(2S)-2-amino-3-{3-[2-(phosphonomethyl)phenyl]phenyl}propanoic acid

• ChemBase ID: 132838
• Molecular Formular: C16H18NO5P
• Molecular Mass: 335.291581
• Monoisotopic Mass: 335.09225931
• SMILES: c1ccc(c(c1)CP(=O)(O)O)c1cccc(c1)C[C@@H](C(=O)O)N
• Canonical SMILES: OC(=O)[C@H](Cc1cccc(c1)c1ccccc1CP(=O)(O)O)N
• InChI: InChI=1S/C16H18NO5P/c17-15(16(18)19)9-11-4-3-6-12(8-11)14-7-2-1-5-13(14)10-23(20,21)22/h1-8,15H,9-10,17H2,(H,18,19)(H2,20,21,22)/t15-/m0/s1
• InChIKey: NCEGJIHRQBRVJQ-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{3-[2-(phosphonomethyl)phenyl]phenyl}propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{3-[2-(phosphonomethyl)phenyl]phenyl}propanoic acid
• Synonyms: 3-[2′-Phosphonomethyl[1,1′-biphenyl]-3-yl]alanine; PMBA; Phenylbenzene ω-phosphono-α-amino acid

Database IDs

• MDL Number: MFCD00467903
• PubChem SID: 162227115; 24278002
• PubChem CID: 16219834

CALCULATED PROPERTIES

• Acid pKa: 1.6820922
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.60093
• LogD (pH = 7.4): -3.5238976
• Log P: -0.080972515
• Molar Refractivity: 86.1089 cm^3
• Polarizability: 34.834225 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: >10 mg/mL; DMSO: soluble0.2 mg/mL; H2O: soluble0.15 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GRIN1(2902)

DETAILS

Sigma Aldrich - P204

Biochem/physiol Actions
Selective strychnine-sensitive glycine receptor antagonist.
Legal Information
Made and sold under license from Nippon Chemiphar.