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Enzyme Nomenclature
Information on EC 3.5.4.4 - adenosine deaminase
for references in articles please use BRENDA:EC3.5.4.4
Word Map on EC 3.5.4.4
- 3.5.4.4
- purine
- nucleoside
- lymphocyte
- immunodeficiency
- inosine
-
tuberculous
-
deamination
- pleural
-
phosphorylase
- erythrocyte
- effusion
- leukemia
- adenylate
- deoxyadenosine
- 5'-nucleotidase
- ehna
- marrow
- xanthine
-
lymphoid
-
editing
- t-cells
- hypoxanthine
- dipyridamole
- theophylline
- pleurisy
-
lipolysis
-
exudative
- meningitis
-
purinergic
- isoproterenol
- 2-chloroadenosine
- dpcpx
- datp
- ecto-5'-nucleotidase
- s-adenosylhomocysteine
-
transudate
- ectonucleotidases
- pericarditis
- deaminases
- ntpdases
-
n6-cyclopentyladenosine
- deoxycytidine
-
antilipolytic
- deoxyguanosine
- lymphopenia
-
adenosine-induced
-
purinoceptors
- medicine
- empyema
-
acid-fast
- diagnostics
- drug development
-
diphosphohydrolase
- pharmacology
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
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EC NUMBER 
COMMENTARY 
3.5.4.4
-
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RECOMMENDED NAME
GeneOntology No.
adenosine deaminase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
adenosine + H2O = inosine + NH3
-
-
-
-
adenosine + H2O = inosine + NH3
reaction mechanism, structure-function relationship of ADA and dipeptidyl peptidase IV
-
adenosine + H2O = inosine + NH3
reaction mechanism, structure-function relationship of ADA and dipeptidyl peptidase IV
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Deamination
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
adenosine aminohydrolase
-
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CAS REGISTRY NUMBER
COMMENTARY
9026-93-1
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
ATCC 9341, soluble enzyme, membrane-bound enzyme; NCIB 9278, soluble enzyme, membrane-bound enzyme
-
-
this enzyme catalyses the reaction of EC 3.5.4.2 and EC 3.5.4.4; strain 23344c
SwissProt
this enzyme catalyses the reaction of EC 3.5.4.2 and EC 3.5.4.4; wild-type 972 h
SwissProt
-
209604, 209608, 209614, 209635, 654083, 654788, 654832, 656375, 656388, 656467, 667063, 669783, 688040, 696167, 712138
-
-
-
655265, 669618, 670464, 686549, 686745, 687290, 699651, 699959, 699972, 700884, 701182, 718704, 733602, 733674
-
-
CCRF-CEM; expression in Escherichia coli; normal B-cells and T-cell lines MOLT-4; RPMI-8402
-
-
CCRF-CEM; larger enzyme: El, smaller enzyme: Es; normal B-cells and T-cell lines MOLT-4; RPMI-8402
-
-
CCRF-CEM; normal B-cells and T-cell lines MOLT-4; RPMI-8402
-
-
CCRF-CEM; normal B-cells and T-cell lines MOLT-4; RPMI-8402; type 1, 2 and 2-1
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-
CCRF-CEM; normal B-cells and T-cell lines MOLT-4; RPMI-8402; type small, intermediate and large
-
-
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
malfunction
-
apoptosis is enhanced in ADAR1-deficient cells following infection with wild type and V knockout measles virus but not following infection with C knockout measles virus or treatment with tumor necrosis factor-alpha or staurosporine
malfunction
-
disruption of TADA has profound effects on chloroplast translation efficiency, leading to reduced yields of chloroplast-encoded proteins and impaired photosynthetic function
metabolism
-
ADA is a key enzyme in the pathway of hypoxanthine formation
metabolism
-
ADA is a key enzyme in the pathway of hypoxanthine formation
metabolism
-
ADA is a key enzyme in the pathway of hypoxanthine formation
metabolism
-
ADA is a key enzyme in the pathway of hypoxanthine formation
metabolism
the enzyme is involved in the recycling of 5'-deoxyadenosine, whereupon the 5'-deoxyribose moiety of 5'-deoxyinosine is further metabolized to deoxyhexoses used for the biosynthesis of aromatic amino acids in methanogens
metabolism
-
comparison of growth characteristics including intracellular protein levels, RNA content, and nucleotide pool sizes between the extreme halophile Halobacterium halobium and the moderate halophile Haloferax volcanii. The differences in the metabolism of purine bases and nucleosides and the sensitivity to purine analogs between the two halobacteria are reflected in differences in purine enzyme levels
metabolism
-
comparison of growth characteristics including intracellular protein levels, RNA content, and nucleotide pool sizes between the extreme halophile Halobacterium halobium and the moderate halophile Haloferax volcanii. The differences in the metabolism of purine bases and nucleosides and the sensitivity to purine analogs between the two halobacteria are reflected in differences in purine enzyme levels
