Information on EC 2.4.2.4 - thymidine phosphorylase

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

EC NUMBER
COMMENTARY hide
2.4.2.4
-
RECOMMENDED NAME
GeneOntology No.
thymidine phosphorylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
thymidine + phosphate = thymine + 2-deoxy-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
Drug metabolism - other enzymes
-
-
Metabolic pathways
-
-
pyrimidine deoxyribonucleosides degradation
-
-
pyrimidine metabolism
-
-
Pyrimidine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
thymidine:phosphate deoxy-alpha-D-ribosyltransferase
The enzyme in some tissues also catalyses deoxyribosyltransferase reactions of the type catalysed by EC 2.4.2.6, nucleoside deoxyribosyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
9030-23-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
K12
-
-
Manually annotated by BRENDA team
Mus musculus C57Bl6/J
C57Bl6/J mice
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-(2',6'-dideoxy-alpha-L-lyxo-hexafuranosyl)thymine + phosphate
?
show the reaction diagram
-
-
-
-
?
1-(2',6'-dideoxy-alpha-L-lyxohexafuranosyl)thymine + phosphate
thymine + 2,6-dideoxy-L-lyxohexafuranose 1-phosphate
show the reaction diagram
-
-
-
-
?
1-(2',6'-dideoxy-beta-D-ribo-hexafuranosyl)thymine + phosphate
?
show the reaction diagram
-
-
-
-
?
1-(2',6'-dideoxy-beta-D-ribohexafuranosyl)thymine + phosphate
?
show the reaction diagram
-
-
-
-
?
1-(2',6'-dideoxy-beta-D-ribohexafuranosyl)thymine + phosphate
thymine + 2,6-dideoxy-D-ribohexafuranose 1-phosphate
show the reaction diagram
-
-
-
-
?
1-(tetrahydro-2-furanyl)-5-fluorouracil + phosphate
?
show the reaction diagram
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione + phosphate
?
show the reaction diagram
-
56% conversion after one h
-
-
?
1-[(2R,4S,5R)-5-(aminomethyl)-4-hydroxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione + phosphate
?
show the reaction diagram
-
11% conversion after one h
-
-
?
1-[(2R,4S,5R)-5-(hydroxymethyl)-4-sulfanyltetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione + phosphate
?
show the reaction diagram
-
0.76% conversion after one h
-
-
?
1-[(2R,4S,5S)-4-hydroxy-5-(sulfanylmethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione + phosphate
?
show the reaction diagram
-
39% conversion after one h
-
-
?
1-[(2R,4S,5S)-5-(chloromethyl)-4-hydroxytetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione + phosphate
?
show the reaction diagram
-
24% conversion after one h
-
-
?
2'-deoxy-5-nitrouridine + phosphate
5-nitrouracil + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxythymidine + phosphate
thymidine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
2'-deoxythymidine + phosphate
thymine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
?
2'-deoxyuridine + phosphate
?
show the reaction diagram
-
-
-
-
?
3'-amino-3'-deoxythymidine + phosphate
?
show the reaction diagram
3'-deoxy-2',3'-didehydrothymidine + phosphate
?
show the reaction diagram
-
-
-
-
?
3'-deoxy-2',3'-didehydrothymidine + phosphate
thymine + 2,3-dideoxy-2,3-didehydro-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
3'-deoxythymidine + phosphate
thymine + 2,3-dideoxy-D-ribose 1-phosphate
show the reaction diagram
-
3.2% conversion after one h
-
-
?
3'-thiothymidine + phosphate
thymine + 3-thio-2,3-dideoxy-D-ribose 1-phosphate
show the reaction diagram
-
0.76% conversion after 1 h
-
-
?
3-fluorothymidine + phosphate
3-fluorothymine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
4'-thiothymidine + phosphate
?
show the reaction diagram
-
3.8% conversion after one h
-
-
?
4-thiothymidine + phosphate
4-thiothymine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
4-thiothymidine + phosphate
?
show the reaction diagram
-
-
-
-
?
5'-amino-5'-deoxythymidine + phosphate
?
show the reaction diagram
-
-
-
-
?
5'-amino-5'-deoxythymidine + phosphate
thymine + 2,5-dideoxy-5-amino-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-amino-5'-deoxythymidine + phosphate
thymine + 5-amino-2,5-dideoxy-D-ribose 1-phosphate
show the reaction diagram
-
11% conversion after 1 h
-
-
?
5'-chloro-5'-deoxythymidine + phosphate
?
show the reaction diagram
-
-
-
-
?
5'-chloro-5'-deoxythymidine + phosphate
thymine + 5-chloro-2,5-dideoxy-D-ribose 1-phosphate
show the reaction diagram
-
24% conversion after 1 h
-
-
?
5'-deoxy-5'-fluorothymidine + phosphate
thymine + 5-fluoro-2,5-dideoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5-fluorouridine + phosphate
5-fluorouracil + 5-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5'-deoxy-5-fluorouridine + phosphate
5-fluorouracil + 5-deoxyribose-1-phosphate
show the reaction diagram
5'-deoxythymidine + phosphate
?
show the reaction diagram
-
-
-
-
?
5'-deoxythymidine + phosphate
thymine + 2,5-dideoxy-D-ribose 1-phosphate
show the reaction diagram
5'-thiothymidine + phosphate
thymine + 5-thio-2,5-dideoxy-D-ribose 1-phosphate
show the reaction diagram
-
39% conversion after 1 h
-
-
?
