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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-04-06 16:21:03 UTC
Update Date2020-02-26 21:37:07 UTC
HMDB IDHMDB0012209
Secondary Accession Numbers
  • HMDB12209
Metabolite Identification
Common NameDiethylphosphate
DescriptionDiethylphosphate, also known as DEP or DPF, 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. Diethylphosphate is a moderately acidic compound (based on its pKa). Diethylphosphate exists in all living organisms, ranging from bacteria to humans. Diethylphosphate is a potentially toxic compound. S-Ethylisothiouronium diethylphosphate is a specific inhibitor of inducible NO synthase on hepatic NO production level. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Diethylphosphate 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. 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. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. Oxidation of organophosphorus pesticides may result in moderately toxic products. Demethylation and glucuronidation may also occur.
Structure
Data?1582753027
Synonyms
ValueSource
Diethylphosphoric acidChEBI
O,O-Diethylphosphoric acidChEBI
O,O-DiethylphosphateGenerator
DEPHMDB
Di-ethyl phosphateHMDB
Diethyl acid phosphateHMDB
Diethyl hydrogen phosphateHMDB
Diethyl phosphateHMDB
Diethyl phosphoric acidHMDB
DPFHMDB
Ethyl phosphateHMDB
O,O-Diethyl hydrogen phosphateHMDB
O,O-Diethyl phosphateHMDB
Phosphoric acid diethyl esterHMDB
Diethyl phosphate, sodium saltHMDB
Diethyl phosphate, chromium (+3) saltHMDB
DiethylphosphateChEBI
Diethyl hydrogen phosphoric acidGenerator
Chemical FormulaC4H11O4P
Average Molecular Weight154.1015
Monoisotopic Molecular Weight154.039495352
IUPAC Namediethoxyphosphinic acid
Traditional Namediethyl phosphoric acid
CAS Registry Number598-02-7
SMILES
CCOP(O)(=O)OCC
InChI Identifier
InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)
InChI KeyUCQFCFPECQILOL-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
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-4900000000-294a52a603382bfaa543Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-66ba682d35b3d8da27cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9800000000-a7c39957412f58baa3dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a80db507a9f92dc8e8dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-74ebac8f0ccd57c6cf36Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-852694d793f0cdedbe66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-0996f2acaca4f0378a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-7ad57dadba1dfa80fb5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9300000000-116e8a80cf2a89f620b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-91ccdf926ebb73f9befcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9700000000-6f4a1df48257e4a70300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-040631eee3a1988c9f1aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00452(0.00268-0.00710) umol/mmol creatinineNot AvailableBothNormal
    • Report on Human B...
details
UrineDetected and Quantified0.00323(0.00237-0.00429) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Report on Human B...
details
UrineDetected and Quantified0.000729 (0.000421-0.000998) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.00105 (0.000638-0.00173) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028854
KNApSAcK IDNot Available
Chemspider ID634
KEGG Compound IDC06608
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound654
PDB IDNot Available
ChEBI ID27708
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:17590257 ]

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