Ethoprop
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Basic Info
| Common Name | Ethoprop(F03448) |
| 2D Structure | |
| Description | Ethoprop is an organophosphate acetylcholinesterase inhibitor used as an insecticide. It is extremely toxic to mammals. (L1195, L1655) |
| FRCD ID | F03448 |
| CAS Number | 13194-48-4 |
| PubChem CID | 3289 |
| Formula | C8H19O2PS2 |
| IUPAC Name | 1-[ethoxy(propylsulfanyl)phosphoryl]sulfanylpropane |
| InChI Key | VJYFKVYYMZPMAB-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H19O2PS2/c1-4-7-12-11(9,10-6-3)13-8-5-2/h4-8H2,1-3H3 |
| Canonical SMILES | CCCSP(=O)(OCC)SCCC |
| Isomeric SMILES | CCCSP(=O)(OCC)SCCC |
| Wikipedia | Ethoprop |
| Synonyms |
Ethoprophos
O-Ethyl S,S-dipropyl phosphorodithioate
ethoprop
13194-48-4
Prophos
Rovokil
Jolt
MOCAP
O-Ethyl S,S-dipropyl dithiophosphate
Phosethoprop
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organophosphorus compounds |
| Class | Organothiophosphorus compounds |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Organothiophosphorus compounds |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Sulfenyl compound - Organothiophosphorus compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as organothiophosphorus compounds. These are organic derivatives of thiophosphonic acid, thiophosphoric acid, dithiophosphoric acid, or phosphorotrithioic acid, or derivatives thereof. Thiophosphonic acid, dithiophosphoric acid, thiophosphoric acid, and phosphorotrithioic acid are thiophosphorus compounds with the formula OP(O)(=S), OP(S)(=S)O, OP(O)(=S)O, and OP(=S)(S)S, respectively. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 242.332 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 8 |
| Complexity | 152 |
| Monoisotopic Mass | 242.056 |
| Exact Mass | 242.056 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| 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+ | 0.9651 |
| Human Intestinal Absorption | HIA+ | 0.9963 |
| Caco-2 Permeability | Caco2+ | 0.5262 |
| P-glycoprotein Substrate | Non-substrate | 0.8175 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7487 |
| Non-inhibitor | 0.8203 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9168 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5535 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8010 |
| CYP450 2D6 Substrate | Non-substrate | 0.8269 |
| CYP450 3A4 Substrate | Non-substrate | 0.6182 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8295 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7904 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9107 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7662 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8758 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7400 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7662 |
| Non-inhibitor | 0.8853 | |
| AMES Toxicity | Non AMES toxic | 0.9532 |
| Carcinogens | Carcinogens | 0.7112 |
| Fish Toxicity | High FHMT | 0.8257 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8999 |
| Honey Bee Toxicity | High HBT | 0.9327 |
| Biodegradation | Ready biodegradable | 0.5000 |
| Acute Oral Toxicity | I | 0.5388 |
| Carcinogenicity (Three-class) | Non-required | 0.5521 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0718 | LogS |
| Caco-2 Permeability | 1.1365 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.7159 | LD50, mol/kg |
| Fish Toxicity | 1.6887 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.2436 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ... | 0260010 | European Union | 0.02* | 01/09/2008 | |
| Beans (without pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap bean... | 0260020 | European Union | 0.02* | 01/09/2008 | |
| Peas (with pods) (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Moringa/drumstick tree pods, Pigeon peas,) | 0260030 | European Union | 0.02* | 01/09/2008 | |
| Peas (without pods) (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Moringa/drumstick tree pods, Pigeon peas,) | 0260040 | European Union | 0.02* | 01/09/2008 | |
| Lentils (Lupins/lupini beans, Lupins/lupini beans, Lupins/lupini beans, Lupins/lupini beans,) | 0260050 | European Union | 0.02* | 01/09/2008 | |
| Others (2) | 0260990 | European Union | 0.02* | 01/09/2008 | |
| Stem vegetables | 0270000 | European Union | 0.02* | 01/09/2008 | |
| Asparagus (Hop sprouts,) | 0270010 | European Union | 0.02* | 01/09/2008 | |
| Cardoons (Borage stems,) | 0270020 | European Union | 0.02* | 01/09/2008 | |
| Celeries | 0270030 | European Union | 0.02* | 01/09/2008 | |
| Florence fennels | 0270040 | European Union | 0.02* | 01/09/2008 | |
| Globe artichokes (Banana flowers,) | 0270050 | European Union | 0.02* | 01/09/2008 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous determination of pesticide residues and antioxidants in blended oil using a liquid-liquid extraction combined with dispersive solid phase extraction method. | Food Chem | 2017 Aug 15 | 28372183 |
| Polycyclic aromatic hydrocarbons and pesticides in milk powder. | J Dairy Res | 2016 May | 27210498 |
| Novel restricted access materials combined to molecularly imprinted polymers for selective solid-phase extraction of organophosphorus pesticides from honey. | Food Chem | 2015 Nov 15 | 25977034 |
| Accelerated biodegradation of selected nematicides in tropical crop soils fromCosta Rica. | Environ Sci Pollut Res Int | 2015 Jan | 25135169 |
| Multiresidue method for the quantitation of 20 pesticides in aquatic products. | Anal Bioanal Chem | 2015 Dec | 26466578 |
| Organophosphorus insecticides in honey, pollen and bees (Apis mellifera L.) and their potential hazard to bee colonies in Egypt. | Ecotoxicol Environ Saf | 2015 Apr | 25574845 |
| Pesticide residues in market foods in Shaanxi Province of China in 2010. | Food Chem | 2013 Jun 1 | 23411338 |
| Pesticide residue analysis in cereal-based baby foods using multi-walled carbonnanotubes dispersive solid-phase extraction. | Anal Bioanal Chem | 2012 Jul | 22623047 |
| Pesticide analysis in toasted barley and chickpea flours. | J Sep Sci | 2012 Jan | 25940740 |
| Monitoring and risk assessment of pesticides in fresh omija (Schizandra chinensisBaillon) fruit and juice. | Food Chem Toxicol | 2012 Feb | 22079148 |
| Multi-walled carbon nanotubes as efficient solid-phase extraction materials oforganophosphorus pesticides from apple, grape, orange and pineapple fruit juices. | J Chromatogr A | 2008 Nov 21 | 18849040 |
| Application of a single-drop microextraction for the analysis of organophosphoruspesticides in juice. | J Chromatogr A | 2006 May 12 | 16569410 |
| Determination of pesticides by solid phase extraction followed by gaschromatography with nitrogen-phosphorous detection in natural water andcomparison with solvent drop microextraction. | Anal Bioanal Chem | 2006 Feb | 16402179 |
| Determination of organophosphorus pesticides in wheat flour by supercriticalfluid extraction and gas chromatography with nitrogen-phosphorus detection. | J Chromatogr A | 1998 Oct 16 | 9818429 |
| Selective, solid-matrix dispersion extraction of organophosphate pesticideresidues from milk. | J Chromatogr A | 1996 Nov 22 | 8997741 |
Targets
- 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
- Mechanism of Action:
- Ethoprop inhibits acetylcholinesterase. This results in the accumulation of acetylcholine in the nerve synapses, causing overstimulation of the nervous system.
References
- International Programme on Chemical Safety (IPCS) INCHEM (1996). Pesticide Document for Ethoprop. : http://www.inchem.org/documents/pds/pds/pest70_e.htm
- 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:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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:
- 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:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 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 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
- Gene Name:
- CYP2D6
- Uniprot ID:
- P10635
- Molecular Weight:
- 55768.94 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 ]