(2S)-2-amino-5-phosphonopentanoic acid

• ChemBase ID: 105117
• Molecular Formular: C5H12NO5P
• Molecular Mass: 197.126241
• Monoisotopic Mass: 197.04530912
• SMILES: N[C@@H](CCCP(=O)(O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCCP(=O)(O)O)N
• InChI: InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m0/s1
• InChIKey: VOROEQBFPPIACJ-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-phosphonopentanoic acid
• IUPAC Traditional name: (2S)-2-amino-5-phosphonopentanoic acid
• Synonyms: APV; 5-Phosphononorvaline; L-AP5; L-(+)-2-AMINO-5-PHOSPHONO-PENTANOIC ACID

Database IDs

• CAS Number: 79055-67-7
• PubChem SID: 162093280
• PubChem CID: 1617110

CALCULATED PROPERTIES

• Acid pKa: 1.6680644
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.8741164
• LogD (pH = 7.4): -6.5600853
• Log P: -3.2310975
• Molar Refractivity: 40.5915 cm^3
• Polarizability: 16.462873 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Selective NMDA antagonist

Product Information

• Purity: 99%
• Application(s): Antiepileptic agent

DETAILS

MP Biomedicals - 02158864

(L-(+)-2-Amino-5-phosphono-
valeric acid; L-AP5)
Purity: 99%
Less active form than AP5.

REFERENCES

• Watkins, J.C., et al., Ann. Rev. Pharmacol. Toxicol., 21: 165 (1981).
• Hansen, J.J. and Krogsgaard-Larsen, P., Med. Res.
• Evans et al (1982) The effect of a series of w-phosphonic-a-carboxylic amino acids on electrically evoked and amino acid induced responses in isolated spinal cord preparations. Br.J.Pharmacol. 75 65.