2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid

• ChemBase ID: 172209
• Molecular Formular: C15H20O3
• Molecular Mass: 248.3175
• Monoisotopic Mass: 248.1412445
• SMILES: c1c(ccc(c1)C[C@@H]1[C@H](CCC1)O)C(C)C(=O)O
• Canonical SMILES: OC(=O)C(c1ccc(cc1)C[C@H]1CCC[C@@H]1O)C
• InChI: InChI=1S/C15H20O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13-14,16H,2-4,9H2,1H3,(H,17,18)/t10?,13-,14+/m1/s1
• InChIKey: SHAHPWSYJFYMRX-ADSMYIAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid
• IUPAC Traditional name: 2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid
• Synonyms: rel-4-[[(1R,2S)-2-Hydroxycyclopentyl]methyl]-α-methylbenzeneacetic Acid; rac trans-Loxoprofen Alcohol

Database IDs

• CAS Number: 371753-19-4
• PubChem SID: 164228119
• PubChem CID: 13148395

CALCULATED PROPERTIES

• Acid pKa: 4.2812343
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7180763
• LogD (pH = 7.4): -0.016371448
• Log P: 2.9602048
• Molar Refractivity: 69.7242 cm^3
• Polarizability: 27.221716 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L472915

The cis-alcohol metabolite of Loxoprofen (L472900).

REFERENCES

• Terada, A., et al.: J. Med. Chem., 27, 212 (1984)
• Sugimoto, M., et al.: Biochem. Pharmacol., 42, 2363 (1984)
• Riendeau, D., et al.: Bioorg. Med. Chem. Lett., 14, 1201 (1984)