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

• ChemBase ID: 105116
• 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-/m1/s1
• InChIKey: VOROEQBFPPIACJ-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-5-phosphonopentanoic acid
• IUPAC Traditional name: (2R)-2-amino-5-phosphonopentanoic acid
• Synonyms: D-(-)-2-Amino-5-phosphono-valeric acid; D-AP5; D-(-)-2-AMINO-5-PHOSPHONOPENTANOIC ACID; D(-)-AP-5; D(-)-APV; D-2-Amino-5-phosphonovaleric acid; D(-)-2-Amino-5-phosphonopentanoic acid; AP5

Database IDs

• CAS Number: 76326-31-3; 79055-68-8
• MDL Number: MFCD00078839
• PubChem SID: 162091974; 24891311
• PubChem CID: 135342
• Chemspider ID: 119225
• Wikipedia Title: AP5

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

Physical Property

• Solubility: Ammonium hydroxide, 50 mg/mL in water
• Apperance: white solid
• Boiling Point: 482.1°C
• Density: 1.529 g/mL

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• 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: mouse ... Grin2a(14811)rat ... Grik1(29559), Grin2a(24409), Grin2b(24410), Grin2c(24411), Grin2d(24412)

Product Information

• Purity: 99%
• Optical Purity: optical purity: ≥90% (HPLC, Marfey′s reagent)

DETAILS

MP Biomedicals - 02158863

Purity: 99%
Active form of AP5, and a competitive NMDA antagonist.

Sigma Aldrich - A8054

Biochem/physiol Actions
Anticonvulsant; potent and selective N-methyl-D-aspartate (NMDA) receptor antagonist; active enantiomer of 2-amino-5-phosphonopentanoic acid.

REFERENCES

• Watkins, J.C., et al., Ann. Rev. Pharmacol. Toxicol. , 21 : 165 (1981).
• Hansen, J.J. and Krogsgaard-Larsen, P., Med. Res. Rev. , 10 : 55 (1990).