Carboxin
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Basic Info
| Common Name | Carboxin(F05394) |
| 2D Structure | |
| Description | Carboxin is a systemic fungicide used to control seed and seedling diseases (smut, rot, blight) on barley, beans, canola, corn, cotton, oats, onions, peanuts, rice, rye, safflower, sorghum, soybeans, triticale, and wheat. Carboxin has been shown to have low acute toxicity. Toxicity Categories, which range from I (most toxic) to IV (least toxic), were III for the oral route of exposure, IV for inhalation, and III for dermal. Carboxin is a slight eye irritant (Toxicity Category III), is not a skin irritant (Toxicity Category IV), and is negative for dermal sensitization. The mechanism of toxicity for carboxin has not been fully investigated; however the primary target organs appear to be the liver and kidney. In carcinogenicity studies in rats and mice, carboxin did not demonstrate any significant evidence of carcinogenic potential. |
| FRCD ID | F05394 |
| CAS Number | 5234-68-4 |
| PubChem CID | 21307 |
| Formula | C12H13NO2S |
| IUPAC Name | 6-methyl-N-phenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide |
| InChI Key | GYSSRZJIHXQEHQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14) |
| Canonical SMILES | CC1=C(SCCO1)C(=O)NC2=CC=CC=C2 |
| Isomeric SMILES | CC1=C(SCCO1)C(=O)NC2=CC=CC=C2 |
| Synonyms |
Carboxine
2-Methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
CARBOXIN
5234-68-4
Carbathiin
Vitavax
Kisvax
Oxatin
Vitavax 75W
DCMO
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Anilides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Anilides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Anilide - N-arylamide - 1,4-oxathiin - Vinylogous ester - Carboxamide group - Secondary carboxylic acid amide - Thioenolether - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 235.301 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 295 |
| Monoisotopic Mass | 235.067 |
| Exact Mass | 235.067 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.9764 |
| Human Intestinal Absorption | HIA+ | 0.9794 |
| Caco-2 Permeability | Caco2+ | 0.6035 |
| P-glycoprotein Substrate | Non-substrate | 0.6547 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5183 |
| Non-inhibitor | 0.9174 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7344 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6425 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6550 |
| CYP450 2D6 Substrate | Non-substrate | 0.7929 |
| CYP450 3A4 Substrate | Substrate | 0.5503 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6498 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5784 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8963 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7341 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8503 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8491 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9405 |
| Non-inhibitor | 0.8196 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8705 |
| Fish Toxicity | High FHMT | 0.6567 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9757 |
| Honey Bee Toxicity | Low HBT | 0.7260 |
| Biodegradation | Ready biodegradable | 0.6897 |
| Acute Oral Toxicity | II | 0.7329 |
| Carcinogenicity (Three-class) | Non-required | 0.4900 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.0777 | LogS |
| Caco-2 Permeability | 1.7841 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7064 | LD50, mol/kg |
| Fish Toxicity | 1.2391 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4823 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Other Poultry Animals,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry,Eggs | Japan | 0.01ppm | |||
| Chicken,Eggs | Japan | 0.01ppm | |||
| Chicken,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.1ppm | |||
| Chicken,Kidney | Japan | 0.1ppm | |||
| Other Poultry Animals,Liver | Japan | 0.1ppm | |||
| Chicken,Liver | Japan | 0.1ppm | |||
| Other Poultry Animals,Fat | Japan | 0.1ppm | |||
| Chicken,Fat | Japan | 0.1ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.1ppm | |||
| Chicken,Muscle | Japan | 0.1ppm | |||
| Milk | Japan | 0.01ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.1ppm | |||
| Pig,Edible Offal | Japan | 0.1ppm | |||
| Cattle,Edible Offal | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.1ppm | |||
| Pig,Kidney | Japan | 0.1ppm | |||
| Cattle,Kidney | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.1ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Studies on the mechanism of synthesis of ethyl acetate in Kluyveromyces marxianusDSM 5422. | Appl Microbiol Biotechnol | 2015 Feb | 25487884 |
| Earthworm ecotoxicological assessments of pesticides used to treat seeds under tropical conditions. | Chemosphere | 2013 Mar | 23261124 |
| Consumption of pesticide-treated wheat seed by a rural population in Malawi. | J Expo Sci Environ Epidemiol | 2012 Nov | 23047320 |
| Risk assessment studies on succinate dehydrogenase inhibitors, the new weapons inthe battle to control Septoria leaf blotch in wheat. | Mol Plant Pathol | 2012 Apr | 21933337 |
| Five carboxin-resistant mutants exhibited various responses to carboxin andrelated fungicides. | Biosci Biotechnol Biochem | 2011 | 21228470 |
| Identification of three mutant loci conferring carboxin-resistance anddevelopment of a novel transformation system in Aspergillus oryzae. | Fungal Genet Biol | 2009 Jan | 18992352 |
| Controlling food-contaminating fungi by targeting their antioxidativestress-response system with natural phenolic compounds. | Appl Microbiol Biotechnol | 2006 May | 16463173 |
| Phototransformation of carboxin in water. Toxicity of the pesticide and itssulfoxide to aquatic organisms. | J Agric Food Chem | 2004 Oct 6 | 15453691 |
| Flutolanil and carboxin resistance in Coprinus cinereus conferred by a mutationin the cytochrome b560 subunit of succinate dehydrogenase complex (Complex II). | Mol Genet Genomics | 2004 Oct | 15365819 |
| Phytotoxicity of pathogenic fungi and their mycotoxins to cereal seedling viability. | Acta Microbiol Immunol Hung | 2001 | 11233698 |
| Phytotoxicity of pathogenic fungi and their mycotoxins to cereal seedling viability. | Mycopathologia | 1999 Dec | 11189766 |
Targets
- General Function:
- Succinate dehydrogenase activity
- Specific Function:
- Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
- Gene Name:
- SDHA
- Uniprot ID:
- P31040
- Molecular Weight:
- 72690.975 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
- 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 ]
- 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:
- 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:
- 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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 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:
- 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 ]