Azamethiphos
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Basic Info
| Common Name | Azamethiphos(F05028) |
| 2D Structure | |
| Description | Azamethiphos is an organophosphorus insecticide that acts by inhibition of cholinesterase activity. In veterinary medicine it is used in fish farming to control external parasites in Atlantic salmon. It exhibits moderate acute oral toxicity to mammals but has high acute oral toxicity to birds. |
| FRCD ID | F05028 |
| CAS Number | 35575-96-3 |
| PubChem CID | 71482 |
| Formula | C9H10ClN2O5PS |
| IUPAC Name | 6-chloro-3-(dimethoxyphosphorylsulfanylmethyl)-[1,3]oxazolo[4,5-b]pyridin-2-one |
| InChI Key | VNKBTWQZTQIWDV-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3 |
| Canonical SMILES | COP(=O)(OC)SCN1C2=NC=C(C=C2OC1=O)Cl |
| Isomeric SMILES | COP(=O)(OC)SCN1C2=NC=C(C=C2OC1=O)Cl |
| Synonyms |
Ciba-Geigy 18809
Azamethiphos
35575-96-3
Snip
Azamethiphos [BAN]
CGA 18809
Azamethiophos
OMS No 1825
C9H10ClN2O5PS
UNII-9440R8149U
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Oxazolopyridines |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Oxazolopyridines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 1,3-oxazolopyridine - Aryl chloride - Aryl halide - Pyridine - Azole - Oxazole - Heteroaromatic compound - Azacycle - Sulfenyl compound - Organothiophosphorus compound - Oxacycle - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as oxazolopyridines. These are polycyclic compounds containing an oxazole ring fused to a pyridine ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 324.672 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 5 |
| Complexity | 393 |
| Monoisotopic Mass | 323.974 |
| Exact Mass | 323.974 |
| XLogP | 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+ | 0.8230 |
| Human Intestinal Absorption | HIA+ | 0.6469 |
| Caco-2 Permeability | Caco2- | 0.5584 |
| P-glycoprotein Substrate | Non-substrate | 0.7621 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8146 |
| Non-inhibitor | 0.6461 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8909 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6669 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7973 |
| CYP450 2D6 Substrate | Non-substrate | 0.8016 |
| CYP450 3A4 Substrate | Substrate | 0.5940 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5243 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5000 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8074 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5589 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.5868 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5348 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8611 |
| Non-inhibitor | 0.6556 | |
| AMES Toxicity | Non AMES toxic | 0.6149 |
| Carcinogens | Non-carcinogens | 0.7934 |
| Fish Toxicity | High FHMT | 0.8389 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9401 |
| Honey Bee Toxicity | High HBT | 0.6171 |
| Biodegradation | Not ready biodegradable | 0.7088 |
| Acute Oral Toxicity | III | 0.7974 |
| Carcinogenicity (Three-class) | Non-required | 0.5520 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0084 | LogS |
| Caco-2 Permeability | 0.5054 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4088 | LD50, mol/kg |
| Fish Toxicity | 1.2462 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6412 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Poultry,Eggs | Japan | 0.05ppm | |||
| Chicken,Eggs | Japan | 0.05ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.05ppm | |||
| Chicken,Edible Offal | Japan | 0.05ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.05ppm | |||
| Chicken,Kidney | Japan | 0.05ppm | |||
| Other Poultry Animals,Liver | Japan | 0.05ppm | |||
| Chicken,Liver | Japan | 0.05ppm | |||
| Other Poultry Animals,Fat | Japan | 0.05ppm | |||
| Chicken,Fat | Japan | 0.05ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.05ppm | |||
| Chicken,Muscle | Japan | 0.05ppm | |||
| Other Cereal Grains | Japan | 0.1ppm | |||
| Buckwheat | Japan | 0.1ppm | |||
| Corn(Maize) | Japan | 0.1ppm | |||
| Rye | Japan | 0.1ppm | |||
| Barley | Japan | 0.1ppm | |||
| Wheat | Japan | 0.1ppm | |||
| Rice(Brown Rice) | Japan | 0.1ppm | |||
| Lettuce | Switzerland | 0.02mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Pesticides in seaweed: optimization of pressurized liquid extraction and in-cell clean-up and analysis by liquid chromatography-mass spectrometry. | Anal Bioanal Chem | 2012 Jul | 22638882 |
| Genotoxicity testing of some organophosphate insecticides in the Drosophila wing spot test. | Food Chem Toxicol | 2005 Mar | 15680680 |
| Long-term effectiveness of grain protectants and structural treatments againstLiposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of storedproducts. | Pest Manag Sci | 2002 Dec | 12476995 |
| Impact of an insecticide resistance strategy for house fly (Diptera: Muscidae)control in intensive animal units in the United Kingdom. | J Econ Entomol | 2002 Dec | 12539838 |
| Visual responses of Musca domestica to pheromone impregnated targets in poultry units. | Med Vet Entomol | 1999 May | 10484159 |
Targets
- 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:
- Zinc ion binding
- Specific Function:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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:
- Prostaglandin e receptor activity
- Specific Function:
- Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
- Gene Name:
- PTGER2
- Uniprot ID:
- P43116
- Molecular Weight:
- 39759.945 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:
- Tumor necrosis factor receptor binding
- Specific Function:
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Upregulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:22517918).The TNF intracellular domain (ICD) form induces IL12 production in dendritic cells.
- Gene Name:
- TNF
- Uniprot ID:
- P01375
- Molecular Weight:
- 25644.15 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:
- 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:
- Primary amine oxidase activity
- Specific Function:
- Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and signal transduction. The VCAM1/ITGA4/ITGB1 interaction may play a pathophysiologic role both in immune responses and in leukocyte emigration to sites of inflammation.
- Gene Name:
- VCAM1
- Uniprot ID:
- P19320
- Molecular Weight:
- 81275.43 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 hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 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:
- Hydroxymethylglutaryl-coa synthase activity
- Specific Function:
- This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
- Gene Name:
- HMGCS2
- Uniprot ID:
- P54868
- Molecular Weight:
- 56634.915 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 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 ]