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

• ChemBase ID: 169150
• Molecular Formular: C21H24FN3O4
• Molecular Mass: 401.4313632
• Monoisotopic Mass: 401.17508448
• SMILES: c1(c(cc2c(c1F)n(cc(c2=O)C(=O)O)C1CC1)OC)N1C[C@H]2[C@@H](C1)NCCC2
• Canonical SMILES: COc1cc2c(=O)c(cn(c2c(c1N1C[C@@H]2[C@H](C1)CCCN2)F)C1CC1)C(=O)O
• InChI: InChI=1S/C21H24FN3O4/c1-29-16-7-13-18(25(12-4-5-12)9-14(20(13)26)21(27)28)17(22)19(16)24-8-11-3-2-6-23-15(11)10-24/h7,9,11-12,15,23H,2-6,8,10H2,1H3,(H,27,28)/t11-,15+/m0/s1
• InChIKey: UGXNFVOVJRJWHB-XHDPSFHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-8-fluoro-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 7-[(4aS,7aS)-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-8-fluoro-6-methoxy-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-8-fluoro-1,4-dihydro-6-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic Acid Dihydrochloride; Moxifloxacin Imp. D (EP/BP) as diHCl salt; 8-Fluoro-6-methoxy Moxifloxacin Dihydrochloride

Database IDs

• CAS Number: 1029364-77-9
• PubChem SID: 162263282
• PubChem CID: 71316844

CALCULATED PROPERTIES

• Acid pKa: 5.6867146
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.79096335
• LogD (pH = 7.4): -0.4932045
• Log P: -0.49895015
• Molar Refractivity: 106.224 cm^3
• Polarizability: 39.59108 Å^3
• Polar Surface Area: 82.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow to Pale Gren Solid
• Melting Point: 100-104°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F593300

Moxifloxacin (M745000) impurity D.

REFERENCES

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