Ametryn
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Basic Info
| Common Name | Ametryn(F05026) |
| 2D Structure | |
| Description | Ametryn, a member of the Triazine chemical family, is a herbicide which inhibits photosynthesis and other enzymatic processes. It is used to control broadleaf weeds and annual grasses in pineapple, sugarcane and bananas. It is used on corn and potato crops for general weed control. It is also used as a vine desiccant on dry beans and potatoes. The EPA classifies it as Toxicity Class III, slightly toxic. Symptoms of acute exposure to high doses include nausea, vomiting, diarrhea, muscle weakness, and salivation. |
| FRCD ID | F05026 |
| CAS Number | 834-12-8 |
| PubChem CID | 13263 |
| Formula | C9H17N5S |
| IUPAC Name | 4-N-ethyl-6-methylsulfanyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine |
| InChI Key | RQVYBGPQFYCBGX-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H17N5S/c1-5-10-7-12-8(11-6(2)3)14-9(13-7)15-4/h6H,5H2,1-4H3,(H2,10,11,12,13,14) |
| Canonical SMILES | CCNC1=NC(=NC(=N1)SC)NC(C)C |
| Isomeric SMILES | CCNC1=NC(=NC(=N1)SC)NC(C)C |
| Synonyms |
Ametryn
834-12-8
AMETRYNE
Gesapax
Ametrex
Evik
Cemerin
Ametrine
Crisatrine
Doruplant
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazines |
| Subclass | 1,3,5-triazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Methylthio-s-triazines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Methylthio-s-triazine - 2,4-diamine-s-triazine - Alkyl-2-thio-s-triazine - Aryl thioether - Amino-1,3,5-triazine - Aminotriazine - Secondary aliphatic/aromatic amine - Alkylarylthioether - N-aliphatic s-triazine - Heteroaromatic compound - Azacycle - Sulfenyl compound - Thioether - Secondary amine - Amine - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as methylthio-s-triazines. These are aromatic compounds containing a 1,3,5-triazine ring that is substituted at the 2-position with a methylthio group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 227.33 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Complexity | 178 |
| Monoisotopic Mass | 227.12 |
| Exact Mass | 227.12 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.8018 |
| Human Intestinal Absorption | HIA+ | 0.8794 |
| Caco-2 Permeability | Caco2- | 0.5175 |
| P-glycoprotein Substrate | Non-substrate | 0.6744 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7869 |
| Non-inhibitor | 0.8166 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7862 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5251 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8601 |
| CYP450 2D6 Substrate | Non-substrate | 0.7535 |
| CYP450 3A4 Substrate | Non-substrate | 0.6841 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7864 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6403 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8580 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7931 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8740 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5058 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9631 |
| Non-inhibitor | 0.8124 | |
| AMES Toxicity | Non AMES toxic | 0.8415 |
| Carcinogens | Non-carcinogens | 0.8907 |
| Fish Toxicity | Low FHMT | 0.6509 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9004 |
| Honey Bee Toxicity | Low HBT | 0.6349 |
| Biodegradation | Not ready biodegradable | 0.9921 |
| Acute Oral Toxicity | III | 0.8378 |
| Carcinogenicity (Three-class) | Warning | 0.3969 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2648 | LogS |
| Caco-2 Permeability | 1.4173 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1872 | LD50, mol/kg |
| Fish Toxicity | 2.1951 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3723 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Enhanced degradation of prometryn and other s-triazine herbicides in purecultures and wastewater by polyvinyl alcohol-sodium alginate immobilizedLeucobacter sp. JW-1. | Sci Total Environ | 2018 Feb 15 | 28963898 |
| Comprehensive analysis of degradation and accumulation of ametryn in soils and inwheat, maize, ryegrass and alfalfa plants. | Ecotoxicol Environ Saf | 2017 Jun | 28279883 |
| Validation and assessment of matrix effect and uncertainty of a gaschromatography coupled to mass spectrometry method for pesticides in papaya andavocado samples. | J Food Drug Anal | 2017 Jul | 28911635 |
| Novel hydrolytic de-methylthiolation of the s-triazine herbicide prometryn byLeucobacter sp. JW-1. | Sci Total Environ | 2017 Feb 1 | 27866738 |
| Simultaneous removal of structurally different pesticides in a biomixture:Detoxification and effect of oxytetracycline. | Chemosphere | 2017 Feb | 27898329 |
| Spatial and Temporal Variability in Pesticide Exposure Downstream of a HeavilyIrrigated Cropping Area: Application of Different Monitoring Techniques. | J Agric Food Chem | 2016 May 25 | 26755130 |
| Analysis of banned veterinary drugs and herbicide residues in shellfish by liquid chromatography-tandem mass spectrometry (LC/MS/MS) and gas chromatography-tandem mass spectrometry (GC/MS/MS). | Mar Pollut Bull | 2016 Dec 15 | 27612928 |
| Development, validation and determination of multiclass pesticide residues incocoa beans using gas chromatography and liquid chromatography tandem massspectrometry. | Food Chem | 2015 Apr 1 | 25442595 |
| Supercritical fluid chromatography with photodiode array detection for pesticide analysis in papaya and avocado samples. | J Sep Sci | 2015 Apr | 25641906 |
| Banana peel as an adsorbent for removing atrazine and ametryne from waters. | J Agric Food Chem | 2013 Mar 13 | 23305150 |
| A modified QuEChERS method for the determination of some herbicides in yogurt andmilk by high performance liquid chromatography. | Talanta | 2013 Feb 15 | 23598011 |
| Extraction of eight triazine and phenylurea herbicides in yogurt by ionic liquid foaming-based solvent floatation. | J Chromatogr A | 2012 Jan 27 | 22218326 |
| A new selective liquid membrane extraction method for the determination of basic herbicides in agro-processed fruit juices and Ethiopian honey wine (Tej) samples. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2012 | 22324905 |
| Screening of agrochemicals in foodstuffs using low-temperature plasma (LTP)ambient ionization mass spectrometry. | Analyst | 2010 May | 20419245 |
| Desorption electrospray ionization mass spectrometry for trace analysis of agrochemicals in food. | Anal Chem | 2009 Jan 15 | 19090743 |
| Determination of triazine herbicides in fruits and vegetables using dispersivesolid-phase extraction coupled with LC-MS. | J Sep Sci | 2008 Apr | 18338404 |
| Biodegradation of methylthio-s-triazines by Rhodococcus sp. strain FJ1117YT, and production of the corresponding methylsulfinyl, methylsulfonyl and hydroxyanalogues. | Pest Manag Sci | 2007 Mar | 17245693 |
| Competitive sorption-desorption behavior of triazine herbicides with plantcuticular fractions. | J Agric Food Chem | 2006 Oct 4 | 17002450 |
| Influence of pH on pesticide sorption by soil containing wheat residue-derivedchar. | Environ Pollut | 2005 Apr | 15620591 |
| Pesticide contamination of the coastline of Martinique. | Mar Pollut Bull | 2005 | 16045943 |
Targets
- 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:
- 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:
- Transmembrane signaling receptor activity
- Specific Function:
- Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
- Gene Name:
- CD69
- Uniprot ID:
- Q07108
- Molecular Weight:
- 22559.25 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:
- Metal ion binding
- Specific Function:
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name:
- PDE4A
- Uniprot ID:
- P27815
- Molecular Weight:
- 98142.155 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 d 24-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.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 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:
- 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:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular Weight:
- 76447.99 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 ]
- 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 ]