(2S)-2-amino-4-(1H-imidazol-5-yl)butanoic acid

• ChemBase ID: 169934
• Molecular Formular: C7H11N3O2
• Molecular Mass: 169.18114
• Monoisotopic Mass: 169.08512661
• SMILES: n1cc([nH]c1)CC[C@H](N)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCc1cnc[nH]1)N
• InChI: InChI=1S/C7H11N3O2/c8-6(7(11)12)2-1-5-3-9-4-10-5/h3-4,6H,1-2,8H2,(H,9,10)(H,11,12)/t6-/m0/s1
• InChIKey: MSECZMWQBBVGEN-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(1H-imidazol-5-yl)butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-(3H-imidazol-4-yl)butanoic acid
• Synonyms: (αS)-α-Amino-1H-imidazole-5-butanoic Acid; (S)-α-Amino-1H-imidazole-4-butanoic Acid; L-Homohistidine

Database IDs

• CAS Number: 58501-47-6
• PubChem SID: 162264066
• PubChem CID: 12310464

CALCULATED PROPERTIES

• Acid pKa: 1.9923263
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.6204395
• LogD (pH = 7.4): -3.143038
• Log P: -3.1045148
• Molar Refractivity: 42.7036 cm^3
• Polarizability: 16.598787 Å^3
• Polar Surface Area: 92.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H597490

Used in the protein RNase S peptide binding.

REFERENCES

• Lee, Y., et al.: Bioorg. Med. Chem., 7, 1941 (1999)