Literature summary for 5.4.99.5 extracted from

Alokam, R.; Jeankumar, V.; Sridevi, J.; Matikonda, S.; Peddi, S.; Alvala, M.; Yogeeswari, P.; Sriram, D.
Identification and structure-activity relationship study of carvacrol derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors (2014), J. Enzyme Inhib. Med. Chem., 29, 547-554 .

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Application

Application	Comment	Organism
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

Inhibitors	Comment	Organism	Structure
1-isopropyl-2-methoxy-4-methylbenzene	-	Mycobacterium tuberculosis
2-isopropyl-5-methylphenyl acetate	-	Mycobacterium tuberculosis
2-methyl-5-(prop-1-en-2-yl)cyclohexanol	-	Mycobacterium tuberculosis
3-chloroquinoxaline	-	Mycobacterium tuberculosis
3-isopropylphenol	-	Mycobacterium tuberculosis
3-methyl-5-(propan-2-yl)phenol	-	Mycobacterium tuberculosis
4-(3,4-dimethoxyphenethylamino)-3-nitro-5-sulfamoylbenzoic acid	-	Mycobacterium tuberculosis
5-isopropyl-2-methylaniline	-	Mycobacterium tuberculosis
5-naphthyl-7-propyl-3H-pyrazolo[4,3-d][1,2,3]triazin-4(5H)-one	-	Mycobacterium tuberculosis
carvacrol	lead compound	Mycobacterium tuberculosis
eugenol	-	Mycobacterium tuberculosis
menthol	-	Mycobacterium tuberculosis
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
N-[(3-(2-amino-3-cyano-2H-benzo[h]chromen-4-y))phenyl]methylidyne]-2-hydroxyethanaminium	-	Mycobacterium tuberculosis
neoisopulegol	-	Mycobacterium tuberculosis
o-Cresol	-	Mycobacterium tuberculosis
p-cymene	-	Mycobacterium tuberculosis
Thymol	-	Mycobacterium tuberculosis
Vanillin	-	Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

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

Organism

Organism	UniProt	Comment	Textmining
Mycobacterium tuberculosis	P9WIB9	-	-

Reaction

Reaction	Comment	Organism	Reaction ID
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	a

Source Tissue

Source Tissue	Comment	Organism	Textmining

Substrates and Products (Substrate)

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

Synonyms

Synonyms	Comment	Organism
MTB CM	-	Mycobacterium tuberculosis

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
0.0057	-	4-(3,4-dimethoxyphenethylamino)-3-nitro-5-sulfamoylbenzoic acid	pH and temperature not specified in the publication	Mycobacterium tuberculosis

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
0.00106	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	carvacrol
0.00408	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	2-isopropyl-5-methylphenyl acetate
0.0116	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	p-cymene
0.01363	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	2-methyl-5-(prop-1-en-2-yl)cyclohexanol
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
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
0.01974	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	3-chloroquinoxaline
0.0214	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	3-isopropylphenol
0.02158	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	1-isopropyl-2-methoxy-4-methylbenzene
0.0231	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	o-Cresol
0.0248	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	Vanillin
0.02638	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	menthol
0.02677	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	3-methyl-5-(propan-2-yl)phenol
0.0284	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	Thymol
0.02858	-	pH and temperature not specified in the publication	Mycobacterium tuberculosis	eugenol

General Information

General Information	Comment	Organism
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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Release 2023.1 (January 2023)