BRENDA - Enzyme Database
show all sequences of 1.3.1.14

Latent Inhibitors. Part 4. Irreversible inhibition of dihydro-orotate dehydrogenase by hydantoins derived from amino acids

Buntain, I.G.; Suckling, C.J.; Wood, H.C.S.; J. Chem. Soc. Perkin Trans. I 1988, 3175-3182 (1988)
No PubMed abstract available

Data extracted from this reference:

Application
Application
Commentary
Organism
medicine
enzyme is a part of the pyrimidine biosynthesis pathway and plays a role as target for the chemotherapy of parasitic and neoplastic diseases
Faecalicatena orotica
pharmacology
drug design based upon selective enzyme inhibition
Faecalicatena orotica
General Stability
General Stability
Organism
dithiothreitol stabilizes
Faecalicatena orotica
Inhibitors
Inhibitors
Commentary
Organism
Structure
(R,R)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
(S)-5-benzyl-3-carboxymethylhydantoin
-
Faecalicatena orotica
(S)-N-carboxymethyl-N'-(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
(S,S)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
(S,S)-N,N'-bis(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
(S,S)-N-(1-carboxyethyl)-N'-(1-carboxy-2-phenylethyl)urea
4 mM, 20% inhibition
Faecalicatena orotica
3-carboxymethylhydantoin
-
Faecalicatena orotica
5-benzyl-3-(1-carboxy-2-phenylethyl)-1-methylhydantoin
-
Faecalicatena orotica
5-Benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
time-dependent irreversible inhibition at the active site, mechanism
Faecalicatena orotica
hydantoin
derived from alpha-amino acids, weak competitive inhibitors, compounds with a benzyl goup are better inhibitors
Faecalicatena orotica
isopropyl hydantoin
-
Faecalicatena orotica
N,N'-bis(carboxymethyl)urea
-
Faecalicatena orotica
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
dihydroorotate + NAD+
Faecalicatena orotica
biosynthesis of pyrimidines
orotate + NADH + H+
-
Faecalicatena orotica
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Faecalicatena orotica
-
identical with Clostridium oroticum
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(S)-dihydroorotate + NAD+
-
390565
Faecalicatena orotica
orotate + NADH + H+
-
390565
Faecalicatena orotica
?
dihydroorotate + NAD+
biosynthesis of pyrimidines
390565
Faecalicatena orotica
orotate + NADH + H+
-
390565
Faecalicatena orotica
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Faecalicatena orotica
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
-
pH of assay medium
Faecalicatena orotica
Cofactor
Cofactor
Commentary
Organism
Structure
flavin
flavoprotein with two different flavins, probably FAD and FMN; NAD+-linked flavoprotein
Faecalicatena orotica
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.4
-
(S,S)-N,N'-bis(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
0.6
-
5-benzyl-3-(1-carboxy-2-phenylethyl)-1-methylhydantoin
-
Faecalicatena orotica
0.7
-
(S)-N-carboxymethyl-N'-(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
0.7
-
(S,S)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
0.9
-
(R,R)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
2.3
-
(S)-5-benzyl-3-carboxymethylhydantoin
-
Faecalicatena orotica
2.6
-
N,N'-bis(carboxymethyl)urea
-
Faecalicatena orotica
4.5
-
3-carboxymethylhydantoin
-
Faecalicatena orotica
Application (protein specific)
Application
Commentary
Organism
medicine
enzyme is a part of the pyrimidine biosynthesis pathway and plays a role as target for the chemotherapy of parasitic and neoplastic diseases
Faecalicatena orotica
pharmacology
drug design based upon selective enzyme inhibition
Faecalicatena orotica
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
flavin
flavoprotein with two different flavins, probably FAD and FMN; NAD+-linked flavoprotein
Faecalicatena orotica
General Stability (protein specific)
General Stability
Organism
dithiothreitol stabilizes
Faecalicatena orotica
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(R,R)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
(S)-5-benzyl-3-carboxymethylhydantoin
-
Faecalicatena orotica
(S)-N-carboxymethyl-N'-(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
(S,S)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
(S,S)-N,N'-bis(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
(S,S)-N-(1-carboxyethyl)-N'-(1-carboxy-2-phenylethyl)urea
4 mM, 20% inhibition
Faecalicatena orotica
3-carboxymethylhydantoin
-
Faecalicatena orotica
5-benzyl-3-(1-carboxy-2-phenylethyl)-1-methylhydantoin
-
Faecalicatena orotica
5-Benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
time-dependent irreversible inhibition at the active site, mechanism
Faecalicatena orotica
hydantoin
derived from alpha-amino acids, weak competitive inhibitors, compounds with a benzyl goup are better inhibitors
Faecalicatena orotica
isopropyl hydantoin
-
Faecalicatena orotica
N,N'-bis(carboxymethyl)urea
-
Faecalicatena orotica
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.4
-
(S,S)-N,N'-bis(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
0.6
-
5-benzyl-3-(1-carboxy-2-phenylethyl)-1-methylhydantoin
-
Faecalicatena orotica
0.7
-
(S)-N-carboxymethyl-N'-(1-carboxy-2-phenylethyl)urea
-
Faecalicatena orotica
0.7
-
(S,S)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
0.9
-
(R,R)-5-benzyl-3-(1-carboxy-2-phenylethyl)hydantoin
-
Faecalicatena orotica
2.3
-
(S)-5-benzyl-3-carboxymethylhydantoin
-
Faecalicatena orotica
2.6
-
N,N'-bis(carboxymethyl)urea
-
Faecalicatena orotica
4.5
-
3-carboxymethylhydantoin
-
Faecalicatena orotica
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
dihydroorotate + NAD+
Faecalicatena orotica
biosynthesis of pyrimidines
orotate + NADH + H+
-
Faecalicatena orotica
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
(S)-dihydroorotate + NAD+
-
390565
Faecalicatena orotica
orotate + NADH + H+
-
390565
Faecalicatena orotica
?
dihydroorotate + NAD+
biosynthesis of pyrimidines
390565
Faecalicatena orotica
orotate + NADH + H+
-
390565
Faecalicatena orotica
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Faecalicatena orotica
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
-
pH of assay medium
Faecalicatena orotica
Other publictions for EC 1.3.1.14
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
701809
Kawasaki
b-Type dihydroorotate dehydrog ...
Bifidobacterium bifidum
Appl. Environ. Microbiol.
75
629-636
2009
-
-
-
-
-
-
4
-
-
-
1
-
-
4
-
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1
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-
-
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1
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-
-
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2
1
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2
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2
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4
-
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1
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1
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-
-
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1
-
-
-
-
2
1
-
-
-
-
-
-
-
-
674586
Combe
Lys-D48 is required for charge ...
Lactococcus lactis
J. Biol. Chem.
281
17977-17988
2006
-
-
-
-
4
-
-
9
-
-
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-
-
1
-
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1
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9
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3
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3
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4
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9
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1
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-
9
-
-
-
-
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-
-
-
-
-
654759
Mohsen
Thermodynamic basis of electro ...
Lactococcus lactis
Biochemistry
43
6498-6510
2004
-
-
-
-
-
-
-
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-
-
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1
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1
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1
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3
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1
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-
-
-
390568
Argyrou
Dihydroorotate dehydrogenase f ...
Bacillus subtilis, Enterococcus faecalis, Faecalicatena orotica, Lactococcus lactis
Biochemistry
39
10373-10384
2000
6
-
2
-
-
-
-
2
4
-
3
3
-
4
-
-
1
3
-
-
1
1
13
3
1
-
-
3
-
1
-
12
-
-
-
6
-
2
12
-
-
-
-
-
-
2
4
-
3
3
-
-
-
1
-
-
1
1
13
3
1
-
-
3
-
1
-
-
-
-
-
-
-
-
390569
Rowland
Structure of dihydroorotate de ...
Bacillus subtilis, Enterococcus faecalis, Faecalicatena orotica, Lactococcus lactis
Structure
8
1227-1238
2000
-
5
-
1
-
-
-
-
4
-
-
3
-
4
-
-
1
1
-
-
-
-
11
3
-
-
-
-
-
-
-
12
-
-
-
-
5
-
12
1
-
-
-
-
-
-
4
-
-
3
-
-
-
1
-
-
-
-
11
3
-
-
-
-
-
-
-
-
-
-
-
-
-
-
390928
Kahler
Biochemical characterization o ...
Bacillus subtilis, Mus musculus
Arch. Biochem. Biophys.
371
191-201
1999
-
-
1
-
5
-
1
3
-
-
8
1
-
2
-
-
1
1
1
-
-
3
5
1
-
-
-
-
-
-
-
3
2
-
-
-
-
1
3
-
5
-
-
1
2
3
-
-
8
1
-
-
-
1
1
-
-
3
5
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
391244
Marcinkeviciene
Dihydroorotate dehydrogenase B ...
Enterococcus faecalis
Biochemistry
38
13129-13137
1999
-
-
-
-
-
-
-
-
-
-
3
-
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3
-
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1
1
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2
1
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1
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1
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3
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1
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2
1
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-
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-
-
-
390917
Andersen
Two different dihydroorotate d ...
Lactococcus lactis
J. Bacteriol.
176
3975-3982
1994
-
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1
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-
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1
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2
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4
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4
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1
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2
1
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1
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-
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4
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4
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390565
Buntain
-
Latent Inhibitors. Part 4. Irr ...
Faecalicatena orotica
J. Chem. Soc. Perkin Trans. I
1988
3175-3182
1988
-
2
-
-
-
1
12
-
-
-
-
1
-
1
-
-
-
-
-
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-
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2
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1
-
-
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1
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1
8
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2
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1
-
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1
-
12
8
-
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-
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1
-
-
-
-
-
-
-
-
2
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
390564
Friedmann
-
Bestimmung mit Dihydroorotat-D ...
Faecalicatena orotica
Methods Enzym. Anal. , 3rd Ed. (Bergmeyer, H. U. , ed. )
2
2010-2014
1984
1
-
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4
2
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1
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1
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1
3
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1
1
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4
1
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1
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4
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4
1
2
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1
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1
3
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1
1
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-
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-
-
-
390563
Blattmann
Stereospecificity of the dihyd ...
Faecalicatena orotica
Eur. J. Biochem.
30
130-137
1972
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1
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1
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1
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1
1
2
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390567
Nelson
Preparation of bovine xanthine ...
Faecalicatena orotica
J. Biol. Chem.
243
5368-5373
1968
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1
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1
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1
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390566
Friedmann
Crystalline dihydroorotic dehy ...
Faecalicatena orotica
J. Biol. Chem.
235
1526-1530
1960
1
-
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1
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5
-
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1
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1
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1
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1
1
2
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2
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1
1
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4
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1
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4
1
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5
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1
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1
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1
1
2
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2
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1
1
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390561
Friedmann
Purification and properties of ...
Faecalicatena orotica
J. Biol. Chem.
233
1398-1406
1958
3
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5
2
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1
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1
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1
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1
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5
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1
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3
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3
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3
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5
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2
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1
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1
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1
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5
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1
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390562
Lieberman
Enzymic synthesis and breakdow ...
Faecalicatena orotica
Biochim. Biophys. Acta
12
223-234
1953
1
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1
1
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1
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1
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