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Literature summary extracted from
- Mycobacterium tuberculosis chorismate mutase a potential target for TB (2017), Bioorg. Med. Chem., 25, 1725-1736 .
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | drug development | the secretory isozyme is a target for the discovery of anti-tubercular agents | Mycobacterium tuberculosis |
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 5.4.99.5 | the Rv1885c gene product is synthesized with an N-terminal signal sequence of 33 amino acids, which is cleaved off upon heterologous expression in Escherichia coli, and transported into the periplasmic space | Mycobacterium tuberculosis |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 5.4.99.5 | (1R,3R,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid | - |
Mycobacterium tuberculosis |  |
| 5.4.99.5 | (1R,3R,5S,8R)-8-hydroxy-5-nitro-2-azabicyclo[3.3.1]non-6-ene-3-carboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1R,3R,5S,8R)-8-hydroxy-5-nitro-2-oxabicyclo[3.3.1]non-6-ene-3-carboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1R,3S,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1R,3S,5S,8R)-8-hydroxy-5-nitro-2-oxabicyclo[3.3.1]non-6-ene-3-carboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1R,3S,6S,8S,10S)-10-hydroxy-4-oxo-5-oxa-2-azatricyclo[4.3.1.13,8]undecane-8-carboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1R,5R,8R)-8-hydroxy-2-oxabicyclo[3.3.1]nona-3,6-diene-3,5-dicarboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1R,5S,8R)-8-hydroxy-2-azabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (1S,2aR,2bR,3S)-4-oxohexahydro-1H-5-oxa-2b-aza-1,3-methanocyclopropa[cd]indene-1-carboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | (2Z)-2-(4-chlorophenyl)-3-[4-(dimethoxymethyl)-2-nitrophenyl]prop-2-enoic acid | competitive | Mycobacterium tuberculosis | |
| 5.4.99.5 | (Z)-3-(4-nitrobenzylidene)indolin-2-one | MIC is 0.0235 mM | Mycobacterium tuberculosis | |
| 5.4.99.5 | 1-(2-(tert-butyl)-5-chloro-7-(methylsulfonyl)-1H-indol-3-yl)ethan-1-one | 45% inhibition at 0.03 mM | Mycobacterium tuberculosis | |
| 5.4.99.5 | 1-aminoadamantane | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 1-hydroxyadamantane | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 2-chloro-3-(5,6-difluoro-1H-indol-3-yl)quinoxaline | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 2-chloro-4-(ethoxycarbonyl)-1-hydroxy-6-methylquinolin-1-ium | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 2-[2-[3-(tert-butoxycarbonyl)-2-phenyl-1,3-thiazolidin-4-yl]ethyl]-4-methylpentanoic acid | competitive | Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-((dihydroxyamino)thio)-4-((3,5-dimethoxyphenethyl)amino)-5-nitrobenzoic acid | competitive | Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-(3-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[b]thieno[2,3d]pyrimidin-4[3H]-one | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-amino-1-(3-(4-hydroxybut-1-yn-1-yl)phenyl)-1H-benzol[f]chromene-2-carbonitril | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-chloroadamantane | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 5-naphthyl-7-propyl-3H-pyrazolo-[4,3-d][1,2,3]triazin-4[5h]-one | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 6'-iodo-1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one | a spiro 2,3-dihydroquinazolin-4(1H)-one | Mycobacterium tuberculosis | |
| 5.4.99.5 | 6,6'-dinitro-[1,1'-biphenyl]-2,2'-dicarboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 6-hydroxyadamantane | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 6-hydroxybicyclo[3.3.1]nonane-1,3-dicarboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | adamantan phosphonic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | Adamantane-1-acetic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | adamantane-1-carboxylic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | carvacrol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | ethyl 4-(2-(4-hydroxybut-1-yn-1-yl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | indoline-2,3-dione | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | methyl 4-(methylamino)-3-nitrobenzoate | competitive | Mycobacterium tuberculosis | |
| 5.4.99.5 | additional information | development and synthesis of transition state analogues and small molecule compounds as enzyme inhibitors | Mycobacterium tuberculosis | |
| 5.4.99.5 | N-(4-fluoro-2-(5-fluoro-1-(methylsulfonyl)-1H-inden-2-yl)phenyl)methanesulfonamide | - |
Mycobacterium tuberculosis | |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | additional information | - |
additional information | Michaelis-Menten kinetics | Mycobacterium tuberculosis | |
| 5.4.99.5 | 0.5 | - |
chorismate | pH 7.0, 37°C | Mycobacterium tuberculosis | |
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 5.4.99.5 | extracellular | the isozyme MtbCM is secreted | Mycobacterium tuberculosis | - |
- |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.4.99.5 | Chorismate | Mycobacterium tuberculosis | - |
Prephenate | - |
ir | |
| 5.4.99.5 | Chorismate | Mycobacterium tuberculosis ATCC 25618 / H37Rv | - |
Prephenate | - |
ir | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 5.4.99.5 | Mycobacterium tuberculosis | P9WIB9 | secretory isoform | - |
| 5.4.99.5 | Mycobacterium tuberculosis ATCC 25618 / H37Rv | P9WIB9 | secretory isoform | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.4.99.5 | Chorismate | - |
Mycobacterium tuberculosis | Prephenate | - |
ir | |
| 5.4.99.5 | Chorismate | the rearrangement of chorismate to prephenate is strongly exergonic and essentially irreversible in nature | Mycobacterium tuberculosis | Prephenate | - |
ir | |
| 5.4.99.5 | Chorismate | - |
Mycobacterium tuberculosis ATCC 25618 / H37Rv | Prephenate | - |
ir | |
| 5.4.99.5 | Chorismate | the rearrangement of chorismate to prephenate is strongly exergonic and essentially irreversible in nature | Mycobacterium tuberculosis ATCC 25618 / H37Rv | Prephenate | - |
ir | |
| 5.4.99.5 | additional information | the isozyme encoded by Rv1885c is characterized as a mono-functional chorismate mutase | Mycobacterium tuberculosis | ? | - |
? | |
| 5.4.99.5 | additional information | the isozyme encoded by Rv1885c is characterized as a mono-functional chorismate mutase | Mycobacterium tuberculosis ATCC 25618 / H37Rv | ? | - |
? | |
Subunits
| EC Number | Subunits | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | homodimer | 2 * 36000 | Mycobacterium tuberculosis |
| 5.4.99.5 | More | secretory isozyme MtbCM undergoes dimerization mediated through residues (90-119) spanning H3 in both subunits, with the two helices placed anti parallel to each other. The polypeptide consists of eight a-helices H-H8 connected by turns and loop segments | Mycobacterium tuberculosis |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | MtbCM | - |
Mycobacterium tuberculosis |
| 5.4.99.5 | Rv1885c | - |
Mycobacterium tuberculosis |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 5.4.99.5 | 37 | - |
assay at | Mycobacterium tuberculosis |
Temperature Stability [°C]
| EC Number | Temperature Stability Minimum [°C] | Temperature Stability Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 5.4.99.5 | 60 | - |
isozyme MtCM meltig temperature is 48°C, complete inactivation at 60°C | Mycobacterium tuberculosis |
Turnover Number [1/s]
| EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | 60 | - |
chorismate | pH 7.0, 37°C | Mycobacterium tuberculosis | |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 5.4.99.5 | 7 | - |
assay at | Mycobacterium tuberculosis |
Ki Value [mM]
| EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | 0.0057 | - |
3-((dihydroxyamino)thio)-4-((3,5-dimethoxyphenethyl)amino)-5-nitrobenzoic acid | pH 7.0, 37°C | Mycobacterium tuberculosis | |
| 5.4.99.5 | 0.0177 | - |
2-[2-[3-(tert-butoxycarbonyl)-2-phenyl-1,3-thiazolidin-4-yl]ethyl]-4-methylpentanoic acid | pH 7.0, 37°C | Mycobacterium tuberculosis | |
| 5.4.99.5 | 0.0211 | - |
(2Z)-2-(4-chlorophenyl)-3-[4-(dimethoxymethyl)-2-nitrophenyl]prop-2-enoic acid | pH 7.0, 37°C | Mycobacterium tuberculosis | |
| 5.4.99.5 | 0.0288 | - |
methyl 4-(methylamino)-3-nitrobenzoate | pH 7.0, 37°C | Mycobacterium tuberculosis | |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | 0.00101 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | indoline-2,3-dione | |
| 5.4.99.5 | 0.0148 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | ethyl 4-(2-(4-hydroxybut-1-yn-1-yl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | |
| 5.4.99.5 | 0.01513 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | 5-naphthyl-7-propyl-3H-pyrazolo-[4,3-d][1,2,3]triazin-4[5h]-one | |
| 5.4.99.5 | 0.01563 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | 3-amino-1-(3-(4-hydroxybut-1-yn-1-yl)phenyl)-1H-benzol[f]chromene-2-carbonitril | |
| 5.4.99.5 | 0.0197 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | 2-chloro-3-(5,6-difluoro-1H-indol-3-yl)quinoxaline | |
| 5.4.99.5 | 0.0198 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | 3-(3-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[b]thieno[2,3d]pyrimidin-4[3H]-one | |
| 5.4.99.5 | 0.0239 | - |
pH 7.0, 37°C | Mycobacterium tuberculosis | 2-chloro-4-(ethoxycarbonyl)-1-hydroxy-6-methylquinolin-1-ium | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | evolution | isozyme MtbCM belongs to the ?AroQ/AroQc family. The family members exhibit sequence similarity only in the N-terminal moiety, and lack a catalytically crucial and conserved arginine residue in helix H1. The proteins contain a catalytic site which is formed within a single protomer and lacks regulatory domain | Mycobacterium tuberculosis |
| 5.4.99.5 | malfunction | the inhibition of secretory isozyme MtbCM may hinder the supply of nutrients to the organism | Mycobacterium tuberculosis |
| 5.4.99.5 | metabolism | Mycobacterium tuberculosis chorismate mutase (MtbCM) catalyzes the rearrangement of chorismate to prephenate in the shikimate biosynthetic pathway which forms the essential amino acids, phenylalanine and tyrosine | Mycobacterium tuberculosis |
| 5.4.99.5 | physiological function | Mycobacterium tuberculosis chorismate mutase (MtbCM) catalyzes the rearrangement of chorismate to prephenate in the shikimate biosynthetic pathway which forms the essential amino acids, phenylalanine and tyrosine. The secretory isozyme MtbCM (encoded by gene Rv1885c) is assumed to play a key role in pathogenesis of tuberculosis. Isozyme MtbCM is independent of regulation | Mycobacterium tuberculosis |
kcat/KM [mM/s]
| EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | 120 | - |
chorismate | pH 7.0, 37°C | Mycobacterium tuberculosis | |
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