Human Metabolome Database Version 3.5

Showing metabocard for Paraoxon (HMDB13035)

Record Information
Version 3.5
Creation Date 2009-07-24 18:12:03 -0600
Update Date 2013-02-08 17:29:42 -0700
HMDB ID HMDB13035
Secondary Accession Numbers None
Metabolite Identification
Common Name Paraoxon
Description Paraoxon 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
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Display: 2D Structure | 3D Structure
Synonyms
  1. O,O-Diethyl-O-p-nitrophenylphosphoric acid
Chemical Formula C10H14NO6P
Average Molecular Weight 275.195
Monoisotopic Molecular Weight 275.055873697
IUPAC Name diethyl 4-nitrophenyl phosphate
Traditional IUPAC Name paraoxon
CAS Registry Number 311-45-5
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 Key WYMSBXTXOHUIGT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Nitrophenols 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 Parent Nitrophenols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 300 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.64 mg/mL at 20 °C Not Available
LogP 1.98 SANGSTER (1994)
Predicted Properties
Property Value Source
LogP 2.05 ALOGPS
LogP 2.43 ChemAxon
LogS -2.28 ALOGPS
pKa (strongest basic) -9.2 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 90.58 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 64.7 ChemAxon
Polarizability 24.97 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029261
KNApSAcK ID Not Available
Chemspider ID 9026 Link_out
KEGG Compound ID C06606 Link_out
BioCyc ID PARAOXON Link_out
BiGG ID Not Available
Wikipedia Link Paraoxon Link_out
NuGOwiki Link HMDB13035 Link_out
Metagene Link HMDB13035 Link_out
METLIN ID Not Available
PubChem Compound 9395 Link_out
PDB ID Not Available
ChEBI ID 27827 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Serum paraoxonase/lactonase 3
Reactions:
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenol details
Gene Name: PON3
Uniprot ID: Q15166 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum paraoxonase/arylesterase 1
Reactions:
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenol details
Gene Name: PON1
Uniprot ID: P27169 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum paraoxonase/arylesterase 2
Reactions:
Paraoxon + Water unknown Diethylphosphate + 4-Nitrophenol details
Gene Name: PON2
Uniprot ID: Q15165 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA