Information on EC 3.5.4.4 - adenosine deaminase

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

EC NUMBER
COMMENTARY hide
3.5.4.4
-
RECOMMENDED NAME
GeneOntology No.
adenosine deaminase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
adenosine + H2O = inosine + NH3
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
amidine hydrolysis
Arthrobacter oxydans
-
-
Deamination
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
adenine and adenosine salvage III
-
-
adenine and adenosine salvage V
-
-
adenosine nucleotides degradation II
-
-
Metabolic pathways
-
-
purine deoxyribonucleosides degradation I
-
-
purine deoxyribonucleosides degradation II
-
-
purine metabolism
-
-
Purine metabolism
-
-
purine ribonucleosides degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
adenosine aminohydrolase
-
CAS REGISTRY NUMBER
COMMENTARY hide
9026-93-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Arthrobacter oxydans
-
-
-
Manually annotated by BRENDA team
strain 0
-
-
Manually annotated by BRENDA team
strain 0
-
-
Manually annotated by BRENDA team
NCIB 8122
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
three enzyme forms ADAI, ADAII and ADAIII
-
-
Manually annotated by BRENDA team
LF 1202
-
-
Manually annotated by BRENDA team
LF 1202
-
-
Manually annotated by BRENDA team
NCIB 8175, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
NCIB 3251, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
Micrococcus candidus
NCIB 8610, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
Micrococcus freudenreichii
ATCC 407, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
ATCC 9341, soluble enzyme, membrane-bound enzyme; NCIB 9278, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
Micrococcus sodonensis
ATCC 11880, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
NC1B 8165, soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
J-326TK
-
-
Manually annotated by BRENDA team
J-326TK
-
-
Manually annotated by BRENDA team
femal Akkaraman sheep, healthy or with chronic fascioliasis
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Pseudomonas iodinum
IFO 3558
-
-
Manually annotated by BRENDA team
this enzyme catalyses the reaction of EC 3.5.4.2 and EC 3.5.4.4; strain 23344c
SwissProt
Manually annotated by BRENDA team
this enzyme catalyses the reaction of EC 3.5.4.2 and EC 3.5.4.4; strain 23344c
SwissProt
Manually annotated by BRENDA team
this enzyme catalyses the reaction of EC 3.5.4.2 and EC 3.5.4.4; wild-type 972 h
SwissProt
Manually annotated by BRENDA team
Staphylococcus aerogenes
soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
soluble enzyme, membrane-bound enzyme
-
-
Manually annotated by BRENDA team
type small, intermediate and large
-
-
Manually annotated by BRENDA team
J-845S
-
-
Manually annotated by BRENDA team
J-845S
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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
2',3'-deoxyadenosine + H2O
2',3'-deoxyinosine + NH3
show the reaction diagram
-
1.7% of the activity with adenosine
-
-
?
2',3'-dideoxyadenosine + H2O
2',3'-dideoxyinosine + NH3
show the reaction diagram
2',3'-isopropylideneadenosine + H2O
2',3'-isopropylideneinosine + NH3
show the reaction diagram
2',3'-O-isopropylidenadenosine + H2O
2',3'-O-isopropylideninosine + NH3
show the reaction diagram
-
modeling studies
-
-
?
2',3'-O-isopropylidene adenosine + H2O
2',3'-O-isopropylidene inosine + NH3
show the reaction diagram
-
-
-
-
?
2',3'-O-methoxymethylideneadenosine + H2O
2',3'-O-methoxymethylideneinosine + NH3
show the reaction diagram
-
modeling studies
-
-
?
2'-dAMP + H2O
2'-dIMP + NH3
show the reaction diagram
-
-
-
-
?
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
show the reaction diagram
2'-deoxyguanosine + H2O
2'-deoxyxanthosine + NH3
show the reaction diagram
-
ADAII shows 41% of the activity with adenosine
-
-
?
