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Human Metabolome Database Version 3.5

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Showing metabocard for Diethylphosphate (HMDB12209)

Record Information
Version 3.5
Creation Date 2009-04-06 10:21:03 -0600
Update Date 2013-02-08 17:28:30 -0700
HMDB ID HMDB12209
Secondary Accession Numbers None
Metabolite Identification
Common Name Diethylphosphate
Description 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. (PMID: 17590257 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. DEP
  2. Di-Ethyl phosphate
  3. Diethyl acid phosphate
  4. Diethyl hydrogen phosphate
  5. Diethyl phosphate
  6. Diethyl phosphoric acid
  7. Diethylphosphoric acid
  8. DPF
  9. Ethyl phosphate
  10. O,O-Diethyl hydrogen phosphate
  11. O,O-Diethyl phosphate
  12. O,O-Diethylphosphoric acid
  13. Phosphoric acid diethyl ester
Chemical Formula C4H11O4P
Average Molecular Weight 154.1015
Monoisotopic Molecular Weight 154.039495352
IUPAC Name diethoxyphosphinic acid
Traditional IUPAC Name diethyl phosphate
CAS Registry Number 598-02-7
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 Key UCQFCFPECQILOL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organophosphorus Compounds
Class Organic Phosphoric Acids and Derivatives
Sub Class Organophosphate Esters
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Organic Hypophosphite
  • Organic Phosphite
Direct Parent Organophosphate Esters
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 44.1 g/L ALOGPS
LogP 0.41 ALOGPS
LogP 0.45 ChemAxon
LogS -0.54 ALOGPS
pKa (strongest acidic) 1.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 55.76 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 33.11 ChemAxon
Polarizability 13.86 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.00452(0.00268-0.00710) umol/mmol creatinine Not Available Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.00323(0.00237-0.00429) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028854
KNApSAcK ID Not Available
Chemspider ID 634 Link_out
KEGG Compound ID C06608 Link_out
BioCyc ID DIETHYLPHOSPHATE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12209 Link_out
Metagene Link HMDB12209 Link_out
METLIN ID Not Available
PubChem Compound 654 Link_out
PDB ID DPF Link_out
ChEBI ID 38598 Link_out
References
Synthesis Reference Not 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 Link_out