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Literature summary extracted from

  • Sampson, P.B.; Picard, C.; Handerson, S.; McGrath, T.E.; Domagala, M.; Leeson, A.; Romanov, V.; Awrey, D.E.; Thambipillai, D.; Bardouniotis, E.; Kaplan, N.; Berman, J.M.; Pauls, H.W.
    Spiro-naphthyridinone piperidines as inhibitors of S. aureus and E. coli enoyl-ACP reductase (FabI) (2009), Bioorg. Med. Chem. Lett., 19, 5355-5358.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.3.1.9 medicine targeting bacterial fatty acid biosynthesis is a viable approach to new antimicrobial agents Staphylococcus aureus
1.3.1.9 medicine targeting bacterial fatty acid biosynthesis is a viable approach to new antimicrobial agents Escherichia coli

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.1.9 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-[3-(2-morpholin-4-ylethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl]prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-[3-(2-morpholin-4-ylethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl]prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 (2E)-N-[(5-fluoro-3-methyl-1-benzothiophen-2-yl)methyl]-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 (2E)-N-[(5-fluoro-3-methyl-1-benzothiophen-2-yl)methyl]-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 cerulenin
-
 Escherichia coli
1.3.1.9 cerulenin
-
 Staphylococcus aureus
1.3.1.9 triclosan
-
 Escherichia coli
1.3.1.9 triclosan
-
 Staphylococcus aureus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.3.1.9 enoyl-ACP + NADH + H+ Staphylococcus aureus
-
 acyl-ACP + NAD+
-
 ?
1.3.1.9 enoyl-ACP + NADH + H+ Escherichia coli
-
 acyl-ACP + NAD+
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.3.1.9 Escherichia coli
-
-
-
1.3.1.9 Staphylococcus aureus
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.1.9 crotonyl-CoA + NAD+ activity assay Escherichia coli butyryl-CoA + NADH + H+
-
 ?
1.3.1.9 enoyl-ACP + NADH + H+
-
 Staphylococcus aureus acyl-ACP + NAD+
-
 ?
1.3.1.9 enoyl-ACP + NADH + H+
-
 Escherichia coli acyl-ACP + NAD+
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.3.1.9 enoyl-ACP reductase
-
 Staphylococcus aureus
1.3.1.9 enoyl-ACP reductase
-
 Escherichia coli
1.3.1.9 FabI
-
 Staphylococcus aureus
1.3.1.9 FabI
-
 Escherichia coli

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.3.1.9 7.2
-
 activity assay Escherichia coli

Cofactor

EC Number Cofactor Comment Organism Structure
1.3.1.9 NADH
-
 Staphylococcus aureus
1.3.1.9 NADH
-
 Escherichia coli

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.3.1.9 0.0000004
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.0000007
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-[3-(2-morpholin-4-ylethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl]prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.0000018
-
 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.0000024
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.000007
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-[3-(2-morpholin-4-ylethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl]prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.000014
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000017
-
 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.00002
-
 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000024
-
 (2E)-N-[(5-fluoro-3-methyl-1-benzothiophen-2-yl)methyl]-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.000026
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-[3-(2-morpholin-4-ylethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl]prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000026
-
 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000028
-
 (2E)-N-[(5-fluoro-3-methyl-1-benzothiophen-2-yl)methyl]-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.00003
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000048
-
 (2E)-N-methyl-N-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000049
-
 (2E)-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000055
-
 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(1'-methyl-2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Escherichia coli
1.3.1.9 0.000071
-
 (2E)-N-(3-methoxy-2-propoxybenzyl)-N-methyl-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus
1.3.1.9 0.000132
-
 (2E)-N-methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-3-(2-oxo-1,4-dihydro-2H-spiro[1,8-naphthyridine-3,4'-piperidin]-6-yl)prop-2-enamide
-
 Staphylococcus aureus