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((Z)-octadec-9-enylcarbamoyl)methylphosphonic acid
(heptylcarbamoyl)methylphosphonic acid
0.2 mM, 98% inhibition, pH 7.4, 37°C
(N-dodecyl-N-methylcarbamoyl)methylphosphonic acid
(Z)-1,1-difluoro-2-oxononadec-10-enylphosphonic acid
(Z)-1-oxooctadec-11-enylphosphoramidic acid
-
0.2 mM, 93% inhibition, pH 7.4, 37°C
(Z)-2-oxononadec-12-enylphosphonic acid
1,1-difluoro-2-oxododec-11-enylphosphonic acid
1,1-difluoro-2-oxoheptadecylphosphonic acid
1,1-difluoro-2-oxotridecylphosphonic acid
1-hexadecanoyl-sn-glycerol 3-phosphate
product inhibitor
1-oxo-11-phenoxyundecylphosphoramidic acid
-
0.2 mM, 47% inhibition, pH 7.4, 37°C
1-oxododecylphosphoramidic acid
-
0.2 mM, 30% inhibition, pH 7.4, 37°C
1-oxohexadecylphosphoramidic acid
-
0.2 mM, 75% inhibition, pH 7.4, 37°C
2-oxo-12-phenoxydodecylphosphonic acid
2-oxo-6-phenylhexylphosphonic acid
-
0.2 mM, 6% inhibition, pH 7.4, 37°C
2-oxoheptadecylphosphonic acid
2-oxopentylphosphonic acid
-
0.2 mM, 18% inhibition, pH 7.4, 37°C
2-oxotridecylphosphonic acid
4-methoxyphenyl 5-phenylpentanoylsulfamate
4-methoxyphenyl palmitoylsulfamate
4-methoxyphenyl undec-10-enoylsulfamate
5-cyclohexyl-1-oxopentylphosphoramidic acid
-
0.2 mM, 18% inhibition, pH 7.4, 37°C
6-cyclohexyl-2-oxohexylphosphonic acid
-
0.2 mM, 9% inhibition, pH 7.4, 37°C
hexadecanoyl-CoA
noncompetitive inhibitor
phenyl (8-phenyloctanoyl)sulfamate
((Z)-octadec-9-enylcarbamoyl)methylphosphonic acid
0.2 mM, 62% inhibition, pH 7.4, 37°C
((Z)-octadec-9-enylcarbamoyl)methylphosphonic acid
-
0.2 mM, 49% inhibition, pH 7.4, 37°C
(N-dodecyl-N-methylcarbamoyl)methylphosphonic acid
0.2 mM,23 % inhibition, pH 7.4, 37°C
(N-dodecyl-N-methylcarbamoyl)methylphosphonic acid
-
0.2 mM, 64% inhibition, pH 7.4, 37°C
(Z)-1,1-difluoro-2-oxononadec-10-enylphosphonic acid
0.2 mM, 68% inhibition, pH 7.4, 37°C
(Z)-1,1-difluoro-2-oxononadec-10-enylphosphonic acid
-
0.2 mM, 100% inhibition, pH 7.4, 37°C
(Z)-2-oxononadec-12-enylphosphonic acid
0.2 mM, 40% inhibition, pH 7.4, 37°C
(Z)-2-oxononadec-12-enylphosphonic acid
-
0.2 mM, 98% inhibition, pH 7.4, 37°C
1,1-difluoro-2-oxododec-11-enylphosphonic acid
0.2 mM, 29% inhibition, pH 7.4, 37°C
1,1-difluoro-2-oxododec-11-enylphosphonic acid
-
0.2 mM, 14% inhibition, pH 7.4, 37°C
1,1-difluoro-2-oxoheptadecylphosphonic acid
0.2 mM, 91% inhibition, pH 7.4, 37°C
1,1-difluoro-2-oxoheptadecylphosphonic acid
-
0.2 mM, 99% inhibition, pH 7.4, 37°C
1,1-difluoro-2-oxotridecylphosphonic acid
0.2 mM, 100% inhibition, pH 7.4, 37°C
1,1-difluoro-2-oxotridecylphosphonic acid
-
0.2 mM, 48% inhibition, pH 7.4, 37°C
2-oxo-12-phenoxydodecylphosphonic acid
0.2 mM, 55% inhibition, pH 7.4, 37°C
2-oxo-12-phenoxydodecylphosphonic acid
-
0.2 mM, 48% inhibition, pH 7.4, 37°C
2-oxoheptadecylphosphonic acid
0.2 mM, 67% inhibition, pH 7.4, 37°C
2-oxoheptadecylphosphonic acid
-
0.2 mM, 28% inhibition, pH 7.4, 37°C
2-oxotridecylphosphonic acid
0.2 mM, 28% inhibition, pH 7.4, 37°C
2-oxotridecylphosphonic acid
-
0.2 mM, 38% inhibition, pH 7.4, 37°C
4-methoxyphenyl 5-phenylpentanoylsulfamate
0.2 mM, 13% inhibition, pH 7.4, 37°C
4-methoxyphenyl 5-phenylpentanoylsulfamate
-
0.2 mM, 12% inhibition, pH 7.4, 37°C
4-methoxyphenyl palmitoylsulfamate
-
good antimicrobial activity against both Staphylococcus aureus and Bacillus anthracis
4-methoxyphenyl palmitoylsulfamate
0.2 mM, 100% inhibition, pH 7.4, 37°C
4-methoxyphenyl palmitoylsulfamate
-
good antimicrobial activity against both Staphylococcus aureus and Bacillus anthracis
4-methoxyphenyl palmitoylsulfamate
-
0.2 mM, 100% inhibition, pH 7.4, 37°C
4-methoxyphenyl undec-10-enoylsulfamate
-
broad antimicrobial profile with good activity against multiple species of Gram-positive bacteria
4-methoxyphenyl undec-10-enoylsulfamate
-
broad antimicrobial profile with good activity against multiple species of Gram-positive bacteria
butyl palmitoylsulfamate
0.2 mM, 99% inhibition, pH 7.4, 37°C
butyl palmitoylsulfamate
-
0.2 mM, 100% inhibition, pH 7.4, 37°C
ethyl palmitoylsulfamate
0.2 mM, 99% inhibition, pH 7.4, 37°C
ethyl palmitoylsulfamate
-
0.2 mM, 98% inhibition, pH 7.4, 37°C
phenyl (8-phenyloctanoyl)sulfamate
-
good antimicrobial activity against both Staphylococcus aureus and Bacillus anthracis. Compound causes an abrupt cessation of cell growth and inhibits inhibits protein, DNA and RNA synthesis in Bacillus anthracis Sterne
phenyl (8-phenyloctanoyl)sulfamate
-
good antimicrobial activity against both Staphylococcus aureus and Bacillus anthracis. Staphylococcus aureus cell growth does not immediately cease following addition, but slows down over approximately 2 h before stopping completely. Compound causes a concentration dependent decrease in acetate incorporation into fatty acids and membrane phospholipids
additional information
-
data suggest that acylsulfamate inhibitors may have off-target effects on bacterial membrane function
-
additional information
addition of 1 mM EDTA to the reaction does not affect its activity
-
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Hara, Y.; Seki, M.; Matsuoka, S.; Hara, H.; Yamashita, A.; Matsumoto, K.
Involvement of PlsX and the acyl-phosphate dependent sn-glycerol-3-phosphate acyltransferase PlsY in the initial stage of glycerolipid synthesis in Bacillus subtilis
Genes Genet. Syst.
83
433-442
2008
Bacillus subtilis
brenda
Cherian, P.T.; Yao, J.; Leonardi, R.; Maddox, M.M.; Luna, V.A.; Rock, C.O.; Lee, R.E.
Acyl-sulfamates target the essential glycerol-phosphate acyltransferase (PlsY) in Gram-positive bacteria
Bioorg. Med. Chem.
20
4985-4994
2012
Bacillus anthracis, Staphylococcus aureus
brenda
Yoshimura, M.; Oshima, T.; Ogasawara, N.
Involvement of the YneS/YgiH and PlsX proteins in phospholipid biosynthesis in both Bacillus subtilis and Escherichia coli
BMC Microbiol.
7
69
2007
Bacillus subtilis (Q45064), Bacillus subtilis 168 (Q45064)
brenda
Grimes, K.; Lu, Y.; Zhang, Y.; Luna, V.; Hurdle, J.; Carson, E.; Qi, J.; Kudrimoti, S.; Rock, C.; Lee, R.
Novel acyl phosphate mimics that target PlsY, an essential acyltransferase in gram-positive bacteria
ChemMedChem
3
1936-1945
2008
Streptococcus pneumoniae, Bacillus anthracis (Q81QF8), Streptococcus pneumoniae DAW30, Bacillus anthracis Sterne 34F2 (Q81QF8)
brenda
Hara, Y.; Seki, M.; Matsuoka, S.; Hara, H.; Yamashita, A.; Matsumoto, K.
Involvement of PlsX and the acyl-phosphate dependent sn-glycerol-3-phosphate acyltransferase PlsY in the initial stage of glycerolipid synthesis in Bacillus subtilis
Genes Genet. Syst.
83
433-442
2008
Bacillus subtilis (Q45064), Bacillus subtilis 168 (Q45064)
brenda
Lu, Y.; Zhang, F.; Grimes, K.; Lee, R.; Rock, C.
Topology and active site of PlsY The bacterial acylphosphate glycerol-3-phosphate acyltransferase
J. Biol. Chem.
282
11339-11346
2007
Streptococcus pneumoniae (P0A4Q0), Streptococcus pneumoniae ATCC BAA-255 (P0A4Q0)
brenda
Lu, Y.; Zhang, Y.; Grimes, K.; Qi, J.; Lee, R.; Rock, C.
Acyl-phosphates initiate membrane phospholipid synthesis in Gram-positive pathogens
Mol. Cell.
23
765-772
2006
Streptococcus pneumoniae (P0A4Q0), Streptococcus pneumoniae ATCC BAA-255 (P0A4Q0)
brenda