7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 167427
• Molecular Formular: C20H21F2N3O3
• Molecular Mass: 389.3958464
• Monoisotopic Mass: 389.15509799
• SMILES: c1(c(cc2c(c1F)n(cc(c2=O)C(=O)O)C1CC1)F)N1C[C@H]2[C@@H](C1)NCCC2
• Canonical SMILES: Fc1cc2c(=O)c(cn(c2c(c1N1C[C@@H]2[C@H](C1)CCCN2)F)C1CC1)C(=O)O
• InChI: InChI=1S/C20H21F2N3O3/c21-14-6-12-17(25(11-3-4-11)8-13(19(12)26)20(27)28)16(22)18(14)24-7-10-2-1-5-23-15(10)9-24/h6,8,10-11,15,23H,1-5,7,9H2,(H,27,28)/t10-,15+/m0/s1
• InChIKey: WEXQOLCYKFJAJZ-ZUZCIYMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 7-[(4aS,7aS)-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic Acid; Moxifloxacin Imp. A (EP,BP); 8-Desmethoxy-8-fluoro Moxifloxacin

Database IDs

• CAS Number: 151213-15-9
• PubChem SID: 162261560
• PubChem CID: 10025461

CALCULATED PROPERTIES

• Acid pKa: 5.648573
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.47550982
• LogD (pH = 7.4): -0.19291821
• Log P: -0.1998701
• Molar Refractivity: 99.9772 cm^3
• Polarizability: 36.79832 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under inert atmosphere

DETAILS

Toronto Research Chemicals - D445850

Moxifloxacin (M745000) impurity A.

REFERENCES

• Martel, A., et al.: Drugs Fut., 22, 109 (1997)
• Tobin, C., et al.: J. Antimicrob. Chemother., 42, 278 (1997)