Glufosinate
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Glufosinate(F03902) |
| 2D Structure | |
| Description | Glufosinate or its ammonium salt DL-phosphinothricin is an active ingredient in several nonselective systemic herbicides such as Basta, Rely, Finale, Ignite, Challenge, and Liberty. It interferes with the glutamine biosynthetic pathway that binds to the glutamate site of the enzyme. Glufosinate-treated plants die due to a buildup of ammonia and a cessation of photosynthesis due to lack of glutamine. |
| FRCD ID | F03902 |
| CAS Number | 51276-47-2 |
| PubChem CID | 4794 |
| Formula | C5H12NO4P |
| IUPAC Name | 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid |
| InChI Key | IAJOBQBIJHVGMQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10) |
| Canonical SMILES | CP(=O)(CCC(C(=O)O)N)O |
| Isomeric SMILES | CP(=O)(CCC(C(=O)O)N)O |
| Synonyms |
GLUFOSINATE
phosphinothricin
51276-47-2
DL-Phosphinothricin
Glufosinate [ISO]
Glufosinate [BSI:ISO]
3-Amino-3-carboxypropylmethylphosphinic acid
DL-2-Amino-4-(methylphosphino)butanoic acid
ammonium glufosinate
EINECS 257-102-5
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Alpha amino acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Alpha-amino acid - Fatty acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxygen compound - Primary amine - Organophosphorus compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Primary aliphatic amine - Carbonyl group - Amine - Organopnictogen compound - Organic oxide - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 181.128 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 193 |
| Monoisotopic Mass | 181.05 |
| Exact Mass | 181.05 |
| XLogP | -5 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.7674 |
| Human Intestinal Absorption | HIA- | 0.8332 |
| Caco-2 Permeability | Caco2- | 0.6847 |
| P-glycoprotein Substrate | Substrate | 0.5000 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9685 |
| Non-inhibitor | 1.0000 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9397 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5096 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7580 |
| CYP450 2D6 Substrate | Non-substrate | 0.8029 |
| CYP450 3A4 Substrate | Non-substrate | 0.5977 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6076 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9295 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9390 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9314 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8904 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 1.0000 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9677 |
| Non-inhibitor | 0.9474 | |
| AMES Toxicity | Non AMES toxic | 0.8624 |
| Carcinogens | Non-carcinogens | 0.9064 |
| Fish Toxicity | Low FHMT | 0.6066 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9737 |
| Honey Bee Toxicity | Low HBT | 0.7419 |
| Biodegradation | Ready biodegradable | 0.5245 |
| Acute Oral Toxicity | III | 0.6135 |
| Carcinogenicity (Three-class) | Non-required | 0.6489 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.8614 | LogS |
| Caco-2 Permeability | -0.6242 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5749 | LD50, mol/kg |
| Fish Toxicity | 2.1796 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.6012 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Validation and application of analytical method for glyphosate and glufosinate infoods by liquid chromatography-tandem mass spectrometry. | J Chromatogr A | 2018 May 11 | 29588098 |
| Development and evaluation of rapid screening detection methods for geneticallymodified crops using loop-mediated isothermal amplification. | Food Chem | 2018 Jun 30 | 29478558 |
| Sensitive and rapid determination of glyphosate, glufosinate, bialaphos andmetabolites by UPLC-MS/MS using a modified Quick Polar Pesticides Extractionmethod. | Forensic Sci Int | 2018 Feb | 29291496 |
| Optimization and Validation of a Residue Analysis Method for Glyphosate,Glufosinate, and Their Metabolites in Plant Matrixes by Liquid Chromatographywith Tandem Mass Spectrometry. | J AOAC Int | 2017 May 1 | 28300023 |
| Forward selection for multiple resistance across the non-selective glyphosate,glufosinate and oxyfluorfen herbicides in Lolium weed species. | Pest Manag Sci | 2017 May | 27447950 |
| Safety assessment of transgenic canola RF3 with bar and barstar gene onSprague-Dawley (SD) rats by 90-day feeding test. | Regul Toxicol Pharmacol | 2017 Dec | 29074276 |
| Development and Validation of Ion Chromatography-Tandem Mass Spectrometry-BasedMethod for the Multiresidue Determination of Polar Ionic Pesticides in Food. | J Agric Food Chem | 2017 Aug 30 | 28388055 |
| A temperature-tolerant multiplex elements and genes screening system forgenetically modified organisms based on dual priming oligonucleotide primers and capillary electrophoresis. | Food Chem | 2017 Aug 15 | 28372191 |
| Over-expression of fHbp in Arabdopsis for development of meningococcal serogroup B subunit vaccine. | Biotechnol J | 2016 Jul | 27119621 |
| Fixed-route monitoring and a comparative study of the occurrence ofherbicide-resistant oilseed rape (Brassica napus L.) along a Japanese roadside. | GM Crops Food | 2016 Jan 2 | 26838503 |
| Residue determination of glufosinate in plant origin foods using modified QuickPolar Pesticides (QuPPe) method and liquid chromatography coupled with tandemmass spectrometry. | Food Chem | 2016 Apr 15 | 26617010 |
| Resistance to glufosinate is proportional to phosphinothricin acetyltransferaseexpression and activity in LibertyLink(®) and WideStrike(®) cotton. | Planta | 2016 Apr | 26733464 |
| Perspectives on transgenic, herbicide-resistant crops in the United States almost20 years after introduction. | Pest Manag Sci | 2015 May | 25052888 |
| Microchip electrophoresis for fast and interference-free determination of traceamounts of glyphosate and glufosinate residues in agricultural products. | Methods Mol Biol | 2015 | 25673479 |
| Current state of herbicides in herbicide-resistant crops. | Pest Manag Sci | 2014 Sep | 24446395 |
| Rapid detection of pesticides not amenable to multi-residue methods by flowinjection-tandem mass spectrometry. | Anal Bioanal Chem | 2014 Nov | 24518902 |
| Genetic transformation of wheat via particle bombardment. | Methods Mol Biol | 2014 | 24243206 |
| Fast and interference-free determination of glyphosate and glufosinate residuesthrough electrophoresis in disposable microfluidic chips. | J Chromatogr A | 2013 Mar 15 | 23398994 |
| Pleiotropic effects of herbicide-resistance genes on crop yield: a review. | Pest Manag Sci | 2013 Aug | 23457026 |
| Transgenic plants: from first successes to future applications. | Int J Dev Biol | 2013 | 24166429 |
Targets
- General Function:
- Manganese ion binding
- Specific Function:
- This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). Essential for proliferation of fetal skin fibroblasts.
- Gene Name:
- GLUL
- Uniprot ID:
- P15104
- Molecular Weight:
- 42064.15 Da
- Mechanism of Action:
- Glufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants.
References
- Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.