Fosthiazate
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Basic Info
| Common Name | Fosthiazate(F05081) |
| 2D Structure | |
| Description | Fosthiazate is a member of the organophosphate class of pesticides or nematicides and is used to control nematodes species on tomatoes. |
| FRCD ID | F05081 |
| CAS Number | 98886-44-3 |
| PubChem CID | 91758 |
| Formula | C9H18NO3PS2 |
| IUPAC Name | 3-[butan-2-ylsulfanyl(ethoxy)phosphoryl]-1,3-thiazolidin-2-one |
| InChI Key | DUFVKSUJRWYZQP-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H18NO3PS2/c1-4-8(3)16-14(12,13-5-2)10-6-7-15-9(10)11/h8H,4-7H2,1-3H3 |
| Canonical SMILES | CCC(C)SP(=O)(N1CCSC1=O)OCC |
| Isomeric SMILES | CCC(C)SP(=O)(N1CCSC1=O)OCC |
| Synonyms |
Nemathorin
(RS)-S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylphosphonothioate
Fosthiazate
98886-44-3
Fosthiazate [ISO:BSI]
IKI 1145
ASC-66824
CHEBI:38692
O-Ethyl S-(1-methylpropyl) (2-oxo-3-thiazolidinyl)phosphonothioate
Phosphonothioic acid, (2-oxo-3-thiazolidinyl)-, O-ethyl S-(1-methylpropyl) ester
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Azolidines |
| Subclass | Thiazolidines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Thiazolidines |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Thiazolidine - Carbonic acid derivative - Azacycle - Sulfenyl compound - Organothiophosphorus compound - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as thiazolidines. These are heterocyclic compounds containing a five-member saturated aliphatic ring with one nitrogen atom, one sulfur atom, three carbon atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 283.341 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Complexity | 301 |
| Monoisotopic Mass | 283.047 |
| Exact Mass | 283.047 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| 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+ | 0.9557 |
| Human Intestinal Absorption | HIA+ | 0.9830 |
| Caco-2 Permeability | Caco2- | 0.5474 |
| P-glycoprotein Substrate | Non-substrate | 0.6854 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5975 |
| Non-inhibitor | 0.9555 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8532 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6328 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8000 |
| CYP450 2D6 Substrate | Non-substrate | 0.7912 |
| CYP450 3A4 Substrate | Substrate | 0.5160 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6179 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6255 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8920 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5637 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8573 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8791 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9323 |
| Non-inhibitor | 0.8937 | |
| AMES Toxicity | Non AMES toxic | 0.5829 |
| Carcinogens | Non-carcinogens | 0.7957 |
| Fish Toxicity | High FHMT | 0.9126 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9670 |
| Honey Bee Toxicity | High HBT | 0.7142 |
| Biodegradation | Ready biodegradable | 0.6157 |
| Acute Oral Toxicity | II | 0.7414 |
| Carcinogenicity (Three-class) | Non-required | 0.4879 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1631 | LogS |
| Caco-2 Permeability | 1.0304 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.6647 | LD50, mol/kg |
| Fish Toxicity | 1.6648 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3446 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Others (2) | 0153990 | European Union | 0.02* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.02* | 01/09/2008 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.02* | 01/09/2008 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.02* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.02* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.02* | 01/09/2008 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.02* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.02* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.02* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.02* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.02* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.02* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.02* | 01/09/2008 | |
| Others (2) | 0161990 | European Union | 0.02* | 01/09/2008 | |
| (b) inedible peel, small | 0162000 | European Union | 0.02* | 01/09/2008 | |
| Kiwi fruits (green, red, yellow) | 0162010 | European Union | 0.02* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Biological Control of Meloidogyne incognita by Aspergillus niger F22 Producing Oxalic Acid. | PLoS One | 2016 | 27258452 |
| Analysis of 10 systemic pesticide residues in various baby foods using liquidchromatography-tandem mass spectrometry. | Biomed Chromatogr | 2014 Jun | 24861738 |
| Proteomic response of wheat embryos to fosthiazate stress in a protectedvegetable soil. | J Environ Sci (China) | 2012 | 23520855 |
| Pesticide residues in heterogeneous plant populations, a model-based approachapplied to nematicides in banana (Musa spp.). | J Agric Food Chem | 2007 Mar 21 | 17305357 |
| Influence of soil physicochemical and biological properties on the degradationand adsorption of the nematicide fosthiazate. | J Agric Food Chem | 2006 Sep 6 | 16939340 |
| Degradation and adsorption of fosthiazate in soil. | J Agric Food Chem | 2004 Oct 6 | 15453693 |
Targets
- General Function:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 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:
- 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:
- Serine-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 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:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 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:
- Virus receptor activity
- Specific Function:
- Binds LDL, the major cholesterol-carrying lipoprotein of plasma, and transports it into cells by endocytosis. In order to be internalized, the receptor-ligand complexes must first cluster into clathrin-coated pits.(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes, but not through a direct interaction with viral proteins (PubMed:10535997, PubMed:12615904). Acts as a receptor for vesicular stomatitis virus (PubMed:23589850). In case of HIV-1 infection, may function as a receptor for extracellular Tat in neurons, mediating its internalization in uninfected cells (PubMed:11100124).
- Gene Name:
- LDLR
- Uniprot ID:
- P01130
- Molecular Weight:
- 95375.105 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:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 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 ]