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Literature summary for 1.3.1.9 extracted from

  • Seefeld, M.A.; Miller, W.H.; Newlander, K.A.; Burgess, W.J.; DeWolf, W.E., Jr.; Elkins, P.A.; Head, M.S.; Jakas, D.R.; Janson, C.A.; Keller, P.M.; Manley, P.J.; Moore, T.D.; Payne, D.J.; Pearson, S.; Polizzi, B.J.; Qiu, X.; Rittenhouse, S.F.; Uzinskas, I.N.; Wallis, N.G.; Huffman, W.F.
    Indole naphthyridinones as inhibitors of bacterial enoyl-ACP reductases FabI and FabK (2003), J. Med. Chem., 46, 1627-1635.
    View publication on PubMed

Crystallization (Commentary)

Crystallization (Comment) Organism
crystals of FabI/NAD+ complex with (E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthydrin-3-yl)acrylamide diffract to 2.3 A Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
(E)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide 0.00007 mM, 50% inhibition Haemophilus influenzae
(E)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphtyridin-3-yl)-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide 0.00002 mM, 50% inhibition Staphylococcus aureus
(E)-N-methyl-N-(1,2-dimethyl-1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.000025 mM, 50% inhibition Haemophilus influenzae
(E)-N-methyl-N-(1,2-dimethyl-1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.00006 mM, 50% inhibition Staphylococcus aureus
(E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.0006 mM, 50% inhibition Haemophilus influenzae
(E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.00005 mM, 50% inhibition Staphylococcus aureus
(E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.0004 mM, 50% inhibition Haemophilus influenzae
(E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.0001 mM, 50% inhibition Staphylococcus aureus
(E)-N-methyl-N-(1-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.005 mM, 50% inhibition Streptococcus pneumoniae
(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.00013 mM, 50% inhibition Haemophilus influenzae
(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.00005 mM, 50% inhibition Staphylococcus aureus
(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 0.006 mM, 50% inhibition Streptococcus pneumoniae
triclosan 0.00007 mM, 50% inhibition Staphylococcus aureus

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Haemophilus influenzae
-
-
-
Staphylococcus aureus
-
-
-
Streptococcus pneumoniae
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
trans-2-dodecenoyl-ACP + NADH
-
Staphylococcus aureus dodecanoyl-ACP + NAD+
-
?
trans-2-dodecenoyl-[acyl-carrier protein] + NADH
-
Escherichia coli dodecanoyl-ACP + NAD+
-
?
trans-2-dodecenoyl-[acyl-carrier protein] + NADH
-
Streptococcus pneumoniae dodecanoyl-ACP + NAD+
-
?
trans-2-dodecenoyl-[acyl-carrier protein] + NADH
-
Haemophilus influenzae dodecanoyl-[acyl-carrier protein] + NAD+
-
?

Synonyms

Synonyms Comment Organism
FabI
-
Escherichia coli
FabK
-
Streptococcus pneumoniae

Cofactor

Cofactor Comment Organism Structure
NADH
-
Staphylococcus aureus
NADH
-
Haemophilus influenzae
NADH
-
Escherichia coli
NADH
-
Streptococcus pneumoniae

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000023
-
(E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 30°C, pH 6.5 Staphylococcus aureus
0.0000043
-
(E)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide 30°C, pH 6.5 Haemophilus influenzae