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Literature summary extracted from

  • Devi, P.B.; Samala, G.; Sridevi, J.P.; Saxena, S.; Alvala, M.; Salina, E.G.; Sriram, D.; Yogeeswari, P.
    Structure-guided design of thiazolidine derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors (2014), ChemMedChem, 9, 2538-2547 .
    View publication on PubMed

Application

EC Number Application Comment Organism
6.3.2.1 drug development the enzyme is an appropriate target for development of therapeutics to treat tuberculosis Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.3.2.1 (3E)-3-[2-[(cyclohexylamino)(oxo)acetyl]hydrazinylidene]-N-[(4-methoxyphenyl)methyl]butanamide
-
 Mycobacterium tuberculosis
6.3.2.1 (3Z)-3-[2-[3-([(E)-[(4-methoxyphenyl)methylidene]amino]oxy)prop-1-en-2-yl]hydrazinylidene]-1,3-dihydro-2H-indol-2-one
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(4-oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazolidin-3-yl)propanoyl)-1-naphthohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(4-oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazolidin-3-yl)propanoyl)benzohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(4-oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazolidin-3-yl)propanoyl)isonicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(4-oxo-2-thioxo-5-(3,4,5-trimethoxybenzylidene)thiazolidin-3-yl)propanoyl)nicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-(benzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)-1-naphthohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-(benzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)benzohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-(benzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)isonicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-(benzyloxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)nicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-chlorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)-1-naphthohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-chlorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)benzohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-chlorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)isonicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-chlorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)nicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-propanoyl)-1-naphthohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-propanoyl)benzohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-propanoyl)isonicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(4-nitrobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-propanoyl)nicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)-1-naphthohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)benzohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)isonicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 (Z)-N'-(3-(5-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)nicotinohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 ethyl 2-[[(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino]-1,3-benzothiazole-6-carboxylate
-
 Mycobacterium tuberculosis
6.3.2.1 additional information using energy-based pharmacophore modeling and in vitro screening, structure-guided design (PDB ID 1N2I)and synthesis of thiazolidine derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors from a rational inhibitor design approach, overview Mycobacterium tuberculosis
6.3.2.1 N'-([[5-(4-hydroxyphenyl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl]acetyl)pyridine-4-carbohydrazide
-
 Mycobacterium tuberculosis
6.3.2.1 N-[2-(cyclohexylamino)-1-(3,4-dihydroxyphenyl)-2-oxoethyl]-2-([2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]sulfanyl)-N-phenylacetamide
-
 Mycobacterium tuberculosis
6.3.2.1 [4-[2-(3,4-dihydroxyphenyl)-4-phenyl-1H-imidazol-5-yl]phenyl](phenyl)methanone
-
 Mycobacterium tuberculosis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
6.3.2.1 Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
6.3.2.1 ATP + (R)-pantoate + beta-alanine Mycobacterium tuberculosis
-
 AMP + diphosphate + (R)-pantothenate
-
 ?
6.3.2.1 ATP + (R)-pantoate + beta-alanine Mycobacterium tuberculosis ATCC 27294 / ATCC 25618 / H37Rv
-
 AMP + diphosphate + (R)-pantothenate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
6.3.2.1 Mycobacterium tuberculosis P9WIL5
-
-
6.3.2.1 Mycobacterium tuberculosis ATCC 27294 / ATCC 25618 / H37Rv P9WIL5
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
6.3.2.1 ATP + (R)-pantoate + beta-alanine
-
 Mycobacterium tuberculosis AMP + diphosphate + (R)-pantothenate
-
 ?
6.3.2.1 ATP + (R)-pantoate + beta-alanine
-
 Mycobacterium tuberculosis ATCC 27294 / ATCC 25618 / H37Rv AMP + diphosphate + (R)-pantothenate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
6.3.2.1 PanC
-
 Mycobacterium tuberculosis
6.3.2.1 Pantothenate synthetase
-
 Mycobacterium tuberculosis
6.3.2.1 Rv3602c
-
 Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
6.3.2.1 37
-
 assay at Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
6.3.2.1 7.8
-
 assay at Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
6.3.2.1 ATP
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
6.3.2.1 0.0012
-
 pH 7.8, 37°C Mycobacterium tuberculosis (Z)-N'-(3-(5-(benzo[d][1,3]dioxol-5-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)propanoyl)nicotinohydrazide
6.3.2.1 0.00597
-
 pH 7.8, 37°C Mycobacterium tuberculosis (3Z)-3-[2-[3-([(E)-[(4-methoxyphenyl)methylidene]amino]oxy)prop-1-en-2-yl]hydrazinylidene]-1,3-dihydro-2H-indol-2-one
6.3.2.1 0.00767
-
 pH 7.8, 37°C Mycobacterium tuberculosis ethyl 2-[[(2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino]-1,3-benzothiazole-6-carboxylate
6.3.2.1 0.00892
-
 pH 7.8, 37°C Mycobacterium tuberculosis (3E)-3-[2-[(cyclohexylamino)(oxo)acetyl]hydrazinylidene]-N-[(4-methoxyphenyl)methyl]butanamide
6.3.2.1 0.02472
-
 pH 7.8, 37°C Mycobacterium tuberculosis [4-[2-(3,4-dihydroxyphenyl)-4-phenyl-1H-imidazol-5-yl]phenyl](phenyl)methanone
6.3.2.1 0.02633
-
 pH 7.8, 37°C Mycobacterium tuberculosis N'-([[5-(4-hydroxyphenyl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl]acetyl)pyridine-4-carbohydrazide
6.3.2.1 0.03878
-
 pH 7.8, 37°C Mycobacterium tuberculosis N-[2-(cyclohexylamino)-1-(3,4-dihydroxyphenyl)-2-oxoethyl]-2-([2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]sulfanyl)-N-phenylacetamide

General Information

EC Number General Information Comment Organism
6.3.2.1 physiological function the pantothenate biosynthetic pathway is essential for the persistent growth and virulence of Mycobacterium tuberculosis and one of the enzymes in the pathway Mycobacterium tuberculosis