methyl (2S)-2-chloro-3-(1H-imidazol-4-yl)propanoate

• ChemBase ID: 166057
• Molecular Formular: C7H9ClN2O2
• Molecular Mass: 188.61156
• Monoisotopic Mass: 188.03525522
• SMILES: [nH]1cc(nc1)C[C@@H](C(=O)OC)Cl
• Canonical SMILES: COC(=O)[C@H](Cc1c[nH]cn1)Cl
• InChI: InChI=1S/C7H9ClN2O2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6H,2H2,1H3,(H,9,10)/t6-/m0/s1
• InChIKey: JIPJJONLBKXGDE-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-chloro-3-(1H-imidazol-4-yl)propanoate
• IUPAC Traditional name: methyl (2S)-2-chloro-3-(1H-imidazol-4-yl)propanoate
• Synonyms: (S)-α-Chloro-1H-imidazole-4-propanoic Acid Methyl Ester; Desamino (αS)-Chloro Histidine Methyl Ester

Database IDs

• CAS Number: 64407-67-6
• PubChem SID: 162260190
• PubChem CID: 12355783

CALCULATED PROPERTIES

• Acid pKa: 13.092684
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.18651234
• LogD (pH = 7.4): 0.54592717
• Log P: 0.5963362
• Molar Refractivity: 43.6559 cm^3
• Polarizability: 17.21224 Å^3
• Polar Surface Area: 54.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - D288465

Histidine derivative.

REFERENCES

• Dahl, K., et al.: Bioorg. Chem., 10, 329 (1981)