Information on EC 2.4.2.1 - purine-nucleoside phosphorylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.2.1
-
RECOMMENDED NAME
GeneOntology No.
purine-nucleoside phosphorylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
purine deoxyribonucleoside + phosphate = purine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
(2)
-
-
-
purine ribonucleoside + phosphate = purine + alpha-D-ribose 1-phosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pentosyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
adenine and adenosine salvage I
-
-
adenine and adenosine salvage III
-
-
adenine and adenosine salvage V
-
-
adenosine nucleotides degradation II
-
-
arsenate detoxification I (glutaredoxin)
-
-
Biosynthesis of secondary metabolites
-
-
fluoroacetate and fluorothreonine biosynthesis
-
-
guanine and guanosine salvage
-
-
guanosine nucleotides degradation III
-
-
Metabolic pathways
-
-
Nicotinate and nicotinamide metabolism
-
-
nucleoside and nucleotide degradation (archaea)
-
-
purine deoxyribonucleosides degradation I
-
-
purine deoxyribonucleosides degradation II
-
-
purine metabolism
-
-
Purine metabolism
-
-
purine ribonucleosides degradation
-
-
Pyrimidine metabolism
-
-
salinosporamide A biosynthesis
-
-
urate biosynthesis/inosine 5'-phosphate degradation
-
-
xanthine and xanthosine salvage
-
-
SYSTEMATIC NAME
IUBMB Comments
purine-nucleoside:phosphate ribosyltransferase
Specificity not completely determined. Can also catalyse ribosyltransferase reactions of the type catalysed by EC 2.4.2.5, nucleoside ribosyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
9030-21-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Aeropyrum pernix DSM 11879
-
UniProt
Manually annotated by BRENDA team
KY3106
-
-
Manually annotated by BRENDA team
KY3106
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
Arthrobacter nucleogenes
KY3168
-
-
Manually annotated by BRENDA team
Arthrobacter nucleogenes KY3168
KY3168
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
strain Alk36
UniProt
Manually annotated by BRENDA team
strain Alk36
UniProt
Manually annotated by BRENDA team
Bacterium cadaveris
Bacterium cadaveris KY3402
KY3402
-
-
Manually annotated by BRENDA team
KY3491
-
-
Manually annotated by BRENDA team
KY3491
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
KY3459
-
-
Manually annotated by BRENDA team
KY3074
-
-
Manually annotated by BRENDA team
KY3074
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
ATCC 954
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
JTS 859
-
-
Manually annotated by BRENDA team
TH 6-2
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Leucisus rusticus
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
KY 3760
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
AJ 2992
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
KY4057
-
-
Manually annotated by BRENDA team
KY4057
-
-
Manually annotated by BRENDA team
Bsi590
Uniprot
Manually annotated by BRENDA team
gene salT
UniProt
Manually annotated by BRENDA team
salmon
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
strain ME49
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
KY4208
-
-
Manually annotated by BRENDA team
KY4208
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
the salT-deficient mutant strain shows reduced salinosporamide A and salinosporamide B synthesis
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
1,6-dihydropurine riboside + phosphate
alpha-D-ribose 1-phosphate + 1,6-dihydropurine
show the reaction diagram
-
-
-
-
?
1-methylguanosine + phosphate
alpha-D-ribose 1-phosphate + 1-methylguanine
show the reaction diagram
-
-
-
-
?
1-methylinosine + phosphate
alpha-D-ribose 1-phosphate + 1-methylhypoxanthine
show the reaction diagram
-
-
-
-
?
2',3'-dideoxyinosine + phosphate
alpha-D-2,3-dideoxyribose 1-phosphate + hypoxanthine
show the reaction diagram
2',3'-dideoxyinosine + phosphate
hypoxanthine + 2,3-dideoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2',3'-dideoxyinosine + phosphate
hypoxanthine + alpha-D-2,3-dideoxyribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-amino-2'-deoxyadenosine + phosphate
adenine + 2-deoxy-2-imino-alpha-D-ribose 1-phosphate
show the reaction diagram
2'-amino-2'-deoxyinosine + phosphate
hypoxanthine + 2-deoxy-2-imino-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxy-2'-fluoroadenosine + phosphate
adenine + 2-deoxy-2-fluoro-alpha-D-arabinofuranose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxy-6-methylpurine nucleoside + phosphate
?
show the reaction diagram
13.2% of the activity with inosine
-
-
?
