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Literature summary for 1.1.1.25 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
Search for more literature for 1.1.1.25

Cloned(Commentary)

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

Inhibitors

Inhibitors Comment Organism Structure
(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
(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
(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
(3R,4S,5R)-3,4,5-trihydroxy-N-(3-hydroxypropyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
(3R,4S,5R)-3,4,5-trihydroxy-N-(4-hydroxybutyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
(3R,4S,5R)-3,4,5-trihydroxy-N-(5-hydroxypentyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
(3R,4S,5R)-3,4,5-trihydroxy-N-(6-hydroxyhexyl)cyclohex-1-ene-1-carboxamide
-
 Escherichia coli
(3R,4S,5R)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]cyclohex-1-enecarboxylic acid
-
 Escherichia coli
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]

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Escherichia coli P15770
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
AroE
-
 Escherichia coli
EcSDH
-
 Escherichia coli
SDH
-
 Escherichia coli

Temperature Optimum [°C]

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

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
NADP+
-
 Escherichia coli
NADPH
-
 Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
 additional information inhibition kinetics, determination of MIC values Escherichia coli
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
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
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
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
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
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
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

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
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)
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)
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)
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
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
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
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