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Literature summary for 2.3.1.293 extracted from

  • Kapilashrami, K.; Bommineni, G.R.; Machutta, C.A.; Kim, P.; Lai, C.T.; Simmerling, C.; Picart, F.; Tonge, P.J.
    Thiolactomycin-based beta-ketoacyl-AcpM synthase A (KasA) inhibitors: fragment-based inhibitor discovery using transient one-dimensional nuclear overhauser effect NMR spectroscopy (2013), J. Biol. Chem., 288, 6045-6052.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.3.1.293

Cloned(Commentary)

Cloned (Comment) Organism
gene kasA, recombinant expression in Mycobacterium smegmatis strain mc2155 Mycobacterium tuberculosis

Protein Variants

Protein Variants Comment Organism
C171Q site-directed mutagenesis, ligand binding and active site structure analysis Mycobacterium tuberculosis

Inhibitors

Inhibitors Comment Organism Structure
(5R)-3-acetyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-butanoyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-ethyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-hexadecanoyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-[2-(4-chlorophenyl)ethyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-[4-(4-chlorophenyl)butyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-[4-(4-fluorophenyl)butyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-[4-([1,1'-biphenyl]-4-yl)butyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-3-[6-([1,1'-biphenyl]-4-yl)hexanoyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-3-(propan-2-yl)thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-3-(trifluoroacetyl)thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-3-[2-(4-methylphenyl)ethyl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one
-
 Mycobacterium tuberculosis
2-[(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2-oxo-2,5-dihydrothiophene-3-carbonyl]benzoic acid
-
 Mycobacterium tuberculosis
4-[(4-fluorobenzene-1-sulfonyl)amino]-N-[[1-(4-[(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2-oxo-2,5-dihydrothiophen-3-yl]butyl)-1H-1,2,3-triazol-4-yl]methyl]benzamide
-
 Mycobacterium tuberculosis
cerulenin natural product inhibitor Mycobacterium tuberculosis
methyl (5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2-oxo-2,5-dihydrothiophene-3-carboxylate
-
 Mycobacterium tuberculosis
platensimycin natural product inhibitor Mycobacterium tuberculosis
thiolactomycin natural product inhibitor, binding analysis with wild-type and mutant enzymes, overview. Structure-activity relationships of thiolactomycin and derivatives Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
an acyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein] Mycobacterium tuberculosis
-
 a 3-oxoacyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
-
 ?

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
an acyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein]
-
 Mycobacterium tuberculosis a 3-oxoacyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]
-
 ?

Synonyms

Synonyms Comment Organism
beta-ketoacyl-AcpM synthase A
-
 Mycobacterium tuberculosis
KasA
-
 Mycobacterium tuberculosis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.008
-
 (5R)-3-[6-([1,1'-biphenyl]-4-yl)hexanoyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0082
-
 (5R)-3-acetyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0121
-
 (5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-3-(trifluoroacetyl)thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0138
-
 (5R)-3-[4-([1,1'-biphenyl]-4-yl)butyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0219
-
 methyl (5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2-oxo-2,5-dihydrothiophene-3-carboxylate pH and temperature not specified in the publication Mycobacterium tuberculosis
0.032
-
 4-[(4-fluorobenzene-1-sulfonyl)amino]-N-[[1-(4-[(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2-oxo-2,5-dihydrothiophen-3-yl]butyl)-1H-1,2,3-triazol-4-yl]methyl]benzamide pH and temperature not specified in the publication Mycobacterium tuberculosis
0.047
-
 (5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0652
-
 (5R)-3-butanoyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.069
-
 (5R)-3-[4-(4-fluorophenyl)butyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0774
-
 (5R)-3-[4-(4-chlorophenyl)butyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.0928
-
 (5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-3-[2-(4-methylphenyl)ethyl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.102
-
 2-[(5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2-oxo-2,5-dihydrothiophene-3-carbonyl]benzoic acid pH and temperature not specified in the publication Mycobacterium tuberculosis
0.105
-
 (5R)-3-hexadecanoyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.1754
-
 thiolactomycin pH and temperature not specified in the publication Mycobacterium tuberculosis
0.305
-
 (5R)-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-3-(propan-2-yl)thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.357
-
 (5R)-3-ethyl-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis
0.4
-
 (5R)-3-[2-(4-chlorophenyl)ethyl]-4-hydroxy-5-methyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]thiophen-2(5H)-one pH and temperature not specified in the publication Mycobacterium tuberculosis

General Information

General Information Comment Organism
metabolism an essential enzyme in the mycobacterial fatty acid biosynthesis (FAS-II) pathway, type II fatty acid biosynthesis pathway overview Mycobacterium tuberculosis