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

• ChemBase ID: 169935
• Molecular Formular: C7H11N3O2
• Molecular Mass: 169.18114
• Monoisotopic Mass: 169.08512661
• SMILES: c1(CCC(N)C(=O)O)[nH]cnc1
• Canonical SMILES: OC(=O)C(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)
• InChIKey: MSECZMWQBBVGEN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(1H-imidazol-5-yl)butanoic acid
• IUPAC Traditional name: 2-amino-4-(3H-imidazol-4-yl)butanoic acid
• Synonyms: α-Amino-1H-Imidazole-5-butanoic Acid; α-Aminoimidazole-4-butyric Acid; (+/-)-Homohistidine

Database IDs

• CAS Number: 5817-77-6
• PubChem SID: 162264067
• PubChem CID: 4153393

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

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >213°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H597500

Used for the study of histidine kinases as a support for solid phase synthesis.

REFERENCES

• Pirrung, M.C., et al.: J. Org. Chem., 65, 2229 (2000)