5-deoxythymidine + phosphate
thymine + 2,5-dideoxyribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5-fluoro-2'-deoxyuridine + phosphate
5-fluorouracil + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5-fluoro-2'-deoxyuridine + phosphate
5-fluorouracil + 2-deoxyribose-1-phosphate
show the reaction diagram
5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate
5-fluoro-2'-deoxyuridine + phosphate
show the reaction diagram
5-fluorouridine + phosphate
5-fluorouracil + D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
5-fluorouridine + phosphate
5-fluorouracil + ribose 1-phosphate
show the reaction diagram
5-nitro-2'-deoxyuridine + phosphate
5-nitrouracil + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
5-nitro-2'-deoxyuridine + phosphate
5-nitrouridine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
6-azathymidine + phosphate
uracil + deoxyribose-1-phosphate
show the reaction diagram
-
5.4% conversion after one h
-
-
?
bromodeoxyuridine + phosphate
bromouracil + 2-deoxy-D-ribose
show the reaction diagram
deoxythymidine + phosphate
thymidine + 2-deoxy-D-ribose
show the reaction diagram
-
-
-
-
?
deoxythymidine + phosphate
thymidine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
deoxyuridine + phosphate
uracil + 2-deoxy-D-ribose
show the reaction diagram
deoxyuridine + phosphate
uracil + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
-
-
-
-
?
fluorodeoxyuridine + phosphate
fluorouracil + 2-deoxy-D-ribose
show the reaction diagram
-
-
-
-
?
iododeoxyuridine + phosphate
iodouracil + 2-deoxy-D-ribose
show the reaction diagram
thymidine + arsenate
?
show the reaction diagram
thymidine + phosphate
thymine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
thymidine + phosphate
thymine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
thymidine + phosphate
thymine + alpha-D-deoxyribose 1-phosphate
show the reaction diagram
-
-
-
-
r
thymine + 2-deoxy-D-ribose 1-phosphate
thymidine + phosphate
show the reaction diagram
thymine arabinoside + phosphate
thymine + arabinose 1-phosphate
show the reaction diagram
-
-
-
-
?
uracil + phosphate
uracil + ribose 1-phosphate
show the reaction diagram
-
88% conversion after one h
-
-
?
uridine + phosphate
uracil + D-ribose 1-phosphate
show the reaction diagram
uridine + phosphate
uracil + ribose 1-phosphate
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
5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate
5-fluoro-2'-deoxyuridine + phosphate
show the reaction diagram
-
the enzyme converts 5-fluorouracil to 5-fluoro-2'-deoxyuridine, activating the prodrug, overview. This action can only take place if there is enough co-substrate. 5-Fluorouracil prodrugs and metabolism, detailed overview
5-fluoro-2'-deoxyuridine is further converted by thymidine kinase to 5-fluoro-2'-deoxyuridine 5'-monophosphate
-
?
thymidine + phosphate
thymine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
thymidine + phosphate
thymine + 2-deoxy-D-ribose 1-phosphate
show the reaction diagram
thymine + 2-deoxy-D-ribose 1-phosphate
thymidine + phosphate
show the reaction diagram
additional information
?
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2,4,5-trioxo-3-phenethyl-imidazolidin-1-yl)ethanoic acid
-
-
(4xi)-2',3'-O-[(1R)-2-carboxyethylidene]-5-methylcytidine
-
-
(4xi)-5-methyl-2',3'-O-[(1R)-2-phosphonoethylidene]cytidine
-
-
(R)-(1-fluoro-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propan-2-yloxy)methylphosphonic phosphoric anhydride
-
strong inhibitory effect
(R)-1-[2-(phosphonomethoxy)propyl]thymine
-
-
(R)-1-[3-fluoro-2-(phosphonomethoxy)-propyl]thymine
(R)-1-[3-fluoro-2-(phosphonomethoxy)propyl]thymine
-
efficient inhibitor
(R)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]thymine
(S)-(1-fluoro-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propan-2-yloxy)methylphosphonic phosphoric anhydride
-
strong inhibitory effect
(S)-1-[2-(phosphonomethoxy)propyl]thymine
-
-
(S)-1-[3-fluoro-2-(phosphonomethoxy)-propyl]thymine
-
-
(S)-1-[3-fluoro-2-(phosphonomethoxy)propyl]thymine
-
efficient inhibitor
(S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]thymine
-
-
([(1R)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1R)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1R)-2-fluoro-1-[(5-methyl-2,6-dioxotetrahydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
low inhibitory effect
([(1R)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1S)-2-fluoro-1-[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1S)-2-fluoro-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([(1S)-2-fluoro-1-[(5-methyl-2,6-dioxotetrahydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
-
low inhibitory effect
([(1S)-2-hydroxy-1-[(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([2,2,2-trifluoro-1-[(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]ethoxy]methyl)phosphonic acid
([[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl]oxy]methyl)phosphonic acid
-
-
1-(2''-deoxy-beta-D-threo-pentafuranosyl)thymine
-
-
1-(2'-deoxy-beta-D-threo-pentafuranosyl)thymine
-
;
1-(2-hydroxyethoxymethyl)thymine
-
-
1-(8-phosphonooctyl)-6-amino-5-bromouracil
-
competitive
1-(8-phosphonooctyl)-7-deazaxanthine
-
competitive
1-benzyl-imidazolidine-2,4,5-trione
-
-
1-[(R)-3-fluoro-2-(phosphonomethoxy)propyl]thymine
-
-
1-[2-(phosphono-methoxy)ethyl]thymine
-
-
1-[2-(phosphonomethoxy)ethyl]thymine
1-[2-deoxy-3,5-O-[phenyl(phosphono)methylidene]-b-L-erythro-pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione
-
53% inhibition at 0.01 mM; 96% inhibition at 0.01 mM
1-[3,5-O-(2-bromo-1-phosphonoethylidene)-2-deoxy-b-L-erythro-pentofuranosyl]-5-methylpyrimidine-2,4(1H,3H)-dione
-
74% inhibition at 0.01 mM; 80% inhibition at 0.01 mM
2',3'-Dideoxy-5-ethyluridine
-
9% inhibition at 10 mM
2,2'-O-anhydrouridine
-
-
2-deoxy-D-ribose
2-deoxy-L-ribose
-
-
2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
3'-amino-3'-deoxythymidine
-
;
3'-Azido-2',3'-dideoxy-5-ethyluridine
-
16% inhibition at 10 mM
3'-Azido-2',3'-dideoxy-5-methyluridine
-
6% inhibition at 10 mM
3'-Bromo-2',3'-dideoxy-5-ethyluridine
-
9% inhibition at 5 mM
3'-Chloro-2',3'-dideoxy-5-ethyluridine
-
26% inhibition at 10 mM
3'-Chloro-2',3'-dideoxy-5-methyluridine
-
18% inhibition at 10 mM
3'-Deoxythymidine
-
;
3-(2,4,5-trioxo-3-phenethyl-imidazolidin-1-yl)-propionamide
-
-
3-([(1-benzyl-2-hydroxyethyl)imino]methyl)-4Hchromen-4-one
-
-
3-([(2, 4-dichlorophenyl)imino]methyl)-4H-chromen-4-one
-
-
3-([(2-([-(4-oxo-4H-chromen-3-yl)methylidene]amino)ethyl)imino] methyl)-4H-chromen-4-one
-
-
3-([(2-benzoyl-4-chlorophenyl)imino]methyl)-4Hchromen-4-one
-
-
3-([(2-methyl-6-nitrophenyl)imino]methyl)-4Hchromen-4-one
-
-
3-([(3-hydroxy-2-pyridinyl)imino]methyl)-4H-chromen-4-one
-
-
3-([(3-methoxy-4-methylphenyl)imino]methyl)-4Hchromen-4-one
-
-
3-([(3-methylphenyl)imino]methyl)-4H-chromen-4-one
-
-
3-benzoyl-5-chloropyrimidine-2,4(1H,3H)-dione
-
-
3-[3-(3-chlorobenzyl)-2,4,5-trioxo-imidazolidin-1-yl]-propionamide
-
-
4,6-dihydroxy-5-nitropyrimidine
-
0.1 mM, competitive
5'-azido-5'-deoxythymidine
-
-
5'-bromo-5'-deoxythymidine
-
;
5'-chloro-5'-deoxythymidine
-
-
5'-iodo-5'-deoxythymidine
-
;
5'-O-trityl-inosine
5'-O-tritylinosine
5-amino-6-chlorouracil
5-benzyl-6-chloropyrimidine-2,4(1H,3H)-dione
-
-
5-benzylacyclouridine
-
-
5-bromo-2-deoxyuridine
-
100% inhibition at 10 mM
5-bromo-6-(2-imino-pyrrolidin-1-yl)methyl-uracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
5-bromo-6-(3'-methylimidazol-1-yl)uracil
-
IC50: 0.038 mM
5-bromo-6-amino-uracil
-
enzyme inhibition results in a significant increase in basal and oxidative stress-induced apoptosis, the effect is abrogated by supplementation with 2-deoxy-D-ribose-1-phosphate
5-bromo-6-aminouracil
-
-
5-bromo-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
5-bromo-6-[(3-methylimidazol-1-yl)methyl]uracil
-
IC50: 0.017 mM
5-bromo-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
5-Bromouracil
-
0.1 mM, competitive
5-butyl-6-chloropyrimidine-2,4(1H,3H)-dione
-
-
5-chloro-6-(2-imino-pyrrolidin-1-yl)methyluracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4(1H,3H)-pyrimidinedione hydrochloride
-
-
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4-(1H,3H)-pyrimidine
-
-
5-chloro-6-(3'-methylimidazol-1-yl)uracil
-
IC50: 0.035 mM
5-chloro-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
5-chloro-6-[(3-methylimidazol-1-yl)methyl]uracil
-
IC50: 0.018 mM
5-chloro-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
5-chloro-6-[1-(2-iminopyrrolidinyl) methyl] uracil hydrochloride
-
-
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl] uracil
-
-
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl] uracil hydrochloride
-
-
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil
-
-
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil hydrochloride
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracilhydrochloride
5-chloro-6-[1-(imminopyrrolidinyl)methyl]uracil hydrochloride
5-ethyl-1-[(R)-3-fluoro-2-(phosphonomethoxy)propyl]uracil
-
-
5-ethyl-1-[(R)-3-hydroxy-2-(phosphonomethoxy)propyl]uracil
-
-
5-ethyl-1-[(S)-3-fluoro-2-(phosphonomethoxy)propyl]uracil
-
-
5-fluoro-1-(tetrahydrofur-2-yl)uracil
-
-
5-fluoro-6-(1H-imidazol-1-ylmethyl)pyrimidine-2,4(1H,3H)-dione
-
-
5-fluoro-6-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]methyl)pyrimidine-2,4(1H,3H)-dione
-
-
5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil
5-fluoro-6-[(4H-1,2,4-triazol-4-ylamino)methyl]pyrimidine-2,4(1H,3H)-dione
-
-
5-fluorodeoxyuridine
-
80% inhibition at 10 mM
5-fluorouracil
-
0.1 mM, competitive
5-Hydroxymethyluracil
-
35% inactivation at 2 mM
5-Iodouracil
-
His116 directly interacts with the inhibitor via its NE2 group, enzyme binding structure, overview
5-methyluridine
-
-
5-Nitrouracil
-
0.1 mM, competitive
5-phenyl-6-pyrrolidin-1-ylpyrimidine-2,4(1H,3H)-dione
-
-
5-[(1E)-but-1-en-1-yl]-6-chloropyrimidine-2,4(1H,3H)-dione
-
-
6-(1H-imidazol-1-ylmethyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-(2-amino-imidazol-1-yl)methyl-5-bromouracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
6-(2-amino-imidazol-1-yl)methyl-5-chlorouracil
-
tightbinding stoichiometric inhibitor of recombinant Escherichia coli thymidine phosphorylase, can be used as active-site titrants for it using either thymidine or 5-nitro-2'-deoxyuridine as substrate
6-(2-aminoethyl)amine-5-chlorouracil
-
AEAC
6-(3-methylimidazol-1-yl)uracil
-
IC50: 0.110 mM
6-(4-phenlybutylamino)uracil
-
PBAU, 50% inhibition at 0.03 mM
6-(4H-1,2,4-triazol-4-ylmethyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]methyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-amino-5-bromouracil
6-amino-5-chlorouracil
6-aminothymine
6-aminouracil
-
0.1 mM, competitive
6-benzyl-2-thiouracil
-
0.1 mM, mixed inhibition
6-bromo-5-phenylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-(1-methylethenyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-(2-naphthyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-(2-thienyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-(3,5-dimethylphenyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-(4-fluorophenyl)pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-cyclohex-1-en-1-ylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-cyclopent-1-en-1-yluracil
-
-
6-chloro-5-ethylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-heptylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-hexylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-pentylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-phenylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-propylpyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-pyridin-3-ylpyrimidine-2,4(1H,3H)-dione hydrochloride
-
-
6-chloro-5-[(1E)-1-ethylprop-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-[(1E)-pent-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione
-
-
6-chloro-5-[(1E)-prop-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione
-
-
6-fluoro-5-phenylpyrimidine-2,4(1H,3H)-dione
-
-
6-methyl-5-phenylpyrimidine-2,4(1H,3H)-dione
-
-
6-Methyluracil
-
competitive, 86% inhibition at 10 mM and 36% inhibition at 1 mM
6-[(2'-aminoimidazol-1'-yl)methyl]-5-bromouracil
6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
6-[(2'-aminoimidazol-1'-yl)methyl]uracil
6-[(2'-nitroimidazol-1'-yl)methyl]uracil
6-[(2-aminoethyl)amino]-5-phenylpyrimidine-2,4(1H,3H)-dione
-
-
6-[(3-methylimidazol-1-yl)methyl]thymine
-
IC50: 0.06 mM
6-[(3-methylimidazol-1-yl)methyl]uracil
-
IC50: 0.042 mM
6-[(4'-aminoimidazol-1'-yl)methyl]-5-bromouracil
6-[(4'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
6-[(4'-aminoimidazol-1'-yl)methyl]uracil
6-[(4'-nitroimidazol-1'-yl)methyl]uracil
7-deazaxanthine
9-[8-phosphonooctyl]-7-deazaxanthine
-
-
allyloxymethylthymine
-
0.1 mM, uncompetitive
Arabinofuranosyl-5-ethyluracil
-
10% inhibition at 10 mM
aurothioglucose
-
the expression of tyhmidine phosphorylase mRNA is significantly decreased by stimulation with aurothioglucose
Bromouracil
-
100% inactivation at 1 mM
deoxyadenosine
-
20% inactivation at 1 mM
deoxyribose-1-phosphate
-
-
dexamethasone
-
the expression of tyhmidine phosphorylase mRNA is significantly decreased by stimulation with dexamethasone
diethyl ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)(difluoro)methyl)phosphonate
-
-
diethyl ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
diethyl ((2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
diethyl (2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]benzyl)phosphonate
-
-
diethyl ([2-(hydroxymethyl)cyclopent-1-en-1-yl]methyl)phosphonate
-
-
diethyl [(Z)-4-(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)but-2-en-1-yl]phosphonate
-
-
diethyl [(Z)-4-hydroxybut-2-en-1-yl]phosphonate
-
-
diethyl [2-(hydroxymethyl)benzyl]phosphonate
-
-
disodium ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)(difluoro)methyl)phosphonate
-
-
disodium ((2-[(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
disodium ((2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]cyclopent-1-en-1-yl)methyl)phosphonate
-
-
disodium (2-[(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)methyl]benzyl)phosphonate
-
-
disodium [(Z)-4-(5-chloro-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)but-2-en-1-yl]phosphonate
-
-
ftorafur
-
; ftorafur is also called tegafur
hydrogen [[(1R,2S,4S)-2-(hydroxymethyl)-4-(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)pyrrolidinium-1-yl]methyl]phosphonate
-
-
methyluridine
-
-
N'-[-(4-oxo-4H-chromen-3-yl)methylidene]propanohydrazide
-
-
NSC 122612
-
0.12 mM, 27% inhibition
NSC 19791
-
0.89 mM, 14% inhibition
-
NSC 23145
-
0.105 mM, 23% inhibition
NSC 298251
-
0.1 mM, 30% inhibition
NSC 3056
-
0.089 mM, 24% inhibition
NSC 309091
-
0.13 mM, 21% inhibition
NSC 357688
-
0.09 mM, 28% inhibition
NSC 43275
-
0.106 mM, 16% inhibition
NSC 6487
-
0.089 mM, 6% inhibition
NSC 65043
NSC 659977
-
0.134 mM, 60% inhibition
NSC 81031
-
0.93 mM, 15% inhibition
p-chloromercuribenzoate
-
above 0.01 mM
prostaglandin E2
-
-
ribose 1-phosphate
SO42-
-
inhibition reversed by phosphate
thymidine phosphorylase inhibitor
-
-
-
thymine
Uracil
Urea
-
inhibition at high concentration, 4 M, stimulation at low concentration
uridine
xanthine
[(2S,3aR,4R,6R,6aR)-4-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
[(2S,4R,5S)-5-(2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-1,3-oxazolidin-2-yl]phosphonic acid
-
-
[(3aR,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
[(3aR,4R,6R,6aR)-4-(hydroxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
[2-[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]-2-oxoethyl]phosphonic acid
-
41% inhibition at 0.01 mM
[5-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]pentyl]phosphonic acid
-
86% inhibition at 0.01 mM
[6-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]hexyl]phosphonic acid
-
79% inhibition at 0.01 mM
[8-(2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-1-yl)octyl]phosphonic acid
[8-(2,4-dioxo-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-d]pyrimidin-1-yl)octyl]phosphonic acid
[[(1R)-2-(5-ethyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(fluoromethyl)ethoxy]methyl]phosphonic acid
[[(2R,3aR,6aR)-6-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-4-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
-
[[(2R,4R)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
-
83% inhibition at 0.01 mM
[[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
98% inhibition at 0.01 mM
[[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
-
complete inhibition at 0.01 mM
[[(2S,3aR,6aR)-6-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-4-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
-
[[(2S,3aR,6aS)-4-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-6-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
-
[[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid
-
complete inhibition at 0.01 mM
[[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
complete inhibition at 0.01 mM
[[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
96% inhibition at 0.01 mM
[[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
-
99% inhibition at 0.01 mM
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid
-
91% inhibition at 0.01 mM
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
97% inhibition at 0.01 mM
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
-
71% inhibition at 0.01 mM
[[(3S,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
-
[[2-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy]methyl]phosphonic acid
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(prop-2-en-1-yloxy)ethoxy]methyl]phosphonic acid
-
90% inhibition at 0.01 mM
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-phenoxyethoxy]methyl]phosphonic acid
-
99% inhibition at 0.01 mM
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethoxy](phenyl)methyl]phosphonic acid
-
91% inhibition at 0.01 mM
[[2-(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethoxy]methyl]phosphonic acid
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cyclophosphamide
docetaxel
-
induces thymidine phosphorylase expression
doxorubicin
-
thymidine phosphorylase expression is upregulated after treatment with 60 mg/m2 doxorubicin
epirubicin
-
thymidine phosphorylase expression is upregulated after treatment with 75 mg/m2 epirubicin
interferon alpha
interferon alpha2b
-
induces thymidine phosphorylase mRNA and protein expression in a dose-dependent manner
-
interferon beta
-
causes a rapid and transient increase of thymidine phosphorylase expression
-
interferon gamma
-
causes a rapid and transient increase of thymidine phosphorylase expression
-
Interleukin-1beta
-
the expression of tyhmidine phosphorylase mRNA is significantly increased by stimulation with interleukin-1beta
-
mitomycin C
-
induces thymidine phosphorylase expression
paclitaxel
Tumor necrosis factor alpha
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.35
1-(2',6'-dideoxy-alpha-L-lyxo-hexafuranosyl)thymine
0.33
1-(2',6'-dideoxy-beta-D-ribo-hexafuranosyl)thymine
-
25C, pH 6.5
0.3 - 0.33
1-(2',6'-dideoxy-beta-D-ribohexafuranosyl)thymine
13.3
1-(Tetrahydro-2-furanyl)-5-fluorouracil
-
-
0.32
2'-deoxyuridine
-
-
0.4
3'-amino-3'-deoxythymidine
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
0.35
3'-deoxy-2',3'-didehydrothymidine
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
10
3'-Deoxythymidine
-
in 50 mM phosphate buffer, pH 6.8
0.25 - 0.28
4-thiothymidine
0.4
5'-amino-5'-deoxythymidine
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
0.3
5'-chloro-5'-deoxythymidine
-
25C, pH 6.5
1.72
5'-deoxy-5-fluorouridine
-
-
0.4 - 32
5'-Deoxythymidine
0.16 - 0.23
5-nitro-2'-deoxyuridine
0.00064 - 2.3
phosphate
0.00166 - 9.3
thymidine
0.0832 - 9.828
thymine
47.6
uridine
-
-
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.45
1-(2',6'-dideoxy-alpha-L-lyxo-hexafuranosyl)thymine
0.1
1-(2',6'-dideoxy-beta-D-ribo-hexafuranosyl)thymine
0.6
1-(2',6'-dideoxy-beta-D-ribohexafuranosyl)thymine
Escherichia coli
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
35
2'-deoxyuridine
Escherichia coli
-
-
1.1
3'-amino-3'-deoxythymidine
Escherichia coli
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
0.4
3'-deoxy-2',3'-didehydrothymidine
Escherichia coli
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
63
4-thiothymidine
0.58
5'-amino-5'-deoxythymidine
Escherichia coli
-
25C, pH 6.5; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
1.7
5'-chloro-5'-deoxythymidine
Escherichia coli
-
-
260
5'-Deoxythymidine
Escherichia coli
-
; in 50 mM potassium phosphate buffer (pH 6.5), at 25C
2.88 - 20
5-nitro-2'-deoxyuridine
0.157 - 1770
thymidine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0435
(4xi)-2',3'-O-[(1R)-2-carboxyethylidene]-5-methylcytidine
-
-
0.000236
(4xi)-5-methyl-2',3'-O-[(1R)-2-phosphonoethylidene]cytidine
-
-
0.0019 - 0.00396
(R)-1-[2-(phosphonomethoxy)propyl]thymine
0.00022 - 0.00344
(R)-1-[3-fluoro-2-(phosphonomethoxy)-propyl]thymine
0.00037 - 0.0027
(R)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]thymine
0.00068 - 0.001
(S)-1-[2-(phosphonomethoxy)propyl]thymine
0.0004 - 0.00064
(S)-1-[3-fluoro-2-(phosphonomethoxy)-propyl]thymine
0.00093 - 0.0013
(S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]thymine
0.45
1-(2''-deoxy-beta-D-threo-pentafuranosyl)thymine
1.5
1-(2-hydroxyethoxymethyl)thymine
-
pH 7.5, 25C, activity with 4-thiothymidine
0.00146 - 0.00173
1-[2-(phosphono-methoxy)ethyl]thymine
0.4 - 0.5
2,2'-O-anhydrouridine
0.6
3'-amino-3'-deoxythymidine
-
25C, pH 6.5; in 50 mM potassium phosphate buffer, pH 6.5, 25C
0.85
3'-Deoxythymidine
-
25C, pH 6.5; in 50 mM potassium phosphate buffer, pH 6.5, 25C
0.021 - 0.211
4,6-dihydroxy-5-nitropyrimidine
0.4
5'-bromo-5'-deoxythymidine
0.039 - 0.146
5'-O-trityl-inosine
0.0002 - 0.00455
5-benzyl-6-chloropyrimidine-2,4(1H,3H)-dione
0.0011 - 0.006
5-Bromouracil
0.00103 - 0.00165
5-butyl-6-chloropyrimidine-2,4(1H,3H)-dione
0.017
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4(1H,3H)-pyrimidinedione hydrochloride
-
in 50 mM Tris, 1 mM EDTA, pH 7.4, at 37C
0.0000013 - 0.0000021
5-chloro-6-(2-iminopyrrolidin-1-yl)methyl-2,4-(1H,3H)-pyrimidine
0.000002
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl] uracil hydrochloride
-
-
0.00002
5-chloro-6-[1-(imminopyrrolidinyl)methyl]uracil hydrochloride
-
-
0.4 - 0.45
5-fluoro-1-(tetrahydrofur-2-yl)uracil
0.000051
5-fluoro-6-(1H-imidazol-1-ylmethyl)pyrimidine-2,4(1H,3H)-dione
-
-
0.001
5-fluoro-6-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]methyl)pyrimidine-2,4(1H,3H)-dione
-
-
0.000011 - 0.000017
5-fluoro-6-[(2-aminoimidazol-1-yl)methyl]uracil
0.00037
5-fluoro-6-[(4H-1,2,4-triazol-4-ylamino)methyl]pyrimidine-2,4(1H,3H)-dione
-
-
0.043 - 0.0728
5-fluorouracil
0.48
5-Iodouracil
-
-
0.017
5-methyluridine
-
pH 6.0, recombinant enzyme
0.0051 - 0.0253
5-Nitrouracil
0.02
5-phenyl-6-pyrrolidin-1-ylpyrimidine-2,4(1H,3H)-dione
-
Km above 0.02 mM, enzyme purified from placenta, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C; Km above 0.02 mM, enzyme purified from V79 cells, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C
0.00063 - 0.00092
5-[(1E)-but-1-en-1-yl]-6-chloropyrimidine-2,4(1H,3H)-dione
0.0047
6-(1H-imidazol-1-ylmethyl)pyrimidine-2,4(1H,3H)-dione
-
-
0.000165
6-(2-aminoethyl)amine-5-chlorouracil
-
-
0.054
6-(4H-1,2,4-triazol-4-ylmethyl)pyrimidine-2,4(1H,3H)-dione
-
-
0.0088
6-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]methyl)pyrimidine-2,4(1H,3H)-dione
-
-
0.0034
6-amino-5-chlorouracil
-
-
0.088 - 0.13
6-aminouracil
0.075 - 0.137
6-benzyl-2-thiouracil
0.00121
6-bromo-5-phenylpyrimidine-2,4(1H,3H)-dione
-
enzyme purified from placenta, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C; enzyme purified from V79 cells, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C
0.00334 - 0.0051
6-chloro-5-(1-methylethenyl)pyrimidine-2,4(1H,3H)-dione
0.00394 - 0.00459
6-chloro-5-(2-naphthyl)pyrimidine-2,4(1H,3H)-dione
0.00028 - 0.00054
6-chloro-5-(2-thienyl)pyrimidine-2,4(1H,3H)-dione
0.00127 - 0.00174
6-chloro-5-(3,5-dimethylphenyl)pyrimidine-2,4(1H,3H)-dione
0.00071 - 0.00097
6-chloro-5-(4-fluorophenyl)pyrimidine-2,4(1H,3H)-dione
0.00042 - 0.00075
6-chloro-5-cyclohex-1-en-1-ylpyrimidine-2,4(1H,3H)-dione
0.0002 - 0.00029
6-chloro-5-cyclopent-1-en-1-yluracil
0.02
6-chloro-5-ethylpyrimidine-2,4(1H,3H)-dione
-
Km above 0.02 mM, enzyme purified from placenta, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C; Km above 0.02 mM, enzyme purified from V79 cells, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C
0.0016 - 0.00465
6-chloro-5-heptylpyrimidine-2,4(1H,3H)-dione
0.00106 - 0.00179
6-chloro-5-hexylpyrimidine-2,4(1H,3H)-dione
0.00309 - 0.00367
6-chloro-5-pentylpyrimidine-2,4(1H,3H)-dione
0.0004 - 0.00043
6-chloro-5-phenylpyrimidine-2,4(1H,3H)-dione
0.00402 - 0.00581
6-chloro-5-propylpyrimidine-2,4(1H,3H)-dione
0.00301 - 0.00399
6-chloro-5-pyridin-3-ylpyrimidine-2,4(1H,3H)-dione hydrochloride
0.00049 - 0.00091
6-chloro-5-[(1E)-1-ethylprop-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione
0.00041 - 0.00091
6-chloro-5-[(1E)-pent-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione
0.00117 - 0.00121
6-chloro-5-[(1E)-prop-1-en-1-yl]pyrimidine-2,4(1H,3H)-dione
0.00047 - 0.0005
6-fluoro-5-phenylpyrimidine-2,4(1H,3H)-dione
0.02
6-methyl-5-phenylpyrimidine-2,4(1H,3H)-dione
-
Km above 0.02 mM, enzyme purified from placenta, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C; Km above 0.02 mM, enzyme purified from V79 cells, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C
1.6
6-Methyluracil
-
-
0.02
6-[(2-aminoethyl)amino]-5-phenylpyrimidine-2,4(1H,3H)-dione
-
Km above 0.02 mM, enzyme purified from placenta, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C; Km above 0.02 mM, enzyme purified from V79 cells, in 20 mM Bis-Tris-HCl (pH 6.4), at 37C
0.127 - 0.1286
allyloxymethylthymine
0.67
deoxyribose-1-phosphate
-
-
0.45
ftorafur
-
25C, pH 6.5; in 50 mM potassium phosphate buffer, pH 6.5, 25C
0.005
hydrogen [[(1R,2S,4S)-2-(hydroxymethyl)-4-(5-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)pyrrolidinium-1-yl]methyl]phosphonate
-
-
0.12
methyluridine
-
in 50 mM potassium phosphate buffer, pH 6.5, 25C
2 - 12.5
NSC 65043
0.00002
thymidine phosphorylase inhibitor
-
-
-
0.158
Uracil
-
tumor tissue
0.013 - 0.06
uridine
0.00077
[(2S,3aR,4R,6R,6aR)-4-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
0.004
[(2S,4R,5S)-5-(2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-1,3-oxazolidin-2-yl]phosphonic acid
-
-
0.005
[(3aR,4R,6R,6aR)-4-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-6-(hydroxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
0.01
[(3aR,4R,6R,6aR)-4-(hydroxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuro[3,4-d][1,3]dioxol-2-yl]phosphonic acid
-
-
0.0334
[[(2R,3aR,6aR)-6-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-4-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
-
0.00105
[[(2S,3aR,6aR)-6-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-4-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
-
0.00803
[[(2S,3aR,6aS)-4-(4-amino-5-methyl-2-oxopyrimidin-1(2H)-yl)-6-(hydroxymethyl)hexahydrofuro[3,4-b]furan-2-yl]methyl]phosphonic acid
-
-
0.01
[[(3S,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
-
-
additional information
additional information
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.085
(2,4,5-trioxo-3-phenethyl-imidazolidin-1-yl)ethanoic acid
Escherichia coli
-
pH 7.4, 25C
0.115
1-benzyl-imidazolidine-2,4,5-trione
Escherichia coli
-
pH 7.4, 25C
0.04
3-(2,4,5-trioxo-3-phenethyl-imidazolidin-1-yl)-propionamide
Escherichia coli
-
pH 7.4, 25C
0.473
3-([(1-benzyl-2-hydroxyethyl)imino]methyl)-4Hchromen-4-one
Escherichia coli
-
pH 7.6
0.04
3-([(2, 4-dichlorophenyl)imino]methyl)-4H-chromen-4-one
Escherichia coli
-
pH 7.6
0.15
3-([(2-([-(4-oxo-4H-chromen-3-yl)methylidene]amino)ethyl)imino] methyl)-4H-chromen-4-one
Escherichia coli
-
pH 7.6
0.076
3-([(2-benzoyl-4-chlorophenyl)imino]methyl)-4Hchromen-4-one
Escherichia coli
-
pH 7.6
0.48
3-([(2-methyl-6-nitrophenyl)imino]methyl)-4Hchromen-4-one
Escherichia coli
-
pH 7.6
0.34
3-([(3-hydroxy-2-pyridinyl)imino]methyl)-4H-chromen-4-one
Escherichia coli
-
pH 7.6
0.02
3-([(3-methoxy-4-methylphenyl)imino]methyl)-4Hchromen-4-one
Escherichia coli
-
pH 7.6
0.067
3-([(3-methylphenyl)imino]methyl)-4H-chromen-4-one
Escherichia coli
-
pH 7.6
0.066
3-[3-(3-chlorobenzyl)-2,4,5-trioxo-imidazolidin-1-yl]-propionamide
Escherichia coli
-
pH 7.4, 25C
0.044 - 0.067
5'-O-trityl-inosine
0.038
5-bromo-6-(3'-methylimidazol-1-yl)uracil
Homo sapiens
-
IC50: 0.038 mM
0.0244 - 0.16
5-bromo-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
0.017
5-bromo-6-[(3-methylimidazol-1-yl)methyl]uracil
Homo sapiens
-
IC50: 0.017 mM
0.0066 - 0.181
5-bromo-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
0.035
5-chloro-6-(3'-methylimidazol-1-yl)uracil
Homo sapiens
-
IC50: 0.035 mM
0.0217 - 0.115
5-chloro-6-[(2'-nitroimidazol-1'-yl)methyl]uracil
0.018
5-chloro-6-[(3-methylimidazol-1-yl)methyl]uracil
Homo sapiens
-
IC50: 0.018 mM
0.007 - 0.2
5-chloro-6-[(4'-nitroimidazol-1'-yl)methyl]uracil
0.000035
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracil
Homo sapiens
-
-
0.00002 - 0.000023
5-chloro-6-[1-(2-iminopyrrolidinyl)methyl]uracilhydrochloride
0.11
6-(3-methylimidazol-1-yl)uracil
Homo sapiens
-
IC50: 0.110 mM
0.0016 - 0.0068
6-amino-5-bromouracil
0.0000187 - 0.000019
6-[(2'-aminoimidazol-1'-yl)methyl]-5-bromouracil
0.0000206 - 0.000049
6-[(2'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
0.0001 - 0.00056
6-[(2'-aminoimidazol-1'-yl)methyl]uracil
0.0024 - 0.2577
6-[(2'-nitroimidazol-1'-yl)methyl]uracil
0.06
6-[(3-methylimidazol-1-yl)methyl]thymine
Homo sapiens
-
IC50: 0.06 mM
0.042
6-[(3-methylimidazol-1-yl)methyl]uracil
Homo sapiens
-
IC50: 0.042 mM
0.00065 - 0.041
6-[(4'-aminoimidazol-1'-yl)methyl]-5-bromouracil
0.00073 - 0.026
6-[(4'-aminoimidazol-1'-yl)methyl]-5-chlorouracil
0.1014 - 0.143
6-[(4'-aminoimidazol-1'-yl)methyl]uracil
0.0138 - 0.5
6-[(4'-nitroimidazol-1'-yl)methyl]uracil
0.0065 - 0.045
7-deazaxanthine
0.232 - 0.351
KIN56
0.146
N'-[-(4-oxo-4H-chromen-3-yl)methylidene]propanohydrazide
Escherichia coli
-
pH 7.6
0.077
NSC 65043
Homo sapiens
-
IC50: 0.077 mM
0.0017 - 0.027
[8-(2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-1-yl)octyl]phosphonic acid
0.0073 - 0.0151
[8-(2,4-dioxo-2,3,4,7-tetrahydro-1H-pyrrolo[2,3-d]pyrimidin-1-yl)octyl]phosphonic acid
0.000045
[[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.00025
[[(2R,4S)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.000015
[[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.000011
[[(2S,4S)-2-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.00022
[[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.000045
[[(3R,4R)-3-hydroxy-4-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]methyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.00019
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonothioyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.00035
[[(3S)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl]carbonyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
0.0003
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-(prop-2-en-1-yloxy)ethoxy]methyl]phosphonic acid
Rattus norvegicus
-
about, pH 6.7
0.00075
[[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-1-phenoxyethoxy]methyl]phosphonic acid
Rattus norvegicus
-
pH 6.7
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00002
-
wild-type mouse muscle
0.000205
-
wild-type mouse heart
0.000243
-
TP-/-UP-/- mouse liver
0.000285
-
wild-type mouse spleen
0.00067
-
wild-type mouse kidney
0.000862
-
wild-type mouse lung
0.00136
-
wild-type mouse brain
0.0014
-
wild-type mouse liver
0.00386
-
in normal uterine cervix tissue
0.00527
-
mean thymidine phosphorylase activity in population
0.00946
-
wild-type mouse small intestine
0.01
-
mitochondrial neurogastrointestinal encephalomyopathy syndrome patient, leukocytes
0.04176
-
in cancerous uterine cervix tissue
0.2 - 0.32
-
leukocytes of heterozygous individuals in enzyme mutation and mitochondrial neurogastrointestinal encephalomyopathy syndrome
0.36 - 0.8
-
wild-type activity in leukocytes
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5
-
thymine production, assay at
6.7
-
assay at
7.1
-
assay at
7.5 - 8
-
rapid decrease of activity above and below this range
7.6
-
assay at
7.8
-
assay at
10
-
assay at, pH 10 is used because 2-deoxy-D-ribose 1-phosphate is heat labile at pH 7.4