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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:43 UTC
HMDB IDHMDB0001460
Secondary Accession Numbers
  • HMDB01460
Metabolite Identification
Common NameDiethylthiophosphate
DescriptionDiethylthiophosphate, also known as DETP, 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. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Diethylthiophosphate is a potentially toxic compound. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase Chronic exposure to POs has neurological sequelae as well and data suggests that OP exposure alters sperm chromatin condensation (A3181, A3182, A3183, A3181). Chronic exposure to POs has neurological sequelae as well (PMID 8179040 ) and data suggests that OP exposure alters sperm chromatin condensation (PMID 15050412 ). PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase (PMID 11991535 ).
Structure
Thumb
Synonyms
ValueSource
DETPChEBI
Diethylthiophosphoric acidChEBI
DiethylthiophosphorateHMDB
O,O-Diethyl phosphorothionateHMDB
O,O-Diethyl phosphorothionate, ammonium saltMeSH, HMDB
O,O-Diethyl phosphorothionate, sodium saltMeSH, HMDB
O,O-Diethyl phosphorothioateMeSH, HMDB
O,O-Diethyl phosphorothionate, potassium saltMeSH, HMDB
DiethylthiophosphateGenerator
O,O-Diethyl hydrogen thiophosphoric acidGenerator, HMDB
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 KeyPKUWKAXTAVNIJR-UHFFFAOYSA-N
Chemical Taxonomy
Description 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 ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentThiophosphate diesters
Alternative Parents
Substituents
  • Thiophosphate diester
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
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 IDDB07674
Phenol Explorer Compound IDNot Available
FooDB IDFDB022638
KNApSAcK IDNot Available
Chemspider ID635
KEGG Compound IDC06607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6256
PubChem Compound655
PDB IDNot Available
ChEBI ID28006
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed:11386745 ]
  2. Wagner SL, Orwick DL: Chronic organophosphate exposure associated with transient hypertonia in an infant. Pediatrics. 1994 Jul;94(1):94-7. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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