ChemFOnt: Showing chemical card for Diethylthiophosphate (CFc000001128)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:41 UTC

Chemfont ID

CFc000001128

Molecule Identification

Common Name

Diethylthiophosphate

Definition

Diethylthiophosphate, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DETP	ChEBI
Diethylthiophosphoric acid	ChEBI
Diethylthiophosphorate	HMDB
O,O-Diethyl phosphorothionate	HMDB
O,O-Diethyl phosphorothionate, ammonium salt	MeSH, HMDB
O,O-Diethyl phosphorothionate, sodium salt	MeSH, HMDB
O,O-Diethyl phosphorothioate	MeSH, HMDB
O,O-Diethyl phosphorothionate, potassium salt	MeSH, HMDB
Diethylthiophosphate	Generator
O,O-Diethyl hydrogen thiophosphoric acid	Generator, HMDB

Chemical Formula

C₄H₁₁O₃PS

Average Molecular Weight

170.167

Monoisotopic Molecular Weight

170.01665142

IUPAC Name

diethoxy(sulfanylidene)phosphinous acid

Traditional Name

DETP

CAS Registry Number

5871-17-0

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 Key

PKUWKAXTAVNIJR-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic thiophosphoric acids and derivatives

Sub Class

Thiophosphoric acid esters

Direct Parent

Thiophosphate diesters

Alternative Parents

Substituents

Thiophosphate diester
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic thiophosphate (CHEBI:28006 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Cytoplasm (HMDB: HMDB0001460)
Extracellular (HMDB: HMDB0001460)

Source

Exogenous

Exogenous (HMDB: HMDB0001460)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001460)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001460)

Biological role

Human xenobiotic metabolite (HMDB: HMDB0001460)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.06 g/L	ALOGPS
logP	1.22	ALOGPS
logP	1.34	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.1 m³·mol⁻¹	ChemAxon
Polarizability	15.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon