Tmic
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.
Record Information
Version2.0
Creation Date2014-08-29 04:48:13 UTC
Update Date2014-12-24 20:26:35 UTC
Accession NumberT3D3969
Identification
Common NameDiethylphosphate
ClassSmall Molecule
DescriptionDiethylphosphate is product of metabolism and of environmental degradation of Chlorpyrifos (CPF; a commonly used diethylphosphorothionate organophosphorus (OP) insecticide) and are routinely measured in urine as biomarkers of exposure. (1).
Compound Type
  • Ester
  • Food Toxin
  • Insecticide
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
DEP
Di-Ethyl phosphate
Diethyl acid phosphate
Diethyl hydrogen phosphate
Diethyl phosphate
Diethyl phosphoric acid
Diethylphosphic acid
Diethylphosphoric acid
DPF
Ethyl phosphate
O,O-Diethyl hydrogen phosphate
O,O-Diethyl phosphate
O,O-Diethylphosphoric acid
Phosphoric acid diethyl ester
Chemical FormulaC4H11O4P
Average Molecular Mass154.102 g/mol
Monoisotopic Mass154.039 g/mol
CAS Registry Number598-02-7
IUPAC Namediethoxyphosphinic acid
Traditional Namediethyl phosphoric acid
SMILESCCOP(O)(=O)OCC
InChI IdentifierInChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)
InChI KeyInChIKey=UCQFCFPECQILOL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentDialkyl phosphates
Alternative Parents
Substituents
  • Dialkyl phosphate
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility44.1 g/LALOGPS
logP0.41ALOGPS
logP0.45ChemAxon
logS-0.54ALOGPS
pKa (Strongest Acidic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.11 m³·mol⁻¹ChemAxon
Polarizability13.86 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-4900000000-294a52a603382bfaa543View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-66ba682d35b3d8da27cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9800000000-a7c39957412f58baa3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a80db507a9f92dc8e8dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-74ebac8f0ccd57c6cf36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-852694d793f0cdedbe66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-0996f2acaca4f0378a8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-7ad57dadba1dfa80fb5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9300000000-116e8a80cf2a89f620b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-91ccdf926ebb73f9befcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9700000000-6f4a1df48257e4a70300View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-040631eee3a1988c9f1aView in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityS-Ethylisothiouronium diethylphosphate is a specific inhibitor of inducible NO synthase on hepatic NO production level. S-Ethylisothiouronium diethylphosphate affects systemic hemodynamic indices in the following way: the peripheral vascular resistance increases, the stroke volume and central blood volume increase, and the work of the left ventricle improves. (Wikipedia)
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB12209
PubChem Compound ID654
ChEMBL IDNot Available
ChemSpider ID634
KEGG IDC06608
UniProt IDNot Available
OMIM ID
ChEBI ID38598
BioCyc IDDIETHYLPHOSPHATE
CTD IDNot Available
Stitch IDNot Available
PDB IDDPF
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3969.pdf
General References
  1. Timchalk C, Busby A, Campbell JA, Needham LL, Barr DB: Comparative pharmacokinetics of the organophosphorus insecticide chlorpyrifos and its major metabolites diethylphosphate, diethylthiophosphate and 3,5,6-trichloro-2-pyridinol in the rat. Toxicology. 2007 Jul 31;237(1-3):145-57. Epub 2007 May 18. [17590257 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Tetrahydrobiopterin binding
Specific Function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular Weight:
131116.3 Da