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Literature summary extracted from

  • Pernas, M.; Blanco, B.; Lence, E.; Thompson, P.; Hawkins, A.; González-Bello, C.
    Synthesis of rigidified shikimic acid derivatives by ring-closing metathesis to imprint inhibitor efficacy against shikimate kinase enzyme (2019), Org. Chem. Front., 6, 2514-2528 .
No PubMed abstract available

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.7.1.71 (1R,4R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,4R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,4S,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,4S,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-4-benzyloxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-4-benzyloxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-4-butyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-4-butyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-4-cyclopropylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-4-cyclopropylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-4-ethoxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-4-ethoxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-4-ethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-4-ethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-4-hydroxylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-4-hydroxylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4,7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4,7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-4-propyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Helicobacter pylori
2.7.1.71 (1R,6S,10S)-6,10-dihydroxy-4-propyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
-
Mycobacterium tuberculosis

Metals/Ions

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

Natural Substrates/ Products (Substrates)

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

Organism

EC Number Organism UniProt Comment Textmining
2.7.1.71 Helicobacter pylori
-
-
-
2.7.1.71 Mycobacterium tuberculosis P9WPY3
-
-
2.7.1.71 Mycobacterium tuberculosis H37Rv P9WPY3
-
-

Substrates and Products (Substrate)

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

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.7.1.71 0.005
-
(1R,6S,10S)-4-ethoxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.0092
-
(1R,6S,10S)-6,10-dihydroxy-4-propyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.01
-
(1R,6S,10S)-4-cyclopropylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.012
-
(1R,6S,10S)-4-butyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.0155
-
(1R,6S,10S)-4-ethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.028
-
(1R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.038
-
(1R,6S,10S)-4-hydroxylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.041
-
(1R,6S,10S)-4-ethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.046
-
(1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.047
-
(1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.0545
-
(1R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.062
-
(1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4,7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.068
-
(1R,6S,10S)-4-benzyloxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.072
-
(1R,6S,10S)-6,10-dihydroxy-4-propyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.101
-
(1R,6S,10S)-4-cyclopropylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.104
-
(1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4,7-diene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.121
-
(1R,6S,10S)-4-benzyloxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.17
-
(1R,6S,10S)-4-ethoxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.177
-
(1R,6S,10S)-4-butyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.333
-
(1R,6S,10S)-4-hydroxylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.36
-
(1R,4S,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis
2.7.1.71 0.465
-
(1R,4S,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid at pH 7.7 and 25°C Helicobacter pylori
2.7.1.71 0.645
-
(1R,4R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid at pH 7.7 and 25°C Mycobacterium tuberculosis