1-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium-1-olate

• ChemBase ID: 164783
• Molecular Formular: C17H18FN3O4
• Molecular Mass: 347.3409232
• Monoisotopic Mass: 347.12813429
• SMILES: c1(c(cc2c(c1)n(cc(c2=O)C(=O)O)C1CC1)F)[N+]1(CCNCC1)[O-]
• Canonical SMILES: Fc1cc2c(cc1[N+]1([O-])CCNCC1)n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C17H18FN3O4/c18-13-7-11-14(8-15(13)21(25)5-3-19-4-6-21)20(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)
• InChIKey: RJFMBBVUVUPLHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium-1-olate
• IUPAC Traditional name: 1-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxoquinolin-7-yl)piperazin-1-ium-1-olate
• Synonyms: 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(1-oxido-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid; Ciprofloxacin N-Oxide

Database IDs

• CAS Number: 860033-22-3
• PubChem SID: 162258918
• PubChem CID: 71314873

CALCULATED PROPERTIES

• Acid pKa: 5.2545085
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -5.5121965
• LogD (pH = 7.4): -5.568129
• Log P: -5.403069
• Molar Refractivity: 98.8783 cm^3
• Polarizability: 32.827118 Å^3
• Polar Surface Area: 96.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C482520

A metabolite of Ciprofloxacin (C482500).

REFERENCES

• Seto, Y., et al.: J. Biol. Chem., 268, 9986 (1993)
• Golet, E., et al.: Anal. Chem., 73, 3632 (1993)
• Feng, W., et al.: J. Pharm. Biomed. Anal., 25, 545 (1993)