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Literature summary extracted from
- Identification and structure-activity relationship study of carvacrol derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors (2014), J. Enzyme Inhib. Med. Chem., 29, 547-554 .
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | drug development | since vertebrates lack the shikimate pathway for the biosynthesis of aromatic compounds and thus do not possess chorismate mutase activity, the enzyme represents a prime target for the development of antibacterials | Mycobacterium tuberculosis |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 5.4.99.5 | 1-isopropyl-2-methoxy-4-methylbenzene | - |
Mycobacterium tuberculosis |  |
| 5.4.99.5 | 2-isopropyl-5-methylphenyl acetate | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 2-methyl-5-(prop-1-en-2-yl)cyclohexanol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-chloroquinoxaline | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-isopropylphenol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 3-methyl-5-(propan-2-yl)phenol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 4-(3,4-dimethoxyphenethylamino)-3-nitro-5-sulfamoylbenzoic acid | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | 5-isopropyl-2-methylaniline | - |
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 | carvacrol | lead compound | Mycobacterium tuberculosis | |
| 5.4.99.5 | eugenol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | menthol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | additional information | identification and structure-activity relationship study of carvacrol derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors, structure-based e-pharmacophore modeling, overview. Database screening using the crystal structure of the MTB CM bound transition state intermediate (PDB ID 2FP2) as framework. No inhibition by 3-(6-(benzyloxy)-1H-indol-1-yl)propanoic acid, 5-isopropyl-2-methylphenyl acetate, 4-bromo-5-isopropyl-2-methylphenol, 4-nitro-5-isopropyl-2-methylphenol, 4-isopropyl-2-methoxy-1-methylbenzene, 4-bromo-2-isopropyl-5-methylphenol, 4-nitro-2-isopropyl-5-methylphenol, and 4-chloro-2-isopropyl-5-methylphenol | Mycobacterium tuberculosis | |
| 5.4.99.5 | N-[(3-(2-amino-3-cyano-2H-benzo[h]chromen-4-y))phenyl]methylidyne]-2-hydroxyethanaminium | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | neoisopulegol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | o-Cresol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | p-cymene | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | Thymol | - |
Mycobacterium tuberculosis | |
| 5.4.99.5 | Vanillin | - |
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 | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 5.4.99.5 | Mycobacterium tuberculosis | P9WIB9 | - |
- |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 5.4.99.5 | Chorismate = prephenate | the enzyme catalyzes the conversion of chorismate to prephenate, which is formally a Claisen rearrangement that proceeds via an endo-oxabicyclic transition state with a chair-like geometry | Mycobacterium tuberculosis |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 5.4.99.5 | Chorismate | - |
Mycobacterium tuberculosis | Prephenate | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | MTB CM | - |
Mycobacterium tuberculosis |
Ki Value [mM]
| EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | 0.0057 | - |
4-(3,4-dimethoxyphenethylamino)-3-nitro-5-sulfamoylbenzoic acid | pH and temperature not specified in the publication | Mycobacterium tuberculosis | |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 5.4.99.5 | 0.00106 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | carvacrol | |
| 5.4.99.5 | 0.00408 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 2-isopropyl-5-methylphenyl acetate | |
| 5.4.99.5 | 0.0116 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | p-cymene | |
| 5.4.99.5 | 0.01363 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 2-methyl-5-(prop-1-en-2-yl)cyclohexanol | |
| 5.4.99.5 | 0.01513 | - |
pH and temperature not specified in the publication | 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 and temperature not specified in the publication | Mycobacterium tuberculosis | N-[(3-(2-amino-3-cyano-2H-benzo[h]chromen-4-y))phenyl]methylidyne]-2-hydroxyethanaminium | |
| 5.4.99.5 | 0.01974 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 3-chloroquinoxaline | |
| 5.4.99.5 | 0.0214 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 3-isopropylphenol | |
| 5.4.99.5 | 0.02158 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 1-isopropyl-2-methoxy-4-methylbenzene | |
| 5.4.99.5 | 0.0231 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | o-Cresol | |
| 5.4.99.5 | 0.0248 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | Vanillin | |
| 5.4.99.5 | 0.02638 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | menthol | |
| 5.4.99.5 | 0.02677 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | 3-methyl-5-(propan-2-yl)phenol | |
| 5.4.99.5 | 0.0284 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | Thymol | |
| 5.4.99.5 | 0.02858 | - |
pH and temperature not specified in the publication | Mycobacterium tuberculosis | eugenol | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 5.4.99.5 | metabolism | chorismate mutase is located at the branch point of the shikimate pathway and channels chorismate into the Tyr/Phe-specific branch. The enzyme catalyzes the conversion of chorismate to prephenate | Mycobacterium tuberculosis |
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