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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:14 UTC
HMDB IDHMDB0001355
Secondary Accession Numbers
  • HMDB01355
Metabolite Identification
Common NameParathion
DescriptionParathion, also known as diethyl parathion or thiophos, belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group. Parathion is an extremely weak basic (essentially neutral) compound (based on its pKa). Parathion exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Parathion has been detected, but not quantified in, asparagus. This could make parathion a potential biomarker for the consumption of these foods. "E" stands for Entwicklungsnummer (German for "development number"). It was originally developed by IG Farben in the 1940s. Parathion is a potentially toxic compound. It is commonly distributed as a brown liquid that smells of rotting eggs or garlic.
Structure
Data?1582752194
Synonyms
ValueSource
Diethyl p-nitrophenyl thiophosphateChEBI
Diethyl parathionChEBI
DNTPChEBI
Ethyl parathionChEBI
O,O-Diethyl O-(4-nitrophenyl) thiophosphateChEBI
O,O-Diethyl O-(p-nitrophenyl) thiophosphateChEBI
O,O-Diethyl O-p-nitrophenyl phosphorothioateChEBI
Phosphorothioic acid, O,O-diethyl O-(4-nitrophenyl) esterChEBI
ThiophosChEBI
Diethyl p-nitrophenyl thiophosphoric acidGenerator
O,O-Diethyl O-(4-nitrophenyl) thiophosphoric acidGenerator
O,O-Diethyl O-(p-nitrophenyl) thiophosphoric acidGenerator
O,O-Diethyl O-p-nitrophenyl phosphorothioic acidGenerator
Phosphorothioate, O,O-diethyl O-(4-nitrophenyl) esterGenerator
AlkronHMDB
AlleronHMDB
American cyanamid 3422HMDB
AphamiteHMDB
Aqua 9-parathionHMDB
AraloHMDB
BladanHMDB
BladenHMDB
CorothionHMDB
CorthioneHMDB
DanthionHMDB
Deoxynucleoside 5'-triphosphateHMDB
Diethyl 4-nitrophenyl phosphorothionateHMDB
Diethyl O-p-nitrophenyl phosphorothioateHMDB
Diethyl O-p-nitrophenyl phosphorothioic acidHMDB
Diethyl p-nitrophenyl thionophosphateHMDB
Diethyl para-nitrophenol thiophosphateHMDB
Diethyl-p-nitrophenyl monothiophosphateHMDB
DiethylparathionHMDB
Drexel parathion 8EHMDB
DurathionHMDB
EcatoxHMDB
EthlonHMDB
Ethyl parathion (O,O-diethyl-O-p-nitrophenylthiophosphate)HMDB
EtilonHMDB
FoliclalHMDB
FolidolHMDB
Folidol e e 605HMDB
Folidol e605HMDB
Folidol oilHMDB
FosfermoHMDB
FosfernoHMDB
Fosferno 50HMDB
FosfexHMDB
FosfiveHMDB
FosovaHMDB
FosternHMDB
FostoxHMDB
GearphosHMDB
GenithionHMDB
KolphosHMDB
KypthionHMDB
Lethalaire g-54HMDB
LirothionHMDB
MurfosHMDB
NiranHMDB
NitrostygmineHMDB
Niuif-100HMDB
NourithionHMDB
O,O-Diethyl-O-(p-nitrophenyl)thionophosphateHMDB
Oleofos 20HMDB
OleoparapheneHMDB
OleoparathionHMDB
OMS 19HMDB
OrthophosHMDB
p-Nitrophenol O-ester with O,O-diethylphosphorothioateHMDB
p-Nitrophenol O-ester with O,O-diethylphosphorothioic acidHMDB
PACHMDB
PacolHMDB
PanthionHMDB
ParadustHMDB
ParamarHMDB
Paramar 50HMDB
ParaphosHMDB
ParatheneHMDB
Parathion-eHMDB
ParawetHMDB
ParthionHMDB
Penncap eHMDB
Pestox plusHMDB
PethionHMDB
PhoskilHMDB
PhosphemolHMDB
PhosphenolHMDB
PhosphorothioateHMDB
Phosphorothioic acidHMDB
Phosphorothioic acid O,O-diethyl-O-(4-nitrophenyl) esterHMDB
PhosphostigmineHMDB
RhodiasolHMDB
RhodiatoxHMDB
RhodiatroxHMDB
SelephosHMDB
Sixty-three special e.cHMDB
SoprathionHMDB
Stabilized ethyl parathionHMDB
StathionHMDB
StrathionHMDB
SulfosHMDB
Super rodiatoxHMDB
T-47HMDB
ThiomexHMDB
Thionspray no.84HMDB
Thiophos 3422HMDB
TiofosHMDB
VapophosHMDB
ViranHMDB
VitrexHMDB
ThiofosHMDB
Parathion, ethylHMDB
Chemical FormulaC10H14NO5PS
Average Molecular Weight291.261
Monoisotopic Molecular Weight291.033029765
IUPAC NameO,O-diethyl O-4-nitrophenyl phosphorothioate
Traditional Namebladen
CAS Registry Number56-38-2
SMILES
CCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3
InChI KeyLCCNCVORNKJIRZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPhenyl thiophosphates
Alternative Parents
Substituents
  • Phenyl thiophosphate
  • Nitrobenzene
  • Phenoxy compound
  • Nitroaromatic compound
  • Thiophosphate triester
  • Monocyclic benzene moiety
  • Benzenoid
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point6.1 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.011 mg/mLNot Available
LogP3.83Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP10(3.76) g/LALOGPS
logP10(3.32) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area70.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity71.68 m³·mol⁻¹ChemAxon
Polarizability26.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.66331661259
DarkChem[M-H]-163.00931661259
AllCCS[M+H]+159.67632859911
AllCCS[M-H]-157.19932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ParathionCCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O3037.3Standard polar33892256
ParathionCCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O1967.7Standard non polar33892256
ParathionCCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O1957.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Parathion GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-1390000000-256208006a2b1561db1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Parathion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a74-8940000000-4bf55c77de23f747eb802014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion LC-ESI-QFT , positive-QTOFsplash10-01p9-0090000000-fe8742077ddcdaa842802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion LC-ESI-QFT , positive-QTOFsplash10-000i-0190000000-af44a385ea22b63268192017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion LC-ESI-QFT , positive-QTOFsplash10-000l-1940000000-218556da13b43e16e2bf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion LC-ESI-QFT , positive-QTOFsplash10-01vo-2910000000-4a40f241595d8b5628d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion LC-ESI-QFT , positive-QTOFsplash10-01vo-4900000000-c58ec980fa6b4210133c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion LC-ESI-QFT , positive-QTOFsplash10-01ox-6900000000-80ce5f0f59ebc4a626812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion 90V, Positive-QTOFsplash10-01ox-6900000000-0ae225ae5aa0b11161e32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion 15V, Positive-QTOFsplash10-01p9-0090000000-699baba652581ceae2be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion 45V, Positive-QTOFsplash10-000l-1940000000-15d927af1afee2c090282021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion 30V, Positive-QTOFsplash10-000i-0190000000-13506519f0e449b526782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion 60V, Positive-QTOFsplash10-01vo-2910000000-e81debcb63112f1a81872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Parathion 75V, Positive-QTOFsplash10-01vo-4900000000-697208a779d2fefe32fd2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 10V, Positive-QTOFsplash10-0006-1090000000-e7daa1435a3c8202b8dc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 20V, Positive-QTOFsplash10-00lr-1090000000-0ee220c0c9ec67d726bb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 40V, Positive-QTOFsplash10-004j-9720000000-be163305078ac89a76812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 10V, Negative-QTOFsplash10-0006-0390000000-3cdf27289e65564f20282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 20V, Negative-QTOFsplash10-0006-0490000000-9b32c86de4c27c33c4052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 40V, Negative-QTOFsplash10-000f-1940000000-6f5772e73d0e7958d6cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 10V, Positive-QTOFsplash10-0006-0090000000-9585d70a69dd82c677f02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 20V, Positive-QTOFsplash10-01pc-0090000000-7f509a774ae9d3a5ac842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 40V, Positive-QTOFsplash10-0udi-9340000000-b44b4f76ff61f463d2db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 10V, Negative-QTOFsplash10-0006-0090000000-f2d3ba63a2de010595cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 20V, Negative-QTOFsplash10-03di-0290000000-b84c6ef99ca6164924992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parathion 40V, Negative-QTOFsplash10-006t-7910000000-fc58d956a883b5d8b5ca2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0687-68.721 uMAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022574
KNApSAcK IDNot Available
Chemspider ID13844817
KEGG Compound IDC06604
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkParathion
METLIN IDNot Available
PubChem Compound991
PDB IDNot Available
ChEBI ID27928
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bohn G, Rucker G, Luckas KH: [Mass spectrometric and gaschromatographic detection of parathione in autopsy material after murder by poisoning]. Z Rechtsmed. 1971;68(1):45-52. [PubMed:5547745 ]
  2. SALAMA S, EL-SHIHY A, IBRAHIM HH, KODSY A: THE ACTION OF PARATHIONE ON THE C.N.S. J Egypt Med Assoc. 1963;46:500-8. [PubMed:14066548 ]
  3. Youssef SH, el-Sayed MG, Atef M: Influence of gentamicin and rifamycin on toxicity and biotransformation of methyl parathione in rats. Dtsch Tierarztl Wochenschr. 1987 Apr 8;94(4):203-5. [PubMed:3297603 ]
  4. Innocenti A, Supuran CT: Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of alpha- but not of beta-, gamma- and zeta-carbonic anhydrases. Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12. doi: 10.1016/j.bmcl.2010.08.110. Epub 2010 Aug 26. [PubMed:20833546 ]
  5. Kawahara K, Tanaka A, Yoon J, Yokota A: Reclassification of a parathione-degrading Flavobacterium sp. ATCC 27551 as Sphingobium fuliginis. J Gen Appl Microbiol. 2010 Jun;56(3):249-55. [PubMed:20647682 ]
  6. Lotz W, Fasske E: [Pneumonitis with fatal pulmonary fibrosis (Hamman-Rich syndrome) due to parathion-(E-605-) poisoning]. Rofo. 1986 May;144(5):536-41. [PubMed:3012677 ]
  7. SALAMA S, EL-SHISHY A, IBRAHIM HH: THE ACTION OF PARATHIONE ON THE CIRCULATORY & RESPIRATORY SYSTEMS. J Egypt Med Assoc. 1963;46:240-62. [PubMed:14065272 ]
  8. Mueller RF, Hornung S, Furlong CE, Anderson J, Giblett ER, Motulsky AG: Plasma paraoxonase polymorphism: a new enzyme assay, population, family, biochemical, and linkage studies. Am J Hum Genet. 1983 May;35(3):393-408. [PubMed:6305189 ]

Only showing the first 10 proteins. There are 27 proteins in total.

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
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075

Only showing the first 10 proteins. There are 27 proteins in total.