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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:03 UTC
Update Date2017-12-07 02:38:56 UTC
HMDB IDHMDB0013035
Secondary Accession Numbers
  • HMDB13035
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
ValueSource
Diethyl P-nitrophenyl phosphateChEBI
Diethyl paraoxonChEBI
Ethyl paraoxonChEBI
O,O-Diethyl O-P-nitrophenyl phosphateChEBI
P-Nitrophenyl diethyl phosphateChEBI
PhosphacolChEBI
Phosphoric acid diethyl 4-nitrophenyl esterChEBI
Diethyl P-nitrophenyl phosphoric acidGenerator
O,O-Diethyl O-P-nitrophenyl phosphoric acidGenerator
P-Nitrophenyl diethyl phosphoric acidGenerator
Phosphate diethyl 4-nitrophenyl esterGenerator
O,O-Diethyl-O-P-nitrophenylphosphoric acidHMDB
Diethyl P nitrophenyl phosphateMeSH
Phosphate, diethyl-P-nitrophenylMeSH
Diethyl-P-nitrophenyl phosphateMeSH
FosfakolMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Phenoxy compound
  • Nitroaromatic compound
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Psychiatric disorders:

    Gastrointestinal disorders:

    Nervous system disorders:

    General disorders and administration site conditions:

    Musculoskeletal and connective tissue disorders:

    Metabolism and nutrition disorders:

    Vascular disorders:

  Observation:

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 Solubility1.44 g/LALOGPS
logP2.05ALOGPS
logP2.43ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area90.58 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity64.7 m³·mol⁻¹ChemAxon
Polarizability24.97 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4m-4910000000-9e80686be84777f12897View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-1490000000-49af8e137482487310cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1290000000-6438528767f006512903View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0090000000-775108cc711fdc42be34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-7900000000-0b2814cb44352b4577e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0190000000-cfd94300e89fae9a0128View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1490000000-609dc6a1aa30dd298795View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-2940000000-ab53630a454ec7edd2b2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-054k-9840000000-ed91d6d60187378e30e6View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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