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Literature summary for 2.7.1.71 extracted from

  • Prado, V.; Lence, E.; Maneiro, M.; Vazquez-Ucha, J.C.; Beceiro, A.; Thompson, P.; Hawkins, A.R.; Gonzalez-Bello, C.
    Targeting the motion of shikimate kinase: development of competitive inhibitors that stabilize an inactive open conformation of the enzyme (2016), J. Med. Chem., 59, 5471-5487.
    View publication on PubMed
Search for more literature for 2.7.1.71

Inhibitors

Inhibitors Comment Organism Structure
(3R,4R,5R)-3,4-dihydroxy-5-(3-methoxybenzyloxy)cyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-3,4-dihydroxy-5-(3-methoxybenzyloxy)cyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-3,4-dihydroxy-5-(3-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-3,4-dihydroxy-5-(3-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-3,4-dihydroxy-5-(4-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-3,4-dihydroxy-5-(4-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-3,4-dihydroxy-5-(naphthyl-2-yl)methoxycyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-3,4-dihydroxy-5-(naphthyl-2-yl)methoxycyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-5-(3-fluorobenzyloxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-5-(3-fluorobenzyloxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-5-(benzo[b]thiophen-5-yl)methoxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-5-(benzo[b]thiophen-5-yl)methoxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-5-benzyloxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-5-benzyloxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4S,5R)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4S,5R)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4S,5R)-5-(4-phenoxymethyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4S,5R)-5-(4-phenoxymethyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3S)-3-aminoshikimic acid competitive reversible inhibitor Helicobacter pylori
(3S)-3-aminoshikimic acid competitive reversible inhibitor Mycobacterium tuberculosis
sodium (3R,4R,5R)-3,4-dihydroxy-5-((perfluorophenyl)methoxy)-cyclohex-1-ene-1-carboxylate
-
 Helicobacter pylori
sodium (3R,4R,5R)-3,4-dihydroxy-5-((perfluorophenyl)methoxy)-cyclohex-1-ene-1-carboxylate
-
 Mycobacterium tuberculosis
sodium (3R,4R,5R)-3,4-dihydroxy-5-(3-nitrobenzyloxy)cyclohex-1-ene-1-carboxylate
-
 Helicobacter pylori
sodium (3R,4R,5R)-3,4-dihydroxy-5-(3-nitrobenzyloxy)cyclohex-1-ene-1-carboxylate
-
 Mycobacterium tuberculosis
sodium (3S,4R,5R)-3-amino-5-(benzo[b]thiophen-5-yl)-methoxy-4-hydroxycyclohex-1-ene-carboxylate
-
 Helicobacter pylori
sodium (3S,4R,5R)-3-amino-5-(benzo[b]thiophen-5-yl)-methoxy-4-hydroxycyclohex-1-ene-carboxylate
-
 Mycobacterium tuberculosis
sodium (3S,4S,5R)-3-amino-4-hydroxy-5-(naphth-2-yl)-metoxycyclohex-1-ene-carboxylate
-
 Helicobacter pylori
sodium (3S,4S,5R)-3-amino-4-hydroxy-5-(naphth-2-yl)-metoxycyclohex-1-ene-carboxylate
-
 Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + shikimate Mycobacterium tuberculosis
-
 ADP + 3-phosphoshikimate
-
 ?
ATP + shikimate Helicobacter pylori
-
 ADP + 3-phosphoshikimate
-
 ?
ATP + shikimate Mycobacterium tuberculosis H37Rv
-
 ADP + 3-phosphoshikimate
-
 ?

Organism

Organism UniProt Comment Textmining
Helicobacter pylori P56073
-
-
Mycobacterium tuberculosis P9WPY3
-
-
Mycobacterium tuberculosis H37Rv P9WPY3
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + shikimate
-
 Mycobacterium tuberculosis ADP + 3-phosphoshikimate
-
 ?
ATP + shikimate
-
 Helicobacter pylori ADP + 3-phosphoshikimate
-
 ?
ATP + shikimate
-
 Mycobacterium tuberculosis H37Rv ADP + 3-phosphoshikimate
-
 ?

Synonyms

Synonyms Comment Organism
AroK
-
 Helicobacter pylori

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.00046
-
 sodium (3R,4R,5R)-3,4-dihydroxy-5-(3-nitrobenzyloxy)cyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Helicobacter pylori
0.00056
-
 (3R,4R,5R)-5-(benzo[b]thiophen-5-yl)methoxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.001
-
 (3R,4R,5R)-3,4-dihydroxy-5-(3-methoxybenzyloxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.00128
-
 (3R,4R,5R)-5-(3-fluorobenzyloxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.0018
-
 (3R,4R,5R)-3,4-dihydroxy-5-(naphthyl-2-yl)methoxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.0021
-
 (3R,4R,5R)-3,4-dihydroxy-5-(3-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.003
-
 (3R,4R,5R)-5-benzyloxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.01
-
 sodium (3R,4R,5R)-3,4-dihydroxy-5-(3-nitrobenzyloxy)cyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Mycobacterium tuberculosis
0.0109
-
 (3R,4R,5R)-3,4-dihydroxy-5-(4-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.022
-
 (3R,4R,5R)-3,4-dihydroxy-5-(naphthyl-2-yl)methoxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.036
-
 (3R,4R,5R)-5-benzyloxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.041
-
 sodium (3R,4R,5R)-3,4-dihydroxy-5-((perfluorophenyl)methoxy)-cyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Helicobacter pylori
0.043
-
 (3R,4R,5R)-5-(benzo[b]thiophen-5-yl)methoxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.067
-
 (3R,4S,5R)-5-(4-phenoxymethyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.095
-
 (3R,4S,5R)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.109
-
 (3R,4R,5R)-3,4-dihydroxy-5-(3-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.135
-
 (3R,4R,5R)-3,4-dihydroxy-5-(3-methoxybenzyloxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.166
-
 (3R,4R,5R)-3,4-dihydroxy-5-(4-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.18
-
 (3R,4R,5R)-5-(3-fluorobenzyloxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.415
-
 sodium (3S,4R,5R)-3-amino-5-(benzo[b]thiophen-5-yl)-methoxy-4-hydroxycyclohex-1-ene-carboxylate at pH 7.7 and 25°C Mycobacterium tuberculosis
0.535
-
 sodium (3S,4R,5R)-3-amino-5-(benzo[b]thiophen-5-yl)-methoxy-4-hydroxycyclohex-1-ene-carboxylate at pH 7.7 and 25°C Helicobacter pylori
0.71
-
 sodium (3R,4R,5R)-3,4-dihydroxy-5-((perfluorophenyl)methoxy)-cyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Mycobacterium tuberculosis
0.8
-
 sodium (3S,4S,5R)-3-amino-4-hydroxy-5-(naphth-2-yl)-metoxycyclohex-1-ene-carboxylate Ki above 0.8 mM, at pH 7.7 and 25°C Helicobacter pylori
2
-
 (3R,4S,5R)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid Ki above 2.0 mM, at pH 7.7 and 25°C Mycobacterium tuberculosis
2
-
 (3R,4S,5R)-5-(4-phenoxymethyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid Ki above 2.0 mM, at pH 7.7 and 25°C Mycobacterium tuberculosis
2
-
 sodium (3S,4S,5R)-3-amino-4-hydroxy-5-(naphth-2-yl)-metoxycyclohex-1-ene-carboxylate Ki above 2.0 mM, at pH 7.7 and 25°C Mycobacterium tuberculosis