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Record Information
Version2.0
Creation Date2009-06-05 18:18:33 UTC
Update Date2014-12-24 20:22:51 UTC
Accession NumberT3D0812
Identification
Common NameGlufosinate
ClassSmall Molecule
DescriptionGlufosinate 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.
Compound Type
  • Amine
  • Herbicide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
( -)-phosphinothricin
(+-)-2-amino-4-(Hydroxymethylphosphinyl)butanoic acid
(+-)-2-amino-4-(Hydroxymethylphosphinyl)butanoic acid (9ci)
(2S)-2-amino-4-(Hydroxy-methylphosphoryl)butanoic acid
2-amino-4-(Hydroxy-methyl-phosphoryl)butanoic acid
2-amino-4-(Hydroxymethylphosphinyl)butanoic acid
2-amino-4-(Hydroxymethylphosphinyl)butyric acid
2-amino-4-Methylphosphinobutyric acid
2-amino-4-[Hydroxy(methyl)phosphoryl]butanoic acid
3-amino-3-Carboxypropylmethylphosphinic acid
4-(Hydroxy(methyl)phosphinoyl)-DL-homoalanine
Ammonium glufosinate
ammonium-DL-homoalanine-4-yl(methyl)-phosphinate
Basta
DL-2-amino-4-(Methylphosphino)butanoic acid
DL-Homoalanin-4-yl (methyl)phosphinic acid
DL-phosphinothricin
Glufosinate ammonium
Glufosinic acid
L-phophinothricin
NChemBio.2007.9-comp2
Phosphinothricin
Phosphinothricin hydrochloride
Chemical FormulaC5H12NO4P
Average Molecular Mass181.127 g/mol
Monoisotopic Mass181.050 g/mol
CAS Registry Number51276-47-2
IUPAC Name2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
Traditional Namebasta
SMILESCP(O)(=O)CCC(N)C(O)=O
InChI IdentifierInChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)
InChI KeyInChIKey=IAJOBQBIJHVGMQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point230°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility46.3 mg/mLALOGPS
logP-2.5ALOGPS
logP-3.8ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.66 m3·mol-1ChemAxon
Polarizability16.14 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-1900000000-c7a5f699586b196f06f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-4900000000-8ef3a4c2f4e0aa5fc416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-49e8c42d44e715d5a703View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-1dca53897016d68f3528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-8900000000-6d12f583f73568ac0f27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f0f80d3c8b20aaf97825View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityGlufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsSeizures; muscle weakness (post-status epileptic myopathy); convulsions; and even death. (1)
SymptomsNausea, vomiting, and diarrhea that is followed in 24h by impaired respiration. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02663
HMDB IDNot Available
PubChem Compound ID4794
ChEMBL IDCHEMBL450298
ChemSpider ID4630
KEGG IDC05042
UniProt IDNot Available
OMIM ID
ChEBI ID52136
BioCyc IDNot Available
CTD IDC003121
Stitch IDGlufosinate
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0812.pdf
General References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

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
References
  1. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.