(2S)-2-amino-3-fluoro-2-(1H-imidazol-5-ylmethyl)propanoic acid; methane

• ChemBase ID: 169154
• Molecular Formular: C8H14FN3O2
• Molecular Mass: 203.2140632
• Monoisotopic Mass: 203.10700492
• SMILES: n1cc([nH]c1)CC(CF)(N)C(=O)O.C
• Canonical SMILES: NC(C(=O)O)(CF)Cc1cnc[nH]1.C
• InChI: InChI=1S/C7H10FN3O2.CH4/c8-3-7(9,6(12)13)1-5-2-10-4-11-5;/h2,4H,1,3,9H2,(H,10,11)(H,12,13);1H4/t7-;/m1./s1
• InChIKey: DVLACWJDZOHEHC-OGFXRTJISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-fluoro-2-(1H-imidazol-5-ylmethyl)propanoic acid; methane
• IUPAC Traditional name: (2S)-2-amino-3-fluoro-2-(3H-imidazol-4-ylmethyl)propanoic acid; methane
• Synonyms: α-Fluoromethylhistidine Dihydrochloride; α-(Fluoromethyl)-L-histidine Dihydrochloride; (S)-(+)-α-Fluoromethylhistidine Dihydrochloride (~90%)

Database IDs

• PubChem SID: 162263286
• PubChem CID: 71316846

CALCULATED PROPERTIES

• Acid pKa: 1.9015868
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.8149486
• LogD (pH = 7.4): -3.2560885
• Log P: -3.292659
• Molar Refractivity: 42.6239 cm^3
• Polarizability: 16.420763 Å^3
• Polar Surface Area: 92.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: >191°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F593660

A histidine carboxylase inhibitor.

REFERENCES

• Kirsch, J., et al.: J. Mol. Biol., 174, 497 (1984)
• Hayashi, H., et al.: J. Biol. Chem., 261, 11003 (1984)
• Okamoto, A., et al.: J. Biochem., 116, 95 (1984)
• Sakai, N., et al.: Life Sci., 62, 989 (1984)