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(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-[(4-nitrophenyl)methyl]pyrrolidin-1-ium
(1S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-[2-(4-nitrophenyl)ethyl]pyrrolidin-1-ium
(2R,3R,4S)-1-[2-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-ium
(2R,3R,4S)-1-[2-(6-carboxy-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-ium
(2R,3S)-3-hydroxy-2-(hydroxymethyl)-5-(4-nitrophenyl)pyrrolidin-1-ium
(2S,3S,4R,5R)-2-[(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium
(2S,3S,4R,5R)-2-[(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium
(3R,4R)-1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-ium
(3R,4R)-1-[2-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-ium
(7R,8R,9S,9aS)-8,9-dihydroxy-7-(hydroxymethyl)-8,9,9a,10-tetrahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-c]pyrimidine-1,3,5(2H)-trione
1,3-dihydroxy-N-[(4-nitrophenyl)methyl]propan-2-aminium
1,3-dihydroxy-N-[2-(4-nitrophenyl)ethyl]propan-2-aminium
1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]pyrrolidin-1-ium
2,6-dihydroxypyridine-4-carboxylic acid
-
competitive to orotate, uncompetitive to 5-phospho-alpha-D-ribose 1-diphosphate
3-(2-hydroxybenzylidene)-2,6-dioxo-1,2,3,6-tetrahydropyridine-4-carboxylic acid
-
competitive to orotate, uncompetitive to 5-phospho-alpha-D-ribose 1-diphosphate
3-benzylidene-2,6-dioxo-1,2,3,6-tetrahydropyridine-4-carboxylic acid
-
competitive to orotate, uncompetitive to 5-phospho-alpha-D-ribose 1-diphosphate
4-nitrophenyl beta-D-ribose
4-nitrophenyl beta-D-ribose 5'-phosphate
5-aminoorotate
50% inhibition at 0.01 mM
5-fluorouracil
50% inhibition at 0.005-0.01 mM
5-Methylorotate
50% inhibition at 0.001 mM
5-phospho-alpha-D-ribose 1-diphosphate
6-hydroxy-5-((2-hydroxyethylamino)methyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid
-
competitive to orotate, uncompetitive to 5-phospho-alpha-D-ribose 1-diphosphate
arabinose 5-phosphate
-
at higher concentrations
Co2+
-
inhibits Mg2+-activation
erythrose 4-phosphate
-
at higher concentrations
fructose 1-phosphate
-
at higher concentrations
fructose 6-phosphate
-
at higher concentrations
HgCl2
-
slight inhibition of mutant, not wild-type
iodoacetamide
-
slight inhibition of mutant, not wild-type
NEM
-
slight inhibition of mutant, not wild-type
Orotic acid
-
when grown on glucose as carbon source, supplementation with orotic acid significantly decreases orotate phosphoribosyltransferase and orotidine 5'-monophoshate decarboxylase activities. In a strain deficient for dihydroorotase activity, orotic acid induces both phosphoribosyltransferase and orotidine 5'-monophoshate decarboxylase activites
p-nitrophenyl beta-D-ribose
p-nitrophenyl beta-D-ribose 5'-phosphate
pyrazofurin
50% inhibition at 0.006-0.024 mM
xanthosine-5'-phosphate
-
-
[(2R,3R,4S,5S)-5-(4-carboxypyridin-3-yl)-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
[(2R,3R,4S,5S)-5-[(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
[(2R,3R,4S,5S)-5-[(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
[(3R,4R)-1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-4-hydroxypyrrolidin-1-ium-3-yl]methyl hydrogen phosphate
[(7R,8R,9S,9aS)-8,9-dihydroxy-1,3,5-trioxo-1,2,3,5,8,9,9a,10-octahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-c]pyrimidin-7-yl]methyl hydrogen phosphate
(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-[(4-nitrophenyl)methyl]pyrrolidin-1-ium
-
-
(1R,3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-[(4-nitrophenyl)methyl]pyrrolidin-1-ium
-
-
(1S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-[2-(4-nitrophenyl)ethyl]pyrrolidin-1-ium
-
-
(1S,3R,4R)-3-hydroxy-4-(hydroxymethyl)-1-[2-(4-nitrophenyl)ethyl]pyrrolidin-1-ium
-
-
(2R,3R,4S)-1-[2-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2R,3R,4S)-1-[2-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2R,3R,4S)-1-[2-(6-carboxy-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2R,3R,4S)-1-[2-(6-carboxy-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2R,3S)-3-hydroxy-2-(hydroxymethyl)-5-(4-nitrophenyl)pyrrolidin-1-ium
-
-
(2R,3S)-3-hydroxy-2-(hydroxymethyl)-5-(4-nitrophenyl)pyrrolidin-1-ium
-
-
(2S,3S,4R,5R)-2-[(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2S,3S,4R,5R)-2-[(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2S,3S,4R,5R)-2-[(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium
-
-
(2S,3S,4R,5R)-2-[(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-1-ium
-
-
(3R,4R)-1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-ium
-
-
(3R,4R)-1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-ium
-
-
(3R,4R)-1-[2-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-ium
-
-
(3R,4R)-1-[2-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl]-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-ium
-
-
(7R,8R,9S,9aS)-8,9-dihydroxy-7-(hydroxymethyl)-8,9,9a,10-tetrahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-c]pyrimidine-1,3,5(2H)-trione
-
-
(7R,8R,9S,9aS)-8,9-dihydroxy-7-(hydroxymethyl)-8,9,9a,10-tetrahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-c]pyrimidine-1,3,5(2H)-trione
-
-
1,3-dihydroxy-N-[(4-nitrophenyl)methyl]propan-2-aminium
-
-
1,3-dihydroxy-N-[(4-nitrophenyl)methyl]propan-2-aminium
-
-
1,3-dihydroxy-N-[2-(4-nitrophenyl)ethyl]propan-2-aminium
-
-
1,3-dihydroxy-N-[2-(4-nitrophenyl)ethyl]propan-2-aminium
-
-
1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]pyrrolidin-1-ium
-
-
1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]pyrrolidin-1-ium
-
-
4-nitrophenyl beta-D-ribose
-
-
4-nitrophenyl beta-D-ribose
-
-
4-nitrophenyl beta-D-ribose 5'-phosphate
-
-
4-nitrophenyl beta-D-ribose 5'-phosphate
-
-
5-Fluoroorotate
-
at 0.05 M
5-Fluoroorotate
50% inhibition at 2-10 nM
5-phospho-alpha-D-ribose 1-diphosphate
product inhibition, competitive to diphosphate, competitive to orotidine 5'-phosphate
5-phospho-alpha-D-ribose 1-diphosphate
-
phosphorolysis, product inhibition, kinetics
5-phospho-alpha-D-ribose 1-diphosphate
-
phosphorolysis, product inhibition, kinetics
adenine
-
not inhibitory
adenosine
-
not inhibitory
ADP
-
not inhibitory
AMP
-
not inhibitory
ATP
-
not inhibitory
diphosphate
-
-
diphosphate
product inhibition
diphosphate
product inhibition, noncompetitive to orotate, competitive to 5-phospho-alpha-D-ribose 1-diphosphate
diphosphate
noncompetitive inhibition versus orotate, and noncompetitive versus 5-phospho-alpha-D-ribose 1-diphosphate with the bifunctional enzyme form, while competitive with the monofunctional and multienzyme form
diphosphate
-
product inhibition, kinetics
diphosphate
-
product inhibition, kinetics
EDTA
-
5 mM, complete inhibition
Orotate
product inhibition, noncompetitive to diphosphate, competitive to orotidine 5'-phosphate
Orotate
-
phosphorolysis, product inhibition, kinetics
Orotate
-
phosphorolysis, product inhibition, kinetics
orotidine 5'-phosphate
product inhibition
orotidine 5'-phosphate
product inhibition, competitive to 5-phospho-alpha-D-ribose 1-diphosphate, competitive to orotate
orotidylate
-
-
orotidylate
-
product inhibition, kinetics
orotidylate
-
product inhibition, kinetics
p-nitrophenyl beta-D-ribose
-
-
p-nitrophenyl beta-D-ribose
-
-
p-nitrophenyl beta-D-ribose 5'-phosphate
-
competitive inhibitor against orotidine 5'-phosphate
p-nitrophenyl beta-D-ribose 5'-phosphate
-
competitive inhibitor against orotidine 5'-phosphate
PCMB
-
reversible by DTT
PCMB
-
0.01 mM, complete inhibition
phosphate
-
-
phosphate
-
at higher concentrations
ribose 5-phosphate
-
not inhibitory
ribose 5-phosphate
-
at higher concentrations
sulfate
-
competitive to diphosphate
sulfate
-
competitive to diphosphate
UDP
-
-
UMP
-
1 mM, not 0.1 mM
Uracil
-
-
UTP
-
not inhibitory
[(2R,3R,4S,5S)-5-(4-carboxypyridin-3-yl)-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
-
-
[(2R,3R,4S,5S)-5-(4-carboxypyridin-3-yl)-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
-
-
[(2R,3R,4S,5S)-5-[(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
-
-
[(2R,3R,4S,5S)-5-[(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
-
-
[(2R,3R,4S,5S)-5-[(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
-
-
[(2R,3R,4S,5S)-5-[(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]-3,4-dihydroxypyrrolidin-1-ium-2-yl]methyl hydrogen phosphate
-
-
[(3R,4R)-1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-4-hydroxypyrrolidin-1-ium-3-yl]methyl hydrogen phosphate
-
-
[(3R,4R)-1-[(6-carboxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]-4-hydroxypyrrolidin-1-ium-3-yl]methyl hydrogen phosphate
-
-
[(7R,8R,9S,9aS)-8,9-dihydroxy-1,3,5-trioxo-1,2,3,5,8,9,9a,10-octahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-c]pyrimidin-7-yl]methyl hydrogen phosphate
-
-
[(7R,8R,9S,9aS)-8,9-dihydroxy-1,3,5-trioxo-1,2,3,5,8,9,9a,10-octahydro-7H-pyrrolo[1',2':4,5]pyrazino[1,2-c]pyrimidin-7-yl]methyl hydrogen phosphate
-
-
additional information
-
no inhibition by SH-group reagents
-
additional information
-
not inhibitory: CMP, TMP, 6-aza-UMP or 5-bromo-UMP
-
additional information
-
no inhibition by SH-group reagents
-
additional information
-
structural features of pyrimidine nucleobase inhibitors
-