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

• ChemBase ID: 166658
• Molecular Formular: C16H18FN3O4
• Molecular Mass: 335.3302232
• Monoisotopic Mass: 335.12813429
• SMILES: c1(c(c(cc2c1n(cc(c2=O)C(=O)O)C1CC1)F)NCCN)OC
• Canonical SMILES: NCCNc1c(F)cc2c(c1OC)n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C16H18FN3O4/c1-24-15-12(19-5-4-18)11(17)6-9-13(15)20(8-2-3-8)7-10(14(9)21)16(22)23/h6-8,19H,2-5,18H2,1H3,(H,22,23)
• InChIKey: VRWBCRPZUUYZMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 172426-86-7
• PubChem SID: 162260791
• PubChem CID: 18448976

CALCULATED PROPERTIES

• Acid pKa: 5.6648073
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.0470545
• LogD (pH = 7.4): -1.759776
• Log P: -1.7663659
• Molar Refractivity: 87.3622 cm^3
• Polarizability: 31.88204 Å^3
• Polar Surface Area: 104.89 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); Methanol (Sparingly)
• Apperance: Pale Yellow Solid
• Melting Point: 180-182°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D297280

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)