2-amino-5-phosphonopentanoic acid

• ChemBase ID: 103940
• Molecular Formular: C5H12NO5P
• Molecular Mass: 197.126241
• Monoisotopic Mass: 197.04530912
• SMILES: NC(CCCP(=O)(O)O)C(=O)O
• Canonical SMILES: OC(=O)C(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)
• InChIKey: VOROEQBFPPIACJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-phosphonopentanoic acid
• IUPAC Traditional name: 5-phosphono-DL-norvaline; 2-amino-5-phosphovaleric acid
• Synonyms: APV; DL-5-Phosphononorvaline; DL-2-Amino-5-phosphonovaleric acid; AP-5; DL-2-Amino-5-phosphono-valeric acid; 5-Phosphono-DL-norvaline; (±)-2-AMINO-5-PHOSPHONO-PENTANOIC ACID; DL-2-Amino-5-phosphonovaleric acid; DL-2-Amino-5-phosphonopentanoic acid; 5-膦酰基-DL-正缬氨酸; DL-5-膦酰正缬氨酸; DL-2-氨基-5-膦酰基缬草酸; DL-2-氨基-5-膦酰基缬草酸

Database IDs

• CAS Number: 76326-31-3
• MDL Number: MFCD00010515
• Beilstein Number: 2446389
• PubChem SID: 162091058; 24277950
• PubChem CID: 1216

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: 0.1 M NaOH: soluble4 mg/mL; 1 M NH4OH: soluble50 mg/mL, clear, colorless; H2O: soluble5.6 mg/mL; organic solvents: insoluble
• Apperance: white solid

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: rat ... Grik1(29559), Grin2a(24409), Grin2b(24410)

Product Information

• Purity: ≥98.0% (TLC); 98%
• Empirical Formula (Hill Notation): C5H12NO5P

DETAILS

MP Biomedicals - 02153639

Potent NMDA antagonist

Sigma Aldrich - A5282

Biochem/physiol Actions
Anticonvulsant; potent and selective NMDA receptor antagonist.
Caution
Hygroscopic

Sigma Aldrich - 09248

Biochem/physiol Actions
Anticonvulsant; potent and selective NMDA receptor antagonist.
Other Notes
Potent, selective antagonist for NMDA receptors1