1-ethyl-6-fluoro-4-oxo-7-(3-oxopiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 176031
• Molecular Formular: C16H16FN3O4
• Molecular Mass: 333.3143432
• Monoisotopic Mass: 333.11248423
• SMILES: c1c(c(cc2c1n(cc(c2=O)C(=O)O)CC)F)N1CC(=O)NCC1
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1cc(N1CCNC(=O)C1)c(c2)F
• InChI: InChI=1S/C16H16FN3O4/c1-2-19-7-10(16(23)24)15(22)9-5-11(17)13(6-12(9)19)20-4-3-18-14(21)8-20/h5-7H,2-4,8H2,1H3,(H,18,21)(H,23,24)
• InChIKey: OIOFPHGTOUDKAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-6-fluoro-4-oxo-7-(3-oxopiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-ethyl-6-fluoro-4-oxo-7-(3-oxopiperazin-1-yl)quinoline-3-carboxylic acid
• Synonyms: 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-quinolinecarboxylic Acid; Oxonorfloxacin; 4-Oxo Norfloxacin

Database IDs

• CAS Number: 74011-42-0
• PubChem SID: 164231941
• PubChem CID: 130830

CALCULATED PROPERTIES

• Acid pKa: 6.1027126
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.607101
• LogD (pH = 7.4): -0.6122694
• Log P: 0.703851
• Molar Refractivity: 85.5559 cm^3
• Polarizability: 30.926016 Å^3
• Polar Surface Area: 89.95 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Light Beige Solid
• Melting Point: 316-319°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O858300

A metabolite of Norfloxacin (N681000).

REFERENCES

• Sanderson, H., et al.: Toxicol. Lett., 144, 383 (1984)
• Huschek, G., et al.: Environ. Toxicol., 19, 226 (1984)
• Montay, G., et al.: Antimicrob. Agents Chemother., 25, 463 (1984)