Structure via PubChem · Public domain (PubChem)
bilanafos
Sign in to saveAlso known as gamma-(Hydroxymethylphosphinyl)-L-alpha-aminobutyryl-L-alanyl-L-alanine, 2-Amino-4-(methylphosphino)butyrylalanylalanine, L-phosphinothricyl-L-alanyl-L-alanine, (2S)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyryl-L-alanyl-L-alanine, (2S)-2-amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-alanine, PTT, Phosphinothricylalanylalanine, Antibiotic SF 1293
Bialaphos is a natural herbicide produced by the bacteria Streptomyces hygroscopicus and Streptomyces viridochromogenes. It is also known by the ISO common name bilanafos. Bialaphos is a protoxin and nontoxic as is. When it is metabolized by a plant, the glutamic acid analog glufosinate is released which inhibits glutamine synthetase. This results in the accumulation of ammonium and disruption of primary metabolism.
Chemical data
- Formula
- C11H22N3O6P
- Molecular weight
- 323.28 g/mol
- IUPAC name
- (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoic acid
- SMILES
- C[C@@H](C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](CCP(=O)(C)O)N
- InChIKey
- GINJFDRNADDBIN-FXQIFTODSA-N
- XLogP
- -4.9
- Polar surface area
- 159 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 323.124622
- Has use
- herbicide
Show 4 more facts
- chemical formula
- C₁₁H₂₂N₃O₆P
- isomeric SMILES
- C[C@@H](C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](CCP(=O)(C)O)N
- canonical SMILES
- CC(C(=O)NC(C)C(=O)O)NC(=O)C(CCP(=O)(C)O)N
- subject has role
- antibiotic
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
{{chembox | Watchedfields = changed | verifiedrevid = | Reference = | ImageFile = Bialaphos.svg | SystematicName = (2S)-2-[(2S)-2-{(2S)-2-Amino-4-[hydroxy(methylphosphonoyl)]butanamido}propanamido]propanoic acid | OtherNames = L-Alanyl-L-alanyl-phosphinothricin |Section1= |Section2= |Section3= }}
Bialaphos is a natural herbicide produced by the bacteria Streptomyces hygroscopicus and Streptomyces viridochromogenes. It is also known by the ISO common name bilanafos. Bialaphos is a protoxin and nontoxic as is. When it is metabolized by a plant, the glutamic acid analog glufosinate is released which inhibits glutamine synthetase. This results in the accumulation of ammonium and disruption of primary metabolism.
Excerpted from Wikipedia’s “bilanafos” article, available under the CC BY-SA 4.0 licence.