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Literature summary for 4.2.99.21 extracted from
- Investigation of potential inhibitors of chorismate-utilizing enzymes (2015), Curr. Med. Chem., 22, 1383-1399 .
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| sequence comparisons | Pseudomonas aeruginosa |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| (4R,5R)-5-(carboxymethoxy)-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Yersinia enterocolitica |  |
| (4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Mycobacterium tuberculosis | |
| (4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | inhibition of salicylate synthase activity | Pseudomonas aeruginosa | |
| (4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Yersinia enterocolitica | |
| (4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Yersinia pestis | |
| (4R,5R)-5-[(1R)-1-carboxyethoxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Yersinia enterocolitica | |
| (4R,5R)-5-[(1S)-1-carboxyethoxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Yersinia enterocolitica | |
| (4R,5R)-5-[(2-carboxyprop-2-en-1-yl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | - |
Yersinia enterocolitica | |
| 1-(2-sulfanylidene-2,3-dihydro-1H-benzimidazol-1-yl)ethan-1-one | - |
Mycobacterium tuberculosis | |
| 2-amino-3-(1-carboxyethoxy)benzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-2-hydroxybenzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-2-nitrobenzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-4,5-dihydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-(1-carboxyethoxy)-4-(hydroxymethyl)benzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-4-(sulfanylmethyl)benzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-4-hydroxybenzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-4-methoxybenzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)-4-methylbenzoic acid | - |
Yersinia enterocolitica | |
| 3-(1-carboxyethoxy)benzoic acid | - |
Yersinia enterocolitica | |
| 3-(3,4-dichlorobenzene-1-sulfonyl)benzene-1-sulfonamide | - |
Mycobacterium tuberculosis | |
| 3-([(E)-1-carboxy-2-[2-(trifluoromethyl)phenyl]ethenyl]oxy)-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-([(E)-1-carboxy-2-[3-(trifluoromethyl)phenyl]ethenyl]oxy)-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-([(E)-1-carboxy-2-[4-(trifluoromethyl)phenyl]ethenyl]oxy)-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-([(E)-2-[2-(acetyloxy)phenyl]-1-carboxyethenyl]oxy)-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-([(E)-2-[3-(acetyloxy)phenyl]-1-carboxyethenyl]oxy)-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-([(E)-2-[4-(acetyloxy)phenyl]-1-carboxyethenyl]oxy)-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[(1-carboxyethenyl)oxy]-4,5-dihydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[(1-carboxyethenyl)oxy]-4-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[(1-carboxyethenyl)oxy]benzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[(2-carboxyprop-2-en-1-yl)oxy]-4,5-dihydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(1E)-1-carboxy-3-methylbut-1-en-1-yl]oxy]-4-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(1E)-1-carboxy-3-methylbut-1-en-1-yl]oxy]benzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(1E)-1-carboxybut-1-en-1-yl]oxy]benzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(1E)-1-carboxyprop-1-en-1-yl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(1E)-1-carboxyprop-1-en-1-yl]oxy]-4-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(1E)-1-carboxyprop-1-en-1-yl]oxy]benzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-(2-chlorophenyl)ethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-(2-methylphenyl)ethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-(3-chlorophenyl)ethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-(3-methylphenyl)ethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-(4-chlorophenyl)ethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-(4-methylphenyl)ethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-phenylethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-phenylethenyl]oxy]-4-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-1-carboxy-2-phenylethenyl]oxy]benzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-2-(2-bromophenyl)-1-carboxyethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-2-(3-bromophenyl)-1-carboxyethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 3-[[(E)-2-(4-bromophenyl)-1-carboxyethenyl]oxy]-2-hydroxybenzoic acid | - |
Mycobacterium tuberculosis | |
| 4,4'-sulfonylbis(2,6-dinitrophenol) | - |
Pseudomonas aeruginosa | |
| 4,4'-sulfonylbis(2,6-dinitrophenol) | - |
Yersinia enterocolitica | |
| 4,6-dinitro-2-oxo-1,3-benzoxathiol-5-yl methyl carbonate | - |
Pseudomonas aeruginosa | |
| 4,6-dinitro-2-oxo-2H-1,3-benzoxathiol-5-yl methyl carbonate | - |
Yersinia enterocolitica | |
| 4-(azidomethyl)-3-(1-carboxyethoxy)benzoic acid | - |
Yersinia enterocolitica | |
| 4-amino-3-(1-carboxyethoxy)benzoic acid | - |
Yersinia enterocolitica | |
| 5-[(2-carboxyphenyl)sulfamoyl]-2-hydroxybenzoic acid | - |
Pseudomonas aeruginosa | |
| 5-[(2-carboxyphenyl)sulfamoyl]-2-methylbenzoic acid | - |
Yersinia enterocolitica | |
| methyl 2-hydroxy-3-([(1E)-3-methoxy-3-oxo-1-[2-(trifluoromethyl)phenyl]prop-1-en-2-yl]oxy)benzoate | - |
Mycobacterium tuberculosis | |
| methyl 2-hydroxy-3-([(1E)-3-methoxy-3-oxo-1-[3-(trifluoromethyl)phenyl]prop-1-en-2-yl]oxy)benzoate | - |
Mycobacterium tuberculosis | |
| methyl 2-hydroxy-3-([(1E)-3-methoxy-3-oxo-1-[4-(trifluoromethyl)phenyl]prop-1-en-2-yl]oxy)benzoate | - |
Mycobacterium tuberculosis | |
| methyl 2-hydroxy-3-[[(1E)-3-methoxy-1-(2-methylphenyl)-3-oxoprop-1-en-2-yl]oxy]benzoate | - |
Mycobacterium tuberculosis | |
| methyl 2-hydroxy-3-[[(1E)-3-methoxy-1-(3-methylphenyl)-3-oxoprop-1-en-2-yl]oxy]benzoate | - |
Mycobacterium tuberculosis | |
| methyl 2-hydroxy-3-[[(1E)-3-methoxy-1-(4-methylphenyl)-3-oxoprop-1-en-2-yl]oxy]benzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-([(1E)-1-[2-(acetyloxy)phenyl]-3-methoxy-3-oxoprop-1-en-2-yl]oxy)-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-([(1E)-1-[3-(acetyloxy)phenyl]-3-methoxy-3-oxoprop-1-en-2-yl]oxy)-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-([(1E)-1-[4-(acetyloxy)phenyl]-3-methoxy-3-oxoprop-1-en-2-yl]oxy)-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-[[(1E)-1-(2-bromophenyl)-3-methoxy-3-oxoprop-1-en-2-yl]oxy]-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-[[(1E)-1-(2-chlorophenyl)-3-methoxy-3-oxoprop-1-en-2-yl]oxy]-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-[[(1E)-1-(3-bromophenyl)-3-methoxy-3-oxoprop-1-en-2-yl]oxy]-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-[[(1E)-1-(3-chlorophenyl)-3-methoxy-3-oxoprop-1-en-2-yl]oxy]-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-[[(1E)-1-(4-bromophenyl)-3-methoxy-3-oxoprop-1-en-2-yl]oxy]-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| methyl 3-[[(1E)-1-(4-chlorophenyl)-3-methoxy-3-oxoprop-1-en-2-yl]oxy]-2-hydroxybenzoate | - |
Mycobacterium tuberculosis | |
| additional information | inhibitor structure-function realtionship and molecular docking; inhibitor structure-function relationship and molecular docking | Mycobacterium tuberculosis | |
| additional information | inhibitor structure-function realtionship and molecular docking; inhibitor structure-function relationship and molecular docking | Yersinia enterocolitica | |
| additional information | inhibitor structure-function realtionship and molecular docking; inhibitor structure-function relationship and molecular docking | Yersinia pestis | |
| N-ethyl-3-(3-oxo-1,2-benzothiazol-2(3H)-yl)benzene-1-sulfonamide | - |
Mycobacterium tuberculosis | |
| [4-carboxy-2-(1-carboxyethoxy)phenyl]methanaminium | - |
Yersinia enterocolitica | |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| Mg2+ | required | Yersinia pestis | |
| Mg2+ | required | Yersinia enterocolitica | |
| Mg2+ | required | Pseudomonas aeruginosa | |
| Mg2+ | required | Mycobacterium tuberculosis | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| isochorismate | Yersinia pestis | - |
salicylate + pyruvate | - |
? | |
| isochorismate | Yersinia enterocolitica | - |
salicylate + pyruvate | - |
? | |
| isochorismate | Pseudomonas aeruginosa | - |
salicylate + pyruvate | - |
? | |
| isochorismate | Mycobacterium tuberculosis | - |
salicylate + pyruvate | - |
? | |
| isochorismate | Mycobacterium tuberculosis ATCC 25618 | - |
salicylate + pyruvate | - |
? | |
| isochorismate | Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 | - |
salicylate + pyruvate | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Mycobacterium tuberculosis | P9WFX1 | - |
- |
| Mycobacterium tuberculosis ATCC 25618 | P9WFX1 | - |
- |
| no activity in Homo sapiens | - |
- |
- |
| Pseudomonas aeruginosa | Q51507 | - |
- |
| Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 | Q51507 | - |
- |
| Yersinia enterocolitica | - |
- |
- |
| Yersinia pestis | - |
- |
- |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| isochorismate = salicylate + pyruvate | overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate | Yersinia pestis | |
| isochorismate = salicylate + pyruvate | overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate | Yersinia enterocolitica | |
| isochorismate = salicylate + pyruvate | overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate | Mycobacterium tuberculosis |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| isochorismate | - |
Yersinia pestis | salicylate + pyruvate | - |
? | |
| isochorismate | - |
Yersinia enterocolitica | salicylate + pyruvate | - |
? | |
| isochorismate | - |
Pseudomonas aeruginosa | salicylate + pyruvate | - |
? | |
| isochorismate | - |
Mycobacterium tuberculosis | salicylate + pyruvate | - |
? | |
| isochorismate | - |
Mycobacterium tuberculosis ATCC 25618 | salicylate + pyruvate | - |
? | |
| isochorismate | - |
Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1 | salicylate + pyruvate | - |
? | |
| additional information | the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Yersinia pestis | ? | - |
? | |
| additional information | the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Yersinia enterocolitica | ? | - |
? | |
| additional information | the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Mycobacterium tuberculosis | ? | - |
? | |
| additional information | the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Mycobacterium tuberculosis ATCC 25618 | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| IPL | UniProt | Pseudomonas aeruginosa |
| isochorismate-pyruvate lyase | - |
Pseudomonas aeruginosa |
| PchB | - |
Pseudomonas aeruginosa |
| salicylate synthase | EC 5.4.4.2 and 4.2.99.21 | Yersinia pestis |
| salicylate synthase | EC 5.4.4.2 and 4.2.99.21 | Yersinia enterocolitica |
| salicylate synthase | EC 5.4.4.2 and 4.2.99.21 | Mycobacterium tuberculosis |
Ki Value [mM]
| Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.0001 | - |
4,4'-sulfonylbis(2,6-dinitrophenol) | pH and temperature not specified in the publication | Pseudomonas aeruginosa | |
| 0.0001 | - |
5-[(2-carboxyphenyl)sulfamoyl]-2-hydroxybenzoic acid | pH and temperature not specified in the publication | Pseudomonas aeruginosa | |
| 0.00087 | - |
4,6-dinitro-2-oxo-1,3-benzoxathiol-5-yl methyl carbonate | pH and temperature not specified in the publication | Pseudomonas aeruginosa | |
| 0.025 | - |
4,6-dinitro-2-oxo-2H-1,3-benzoxathiol-5-yl methyl carbonate | pH and temperature not specified in the publication | Yersinia enterocolitica | |
| 0.16 | - |
(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | pH and temperature not specified in the publication | Yersinia enterocolitica | |
| 0.16 | - |
(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid | pH and temperature not specified in the publication, inhibition of salicylate synthase activity | Pseudomonas aeruginosa | |
| 1.4 | - |
3-(1-carboxyethoxy)-4,5-dihydroxybenzoic acid | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
| 1.7 | - |
3-[(1-carboxyethenyl)oxy]-4,5-dihydroxybenzoic acid | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
| 3 | - |
3-[(2-carboxyprop-2-en-1-yl)oxy]-4,5-dihydroxybenzoic acid | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
General Information
| General Information | Comment | Organism |
|---|---|---|
| metabolism | the first committed step during the biosynthesis of siderophores, which are small molecules capable of chelating iron from the host organism, is the conversion of chorismate into isochorismate by isochorismate synthase (EC 5.4.4.2) and consequently to salicylate by isochorismate pyruvate-lyase (EC 4.2.99.21). Salicylate synthase converts chorismate into salicylate through a two-step reaction | Pseudomonas aeruginosa |
| metabolism | the first committed step during the biosynthesis of siderophores, which are small molecules capable of chelating iron from the host organism, is the conversion of chorismate into isochorismate by isochorismate synthase (EC 5.4.4.2) and consequently to salicylate by isochorismate pyruvate-lyase (EC 4.2.99.21). the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Yersinia pestis |
| metabolism | the first committed step during the biosynthesis of siderophores, which are small molecules capable of chelating iron from the host organism, is the conversion of chorismate into isochorismate by isochorismate synthase (EC 5.4.4.2) and consequently to salicylate by isochorismate pyruvate-lyase (EC 4.2.99.21). the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Yersinia enterocolitica |
| metabolism | the first committed step during the biosynthesis of siderophores, which are small molecules capable of chelating iron from the host organism, is the conversion of chorismate into isochorismate by isochorismate synthase (EC 5.4.4.2) and consequently to salicylate by isochorismate pyruvate-lyase (EC 4.2.99.21). the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities | Mycobacterium tuberculosis |
| physiological function | the enzyme is involved in the biosynthesis of pyochelin. Chorismate-utilizing enzymes (CUE) such as chorismate mutase, anthranilate synthase, chorismate pyruvate-lyase, 4-amino-4-deoxychorismate synthase, isochorismate synthase and salicylate synthase are responsible for converting chorismate into various products necessary for the survival of bacteria | Pseudomonas aeruginosa |
| physiological function | the enzyme is involved in the biosynthesis of the siderophore mycobactin. Chorismate-utilizing enzymes (CUE) such as chorismate mutase, anthranilate synthase, chorismate pyruvate-lyase, 4-amino-4-deoxychorismate synthase, isochorismate synthase and salicylate synthase are responsible for converting chorismate into various products necessary for the survival of bacteria | Mycobacterium tuberculosis |
| physiological function | the enzyme is involved in the biosynthesis of the siderophore yersiniabactin. Chorismate-utilizing enzymes (CUE) such as chorismate mutase, anthranilate synthase, chorismate pyruvate-lyase, 4-amino-4-deoxychorismate synthase, isochorismate synthase and salicylate synthase are responsible for converting chorismate into various products necessary for the survival of bacteria | Yersinia pestis |
| physiological function | the enzyme is involved in the biosynthesis of the siderophore yersiniabactin. Chorismate-utilizing enzymes (CUE) such as chorismate mutase, anthranilate synthase, chorismate pyruvate-lyase, 4-amino-4-deoxychorismate synthase, isochorismate synthase and salicylate synthase are responsible for converting chorismate into various products necessary for the survival of bacteria | Yersinia enterocolitica |
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