Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:23:26 UTC |
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HMDB ID | HMDB0001504 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Aminoparathion |
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Description | Aminoparathion, also known as e 605 reduced or parathion amino, 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. Aminoparathion has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make aminoparathion a potential biomarker for the consumption of these foods. Aminoparathion is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Aminoparathion. |
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Structure | CCOP(=S)(OCC)OC1=CC=C(N)C=C1 InChI=1S/C10H16NO3PS/c1-3-12-15(16,13-4-2)14-10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3 |
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Synonyms | Value | Source |
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4-Aminoparathion | ChEBI | Amino-parathion | ChEBI | e 605 Reduced | ChEBI | O,O-Diethyl O-(4-aminophenyl) phosphorothioate | ChEBI | p-Aminoparathion | ChEBI | Parathion amino | ChEBI | Phosphorothioic acid, O-(4-aminophenyl) O,O-diethyl ester | ChEBI | Thiophosphoric acid diethyl 4-aminophenyl ester | ChEBI | Thiophosphoric acid O-(4-aminophenyl) O,O-diethyl ester | ChEBI | O,O-Diethyl O-(4-aminophenyl) phosphorothioic acid | Generator | Phosphorothioate, O-(4-aminophenyl) O,O-diethyl ester | Generator | Thiophosphate diethyl 4-aminophenyl ester | Generator | Thiophosphate O-(4-aminophenyl) O,O-diethyl ester | Generator | AP | HMDB |
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Chemical Formula | C10H16NO3PS |
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Average Molecular Weight | 261.278 |
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Monoisotopic Molecular Weight | 261.058850585 |
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IUPAC Name | O-4-aminophenyl O,O-diethyl phosphorothioate |
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Traditional Name | O-4-aminophenyl O,O-diethyl phosphorothioate |
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CAS Registry Number | 3735-01-1 |
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SMILES | CCOP(=S)(OCC)OC1=CC=C(N)C=C1 |
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InChI Identifier | InChI=1S/C10H16NO3PS/c1-3-12-15(16,13-4-2)14-10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3 |
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InChI Key | XIZOTXGJXSTQDI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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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
- Phenoxy compound
- Aniline or substituted anilines
- Thiophosphate triester
- Benzenoid
- Monocyclic benzene moiety
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Amine
- 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 | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.39 mg/mL | Not Available | LogP | 2.60 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Aminoparathion,1TMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C)C=C1 | 2028.1 | Semi standard non polar | 33892256 | Aminoparathion,1TMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C)C=C1 | 2058.6 | Standard non polar | 33892256 | Aminoparathion,1TMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C)C=C1 | 2535.8 | Standard polar | 33892256 | Aminoparathion,2TMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 2052.2 | Semi standard non polar | 33892256 | Aminoparathion,2TMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 2176.4 | Standard non polar | 33892256 | Aminoparathion,2TMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1 | 2445.4 | Standard polar | 33892256 | Aminoparathion,1TBDMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1 | 2260.0 | Semi standard non polar | 33892256 | Aminoparathion,1TBDMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1 | 2269.3 | Standard non polar | 33892256 | Aminoparathion,1TBDMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1 | 2642.7 | Standard polar | 33892256 | Aminoparathion,2TBDMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2502.3 | Semi standard non polar | 33892256 | Aminoparathion,2TBDMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2568.1 | Standard non polar | 33892256 | Aminoparathion,2TBDMS,isomer #1 | CCOP(=S)(OCC)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1 | 2682.2 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Aminoparathion GC-MS (Non-derivatized) - 70eV, Positive | splash10-053r-3590000000-d03ad6e6ed9919f1c63d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Aminoparathion GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Positive-QTOF | splash10-03e9-0090000000-c545df9bf2db240673a7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Positive-QTOF | splash10-0bu0-1290000000-ecfc9bd4e21c704d6f94 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Positive-QTOF | splash10-017i-9230000000-0d34427339291f69a22d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Negative-QTOF | splash10-03e9-0190000000-3b1135825ef7c95e695f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Negative-QTOF | splash10-01q9-1390000000-1067d2108fe36b18e7d6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Negative-QTOF | splash10-0f79-0970000000-625ce950eeb267e2a4bf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Positive-QTOF | splash10-03di-0090000000-d3a3945fd8a4ffa895a9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Positive-QTOF | splash10-0bu0-1290000000-cce2f1cb680508f19d13 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Positive-QTOF | splash10-014l-9210000000-f58785b7a936b66d0137 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 10V, Negative-QTOF | splash10-03di-0190000000-ea30c70ed229458b486b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 20V, Negative-QTOF | splash10-0089-0790000000-34019406437ef5d82d01 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Aminoparathion 40V, Negative-QTOF | splash10-0ab9-0900000000-239d97e2d83e127ce516 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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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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FooDB ID | FDB022660 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 215 |
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KEGG Compound ID | C06605 |
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BioCyc ID | AMINO-PARATHION |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 6284 |
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PubChem Compound | 220 |
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PDB ID | Not Available |
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ChEBI ID | 28055 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Rung, Bruno; Schwack, Wolfgang. Aminoparathion: A highly reactive metabolite of parathion. 1. Reactions with polyphenols and polyphenol oxidase. Journal of Agricultural and Food Chemistry (2005), 53(23), 9140-9145. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Katan J, Fuhremann TW, Lichtenstein EP: Binding of (14C) parathion in soil: a reassessment of pesticide persistence. Science. 1976 Sep 3;193(4256):891-4. [PubMed:948750 ]
- Gorder GW, Lichtenstein EP: Degradation of parathion in culture by microorganisms found in cranberry bogs. Can J Microbiol. 1980 Apr;26(4):475-81. [PubMed:7378942 ]
- Lichtenstein EP, Fuhremann TW: Activity of an NADPH-dependent nitroreductase in houseflies. Science. 1971 May 7;172(3983):589-91. [PubMed:4396637 ]
- Wehr K: [Detection of E 605 several years after burial]. Z Rechtsmed. 1986;96(1):57-66. [PubMed:3716649 ]
- Houx NW, Dekker A: A test system for the determining of the fate of pesticides in surface water. Protocol and comparison of the performance for parathion of ecocores and micro ecosystems from two sources. Int J Environ Anal Chem. 1987;29(1-2):37-59. [PubMed:3570605 ]
- Kawar NS, Gunther FA, Iwata Y: Fate of parathion in artificially fortified grape juice processed into wine. J Environ Sci Health B. 1978;13(1):1-9. [PubMed:632538 ]
- Jimenez JJ, Bernal JL, del Nozal MJ, Toribio L, Bernal J: Determination of impurities in pesticides and their degradation products formed during the wine-making process by solid-phase extraction and gas chromatography with detection by electron ionization mass spectrometry. II. Bromopropylate, trichlorphon, parathion-methyl and tebuconazole. Rapid Commun Mass Spectrom. 2004;18(22):2629-36. [PubMed:15481093 ]
- Zhao X, Hwang HM: A study of the degradation of organophosphorus pesticides in river waters and the identification of their degradation products by chromatography coupled with mass spectrometry. Arch Environ Contam Toxicol. 2009 May;56(4):646-53. doi: 10.1007/s00244-008-9220-8. Epub 2008 Aug 28. [PubMed:18752016 ]
- Banna AA, Kawar NS: Behavior of parathion in apple juice processed into cider and vinegar. J Environ Sci Health B. 1982;17(5):505-14. [PubMed:7175099 ]
- Muhammad MA, Kawar NS: Behavior of parathion in tomatoes processed into juice and ketchup. J Environ Sci Health B. 1985 Oct;20(5):499-510. [PubMed:4078230 ]
- Chan LT, Crowley RJ, Geyer R: Detection and analysis of aminoparathion in human postmortem specimens. J Forensic Sci. 1983 Jan;28(1):122-7. [PubMed:6680731 ]
- Munnecke DM, Hsieh DP: Pathways of microbial metabolism of parathion. Appl Environ Microbiol. 1976 Jan;31(1):63-9. [PubMed:8005 ]
- Rung B, Schwack W: Aminoparathion: a highly reactive metabolite of parathion. 1. Reactions with polyphenols and polyphenol oxidase. J Agric Food Chem. 2005 Nov 16;53(23):9140-5. [PubMed:16277414 ]
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