(2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid; (2S)-2,6-diaminohexanoic acid

• ChemBase ID: 171495
• Molecular Formular: C19H32N2O4
• Molecular Mass: 352.46838
• Monoisotopic Mass: 352.23620751
• SMILES: c1cc(ccc1CC(C)C)[C@@H](C)C(=O)O.NCCCC[C@H](N)C(=O)O
• Canonical SMILES: CC(Cc1ccc(cc1)[C@H](C(=O)O)C)C.NCCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C13H18O2.C6H14N2O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;7-4-2-1-3-5(8)6(9)10/h4-7,9-10H,8H2,1-3H3,(H,14,15);5H,1-4,7-8H2,(H,9,10)/t10-;5-/m10/s1
• InChIKey: IHHXIUAEPKVVII-APFIOPMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid; (2S)-2,6-diaminohexanoic acid
• IUPAC Traditional name: (-)-ibuprofen; L-lysine
• Synonyms: (αR)-α-Methyl-4-(2-methylpropyl)benzeneacetic Acid L-Lysine; (R)-(-)-Ibuprofen (S)-(+)-Lysinate

Database IDs

• CAS Number: 157369-85-2
• PubChem SID: 164227405
• PubChem CID: 15009332

CALCULATED PROPERTIES

• Acid pKa: 4.851939
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.1079764
• LogD (pH = 7.4): 1.3373861
• Log P: 3.8435583
• Molar Refractivity: 60.7319 cm^3
• Polarizability: 23.648134 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 185-187°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I140020

A nonsteroidal anti-inflammatory drug (NSAID). Optically active, selective cyclooxygenase inhibitor (IC50=14.9uM). Inhibits PGH synthase-1 and PGH synthase-2 with comparable potency.

REFERENCES

• Busson, M., et al.: J. Int. Med Res., 14, 53 (1986)
• Meade, E.A., et al.: J. Biol. Chem., 268, 6610 (1986)
• Davies, N.M., et al.: Clin. Pharmacokinet., 34, 101 (1986)