metabolism
-
the enzyme is involved in the recycling of 5'-deoxyadenosine, whereupon the 5'-deoxyribose moiety of 5'-deoxyinosine is further metabolized to deoxyhexoses used for the biosynthesis of aromatic amino acids in methanogens
-
physiological function
-
ADAR1 is a proviral, antiapoptotic host factor in the context of measles virus infection. ADAR1 enhances the growth of measles virus. ADAR1 suppresses wild type and V knockout measles virus-induced apoptosis. ADAR1 does not protect against tumor necrosis factor-alpha- or staurosporine-induced apoptosis. ADAR1 suppresses wild type and V knockout measles virus-induced protein kinase regulated by RNA activation. ADAR1 suppresses interferon regulatory transcription factor-3 activation by wild type and V knockout measles viruses
physiological function
isozyme ADA1 does not induce T cell-dependent differentiation of monocytes into macrophages; isozyme ADA2 but not ADA1 induces T cell-dependent differentiation of monocytes into macrophages and stimulates macrophage proliferation. ADA2 exhibits a growth factor activity and increases proliferation of CD4+ T cells. ADA2 binds to cells via proteoglycans and adenosine receptors
physiological function
-
ADAR1 deaminase increases exogenous gene expression at the translational level by decreasing protein kinase regulated by RNA-dependent eIF-2alpha phosphorylation
physiological function
-
tRNA adenosine deaminase arginine is a chloroplast tRNA editing protein specifically required for deamination of chloroplast (cp)-tRNAArg(ACG) to cp-tRNAArg(ICG)
physiological function
-
Trypanosoma evansi infection results in either the reduction or increase in the ADA activity in brain of rat. Alterations in ADA activity of the brain in Trypanosoma evansi-infected rats may have implications for pathogenesis of the disease
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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
2',3'-deoxyadenosine + H2O
2',3'-deoxyinosine + NH3
-
1.7% of the activity with adenosine
-
-
?
2',3'-O-isopropylidenadenosine + H2O
2',3'-O-isopropylideninosine + NH3
-
modeling studies
-
-
?
2',3'-O-isopropylidene adenosine + H2O
2',3'-O-isopropylidene inosine + NH3
-
-
-
-
?
2',3'-O-methoxymethylideneadenosine + H2O
2',3'-O-methoxymethylideneinosine + NH3
-
modeling studies
-
-
?
2'-deoxyguanosine + H2O
2'-deoxyxanthosine + NH3
-
ADAII shows 41% of the activity with adenosine
-
-
?
2,6-diaminopurine arabinoside + H2O
arabinoguanosine + NH3
-
-
-
-
?
2,6-diaminopurine-2',3'-dideoxyriboside + H2O
2',3'-dideoxyguanosine + NH3
-
-
-
-
?
2,6-diaminopurine-2'-deoxyriboside + H2O
2'-deoxyguanosine + NH3
-
-
-
-
?
adenine + H2O
hypoxanthine + NH3
-
ADAII shows 70% of the activity with adenosine
-
-
?
adenosine 3'-monophosphate + H2O
inosine 3'-monophosphate + NH3
56% of the activity of adenine
-
-
?
formycin A + H2O
2-(hydroxymethyl)-5-(1H-pyrazolo[4,3-d]pyrimidin-3-yl)tetrahydrofuran-3,4-diol + NH3
guanine + H2O
xanthine + NH3
-
ADAII shows 47% of the activity with adenosine
-
-
?
guanosine + H2O
xanthosine + NH3
-
ADAII shows 75% of the activity with adenosine
-
-
?
N6-isopentenyladenosine + H2O
?
1.9% of the activity of adenine
-
-
?
N6-isopentenyladenosine + H2O
inosine + 3-methylbut-3-en-1-amine
1.2% of the activity of adenine
-
-
?
2',3'-isopropylideneadenosine + H2O
2',3'-isopropylideneinosine + NH3
Micrococcus sodonensis
-
-
-
?
2',3'-isopropylideneadenosine + H2O
2',3'-isopropylideneinosine + NH3
-
-
-
ir
2',3'-isopropylideneadenosine + H2O
2',3'-isopropylideneinosine + NH3
-
-
-
ir
2',3'-isopropylideneadenosine + H2O
2',3'-isopropylideneinosine + NH3
-
-
-
?
2',3'-isopropylideneadenosine + H2O
2',3'-isopropylideneinosine + NH3
-
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
-
ADAII shows 88% of the activity with adenosine
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
-
118.9% of the activity with adenosine
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
-
79.2% of the activity with adenosine
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
-
82.8% of the activity with adenosine
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
-
the enzyme plays an important role in the immune system
-
-
?
3'-deoxyadenosine + H2O
3'-deoxyinosine + NH3
-
2.4% of the activity with adenosine
-
-
?
5'-methylthioadenosine + H2O
5'-methylthioinosine + NH3
-
-
-
-
?
5'-methylthioadenosine + H2O
5'-methylthioinosine + NH3
adenosine deaminase has a secondary function in recycling methylthiopurines from the polyamine biosynthetic pathway
-
-
ir
adenosine + H2O
inosine + NH3
30% of the activity of adenine
-
-
ir
adenosine + H2O
inosine + NH3
-
key enzyme in controlling intra- and extracellular adenosine levels
-
-
?
adenosine + H2O
inosine + NH3
-
-
-
-
?
adenosine + H2O
inosine + NH3
-
-
667870, 668232, 668751, 670393, 670464, 686745, 687290, 697368, 697735, 699651, 699959, 699972, 733602, 733674
-
-
?
adenosine + H2O
inosine + NH3
isozyme ADA2 is important in lymphocyte activation, and may be active in sites of inflammation and during hypoxia and in areas of tumor growth with elevated adenosine levels and acidic pH, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme activity is correlated with the content in malonaldehyde in nasal polyps and nasal mucosa, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme expression and activity is suppressed in normal pregnancy, but not in woman with recurrent spontaneous abortion
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme is involved in differentiation and maturation of the lymphoid system, the enzyme activity is decreased in multiple sclerosis patients irrespective of whether patients have relapsing-remitting or chronic progressive multiple sclerosis, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme plays an important role in the immune system
-
-
?
adenosine + H2O
inosine + NH3
-
metabolization of extracellular adenosine leads to exacerbation of inflammation
-
-
ir
adenosine + H2O
inosine + NH3
-
detailed quantitative structure-activity relationship, QSAR, nonlinear modeling and analysis, descriptor generation and selection, overview
-
-
?
adenosine + H2O
inosine + NH3
-
metabolization of extracellular adenosine
-
-
ir
adenosine + H2O
inosine + NH3
-
adenosine deaminase markedly enhances the agonist and antagonist affinity and abolishes the negative cooperativity on agonist binding to human striatial adenosine A1 receptors
-
-
?
adenosine + H2O
inosine + NH3
-
adenosine deaminase is involved in purine metabolism and is a key enzyme for the control of the cellular levels of adenosine
-
-
?
adenosine + H2O
inosine + NH3
catalytic efficiency of the enzyme for 5'-deoxyadenosine is 1000fold higher than for S-methyl-5'-thioadenosine, and 10000fold hgher than with S-adenosyl-L-homocysteine or adenosine
-
-
?
adenosine + H2O
inosine + NH3
catalytic efficiency of the enzyme for 5'-deoxyadenosine is 1000fold higher than for S-methyl-5'-thioadenosine, and 10000fold hgher than with S-adenosyl-L-homocysteine or adenosine
-
-
?
adenosine + H2O
inosine + NH3
the enzyme is crucial for purine metabolism and normal immune competence
-
-
ir
adenosine + H2O
inosine + NH3
-
the enzyme is important in thymocyte development, especially in late stages, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme is important in thymocyte development, especially in late stages, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme is involved in the bile duct-inflammation and fibrosis caused chronic fascioliasis including an atrophy of the liver parenchyma and liver cirrhosis
-
-
ir
adenosine + H2O
inosine + NH3
-
adenosine deamination is involved in the essential pathway of purine salvage in Plasmodium falciparum, and inhibition of purine salvage results in parasite death
-
-
?
adenosine + H2O
inosine + NH3
-
-
-
-
?
adenosine + H2O
inosine + NH3
1.4% of the activity of adenine
-
-
?
adenosine + H2O
inosine + NH3
2.0% of the activity of adenine
-
-
?
adenosine 3'-phosphate + H2O
inosine 3'-phosphate + NH3
3.3% of the activity of adenine
-
-
?
adenosine 3'-phosphate + H2O
inosine 3'-phosphate + NH3
4.5% of the activity of adenine
-
-
?
adenosine-3'-monophosphate + H2O
IMP-3'-monophosphate + NH3
-
-
-
-
?
formycin A + H2O
2-(hydroxymethyl)-5-(1H-pyrazolo[4,3-d]pyrimidin-3-yl)tetrahydrofuran-3,4-diol + NH3
-
-
-
-
?
formycin A + H2O
2-(hydroxymethyl)-5-(1H-pyrazolo[4,3-d]pyrimidin-3-yl)tetrahydrofuran-3,4-diol + NH3
-
-
-
-
?
viramidine + H2O
ribavirin + NH3
-
the enzyme catalyzes viramidine deamination to ribavirin in vivo as a prodrug conversion to active drug, pharmacokinetic analysis, overview
-
-
?
viramidine + H2O
ribavirin + NH3
-
substrate and product determination by LC-MS
-
-
?
additional information
?
-
-
regulatory role of dipeptidyl peptidase IV on adenosine deaminase activity
-
-
-
additional information
?
-
-
the enzyme may facilitate catalysis via the formation of a stabilizing conformation at the reaction transition state
-
-
-
additional information
?
