Information on EC 2.7.1.20 - adenosine kinase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.7.1.20
-
RECOMMENDED NAME
GeneOntology No.
adenosine kinase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ATP + adenosine = ADP + AMP
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phospho group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
adenine and adenosine salvage VI
-
-
Metabolic pathways
-
-
Purine metabolism
-
-
purine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
ATP:adenosine 5'-phosphotransferase
2-Aminoadenosine can also act as acceptor.
CAS REGISTRY NUMBER
COMMENTARY hide
9027-72-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
guinea pig, male
-
-
Manually annotated by BRENDA team
female
-
-
Manually annotated by BRENDA team
UR6 strain
-
-
Manually annotated by BRENDA team
yellow lupin, var. Popularny
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
male, Wistar strain
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
2 isozymes ADK1 and ADK2
-
-
Manually annotated by BRENDA team
wheat
-
-
Manually annotated by BRENDA team
trypanosomatid flagellate
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
silencing of adenosine kinase leads to impaired root growth, small, crinkled rosette leaves, and reduced apical dominance. ADK-deficient tissues exhibit increased Arabidopsis Response Regulator5 and Arabidopsis Response Regulator7 expression
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
ADP + adenosine
2 AMP
show the reaction diagram
-
47.7% conversion
-
-
?
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
?
show the reaction diagram
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
ATP + 2,3-difluoro-3-deaza-7-isoadenosine
ADP + 2,3-difluoro-3-deaza-7-isoadenosine 5'-phosphate
show the reaction diagram
ATP + 2,3-difluoro-3-deaza-adenosine
ADP + 2,3-difluoro-3-deaza-AMP
show the reaction diagram
ATP + 2,3-difluoro-3-deazaadenosine
ADP + 2,3-difluoro-3-deazaadenosine 5'-phosphate
show the reaction diagram
ATP + 2-(4-benzylpiperazin-1-yl)adenosine
ADP + 2-(4-benzylpiperazin-1-yl)adenosine 5'-phosphate
show the reaction diagram
-
3% of the activity with adenosine
-
-
?
ATP + 2-(pyrrolidin-1-yl)adenosine
ADP + 2-(pyrrolidin-1-yl)adenosine 5'-phosphate
show the reaction diagram
-
53% of the activity with adenosine
-
-
?
ATP + 2-amino-carbocyclic-adenosine
?
show the reaction diagram
-
35.8% of the activity with adenosine
-
-
?
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-benzylaminoadenosine
ADP + 2-benzylaminoadenosine 5'-phosphate
show the reaction diagram
-
4% of the activity with adenosine
-
-
?
ATP + 2-chloro-adenosine
?
show the reaction diagram
-
0.7% of the activity with adenosine
-
-
?
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-cyclohexylaminoadenosine
ADP + 2-cyclohexylaminoadenosine 5'-phosphate
show the reaction diagram
-
3% of the activity with adenosine
-
-
?
ATP + 2-ethylaminoadenosine
ADP + 2-ethylaminoadenosine 5'-phosphate
show the reaction diagram
-
3% of the activity with adenosine
-
-
?
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
?
show the reaction diagram
-
75% 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-isopropylamino-N6-isopropyladenosine
ADP + 2-isopropylamino-N6-isopropyladenosine 5'-phosphate
show the reaction diagram
-
81% of the activity with adenosine
-
-
?
ATP + 2-isopropylaminoadenosine
ADP + 2-isopropylaminoadenosine 5'-phosphate
show the reaction diagram
-
4% of the activity with adenosine
-
-
?
ATP + 2-methyl-adenosine
?
show the reaction diagram
-
0.14% of the activity with adenosine
-
-
?
ATP + 2-methyl-adenosine
ADP + 2-methyl-AMP
show the reaction diagram
-
2% of the activity with adenosine
-
-
?
ATP + 2-methyladenosine
ADP + 2-methyl-AMP
show the reaction diagram
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
ATP + 3-fluoro-3-deazaadenosine
ADP + 3-fluoro-3-deazaadenosine 5'-phosphate
show the reaction diagram
ATP + 3-[beta-D-ribofuranosyl]-adenine
?
show the reaction diagram
-
11.2% of the activity with adenosine
-
-
?
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-bromopurine riboside
ADP + 6-bromopurine riboside 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 6-chloropurine riboside
ADP + 6-chloropurine riboside 5'-phosphate
show the reaction diagram
ATP + 6-fluoromethylpurine riboside
ADP + 6-fluoromethylpurine riboside 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + 6-methyl-purine riboside
?
show the reaction diagram
-
41% 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
?
show the reaction diagram
-
38% of the activity with adenosine
-
-
?
ATP + 8-aza-adenosine
ADP + 8-aza-AMP
show the reaction diagram
-
4% of the activity with adenosine
-
-
?
ATP + 8-aza-carbocyclic-adenosine
?
show the reaction diagram
-
26% 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 + 8-azaadenosine
ADP + 8-azaadenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
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
?
show the reaction diagram
-
15% 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
?
show the reaction diagram
-
0.25% 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 + 9-[beta-D-ribofuranosyl]-purine
ADP + 9-[beta-D-ribofuranosyl]-purine 5'-phosphate
show the reaction diagram
ATP + adenosine
?
show the reaction diagram
the obligate intracellular parasite Toxoplasma gondii is incapable of synthesizing purine nucleotides de novo and relies completely on purines salvaged from the host cells. Adenosine is the preferred precursor and is phosphorylated by adenosine kinase (AK), the most active enzyme in adenosine metabolism in Toxoplasma gondii
-
-
?
