2.4.2.3: uridine phosphorylase
This is an abbreviated version!
For detailed information about uridine phosphorylase, go to the full flat file.
Word Map on EC 2.4.2.3
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2.4.2.3
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pyrimidine
-
nucleoside
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thymidine
-
uracil
-
5-fluorouracil
-
phosphorolysis
-
salvage
-
orotate
-
phosphoribosyltransferase
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phosphorylases
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thymidylate
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fluoropyrimidine
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udp
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5'-deoxy-5-fluorouridine
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5-fluoro-2'-deoxyuridine
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dihydropyrimidine
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acyclonucleoside
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5-fluorouridine
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ribose-1-phosphate
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capecitabine
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5-methyluridine
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dthdpase
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fdurd
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orotidine
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dihydrouracil
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uridine-cytidine
-
mete
-
diagnostics
-
medicine
-
synthesis
-
drug development
- 2.4.2.3
- pyrimidine
- nucleoside
- thymidine
- uracil
- 5-fluorouracil
-
phosphorolysis
-
salvage
- orotate
-
phosphoribosyltransferase
- phosphorylases
- thymidylate
-
fluoropyrimidine
- udp
- 5'-deoxy-5-fluorouridine
- 5-fluoro-2'-deoxyuridine
- dihydropyrimidine
- acyclonucleoside
- 5-fluorouridine
- ribose-1-phosphate
- capecitabine
- 5-methyluridine
- dthdpase
-
fdurd
- orotidine
- dihydrouracil
-
uridine-cytidine
-
mete
- diagnostics
- medicine
- synthesis
- drug development
Reaction
Synonyms
apUP, EC 2.4.2.23, L-UrdPase, More, PcUP1, PcUP2, phosphorylase, uridine, pynpase, pyrimidine nucleoside phosphorylase, pyrimidine phosphorylase, pyrimidine/purine nucleoside phosphorylase, StUPh, udp, UDRPase
ECTree
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Inhibitors
Inhibitors on EC 2.4.2.3 - uridine phosphorylase
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1-((2-pyrrolidine-1-yl)ethyl)uracil
inhibits both enzymic activity and growth of Plasmodium falciparum
1-(1',2'-dihydroxypropyl)-5,6-tetramethyleneuracil
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only the R-enantiomer inhibits, but not the S-enantiomer
1-(1',3'-dihydroxy-2'-propoxy)methyl-5,6-tetramethyleneuracil
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inhibits forward and reverse reaction
1-(1',3'-dihydroxy-2'-propoxy)methyl-5-benzyluracil
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i.e. DHPBU, competitive
3-((2-pyrrolidine-1-yl)ethyl)uracil
inhibits both enzymic activity and growth of Plasmodium falciparum
4-benzyl-6-hydroxy-2-oxo-1,2-dihydropyridine-3-carbonitrile
2% inhibition at 0.001 mM
4-ethyl-6-hydroxy-2-oxo-1,2-dihydropyridine-3-carbonitrile
25% inhibition at 0.001 mM
4-hydroxy-5-[[(2-hydroxyethyl)amino]methyl]-3,4-dihydropyrimidin-2(1H)-one
2% inhibition at 0.001 mM
5-Azauracil
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reaction is inhibited in the direction of deoxyuridine synthesis more than in the direction of their cleavage at the same concentration of 5-azauracil
5-benzyl-1-(2'-hydroxyethoxymethyl)uracil
competitive inhibition with respect to uridine, noncompetitive inhibition with respect to phosphate
5-benzyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
43% inhibition at 0.001 mM
5-[(diethylamino)methyl]-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
25% inhibition at 0.001 mM
5-[(dimethylamino)methyl]-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
81% inhibition at 0.001 mM
5-[[(1,3-dihydroxypropan-2-yl)amino]methyl]-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
82% inhibition at 0.001 mM
5-[[(2,3-dihydroxypropyl)amino]methyl]-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
78% inhibition at 0.001 mM
6-hydroxy-2-oxo-1,2-dihydropyridine-3-carbonitrile
67% inhibition at 0.001 mM
6-hydroxy-2-oxo-4-(propan-2-yl)-1,2-dihydropyridine-3-carbonitrile
31% inhibition at 0.001 mM
6-hydroxy-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile
42% inhibition at 0.001 mM
6-hydroxy-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile
16% inhibition at 0.001 mM
6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
70% inhibition at 0.001 mM
6-hydroxy-4-methyl-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbonitrile
12% inhibition at 0.001 mM
6-hydroxy-4-methyl-2-oxo-5-[(piperidin-1-yl)methyl]-1,2-dihydropyridine-3-carbonitrile
49% inhibition at 0.001 mM
6-hydroxy-4-methyl-5-[(morpholin-4-yl)methyl]-2-oxo-1,2-dihydropyridine-3-carbonitrile
51% inhibition at 0.001 mM
6-hydroxy-4-propyl-1H-pyridin-2-one-3-carbonitrile
16% inhibition at 0.001 mM
6-hydroxy-5-(((2-hydroxyethyl) amino) methyl)-4-methyl-1H-pyridin-2-one-3-carbonitrile
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6-hydroxy-5-(((2-hydroxyethyl)amino)methyl)-4-methyl-1H-pyridin-2-one-3-carbonitrile
80% inhibition at 0.001 mM
Acyclonucleoside analogues
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consisting of 5- and 5,6-substituted uracils and different acyclic chains
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Deoxyglucosylthymine
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phosphorolysis of uridine and deoxyuridine, synthesis of uridine at concentrations of 0.10 mM, 0.018 mM and 0.14 mM, not: phosphorolysis of deoxyuridine or thymidine at 0.19 mM
guanidine hydrochloride
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50% loss of activity at 1.04 M, only little residual activity between 2 and 6 M
potassium 5-cyano-4-methyl-6-oxo-1,6-dihydropyridin-2-olate
60% inhibition at 0.001 mM
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high-resolution three-dimensional structure of uridine phosphorylase from in complex with the competitive inhibitor determined by X-ray diffraction (PDB ID 6RCA), detailed binding structure analysis, overview. The binding of the inhibitor at the active site of the protein is energetically more favorable than the binding of the native substrate uridine. The inhibitor molecules are located in all six active sites of the hexameric UPh molecule. Effect of 2,2'-anhydrouridine binding on the conformation of structurally functional elements of VchUPh
5-benzylacyclouridine
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0.01 mM, 90% inhibition of normal tissues, 40-60% inhibition of carcinoma tissue
5-benzylacyclouridine
an UPP1-specific inhibitor. Binding of the inhibitor to the UPP1 active site, structure, overview
6-Methyluracil
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acts as a pseudosubstrate, molecular docking into the active site, molecular-dynamics simulations of the complex. Repulsion between the hydrophilic hydroxyl group of the active-site residue Thr93 of VchUPh and the hydrophobic methyl group of 6-methyluracil prevents the oxygen atom O4' of the ribose moiety and the phosphate oxygen atom O3P of ribose 1-phosphate from forming hydrogen bonds with OG1_Thr93, which are essential for the enzymatic reaction. This, apparently, renders VchUPh inactive in the enzymatic synthesis of 6-methyluridine from 6-methyluracil
product inhibition pattern, noncompetitive versus uridine, competitive versus phosphate, overview
alpha-D-ribose 1-phosphate
-
product inhibition, noncompetitive with respect to uridine and phosphate
Uracil
product inhibition pattern, noncompetitive versus uridine and phosphate, overview
Uracil
-
product inhibition, oncompetitive with respect to uridine and phosphate