Paraoxon
Not truly a substrate but an inhibitor of some alpha/beta hydrolases and other serine hydrolases. Substrate of paraoxonase and phosphotriesterases which are not alpha/beta hydrolases. Some mutants of BCHE butyrylcholinesterases have been developped which can hydrolyse paraoxon. Pesticide. Results from the metabolism in vivo of Parathion (oxygen replaces the sulfur atom), Often used in biochemical investigations of serine hydrolases (structures of not alpha/beta hydrolases includes SGNH 1J00)
General
Type : Organophosphate, Insecticide, Derivative of Paraoxon, pNP
Chemical_Nomenclature : diethyl (4-nitrophenyl) phosphate
Canonical SMILES : CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI : InChI=1S\/C10H14NO6P\/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13\/h5-8H,3-4H2,1-2H3
InChIKey : WYMSBXTXOHUIGT-UHFFFAOYSA-N
Other name(s) : phosphoric acid diethyl 4-nitrophenyl ester || paraoxon-ethyl || Diethyl 4-nitrophenyl phosphate || diethyl p-nitrophenyl phosphate || phosphacol || E600 || ester25 || eticol || phosphakol || nintacol || miotisal A || solumlaucit || Mintacol || Fosfakol || Ethyl paraoxon || DNP || Diethyl paraoxon || paraoxon ethyl
MW : 275.21
Formula : C10H14NO6P
CAS_number : 311-45-5
PubChem : 9395
UniChem : WYMSBXTXOHUIGT-UHFFFAOYSA-N
Wikipedia : Paraoxon
Target
Structures : No structure
Families : BCHE, Dienelactone_hydrolase
References (14)
| Title : Structural and dynamic effects of paraoxon binding to human acetylcholinesterase by X-ray crystallography and inelastic neutron scattering - Gerlits_2022_Structure_30_1538 |
| Author(s) : Gerlits O , Fajer M , Cheng X , Blumenthal DK , Radic Z , Kovalevsky A |
| Ref : Structure , 30 :1538 , 2022 |
| Abstract : |
| PubMedSearch : Gerlits_2022_Structure_30_1538 |
| PubMedID: 36265484 |
| Gene_locus related to this paper: human-ACHE |
| Title : Ultrahigh-Throughput Directed Evolution of a Metal-Free alpha\/beta-Hydrolase with a Cys-His-Asp Triad into an Efficient Phosphotriesterase - Schnettler_2022_J.Am.Chem.Soc__ |
| Author(s) : Schnettler JD , Klein OJ , Kaminski TS , Colin PY , Hollfelder F |
| Ref : Journal of the American Chemical Society , : , 2022 |
| Abstract : |
| PubMedSearch : Schnettler_2022_J.Am.Chem.Soc__ |
| PubMedID: 36583539 |
| Gene_locus related to this paper: 9bact-KP212148 |
| Title : A Thermophilic Bacterial Esterase for Scavenging Nerve Agents: A Kinetic, Biophysical and Structural Study - Bzdrenga_2021_Molecules_26_657 |
| Author(s) : Bzdrenga J , Trenet E , Chantegreil F , Bernal K , Nachon F , Brazzolotto X |
| Ref : Molecules , 26 :657 , 2021 |
| Abstract : |
| PubMedSearch : Bzdrenga_2021_Molecules_26_657 |
| PubMedID: 33513869 |
| Gene_locus related to this paper: 9bact-TtEst2 |
| Title : Positron emission tomography evaluation of oxime countermeasures in live rats using the tracer O-(2-[(18) F]fluoroethyl)-O-(p-nitrophenyl)methylphosphonate [(18) F]-VXS - Hayes_2020_Ann.N.Y.Acad.Sci__ |
| Author(s) : Hayes TR , Blecha JE , Chao CK , Huynh TL , VanBrocklin HD , Zinn KR , Taylor P , Gerdes JM , Thompson CM |
| Ref : Annals of the New York Academy of Sciences , : , 2020 |
| Abstract : |
| PubMedSearch : Hayes_2020_Ann.N.Y.Acad.Sci__ |
| PubMedID: 32436233 |
| Title : A role for His-160 in peroxide inhibition of S. cerevisiae S-formylglutathione hydrolase: evidence for an oxidation sensitive motif - Legler_2012_Arch.Biochem.Biophys_528_7 |
| Author(s) : Legler PM , Leary DH , Hervey WJt , Millard CB |
| Ref : Archives of Biochemistry & Biophysics , 528 :7 , 2012 |
| Abstract : |
| PubMedSearch : Legler_2012_Arch.Biochem.Biophys_528_7 |
| PubMedID: 22906720 |
| Gene_locus related to this paper: yeast-yjg8 |
| Title : Crystal Structure of Proteus mirabilis Lipase, a Novel Lipase from the Proteus\/Psychrophilic Subfamily of Lipase Family I.1 - Korman_2012_PLoS.One_7_e52890 |
| Author(s) : Korman TP , Bowie JU |
| Ref : PLoS ONE , 7 :e52890 , 2012 |
| Abstract : |
| PubMedSearch : Korman_2012_PLoS.One_7_e52890 |
| PubMedID: 23300806 |
| Gene_locus related to this paper: promi-c2lfd0 |
| Title : Mutagenesis of organophosphorus hydrolase to enhance hydrolysis of the nerve agent VX - Gopal_2000_Biochem.Biophys.Res.Commun_279_516 |
| Author(s) : Gopal S , Rastogi V , Ashman W , Mulbry W |
| Ref : Biochemical & Biophysical Research Communications , 279 :516 , 2000 |
| Abstract : |
| PubMedSearch : Gopal_2000_Biochem.Biophys.Res.Commun_279_516 |
| PubMedID: 11118318 |
| Title : Organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase: synergy results in a somanase - Millard_1998_Biochemistry_37_237 |
| Author(s) : Millard CB , Lockridge O , Broomfield CA |
| Ref : Biochemistry , 37 :237 , 1998 |
| Abstract : |
| PubMedSearch : Millard_1998_Biochemistry_37_237 |
| PubMedID: 9425044 |
| Gene_locus related to this paper: human-BCHE |
| Title : A single amino acid substitution, Gly117His, confers phosphotriesterase (organophosphorus acid anhydride hydrolase) activity on human butyrylcholinesterase - Lockridge_1997_Biochemistry_36_786 |
| Author(s) : Lockridge O , Blong RM , Masson P , Froment MT , Millard CB , Broomfield CA |
| Ref : Biochemistry , 36 :786 , 1997 |
| Abstract : |
| PubMedSearch : Lockridge_1997_Biochemistry_36_786 |
| PubMedID: 9020776 |
| Title : Design and expression of organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase - Millard_1995_Biochemistry_34_15925 |
| Author(s) : Millard CB , Lockridge O , Broomfield CA |
| Ref : Biochemistry , 34 :15925 , 1995 |
| Abstract : |
| PubMedSearch : Millard_1995_Biochemistry_34_15925 |
| PubMedID: 8519749 |
| Title : The crystal and molecular structure of the Rhizomucor miehei triacylglyceride lipase at 1.9 A resolution - Derewenda_1992_J.Mol.Biol_227_818 |
| Author(s) : Derewenda ZS , Derewenda U , Dodson GG |
| Ref : Journal of Molecular Biology , 227 :818 , 1992 |
| Abstract : |
| PubMedSearch : Derewenda_1992_J.Mol.Biol_227_818 |
| PubMedID: 1404390 |
| Gene_locus related to this paper: rhimi-lipas |
| Title : Short-term effects of paraoxon and atropine on schedule-controlled behavior in rats - Chambers_1989_Neurotoxicol.Teratol_11_427 |
| Author(s) : Chambers JE , Chambers HW |
| Ref : Neurotoxicology & Teratology , 11 :427 , 1989 |
| Abstract : |
| PubMedSearch : Chambers_1989_Neurotoxicol.Teratol_11_427 |
| PubMedID: 2593981 |
| Title : Mintacol (diethyl-p-nitrophenylphosphate) (Paraoxon) - |
| Author(s) : Augustinsson KB |
| Ref : Sven Farm Tidskr , 57 :261 , 1953 |
| PubMedID: 13077191 |
| Title : Enzyme studies with diethyl-p-nitrophenylphosphate (mintacol) - |
| Author(s) : Augustinsson KB |
| Ref : Acta Pharmacologica et Toxicologica (Copenh) , 9 :245 , 1953 |
| PubMedID: 13123943 |