Information on EC 3.3.1.1 - adenosylhomocysteinase

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

EC NUMBER
COMMENTARY hide
3.3.1.1
-
RECOMMENDED NAME
GeneOntology No.
adenosylhomocysteinase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of thioether
-
-
-
-
synthesis of thioether
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Cysteine and methionine metabolism
-
-
L-methionine degradation I (to L-homocysteine)
-
-
Metabolic pathways
-
-
S-adenosyl-L-methionine cycle II
-
-
methionine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-homocysteine hydrolase
The enzyme contains one tightly bound NAD+ per subunit. This appears to bring about a transient oxidation at C-3' of the 5'-deoxyadenosine residue, thus labilizing the thioether bond [2] (for mechanism, click here), cf. EC 5.5.1.4, inositol-3-phosphate synthase.
CAS REGISTRY NUMBER
COMMENTARY hide
9025-54-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain K84
-
-
Manually annotated by BRENDA team
strain K84
-
-
Manually annotated by BRENDA team
AKU 101; IAM 1061
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
L. ssp. vulgaris
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain YS-314
SwissProt
Manually annotated by BRENDA team
strain YS-314
SwissProt
Manually annotated by BRENDA team
chestnut blight fungus
-
-
Manually annotated by BRENDA team
chestnut blight fungus
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
white leghorn
-
-
Manually annotated by BRENDA team
isolate 2001
UniProt
Manually annotated by BRENDA team
Golden Syrian hamster
-
-
Manually annotated by BRENDA team
Micromonospora faeni
-
-
-
Manually annotated by BRENDA team
green bean
-
-
Manually annotated by BRENDA team
P. aeruginosa; P. putida
-
-
Manually annotated by BRENDA team
Sprague-Dawley
-
-
Manually annotated by BRENDA team
strain W303D
-
-
Manually annotated by BRENDA team
spinach
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
-
treatment with 50 microg/ml N-nitrosomethylbenzylamine results in twenty-eight differentially expressed protein spots in HEEC cells. Two tumor suppressor proteins, prohibitin and c-Myc binding protein, are down-regulated in NMBA-treated HEEC cells. S-adenosylhomocysteine hydrolase, is up-regulated in NMBA-treated HEEC cells
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
(+/-)-aristeromycin + homocysteine
?
show the reaction diagram
1-methyladenosine
?
show the reaction diagram
-
-
-
-
r
2-aminoadenosine + homocysteine
?
show the reaction diagram
-
-
-
-
r
2-aza-3-deazaadenosine + homocysteine
?
show the reaction diagram
2-chloroadenosine + homocysteine
?
show the reaction diagram
2-hydroxyadenosine + homocysteine
?
show the reaction diagram
-
-
-
-
r
3-deaza-(+/-)-aristeromycin + homocysteine
?
show the reaction diagram
3-deazaadenosine + L-homocysteine
3-deazaadenosylhomocysteine
show the reaction diagram
4',5'-dehydroadenosine + H2O
adenosine
show the reaction diagram
-
favors formation of 4',5'-dehydroadenosine, precursor reaction
-
r
7-deaza-8-azaadenosine + homocysteine
?
show the reaction diagram
8-aminoadenosine + homocysteine
?
show the reaction diagram
8-azaadenosine + homocysteine
?
show the reaction diagram
adenosine N1-oxide + homocysteine
?
show the reaction diagram
carboxylic analogue of adenosine
?
show the reaction diagram
-
-
-
-
r
cysteine + adenosine
AdoCys
show the reaction diagram
-
-
-
r
DL-homocysteine + 3-deazaadenosine
?
show the reaction diagram
DL-homocysteine + adenosine
S-adenosyl-DL-homocysteine
show the reaction diagram
DL-homocysteine + adenosine
S-adenosyl-DL-homocysteine + H2O
show the reaction diagram
DL-homocysteine thiolactone
?
show the reaction diagram
-
-
-
-
r
inosine + homocysteine
?
show the reaction diagram
L-homocysteine + adenosine
S-adenosyl-L-homocysteine + H2O
show the reaction diagram
L-homocysteine + adenosine + H2O
S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
r
N6-hydroxyadenosine + homocysteine
?
show the reaction diagram
-
-
-
-
r
N6-methyladenosine + homocysteine
?
show the reaction diagram
nebularine + homocysteine
?
show the reaction diagram
pyrazomycin + homocysteine
?
show the reaction diagram
S-adenosyl-DL-homocysteine + H2O
DL-homocysteine + adenosine
show the reaction diagram
S-adenosyl-L-homocysteine + H2O
adenosine + L-homocysteine
show the reaction diagram
S-adenosyl-L-homocysteine + H2O
L-homocysteine + adenosine
show the reaction diagram
S-adenosyl-L-homocysteine + H2O
S-inosyl-L-homocysteine + NH3
show the reaction diagram
tubercidin + L-homocysteine
?
show the reaction diagram
-
-
-
-
r
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
L-homocysteine + adenosine
S-adenosyl-L-homocysteine + H2O
show the reaction diagram
L-homocysteine + adenosine + H2O
S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
r
S-adenosyl-L-homocysteine + H2O
adenosine + L-homocysteine
show the reaction diagram
S-adenosyl-L-homocysteine + H2O
L-homocysteine + adenosine
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-aristeromycin
(-)-5'-noraristeromycin
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
(1R,2S,3R)-3-(6-amino-4,5-dihydro-9H-purin-9-yl)cyclopentane-1,2-diol
-
-
(1R,2S,3R,5R)-3-(6-amino-4,5-dihydro-9H-purin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
-
-
(1R,2S,3S)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-4-fluorocyclopentane-1,2-diol
-
-
(1R,2S,3S)-3-(8-aminoimidazo[1,2-a]pyrazin-3-yl)cyclopentane-1,2-diol
-
-
(1R,2S,3S,5S)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-5-methylcyclopentane-1,2-diol
-
-
(1R,2S,4r)-4-(4-amino-6,7-difluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol
-
-
(1R,2S,4r)-4-(4-amino-6-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol
-
-
(1R,2S,4r)-4-(4-amino-7-chloro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol
-
-
(1R,2S,4r)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol
-
-
(1R,2S,4r)-4-(4-amino-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol
-
-
(1R,2S,4r)-4-(6-amino-2-fluoro-9H-purin-9-yl)cyclopentane-1,2-diol
-
-
(1S,2R,3S,4S)-4-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2,3-triol
-
-
(1S,2R,5R)-5-(6-amino-4,5-dihydro-9H-purin-9-yl)-3-(chloromethyl)cyclopent-3-ene-1,2-diol
-
-
(1S,2R,5R)-5-(6-amino-4,5-dihydro-9H-purin-9-yl)cyclopent-3-ene-1,2-diol
-
-
(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)-3-(prop-1-yn-1-yl)cyclopent-3-ene-1,2-diol
-
i.e. prop-1-yn-1-yl-substitued neplanocin A, 81% inhibition at 0.01 mM
(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)-3-phenylcyclopent-3-ene-1,2-diol
-
i.e. phenyl-substitutued neplanoocin A, 64% inhibition at 0.1 mM
(1S,2R,5S)-5-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-4-fluorocyclopent-3-ene-1,2-diol
-
-
(1S,2R,5S)-5-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-3-ene-1,2-diol
-
-
(1S,2S,3S,5S)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-5-fluorocyclopentane-1,2-diol
-
-
(2R)-3-(adenin-9-yl)-2-hydroxypropanoic acid
-
-
(2R,3R)-4-(3-deazaadenin-9-yl)-2,3-dihydroxybutanoic acid
-
; in rats fed by the enzyme inhibitor, the total plasma cholesterol and phospholipids decreases
(2R,3R)-4-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-2,3-dihydroxy-N-methylbutanamide
-
-
(2R,3R)-methyl 4-(3-deazaadenin-9-yl)-2,3-dihydroxybutanoic acid
-
-
(2R,3R)-methyl-4-(3-deazaadenin-9-yl)-2,3-dihydroxybutanoic acid
-
in rats fed by the enzyme inhibitor, the total plasma cholesterol and phospholipids decreases
(2R,3R)-N-methyl-4-(3-deazaadenin-9-yl)-2,3-dihydroxybutanamide
-
-
(2S)-3-(adenin-9-yl)-2-hydroxypropanoic acid
-
-
(6'R)-6'-C-methylneplanocin A
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
(E)-4',5'-didehydro-2',5'-dideoxy-5'-fluoroadenosine
-
-
(E)-4',5'-didehydro-5'-deoxy-5'-chloro-5'-fluoroadenosine
-
competitive
(E)-5'-deoxy-5'-(iodomethylene)adenosine
-
similar inhibitory activity against both Trichosoma vaginalis and trypanosomes, inhibits growth of Trichosoma vaginalis strain T1
(E)-6-chloro-6-cyano-5,6-didehydro-6-deoxyhomoadenosine
-
mechanism-based inhibitor, covalent labeling of enzyme. Inactivation results in 28% loss of NAD+
(E)-6-cyano-5,6-didehydro-6-deoxyhomoadenosine
-
mechanism-based inhibitor, type I inhibitor. Inactivation results in 66% loss of NAD+
(E)-9-(5-deoxy-5-fluoro-beta-D-erythro-pent-4-enofuranosyl)adenine
(E)-9-(5-deoxy-5-fluoro-beta-D-threo-pent-4-enofuranosyl)-9H-purin-6-amine
-
competitive
(S)-9-(2,3-Dihydroxypropyl)adenine
100 nM, 7% loss of activity
(Z)-4',5'-didehydro-2',5'-dideoxy-5'-fluoroadenosine
-
competitive
(Z)-4',5'-didehydro-5'-chloro-5'-deoxyadenosine
-
competitive
(Z)-4',5'-didehydro-5'-deoxy-5'-chloro-5'-fluoroadenosine
-
competitive
(Z)-5'-deoxy-5'-(iodomethylene)adenosine
-
similar inhibitory activity against both Trichosoma vaginalis and trypanosomes, inhibits growth of Trichosoma vaginalis strain T1
(Z)-6-cyano-5,6-didehydro-6-deoxyhomoadenosine
-
mechanism-based inhibitor, covalent labeling of enzyme. Inactivation results in 27% loss of NAD+
(Z)-9-(5-deoxy-5-fluoro-beta-D-erythro-pent-4-enofuranosyl)adenine
(Z)-9-(5-deoxy-5-fluoro-beta-D-threo-pent-4-enofuranosyl)-9H-purin-6-amine
-
competitive
1,2,4,triazole-3-carboxamide riboside
-
ribavirin
1-methyladenosine
-
-
1-[(1S,4R,5S)-2-fluoro-4,5-dihydroxycyclopent-2-en-1-yl]pyrimidine-2,4(1H,3H)-dione
-
-
2'-deoxyadenosine
2'3'-dideoxyadenosine
-
-
2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-fluorophenyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
4.56% inhibition at 0.0025 mM; 8.23% inhibition at 0.0025 mM
2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-tolyl)-amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
4.89% inhibition at 0.0025 mM
2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)-(1-methyl-1H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
30.19% inhibition at 0.0025 mM
2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)-(2-methyl-2H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
27.15% inhibition at 0.0025 mM
2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(1-methyl-1H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
85.72% inhibition at 0.0025 mM
2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(2-methyl-2H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
86.56% inhibition at 0.0025 mM
2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(4-tolyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
19.23% inhibition at 0.0025 mM
2-((4-(1H-pyrrol-1-yl)phenyl)(2-((2-(diethylamino)-ethyl)amino)-2-oxoethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
20.16% inhibition at 0.0025 mM
2-((4-(1H-pyrrol-1-yl)phenyl)(2-((2-(ethylamino)-ethyl)amino)-2-oxoethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
79.46% inhibition at 0.0025 mM
2-((4-(1H-pyrrol-1-yl)phenyl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
21.46% inhibition at 0.0025 mM
2-((4-fluorophenyl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)-amino)ethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
-
2.63% inhibition at 0.0025 mM
2-([5-chloro-2-(4-chlorophenoxy)phenyl][2-oxo-2-[(piperidin-2-ylmethyl)amino]ethyl]amino)-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-([5-chloro-2-(4-chlorophenoxy)phenyl]{2-[(2,3-dihydro-1H-inden-2-yl)amino]-2-oxoethyl}amino)-N-[2-(pyrrolidin-1-yl)ethyl]acetamide
