Glufosinate (CHEM000724)

Record Information
Version1.0
Creation Date2009-06-05 18:18:33 UTC
Update Date2026-05-14 17:45:10 UTC
Accession NumberCHEM000724
Identification
Common NameGlufosinate
ClassSmall Molecule
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.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Herbicide
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
PhosphinothricinChEBI
2-Amino-4-(hydroxymethylphosphinyl)butanoic acidKegg
2-Amino-4-(hydroxymethylphosphinyl)butanoateGenerator
Glufosinic acidGenerator
Glufosinate-ammoniumMeSH
Phosphinothricin, monoammonium saltMeSH
Phosphinothricin, monosodium salt, (S)-isomerMeSH
Phosphinothricin hydrochloride, (S)-isomerMeSH
Phosphinothricin, sodium salt, (S)-isomerMeSH
Phosphinothricin, barium (1:1) salt, (+-)-isomerMeSH
Phosphinothricin, monoammonium salt, (S)-isomerMeSH
Phosphinothricin, copper (+2) saltMeSH
Phosphinothricin, disodium salt, (S)-isomerMeSH
Phosphinothricin, monosodium saltMeSH
Phosphinothricin, dipotassium salt, (S)-isomerMeSH
Glufosinate ammoniumMeSH
Phosphinothricin, disodium saltMeSH
BastaMeSH
Phosphinothricin, monopotassium salt, (S)-isomerMeSH
2-Amino-4-methylphosphinobutyric acidMeSH
Ammonium glufosinateMeSH
Ammonium-DL-homoalanine-4-yl(methyl)-phosphinateMeSH
DL-GlufosinateMeSH
Phosphinothricin hydrochlorideMeSH
Phosphinothricin, (S)-isomerMeSH
Phosphinothricin, calcium (2:1) salt, (S)-isomerMeSH
Glufosinate-pMeSH
Phosphinothricin, diammonium saltMeSH
3-amino-3-Carboxypropylmethylphosphinic acidChEBI
DL-2-amino-4-(methylphosphino)Butanoic acidChEBI
3-amino-3-CarboxypropylmethylphosphinateGenerator
DL-2-amino-4-(methylphosphino)ButanoateGenerator
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 KeyIAJOBQBIJHVGMQ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
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
Predicted Properties
PropertyValueSource
Water Solubility46.3 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.66 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00000797
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlufosinate
Chemspider IDNot Available
ChEBI ID142851
PubChem Compound ID4794
Kegg Compound IDC05042
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References