Mevinphos
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Basic Info
| Common Name | Mevinphos(F05107) |
| 2D Structure | |
| Description | Mevinphos is an organophosphate insecticide that acts as an acetylcholinesterase inhibitor to control insects in a wide range of crops. It is most commonly used for the control of chewing and sucking insects, as well as spider mites. |
| FRCD ID | F05107 |
| CAS Number | 7786-34-7 |
| PubChem CID | 5355863 |
| Formula | C7H13O6P |
| IUPAC Name | methyl (E)-3-dimethoxyphosphoryloxybut-2-enoate |
| InChI Key | GEPDYQSQVLXLEU-AATRIKPKSA-N |
| InChI | InChI=1S/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3/b6-5+ |
| Canonical SMILES | CC(=CC(=O)OC)OP(=O)(OC)OC |
| Isomeric SMILES | C/C(=C\C(=O)OC)/OP(=O)(OC)OC |
| Synonyms |
(E)-Mevinphos
mevinphos
Phosdrin
Fosdrin
cis-Phosdrin
Meniphos
Phosfene
Gesfid
Menite
CMDP
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acid esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Fatty acid esters |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Fatty acid ester - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - Methyl ester - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organic oxide - Carbonyl group - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 224.149 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Complexity | 263 |
| Monoisotopic Mass | 224.045 |
| Exact Mass | 224.045 |
| XLogP | 1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9558 |
| Human Intestinal Absorption | HIA+ | 0.8834 |
| Caco-2 Permeability | Caco2- | 0.5766 |
| P-glycoprotein Substrate | Non-substrate | 0.7968 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7945 |
| Non-inhibitor | 0.8581 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9508 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8101 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8554 |
| CYP450 2D6 Substrate | Non-substrate | 0.8704 |
| CYP450 3A4 Substrate | Non-substrate | 0.5594 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8617 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8667 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9370 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7977 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8838 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9082 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8949 |
| Non-inhibitor | 0.9726 | |
| AMES Toxicity | Non AMES toxic | 0.7421 |
| Carcinogens | Carcinogens | 0.6643 |
| Fish Toxicity | High FHMT | 0.7226 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7789 |
| Honey Bee Toxicity | High HBT | 0.9342 |
| Biodegradation | Ready biodegradable | 0.6487 |
| Acute Oral Toxicity | I | 0.7747 |
| Carcinogenicity (Three-class) | Non-required | 0.4946 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.0438 | LogS |
| Caco-2 Permeability | 0.2919 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.4521 | LD50, mol/kg |
| Fish Toxicity | 1.0454 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0133 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 01/09/2008 | |
| Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E... | 0154010 | European Union | 0.01* | 01/09/2008 | |
| Carrots (Coloured carrots varieties, Baby carrots,) | 0213020 | European Union | 0.01* | 01/09/2008 | |
| Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater... | 0213040 | European Union | 0.01* | 01/09/2008 | |
| Lamb's lettuces/corn salads (Italian corn salads,) | 0251010 | European Union | 0.01* | 01/09/2008 | |
| Sorghum (Durra/jowari/milo, Sudan grass, Other species of genus Sorghum, not elsewhere mentioned,) | 0500080 | European Union | 0.01* | 01/09/2008 | |
| Wheat (Durum wheat, Einkorn wheat/small spelt/one-grain wheat, Emmer wheat, Khorasan wheat, Spelt, Triticale, Other species of genus Triticum, not elsewhere mentioned,) | 0500090 | European Union | 0.01* | 01/09/2008 | |
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 0.02* | 01/09/2008 | |
| Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,) | 0820060 | European Union | 0.02* | 01/09/2008 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 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 | 0.01* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 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 | 0.01* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.01* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.01* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Agrochemical loading in drains and rivers and its connection with pollution in coastal lagoons of the Mexican Pacific. | Environ Monit Assess | 2017 Jun | 28510105 |
| Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016 Jun | 27144891 |
| Alternative bioassay for the detection of saxitoxin using the speckled cockroach (Nauphoeta cinerea). | J Toxicol Environ Health A | 2011 | 21432713 |
| Capillary electrophoresis with immobilized quantum dot fluorescence detection forrapid determination of organophosphorus pesticides in vegetables. | Electrophoresis | 2010 Sep | 20872612 |
| Field aging of insecticides after repeated application to a northern Thailandultisol. | J Agric Food Chem | 2008 Oct 22 | 18817413 |
| Insecticide dissipation after repeated field application to a Northern ThailandUltisol. | J Agric Food Chem | 2006 Nov 1 | 17061833 |
| An analytical method for the rapid screening of organophosphate pesticides inhuman biological samples and foodstuffs. | Forensic Sci Int | 2001 Sep 15 | 11516897 |
| Observations on the accidental poisoning of birds by organophosphate insecticides and other toxic substances. | Vet Rec | 1982 Nov 13 | 7179689 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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:
- Protease binding
- Specific Function:
- Metalloproteinase inhibitor that functions by forming one to one complexes with target metalloproteinases, such as collagenases, and irreversibly inactivates them by binding to their catalytic zinc cofactor. Acts on MMP1, MMP2, MMP3, MMP7, MMP8, MMP9, MMP10, MMP11, MMP12, MMP13 and MMP16. Does not act on MMP14. Also functions as a growth factor that regulates cell differentiation, migration and cell death and activates cellular signaling cascades via CD63 and ITGB1. Plays a role in integrin signaling. Mediates erythropoiesis in vitro; but, unlike IL3, it is species-specific, stimulating the growth and differentiation of only human and murine erythroid progenitors.
- Gene Name:
- TIMP1
- Uniprot ID:
- P01033
- Molecular Weight:
- 23170.64 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:
- 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:
- 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 ]
- 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:
- 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 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Cytokine that plays an essential role in the regulation of survival, proliferation and differentiation of hematopoietic precursor cells, especially mononuclear phagocytes, such as macrophages and monocytes. Promotes the release of proinflammatory chemokines, and thereby plays an important role in innate immunity and in inflammatory processes. Plays an important role in the regulation of osteoclast proliferation and differentiation, the regulation of bone resorption, and is required for normal bone development. Required for normal male and female fertility. Promotes reorganization of the actin cytoskeleton, regulates formation of membrane ruffles, cell adhesion and cell migration. Plays a role in lipoprotein clearance.
- Gene Name:
- CSF1
- Uniprot ID:
- P09603
- Molecular Weight:
- 60178.885 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 ]