2-amino-3-phosphonopropanoic acid

• ChemBase ID: 74883
• Molecular Formular: C3H8NO5P
• Molecular Mass: 169.073081
• Monoisotopic Mass: 169.01400899
• SMILES: P(=O)(O)(O)CC(N)C(=O)O
• Canonical SMILES: OC(=O)C(CP(=O)(O)O)N
• InChI: InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
• InChIKey: LBTABPSJONFLPO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-phosphonopropanoic acid
• IUPAC Traditional name: phosphonoalanine; 2-amino-3-phosphonopropanoic acid
• Synonyms: D,L-2-Amino-3-phosphonopropionic acid; 3-Phosphono-DL-alanine; AP-3; DL-2-Amino-3-phosphonopropionic acid; Aminophosphonopropionic acid

Database IDs

• CAS Number: 76483-21-1; 20263-06-3
• MDL Number: MFCD00014350
• PubChem SID: 162039801; 24277949
• PubChem CID: 3857

CALCULATED PROPERTIES

• Acid pKa: 1.396297
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -6.630927
• LogD (pH = 7.4): -7.2072453
• Log P: -3.8259072
• Molar Refractivity: 31.0815 cm^3
• Polarizability: 12.89791 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 227-229 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)
• Mechanism of Action: Phosphatase inhibitor

Product Information

• Application(s): Anticonvulsant

DETAILS

Sigma Aldrich - A4910

Biochem/physiol Actions
Potent metabotropic glutamate receptor antagonist.

REFERENCES

• 207th American Chemical Society National Meeting, San Diego, California, March 13-17, 1994 Poster, MEDI 233, 16 March 1994