 2 * 34337, native enzyme, mass spectrometry
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystallized in the presence of adenosine using the vapour-diffusion method. The crystal belongs to space group P3(1)2(1), with unit-cell parameters a = 70.2, c = 111.6 A, and contains a single protein molecule in the asymmetric unit
-
crystals are obtained by either hanging drop or sitting drop vapor diffusion methods. Crystal structure of of ADK unliganded as well as ligand (adenosine) bound at 1.5- and 1.9-A resolution, respectively. The structure of the binary complexes with the inhibitor 2-fluoroadenosine bound and with the adenosine 5'-(beta,gamma-methylene)triphosphate (non-hydrolyzable ATP analog) bound are solved at 1.9-A resolution
hanging drop or sitting drop vapor diffusion methods. Crystal structure of unliganded enzyme as well as adenosine bound enzyme at 1.5 A and 1.9 A resolution, respectively. The structure of the binary complexes with the inhibitor 2-fluoroadenosine bound and with the adenosine 5'-(beta,gamma-methylene)triphosphate bound are solved at 1.9 A resolution
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
vapor diffusion method at 20°C
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, purified native enzyme, 20% glycerol, stable up to 6 months
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
native enzyme 100fold to homogeneity from strain H37Ra
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene Rv2202c or adoK, phylogenetic analysis, subcloning in Escherichia coli strain DH5alpha, overexpression in enzyme-deficient Mycobacterium smegmatis strain SRI101 and in enzyme-deficient Mycobacterium tuberculosis strain SRICKI
overexpressed in Escherichia coli
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
enzyme is a target for drug development in tuberculosis treatment of humans due to the structural and substrate specificity differences of human and mycobacterial enzymes, overview
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Long, M.C.; Escuyer, V.; Parker, W.B.
Identification and characterization of a unique adenosine kinase from Mycobacterium tuberculosis
J. Bacteriol.
185
6548-6555
2003
Mycobacterium tuberculosis (A5U4N0), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Ra / ATCC 25177 (A5U4N0)
Manually annotated by BRENDA team
Wang, Y.; Long, M.C.; Ranganathan, S.; Escuyer, V.; Parker, W.B.; Li, R.
Overexpression, purification and crystallographic analysis of a unique adenosine kinase from Mycobacterium tuberculosis
Acta Crystallogr. Sect. F
F61
553-557
2005
Mycobacterium tuberculosis
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
Reddy, M.C.; Palaninathan, S.K.; Shetty, N.D.; Owen, J.L.; Watson, M.D.; Sacchettini, J.C.
High resolution crystal structures of Mycobacterium tuberculosis adenosine kinase: Insights into the mechanism and specificity of this novel prokaryotic enzyme
J. Biol. Chem.
282
27334-27342
2007
Mycobacterium tuberculosis, Mycobacterium tuberculosis (P9WID5), Mycobacterium tuberculosis H37Rv (P9WID5)
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
Malnuit, V.; Slavetinska, L.P.; Naus, P.; Dzubak, P.; Hajduch, M.; Stolarikova, J.; Snasel, J.; Pichova, I.; Hocek, M.
2-substituted 6-(het)aryl-7-deazapurine ribonucleosides: synthesis, inhibition of adenosine kinases, and antimycobacterial activity
ChemMedChem
10
1079-1093
2015
Mycobacterium tuberculosis, Mycobacterium tuberculosis My 331/88
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team
Perlikova, P.; Konecny, P.; Naus, P.; Snasel, J.; Votruba, I.; Dzubak, P.; Pichova, I.; Hajduch, M.; Hocek, M.
6-Alkyl-, 6-aryl- or 6-hetaryl-7-deazapurine ribonucleosides as inhibitors of human or MTB adenosine kinase and potential antimycobacterial agents
MedChemComm
4
1497-1500
2013
Mycobacterium tuberculosis
-
Manually annotated by BRENDA team
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)
Manually annotated by BRENDA team