ATP + adenosine
ADP + AMP
show the reaction diagram
ATP + adenosine-1-N-oxide
ADP + adenosine-1-N-oxide 5'-phosphate
show the reaction diagram
ATP + adenosine-N1-oxide
ADP + adenosine-N1-oxide 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + ADP
ADP + ATP
show the reaction diagram
-
-
traces of ATP formed
?
ATP + AMP
ADP + ADP
show the reaction diagram
-
-
45% of ADP formed
?
ATP + aristeromycin
?
show the reaction diagram
-
37% of the activity with adenosine
-
-
?
ATP + aristeromycin
ADP + aristeromycin 5'-phosphate
show the reaction diagram
-
37.5% of the activity with adenosine
-
-
?
ATP + cordycepin
ADP + cordycepin 5'-phosphate
show the reaction diagram
ATP + deoxyadenosine
ADP + deoxyadenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + ethenoadenosine
ADP + etheno-AMP
show the reaction diagram
-
-
-
-
?
ATP + fludarabine
ADP + fludarabine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + formycin A
ADP + formycin A 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + inosine
ADP + inosine 5'-phosphate
show the reaction diagram
ATP + N1-oxy-N6-methyladenosine
ADP + N1-oxy-N6-methyladenosine 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + N6-methyladenosine
ADP + N6-methyladenosine 5'-phosphate
show the reaction diagram
ATP + ribavirin
ADP + ribavirin 5'-phosphate
show the reaction diagram
ATP + tubercidin
ADP + tubercidin 5'-phosphate
show the reaction diagram
-
-
-
-
?
ATP + viramidine
ADP + viramidine 5'-phosphate
show the reaction diagram
-
very low activity
-
-
?
CTP + adenosine
CDP + AMP
show the reaction diagram
dADP + adenosine
dAMP + AMP
show the reaction diagram
-
28.5% conversion
-
-
?
dGTP + adenosine
dGDP + AMP
show the reaction diagram
4.7fold higher activity compared to ATP
-
-
?
GDP + adenosine
GMP + AMP
show the reaction diagram
-
21.1% conversion
-
-
?
GTP + adenosine
GDP + AMP
show the reaction diagram
ITP + adenosine
IDP + AMP
show the reaction diagram
TTP + adenosine
TDP + AMP
show the reaction diagram
UDP + adenosine
UMP + AMP
show the reaction diagram
-
5.9% conversion
-
-
?
UTP + adenosine
UDP + AMP
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
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
P9WID5
activation of 2-mehyladenosine
-
-
?
ATP + adenosine
?
show the reaction diagram
Q9TVW2
the obligate intracellular parasite Toxoplasma gondii is incapable of synthesizing purine nucleotides de novo and relies completely on purines salvaged from the host cells. Adenosine is the preferred precursor and is phosphorylated by adenosine kinase (AK), the most active enzyme in adenosine metabolism in Toxoplasma gondii
-
-
?
ATP + adenosine
ADP + AMP
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ATP
ATP:Mg2+ ratio of 4:1; ATP:Mg2+ ratio of 4:1
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MgCl2
-
required
Na+
-
activation
NaF
at 30 mM; at 30 mM; at 30 mM; at 30 mM
Rb+
-
activation, at 100 mM, weaker than K+
additional information
INHIBITORS
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
-
-
(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-(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-[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-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-[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
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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
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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
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0.1 mM, 10-90% inhibition
deoxyadenosine
Deoxycoformycin
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deoxyguanosine
deoxymethylthioadenosine
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weak inhibition
diethylphosphonoacetic acid
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-
dipyridamole
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at low adenosine levels
DTNB
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substrates protect
etidronate
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inhibits adenosine kinase activity in a dose-dependent manner in the presence of 10 mM phosphate
Formycin A
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at very high concentrations, kinetics
GDP
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non competitive with respect to adenosine and competitive with respect to ATP
geminivirus AL2
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geminivirus L2
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guanosine
Hg2+
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strong inhibition, reducing agent reverses
iodotubercidin
K+
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inhibition by increasing concentrations
methylphosphonic acid
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-
MgADP-
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product inhibition, linear, noncompetitive with respect to MgATP2- and adenosine
MgATP2-
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above 1 mM
Mn2+
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strong inhibition above 1 mM
N-(5,6-diphenyl-furo[2,3-d]pyrimidin-4-yl)-propionamide
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40% inhibition at 0.002 mM, 61% inhibition at 0.004 mM, 78% inhibition at 0.01 mM
N-(phosphonomethyl)-glycine
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N-(phosphonomethyl)iminodiacetic acid
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-
N-phosphomethyl glycine
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-
N-phosphomethyl iminodiacetic acid
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-
N1-benzyladenosine
N1-ethyladenosine
N1-methyladenosine
N1-oxy-N6-methyladenosine
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0.1 mM, 10-90% inhibition
N6-aminoadenosine
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0.1 mM, 10-90% inhibition
N6-delta2-isopentenyl-adenosine
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competitive with respect to adenosine
Na+
-
inhibition by increasing concentrations
NH4+
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slight inhibition
NSC 113939
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NSC 113940
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-
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Nucleoside analogs
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overview
Nucleosides
p-hydroxymercuribenzoate
P1,P3-di(adenosine-5')triphosphate
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-
P1,P4-di(adenosine-5')tetraphosphate
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-
P1,P5-di(adenosine-5')pentaphosphate
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Phenylglyoxal
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inhibition levels of wild-type and mutant enzymes, overview
Phosphonoacetic acid
Polyclonal antibodies to adenosine kinase from Leishmania donovani
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not from other eukaryotic sources
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S-adenosylhomocysteine
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97% inhibition
tubercidin
uridine
Xanthosine
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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
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octadecylphosphate prodrug designed as lipophilic derivatives with increased penetration through the mycobacterial cell wall, no antimycobacterial activity
additional information
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