7-[(2-aminopropyl)amino]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 166221
• Molecular Formular: C17H20FN3O4
• Molecular Mass: 349.3568032
• Monoisotopic Mass: 349.14378436
• SMILES: c1(c(c(cc2c1n(cc(c2=O)C(=O)O)C1CC1)F)NCC(N)C)OC
• Canonical SMILES: COc1c(NCC(N)C)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C17H20FN3O4/c1-8(19)6-20-13-12(18)5-10-14(16(13)25-2)21(9-3-4-9)7-11(15(10)22)17(23)24/h5,7-9,20H,3-4,6,19H2,1-2H3,(H,23,24)
• InChIKey: WMDWMECNQOEVCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(2-aminopropyl)amino]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 7-[(2-aminopropyl)amino]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• Synonyms: 7-[(2-Aminopropyl)amino]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic Acid; Desethylene Gatifloxacin

Database IDs

• CAS Number: 172426-87-8
• PubChem SID: 162260354
• PubChem CID: 46781127

CALCULATED PROPERTIES

• Acid pKa: 5.6647553
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.6349865
• LogD (pH = 7.4): -1.3472232
• Log P: -1.349141
• Molar Refractivity: 91.781 cm^3
• Polarizability: 33.70602 Å^3
• Polar Surface Area: 104.89 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289300

A metabolite of Gatifloxacin; a new quinolone with antibacterial activity.

REFERENCES

• Naber, C., et al.: Antimicrob. Agents Chemother., 45, 293 (2001)
• Herzler, M., et al.: J. Anal. Toxicol., 27, 233 (2001)
• Li, Y., et al.: J. Pharm. Biomed. Anal., 35, 1101 (2001)