Ethion
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Ethion(F03343) |
| 2D Structure | |
| Description | Ethion is an organophosphate pesticide. It does not occur naturally in the environment. Ethion is used in agriculture, mainly to control insects on citrus trees, but also on cotton, fruit and nut trees, and some vegetables. It may also be used on lawns and turf grasses, but it is not used in the home for pest control. Ethion affects the nervous systems by inhibiting acetylcholineserases. (L1191) |
| FRCD ID | F03343 |
| CAS Number | 563-12-2 |
| PubChem CID | 3286 |
| Formula | C9H22O4P2S4 |
| IUPAC Name | diethoxyphosphinothioylsulfanylmethylsulfanyl-diethoxy-sulfanylidene-$l^{5}-phosphane |
| InChI Key | RIZMRRKBZQXFOY-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H22O4P2S4/c1-5-10-14(16,11-6-2)18-9-19-15(17,12-7-3)13-8-4/h5-9H2,1-4H3 |
| Canonical SMILES | CCOP(=S)(OCC)SCSP(=S)(OCC)OCC |
| Isomeric SMILES | CCOP(=S)(OCC)SCSP(=S)(OCC)OCC |
| Wikipedia | Ethion |
| Synonyms |
Nialate
ethion
Diethion
563-12-2
Ethanox
Ethopaz
Embathion
Rhodocide
Ethodan
Hylemox
|
| Classifies |
Pollutant
Veterinary Drug
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic dithiophosphoric acids and derivatives |
| Subclass | Dithiophosphate O-esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Dithiophosphate O-esters |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Dithiophosphate o-ester - Dithiophosphate s-ester - Sulfenyl compound - Organothiophosphorus compound - Organic oxygen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dithiophosphate o-esters. These are o-ester derivatives of dithiophosphates, with the general structure RSP(O)(O)=S (R = organyl group). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 384.459 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 12 |
| Complexity | 279 |
| Monoisotopic Mass | 383.988 |
| Exact Mass | 383.988 |
| XLogP | 5.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| 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+ | 0.8971 |
| Human Intestinal Absorption | HIA+ | 0.9878 |
| Caco-2 Permeability | Caco2- | 0.5437 |
| P-glycoprotein Substrate | Non-substrate | 0.8457 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7028 |
| Non-inhibitor | 0.9205 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9406 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6257 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8357 |
| CYP450 2D6 Substrate | Non-substrate | 0.8439 |
| CYP450 3A4 Substrate | Non-substrate | 0.6242 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8505 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7455 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9167 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7497 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5223 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7021 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8863 |
| Non-inhibitor | 0.9242 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Carcinogens | 0.7577 |
| Fish Toxicity | High FHMT | 0.7948 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6571 |
| Honey Bee Toxicity | High HBT | 0.9543 |
| Biodegradation | Not ready biodegradable | 0.9121 |
| Acute Oral Toxicity | I | 0.8371 |
| Carcinogenicity (Three-class) | Non-required | 0.6643 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.4469 | LogS |
| Caco-2 Permeability | 0.7259 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.1074 | LD50, mol/kg |
| Fish Toxicity | 2.1854 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.4379 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Banana | Japan | 0.3ppm | |||
| Almonds | Korea | 0.1ppm | |||
| Onions | Korea | 1ppm | |||
| Citrus fruits | 0110000 | European Union | 0.01* | 21/10/2011 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 21/10/2011 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 21/10/2011 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 21/10/2011 | |
| Others (2) | 0110990 | European Union | 0.01* | 21/10/2011 | |
| Tree nuts | 0120000 | European Union | 0.02* | 21/10/2011 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 21/10/2011 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 21/10/2011 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 21/10/2011 | |
| Chestnuts | 0120040 | European Union | 0.02* | 21/10/2011 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 21/10/2011 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 21/10/2011 | |
| Macadamias | 0120070 | European Union | 0.02* | 21/10/2011 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.02* | 21/10/2011 | |
| Pistachios | 0120100 | European Union | 0.02* | 21/10/2011 | |
| Walnuts | 0120110 | European Union | 0.02* | 21/10/2011 | |
| Others (2) | 0120990 | European Union | 0.02* | 21/10/2011 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Target vs non-target analysis to determine pesticide residues in fruits fromSaudi Arabia and influence in potential risk associated with exposure. | Food Chem Toxicol | 2018 Jan | 29109044 |
| Revealing Pesticide Residues Under High Pesticide Stress in Taiwan's AgriculturalEnvironment Probed by Fresh Honey Bee (Hymenoptera: Apidae) Pollen. | J Econ Entomol | 2017 Oct 1 | 28981672 |
| Agricultural pesticides and veterinary substances in Uruguayan beeswax. | Chemosphere | 2017 Jun | 28284118 |