-
-
-
2-amino-4'-alpha-fluoro-(9-((1'R,2'S,3'R)-2',3'-dihydroxy-cyclopentan-1'-yl)adenine)
-
slight inhibition
2-Aminoadenosine
-
-
2-aminoaristeromycin
2-aza-3-deazaadenosine
2-chloro-3-deazaadenosine
-
irreversible
2-chloroadenosine
2-Deoxycoformycin
-
-
2-fluoroaristeromycin
2-fluoronoraristeromycin
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[(2R)-pyrrolidin-2-ylmethyl]amino]ethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[(2S)-pyrrolidin-2-ylmethyl]amino]ethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(piperidin-1-yl)ethyl]amino]ethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(propan-2-ylamino)ethyl]amino]ethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-(1,3-dihydro-2H-isoindol-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-(3,4-dihydroisoquinolin-2(1H)-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-cyclohexyl-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-(1,2,3,4-tetrahydronaphthalen-2-yl)acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-(2-phenylethyl)acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-(piperidin-4-yl)acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-(trans-4-phenylcyclohexyl)acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-phenylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-[1-(methylsulfonyl)piperidin-4-yl]acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methyl-N-[4-(methylsulfonyl)piperazin-1-yl]acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[3-(pyrrolidin-1-yl)propyl]amino]ethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-[[2-(dimethylamino)ethyl]amino]-2-oxoethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-[[2-(ethylamino)ethyl]amino]-2-oxoethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-[[2-(methylamino)ethyl]amino]-2-oxoethyl)amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl][2-(1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]amino]-N-[2-(pyrrolidin-1-yl)ethyl]acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl][2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino]-N-[2-(pyrrolidin-1-yl)ethyl]acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl][2-oxo-2-(4-phenylpiperidin-1-yl)ethyl]amino]-N-[2-(pyrrolidin-1-yl)ethyl]acetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl][2-oxo-2-(piperidin-3-ylamino)ethyl]amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-[[5-chloro-2-(4-chlorophenoxy)phenyl][2-oxo-2-(pyrrolidin-3-ylamino)ethyl]amino]-N-(2,3-dihydro-1H-inden-2-yl)-N-methylacetamide
-
-
2-{[5-chloro-2-(4-chlorophenoxy)phenyl](2-{[(2-fluorophenyl)methyl]amino}-2-oxoethyl)amino}-N-[2-(pyrrolidin-1-yl)ethyl]acetamide
-
-
-
2-{[5-chloro-2-(4-chlorophenoxy)phenyl](2-{[2-(methylamino)ethyl]amino}-2-oxoethyl)amino}-N-(1,3-dihydro-2H-isoindol-2-yl)-N-methylacetamide
-
-
-
3'-deoxyadenosine
-
-
3'-keto aristeromycin
-
3-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
3-(6-amino-9H-purin-9-yl)cyclopentane-1,2-diol
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
3-acetylpyridine adenine dinucleotide
-
0.02 mM, 94% residual activity in presence of 0.05 mM NAD, pH 7.4
3-deaza-(+/-)-aristeromycin
3-deaza-adenosine
-
the inhibitor of S-adenosyl homocysteine hydrolase prevents oxidative damage and cognitive impairment following folate and vitamin E deprivation in a murine model of age-related, oxidative stress-induced neurodegeneration. The inhibitor might by useful in therapeutic approach to delay neurodegeneration in Alzheimer's disease
