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Literature summary for 2.7.1.71 extracted from

  • Prado, V.; Lence, E.; Thompson, P.; Hawkins, A.R.; Gonzalez-Bello, C.
    Freezing the dynamic gap for selectivity motion-based design of inhibitors of the shikimate kinase enzyme (2016), Chemistry, 22, 17988-18000 .
    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-(naphthalen-2-ylmethoxy)cyclohex-1-ene-1-carboxylic acid
-
 Helicobacter pylori
(3R,4R,5R)-3,4-dihydroxy-5-(naphthalen-2-ylmethoxy)cyclohex-1-ene-1-carboxylic acid
-
 Mycobacterium tuberculosis
(3R,4R,5R)-3,4-dihydroxy-5-[(3-nitrobenzyl)oxy]cyclohex-1-ene-1-carboxylic acid reversible competitive inhibitor Helicobacter pylori
(3R,4R,5R)-3,4-dihydroxy-5-[(3-nitrobenzyl)oxy]cyclohex-1-ene-1-carboxylic acid reversible competitive inhibitor Mycobacterium tuberculosis
(3R,4R,5R)-5-(1-benzothiophen-5-ylmethoxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid reversible competitive inhibitor Helicobacter pylori
(3R,4R,5R)-5-(1-benzothiophen-5-ylmethoxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid reversible competitive inhibitor Mycobacterium tuberculosis
(3R,4S,5R)-5-bis(3-bromo-1H-indol-5-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylic acid
-
 Helicobacter pylori
(3R,4S,5R)-5-bis(3-bromo-1H-indol-5-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylic acid
-
 Mycobacterium tuberculosis
sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(1H-indol-5-yl)methyl]amino]cyclohex-1-ene-1-carboxylate
-
 Helicobacter pylori
sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(1H-indol-5-yl)methyl]amino]cyclohex-1-ene-1-carboxylate
-
 Mycobacterium tuberculosis
sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(naphthalen-2-yl)methyl]amino]cyclohex-1-ene-1-carboxylate
-
 Helicobacter pylori
sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(naphthalen-2-yl)methyl]amino]cyclohex-1-ene-1-carboxylate
-
 Mycobacterium tuberculosis
sodium (3R,4S,5R)-5-di(naphth-2-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylate
-
 Helicobacter pylori
sodium (3R,4S,5R)-5-di(naphth-2-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylate
-
 Mycobacterium tuberculosis
sodium (3R,4S,5R)-5-[bis[(1-benzothiophen-5-yl)methyl]amino]-3,4-dihydroxycyclohex-1-ene-1-carboxylate
-
 Helicobacter pylori
sodium (3R,4S,5R)-5-[bis[(1-benzothiophen-5-yl)methyl]amino]-3,4-dihydroxycyclohex-1-ene-1-carboxylate
-
 Mycobacterium tuberculosis

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.039
-
 shikimate at pH 7.7 and 25°C Helicobacter pylori
0.544
-
 shikimate at pH 7.7 and 25°C Mycobacterium tuberculosis

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ 5 mM used in assay conditions Mycobacterium tuberculosis
Mg2+ 5 mM used in assay conditions Helicobacter pylori

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
-
 ?

Organism

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

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
-
 ?

Synonyms

Synonyms Comment Organism
AroK
-
 Mycobacterium tuberculosis
AroK
-
 Helicobacter pylori

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.116
-
 shikimate at pH 7.7 and 25°C Helicobacter pylori
295
-
 shikimate at pH 7.7 and 25°C Mycobacterium tuberculosis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0003
-
 sodium (3R,4S,5R)-5-di(naphth-2-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylate at pH 7.7 and 25°C Helicobacter pylori
0.00056
-
 (3R,4R,5R)-5-(1-benzothiophen-5-ylmethoxy)-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-(naphthalen-2-ylmethoxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.0052
-
 sodium (3R,4S,5R)-5-[bis[(1-benzothiophen-5-yl)methyl]amino]-3,4-dihydroxycyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Helicobacter pylori
0.0082
-
 (3R,4S,5R)-5-bis(3-bromo-1H-indol-5-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.0087
-
 (3R,4S,5R)-5-bis(3-bromo-1H-indol-5-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
0.022
-
 (3R,4R,5R)-3,4-dihydroxy-5-(naphthalen-2-ylmethoxy)cyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.024
-
 sodium (3R,4S,5R)-5-[bis[(1-benzothiophen-5-yl)methyl]amino]-3,4-dihydroxycyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Mycobacterium tuberculosis
0.043
-
 (3R,4R,5R)-5-(1-benzothiophen-5-ylmethoxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
0.048
-
 sodium (3R,4S,5R)-5-di(naphth-2-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylate at pH 7.7 and 25°C Mycobacterium tuberculosis
0.181
-
 sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(naphthalen-2-yl)methyl]amino]cyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Helicobacter pylori
0.455
-
 sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(1H-indol-5-yl)methyl]amino]cyclohex-1-ene-1-carboxylate at pH 7.7 and 25°C Helicobacter pylori
2
-
 sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(1H-indol-5-yl)methyl]amino]cyclohex-1-ene-1-carboxylate IC50 above 2.0 mM, at pH 7.7 and 25°C Mycobacterium tuberculosis
2
-
 sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(naphthalen-2-yl)methyl]amino]cyclohex-1-ene-1-carboxylate IC50 above 2.0 mM, at pH 7.7 and 25°C Mycobacterium tuberculosis