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Literature summary for 6.1.1.5 extracted from

  • Crasto, C.F.; Forrest, A.K.; Karoli, T.; March, D.R.; Mensah, L.; O'Hanlon, P.J.; Nairn, M.R.; Oldham, M.D.; Yue, W.; Banwell, M.G.; Easton, C.J.
    Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207 (2003), Bioorg. Med. Chem., 11, 2687-2694.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
7-[3-[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]propanoyl-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 10% inhibition at 0.1 mM Rattus norvegicus
7-[4-[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]butanoyl-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 18% inhibition at 0.1 mM Rattus norvegicus
7-[4-[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]butanoyl-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 26% inhibition at 0.1 mM Staphylococcus aureus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]acetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 17% inhibition at 0.1 mM Rattus norvegicus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide
-
Rattus norvegicus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide
-
Staphylococcus aureus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxylic acid methyl ester derivative of SB-203207, 49% inhibition at 0.1 mM Rattus norvegicus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxylic acid methyl ester derivative of SB-203207, 31% inhibition at 0.1 mM Staphylococcus aureus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-4,4a,5,6,7,7a-hexahydro-1-methyl-1H-cyclopenta[b]pyridine-3-carboxylic acid methyl ester derivative of SB-203207, 46% inhibition at 0.1 mM Rattus norvegicus
7-[[(2S,3S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-4,4a,5,6,7,7a-hexahydro-1-methyl-1H-cyclopenta[b]pyridine-3-carboxylic acid methyl ester derivative of SB-203207, 34% inhibition at 0.1 mM Staphylococcus aureus
7-[[(S)-2-amino-1-oxo-5-thiahexyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 31% inhibition at 0.1 mM Rattus norvegicus
7-[[(S)-2-amino-1-oxo-5-thiahexyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 38% inhibition at 0.1 mM Staphylococcus aureus
7-[[(S)-2-amino-1-oxo-hexyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 17% inhibition at 0.1 mM Rattus norvegicus
7-[[(S)-2-amino-1-oxo-hexyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxamide derivative of SB-203207, 46% inhibition at 0.1 mM Staphylococcus aureus
7-[[(S)-2-amino-3-methyl-1-oxobutyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxylic acid methyl ester derivative of SB-203207, 31% inhibition at 0.1 mM Rattus norvegicus
7-[[(S)-2-amino-3-methyl-1-oxobutyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxylic acid methyl ester derivative of SB-203207, 38% inhibition at 0.1 mM Staphylococcus aureus
7-[[(S)-2-amino-3-methyl-1-oxobutyl]amino]sulfonylacetyloxy-4,4a,5,6,7,7a-hexahydro-1-methyl-1H-cyclopenta[b]pyridine-3-carboxylic acid methyl ester derivative of SB-203207, 33% inhibition at 0.1 mM Rattus norvegicus
7-[[(S)-2-amino-3-methyl-1-oxobutyl]amino]sulfonylacetyloxy-4,4a,5,6,7,7a-hexahydro-1-methyl-1H-cyclopenta[b]pyridine-3-carboxylic acid methyl ester derivative of SB-203207, 10% inhibition at 0.1 mM Staphylococcus aureus
7-[[(S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-4,4a,5,6,7,7a-hexahydro-1-methyl-1H-cyclopenta[b]pyridine-3-carboxylic acid methyl ester derivative of SB-203207, 13% inhibition at 0.1 mM Rattus norvegicus
7-[[(S)-2-amino-3-methyl-1-oxopentyl]amino]sulfonylacetyloxy-4,4a,5,6,7,7a-hexahydro-1-methyl-1H-cyclopenta[b]pyridine-3-carboxylic acid methyl ester derivative of SB-203207, 15% inhibition at 0.1 mM Staphylococcus aureus
7-[[(S)-2-amino-4-methyl-1-oxopentyl]amino]sulfonylacetyloxy-2,4a,5,6,7,7a-hexahydro-2-methyl-1H-cyclopenta[c]pyridine-4-carboxylic acid methyl ester derivative of SB-203207, 14% inhibition at 0.1 mM Rattus norvegicus
additional information diverse analogues of SB-203207 are not inhibitory, overview Rattus norvegicus
additional information diverse analogues of SB-203207 are not inhibitory, overview Staphylococcus aureus
SB-203207 anti-infective agent, isolated from Streptomyces NCIMB 40513, analogous to the reaction intermediate Rattus norvegicus
SB-203207 anti-infective agent, isolated from Streptomyces NCIMB 40513, analogous to the reaction intermediate Staphylococcus aureus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
ATP + L-isoleucine + tRNAIle Staphylococcus aureus
-
AMP + diphosphate + L-isoleucyl-tRNAIle
-
?
ATP + L-isoleucine + tRNAIle Rattus norvegicus
-
AMP + diphosphate + L-isoleucyl-tRNAIle
-
?
ATP + L-isoleucine + tRNAIle Staphylococcus aureus WCUH29
-
AMP + diphosphate + L-isoleucyl-tRNAIle
-
?

Organism

Organism UniProt Comment Textmining
Rattus norvegicus
-
-
-
Staphylococcus aureus
-
-
-
Staphylococcus aureus WCUH29
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
liver
-
Rattus norvegicus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
ATP + L-isoleucine + tRNAIle
-
Staphylococcus aureus AMP + diphosphate + L-isoleucyl-tRNAIle
-
?
ATP + L-isoleucine + tRNAIle
-
Rattus norvegicus AMP + diphosphate + L-isoleucyl-tRNAIle
-
?
ATP + L-isoleucine + tRNAIle
-
Staphylococcus aureus WCUH29 AMP + diphosphate + L-isoleucyl-tRNAIle
-
?

Synonyms

Synonyms Comment Organism
IleRS
-
Staphylococcus aureus
IleRS
-
Rattus norvegicus
IRS
-
Staphylococcus aureus
IRS
-
Rattus norvegicus
Isoleucine translase
-
Staphylococcus aureus
Isoleucine translase
-
Rattus norvegicus
Isoleucine--tRNA ligase
-
Staphylococcus aureus
Isoleucine--tRNA ligase
-
Rattus norvegicus
Isoleucine-transfer RNA ligase
-
Staphylococcus aureus
Isoleucine-transfer RNA ligase
-
Rattus norvegicus
Isoleucine-tRNA synthetase
-
Staphylococcus aureus
Isoleucine-tRNA synthetase
-
Rattus norvegicus
Isoleucyl-transfer ribonucleate synthetase
-
Staphylococcus aureus
Isoleucyl-transfer ribonucleate synthetase
-
Rattus norvegicus
Isoleucyl-transfer RNA synthetase
-
Staphylococcus aureus
Isoleucyl-transfer RNA synthetase
-
Rattus norvegicus
Isoleucyl-tRNA synthetase
-
Staphylococcus aureus
Isoleucyl-tRNA synthetase
-
Rattus norvegicus
Mupirocin resistance protein
-
Staphylococcus aureus
Mupirocin resistance protein
-
Rattus norvegicus
Synthetase, isoleucyl-transfer ribonucleate
-
Staphylococcus aureus
Synthetase, isoleucyl-transfer ribonucleate
-
Rattus norvegicus

Cofactor

Cofactor Comment Organism Structure
ATP
-
Staphylococcus aureus
ATP
-
Rattus norvegicus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
additional information
-
Staphylococcus aureus
additional information
-
additional information
-
Rattus norvegicus