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Substrate Report for: 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
IUPHAR|
Wikipedia|Paraoxon

Target
Families | Paraoxon ligand of proteins in family: BCHE

References:
Search PubMed for references concerning: Paraoxon

5 more
    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 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 : PubMed

            

    Title: A single amino acid substitution, Gly117His, confers phosphotriesterase (organophosphorus acid anhydride hydrolase) activity on human butyrylcholinesterase
    Lockridge O, Blong RM, Masson P, Froment MT, Millard CB, Broomfield CA
    Ref: Biochemistry, 36:786, 1997 : PubMed

            

    Title: Design and expression of organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase
    Millard CB, Lockridge O, Broomfield CA
    Ref: Biochemistry, 34:15925, 1995 : PubMed

            


human-BCHE
MutationKmKcatConditionPaper
G117H 70 uM 0.75/min T25C IS 100 mM phosphate pH7 Lockridge_1997_Biochemistry_36_786