| Occurrence of pesticide residues in Spanish beeswax. | Sci Total Environ | 2017 Dec 15 | 28679118 |
| Evidence of in vitro metabolic interaction effects of a chlorfenvinphos, ethionand linuron mixture on human hepatic detoxification rates. | Chemosphere | 2017 Aug | 28476006 |
| Prioritization of pesticides based on daily dietary exposure potential asdetermined from the SHEDS model. | Food Chem Toxicol | 2016 Oct | 27497764 |
| A single method for detecting 11 organophosphate pesticides in human plasma andbreastmilk using GC-FPD. | J Chromatogr B Analyt Technol Biomed Life Sci | 2016 Jul 1 | 27232054 |
| Spatio-temporal patterns of pesticide residues in the Turia and Júcar Rivers(Spain). | Sci Total Environ | 2016 Jan 1 | 26118860 |
| Rapid determination of residues of pesticides in honey by µGC-ECD and GC-MS/MS:Method validation and estimation of measurement uncertainty according to documentNo. SANCO/12571/2013. | J Environ Sci Health B | 2016 | 26671720 |
| Hazard index, a tool for a long term risk assessment of pesticide residues insome commodities, a pilot study. | Regul Toxicol Pharmacol | 2015 Dec | 26382608 |
| Superparamagnetic core-shells anchored onto graphene oxide grafted withphenylethyl amine as a nano-adsorbent for extraction and enrichment oforganophosphorus pesticides from fruit, vegetable and water samples. | J Chromatogr A | 2015 Aug 7 | 26129984 |
| Pesticide Residues in Bovine Milk in Punjab, India: Spatial Variation and RiskAssessment to Human Health. | Arch Environ Contam Toxicol | 2015 Aug | 26008642 |
| Fate of 14C-ethion insecticide in the presence of deltamethrin and dimilinpesticides in cotton seeds and oils, removal of ethion residues in oils, andbioavailability of its bound residues to experimental animals. | J Agric Food Chem | 2014 Dec 24 | 25420216 |
| Residues of organophosphate pesticides used in vegetable cultivation in ambientair, surface water and soil in Bueng Niam Subdistrict, Khon Kaen, Thailand. | Southeast Asian J Trop Med Public Health | 2013 Nov | 24450247 |
| Pesticide residues in vegetable samples from the Andaman Islands, India. | Environ Monit Assess | 2013 Jul | 23208759 |
| Distribution, fate and histopathological effects of ethion insecticide onselected organs of the crayfish, Procambarus clarkii. | Food Chem Toxicol | 2013 Feb | 23127602 |
| Monitoring of pesticide residues in South Indian tea. | Environ Monit Assess | 2013 Aug | 23341056 |
| Residues of ¹⁴C-ethion along the extraction and refining process of maize oil,and the bioavailability of bound residues in the cake for experimental animals. | Bull Environ Contam Toxicol | 2013 Aug | 23765209 |
| Detection of pesticides in active and depopulated beehives in Uruguay. | Int J Environ Res Public Health | 2011 Oct | 22073016 |
| Levels of select organophosphates in human colostrum and mature milk samples inrural region of Faizabad district, Uttar Pradesh, India. | Hum Exp Toxicol | 2011 Oct | 21247996 |
Targets
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 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:
- Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
- Gene Name:
- NR1I3
- Uniprot ID:
- Q14994
- Molecular Weight:
- 39942.145 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:
- Steroid hydroxylase 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:
- 55930.545 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. Binds preferentially to double-stranded oligonucleotide direct repeats having the consensus half-site sequence 5'-AGGTCA-3' and 4-nt spacing (DR-4). Regulates cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8; DLDLR and LRP8. Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Exhibits a ligand-dependent transcriptional activation activity (PubMed:25661920).
- Gene Name:
- NR1H2
- Uniprot ID:
- P55055
- Molecular Weight:
- 50973.375 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. Interaction with RXR shifts RXR from its role as a silent DNA-binding partner to an active ligand-binding subunit in mediating retinoid responses through target genes defined by LXRES. LXRES are DR4-type response elements characterized by direct repeats of two similar hexanuclotide half-sites spaced by four nucleotides. Plays an important role in the regulation of cholesterol homeostasis, regulating cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8. Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Exhibits a ligand-dependent transcriptional activation activity (PubMed:25661920).
- Gene Name:
- NR1H3
- Uniprot ID:
- Q13133
- Molecular Weight:
- 50395.34 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 hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 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
- Kojima H, Sata F, Takeuchi S, Sueyoshi T, Nagai T: Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87. doi: 10.1016/j.tox.2010.11.008. Epub 2010 Nov 27. [21115097 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
- Gene Name:
- VDR
- Uniprot ID:
- P11473
- Molecular Weight:
- 48288.64 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:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 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 hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 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 ]