1-cyclopropyl-7-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 166425
• Molecular Formular: C18H18FN3O3
• Molecular Mass: 343.3522232
• Monoisotopic Mass: 343.13321967
• SMILES: c12c(c(=O)c(cn1C1CC1)C(=O)O)cc(c(c2)N1C[C@@H]2NC[C@H]1C2)F
• Canonical SMILES: Fc1cc2c(cc1N1C[C@H]3C[C@@H]1CN3)n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C18H18FN3O3/c19-14-4-12-15(5-16(14)21-7-9-3-11(21)6-20-9)22(10-1-2-10)8-13(17(12)23)18(24)25/h4-5,8-11,20H,1-3,6-7H2,(H,24,25)/t9-,11-/m0/s1
• InChIKey: LHZDPJRHQVYKPA-ONGXEEELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-7-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-cyclopropyl-7-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-7-(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-yl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid; N-Desmethyl Danofloxacin

Database IDs

• CAS Number: 108461-04-7
• PubChem SID: 162260558
• PubChem CID: 14328920

CALCULATED PROPERTIES

• Acid pKa: 5.6976824
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.2030923
• LogD (pH = 7.4): -0.901101
• Log P: -0.9045759
• Molar Refractivity: 90.1762 cm^3
• Polarizability: 33.3837 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291585

A metabolite of Danofloxacin.

REFERENCES

• Kiely, J.S., et al.: J. Med. Chem., 43, 656 (1991)