Dicrotophos
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Basic Info
| Common Name | Dicrotophos(F05057) |
| 2D Structure | |
| Description | Dicrotophos is an organophosphate acetylcholinesterase inhibitor used as an insecticide. Some common brand names for dicrotophos include Bidrin, Carbicron, Diapadrin, Dicron and Ektafos. |
| FRCD ID | F05057 |
| CAS Number | 141-66-2 |
| PubChem CID | 5371560 |
| Formula | C8H16NO5P |
| IUPAC Name | [(E)-4-(dimethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate |
| InChI Key | VEENJGZXVHKXNB-VOTSOKGWSA-N |
| InChI | InChI=1S/C8H16NO5P/c1-7(6-8(10)9(2)3)14-15(11,12-4)13-5/h6H,1-5H3/b7-6+ |
| Canonical SMILES | CC(=CC(=O)N(C)C)OP(=O)(OC)OC |
| Isomeric SMILES | C/C(=C\C(=O)N(C)C)/OP(=O)(OC)OC |
| Synonyms |
DICROTOPHOS
Bidrin
Carbicron
Carbomicron
Diapadrin
Karbicron
Oleobidrin
Ektafos
141-66-2
Dicrotofos
|
| Classifies |
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 - N-acyl-amine - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - 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 | 237.192 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Complexity | 291 |
| Monoisotopic Mass | 237.077 |
| Exact Mass | 237.077 |
| XLogP | 0 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.9533 |
| Human Intestinal Absorption | HIA+ | 0.9249 |
| Caco-2 Permeability | Caco2- | 0.5221 |
| P-glycoprotein Substrate | Non-substrate | 0.8249 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6201 |
| Non-inhibitor | 0.9259 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9505 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7696 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8254 |
| CYP450 2D6 Substrate | Non-substrate | 0.8305 |
| CYP450 3A4 Substrate | Substrate | 0.5688 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8048 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8037 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9281 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7479 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8067 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9285 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9517 |
| Non-inhibitor | 0.9441 | |
| AMES Toxicity | AMES toxic | 0.8143 |
| Carcinogens | Carcinogens | 0.6839 |
| Fish Toxicity | Low FHMT | 0.5587 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6365 |
| Honey Bee Toxicity | High HBT | 0.8798 |
| Biodegradation | Ready biodegradable | 0.7555 |
| Acute Oral Toxicity | I | 0.7735 |
| Carcinogenicity (Three-class) | Non-required | 0.4990 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.2437 | LogS |
| Caco-2 Permeability | 0.7045 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.2922 | LD50, mol/kg |
| Fish Toxicity | 1.1054 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3714 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Susceptibility of pest Nezara viridula (Heteroptera: Pentatomidae) and parasitoid Trichopoda pennipes (Diptera: Tachinidae) to selected insecticides. | J Econ Entomol | 2006 Jun | 16813294 |
| Comparison of susceptibility of pest Euschistus servus and predator Podisus maculiventris (Heteroptera: Pentatomidae) to selected insecticides. | J Econ Entomol | 2004 Jun | 15279256 |
Targets
- General Function:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 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:
- Serine-type endopeptidase inhibitor activity
- Specific Function:
- Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
- Gene Name:
- SERPINE1
- Uniprot ID:
- P05121
- Molecular Weight:
- 45059.695 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:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 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:
- Virus receptor activity
- Specific Function:
- Binds LDL, the major cholesterol-carrying lipoprotein of plasma, and transports it into cells by endocytosis. In order to be internalized, the receptor-ligand complexes must first cluster into clathrin-coated pits.(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes, but not through a direct interaction with viral proteins (PubMed:10535997, PubMed:12615904). Acts as a receptor for vesicular stomatitis virus (PubMed:23589850). In case of HIV-1 infection, may function as a receptor for extracellular Tat in neurons, mediating its internalization in uninfected cells (PubMed:11100124).
- Gene Name:
- LDLR
- Uniprot ID:
- P01130
- Molecular Weight:
- 95375.105 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 ]