-
-
the enzyme is bound and complexed by the cell membraneous dipeptidyl peptidase IV, which is identical to the activated immune cell antigen CD26, playing a role in the immune system, overview
-
-
-
additional information
?
-
-
substrate specificities of the large and the small isozyme, overview
-
-
-
additional information
?
-
-
adenosine deaminase inhibition enhances the efficiency of signal transduction and inotropic response mediated by A1 adenosine receptor in hyperthyroid guinea pig atrium via elevated intracellular adenosine levels, overview
-
-
-
additional information
?
-
-
the enzyme is involved in purine metabolism and plays an important role in the mechanism of the immune system
-
-
-
additional information
?
-
-
no activity with 3'-deoxyadenosine, 2',3'-deoxyadenosine and 2'-O-methyladenosine
-
-
-
additional information
?
-
-
activity with 3'-deoxyadenosine, 2',3'-deoxyadenosine and 2'-O-methyladenosine is less than 0.5% of the activity with adenine
-
-
-
additional information
?
-
-
the large isozyme is bound and complexed by the cell membraneous dipeptidyl peptidase IV, which is identical to the activated immune cell antigen CD26, playing a role in the immune system, overview
-
-
-
additional information
?
-
-
substrate specificities of the large and the small isozyme, overview
-
-
-
additional information
?
-
-
Plasmodium gallinaceum ADA does not have significant activity for 5'-methylthioadenosine
-
-
-
additional information
?
-
-
adenosine modulates the immune system and inhibits inflammation via reduction of cytokine biosynthesis and neutrophil functions, enzyme inhibition reduces inflammation in experimental colitis, overview
-
-
-
additional information
?
-
-
ADA is associated with the Galphai-3 protein-coupled A1 receptor
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
viramidine + H2O
ribavirin + NH3
-
the enzyme catalyzes viramidine deamination to ribavirin in vivo as a prodrug conversion to active drug, pharmacokinetic analysis, overview
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
-
the enzyme plays an important role in the immune system
-
-
?
5'-methylthioadenosine + H2O
5'-methylthioinosine + NH3
A5KE01
adenosine deaminase has a secondary function in recycling methylthiopurines from the polyamine biosynthetic pathway
-
-
ir
adenosine + H2O
inosine + NH3
-
key enzyme in controlling intra- and extracellular adenosine levels
-
-
?
adenosine + H2O
inosine + NH3
-
-
-
-
?
adenosine + H2O
inosine + NH3
Q9NZK5
isozyme ADA2 is important in lymphocyte activation, and may be active in sites of inflammation and during hypoxia and in areas of tumor growth with elevated adenosine levels and acidic pH, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme activity is correlated with the content in malonaldehyde in nasal polyps and nasal mucosa, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme expression and activity is suppressed in normal pregnancy, but not in woman with recurrent spontaneous abortion
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme is involved in differentiation and maturation of the lymphoid system, the enzyme activity is decreased in multiple sclerosis patients irrespective of whether patients have relapsing-remitting or chronic progressive multiple sclerosis, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme plays an important role in the immune system
-
-
?
adenosine + H2O
inosine + NH3
-
metabolization of extracellular adenosine leads to exacerbation of inflammation
-
-
ir
adenosine + H2O
inosine + NH3
-
adenosine deaminase is involved in purine metabolism and is a key enzyme for the control of the cellular levels of adenosine
-
-
?
adenosine + H2O
inosine + NH3
P03958
the enzyme is crucial for purine metabolism and normal immune competence
-
-
ir
adenosine + H2O
inosine + NH3
-
the enzyme is important in thymocyte development, especially in late stages, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme is important in thymocyte development, especially in late stages, overview
-
-
?
adenosine + H2O
inosine + NH3
-
the enzyme is involved in the bile duct-inflammation and fibrosis caused chronic fascioliasis including an atrophy of the liver parenchyma and liver cirrhosis
-
-
ir
adenosine + H2O
inosine + NH3
-
adenosine deamination is involved in the essential pathway of purine salvage in Plasmodium falciparum, and inhibition of purine salvage results in parasite death
-
-
?
additional information
?
-
-
regulatory role of dipeptidyl peptidase IV on adenosine deaminase activity
-
-
-
additional information
?
-
-
the enzyme is bound and complexed by the cell membraneous dipeptidyl peptidase IV, which is identical to the activated immune cell antigen CD26, playing a role in the immune system, overview
-
-
-
additional information
?
-
-
adenosine deaminase inhibition enhances the efficiency of signal transduction and inotropic response mediated by A1 adenosine receptor in hyperthyroid guinea pig atrium via elevated intracellular adenosine levels, overview
-
-
-
additional information
?
-
-
the enzyme is involved in purine metabolism and plays an important role in the mechanism of the immune system
-
-
-
additional information
?
-
-
the large isozyme is bound and complexed by the cell membraneous dipeptidyl peptidase IV, which is identical to the activated immune cell antigen CD26, playing a role in the immune system, overview
-
-
-
additional information
?
-
-
adenosine modulates the immune system and inhibits inflammation via reduction of cytokine biosynthesis and neutrophil functions, enzyme inhibition reduces inflammation in experimental colitis, overview
-
-
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
the activity found in the enzymes expressed with added Zn(II) and added Fe(II) are 2fold higher than when expressed with Ni(II) or without additional metal
Fe3+
Mg2+
Ni2+
Zn2+
additional information
Ni2+
the activity found in the enzymes expressed with added Zn(II) and added Fe(II) are 2fold higher than when expressed with Ni(II) or without additional metal
Zn2+
the activity found in the enzymes expressed with added Zn(II) and added Fe(II) are 2fold higher than when expressed with Ni(II) or without additional metal
Zn2+
-
ADA contains a tightly bound Zn2+ which is required for activity, the stability of the protein is decreased significantly in the absence of Zn2+
additional information
-
there are no significant changes in ADA activity in the presence of cadmium acetate, potassium dichromate, lead acetate, zinc chloride, copper sulfate, cobalt chloride, and manganese chloride
additional information
-
metal-dependent enzyme. The metal can not be removed from the enzyme nor can the nature of the catalytic metal be established. Dialysis of the wild-type enzyme for 3 days against a dipicolinic acid containing buffer fails to show any lowering enzyme activity, again indicating that chelation is not able to remove the bound metal in the active site. The catalytic metal is not removed by EDTA
additional information
metal-dependent enzyme. The metal can not be removed from the enzyme nor can the nature of the catalytic metal be established. Dialysis of the wild-type enzyme for 3 days against a dipicolinic acid containing buffer fails to show any lowering enzyme activity, again indicating that chelation is not able to remove the bound metal in the active site. The catalytic metal is not removed by EDTA
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-(4-benzylphenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
-
1-(4-fluorophenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
-
1-(4-methoxyphenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
-
1-benzyl-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
-
1-[(1R)-1-(hydroxymethyl)-3-(6-[[(1-methyl-1H-benzimidazol-2-yl)acetyl]amino]-1H-indol-1-yl)propyl]-1H-imidazole-4-carboxamide
-
-
1-[(1R)-1-(hydroxymethyl)-3-naphthalen-1-ylpropyl]-1H-imidazole-4-carboxamide
-
-
1-[(1R)-3-[6-(acetylamino)-1H-indol-1-yl]-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxamide
-
-
1-[(1R)-3-[6-(hexanoylamino)-1H-indol-1-yl]-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxamide
-
-
1-[(1R,2S)-2-hydroxy-1-(2-naphthalen-1-ylethyl)propyl]-1H-imidazole-4-carboxamide
-
-
1-[(2S,3R)-2,3-dihydroxycyclopentyl]-5-(1,3-thiazol-5-yl)pyrimidine-2,4(1H,3H)-dione
-
28% inhibition at 0.1 mM
1-[(2S,3R)-2,3-dihydroxycyclopentyl]-5-(furan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
35% inhibition at 0.1 mM
1-[(2S,3R)-2,3-dihydroxycyclopentyl]-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione
-
36% inhibition at 0.1 mM
1-[(4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]-5-(1,3-thiazol-5-yl)pyrimidine-2,4(1H,3H)-dione
-
49% inhibition at 0.1 mM
1-[(4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]-5-(furan-2-yl)pyrimidine-2,4(1H,3H)-dione
-
55% inhibition at 0.1 mM
1-[(4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]-5-(thiophen-2-yl)pyrimidine-2,4(1H,3H)-dione
-
48% inhibition at 0.1 mM
1-[(R)-1-hydroxy-4-(1-methyl-5-(3-phenylpropoxy)indol-3-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(5-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(3-(1-methylbenzimidazol-2-yl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(3-(3-pyridyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(3-(4-methylphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(3-phenylpropionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(4-(4-methylphenyl)butyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(4-phenylbutoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(4-phenylbutyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(5-phenylvalerylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-1-hydroxy-4-(6-(6-phenylhexanoylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(5-(3-(4-chlorophenyl)propoxyl)-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(5-hexyloxy-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(6-(3-(4-chlorophenyl)propoxy)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(6-hexanoylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[4-(dimethylamino)phenyl]-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
-
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-(4-phenoxyphenyl)urea
-
-
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-phenylurea
-
-
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea
-
-
2'-deoxy-4-amino-1-(beta-D-ribofuranosyl)-3H-imidazo[4,5-d]pyridazin-7-(6H)-one
-
-
2'-deoxy-7-amino-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
-
-
2,2,2-trifluoro-N-[7-chloro-5-methyl-3-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-yl]-acetamide
-
20% inhibition at 0.4 mM
2,2,2-trifluoro-N-[7-chloro-5-methyl-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-yl]acetamide
-
23% inhibition at 0.4 mM
4-fluoro-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
-
4-methoxy-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
-
5-(beta-D-ribofuranosyl)-1H,5H-imidazo[4,5-b]pyrazolo[3,4-e]pyridine
-
25% inhibition at 0.4 mM
5-methyl-3-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-amine
-
19% inhibition at 0.4 mM
5-methyl-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-amine
-
6% inhibition at 0.4 mM
5-methyl-6-nitro-3-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
-
31% inhibition at 0.4 mM
5-methyl-6-nitro-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
-
25% inhibition at 0.4 mM
6-fluoro-D,L-tryptophan
-
adenosine analogue, induces conformational changes inhibiting the enzyme, structural mechanism, overview
7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethyl-8-propoxyimidazo[4,5-e][1,2,4]-triazepine
-
-
7,8-dihydro-1-p-methoxybenzyl-8-(2-methoxyethoxy)-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
7,8-dihydro-1-p-methoxybenzyl-8-(3-methylbenzyloxy)-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
7,8-dihydro-1-p-methoxybenzyl-8-(4-methoxybenzyloxy)-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
7,8-dihydro-8-ethoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
7,8-dihydro-8-isopropoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
7,8-dihydro-8-methoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
7-(beta-D-ribofuranosyl)-1H,7H-imidazo[4,5-b]pyrazolo[3,4-e]pyridine
-
7% inhibition at 0.4 mM
7-chloro-5-methyl-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-amine
-
15% inhibition at 0.4 mM
8-butoxy-7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
adenosine analogues
-
induce conformational changes inhibiting the enzyme, structural mechanism, overview
-
aspirin
-
significantly decreases adenosine deaminase activity, the half-life of adenosine will be lengthened as a consequence of decreased adenosine deaminase activity
caffeic acid phenethyl ester
-
reduces the enzyme activity in vivo, suppresses the induction of the enzyme by cisplatin in vivo
dodecyltrimethylammonium bromide
-
at low concentrations (approximately 0.1 mM), enzyme activity decreases, it increases at a slightly higher concentration (about 0.2 mM), and finally decreases again (about 0.3 mM), CD spectra of adenosine deaminase and DTAB, determination of helix content, MD calculations
ethanol
-
CD spectra of adenosine deaminase and EtOH, determination of helix content, MD calculations
FR234938
-
i.e. 1-((1R,2S)-2-hydroxy-1-(2-(1-naphthyl)ethyl)propyl)1H-imidazole-4-carboxamine, a non-nucleoside inhibitor, the inhibition is blocked by an A2a adenosine receptor antagonist
HgCl2
-
inhibition of ADA activity is observed in the soluble fraction at 0.005-0.25 mM HgCl2 (84.6-92.6% respectively), whereas inhibition occurs at 0.005-0.25 mM in membrane fractions (20.9-26% respectively). The inhibition is partially or fully abolished by 0.5 mM dithiothreitol or EDTA
indole-3-acetic acid
-
the plant hormone decreases enzyme activity in hearts, but not in kidney and muscle
isosorbide mononitrate
-
significantly decreases adenosine deaminase activity, the half-life of adenosine will be lengthened as a consequence of decreased adenosine deaminase activity
kinetin
-
the plant hormone decreases enzyme activity in hearts, but not in kidney and muscle
methylmercury
-
concentration 0.1, 1.0, 20 M, inhibits adenosine deaminase activity in 7- and 60-day-old rats in a concentration-dependent manner, glutathione (50 microM) and dithiothreitol (50 microM) prevent the reduction of adenosine deaminase activity both in cerebral cortex and hippocampus, garlic alcoholic extract (100 microg/ml) abolishes the reduction of adenosine deaminase
metoprolol
-
significantly decreases adenosine deaminase activity, the half-life of adenosine will be lengthened as a consequence of decreased adenosine deaminase activity
N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-2-phenylacetamide
-
-
N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-4-(trifluoromethyl)benzamide
-
-
N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
-
Na2SO4
-
CD spectra of adenosine deaminase and Na2SO4, determination of helix content, MD calculations, discussion of effects
progesterone
-
progesterone decreases adenosine deaminase levels, adenosine deaminase levels show regional specificity with differences among the cerebral hemispheres, cerebellum, and brainstems structures
simvastatin
-
inhibits ADA1 activity by 46.7%; significantly decreases adenosine deaminase activity, the half-life of adenosine will be lengthened as a consequence of decreased ADA activity
Sodium dodecyl sulfate
-
at low concentrations (approximately 0.1 mM) enzyme activity decreases, it increases at a slightly higher concentration (about 0.4 mM), and finally decreases again (about 0.55 mM), CD spectra of adenosine deaminase and SDS, determination of helix content, MD calculations
2'-deoxycoformycin
-
a natural product transition state analogue inhibitor
5'-methylthiocoformycin
-
specific transition state analogue inhibitor of Plasmodium ADA
5'-methylthiocoformycin
-
specific transition state analogue inhibitor of Plasmodium ADA
5'-methylthiocoformycin
-
specific transition state analogue inhibitor of Plasmodium ADA, 5'-methylthiocoformycin is a subnanomolar inhibitor of Plasmodium falciparum ADA and demonstrates more than 20000fold selectivity relative to human ADA
5'-methylthiocoformycin
-
poor inhibitor of Plasmodium gallinaceum ADA
5'-methylthiocoformycin
-
specific transition state analogue inhibitor of Plasmodium ADA
5'-methylthiocoformycin
-
specific transition state analogue inhibitor of Plasmodium ADA
corticosterone
inhibits the adenosine deaminase activity in an age- and region-specific manner
erythro-9-(2-hydroxy-3-nonyl)-adenine
-
0.1 mM concentration, ADA2 is practically unaffected; 0.1 mM concentration, complete and reversible inhibition
erythro-9-(2-hydroxy-3-nonyl)adenine
-
i.e. EHNA, specific for isozyme ADA1, no inhibition of isozyme ADA2
erythro-9-(2-hydroxy-3-nonyl)adenine
-
ADA-specific inhibitor, almost complete inhibition at 0.00005 mM
pentostatin
-
i.e. (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
purine riboside
-
adenosine analogue, induces conformational changes inhibiting the enzyme, structural mechanism, overview
Zn2+
-
decrease of 31.3% on adenosine deamination in membranes is observed in the presence of 5 mM Zn2+
additional information
-
structure-based design, synthesis, and structure-activity relationship studies of non-nucleoside adenosine deaminase inhibitors, overview
-
additional information
-
molecular dynamic simulations of inhibitor-enzyme interaction, overview
-
additional information
-
no inhibition of the bovine enzyme by 5'-methylthiocoformycin and 5'-methylthio-2'-deoxycoformycin
-
additional information
-
cytotoxic effects of inhibitors against human breast cancer cell lines MCF-7 and MCF-10A
-
additional information
-
the trend of relative activity is directly proportional to helicity and inversely proportional to accessible surface area
-
additional information
-
no inhibition by erythro-9-(2-hydroxy-3-nonyl)-adenine hydrochloride
-
additional information
-
no inhibition of the human enzyme by 5'-methylthiocoformycin and 5'-methylthio-2'-deoxycoformycin
-
additional information
-
loss of activity precedes the global secondary and tertiary structure transition when the enzyme is exposed to denaturant, structural mechanism, overview
-
additional information
-
ADA1 activity is not changed significantly by aspirin, metoprolol, isosorbide mononitrate, and molsidominemolsidomine; molsidomine does not influence plasma adenosine deaminase activity significantly
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cisplatin
-
cisplatin intoxification increases the enzyme activity in vivo, supressable by caffeic acid phenethyl ester
dibutyryl-cAMP
causes a significant increase in the activity level of adenosine deaminase depending on the regions of the gastrointestinal tract
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0044
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.0087
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.0095
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.022
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.115
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.026
adenosine
-
25°C, 50 mM Tris-HCl buffer, pH 7.4, enzyme concentration 1.5 nM
0.032
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.057
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.06
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.072
adenosine
pH and temperature not specified in the publication, mutant enzyme Y136R
0.083
adenosine
-
mutant enzyme D172E, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.087
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.088
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.104
adenosine
-
mutant enzyme D172A, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.12
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.15
adenosine
pH and temperature not specified in the publication, mutant enzyme E150R; pH and temperature not specified in the publication, wild-type enzyme
additional information
additional information
-
kinetics of the large and the small isozyme
-
additional information
additional information
-
kinetics of the large and the small isozyme
-
additional information
additional information
-
isozymes ADA1 and ADA2 are kinetically distinct
-
additional information
additional information
-
optimization of a spectrometric kinetic measurement method pure enzyme, kinetics in presence of substrate, product and inhibtior, overview
-
additional information
additional information
-
optimization of a spectrometric kinetic measurement method using Hut78 cell extract, kinetics in presence of substrate, product and inhibtior, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.13
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.31
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.35
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
0.51
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
5.8
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
1.8
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
1.9
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
4.7
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
5.3
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
5.6
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
6.8
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
12.9
adenosine
-
mutant enzyme D172E, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
14
adenosine
-
mutant enzyme D172A, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
110
adenosine
pH and temperature not specified in the publication, mutant enzyme E150R; pH and temperature not specified in the publication, wild-type enzyme
140
adenosine
pH and temperature not specified in the publication, mutant enzyme Y136R
180
adenosine
-
25°C, 50 mM Tris-HCl buffer, pH 7.4, enzyme concentration 1.5 nM
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
14
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
23
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
36
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
50
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
79
5'-methylthioadenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
30
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
57
