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Record Information
Version3.6
Creation Date2009-07-25 00:12:03 UTC
Update Date2013-02-09 00:29:42 UTC
HMDB IDHMDB13035
Secondary Accession NumbersNone
Metabolite Identification
Common NameParaoxon
DescriptionParaoxon is an acetylcholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an opthamological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. It is easily absorbed through skin, and was used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast.
Structure
Thumb
Synonyms
  1. O,O-Diethyl-O-p-nitrophenylphosphoric acid
Chemical FormulaC10H14NO6P
Average Molecular Weight275.195
Monoisotopic Molecular Weight275.055873697
IUPAC Namediethyl 4-nitrophenyl phosphate
Traditional Nameparaoxon
CAS Registry Number311-45-5
SMILES
CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
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
InChI KeyWYMSBXTXOHUIGT-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassNitrophenols and Derivatives
Other Descriptors
  • Nitrobenzenes
  • Organic Compounds
  • a small molecule(Cyc)
  • aryl dialkyl phosphate(ChEBI)
  • organophosphate insecticide(ChEBI)
Substituents
  • Nitro Compound
  • Organic Hypophosphite
  • Organic Oxoazanium
  • Organic Phosphite
  • Phosphoric Acid Ester
Direct ParentNitrophenols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.64 mg/mL at 20 °CNot Available
LogP1.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility1.44ALOGPS
logP2.05ALOGPS
logP2.43ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area90.58 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity64.7 m3·mol-1ChemAxon
Polarizability24.97 Å3ChemAxon
Spectra
SpectraMS
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029261
KNApSAcK IDNot Available
Chemspider ID9026
KEGG Compound IDC06606
BioCyc IDPARAOXON
BiGG IDNot Available
Wikipedia LinkParaoxon
NuGOwiki LinkHMDB13035
Metagene LinkHMDB13035
METLIN IDNot Available
PubChem Compound9395
PDB IDNot Available
ChEBI ID27827
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Reactions
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Reactions
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Reactions
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails