(E)-Monocrotophos
(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 | (E)-Monocrotophos(F05110) |
| 2D Structure | |
| Description | Monocrotophos is an organophosphorus insecticide and acaricide which works systemically and on contact. It is extremely toxic to birds and is used as a bird poison. It is also very poisonous to mammals. It is used to control a variety of sucking, chewing and boring insects and spider mites on cotton, sugarcane, peanuts, ornamentals, and tobacco. The EPA classifies monocrotophos as a class I toxicity - highly toxic. Use of monocrotophos on potatoes and tomatoes was withdrawn in 1985. All applications of monocrotophos were discontinued in the United States in 1988. |
| FRCD ID | F05110 |
| CAS Number | 6923-22-4 |
| PubChem CID | 5371562 |
| Formula | C7H14NO5P |
| IUPAC Name | dimethyl [(E)-4-(methylamino)-4-oxobut-2-en-2-yl] phosphate |
| InChI Key | KRTSDMXIXPKRQR-AATRIKPKSA-N |
| InChI | InChI=1S/C7H14NO5P/c1-6(5-7(9)8-2)13-14(10,11-3)12-4/h5H,1-4H3,(H,8,9)/b6-5+ |
| Canonical SMILES | CC(=CC(=O)NC)OP(=O)(OC)OC |
| Isomeric SMILES | C/C(=C\C(=O)NC)/OP(=O)(OC)OC |
| Synonyms |
MONOCROTOPHOS
Azodrin
Nuvacron
Corophos
Monocron
Monostar
Parryfos
Apadrin
Pillardrin
Biloborn
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic phosphoric acids and derivatives |
| Subclass | Phosphate esters |
| Intermediate Tree Nodes | Alkyl phosphates |
| Direct Parent | Dialkyl phosphates |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Dialkyl phosphate - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid derivative - Carboximidic acid - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 223.165 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Complexity | 267 |
| Monoisotopic Mass | 223.061 |
| Exact Mass | 223.061 |
| XLogP | -0.2 |
| 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+ | 0.9644 |
| Human Intestinal Absorption | HIA+ | 0.9238 |
| Caco-2 Permeability | Caco2- | 0.5168 |
| P-glycoprotein Substrate | Non-substrate | 0.8738 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7478 |
| Non-inhibitor | 0.8670 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9589 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7808 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8343 |
| CYP450 2D6 Substrate | Non-substrate | 0.8286 |
| CYP450 3A4 Substrate | Substrate | 0.5104 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7956 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8314 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9205 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7920 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8482 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8883 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9520 |
| Non-inhibitor | 0.9680 | |
| AMES Toxicity | AMES toxic | 0.9108 |
| Carcinogens | Carcinogens | 0.5509 |
| Fish Toxicity | Low FHMT | 0.6004 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7991 |
| Honey Bee Toxicity | High HBT | 0.8726 |
| Biodegradation | Ready biodegradable | 0.6884 |
| Acute Oral Toxicity | I | 0.7954 |
| Carcinogenicity (Three-class) | Non-required | 0.4417 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.5874 | LogS |
| Caco-2 Permeability | 0.6402 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.4145 | LD50, mol/kg |
| Fish Toxicity | 1.3440 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1932 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| 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* | 26/04/2013 | |
| 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* | 26/04/2013 | |
| Kumquats (Marumi kumquats/round kumquats, Nagami kumquats/oval kumquats, Other species and hybrids of genus Fortunella, not elsewhere mentioned,) | 0161040 | European Union | 0.01* | 26/04/2013 | |
| Onions ('Cipollotto Nocerino PDO', Pearl onions, Rakkyo/Chinese onions, Silverskin onions/pickled onions,) | 0220020 | European Union | 0.02* | 26/04/2013 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 0.01* | 26/04/2013 | |
| Purslanes (Agretti, Glassworts/samphires, Rock samphires, Sea asters, Sea lavenders, Winter purslanes/miner's lettuces, Karkallas/Hottentot figs/Iceplant leaves,) | 0252020 | European Union | 0.01* | 26/04/2013 | |
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 0.02* | 26/04/2013 | |
| Wild fungi (Ceps/porcino mushrooms, Chanterelles, Hedgehog mushrooms, Horns of plenty/black trumpets, Morels, Périgord black truffles, Piemont white truffles, Saint George's mushrooms, Scotch bonne... | 0280020 | European Union | 0.01* | 26/04/2013 | |
| Valerian (Blue flag, Calamus, Couch grass, Cowslip/primrose, Echinacea, Echinacea, Echinacea, Elecampane, Fragrant sumac, Golden root, Herb bennet, Marshmallow, Mexican valerian, Pimpernel, Rhatany... | 0633010 | European Union | 0.05* | 26/04/2013 | |
| (d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark... | 0639000 | European Union | 0.05* | 26/04/2013 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 26/04/2013 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 26/04/2013 | |
| 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* | 26/04/2013 | |
| Others (2) | 0110990 | European Union | 0.01* | 26/04/2013 | |
| Tree nuts | 0120000 | European Union | 0.02* | 26/04/2013 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 26/04/2013 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 26/04/2013 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 26/04/2013 | |
| Chestnuts | 0120040 | European Union | 0.02* | 26/04/2013 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.02* | 26/04/2013 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Glucose-rich diet aggravates monocrotophos-induced dopaminergic neuronaldysfunction in Caenorhabditis elegans. | J Appl Toxicol | 2017 Jun | 27995639 |
| Monitoring of Pesticide Residues in Commonly Used Fruits and Vegetables inKuwait. | Int J Environ Res Public Health | 2017 Jul 25 | 28757570 |
| Pesticide Residues on Three Cut Flower Species and Potential Exposure of Floristsin Belgium. | Int J Environ Res Public Health | 2016 Sep 23 | 27669276 |
| Applications in environmental risk assessment of biochemical analysis on theIndian fresh water fish, Labeo rohita exposed to monocrotophos pesticide. | Environ Toxicol Pharmacol | 2016 Oct | 27771501 |
| Effect of monocrotophos, an organophosphorus insecticide, on the striataldopaminergic system in a mouse model of Parkinson's disease. | Toxicol Ind Health | 2016 Jul | 25227224 |
| Antioxidant and neuroprotective potential of chitooligomers in Caenorhabditiselegans exposed to Monocrotophos. | Carbohydr Polym | 2016 Jan 1 | 26453861 |
| Analysis of Insecticides in Dead Wild Birds in Korea from 2010 to 2013. | Bull Environ Contam Toxicol | 2016 Jan | 26573839 |
| Upconversion nanoparticle-based fluorescence resonance energy transfer assay for organophosphorus pesticides. | Biosens Bioelectron | 2015 Jun 15 | 25569873 |
| Organophosphorus insecticide, monocrotophos, possesses the propensity to induceinsulin resistance in rats on chronic exposure. | J Diabetes | 2015 Jan | 24698518 |
| Organophosphate pesticides-induced changes in the redox status of rat tissues and protective effects of antioxidant vitamins. | Environ Toxicol | 2015 Apr | 24248738 |
| Monitoring of pesticide residues in human breast milk from Punjab, India and its correlation with health associated parameters. | Bull Environ Contam Toxicol | 2014 Oct | 25011502 |
| Glucose feeding during development aggravates the toxicity of theorganophosphorus insecticide Monocrotophos in the nematode, Caenorhabditiselegans. | Physiol Behav | 2014 May 28 | 24780411 |
| 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 |
| Ensuring selectivity and sensitivity by timed- and ultra-selective reactionmonitoring during gas chromatography-tandem mass spectrometric determination ofpesticides. | J Chromatogr A | 2013 Nov 29 | 24161146 |
| Dispersive microextraction based on "magnetic water" coupled to gaschromatography/mass spectrometry for the fast determination of organophosphoruspesticides in cold-pressed vegetable oils. | J Agric Food Chem | 2013 Jun 5 | 23687955 |
| Pesticide residues in vegetable samples from the Andaman Islands, India. | Environ Monit Assess | 2013 Jul | 23208759 |
| Computational and experimental investigation of molecular imprinted polymers for selective extraction of dimethoate and its metabolite omethoate from olive oil. | J Chromatogr A | 2013 Jan 25 | 23290360 |
| 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 |
| Acetylcholinesterase biosensor based on chitosan/prussian blue/multiwall carbonnanotubes/hollow gold nanospheres nanocomposite film by one-stepelectrodeposition. | Biosens Bioelectron | 2013 Apr 15 | 23202341 |
| Toxic impact of two organophosphate insecticides on biochemical parameters of a food fish and assessment of recovery response. | Toxicol Ind Health | 2012 May | 21983276 |
Targets
- General Function:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 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:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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:
- 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:
- 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 ]