2'-deoxyadenosine + phosphate
2-deoxy-alpha-D-ribose 1-phosphate + adenine
show the reaction diagram
-
10% of the activity with inosine
-
-
?
2'-deoxyadenosine + phosphate
adenine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
2'-deoxyguanosine + phosphate
guanine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
2'-deoxyguanosine + phosphate
guanine + alpha-D-2-deoxyribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxyinosine + phosphate
2-deoxy-alpha-D-ribose 1-phosphate + hypoxanthine
show the reaction diagram
-
-
-
-
?
2'-deoxyinosine + phosphate
alpha-D-2-deoxyribose 1-phosphate + hypoxanthine
show the reaction diagram
2'-deoxyinosine + phosphate
hypoxanthine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
2,6-dihydropurine nucleoside + phosphate
alpha-D-ribose 1-phosphate + 2,6-dihydropurine
show the reaction diagram
-
-
-
-
2-amino-6-mercapto-7-methylpurine ribonucleoside + alpha-D-ribose 1-phosphate
?
show the reaction diagram
2-amino-6-mercapto-7-methylpurine ribonucleoside + phosphate
alpha-D-ribose 1-phosphate + 2-amino-6-mercapto-7-methylpurine
show the reaction diagram
2-amino-6-mercapto-7-methylpurine ribonucleoside + phosphate
alpha-D-ribose 1-phosphate + ?
show the reaction diagram
-
-
-
-
?
2-fluoro-2'-deoxyadenosine + phosphate
2-fluoroadenine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
2-fluoro-2'-deoxyadenosine + phosphate
2-fluoroadenine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
no substrate for wild-type, substrate of double mutant E201Q/N243D
-
-
?
2-fluoro-2'-deoxyadenosine + phosphate
?
show the reaction diagram
-
a toxic prodrug
-
-
?
2-fluoroadenosine + phosphate
2-fluoroadenine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
3-(beta-D-ribofuranosyl)adenine + alpha-D-ribose 1-phosphate
?
show the reaction diagram
3-(beta-D-ribofuranosyl)hyopxanthine + alpha-D-ribose 1-phosphate
?
show the reaction diagram
3-(beta-D-ribofuranosyl)hypoxanthine + alpha-D-ribose 1-phosphate
?
show the reaction diagram
-
-
-
-
?
3-deazainosine + phosphate
alpha-D-ribose 1-phosphate + 3-deazahypoxanthine
show the reaction diagram
5'-chloro-5'-deoxy-adenosine + phosphate
5-chloro-5-deoxy-D-ribose 1-phosphate + adenine
show the reaction diagram
-
-
-
-
5'-deoxy-5'-fluoroadenosine + phosphate
5-deoxy-5-fluoro-D-ribose-1-phosphate + adenine
show the reaction diagram
-
5'-deoxy-5'-fluoroadenosine + phosphate i.e. 5'-FDA
5-deoxy-5-fluoro-D-ribose-1-phosphate i.e. 5-FDRP
-
?
5'-methylthioinosine + phosphate
hypoxanthine + 5-methylthio-alpha-D-ribose 1-phosphate
show the reaction diagram
5'-methylthioinosine + phosphate
hypoxanthine + 5-methylthio-D-ribose 1-phosphate
show the reaction diagram
6-(2-thienyl)-9-(beta-D-ribofuranosyl)purine + phosphate
6-(2-thienyl)purine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
6-cyclopropyl-9-(beta-D-ribofuranosyl)purine + phosphate
6-cyclopropylpurine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
6-ethyl-9-(beta-D-ribofuranosyl)purine + phosphate
6-ethylpurine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
6-mercaptoguanosine + phosphate
alpha-D-ribose 1-phosphate + 6-mercaptoguanine
show the reaction diagram
-
-
-
-
?
6-mercaptopurine riboside + phosphate
alpha-D-ribose 1-phosphate + 6-mercaptopurine
show the reaction diagram
6-phenyl-9-(beta-D-ribofuranosyl)purine + phosphate
6-phenylpurine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
6-thioxanthine + alpha-D-ribose 1-phosphate
6-thioxanthosine + phosphate
show the reaction diagram
7,8-dimethylguanosine + phosphate
7,8-dimethylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-(beta-D-ribofuranosyl)guanine + alpha-D-ribose 1-phosphate
?
show the reaction diagram
7-(beta-D-ribofuranosyl)hypoxanthine + alpha-D-ribose 1-phosphate
?
show the reaction diagram
7-butylguanosine + phosphate
7-butylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-ethylguanosine + phosphate
7-ethylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-isobutylguanosine + phosphate
7-isobutylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-isopropylguanosine + phosphate
7-isopropylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-methyl-6-thio-guanosine + phosphate
7-methyl-6-thioguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-methyl-8-aminoguanosine + phosphate
7-methyl-8-aminoguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
7-methyladenosine + phosphate
7-methyladenine + alpha-D-ribose 1-phosphate
show the reaction diagram
7-methylguanosine + phosphate
7-methylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
7-methylinosine + phosphate
7-methylhypoxanthine + alpha-D-ribose 1-phosphate
show the reaction diagram
7-N-methyl-6-thiopurine riboside + phosphate
?
show the reaction diagram
-
-
-
-
?
7-prolylguanosine + phosphate
7-prolylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
8-aminoguanine + alpha-D-ribose 1-phosphate
8-aminoguanosine + phosphate
show the reaction diagram
8-azaguanine + alpha-D-ribose 1-phosphate
8-azaguanosine + phosphate
show the reaction diagram
8-azahypoxanthine + alpha-D-ribose 1-phosphate
8-azainosine + phosphate
show the reaction diagram
-
-
-
?
8-methylguanosine + phosphate
8-methylguanine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
9-(2-deoxy-2-fluoro-alpha-D-arabinofuranosyl)adenine + phosphate
adenine + 2-deoxy-2-fluoro-alpha-D-arabinofuranose 1-phosphate
show the reaction diagram
-
-
-
-
?
9-beta-D-(2-deoxyribofuranosyl)-6-methylthiopurine + phosphate
6-methylthiopurine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
9-beta-D-ribofuranosyl-6-methylthiopurine + phosphate
6-methylthiopurine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
9-[2-deoxy-beta-D-ribofuranosyl]-6-methylpurine + phosphate
?
show the reaction diagram
-
a toxic prodrug
-
-
?
9-[6-deoxy-alpha-L-talofuranosyl]-2-F-adenine + phosphate
?
show the reaction diagram
-
-
-
-
?
9-[6-deoxy-alpha-L-talofuranosyl]-6-methylpurine + phosphate
?
show the reaction diagram
-
-
-
-
?
9-[6-deoxy-beta-L-talofuranosyl]-2-fluoro-adenine + phosphate
?
show the reaction diagram
9-[6-deoxy-beta-L-talofuranosyl]-6-methylpurine + phosphate
?
show the reaction diagram
9-[alpha-L-lyxofuranosyl]-2-F-adenine + phosphate
?
show the reaction diagram
-
-
-
-
?
9-[beta-D-arabinofuranosyl]-2-fluoro-adenine + phosphate
?
show the reaction diagram
-
a toxic prodrug
-
-
?
9-[beta-L-lyxofuranosyl]-2-fluoro-adenine + phosphate
?
show the reaction diagram
adenine + deoxyribose 1-phosphate
deoxyadenosine + phosphate
show the reaction diagram
adenine arabinoside + phosphate
alpha-D-arabinose 1-phosphate + adenine
show the reaction diagram
-
49% of the activity with adenosine
-
-
-
adenosine + arsenate
adenine + alpha-D-ribose 1-arsenate
show the reaction diagram
adenosine + phosphate
adenine + alpha-D-ribose 1-phosphate
show the reaction diagram
adenosine + phosphate
alpha-D-ribose 1-phosphate + adenine
show the reaction diagram
activity with mutant enzyme N239D, wild-type and mutant enzyme Y191L show no activity
-
-
?
arabinofuranosyladenine + phosphate
?
show the reaction diagram
4.3% of the activity with inosine
-
-
?
deoxyadenosine + phosphate
alpha-D-ribose 1-phosphate + adenine
show the reaction diagram
deoxyguanosine + phosphate
guanine + alpha-D-deoxyribose 1-phosphate
show the reaction diagram
deoxyinosine + phosphate
hypoxanthine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
deoxyinosine + phosphate
hypoxanthine + alpha-D-deoxyribose 1-phosphate
show the reaction diagram
guanine + alpha-D-ribose 1-phosphate
guanosine + phosphate
show the reaction diagram
-
-
-
-
?
guanine + ribose 1-phosphate
guanosine + phosphate
show the reaction diagram
-
-
-
r
guanosine + arsenate
guanine + alpha-D-ribose 1-arsenate
show the reaction diagram
guanosine + phosphate
guanine + alpha-D-ribose 1-phosphate
show the reaction diagram
hypoxanthine + alpha-D-deoxyribose 1-phosphate
deoxyinosine + phosphate
show the reaction diagram
-
-
-
-
r
hypoxanthine + alpha-D-ribose 1-phosphate
inosine + phosphate
show the reaction diagram
-
-
-
-
r
inosine + arsenate
hypoxanthine + ribose 1-arsenate
show the reaction diagram
inosine + phosphate
hypoxanthine + alpha-D-ribose 1-phosphate
show the reaction diagram
methylthioinosine + phosphate
methylthiohypoxanthine + alpha-D-ribose 1-phosphate
show the reaction diagram
more '
?
show the reaction diagram
-
catalysis involves protonation of the purine base at position N7 by residue Asp204, which is triggered by Arg217
-
-
-
nicotinamide riboside + phosphate
nicotinamide + alpha-D-ribose 1-phosphate
show the reaction diagram
p-nitrophenyl beta-D-ribofuranoside + phosphate
?
show the reaction diagram
-
-
-
-
?
purine riboside + phosphate
alpha-D-ribose 1-phosphate + purine
show the reaction diagram
-
-
-
-
?
ribavirin + phosphate
alpha-D-ribose 1-phosphate + 1,2,4-triazole-3-carboxamide
show the reaction diagram
-
22% of the activity with inosine. Phosphorolysis reaches an equilibrium when 15% of ribavirin is phosphorolyzed
-
-
r
uridine + phosphate
?
show the reaction diagram
-
-
-
-
?
uridine + phosphate
uracil + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
?
xanthosine + arsenate
xanthine + alpha-D-ribose 1-arsenate
show the reaction diagram
xanthosine + phosphate
alpha-D-ribose 1-phosphate + xanthine
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'-deoxyguanosine + phosphate
guanine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2-fluoro-2'-deoxyadenosine + phosphate
?
show the reaction diagram
-
a toxic prodrug
-
-
?
9-[2-deoxy-beta-D-ribofuranosyl]-6-methylpurine + phosphate
?
show the reaction diagram
-
a toxic prodrug
-
-
?
9-[6-deoxy-beta-L-talofuranosyl]-2-fluoro-adenine + phosphate
?
show the reaction diagram
-
a toxic prodrug, substrate of enzyme mutant M64V, the drug product has anti-tumor activity
-
-
?
9-[6-deoxy-beta-L-talofuranosyl]-6-methylpurine + phosphate
?
show the reaction diagram
-
a toxic prodrug, substrate of enzyme mutant M64V, the drug product has anti-tumor activity
-
-
?
9-[beta-D-arabinofuranosyl]-2-fluoro-adenine + phosphate
?
show the reaction diagram
-
a toxic prodrug
-
-
?
9-[beta-L-lyxofuranosyl]-2-fluoro-adenine + phosphate
?
show the reaction diagram
-
a toxic prodrug, substrate of enzyme mutant M64V, the drug product has anti-tumor activity
-
-
?
inosine + phosphate
hypoxanthine + alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-cis-1,1-difluoro-2-(tetrahydro-3-piranozyl)ethylphosphonic acid
-
with (hypoxanthine-9-yl)methyl aglycone, i.e. Yokomatsu compound
(+/-)-cis-1,1-difluoro-2-(tetrahydro-3-piranyl)ethylphosphonic acid with (hypoxanthine-9-yl)methyl aglycone
(3R,4R)-1-((9-deazahypoxanthin-9-yl)methyl)-4-fluoro-4-hydroxymethyl pyrrolidin-3-ol
-
-
(3S)-3-(2-amino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-3-(3-chlorophenyl)propanoic acid
-
IC50: 0.000036 mM
(3S,4R)-4-(guanin-9-yl)-3-hydroxypyrrolidin-1-N-ylcarbonylphosphonic acid
-
competitive. For enzyme from cancer cell lines, Ki values are around 10 to 24 nM
(3S,4S)-1-((9-deazahypoxanthin-9-yl)methyl)-4-fluoro-4-hydroxymethyl pyrrolidin-3-ol
-
-
(S)-3-(guanin-9-yl)pyrrolidin-N-ylcarbonylphosphonic acid
-
competitive. For enzyme from cancer cell lines, Ki values widely vary from 16 to 100 nM
1,6-Dihydropurine riboside
-
-
1-((2-pyrrolidine-1-yl)ethyl)uracil
inhibits both enzymic activity and growth of Plasmodium falciparum
1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine
-
-
1-methylguanine
1-[4-(2,4-dimethylphenyl)-1,3-thiazol-2-yl]guanidine
-
0.1 mM , 79.5% inhibition
1-[4-(4-methylphenyl)-1,3-thiazol-2-yl]guanidine
-
0.1 mM , 70.6% inhibition
2'-deoxy-immucillin-G
-
2'-deoxy-immucillin-H
-
2,6-diamino-7-(5-mercapto-3,3-dimethylpentyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00005 mM
2,6-diamino-7-(cyclohexylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.0066 mM
2,8-diamino-1,7-dihydro-6H-purine-6-thione
-
IC50: 0.00849 mM
2,8-diamino-1,9-dihydro-6H-purin-6-one
-
IC50: 0.002299 mM
2,8-diamino-3-(2-thienylmethyl)-3,9-dihydro-6H-purin-6-one
-
IC50: 0.001758 mM
2,8-diamino-9-(1,3-thiazol-4-ylmethyl)-1,9-dihydro-6H-purin-6-one
-
IC50: 0.001043 mM
2,8-diamino-9-(2-furylmethyl)-1,9-dihydro-6H-purin-6-one
-
IC50: 0.000092 mM; IC50: 0.00271 mM
2,8-diamino-9-(2-thienylmethyl)-1,9-dihydro-6H-purin-6-one
-
IC50: 0.000497 mM
2,8-diamino-9-(4-fluorobenzyl)-1,9-dihydro-6H-purin-6-one
-
IC50: 0.00417 mM
2,8-diamino-9-(pyridin-2-ylmethyl)-1,9-dihydro-6H-purin-6-one
-
IC50: 0.001971 mM
2,8-diamino-9-[(4-methyl-2-thienyl)methyl]-1,9-dihydro-6H-purin-6-one
-
IC50: 0.000362 mM
2,8-diamino-9-[4-(1H-imidazol-1-yl)benzyl]-1,9-dihydro-6H-purin-6-one
-
IC50: 0.000852 mM
2,8-diamino-9-[[1-(heptyloxy)-2-hydroxyethoxy]methyl]-1,9-dihydro-6H-purin-6-one
-
IC50: 0.00152 mM
2-(3,4-dichlorophenyl)-5-thioxo-5,6-dihydro-1H-pyrazolo[4,3-d]pyrimidine-3,7(2H,4H)-dione
-
IC50: 0.00703 mM
2-amino-1,5-dihydro-7-[[(2S)-2-(aminomethyl)-1-pyrrolidinyl]-methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 600 nM
2-amino-1,5-dihydro-7-[[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
acetic acid salt, IC50: 4.0 nM
2-amino-1,5-dihydro-7-[[[2-(hydroxy)ethyl]amino]methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 20 nM
2-amino-6-chloro-7-deazapurine 2'-deoxyriboside
-
-
2-amino-6-mercapto-7-methylpurine ribonucleoside
-
in absence of phosphate the enzyme catalyzes a slow hydrolysis, which is accompanied by inactivation of the enzyme
2-Amino-6-methylthiopurine
-
-
2-amino-6-oxo-9-[3-hydroxy-2-(phosphonomethoxy)propyl]-purine
-
2-amino-7-(1,2-dithian-3-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000018 mM
2-amino-7-(2,3,5-trichlorobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00024 mM
2-amino-7-(2-chlorobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00012 mM
2-amino-7-(2-furylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000083 mM
2-amino-7-(2-hydroxybenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00027 mM
2-amino-7-(2-thienylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000021 mM
2-amino-7-(2-thienylmethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
-
IC50: 0.000674 mM
2-amino-7-(3,4-dichlorobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000017 mM
2-amino-7-(3-chlorobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00002 mM
2-amino-7-(3-fluorobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000024 mM
2-amino-7-(3-hydroxybenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00007 mM
2-amino-7-(3-methoxybenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000082 mM
2-amino-7-(3-methylbenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000057mM
2-amino-7-(3-thienylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000025 mM
2-amino-7-(4-chlorobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000025 mM
2-amino-7-(4-iodobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000023 mM
2-amino-7-(biphenyl-4-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000546 mM
2-amino-7-(cycloheptylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00003 mM
2-amino-7-(cyclohexylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000047 mM
2-amino-7-(cyclopentylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000029 mM
2-amino-7-(piperidin-3-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.001 mM
2-amino-7-(pyridin-2-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
2-amino-7-(pyridin-3-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000025 mM
2-amino-7-(pyridin-4-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000064 mM
2-amino-7-(tetrahydro-2-thienylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000011 mM
2-amino-7-(tetrahydrofuran-2-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00007 mM
2-amino-7-([[(2R,3S)-1,3,4-trihydroxybutan-2-yl]amino]methyl)-3,5-dihydro-4Hpyrrolo[3,2-d]pyrimidin-4-one
-
i.e. DATMe-immucillin-G
2-amino-7-benzyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000051 mM
2-amino-7-cyclohex-1-en-1-yl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.0019 mM
2-amino-7-phenoxy-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000042 mM
2-amino-7-[(3-methylcyclohexyl)methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000025 mM
2-amino-7-[(3-tert-butylcyclohexyl)methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000025 mM
2-amino-7-[(4-chloropyridin-3-yl)methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000135 mM
2-amino-7-[3-(benzyloxy)benzyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000124 mM; IC50: 0.000147 mM
2-amino-7-[3-(trifluoromethyl)benzyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000036 mM
2-amino-7-[4-(benzyloxy)benzyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
2-amino-7-[4-(propan-2-yl)benzyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
2-amino-7-[[(1,3-dihydroxypropan-2-yl)amino]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
i.e. SerMe-immucillin-G
2-amino-7-[[(1R,3S,5S,7S)-4-methyl-2-adamantyl]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00009 mM
2-amino-7-[[(2-hydroxyethyl)(methyl)amino]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 60 nM
2-amino-7-[[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 620 nM
2-amino-7-[[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 600 nM
2-amino-7-[[(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 2 nM
2-amino-7-[[3-(hydroxymethyl)piperidin-1-yl]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.004 mM
2-amino-7-[[bis(2-hydroxyethyl)amino]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 5 nM
2-amino-7-[[ethyl(2-hydroxyethyl)amino]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 220 nM
2-amino-9-(2-thienylmethyl)-8-thioxo-1,7,8,9-tetrahydro-6H-purin-6-one
-
IC50: 0.002866 mM
2-amino-9-[2-(phosphonomethoxy)ethyl]-6-sulfanylpurine
2-chloro-6-(3-phenyl-1-propoxy)purine
-
-
2-chloroadenosine
-
inhibits ribosylation of adenine and N6-furfuryladenine
2-fluoro-2'-deoxyadenosine
-
the substrate releases highly cytotoxic 2-fluoroadenine. 2-Fluoro-2'-deoxyadenosine and 2-fluoroadenine exert strong inhibition of Trichomonas vaginalis growth with estimated IC50 values of 106 nM and 84 nM. 2-Fluoro-2'-deoxyadenosine might be useful as a potential chemotherapeutic agent against Trichomonas vaginalis
2-mercaptoethanol
-
-
2-phenyl-5,7-dithioxo-1,2,4,5,6,7-hexahydro-3H-pyrazolo[4,3-d]pyrimidin-3-one
-
IC50: 0.02284 mM
3,5-bis-(4-chlorobenzoyl)-alpha-D-ribose 1-phosphate
3-((2-pyrrolidine-1-yl)ethyl)uracil
inhibits both enzymic activity and growth of Plasmodium falciparum
3-(2-amino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-3-phenylpropanoic acid
-
IC50: 0.000047 mM
3-(3-chlorophenyl)-3-(2,6-diamino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)propanenitrile
-
IC50: 0.000011 mM
3-(3-chlorophenyl)-3-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)propanenitrile
-
IC50: 0.00001 mM
3-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-3-pyridin-3-ylpropanenitrile
-
IC50: 0.000039 mM
3-[(2R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-A
4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-G
4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-H
4-imino-7-methyl-1,2,3,4-tetrahydropyrazolo [1,5-a] [1,3,5] triazin-2-one
-
-
5'-chloro-5'-deoxy-8-aminoguanosine
5'-deoxy-5'-iodo-9-deazainosine
-
-
5'-deoxy-5'-iodoinosine
-
-
5'-deoxy-immucillin-H
-
-
5'-methylthio-immucillin-H
5,5'-dithiobis(2-nitrobenzoic acid)
5-(2,6-diamino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-3,3-dimethylpentane-1-sulfonamide
-
IC50: 0.0001 mM
5-amino-3-(2-thienylmethyl)-3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
-
IC50: 0.001839 mM
6-(2,6-diamino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-4,4-dimethylhexanamide
-
IC50: 0.2 mM
6-(2,6-diamino-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)-4,4-dimethylhexanenitrile
-
IC50: 0.00026 mM
6-amino-2-chloro-7-deazapurine 2'-deoxyriboside
-
-
6-amino-5-bromopyrimidine-2,4(1H,3H)-dione
-
formation of eight hydrogen bonds with key residues in the active site E203, N245 and T244
6-amino-7-(2-thienylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00016 mM
6-amino-7-phenylethinyl-7-deazapurine 2'-deoxyriboside
-
-
6-benzyloxy-2-chloropurine
-
-
6-chloro-7-deazapurine 2'-deoxyriboside
-
-
6-hydroxy-9-p-aminobenzylpurine
-
-
6-Mercaptopurine
-
-
6-methylformycin
-
-
-
6-methylthiopurine
-
-
6-Thioxanthine
-
-
6-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
7-(3-thienylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000028 mM
7-(cyclopentylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000029 mM
7-(pyridin-3-ylmethyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00004 mM
7-benzyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.000035 mM
7-Deazaguanine
-
-
7-Deazainosine
7-deazathioinosine
-
-
7-ketopyrazolo[4,3-d]pyrimidine
-
inhibits phosphorolysis of 7-methylguanosine uncompetitively, inhibits synthesis of 8-azaguanosine competitively
7-methylguanine
-
7-[(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-2-yl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
i.e. forodesine
7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-6-carboxylic acid
-
-
7-[3-(benzyloxy)benzyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
IC50: 0.00019 mM
7-[[(1,3-dihydroxypropan-2-yl)amino]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
7-[[(3R,4R)-4-hydroxy-3-(hydroxymethyl)pyrrolidin-2-yl]methyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
i.e. BCX-4208, mimics the charged ribosyl oxocarbenium ion formed during the transition state
7KPP
-
non-substrate inhibitor of both the phosphorolytic and reverse synthetic pathways, inhibits synthesis of 8-azaguanosine from 8-azaguanine competitively
8-amino-3-(2-thienylmethyl)guanine
-
-
8-amino-5'-deoxy-5'-chloroguanosine
8-amino-5'-deoxy-5'-iodoguanosine
-
-
8-Amino-9-benzylguanine
8-aminoguanine
-
-
8-aminoguanosine
8-aminoquinazolinone
-
-
8-aza-2,6-diamino-(S)-9-[2-(phosphonomethoxy)ethyl]-purine
-
8-aza-2,6-diaminopurine
-
noncompetitive
8-bromo-N(9)-acycloguanosine
-
-
9-(1,3-dihydroxy-2-propoxymethyl)guanine
-
-
9-(2'-benzyl-5',5'-difluoro-5'-phosphonopentyl)guanine
9-(2-fluoro-3,4-dihydroxybutyl)-guanine
9-(2-hydroxyethoxymethyl)guanine
-
-
9-(2-phosphonylmethoxyethyl)-8-azaguanine
9-(3,4-dihydroxybutyl)guanine
-
and analogues
9-(5',5'-difluoro-5'-phosphonobutyl)-9-deazaguanine
9-(5',5'-difluoro-5'-phosphonoheptyl)-9-deazaguanine
9-(5',5'-difluoro-5'-phosphonopentyl)-9-deazaguanine
9-(5,5-difluoro-5-phosphonopentyl)guanine
9-(5,5-difluoro-5-phosphopentyl)guanine
-
-
9-(5,5-difluorophosphonopentyl)guanine
-
-
9-(5-phosphonopentyl)guanine
-
-
9-benzylguanine
9-deazaguanine
acyclovir
adenine
-
-
adenosine
allopurinol
-
-
alpha-D-ribose 1-phosphate
aminopterin
-
noncompetitive
Azaguanine
-
-
cis-1,1-difluoro-2-(tetrahydro-3-piranozyl)ethylphosphonic acid
-
with (hypoxanthine-9-yl)methyl aglycone
cis-1-((9-deazahypoxanthin-9-yl)methyl)-4-fluoro-4-hydroxymethylpyrrolidin-3-ol
-
-
D,L-6-methyl 5,6,7,8-tetrahydropterin
-
competitive
DADMe-immucillin-G
-
-
DADMe-immucillin-H
-
-
DATMe-immucillin-H
-
-
deoxyadenosine
-
-
deoxyimmucillin-H
deoxyinosine
-
-
diphosphate
-
-
EGTA
-
-
erythro-9-(2-hydroxy-3-nonyl)adenine
-
competitive
folate
formycin
-
-
Formycin A
formycin B
forodesine
-
a highly potent, orally active, rationally designed PNP inhibitor, that is active in preclinical studies with malignant cells and clinical utility against T-cell acute lymphoblastic leukemia and cutaneous T-cell lymphoma; a highly potent, orally active, rationally designed PNP inhibitor, use for the management of some B-cell malignancies
ganciclovir
Guanine
guanosine
hypoxanthine
hypoxanthine arabinoside
-
-
immucillin-A
immucillin-G
immucillin-H
Inosine
L-4'-deaza-1'-aza-2'-deoxy-1'-(9-methylene)-immucillin-H
-
-
L-immucillin-H
-
-
N(1)-Methylformycin A
-
-
N(6)-methyl-formycin A
-
-
N(6)-Methylformycin A
N(6)-methylformycin B
-
-
N(7)-acycloguanosine
N(7)-methylformycin A
-
-
N(9)-acycloguanosine
Oxoallopurinol
-
-
oxoformycin A
-
weak
-
oxoformycin B
-
weak
phosphate
purine riboside
-
-
quinazolinone
-
-
SerMe-immucillin-H
-
-
xanthine
Xanthosine
additional information