Trichlorfon
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Basic Info
| Common Name | Trichlorfon(F05150) |
| 2D Structure | |
| Description | Trichlorfon is an organophosphate insecticide used to control cockroaches, crickets, silverfish, bedbugs, fleas, cattle grubs, flies, ticks, leafminers and leaf-hoppers. It is applied to vegetable, fruit and field crops; livestock; ornamental and forestry plantings; in agricultural premises and domestic settings; in greenhouses, and for control of parasites of fish in designated aquatic environments. It is also used for treating domestic animals for control of internal parasites. Trichlorfon is a selective insecticide, meaning that it kills selected insects, but spares many or most other organisms. Trichlorfon is toxic to target insects through direct applications and by ingestion. In other words, it works both by contact and stomach poison action. Trichlorfon acts by interfering with an essential nervous system enzyme, cholinesterase. |
| FRCD ID | F05150 |
| CAS Number | 52-68-6 |
| PubChem CID | 5853 |
| Formula | C4H8Cl3O4P |
| IUPAC Name | 2,2,2-trichloro-1-dimethoxyphosphorylethanol |
| InChI Key | NFACJZMKEDPNKN-UHFFFAOYSA-N |
| InChI | InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3 |
| Canonical SMILES | COP(=O)(C(C(Cl)(Cl)Cl)O)OC |
| Isomeric SMILES | COP(=O)(C(C(Cl)(Cl)Cl)O)OC |
| Synonyms |
Trichlorphon
TRICHLORFON
Metrifonate
Chlorophos
Metriphonate
Methyl chlorophos
Bilarcil
Chlorofos
52-68-6
Chloroftalm
|
| Classifies |
Pollutant
Veterinary Drug
Illegal Additives
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic phosphonic acids and derivatives |
| Subclass | Phosphonic acid diesters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dialkyl alkylphosphonates |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 257.428 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Complexity | 183 |
| Monoisotopic Mass | 255.923 |
| Exact Mass | 255.923 |
| XLogP | 0.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9618 |
| Human Intestinal Absorption | HIA+ | 0.8840 |
| Caco-2 Permeability | Caco2- | 0.6329 |
| P-glycoprotein Substrate | Non-substrate | 0.8447 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9447 |
| Non-inhibitor | 0.9509 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9559 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8111 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8001 |
| CYP450 2D6 Substrate | Non-substrate | 0.8567 |
| CYP450 3A4 Substrate | Non-substrate | 0.5547 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9240 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6688 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9580 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9683 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9734 |
| Non-inhibitor | 0.9138 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Carcinogens | 0.7249 |
| Fish Toxicity | Low FHMT | 0.5932 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5573 |
| Honey Bee Toxicity | High HBT | 0.8934 |
| Biodegradation | Not ready biodegradable | 0.9591 |
| Acute Oral Toxicity | II | 0.7669 |
| Carcinogenicity (Three-class) | Non-required | 0.6991 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.7277 | LogS |
| Caco-2 Permeability | 0.1451 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8754 | LD50, mol/kg |
| Fish Toxicity | 1.7839 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3912 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of direct competitive biomimetic immunosorbent assay based on quantumdot label for determination of trichlorfon residues in vegetables. | Food Chem | 2018 Jun 1 | 29412902 |
| Efficacy of Chemicals for the Potential Management of the Queensland Fruit FlyBactrocera tryoni (Froggatt) (Diptera: Tephritidae). | Insects | 2017 May 9 | 28486404 |
| Enantioseparation and enantioselective behavior of trichlorfon enantiomers in sediments. | Chirality | 2017 Mar | 28321927 |
| A study on biomimetic immunoassay-capillary electrophoresis method based onmolecularly imprinted polymer for determination of trace trichlorfon residue invegetables. | Food Chem | 2017 Apr 15 | 27979090 |
| Evaluation of an FDA approved library against laboratory models of human intestinal nematode infections. | Parasit Vectors | 2016 Jul 1 | 27363703 |
| Trichlorfon-induced haematological and biochemical changes in Cyprinus carpio:ameliorative effect of propolis. | Dis Aquat Organ | 2015 Jun 3 | 26036828 |
| Susceptibility of nine organophosphorus pesticides in skimmed milk towardsinoculated lactic acid bacteria and yogurt starters. | J Sci Food Agric | 2015 Jan | 24777955 |
| Study of a molecularly imprinted solid-phase extraction coupled withhigh-performance liquid chromatography for simultaneous determination of tracetrichlorfon and monocrotophos residues in vegetables. | J Sci Food Agric | 2014 May | 24122545 |
| Pesticide-contaminated feeds in integrated grass carp aquaculture: toxicology andbioaccumulation. | Dis Aquat Organ | 2014 Feb 19 | 24553419 |
| Development of molecularly imprinted electrochemical sensors based onFe3O4@MWNT-COOH/CS nanocomposite layers for detecting traces of acephate andtrichlorfon. | Analyst | 2014 Dec 21 | 25325612 |
