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Literature summary for 4.2.1.10 extracted from

  • Tran, A.; Cergol, K.; West, N.; Randall, E.; Britton, W.; Bokhari, S.; Ibrahim, M.; Lapthorn, A.; Payne, R.
    Synthesis and evaluation of potent ene-yne inhibitors of type II dehydroquinases as tuberculosis drug leads (2011), ChemMedChem, 6, 262-265.
    View publication on PubMed
Search for more literature for 4.2.1.10

Inhibitors

Inhibitors Comment Organism Structure
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Streptomyces coelicolor
additional information development of a range of ene-yne-based inhibitors, active site docking study using enzyme structure PDB ID 2WKS, overview Helicobacter pylori
additional information development of a range of ene-yne-based inhibitors, overview Mycobacterium tuberculosis
additional information development of a range of ene-yne-based inhibitors, active site docking study using enzyme structure PDB ID 1GU1, overview Streptomyces coelicolor

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.036
-
 3-dehydroquinate pH 7.5, 25°C Mycobacterium tuberculosis
0.075
-
 3-dehydroquinate pH 7.5, 25°C Helicobacter pylori
0.21
-
 3-dehydroquinate pH 7.5, 25°C Streptomyces coelicolor

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Helicobacter pylori Q48255
-
-
Mycobacterium tuberculosis
-
-
-
Streptomyces coelicolor P15474
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
dehydroquinase
-
 Mycobacterium tuberculosis
dehydroquinase
-
 Streptomyces coelicolor
dehydroquinase
-
 Helicobacter pylori
DHQase
-
 Mycobacterium tuberculosis
DHQase
-
 Streptomyces coelicolor
DHQase
-
 Helicobacter pylori

Temperature Optimum [°C]

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

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.34
-
 3-dehydroquinate pH 7.5, 25°C Helicobacter pylori
4.6
-
 3-dehydroquinate pH 7.5, 25°C Mycobacterium tuberculosis
61
-
 3-dehydroquinate pH 7.5, 25°C Streptomyces coelicolor

pH Optimum

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

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0000022
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
0.0000069
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
0.0000071
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.0000075
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000012
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000028
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000094
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000098
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
0.000103
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
0.000106
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000108
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
0.000126
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000133
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
0.000168
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000171
-
 pH 7.5, 25°C Streptomyces coelicolor (1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000187
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000253
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000316
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000356
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000548
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000712
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000885
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.001203
-
 pH 7.5, 25°C Helicobacter pylori (1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.002194
-
 pH 7.5, 25°C Mycobacterium tuberculosis (1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid

General Information

General Information Comment Organism
metabolism dehydroquinase catalyzes the third step in the shikimate pathway, the reversible dehydration of 3-dehydroquinate to 3-dehydroshikimate Mycobacterium tuberculosis
metabolism dehydroquinase catalyzes the third step in the shikimate pathway, the reversible dehydration of 3-dehydroquinate to 3-dehydroshikimate Streptomyces coelicolor
metabolism dehydroquinase catalyzes the third step in the shikimate pathway, the reversible dehydration of 3-dehydroquinate to 3-dehydroshikimate Helicobacter pylori