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Escherichia coli K-12 substr. MG1655 Compound: diisopropyl fluorophosphate

Chemical Formula: C6H14O3FP

Molecular Weight: 184.15 Daltons

Monoisotopic Molecular Weight: 184.06645902570003 Daltons

diisopropyl fluorophosphate compound structure

SMILES: CC(C)OP(=O)(F)OC(C)C

InChI: InChI=1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3

InChIKey: InChIKey=MUCZHBLJLSDCSD-UHFFFAOYSA-N

Unification Links: ChEBI:17941, ChemSpider:5723, DrugBank:DB00677, HMDB:HMDB14815, KEGG:C00202, PubChem:5936

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -83.64

Enzymes inhibited by diisopropyl fluorophosphate, sorted by the type of inhibition, are:

Inhibitor (Irreversible) of: acyl-CoA thioesterase [Barnes68], lysophospholipase [Cho94] Inhibitor (Mechanism unknown) of: serine protease [Waxman85], tail-specific protease [Park88], serine protease [Maurizi90], NADPH-dependent curcumin reductase [Hassaninasab11]

References

Barnes68: Barnes EM, Wakil SJ (1968). "Studies on the mechanism of fatty acid synthesis. XIX. Preparation and general properties of palmityl thioesterase." J Biol Chem 1968;243(11);2955-62. PMID: 4871199

Cho94: Cho H, Cronan JE (1994). ""Protease I" of Escherichia coli functions as a thioesterase in vivo." J Bacteriol 176(6);1793-5. PMID: 8132479

Hassaninasab11: Hassaninasab A, Hashimoto Y, Tomita-Yokotani K, Kobayashi M (2011). "Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism." Proc Natl Acad Sci U S A 108(16):6615-20. PMID: 21467222

Maurizi90: Maurizi MR, Clark WP, Kim SH, Gottesman S (1990). "Clp P represents a unique family of serine proteases." J Biol Chem 265(21);12546-52. PMID: 2197276

Park88: Park JH, Lee YS, Chung CH, Goldberg AL (1988). "Purification and characterization of protease Re, a cytoplasmic endoprotease in Escherichia coli." J Bacteriol 170(2);921-6. PMID: 2892828

Waxman85: Waxman L, Goldberg AL (1985). "Protease La, the lon gene product, cleaves specific fluorogenic peptides in an ATP-dependent reaction." J Biol Chem 260(22);12022-8. PMID: 3900067


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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