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Literature summary extracted from

  • Diaz-Quiroz, D.C.; Cardona-Felix, C.S.; Viveros-Ceballos, J.L.; Reyes-Gonzalez, M.A.; Bolivar, F.; Ordonez, M.; Escalante, A.
    Synthesis, biological activity and molecular modelling studies of shikimic acid derivatives as inhibitors of the shikimate dehydrogenase enzyme of Escherichia coli (2018), J. Enzyme Inhib. Med. Chem., 33, 397-404 .
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.25 gene aroE, recombinant expression in Escherichia coli strain JM101 Escherichia coli

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.25 (3R,3'R,4S,4'S,5R,5'R)-N,N'-(butane-1,4-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
-
 Escherichia coli
1.1.1.25 (3R,3'R,4S,4'S,5R,5'R)-N,N'-(ethane-1,2-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
-
 Escherichia coli
1.1.1.25 (3R,3'R,4S,4'S,5R,5'R)-N,N'-(propane-1,3-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
-
 Escherichia coli
1.1.1.25 (3R,4S,5R)-3,4,5-trihydroxy-N-(3-hydroxypropyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
1.1.1.25 (3R,4S,5R)-3,4,5-trihydroxy-N-(4-hydroxybutyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
1.1.1.25 (3R,4S,5R)-3,4,5-trihydroxy-N-(5-hydroxypentyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
1.1.1.25 (3R,4S,5R)-3,4,5-trihydroxy-N-(6-hydroxyhexyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
1.1.1.25 (3R,4S,5R)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarboxylic acid
-
 Escherichia coli
1.1.1.25 additional information synthesis, biological activity and molecular modelling studies of shikimic acid derivatives as inhibitors of the shikimate dehydrogenase enzyme of Escherichia coli, evaluation for in vitro SDH inhibition and antibacterial activity against Escherichia coli, molecular docking studies, overview. All tested compounds are mixed-type inhibitors, diamide derivatives display more inhibitory activity than synthesised monoamides Escherichia coli

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.25 additional information
-
 additional information Michaelis-Menten kinetics Escherichia coli

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.25 shikimate + NADP+ Escherichia coli
-
 3-dehydroshikimate + NADPH + H+
-
 r

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.25 Escherichia coli P15770
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.25 shikimate + NADP+
-
 Escherichia coli 3-dehydroshikimate + NADPH + H+
-
 r

Synonyms

EC Number Synonyms Comment Organism
1.1.1.25 AroE
-
 Escherichia coli
1.1.1.25 EcSDH
-
 Escherichia coli
1.1.1.25 SDH
-
 Escherichia coli

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.25 25
-
 assay at, oxidation of NADPH Escherichia coli

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.25 7.5
-
 assay at, oxidation of NADPH Escherichia coli

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.25 NADP+
-
 Escherichia coli
1.1.1.25 NADPH
-
 Escherichia coli

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.1.1.25 additional information
-
 additional information inhibition kinetics, determination of MIC values Escherichia coli
1.1.1.25 0.4
-
 (3R,3'R,4S,4'S,5R,5'R)-N,N'-(propane-1,3-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide) potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli
1.1.1.25 0.416
-
 (3R,3'R,4S,4'S,5R,5'R)-N,N'-(ethane-1,2-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide) 25°potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli
1.1.1.25 0.458
-
 (3R,3'R,4S,4'S,5R,5'R)-N,N'-(butane-1,4-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide) potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli
1.1.1.25 0.587
-
 (3R,4S,5R)-3,4,5-trihydroxy-N-(6-hydroxyhexyl)cyclohex-1-ene-1-carboxamide potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli
1.1.1.25 0.642
-
 (3R,4S,5R)-3,4,5-trihydroxy-N-(5-hydroxypentyl)cyclohex-1-ene-1-carboxamide potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli
1.1.1.25 0.717
-
 (3R,4S,5R)-3,4,5-trihydroxy-N-(4-hydroxybutyl)cyclohex-1-ene-1-carboxamide potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli
1.1.1.25 0.733
-
 (3R,4S,5R)-3,4,5-trihydroxy-N-(3-hydroxypropyl)cyclohex-1-ene-1-carboxamide potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.25 0.588
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,3'R,4S,4'S,5R,5'R)-N,N'-(ethane-1,2-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
1.1.1.25 0.589
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,3'R,4S,4'S,5R,5'R)-N,N'-(propane-1,3-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
1.1.1.25 0.652
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,3'R,4S,4'S,5R,5'R)-N,N'-(butane-1,4-diyl)bis(3,4,5-trihydroxycyclohex-1-ene-1-carboxamide)
1.1.1.25 0.829
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,4S,5R)-3,4,5-trihydroxy-N-(6-hydroxyhexyl)cyclohex-1-ene-1-carboxamide
1.1.1.25 0.882
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,4S,5R)-3,4,5-trihydroxy-N-(4-hydroxybutyl)cyclohex-1-ene-1-carboxamide
1.1.1.25 0.949
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,4S,5R)-3,4,5-trihydroxy-N-(3-hydroxypropyl)cyclohex-1-ene-1-carboxamide
1.1.1.25 0.953
-
 potassium phosphate buffer, pH 7.5, 25°C, cofactor NADPH Escherichia coli (3R,4S,5R)-3,4,5-trihydroxy-N-(5-hydroxypentyl)cyclohex-1-ene-1-carboxamide