2,6-diaminopurine arabinoside + H2O
arabinoguanosine + NH3
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
2,6-diaminopurine riboside + H2O
guanosine + NH3
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
2,6-diaminopurine-2',3'-dideoxyriboside + H2O
2',3'-dideoxyguanosine + NH3
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
2,6-diaminopurine-2'-deoxyriboside + H2O
2'-deoxyguanosine + NH3
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
2-amino-6-chloropurine riboside + H2O
guanosine + ?
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
2-amino-6-chloropurine riboside + H2O
guanosine + Cl-
show the reaction diagram
Micrococcus sodonensis
-
-
-
?
2-amino-6-methoxypurine riboside + H2O
guanosine + ?
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
3'-deoxyadenosine + H2O
3'-deoxyinosine + NH3
show the reaction diagram
5'-AMP + H2O
5'-IMP + NH3
show the reaction diagram
5'-methylthioadenosine + H2O
5'-methylthioinosine + NH3
show the reaction diagram
6-chloropurine riboside + H2O
inosine + Cl-
show the reaction diagram
6-methoxypurinriboside
?
show the reaction diagram
-
-
-
-
?
6-methylaminopurine ribonucleoside + H2O
inosine + methylamine
show the reaction diagram
-
-
-
-
?
adenine + H2O
? + NH3
show the reaction diagram
-
-
-
?
adenine + H2O
hypoxanthine + NH3
show the reaction diagram
-
ADAII shows 70% of the activity with adenosine
-
-
?
adenine + H2O
purine + NH3
show the reaction diagram
-
-
-
-
?
adenine arabinoside + H2O
inosine arabinoside + NH3
show the reaction diagram
adenosine + H2O
inosine + NH3
show the reaction diagram
adenosine 3'-monophosphate + H2O
inosine 3'-monophosphate + NH3
show the reaction diagram
56% of the activity of adenine
-
-
?
adenosine 3'-phosphate + H2O
inosine 3'-phosphate + NH3
show the reaction diagram
adenosine-3'-monophosphate + H2O
IMP-3'-monophosphate + NH3
show the reaction diagram
ADP + H2O
5'-IDP + NH3
show the reaction diagram
arabinoadenosine + H2O
arabinoinosine + NH3
show the reaction diagram
Arthrobacter oxydans
-
-
-
-
?
ATP + H2O
ITP + NH3
show the reaction diagram
cAMP + H2O
?
show the reaction diagram
-
-
-
-
?
double-stranded RNA + H2O
?
show the reaction diagram
-
-
-
-
?
formycin A + H2O
2-(hydroxymethyl)-5-(1H-pyrazolo[4,3-d]pyrimidin-3-yl)tetrahydrofuran-3,4-diol + NH3
show the reaction diagram
guanine + H2O
xanthine + NH3
show the reaction diagram
-
ADAII shows 47% of the activity with adenosine
-
-
?
guanosine + H2O
xanthosine + NH3
show the reaction diagram
-
ADAII shows 75% of the activity with adenosine
-
-
?
N6-isopentenyladenosine + H2O
?
show the reaction diagram
1.9% of the activity of adenine
-
-
?
N6-isopentenyladenosine + H2O
inosine + 3-methylbut-3-en-1-amine
show the reaction diagram
1.2% of the activity of adenine
-
-
?
