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Literature summary extracted from

  • Tran, A.; Cergol, K.; Britton, W.; Imran Bokhari, S.; Ibrahim, M.; Lapthorn, A.; Payne, R.
    Rapid assembly of potent type II dehydroquinase inhibitors via 'click' chemistry (2010), MedChemComm, 1, 271-275.
No PubMed abstract available

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 (1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 (1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 (1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Streptomyces coelicolor
4.2.1.10 3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid competitive inhibitor Helicobacter pylori
4.2.1.10 3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid competitive inhibitor Mycobacterium tuberculosis
4.2.1.10 3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid competitive inhibitor Streptomyces coelicolor

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.1.10 0.052
-
 3-dehydroquinate pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.0769
-
 3-dehydroquinate pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.228
-
 3-dehydroquinate pH 7.5, 25°C Helicobacter pylori

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.10 3-dehydroquinate Mycobacterium tuberculosis
-
 3-dehydroshikimate + H2O
-
 r
4.2.1.10 3-dehydroquinate Streptomyces coelicolor
-
 3-dehydroshikimate + H2O
-
 r
4.2.1.10 3-dehydroquinate Helicobacter pylori
-
 3-dehydroshikimate + H2O
-
 r

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.10 Helicobacter pylori
-
-
-
4.2.1.10 Mycobacterium tuberculosis
-
-
-
4.2.1.10 Streptomyces coelicolor
-
-
-

Substrates and Products (Substrate)

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

Synonyms

EC Number Synonyms Comment Organism
4.2.1.10 Type II dehydroquinase
-
 Mycobacterium tuberculosis
4.2.1.10 Type II dehydroquinase
-
 Streptomyces coelicolor
4.2.1.10 Type II dehydroquinase
-
 Helicobacter pylori
4.2.1.10 Type II DHQase
-
 Mycobacterium tuberculosis
4.2.1.10 Type II DHQase
-
 Streptomyces coelicolor
4.2.1.10 Type II DHQase
-
 Helicobacter pylori

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.10 25
-
 assay at Mycobacterium tuberculosis
4.2.1.10 25
-
 assay at Streptomyces coelicolor
4.2.1.10 25
-
 assay at Helicobacter pylori

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
4.2.1.10 1.4
-
 3-dehydroquinate pH 7.5, 25°C Helicobacter pylori
4.2.1.10 6.3
-
 3-dehydroquinate pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 84
-
 3-dehydroquinate pH 7.5, 25°C Streptomyces coelicolor

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.10 7.5
-
 assay at Mycobacterium tuberculosis
4.2.1.10 7.5
-
 assay at Streptomyces coelicolor
4.2.1.10 7.5
-
 assay at Helicobacter pylori

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.2.1.10 0.0000057
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.0000057
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.000029
-
 (1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.000039
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.000048
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.000073
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.000078
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.000136
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.000154
-
 (1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.000157
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.000217
-
 (1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.000225
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.00023
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.00033
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.000375
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.000538
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.000561
-
 (1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.000925
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.001579
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.00172
-
 3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid pH 7.5, 25°C Streptomyces coelicolor
4.2.1.10 0.002122
-
 (1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.0022
-
 (1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid pH 7.5, 25°C Helicobacter pylori
4.2.1.10 0.003126
-
 3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid pH 7.5, 25°C Mycobacterium tuberculosis
4.2.1.10 0.00578
-
 3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid pH 7.5, 25°C Helicobacter pylori