BRENDA - Enzyme Database show

Heterocyclic inhibitors of dihydrodipicolinate synthase are not competitive

Turner, J.J.; Gerrard, J.A.; Hutton, C.A.; Bioorg. Med. Chem. 13, 2133-2140 (2005)

Data extracted from this reference:

Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
4.3.3.7
(1SR,3R,5S)-1-hydroxy-3,5-bis(methoxycarbonyl)thiomorpholin-1-ium
30 mM, 18% inhibition
Escherichia coli
4.3.3.7
(1SS,3R,5S)-1-hydroxy-3,5-bis(methoxycarbonyl)thiomorpholin-1-ium
9 mM, 48% inhibition
Escherichia coli
4.3.3.7
(2R,6S)-piperidine-2,6-dicarboxylic acid
IC50: 20 mM, 83% inhibition at 50 mM
Escherichia coli
4.3.3.7
(3R,5R)-thiomorpholine-3,5-dicarboxylic acid
50 mM, 32% inhibition
Escherichia coli
4.3.3.7
(3R,5R)-thiomorpholine-3,5-dicarboxylic acid 1,1-dioxide
50 mM, 11% inhibition
Escherichia coli
4.3.3.7
(3R,5S)-thiomorpholine-3,5-dicarboxylic acid 1,1-dioxide
50 mM, 14% inhibition
Escherichia coli
4.3.3.7
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
i.e. chelidamic acid, IC50: 22 mM, 99% inhibition at 50 mM, uncompetitive inhibitor with respect to both substrates
Escherichia coli
4.3.3.7
dimethyl (3R,5R)-thiomorpholine-3,5-dicarboxylate 1,1-dioxide
50 mM, 12% inhibition
Escherichia coli
4.3.3.7
dimethyl (3R,5S)-thiomorpholine-3,5-dicarboxylate
50 mM, 36% inhibition
Escherichia coli
4.3.3.7
dimethyl chelidamate
IC50: 14 mM. 99% inhibition at 50 mM, noncompetitive with respect to both substrates
Escherichia coli
4.3.3.7
dimethyl piperidine-2,6-dicarboxylate
-
Escherichia coli
4.3.3.7
dipicolinic acid
IC50: 20 mM, competitive inhibitor
Escherichia coli
4.3.3.7
additional information
no inhibition by dipicolinic acid methyl ester, (3R,5S)-thiomorpholine-3,5-dicarboxylic acid compound 20b, (3R,5R)-thiomorpholine-3,5-dicarboxylic acid, compound 23, compound 24b, dimethyl (3R,5S)thiomorpholine-3,5-dicarboxylate 1,1-dioxide
Escherichia coli
KM Value [mM]
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
4.3.3.7
0.14
-
L-aspartate 4-semialdehyde
pH 8.0
Escherichia coli
4.3.3.7
0.38
-
pyruvate
pH 8.0
Escherichia coli
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
4.3.3.7
Escherichia coli
-
-
-
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
4.3.3.7
L-aspartate 4-semialdehyde + pyruvate
-
664304
Escherichia coli
dihydrodipicolinate + H2O
-
-
-
?
Ki Value [mM]
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
4.3.3.7
6.9
-
dimethyl chelidamate
with respect to pyruvate
Escherichia coli
4.3.3.7
14
-
dimethyl chelidamate
with respect to L-aspartate 4-semialdehyde
Escherichia coli
4.3.3.7
22
-
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
with respect to pyruvate
Escherichia coli
4.3.3.7
24.8
-
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
with respect to L-aspartate 4-semialdehyde
Escherichia coli
IC50 Value
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
4.3.3.7
14
-
IC50: 14 mM. 99% inhibition at 50 mM, noncompetitive with respect to both substrates
Escherichia coli
dimethyl chelidamate
4.3.3.7
20
-
IC50: 20 mM, 83% inhibition at 50 mM
Escherichia coli
(2R,6S)-piperidine-2,6-dicarboxylic acid
4.3.3.7
20
-
IC50: 20 mM, competitive inhibitor
Escherichia coli
dipicolinic acid
4.3.3.7
22
-
i.e. chelidamic acid, IC50: 22 mM, 99% inhibition at 50 mM, uncompetitive inhibitor with respect to both substrates
Escherichia coli
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
IC50 Value (protein specific)
EC Number
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
4.3.3.7
14
-
IC50: 14 mM. 99% inhibition at 50 mM, noncompetitive with respect to both substrates
Escherichia coli
dimethyl chelidamate
4.3.3.7
20
-
IC50: 20 mM, 83% inhibition at 50 mM
Escherichia coli
(2R,6S)-piperidine-2,6-dicarboxylic acid
4.3.3.7
20
-
IC50: 20 mM, competitive inhibitor
Escherichia coli
dipicolinic acid
4.3.3.7
22
-
i.e. chelidamic acid, IC50: 22 mM, 99% inhibition at 50 mM, uncompetitive inhibitor with respect to both substrates
Escherichia coli
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
4.3.3.7
(1SR,3R,5S)-1-hydroxy-3,5-bis(methoxycarbonyl)thiomorpholin-1-ium
30 mM, 18% inhibition
Escherichia coli
4.3.3.7
(1SS,3R,5S)-1-hydroxy-3,5-bis(methoxycarbonyl)thiomorpholin-1-ium
9 mM, 48% inhibition
Escherichia coli
4.3.3.7
(2R,6S)-piperidine-2,6-dicarboxylic acid
IC50: 20 mM, 83% inhibition at 50 mM
Escherichia coli
4.3.3.7
(3R,5R)-thiomorpholine-3,5-dicarboxylic acid
50 mM, 32% inhibition
Escherichia coli
4.3.3.7
(3R,5R)-thiomorpholine-3,5-dicarboxylic acid 1,1-dioxide
50 mM, 11% inhibition
Escherichia coli
4.3.3.7
(3R,5S)-thiomorpholine-3,5-dicarboxylic acid 1,1-dioxide
50 mM, 14% inhibition
Escherichia coli
4.3.3.7
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
i.e. chelidamic acid, IC50: 22 mM, 99% inhibition at 50 mM, uncompetitive inhibitor with respect to both substrates
Escherichia coli
4.3.3.7
dimethyl (3R,5R)-thiomorpholine-3,5-dicarboxylate 1,1-dioxide
50 mM, 12% inhibition
Escherichia coli
4.3.3.7
dimethyl (3R,5S)-thiomorpholine-3,5-dicarboxylate
50 mM, 36% inhibition
Escherichia coli
4.3.3.7
dimethyl chelidamate
IC50: 14 mM. 99% inhibition at 50 mM, noncompetitive with respect to both substrates
Escherichia coli
4.3.3.7
dimethyl piperidine-2,6-dicarboxylate
-
Escherichia coli
4.3.3.7
dipicolinic acid
IC50: 20 mM, competitive inhibitor
Escherichia coli
4.3.3.7
additional information
no inhibition by dipicolinic acid methyl ester, (3R,5S)-thiomorpholine-3,5-dicarboxylic acid compound 20b, (3R,5R)-thiomorpholine-3,5-dicarboxylic acid, compound 23, compound 24b, dimethyl (3R,5S)thiomorpholine-3,5-dicarboxylate 1,1-dioxide
Escherichia coli
Ki Value [mM] (protein specific)
EC Number
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
4.3.3.7
6.9
-
dimethyl chelidamate
with respect to pyruvate
Escherichia coli
4.3.3.7
14
-
dimethyl chelidamate
with respect to L-aspartate 4-semialdehyde
Escherichia coli
4.3.3.7
22
-
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
with respect to pyruvate
Escherichia coli
4.3.3.7
24.8
-
4-oxo-1,4-dihydropyridine-2,6-dicarboxylic acid
with respect to L-aspartate 4-semialdehyde
Escherichia coli
KM Value [mM] (protein specific)
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
4.3.3.7
0.14
-
L-aspartate 4-semialdehyde
pH 8.0
Escherichia coli
4.3.3.7
0.38
-
pyruvate
pH 8.0
Escherichia coli
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
4.3.3.7
L-aspartate 4-semialdehyde + pyruvate
-
664304
Escherichia coli
dihydrodipicolinate + H2O
-
-
-
?