viramidine + H2O
ribavirin + NH3
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
2'-deoxyadenosine + H2O
2'-deoxyinosine + NH3
show the reaction diagram
5'-methylthioadenosine + H2O
5'-methylthioinosine + NH3
show the reaction diagram
adenosine + H2O
inosine + NH3
show the reaction diagram
viramidine + H2O
ribavirin + NH3
show the reaction diagram
-
the enzyme catalyzes viramidine deamination to ribavirin in vivo as a prodrug conversion to active drug, pharmacokinetic analysis, overview
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
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
lithium ion
-
-
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-erythro-9-(2-hydroxy-3-nonyl)adenine
specific inhibitor of ADA1
(2S,3R)-3-(6-amino-9H-purin-9-yl)nonan-2-ol
-
-
-
(S)-(-)-epoxydecane
-
-
1,6-Dihydro-6-(hydroxymethyl)purine riboside
-
-
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-(hydroxymethyl)nonyl methanesulfonate
-
-
1-(tert-butyldimethylsilanyloxy)-decan-2-ol
-
-
1-(tert-butyldimethylsilanyloxymethyl)nonyl methanesulfonate
-
-
1-alkyl-3-amino-4-pyrazolecarbonitriles
-
-
1-alkyl-4-aminopyrazolo[3,4d]pyrimidines
-
-
1-benzyl-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
-
1-deaza-erythro-9-(2-hydroxy-3-nonyl)adenine
1-deazaadenosine
1-methyl adenosine
-
-
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)-1-(hydroxymethyl)-3-phenylpropyl]-1H-imidazole-4-carboxamide
-
-
1-[(1R)-2-hydroxy-1-phenylethyl]-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-(5-hexyloxyindol-1-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-acetylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(6-butoxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(6-hexanoylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide
-
-
1-[(R)-4-(6-hexyloxyindol-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',3'-o-isopropyliden adenosine
-
-
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'-deoxycoformycin
2'-deoxyformycin
-
50% inhibition of isozyme ADA2 at 0.09 mM
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
2,6-Diaminopurine
2,6-diaminopurine sulfate
-
-
2-alkyl-4-aminopyrazolo[3,4d]pyrimidines
-
-
2-Amino-4-hydroxypteridine
-
-
2-Aminopurine
2-Deoxycoformycin
-
-
2-mercaptoethanol
-
-
3-amino-1-(2-hydroxy-3-nonyl)4-pyrazolecarbonitrile
-
-
3-amino-1-(2-keto-3-nonyl)4-pyrazolecarbonitrile
-
-
3-amino-1-beta-hydroxyalkyl-4-pyrazolecarbonitriles
-
-
3-deaza-erythro-9-(2-hydroxy-3-nonyl)adenine
3-deazaadenosine
4-acetylamino-2-decylpyrazolo[3,4d]pyrimidine
-
-
4-amino-1-(2-hydroxy-3-nonyl)pyrazolo[3,4d]pyrimidine
-
-
4-amino-1-(beta-D-ribofuranosyl)-3H-imidazo[4,5-d]pyridazin-7-(6H)-one
-
-
4-amino-1-(beta-hydroxyethyl)pyrazolo[3,4d]pyrimidine
-
-
4-amino-1-(beta-hydroxyoctyl)pyrazolo[3,4d]pyrimidine
-
-
4-amino-2-(2-hydroxy-1-decyl)pyrazole[3,4-d]pyrimidine
-
i.e. APP
4-amino-2-decyl-6-phenylpyrazolo[3,4d]pyrimidine
-
-
4-amino-5-imidazole carboxamide-HCl
-
-
4-amino-5-imidazole carboxyamide ribonucleoside
-
-
-
4-aminopyridine
-
competitive inhibition
4-aminopyrimidine
-
competitive inhibition
4-fluoro-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
-
4-hydroxypyridine
-
competitive inhibition
4-methoxy-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
-
5'-methylthio-2'-deoxycoformycin
-
-
5'-methylthiocoformycin
5-(beta-D-ribofuranosyl)-1H,5H-imidazo[4,5-b]pyrazolo[3,4-e]pyridine
-
25% inhibition at 0.4 mM
5-carbamimidoyl-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carbohydrazide
-
-
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-Chloropurine
-
-
6-fluoro-D,L-tryptophan
-
adenosine analogue, induces conformational changes inhibiting the enzyme, structural mechanism, overview
6-methylamino riboside
6-Methylmercaptopurine riboside
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-amino-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
-
-
7-chloro-5-methyl-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridin-6-amine
-
15% inhibition at 0.4 mM
-
8-Bromoadenosine
-
-
8-butoxy-7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
-
9-(p-aminobenzyl)adenine
-
-
acetaminophen
-
competitive at 27C, uncompetitive at 37C
Acetylsalicylic acid
-
-
adenine
adenosine analogs
-
-
-
adenosine analogues
-
induce conformational changes inhibiting the enzyme, structural mechanism, overview
-
adenosine monosulfate
-
-
aminoxyacetic acid
Micrococcus sodonensis
-
-
aspirin
-
significantly decreases adenosine deaminase activity, the half-life of adenosine will be lengthened as a consequence of decreased adenosine deaminase activity
aza adenosine analogues
-
-
-
Ba2+
-
44% inhibition at 5 mM
basic histone proteins
-
-
-
caffeic acid phenethyl ester
-
reduces the enzyme activity in vivo, suppresses the induction of the enzyme by cisplatin in vivo
Caffeine
-
-
coformycin
cordycepin
corticosterone
D-coformycin
deaza adenosine analogues
-
-
-
Deoxycoformycin
diclofenac
-
competitive at 27C, uncompetitive at 37C
diethyl dicarbonate
-
-
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
erythro-9-(2-hydroxy-3-nonyl)-3-deazaadenine
-
-
erythro-9-(2-hydroxy-3-nonyl)-adenine
erythro-9-(2-hydroxy-3-nonyl)-adenine hydrochloride
erythro-9-(2-hydroxy-3-nonyl)adenine
erythro-9-(2-hydroxy-3-nonyl)adenine hydrochloride
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
guanosine
heparin
-
-
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
IgG
-
anti adenosine deaminase
-
indole-3-acetic acid
-
the plant hormone decreases enzyme activity in hearts, but not in kidney and muscle
Inosine
iodoacetamide
Micrococcus sodonensis
-
-
iodoacetic acid
Iodopurine
-
-
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
L-cysteine
-
-
lysozyme
-
-
-
methanol
-
MD calculations, discussion of effects
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-ethylmaleimide
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
-
-
N6-methyladenosine
-
-
Na2SO4
-
CD spectra of adenosine deaminase and Na2SO4, determination of helix content, MD calculations, discussion of effects
NaCl
-
MD calculations, discussion of effects
nebularine
-
i.e. 9-beta-D-ribofuranosylpurine, competitive inhibitor
o-phenanthroline
p-chloromercuribenzoate
p-chloromercuryphenylsulfonate
-
-
p-hydroxymercuribenzoic acid
-
-
Pb2+
Micrococcus sodonensis
-
-
Pentachlorophenol
-
-
pentostatin
phenylhydrazine
-
competitive inhibition
progesterone
-
progesterone decreases adenosine deaminase levels, adenosine deaminase levels show regional specificity with differences among the cerebral hemispheres, cerebellum, and brainstems structures
purine
-
competitive inhibition
purine riboside
reduced glutathione
-
-
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
Sodium selenate
-
does not alter enzyme activity
spermidine
-
-
Theobromine
-
-
theophylline
thiol reagents
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8-Azaadenine
-
-
adenine
-
-
cisplatin
-
cisplatin intoxification increases the enzyme activity in vivo, supressable by caffeic acid phenethyl ester
dibutyryl-cAMP
Inosine
-
-
N-acetyl-D-glucosamine
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.29
2',3'-isopropylidene adenosine
-
-
0.004 - 0.56
2'-deoxyadenosine
0.0044 - 0.115
5'-methylthioadenosine
0.31
6-Chloropurine riboside
-
-
0.277
6-chloropurinriboside
-
-
0.081
6-methoxypurinriboside
-
-
0.000023 - 6.6
adenosine
2
Adenosine-3'-monophosphate
-
-
0.17
AMP
-
-
0.5
cAMP
-
-
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.13 - 5.8
5'-methylthioadenosine
0.005 - 180
adenosine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14 - 79
5'-methylthioadenosine
30 - 2900
adenosine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0009 - 0.0019
(2S,3R)-3-(6-amino-9H-purin-9-yl)nonan-2-ol
0.00186
1-(4-benzylphenyl)-3-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]urea
-
30C, 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
-
30C, 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
-
30C, 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
-
30C, pH 7.14
0.0004 - 0.0012
1-deaza-erythro-9-(2-hydroxy-3-nonyl)adenine
0.0016 - 0.0074
1-deazaadenosine
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
-
-
0.059
1-[(1R)-1-(hydroxymethyl)-3-phenylpropyl]-1H-imidazole-4-carboxamide
-
-
0.54
1-[(1R)-2-hydroxy-1-phenylethyl]-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
-
30C, 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
-
30C, pH 7.13
0.0000242
1-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-3-phenylurea
-
30C, 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
-
30C, 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, 25C
0.052
2'-deoxy-7-amino-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
-
pH 7.4, 25C
0.0000034
2'-deoxycoformycin
-
37C, pH not specified in the publication
0.33
2-Aminopurine
-
pH 7.5, 25C
0.000025 - 0.00012
3-deaza-erythro-9-(2-hydroxy-3-nonyl)adenine
0.52 - 1
3-deazaadenosine
0.000066
4-amino-1-(2-hydroxy-3-nonyl)pyrazolo[3,4d]pyrimidine
-
pH 7.2, 30C
0.0106
4-amino-1-(beta-D-ribofuranosyl)-3H-imidazo[4,5-d]pyridazin-7-(6H)-one
-
pH 7.4, 25C
0.00462
4-amino-1-(beta-hydroxyethyl)pyrazolo[3,4d]pyrimidine
-
pH 7.2, 30C
1.8
4-aminopyridine
-
pH 7.5, 25C
1.3
4-aminopyrimidine
-
pH 7.5, 25C
0.0000096
4-fluoro-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
30C, pH 7.4
1.4
4-hydroxypyridine
-
pH 7.5, 25C
0.0001556
4-methoxy-N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
30C, pH 7.3
0.00000079
5'-methylthio-2'-deoxycoformycin
-
-
0.00000043 - 0.029
5'-methylthiocoformycin
0.0265
5-carbamimidoyl-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carbohydrazide
-
pH 7.4, 25C
0.012
7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethyl-8-propoxyimidazo[4,5-e][1,2,4]-triazepine
-
pH 7.0, 25C
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, 25C
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, 25C
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, 25C
0.02
7,8-dihydro-8-ethoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25C
0.03
7,8-dihydro-8-isopropoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25C
0.024
7,8-dihydro-8-methoxy-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25C
0.0514
7-amino-1-(beta-D-ribofuranosyl)-1H-imidazo[4,5-d]pyridazin-4-(5H)-one
-
pH 7.4, 25C
0.015
8-butoxy-7,8-dihydro-1-p-methoxybenzyl-6H-6,7-dimethylimidazo[4,5-e][1,2,4]triazepine
-
pH 7.0, 25C
0.126 - 0.214
acetaminophen
0.0428 - 0.0968
Acetylsalicylic acid
0.17
adenine
-
pH 7.5, 25C
0.00000025
coformycin
-
37C, pH not specified in the publication
0.0000015 - 0.000014
D-coformycin
0.03 - 0.0564
diclofenac
0.00009 - 0.01
diethyl dicarbonate
0.00011 - 0.00014
erythro-9-(2-hydroxy-3-nonyl)-3-deazaadenine
0.00007 - 0.00008
erythro-9-(2-hydroxy-3-nonyl)-adenine
0.00000114 - 0.0005
erythro-9-(2-hydroxy-3-nonyl)adenine
0.35
Inosine
-
pH 7.5, 25C
0.000478
N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-2-phenylacetamide
-
30C, pH 7.6
0.000051
N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]-4-(trifluoromethyl)benzamide
-
30C, pH 7.5
0.0001265
N-[4-[(4-oxo-4,5-dihydro-2H-pyrazolo[3,4-d]pyrimidin-2-yl)methyl]phenyl]benzamide
-
30C, pH 7.2
0.018
N6-methyladenosine
-
25C, 50 mM Tris-HCl buffer, pH 7.4, enzyme concentration 1.5 nM
0.25
phenylhydrazine
-
pH 7.5, 25C
1.1
purine
-
pH 7.5, 25C
0.008 - 0.016
purine riboside
additional information
additional information