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
59
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
61
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
64
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
82
adenosine
-
wild type enzyme, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
130
adenosine
-
mutant enzyme D172A, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
150
adenosine
-
mutant enzyme D172E, in 100 mM Tris-HCl buffer (pH 8.0), temperature not specified in the publication
750
adenosine
pH and temperature not specified in the publication, mutant enzyme E150R; pH and temperature not specified in the publication, wild-type enzyme
2900
adenosine
pH and temperature not specified in the publication, mutant enzyme Y136R
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00186
1-(4-benzylphenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
30°C, pH 7.12
0.0000115
1-(4-fluorophenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
30°C, pH 7.9
0.0002827
1-(4-methoxyphenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
30°C, pH 7.8
0.000857
1-benzyl-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
30°C, pH 7.14
0.000077
1-[(1R)-1-(hydroxymethyl)-3-(6-[[(1-methyl-1H-benzimidazol-2-yl)acetyl]amino]-1H-indol-1-yl)propyl]-1H-imidazole-4-carboxamide
-
-
0.0068
1-[(1R)-1-(hydroxymethyl)-3-naphthalen-1-ylpropyl]-1H-imidazole-4-carboxamide
-
-
0.013
1-[(1R)-3-[6-(acetylamino)-1H-indol-1-yl]-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxamide
-
-
0.00024
1-[(1R)-3-[6-(hexanoylamino)-1H-indol-1-yl]-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxamide
-
-
0.00011
1-[(1R,2S)-2-hydroxy-1-(2-naphthalen-1-ylethyl)propyl]-1H-imidazole-4-carboxamide
-
-
0.000026
1-[(R)-1-hydroxy-4-(1-methyl-5-(3-phenylpropoxy)indol-3-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.0019
1-[(R)-1-hydroxy-4-(5-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000011
1-[(R)-1-hydroxy-4-(6-(3-(1-methylbenzimidazol-2-yl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000017
1-[(R)-1-hydroxy-4-(6-(3-(3-pyridyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000057
1-[(R)-1-hydroxy-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.000038
1-[(R)-1-hydroxy-4-(6-(3-(4-methylphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.00003
1-[(R)-1-hydroxy-4-(6-(3-phenylpropionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000017
1-[(R)-1-hydroxy-4-(6-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000034
1-[(R)-1-hydroxy-4-(6-(4-(4-methylphenyl)butyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000012
1-[(R)-1-hydroxy-4-(6-(4-phenylbutoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000016
1-[(R)-1-hydroxy-4-(6-(4-phenylbutyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.0000077
1-[(R)-1-hydroxy-4-(6-(5-phenylvalerylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.000091
1-[(R)-1-hydroxy-4-(6-(6-phenylhexanoylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
-
-
0.0000049
1-[(R)-4-(5-(3-(4-chlorophenyl)propoxyl)-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.000013
1-[(R)-4-(5-hexyloxy-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.0062
1-[(R)-4-(5-hexyloxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.000013
1-[(R)-4-(6-(3-(4-chlorophenyl)propoxy)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.0000075
1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.0013
1-[(R)-4-(6-acetylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.00024
1-[(R)-4-(6-butoxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.000024
1-[(R)-4-(6-hexanoylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.000055
1-[(R)-4-(6-hexyloxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
0.0000201
1-[4-(dimethylamino)phenyl]-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
30°C, pH 7.11
0.00108
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-(4-phenoxyphenyl)urea
-
30°C, pH 7.13
0.0000242
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-phenylurea
-
30°C, pH 7.7
0.0000016
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea
-
30°C, pH 7.10
0.0121
2'-deoxy-4-amino-1-(beta-D-ribofuranosyl)-3H-imidazo[4,5-d]pyridazin-7-(6H)-one
-
pH 7.4, 25°C
0.052
2'-deoxy-7-amino-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
-
pH 7.4, 25°C
0.0000034
2'-deoxycoformycin
-
37°C, pH not specified in the publication
0.0106
4-amino-1-(beta-D-ribofuranosyl)-3H-imidazo[4,5-d]pyridazin-7-(6H)-one
-
pH 7.4, 25°C
0.0000096
4-fluoro-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
30°C, pH 7.4
0.0001556
4-methoxy-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
30°C, pH 7.3
0.0265
5-carbamimidoyl-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carbohydrazide
-
pH 7.4, 25°C
0.012
7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethyl-8-propoxyimidazo[4,5-e][1,2,4]-triazepine
-
pH 7.0, 25°C
0.023
7,8-dihydro-1-p-methoxybenzyl-8-(2-methoxyethoxy)-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.093
7,8-dihydro-1-p-methoxybenzyl-8-(3-methylbenzyloxy)-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.077
7,8-dihydro-1-p-methoxybenzyl-8-(4-methoxybenzyloxy)-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.02
7,8-dihydro-8-ethoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.03
7,8-dihydro-8-isopropoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.024
7,8-dihydro-8-methoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.0514
7-amino-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
-
pH 7.4, 25°C
0.015
8-butoxy-7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25°C
0.00007 - 0.00008
erythro-9-(2-hydroxy-3-nonyl)-adenine