Chlorethoxyfos
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Basic Info
| Common Name | Chlorethoxyfos(F05395) |
| 2D Structure | |
| Description | Chlorethoxyfos is an organophosphate acetylcholinesterase inhibitor used as an insecticide. Chlorethoxyfos can cause cholinesterase inhibition in humans; that is, it can overstimulate the nervous system causing nausea, dizziness, confusion, and at very high exposures (e.g, accidents or major spills), respiratory paralysis and death. |
| FRCD ID | F05395 |
| CAS Number | 54593-83-8 |
| PubChem CID | 91655 |
| Formula | C6H11Cl4O3PS |
| IUPAC Name | diethoxy-sulfanylidene-(1,2,2,2-tetrachloroethoxy)-$l^{5}-phosphane |
| InChI Key | XFDJMIHUAHSGKG-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H11Cl4O3PS/c1-3-11-14(15,12-4-2)13-5(7)6(8,9)10/h5H,3-4H2,1-2H3 |
| Canonical SMILES | CCOP(=S)(OCC)OC(C(Cl)(Cl)Cl)Cl |
| Isomeric SMILES | CCOP(=S)(OCC)OC(C(Cl)(Cl)Cl)Cl |
| Wikipedia | Chlorethoxyfos |
| Synonyms |
O,O-Diethyl O-(1,2,2,2-tetrachloroethyl) phosphorothioate
Chlorethoxyfos
Chlorethoxyphos
Chloroethoxyfos
54593-83-8
Fortress
Chlorethoxyfos [ANSI:ISO]
HSDB 7131
DPX 43898
BRN 2505303
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic thiophosphoric acids and derivatives |
| Subclass | Thiophosphoric acid esters |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Thiophosphate triesters |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Thiophosphate triester - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organochloride - Organohalogen compound - Alkyl halide - Alkyl chloride - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as thiophosphate triesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly three R-groups are organyl groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 335.985 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Complexity | 225 |
| Monoisotopic Mass | 333.892 |
| Exact Mass | 335.889 |
| XLogP | 4.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.9478 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5533 |
| P-glycoprotein Substrate | Non-substrate | 0.8710 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7330 |
| Non-inhibitor | 0.9553 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9297 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6985 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8026 |
| CYP450 2D6 Substrate | Non-substrate | 0.7953 |
| CYP450 3A4 Substrate | Non-substrate | 0.5987 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7791 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7610 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9064 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6417 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8035 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6897 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8973 |
| Non-inhibitor | 0.8828 | |
| AMES Toxicity | Non AMES toxic | 0.6629 |
| Carcinogens | Carcinogens | 0.8390 |
| Fish Toxicity | High FHMT | 0.9053 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9480 |
| Honey Bee Toxicity | High HBT | 0.9528 |
| Biodegradation | Not ready biodegradable | 0.9792 |
| Acute Oral Toxicity | I | 0.8442 |
| Carcinogenicity (Three-class) | Non-required | 0.6294 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8501 | LogS |
| Caco-2 Permeability | 0.6668 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.1915 | LD50, mol/kg |
| Fish Toxicity | 1.9214 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0362 | pIGC50, ug/L |
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:
- 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:
- 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:
- 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:
- Steroid binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 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:
- 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 ]