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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:43 UTC

HMDB ID

HMDB0001460

Secondary Accession Numbers

HMDB01460

Metabolite Identification

Common Name

Diethylthiophosphate

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 )

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

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.512	31661259
DarkChem	[M-H]-	130.6	31661259
AllCCS	[M+H]+	133.305	32859911
AllCCS	[M-H]-	138.52	32859911
DeepCCS	[M+H]+	131.046	30932474
DeepCCS	[M-H]-	128.964	30932474
DeepCCS	[M-2H]-	164.824	30932474
DeepCCS	[M+Na]+	139.538	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	141.4	32859911
AllCCS	[M+HCOO]-	144.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.86 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4021 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1470.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	223.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	423.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	510.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	857.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	323.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1057.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	411.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	419.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	92.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethylthiophosphate	CCOP(O)(=S)OCC	1850.3	Standard polar	33892256
Diethylthiophosphate	CCOP(O)(=S)OCC	1127.3	Standard non polar	33892256
Diethylthiophosphate	CCOP(O)(=S)OCC	1155.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diethylthiophosphate,1TMS,isomer #1	CCOP(=S)(OCC)O[Si](C)(C)C	1221.9	Semi standard non polar	33892256
Diethylthiophosphate,1TMS,isomer #1	CCOP(=S)(OCC)O[Si](C)(C)C	1241.4	Standard non polar	33892256
Diethylthiophosphate,1TMS,isomer #1	CCOP(=S)(OCC)O[Si](C)(C)C	1528.3	Standard polar	33892256
Diethylthiophosphate,1TBDMS,isomer #1	CCOP(=S)(OCC)O[Si](C)(C)C(C)(C)C	1440.3	Semi standard non polar	33892256
Diethylthiophosphate,1TBDMS,isomer #1	CCOP(=S)(OCC)O[Si](C)(C)C(C)(C)C	1462.4	Standard non polar	33892256
Diethylthiophosphate,1TBDMS,isomer #1	CCOP(=S)(OCC)O[Si](C)(C)C(C)(C)C	1676.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diethylthiophosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01vo-4900000000-eca7564ce2ac94c32b49	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethylthiophosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014l-0900000000-4d60832ad8293c6ffada	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00kb-9400000000-4edb8f3e7564089a88f3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-000t-9000000000-992c7d4759e33fca928d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0900000000-c8423ea1caef16b9a74e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0005-7900000000-eba2d541218620747842	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0002-9000000000-ae31cece541b8a3affdd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0002-9000000000-1772cdb892c30908258d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0002-9000000000-0a0320defdca903d57dd	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-c8423ea1caef16b9a74e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ , negative-QTOF	splash10-0005-7900000000-eba2d541218620747842	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-ae31cece541b8a3affdd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-1772cdb892c30908258d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diethylthiophosphate LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-0a0320defdca903d57dd	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 10V, Positive-QTOF	splash10-00dl-0900000000-5044901daaf5712fa9ec	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 20V, Positive-QTOF	splash10-03kc-1900000000-19204dbb8b74001b3fd2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 40V, Positive-QTOF	splash10-004i-7900000000-f90194c8eeb269ef0a00	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 10V, Negative-QTOF	splash10-00kf-1900000000-e860be0b6c7be56a72f3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 20V, Negative-QTOF	splash10-0006-9700000000-8cf600a8319cb75ee542	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 40V, Negative-QTOF	splash10-03dm-9700000000-f384fa244ef2411c8f54	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 10V, Negative-QTOF	splash10-0006-9500000000-ff238d3cf2c783ff8b25	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 20V, Negative-QTOF	splash10-0006-9000000000-7ed10e2dbf916ab00db8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 40V, Negative-QTOF	splash10-0006-9000000000-7ed10e2dbf916ab00db8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 10V, Positive-QTOF	splash10-03dl-0900000000-c7095c703601052b840f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 20V, Positive-QTOF	splash10-03di-1900000000-735f3f957e502e52eef3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylthiophosphate 40V, Positive-QTOF	splash10-0002-9000000000-b9b7ee005a9da13c1a9d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.000297 (0.000223-0.000397) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.000393 (0.000313-0.000493) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB07674

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022638

KNApSAcK ID

Not Available

Chemspider ID

635

KEGG Compound ID

C06607

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6256

PubChem Compound

655

PDB ID

Not Available

ChEBI ID

28006

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
Wagner SL, Orwick DL: Chronic organophosphate exposure associated with transient hypertonia in an infant. Pediatrics. 1994 Jul;94(1):94-7. [PubMed:8008546 ]
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 ]
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 ]
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 ]
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

Enzyme Details

1. Serum paraoxonase/lactonase 3

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-Nitrophenol	details

Enzyme Details

2. Serum paraoxonase/arylesterase 1

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-Nitrophenol	details

Enzyme Details

3. Serum paraoxonase/arylesterase 2

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-Nitrophenol	details

Showing metabocard for Diethylthiophosphate (HMDB0001460)

MOL for HMDB0001460 (Diethylthiophosphate)

3D MOL for HMDB0001460 (Diethylthiophosphate)

3D SDF for HMDB0001460 (Diethylthiophosphate)

3D-SDF for HMDB0001460 (Diethylthiophosphate)

PDB for HMDB0001460 (Diethylthiophosphate)

3D PDB for HMDB0001460 (Diethylthiophosphate)

SMILES for HMDB0001460 (Diethylthiophosphate)

INCHI for HMDB0001460 (Diethylthiophosphate)

Structure for HMDB0001460 (Diethylthiophosphate)

3D Structure for HMDB0001460 (Diethylthiophosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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