3-Deazaadenine
-
-
3-deazaadenosine
3-deazaadenosylhomocysteine
-
-
3-deazaaristeromycylhomocysteine
-
-
3-deazaneplanocin A
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
3-pyridinaldehyde adenine dinucleotide
-
0.02 mM, 77% residual activity in presence of 0.05 mM NAD, pH 7.4
4',5'-dehydroadenosine
-
-
4'-beta-fluoro-(9-((1'R,2'S,3'R)-2',3'-dihydroxy-cyclopentan-1'-yl)adenine)
-
slight inhibition
5'-deoxy,5'-methylthioadenosine
-
-
5'-deoxy-5',5'-difluoradenosine
5'-deoxyadenosine
-
-
5'-iodo-5'-deoxyadenosine
-
-
5'-S-cyano-5'-thioadenosine
-
-
5'-S-ethynyl-5'-thioadenosine
-
-
5'-S-vinyl-5'-thioadenosine
-
-
5,5'-dithiobis-(2-nitrobenzoate)
-
-
5-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-3-ene-1,2-diol
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
5-(6-amino-9H-purin-9-yl)cyclopent-3-ene-1,2-diol
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
5-(6-aminopurin-9-yl)-3-hydroxymethylcyclopent-3-ene-1,2-diol
-
-
5-(6-aminopurin-9-yl)-4-fluoro-3-hydroxymethylcyclopent-3-ene-1,2-diol
-
i.e. fluoroneplanocin A, mechanism-based inhibitor, crystallization data
5-(6-aminopurin-9-yl)-4-fluorocyclopent-3-ene-1,2-diol
-
-
5-(6-aminopurin-9-yl)-cyclopent-3-ene-1,2-diol
-
-
5-amino-4-imidazole carboxamide riboside
-
-
6'-beta-fluoroaristeromycin
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
7-deaza-8-azaadenosine
8-(3-aminopropylamino)adenosine
-
-
8-Aminoadenosine
8-azaadenosine
9-(2,3-Dihydroxypropyl)adenine
-
-
9-(2-deoxy-beta-D-erythro-pentodialdo-1,4-furanosyl)adenine
-
-
-
9-(2-deoxy-beta-D-erythro-pentodialdo-1,4-furanosyl)adenine oximes
-
(E/Z)
-
9-(3-deoxy-beta-D-erythro-pentodialdo-1,4-furanosyl)adenine
-
-
-
9-(3-deoxy-beta-D-erythro-pentodialdo-1,4-furanosyl)adenine oximes
-
(E/Z)
-
9-(5,6-dideoxy-6-iodo-beta-D-ribo-hex-5-ynofuranosyl)-9H-purin-6-amine
-
i.e. 5',5',6',6'-tetradehydro-6'-deoxy-6'-iodohomoadenosine, strong
9-(6-bromo-5,6-dideoxy-beta-D-ribo-hex-5-ynofuranosyl)-9H-purin-6-amine
-
i.e. 5',5',6',6'-tetradehydro-6'-deoxy-6'-bromohomoadenosine, partial, 2 mol of the inhibitor is covalently bound to Lys318 of the two subunits of the homotetramer
9-(alpha-L-lyxo-pentodialdo-1,4-furanosyl)adenine
-
-
-
9-(alpha-L-lyxo-pentodialdo-1,4-furanosyl)adenine oximes
-
(E/Z)
-
9-(beta-D-arabino-pentodialdo-1,4-furanosyl)adenine
-
-
-
9-(beta-D-arabino-pentodialdo-1,4-furanosyl)adenine oximes
-
(E/Z)
-
9-(beta-D-ribo-pentodialdo-1,4-furanosyl)adenine
-
-
-
9-(beta-D-ribo-pentodialdo-1,4-furanosyl)adenine (adenosine-5'-carboxaldehyde)
-
-
-
9-(beta-D-ribo-pentodialdo-1,4-furanosyl)adenine O-benzyloximes
-
(E/Z)
-
9-(beta-D-ribo-pentodialdo-1,4-furanosyl)adenine O-ethyloximes
-
(E/Z)
-
9-(beta-D-ribo-pentodialdo-1,4-furanosyl)adenine O-methyloximes
-
(E/Z)
-
9-(beta-D-ribo-pentodialdo-1,4-furanosyl)adenine oximes
-
(E/Z)
-
9-(S)-(2,3-dihydroxypropyl)-adenine
-
inhibitor of SAH-hydrolase. Application on tobacco seeds during 6 days during the germination period. The transient drug treatment induces dosage-dependent global DNA hypomethylation mitotically transmitted to adult plants, pleiotropic developmental defects including decreased apical dominance, altered leaf and flower symmetry, flower whorl malformations and reduced fertility, and dramatic upregulation of floral organ identity genes NTDEF, NTGLO and NAG1 in leaves
9-beta-D-arabinofuranosyl-2-chloroadenine
-
irreversible
9-beta-D-arabinofuranosyl-2-fluoroadenine
-
irreversible
9-beta-D-arabinofuranosyl-3-deazaadenine
-
irreversible
9-beta-D-arabinofuranosyladenine
9-[(1'R,2'S,3'R,5'R)-3',4'-epoxy-2'-hydroxy-cyclopentan-1'-yl]-9-H-2-fluoroadenine
9-[(1'R,2'S,3'S,4'R)-3',4'-epoxy-2'-hydroxy-cyclopentan-1'-yl]-9-H-adenine
-
-
9-[5,6,7,8-tetradeoxy-8-iodo-beta-D-ribo-oct-5(E)-en-7-yno-furanosyl]adenine
-
-
9-[5,6,7,8-tetradeoxy-beta-D-ribo-oct-5(E)-en-7-ynofuranosyl]adenine
-
-
9H-purin-6-amine, 9-(6-chloro-5,6-dideoxy-beta-D-ribo-hex-5-ynofuranosyl)-9H-purin-6-amine
-
i.e. 5',5',6',6'-tetradehydro-6'-deoxy-6'-chlorohomoadenosine partial, 2 mol of the inhibitor is covalently bound to Lys318 of the two subunits of the homotetramer
acid ammonium sulfate
-
-
adenine
adenine arabinoside
-
-
adenine-arabinoside
100 nM, 10% loss of activity
adenosine
adenosine 5'-carboxylate
-
competitive
-
Adenosine diphosphate
-
-
adenosine N1-oxide
adenosine-2',3'-dialdehyde
-
; inhibition of the enzyme, mimicks the induction of caspase-like activity and DNA fragmentation induced by adenosine
adenosine-2'-monophosphate
-
-
adenosine-3',5'-cyclic monophosphate
-
-
Adenosine-3'-monophosphate
-
-
adenosine-5'-monophosphate
adenosine-5'-oxime
-
-
adenosylornithine
-
sinefungin
ADP
-
adenosine analogs exhibit the following trend in the half-maximal inhibitory concentrations: adenosine > AMP > ADP = ATP
AMP
-
adenosine analogs exhibit the following trend in the half-maximal inhibitory concentrations: adenosine > AMP > ADP = ATP
arabinosyladenine
arabinosylguanine
-
-
arabinosylhypoxanthine
-
-
-
aristeromycin
ATP-Mg acetate
-
beta-thionicotinamide adenine dinucleotide
beta-thionicotinamide adenine dinucleotide, reduced form
bisulfite
-
reversible
CaCl2
-
reduces adenosine binding
carbocyclic 3-deazaadenosine
-
potent antiviral based on the inhibitory effect on the replication of two reporter viruses, vesicular stomatitis virus and vaccinia virus
cis-diaminedichloride platinum
Cu2+
-
noncompetitive, binding of Cu2+ results in release of NAD+ cofactors. Cu2+ binds at the central channel and interrupts subunit interactions
D-eritadenine
deoxyadenosine
-
-
dithiothreitol
DL-homocysteine
ethyl 3-[(2R,3R,4R,5S)-4-(acetyloxy)-3-[(tert-butoxycarbonyl)(methyl)amino]-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]propanoate
63.62% inhibition at 0.2 mM
ethyl 3-[(2R,3R,4R,5S)-4-(acetyloxy)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-[(tert-butoxycarbonyl)(methyl)amino]tetrahydrofuran-2-yl]propanoate
79.87% inhibition at 0.2 mM
ethyl 3-[(2R,3R,4R,5S)-4-(acetyloxy)-5-(6-amino-9H-purin-9-yl)-3-[(tert-butoxycarbonyl)(methyl)amino]tetrahydrofuran-2-yl]propanoate
57.21% inhibition at 0.2 mM
ethyl 3-[(2R,3R,4R,5S)-5-[2-(acetylamino)-6-[(diphenylcarbamoyl)oxy]-9H-purin-9-yl]-4-(acetyloxy)-3-[(tert-butoxycarbonyl)(methyl)amino]tetrahydrofuran-2-yl]propanoate
87.58% inhibition at 0.2 mM
ethyl 3-[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-[(tert-butoxycarbonyl)amino]-4-hydroxytetrahydrofuran-2-yl]propanoate
81.13% inhibition at 0.2 mM
formycin B
-
-
Inosine
iodoacetamide
-
-
iodoacetate
-
-
Isothiocyanate
-
fluorescent isothiocyanate
L-cysteine
-
-
L-eritadenine
-
-
L-homocysteine
MDL-28842
-
-
methyl 4-(adenin-9-yl)-2-hydroxybutanoate
methyl 4-[([[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]acetyl)(methyl)amino]piperazine-1-carboxylate
-
-
methyl 4-[([[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]acetyl)(methyl)amino]piperidine-1-carboxylate
-
-
metronidazole
-
-
N-(1-acetylpiperidin-4-yl)-2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methylacetamide
-
-
N-(isoindolin-2-yl)-N-methyl-2-((1-methyl-1H-indazol-5-yl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)amino)-acetamide
-
54.24% inhibition at 0.0025 mM
N-(isoindolin-2-yl)-N-methyl-2-((2-methyl-2H-indazol-5-yl)(2-oxo-2-((2-(piperidin-1-yl) ethyl)amino)ethyl)amino)-acetamide
-
38.24% inhibition at 0.0025 mM
N-(isoindolin-2-yl)-N-methyl-2-((2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)(4-tolyl)amino)acetamide
-
6.97% inhibition at 0.0025 mM
N-benzyl-2-[[5-chloro-2-(4-chlorophenoxy)phenyl](2-oxo-2-[[2-(pyrrolidin-1-yl)ethyl]amino]ethyl)amino]-N-methylacetamide
-
-
N-ethylmaleimide
-
-
N6-methyladenosine
Na+
-
reduces adenosine binding
nebularine
neplanocin A
nicotinamide 1,N6-ethenoadenine dinucleotide
-
0.02 mM, 95% residual activity in presence of 0.05 mM NAD, pH 7.4
nicotinamide guanine dinucleotide
-
0.02 mM, 96% residual activity in presence of 0.05 mM NAD, pH 7.4
nicotinamide hypoxanthine dinucleotide
-
0.02 mM, 96% residual activity in presence of 0.05 mM NAD, pH 7.4
nicotinic acid adenine dinucleotide
-
0.02 mM, 96% residual activity in presence of 0.05 mM NAD, pH 7.4
noraristeromycin
Nucleocidin
-
irreversible
p-chloromercuribenzoate
-
-
p-hydroxymercuribenzoate
-
-
Pyrazomycin
reduced 3-acetylpyridine adenine dinucleotide
-
0.02 mM, 52% residual activity in presence of 0.05 mM NAD, pH 7.4
reduced 3-pyridinaldehyde adenine dinucleotide
-
0.02 mM, 9% residual activity in presence of 0.05 mM NAD, pH 7.4
reduced nicotinamide hypoxanthine dinucleotide
-
0.02 mM, 98% residual activity in presence of 0.05 mM NAD, pH 7.4
reduced thionicotinamide adenine dinucleotide
-
0.02 mM, 8% residual activity in presence of 0.05 mM NAD, pH 7.4
ribavirin
S-adenosyl-L-homocysteine
S-adenosyl-L-methionine
tetraethylene pentamine
-
65% inhibition at 0.0001 mM, 80% inhibition at 0.001 mM
Thionicotinamide adenine dinucleotide
-
0.02 mM, 74% residual activity in presence of 0.05 mM NAD, pH 7.4
trans-diaminedichloride platinum
tubercidin
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-deaza-(+/-)-aristeromycin
-
-
3-deazaadenosine
-
-
5alpha-dihydrotestosterone
-
stimulating and stabilizing, promotes formation of ternary complexes, restores specific activity after hypophysectomy
adenosine
adenosine deaminase
-
adenosine nucleosidase
-
-
-
cAMP
-
cAMP at 0.010 mM enhances the hydrolytic activity of native AdoHcy-hydrolase by 35%, whereas the activity of the enzyme in its NAD+ form is not stimulated by cAMP. The cAMP-binding site at the AdoHcy-hydrolase is independent of the NAD+/NADH ratio of the enzyme and is identical with the high affinity-binding site of adenosine. cAMP does not interact with the catalytic site of AdoHcyhydrolase and does not act as an allosteric effector
homocysteine
-
protection against inactivation by arabinosyl adenine
N-nitrosomethylbenzylamine
-
treatment with 50 microg/ml N-nitrosomethylbenzylamine results in twenty-eight differentially expressed protein spots in HEEC cells. Two tumor suppressor proteins, prohibitin and c-Myc binding protein, are down-regulated in NMBA-treated HEEC cells. S-adenosylhomocysteine hydrolase, is up-regulated in NMBA-treated HEEC cells
-
phosphate
-
-
S-adenosyl-L-homocysteine
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.36
3-deazaadenosine
0.11
4',5'-dehydroadenosine
-
-
0.0002 - 1.5
adenosine
35
cysteine
-
-
0.0006 - 4.6
DL-homocysteine
2
Inosine
-
-
0.06 - 150
L-homocysteine
0.00024 - 0.017
S-adenosyl-DL-homocysteine
0.00075 - 15
S-adenosyl-L-homocysteine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE