(2R)-3-methyl-2-[({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)amino]butanoic acid

• ChemBase ID: 166066
• Molecular Formular: C19H21N5O2
• Molecular Mass: 351.40234
• Monoisotopic Mass: 351.16952494
• SMILES: C(N[C@H](C(C)C)C(=O)O)c1ccc(cc1)c1ccccc1c1nnn[nH]1
• Canonical SMILES: CC([C@H](C(=O)O)NCc1ccc(cc1)c1ccccc1c1[nH]nnn1)C
• InChI: InChI=1S/C19H21N5O2/c1-12(2)17(19(25)26)20-11-13-7-9-14(10-8-13)15-5-3-4-6-16(15)18-21-23-24-22-18/h3-10,12,17,20H,11H2,1-2H3,(H,25,26)(H,21,22,23,24)/t17-/m1/s1
• InChIKey: NSXSCTCKWRSTHJ-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-methyl-2-[({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)amino]butanoic acid
• IUPAC Traditional name: (2R)-3-methyl-2-[({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)amino]butanoic acid
• Synonyms: N-[[2'-(2H-Tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine; N-[[2'-(1H-Tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine; Des(oxopentyl) Valsartan

Database IDs

• PubChem SID: 162260199
• PubChem CID: 71315539

CALCULATED PROPERTIES

• Acid pKa: 2.2669141
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.19122736
• LogD (pH = 7.4): -0.67776245
• Log P: 0.86096466
• Molar Refractivity: 111.3785 cm^3
• Polarizability: 39.700096 Å^3
• Polar Surface Area: 103.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 158-162°C (dec.)

DETAILS

Toronto Research Chemicals - D288510

An impurity in the synthesis of Valsartan (V095750).

REFERENCES

• Carini, D., et al.: J. Med. Chem., 34, 2525 (1991)
• Buhlmayer, P., et al.: Bioorg. Med. Chem. Lett., 4, 29 (1991)