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MetaCyc 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): 60.15568Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
diisopropyl fluorophosphate + H2O → diisopropyl phosphate + fluoride + 2 H+

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: NADPH-dependent curcumin reductase [Hassaninasab11], serine protease [Waxman85], tail-specific protease [Park88b], serine protease [Maurizi90], 6-aminohexanoate oligomermer exohydrolase [Kanagawa93], poly(3-hydroxybutyrate) depolymerase [Handrick01], N-cyclohexylformamide hydratase [Goda01], (25R)-3α,7α,12α-trihydroxy-5β-cholestanoyl-CoA racemase [Schmitz94], 13-sophorosyloxydocosanoate 6',6''-diacetate acetylesterase [Bucholtz76], 6-aminohexanoate linear dimer hydrolase [Kanagawa93], triacylglycerol lipase [Eastmond06] Inhibitor (Other types) of: (+)-bornyl diphosphate synthase [Croteau79]

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

Bucholtz76: Bucholtz ML, Light RJ (1976). "Hydrolysis of 13-sophorosyloxydocosanoic acid esters by acetyl- and carboxylesterases isolated from Candida bororiensis." J Biol Chem 251(2);431-7. PMID: 1245482

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

Croteau79: Croteau R, Karp F (1979). "Biosynthesis of monoterpenes: preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that Geranyl pyrophosphate is the preferred substrate for cyclization." Arch Biochem Biophys 198(2);512-22. PMID: 42356

Eastmond06: Eastmond PJ (2006). "SUGAR-DEPENDENT1 encodes a patatin domain triacylglycerol lipase that initiates storage oil breakdown in germinating Arabidopsis seeds." Plant Cell 18(3);665-75. PMID: 16473965

Goda01: Goda M, Hashimoto Y, Shimizu S, Kobayashi M (2001). "Discovery of a novel enzyme, isonitrile hydratase, involved in nitrogen-carbon triple bond cleavage." J Biol Chem 276(26);23480-5. PMID: 11306561

Handrick01: Handrick R, Reinhardt S, Focarete ML, Scandola M, Adamus G, Kowalczuk M, Jendrossek D (2001). "A new type of thermoalkalophilic hydrolase of Paucimonas lemoignei with high specificity for amorphous polyesters of short chain-length hydroxyalkanoic acids." J Biol Chem 276(39);36215-24. PMID: 11457823

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

Kanagawa93: Kanagawa K, Oishi M, Negoro S, Urabe I, Okada H (1993). "Characterization of the 6-aminohexanoate-dimer hydrolase from Pseudomonas sp. NK87." J Gen Microbiol 139 ( Pt 4);787-95. PMID: 8515236

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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

Park88b: 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

Schmitz94: Schmitz W, Fingerhut R, Conzelmann E (1994). "Purification and properties of an alpha-methylacyl-CoA racemase from rat liver." Eur J Biochem 222(2);313-23. PMID: 8020470

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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