Sethoxydim
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Basic Info
| Common Name | Sethoxydim(F05807) |
| 2D Structure | |
| FRCD ID | F05807 |
| CAS Number | 74051-80-2 |
| PubChem CID | 52923 |
| Formula | C17H29NO3S |
| IUPAC Name | 2-[1-(ethoxyamino)butylidene]-5-(2-ethylsulfanylpropyl)cyclohexane-1,3-dione |
| InChI Key | JEFHGYSGNIFAEY-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H29NO3S/c1-5-8-14(18-21-6-2)17-15(19)10-13(11-16(17)20)9-12(4)22-7-3/h12-13,18H,5-11H2,1-4H3 |
| Canonical SMILES | CCCC(=C1C(=O)CC(CC1=O)CC(C)SCC)NOCC |
| Isomeric SMILES | CCCC(=C1C(=O)CC(CC1=O)CC(C)SCC)NOCC |
| Synonyms |
Tritex-extra
SETHOXYDIM
74051-80-2
Cyethoxydim
Aljaden
Checkmate
Fervinal
Grasidim
Expand
Poast
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Vinylogous amides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Vinylogous amides |
| Alternative Parents | |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | Vinylogous amide - Ketone - Cyclic ketone - Thioether - Sulfenyl compound - Dialkylthioether - N-organohydroxylamine - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as vinylogous amides. These are organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 327.483 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 9 |
| Complexity | 400 |
| Monoisotopic Mass | 327.187 |
| Exact Mass | 327.187 |
| XLogP | 4.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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+ | 0.7757 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5529 |
| P-glycoprotein Substrate | Substrate | 0.5717 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8155 |
| Non-inhibitor | 0.8683 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7921 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6964 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8361 |
| CYP450 2D6 Substrate | Non-substrate | 0.7769 |
| CYP450 3A4 Substrate | Substrate | 0.5927 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5958 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7174 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8162 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6182 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5210 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6046 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.6188 |
| Non-inhibitor | 0.6632 | |
| AMES Toxicity | Non AMES toxic | 0.5803 |
| Carcinogens | Non-carcinogens | 0.7932 |
| Fish Toxicity | High FHMT | 0.9947 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9961 |
| Honey Bee Toxicity | High HBT | 0.7152 |
| Biodegradation | Not ready biodegradable | 0.8792 |
| Acute Oral Toxicity | III | 0.6245 |
| Carcinogenicity (Three-class) | Non-required | 0.5341 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4699 | LogS |
| Caco-2 Permeability | 1.1712 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4161 | LD50, mol/kg |
| Fish Toxicity | 1.1463 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5638 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Beans | Canada | 5mg/kg | |||
| Lentils | Canada | 30mg/kg | |||
| Lettuce | Canada | 1mg/kg | |||
| Other Poultry,Eggs | Japan | 1ppm | |||
| Chicken,Eggs | Japan | 1ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 1ppm | |||
| Chicken,Edible Offal | Japan | 1ppm | |||
| Other Poultry Animals,Kidney | Japan | 1ppm | |||
| Chicken,Kidney | Japan | 1ppm | |||
| Other Poultry Animals,Liver | Japan | 0.9ppm | |||
| Chicken,Liver | Japan | 0.9ppm | |||
| Other Poultry Animals,Fat | Japan | 0.2ppm | |||
| Chicken,Fat | Japan | 0.2ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.2ppm | |||
| Chicken,Muscle | Japan | 0.2ppm | |||
| Milk | Japan | 0.3ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.5ppm | |||
| Pig,Edible Offal | Japan | 0.5ppm | |||
| Cattle,Edible Offal | Japan | 0.5ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.5ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Photochemical behavior of sethoxydim in the presence of vegetable oils. | J Agric Food Chem | 2014 Jul 9 | 24932839 |
| Pleiotropic effects of herbicide-resistance genes on crop yield: a review. | Pest Manag Sci | 2013 Aug | 23457026 |
| Effects of herbicides on Behr's metalmark butterfly, a surrogate species for the endangered butterfly, Lange's metalmark. | Environ Pollut | 2012 May | 22310058 |
| LC/MS analysis of cyclohexanedione oxime herbicides in water. | J Agric Food Chem | 2000 Jul | 10898624 |
| Inhibition of ACCase220 and ACCase240 isozymes from sethoxydim-resistant and-susceptible maize hybrids. | J Agric Food Chem | 1999 Jan | 10563889 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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:
- 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:
- 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:
- 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:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]