Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 14:04:22 UTC |
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Update Date | 2021-09-26 23:08:50 UTC |
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HMDB ID | HMDB0254686 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Trichlorfon |
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Description | Metrifonate, also known as trichlorfon or methyl chlorophos, belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Metrifonate is an extremely weak basic (essentially neutral) compound (based on its pKa). Metrifonate is a potentially toxic compound. It is a prodrug which is activated non-enzymatically into 2,2-dichlorovinyl dimethyl phosphate. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trichlorfon is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trichlorfon is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | COP(=O)(OC)C(O)C(Cl)(Cl)Cl InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3 |
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Synonyms | Value | Source |
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(+-)-Trichlorfon | ChEBI | 1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester | ChEBI | Chlorophos | ChEBI | Methyl chlorophos | ChEBI | Metrifonato | ChEBI | Metrifonatum | ChEBI | Trichlorfon | Kegg | 1-Hydroxy-2,2,2-trichloroethylphosphonate dimethyl ester | Generator | Metrifonic acid | Generator | Metrifonate | ChEBI | Neguvon | MeSH | Ricifon | MeSH | Trichlorphon | MeSH | Bilarcil | MeSH | Chlorofos | MeSH | Dipterex | MeSH | Dylox | MeSH | Foschlor | MeSH | Metriphonate | MeSH |
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Chemical Formula | C4H8Cl3O4P |
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Average Molecular Weight | 257.437 |
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Monoisotopic Molecular Weight | 255.922578377 |
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IUPAC Name | dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate |
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Traditional Name | briten |
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CAS Registry Number | Not Available |
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SMILES | COP(=O)(OC)C(O)C(Cl)(Cl)Cl |
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InChI Identifier | InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3 |
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InChI Key | NFACJZMKEDPNKN-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic phosphonic acids and derivatives |
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Sub Class | Phosphonic acid diesters |
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Direct Parent | Dialkyl alkylphosphonates |
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Alternative Parents | |
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Substituents | - Dialkyl alkylphosphonate
- Phosphonic acid ester
- Halohydrin
- Chlorohydrin
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organophosphorus compound
- Organooxygen compound
- Organochloride
- Organohalogen compound
- Alkyl halide
- Alkyl chloride
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 | |
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Physical Properties |
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State | Not Available |
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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 | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Trichlorfon EI-B (Non-derivatized) | splash10-0bvi-6900000000-bc340a4a5dc69af91e1c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trichlorfon GC-MS (Non-derivatized) - 70eV, Positive | splash10-08fv-4910000000-377b26693efe1dfbe4cf | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trichlorfon GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trichlorfon GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trichlorfon GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0bvj-8900000000-7ca1c4413fd81f66277d | 2014-10-20 | Not Available | 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 - Trichlorfon 10V, Positive-QTOF | splash10-0a4i-0090000000-aa5fd250bfa9fee850d5 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Positive-QTOF | splash10-0006-6970000000-dc597af04c29ce444a94 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Positive-QTOF | splash10-0006-9210000000-3d224da1d1c959e0c283 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Negative-QTOF | splash10-0pb9-1980000000-7d2bf4a5fb9e32654d66 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Negative-QTOF | splash10-0abc-3690000000-64d4c35a35ea5e4d7c9d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Negative-QTOF | splash10-00dr-3980000000-25b9c552029e0cd0cb75 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Positive-QTOF | splash10-0a4i-0920000000-dff60238bdc7e3921d70 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Positive-QTOF | splash10-0a4i-1900000000-dd9d9e4a8e56529eb0b9 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Positive-QTOF | splash10-0a6r-6900000000-734aca239b9fbf171be2 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 10V, Negative-QTOF | splash10-0udi-0090000000-6884dc582fd40332e570 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 20V, Negative-QTOF | splash10-0006-9350000000-4bb48a2037b65de50d32 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trichlorfon 40V, Negative-QTOF | splash10-05fu-3490000000-c91d932fa28ad35e2f6a | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-10-25 | Wishart Lab | View Spectrum |
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