(2S)-6-amino-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoic acid

• ChemBase ID: 163712
• Molecular Formular: C16H24N2O4
• Molecular Mass: 308.37276
• Monoisotopic Mass: 308.17360726
• SMILES: c1cccc(c1)CC[C@@H](N[C@@H](CCCCN)C(=O)O)C(=O)O
• Canonical SMILES: NCCCC[C@@H](C(=O)O)N[C@@H](C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C16H24N2O4/c17-11-5-4-8-13(15(19)20)18-14(16(21)22)10-9-12-6-2-1-3-7-12/h1-3,6-7,13-14,18H,4-5,8-11,17H2,(H,19,20)(H,21,22)/t13-,14+/m0/s1
• InChIKey: CJPMLWRZFHGSOZ-UONOGXRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoic acid
• IUPAC Traditional name: (2S)-6-amino-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoic acid
• Synonyms: [S-(R*,R*)]-α-[(5-Amino-1-carboxypentyl)amino]benzenebutanoic Acid; CPP-Lysine; N2-(S)-1-Carboxy-3-phenylpropyl-L-lysine

Database IDs

• CAS Number: 138247-43-5
• PubChem SID: 162257847
• PubChem CID: 71314526

CALCULATED PROPERTIES

• Acid pKa: 3.0811124
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.8576188
• LogD (pH = 7.4): -2.8711383
• Log P: -2.8537169
• Molar Refractivity: 82.3826 cm^3
• Polarizability: 32.832077 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 155-157°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C181225

Lisinopryl impurity.

REFERENCES

• Goa, K.L., et al.: Drugs, 52, 564 (1996)
• Cao, X.J., et al.: J. Pharm. Biomed. Anal., 39, 39 (1996)