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Literature summary for 5.4.99.5 extracted from

  • Agrawal, H.; Kumar, A.; Bal, N.C.; Siddiqi, M.I.; Arora, A.
    Ligand based virtual screening and biological evaluation of inhibitors of chorismate mutase (Rv1885c) from Mycobacterium tuberculosis H37Rv (2007), Bioorg. Med. Chem. Lett., 17, 3053-3058.
    View publication on PubMed
Search for more literature for 5.4.99.5

Application

Application Comment Organism
drug development multiple-drug-resistant tuberculoses bacillus and its synergism with HIV-characterization of new enzyme targets and the development of new drugs Mycobacterium tuberculosis

Crystallization (Commentary)

Crystallization (Comment) Organism
MtCM (Rv1885c) (PDB ID-2F6L), docked conformation of (3S,6Z)-8-hydroxy-2-oxabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid, 4-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-nitro-5-sulfamoylbenzoic acid, and (3S,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid, (2Z)-2-(4-chlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-enoic acid in the catalytic site of MtCM x-ray crystal structure is shown Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
(2Z)-2-(4-chlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-enoic acid
-
 Mycobacterium tuberculosis
(3R,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid
-
 Mycobacterium tuberculosis
(3S,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid
-
 Mycobacterium tuberculosis
(3S,6Z)-8-hydroxy-2-oxabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid
-
 Mycobacterium tuberculosis
4-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-nitro-5-sulfamoylbenzoic acid
-
 Mycobacterium tuberculosis
methyl 4-(methylamino)-3-nitrobenzoate
-
 Mycobacterium tuberculosis
additional information aza inhibitors. Competitive inhibition, Saccharomyces cerevisiae chorismate mutase inhibitors and the substrate chorismic acid used for pharmacophore model generation. These inhibitors do not alter Vmax at the higher concentration of substrate (1-5 mM) Mycobacterium tuberculosis
N-[[3-(tert-butoxycarbonyl)-2-phenyl-1,3-thiazolidin-4-yl]carbonyl]leucine
-
 Mycobacterium tuberculosis

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 Chorismic acid Competetive inhibition by I – IV Structur: increase the Km Mycobacterium tuberculosis

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular MtCM is secreted out of the cell to provide support to Mycobacterium tuberculosis in aromatic amino acid deficient medium Mycobacterium tuberculosis
-
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
Chorismate Mycobacterium tuberculosis
-
 Prephenate
-
 ?
Chorismate Mycobacterium tuberculosis H37Rv
-
 Prephenate
-
 ?

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WIB9
-
-
Mycobacterium tuberculosis H37Rv P9WIB9
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Chorismate
-
 Mycobacterium tuberculosis Prephenate
-
 ?
Chorismate
-
 Mycobacterium tuberculosis H37Rv Prephenate
-
 ?

Synonyms

Synonyms Comment Organism
chorismate mutase
-
 Mycobacterium tuberculosis
MtCM
-
 Mycobacterium tuberculosis
Mycobacterium tuberculosis H37Rv chorismate mutase
-
 Mycobacterium tuberculosis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
 assay at Mycobacterium tuberculosis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0057
-
 4-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-nitro-5-sulfamoylbenzoic acid 4-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-nitro-5-sulfamoylbenzoic acid shows the most potent inhibition with Ki value of 0.0057 mM against MtCM Mycobacterium tuberculosis
0.01771
-
 (2Z)-2-(4-chlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-enoic acid
-
 Mycobacterium tuberculosis
0.0211
-
 N-[[3-(tert-butoxycarbonyl)-2-phenyl-1,3-thiazolidin-4-yl]carbonyl]leucine
-
 Mycobacterium tuberculosis
0.0288
-
 methyl 4-(methylamino)-3-nitrobenzoate
-
 Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.007
-
 (3S,6Z)-8-hydroxy-2-oxabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid Mycobacterium tuberculosis Saccharomyces cerevisiae chorismate mutase inhibitors
1.2
-
 (3S,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid Mycobacterium tuberculosis Saccharomyces cerevisiae chorismate mutase inhibitors
18
-
 (3R,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid Mycobacterium tuberculosis Saccharomyces cerevisiae chorismate mutase inhibitors