(2R)-2-chloro-3-(1H-imidazol-4-yl)propanoic acid

• ChemBase ID: 164338
• Molecular Formular: C6H7ClN2O2
• Molecular Mass: 174.58498
• Monoisotopic Mass: 174.01960515
• SMILES: [nH]1cc(nc1)C[C@@H](Cl)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](Cc1c[nH]cn1)Cl
• InChI: InChI=1S/C6H7ClN2O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1H2,(H,8,9)(H,10,11)/t5-/m1/s1
• InChIKey: JZLQYMHAXPPICX-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-chloro-3-(1H-imidazol-4-yl)propanoic acid
• IUPAC Traditional name: (2R)-2-chloro-3-(1H-imidazol-4-yl)propanoic acid
• Synonyms: (R)-α-Chloro-1H-imidazole-4-propanoic Acid; (R)-2-Chloro-3-(imidazol-5-yl)propionic Acid; (R)-(+)-2-Chloro-3-[4(5)-imidazolyl]propionic Acid

Database IDs

• CAS Number: 17561-27-2
• PubChem SID: 162258473
• PubChem CID: 29975992

CALCULATED PROPERTIES

• Acid pKa: 3.4539375
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.86225706
• LogD (pH = 7.4): -1.715855
• Log P: -0.8321932
• Molar Refractivity: 38.8868 cm^3
• Polarizability: 15.167289 Å^3
• Polar Surface Area: 65.98 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C366871

A substituted imidazoles as TAFIa inhibitors.

REFERENCES

• Levine, R.J., et al.: Biochem. Pharmacol., 14, 139 (1965)
• Boffa, M., et al.: J. Biol. Chem., 4, 2127 (1998)