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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:15:53 UTC |
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HMDB ID | HMDB0001355 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Parathion |
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Description | Parathion is a highly toxic cholinesterase inhibitor that is used as an acaricide and as an insecticide. |
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Structure | |
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Synonyms | Value | Source |
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Diethyl P-nitrophenyl thiophosphate | ChEBI | Diethyl parathion | ChEBI | DNTP | ChEBI | Ethyl parathion | ChEBI | O,O-Diethyl O-(4-nitrophenyl) thiophosphate | ChEBI | O,O-Diethyl O-(P-nitrophenyl) thiophosphate | ChEBI | O,O-Diethyl O-P-nitrophenyl phosphorothioate | ChEBI | Phosphorothioic acid, O,O-diethyl O-(4-nitrophenyl) ester | ChEBI | Thiophos | ChEBI | Diethyl P-nitrophenyl thiophosphoric acid | Generator | O,O-Diethyl O-(4-nitrophenyl) thiophosphoric acid | Generator | O,O-Diethyl O-(P-nitrophenyl) thiophosphoric acid | Generator | O,O-Diethyl O-P-nitrophenyl phosphorothioic acid | Generator | Phosphorothioate, O,O-diethyl O-(4-nitrophenyl) ester | Generator | Alkron | HMDB | Alleron | HMDB | American cyanamid 3422 | HMDB | Aphamite | HMDB | Aqua 9-parathion | HMDB | Aralo | HMDB | Bladan | HMDB | Bladen | HMDB | Corothion | HMDB | Corthione | HMDB | Danthion | HMDB | Deoxynucleoside 5'-triphosphate | HMDB | Diethyl 4-nitrophenyl phosphorothionate | HMDB | Diethyl O-P-nitrophenyl phosphorothioate | HMDB | Diethyl O-P-nitrophenyl phosphorothioic acid | HMDB | Diethyl P-nitrophenyl thionophosphate | HMDB | Diethyl para-nitrophenol thiophosphate | HMDB | Diethyl-P-nitrophenyl monothiophosphate | HMDB | Diethylparathion | HMDB | Drexel parathion 8E | HMDB | Durathion | HMDB | Ecatox | HMDB | Ethlon | HMDB | Ethyl parathion (O,O-diethyl-O-P-nitrophenylthiophosphate) | HMDB | Etilon | HMDB | Foliclal | HMDB | Folidol | HMDB | Folidol e e 605 | HMDB | Folidol e605 | HMDB | Folidol oil | HMDB | Fosfermo | HMDB | Fosferno | HMDB | fosferno 50 | HMDB | Fosfex | HMDB | Fosfive | HMDB | Fosova | HMDB | Fostern | HMDB | Fostox | HMDB | Gearphos | HMDB | Genithion | HMDB | Kolphos | HMDB | Kypthion | HMDB | Lethalaire g-54 | HMDB | Lirothion | HMDB | Murfos | HMDB | Niran | HMDB | Nitrostygmine | HMDB | Niuif-100 | HMDB | Nourithion | HMDB | O,O-Diethyl-O-(P-nitrophenyl)thionophosphate | HMDB | Oleofos 20 | HMDB | Oleoparaphene | HMDB | Oleoparathion | HMDB | OMS 19 | HMDB | Orthophos | HMDB | P-Nitrophenol O-ester with O,O-diethylphosphorothioate | HMDB | P-Nitrophenol O-ester with O,O-diethylphosphorothioic acid | HMDB | PAC | HMDB | Pacol | HMDB | Panthion | HMDB | Paradust | HMDB | Paramar | HMDB | Paramar 50 | HMDB | Paraphos | HMDB | Parathene | HMDB | Parathion-e | HMDB | Parawet | HMDB | Parthion | HMDB | Penncap e | HMDB | Pestox plus | HMDB | Pethion | HMDB | Phoskil | HMDB | Phosphemol | HMDB | Phosphenol | HMDB | Phosphorothioate | HMDB | Phosphorothioic acid | HMDB | Phosphorothioic acid O,O-diethyl-O-(4-nitrophenyl) ester | HMDB | Phosphostigmine | HMDB | Rhodiasol | HMDB | Rhodiatox | HMDB | Rhodiatrox | HMDB | Selephos | HMDB | Sixty-three special e.c | HMDB | Soprathion | HMDB | Stabilized ethyl parathion | HMDB | Stathion | HMDB | Strathion | HMDB | Sulfos | HMDB | Super rodiatox | HMDB | T-47 | HMDB | Thiomex | HMDB | Thionspray no.84 | HMDB | Thiophos 3422 | HMDB | Tiofos | HMDB | Vapophos | HMDB | Viran | HMDB | Vitrex | HMDB | Thiofos | MeSH | Parathion, ethyl | MeSH |
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Chemical Formula | C10H14NO5PS |
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Average Molecular Weight | 291.261 |
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Monoisotopic Molecular Weight | 291.033029765 |
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IUPAC Name | O,O-diethyl O-4-nitrophenyl phosphorothioate |
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Traditional Name | O,O-diethyl O-4-nitrophenyl phosphorothioate |
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CAS Registry Number | 56-38-2 |
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SMILES | CCOP(=S)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O |
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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 |
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InChI Key | LCCNCVORNKJIRZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This compound 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic thiophosphoric acids and derivatives |
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Sub Class | Thiophosphoric acid esters |
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Direct Parent | Phenyl thiophosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: Environmental role: |
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Physical Properties |
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State | Liquid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 6.1 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.011 mg/mL | Not Available | LogP | 3.83 | Not Available |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03fr-1390000000-256208006a2b1561db1b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-01p9-0090000000-fe8742077ddcdaa84280 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-000i-0190000000-af44a385ea22b6326819 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-000l-1940000000-218556da13b43e16e2bf | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-01vo-2910000000-4a40f241595d8b5628d0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-01vo-4900000000-c58ec980fa6b4210133c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-01ox-6900000000-80ce5f0f59ebc4a62681 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-1090000000-e7daa1435a3c8202b8dc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00lr-1090000000-0ee220c0c9ec67d726bb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004j-9720000000-be163305078ac89a7681 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0390000000-3cdf27289e65564f2028 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0490000000-9b32c86de4c27c33c405 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000f-1940000000-6f5772e73d0e7958d6cb | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-0a74-8940000000-4bf55c77de23f747eb80 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | - Cerebrospinal Fluid (CSF)
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.0687-68.721 uM | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022574 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 13844817 |
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KEGG Compound ID | C06604 |
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BioCyc ID | PARATHION |
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BiGG ID | Not Available |
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Wikipedia Link | Parathion |
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METLIN ID | Not Available |
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PubChem Compound | 991 |
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PDB ID | Not Available |
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ChEBI ID | 27928 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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