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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:45 UTC
HMDB IDHMDB01460
Secondary Accession NumbersNone
Metabolite Identification
Common NameDiethylthiophosphate
DescriptionDiethylthiophosphate is the most frequent metabolite of organophosphorus (OP) found in urine (PMID 15050412 ). Organophosphorus compounds are widely used as pesticides because of easy degradation in the environment. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase (PMID 11991535 ). Chronic exposure to POs has neurological sequelae as well (PMID 8179040 ) and data suggests that OP exposure alters sperm chromatin condensation (PMID 15050412 ).
Structure
Thumb
Synonyms
ValueSource
DETPChEBI
Diethylthiophosphoric acidChEBI
Diethoxy-hydroxy-sulphanylidene-$l^{5}-phosphaneGenerator
DiethylthiophosphateGenerator
DiethylthiophosphorateHMDB
O,O-Diethyl phosphorothionateHMDB
Chemical FormulaC4H11O3PS
Average Molecular Weight170.167
Monoisotopic Molecular Weight170.01665142
IUPAC Namediethoxy(sulfanylidene)phosphinous acid
Traditional NameDETP
CAS Registry Number5871-17-0
SMILES
CCOP(O)(=S)OCC
InChI Identifier
InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)
InChI KeyInChIKey=PKUWKAXTAVNIJR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thiophosphate diesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly two R-groups are organyl groups.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganothiophosphorus compounds
Sub ClassOrganic thiophosphoric acids and derivatives
Direct ParentThiophosphate diesters
Alternative Parents
Substituents
  • Thiophosphate diester
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility6.06 mg/mLALOGPS
logP1.22ALOGPS
logP1.34ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.1 m3·mol-1ChemAxon
Polarizability15.97 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014l-0900000000-4d60832ad8293c6ffadaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kb-9400000000-4edb8f3e7564089a88f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000t-9000000000-992c7d4759e33fca928dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-c8423ea1caef16b9a74eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0005-7900000000-eba2d541218620747842View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-ae31cece541b8a3affddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-1772cdb892c30908258dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-0a0320defdca903d57ddView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.000297 (0.000223-0.000397) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.000393 (0.000313-0.000493) 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022638
KNApSAcK IDNot Available
Chemspider ID635
KEGG Compound IDC06607
BioCyc IDDIETHYLTHIOPHOSPHATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01460
Metagene LinkHMDB01460
METLIN ID6256
PubChem Compound655
PDB IDDPJ
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Heudorf U, Angerer J: Metabolites of organophosphorous insecticides in urine specimens from inhabitants of a residential area. Environ Res. 2001 May;86(1):80-7. [11386745 ]
  2. Wagner SL, Orwick DL: Chronic organophosphate exposure associated with transient hypertonia in an infant. Pediatrics. 1994 Jul;94(1):94-7. [8008546 ]
  3. Aprea C, Sciarra G, Orsi D, Boccalon P, Sartorelli P, Sartorelli E: Urinary excretion of alkylphosphates in the general population (Italy). Sci Total Environ. 1996 Jan 5;177(1-3):37-41. [8584918 ]
  4. Lin WC, Kuei CH, Wu HC, Yang CC, Chang HY: Method for the determination of dialkyl phosphates in urine by strong anion exchange disk extraction and in-vial derivatization. J Anal Toxicol. 2002 Apr;26(3):176-80. [11991535 ]
  5. Sanchez-Pena LC, Reyes BE, Lopez-Carrillo L, Recio R, Moran-Martinez J, Cebrian ME, Quintanilla-Vega B: Organophosphorous pesticide exposure alters sperm chromatin structure in Mexican agricultural workers. Toxicol Appl Pharmacol. 2004 Apr 1;196(1):108-13. [15050412 ]
  6. Steenland K, Jenkins B, Ames RG, O'Malley M, Chrislip D, Russo J: Chronic neurological sequelae to organophosphate pesticide poisoning. Am J Public Health. 1994 May;84(5):731-6. [8179040 ]

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
Parathion + Water → Diethylthiophosphate + 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
Parathion + Water → Diethylthiophosphate + 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
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails