7-[(4aS,7aS)-octahydro(5,5,7,7-2H4)-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 174837
• Molecular Formular: C21H25ClFN3O4
• Molecular Mass: 437.8923032
• Monoisotopic Mass: 437.1517622
• SMILES: c1(c(c(cc2c1n(cc(c2=O)C(=O)O)C1CC1)F)N1C[C@H]2[C@@H](C1)NCCC2)OC.Cl
• Canonical SMILES: COc1c(N2C[C@@H]3[C@H](C2)CCCN3)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1.Cl
• InChI: InChI=1S/C21H24FN3O4.ClH/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24;/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28);1H/t11-,16+;/m0./s1
• InChIKey: IDIIJJHBXUESQI-DFIJPDEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4aS,7aS)-octahydro(5,5,7,7-^2H₄)-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: 7-[(4aS,7aS)-hexahydro(5,5,7,7-^2H₄)pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid hydrochloride
• Synonyms: Proflox-d4; rac cis Moxifloxacin-d4 Hydrochloride; rac cis 1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic Acid-d4 Hydrochloride; BAY-12-8039-d4; Actira-d4; Avalox-d4

Database IDs

• PubChem SID: 164230747
• PubChem CID: 57347710

CALCULATED PROPERTIES

• Acid pKa: 5.6861296
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.79074246
• LogD (pH = 7.4): -0.4932184
• Log P: -0.49897495
• Molar Refractivity: 106.224 cm^3
• Polarizability: 39.59241 Å^3
• Polar Surface Area: 82.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 224-226°C (dec)

Safety Information

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

DETAILS

Toronto Research Chemicals - M745002

A labelled fluorinated quinolone antibacterial.

REFERENCES

• Woodcock, J.M., et al.: Antimicrob. Ag. Chemother., 41, 101 (1997)
• Stass, H., et al.: Antimicrob. Ag. