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Literature summary for 4.2.1.10 extracted from

  • Prazeres, V.; Castedo, L.; Lamb, H.; Hawkins, A.; González-Bello, C.
    2-Substituted-3-dehydroquinic acids as potent competitive inhibitors of type II dehydroquinase (2009), ChemMedChem, 4, 1980-1984.
    View publication on PubMed
Search for more literature for 4.2.1.10

Inhibitors

Inhibitors Comment Organism Structure
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.015
-
 3-dehydroquinate at pH 7.0, 25°C Mycobacterium tuberculosis
0.48
-
 3-dehydroquinate at pH 7.0, 25°C Helicobacter pylori

Organism

Organism UniProt Comment Textmining
Helicobacter pylori Q48255
-
-
Mycobacterium tuberculosis P9WPX7
-
-
Mycobacterium tuberculosis H37Rv P9WPX7
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3-dehydroquinate
-
 Helicobacter pylori 3-dehydroshikimate + H2O
-
 r
3-dehydroquinate
-
 Mycobacterium tuberculosis 3-dehydroshikimate + H2O
-
 r
3-dehydroquinate
-
 Mycobacterium tuberculosis H37Rv 3-dehydroshikimate + H2O
-
 r

Synonyms

Synonyms Comment Organism
DHQ2
-
 Helicobacter pylori
DHQ2
-
 Mycobacterium tuberculosis
Type II dehydroquinase
-
 Helicobacter pylori
Type II dehydroquinase
-
 Mycobacterium tuberculosis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.06
-
 3-dehydroquinate at pH 7.0, 25°C Helicobacter pylori
0.15
-
 3-dehydroquinate at pH 7.0, 25°C Mycobacterium tuberculosis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000026
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.000028
-
 (1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.000047
-
 (1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.000056
-
 (1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.000074
-
 (1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.000089
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.00009
-
 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.00009
-
 (1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.0001
-
 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.0001
-
 (1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris·HCl Mycobacterium tuberculosis
0.00016
-
 (1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00017
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00025
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00076
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.0009
-
 (1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00097
-
 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00097
-
 (1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00118
-
 (1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.0014
-
 (1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.00142
-
 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.0017
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.00185
-
 (1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HOAc Mycobacterium tuberculosis
0.0026
-
 (1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.0093
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.02
-
 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.0215
-
 (1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori