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Literature summary for 4.2.1.10 extracted from

  • Blanco, B.; Sedes, A.; Peon, A.; Otero, J.M.; van Raaij, M.J.; Thompson, P.; Hawkins, A.R.; Gonzalez-Bello, C.
    Exploring the water-binding pocket of the type II dehydroquinase enzyme in the structure-based design of inhibitors (2014), J. Med. Chem., 57, 3494-3510.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
in complex with inhibitors, using 32% (v/v) 2-methyl-2,4-pentanediol, 0.3 M ammonium sulfate and 0.1 M 4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid sodium salt, pH 7.5 Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
-
Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
-
Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
-
Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
-
Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Mycobacterium tuberculosis
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Helicobacter pylori
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
Mycobacterium tuberculosis
(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
(1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
(1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Helicobacter pylori
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid competitive inhibitor Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

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

Organism

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

Substrates and Products (Substrate)

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

Synonyms

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

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00048
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Mycobacterium tuberculosis
0.0105
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.0112
-
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Mycobacterium tuberculosis
0.0145
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Mycobacterium tuberculosis
0.015
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Mycobacterium tuberculosis
0.027
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Mycobacterium tuberculosis
0.033
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.034
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Mycobacterium tuberculosis
0.037
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.0405
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.188
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori
0.282
-
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid at pH 7.0, 25°C, 50 mM Tris-HCl Helicobacter pylori

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000028
-
at pH 7.0 and 25°C Mycobacterium tuberculosis (1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000035
-
at pH 7.0 and 25°C Mycobacterium tuberculosis (1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid
0.000042
-
at pH 7.0 and 25°C Mycobacterium tuberculosis (1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid