1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 166444
• Molecular Formular: C18H20FN3O4
• Molecular Mass: 361.3675032
• Monoisotopic Mass: 361.14378436
• SMILES: c1(c(c(cc2c1n(cc(c2=O)C(=O)O)C1CC1)F)N1CCNCC1)OC
• Canonical SMILES: COc1c(N2CCNCC2)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C18H20FN3O4/c1-26-17-14-11(8-13(19)15(17)21-6-4-20-5-7-21)16(23)12(18(24)25)9-22(14)10-2-3-10/h8-10,20H,2-7H2,1H3,(H,24,25)
• InChIKey: XJCSNIFKGXSDGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid; AM 1147; PD 135042; 3-Desmethyl Gatifloxacin

Database IDs

• CAS Number: 112811-57-1
• PubChem SID: 162260577
• PubChem CID: 465562

CALCULATED PROPERTIES

• Acid pKa: 5.6852956
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.2777916
• LogD (pH = 7.4): -0.98111665
• Log P: -0.9782923
• Molar Refractivity: 94.4026 cm^3
• Polarizability: 34.821396 Å^3
• Polar Surface Area: 82.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291655

3-Desmethyl Gatifloxacin is an impurity of Gatifloxacin (G250000).

REFERENCES

• Sriram, D., et al.: Bioorg. Med. Chem. Lett., 16, 2982 (2006)
• Nayyar, A., et al.: Bioorg. Med. Chem., 15, 626 (2006)
• Feng, L., et al.: Eur. J. Med. Chem., 45, 3407 (2006)