| Study on an electrochromatography method based on organic-inorganic hybridmolecularly imprinted monolith for determination of trace trichlorfon invegetables. | J Sci Food Agric | 2014 Aug | 24323896 |
| Simultaneous determination of ten organophosphate pesticide residues in fruits bygas chromatography coupled with magnetic separation. | J Sep Sci | 2014 Apr | 24470377 |
| Insecticide toxicity to oriental fruit fly Bactrocera dorsalis (Diptera:Tephritidae) is influenced by environmental factors. | J Econ Entomol | 2013 Feb | 23448051 |
| Simultaneous determination of nine trace organophosphorous pesticide residues in fruit samples using molecularly imprinted matrix solid-phase dispersion followed by gas chromatography. | J Agric Food Chem | 2013 Apr 24 | 23544352 |
| Effects of repeated maternal oral exposure to low levels of trichlorfon ondevelopment and cytogenetic toxicity in 3-day mouse embryos. | Food Chem Toxicol | 2011 Oct | 21771630 |
| Assessing lethal and sub-lethal effects of trichlorfon on different trophiclevels. | Aquat Toxicol | 2011 Jun | 21473847 |
| Toxic effects of chemical pesticides (trichlorfon and dimehypo) on Dunaliella salina. | Chemosphere | 2011 Jul | 21621243 |
| Study of an online molecularly imprinted solid phase extraction coupled tochemiluminescence sensor for the determination of trichlorfon in vegetables. | J Agric Food Chem | 2011 Dec 28 | 22107158 |
| A matrix solid-phase dispersion method for the extraction of seven pesticidesfrom mango and papaya. | J Chromatogr Sci | 2010 Oct | 20875237 |
| Beneficial effect of pine honey on trichlorfon induced some biochemicalalterations in mice. | Ecotoxicol Environ Saf | 2010 Jul | 20303175 |
Targets
- General Function:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Platelet-derived growth factor binding
- Specific Function:
- Collagen type III occurs in most soft connective tissues along with type I collagen. Involved in regulation of cortical development. Is the major ligand of GPR56 in the developing brain and binding to GPR56 inhibits neuronal migration and activates the RhoA pathway by coupling GPR56 to GNA13 and possibly GNA12.
- Gene Name:
- COL3A1
- Uniprot ID:
- P02461
- Molecular Weight:
- 138564.005 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Serine-type endopeptidase activity
- Specific Function:
- Converts the abundant, but inactive, zymogen plasminogen to plasmin by hydrolyzing a single Arg-Val bond in plasminogen. By controlling plasmin-mediated proteolysis, it plays an important role in tissue remodeling and degradation, in cell migration and many other physiopathological events. Plays a direct role in facilitating neuronal migration.
- Gene Name:
- PLAT
- Uniprot ID:
- P00750
- Molecular Weight:
- 62916.495 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Peptide antigen binding
- Specific Function:
- Binds peptides derived from antigens that access the endocytic route of antigen presenting cells (APC) and presents them on the cell surface for recognition by the CD4 T-cells. The peptide binding cleft accommodates peptides of 10-30 residues. The peptides presented by MHC class II molecules are generated mostly by degradation of proteins that access the endocytic route, where they are processed by lysosomal proteases and other hydrolases. Exogenous antigens that have been endocytosed by the APC are thus readily available for presentation via MHC II molecules, and for this reason this antigen presentation pathway is usually referred to as exogenous. As membrane proteins on their way to degradation in lysosomes as part of their normal turn-over are also contained in the endosomal/lysosomal compartments, exogenous antigens must compete with those derived from endogenous components. Autophagy is also a source of endogenous peptides, autophagosomes constitutively fuse with MHC class II loading compartments. In addition to APCs, other cells of the gastrointestinal tract, such as epithelial cells, express MHC class II molecules and CD74 and act as APCs, which is an unusual trait of the GI tract. To produce a MHC class II molecule that presents an antigen, three MHC class II molecules (heterodimers of an alpha and a beta chain) associate with a CD74 trimer in the ER to form a heterononamer. Soon after the entry of this complex into the endosomal/lysosomal system where antigen processing occurs, CD74 undergoes a sequential degradation by various proteases, including CTSS and CTSL, leaving a small fragment termed CLIP (class-II-associated invariant chain peptide). The removal of CLIP is facilitated by HLA-DM via direct binding to the alpha-beta-CLIP complex so that CLIP is released. HLA-DM stabilizes MHC class II molecules until primary high affinity antigenic peptides are bound. The MHC II molecule bound to a peptide is then transported to the cell membrane surface. In B-cells, the interaction between HLA-DM and MHC class II molecules is regulated by HLA-DO. Primary dendritic cells (DCs) also to express HLA-DO. Lysosomal microenvironment has been implicated in the regulation of antigen loading into MHC II molecules, increased acidification produces increased proteolysis and efficient peptide loading.
- Gene Name:
- HLA-DRA
- Uniprot ID:
- P01903
- Molecular Weight:
- 28606.685 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]