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Literature summary 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

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis
4.2.1.10 (1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
 Mycobacterium tuberculosis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.1.10 0.015
-
 3-dehydroquinate at pH 7.0, 25°C Mycobacterium tuberculosis
4.2.1.10 0.48
-
 3-dehydroquinate at pH 7.0, 25°C Helicobacter pylori

Organism

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.10 3-dehydroquinate
-
 Helicobacter pylori 3-dehydroshikimate + H2O
-
 r
4.2.1.10 3-dehydroquinate
-
 Mycobacterium tuberculosis 3-dehydroshikimate + H2O
-
 r
4.2.1.10 3-dehydroquinate
-
 Mycobacterium tuberculosis H37Rv 3-dehydroshikimate + H2O
-
 r

Synonyms

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

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
4.2.1.10 0.06
-
 3-dehydroquinate at pH 7.0, 25°C Helicobacter pylori
4.2.1.10 0.15
-
 3-dehydroquinate at pH 7.0, 25°C Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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
4.2.1.10 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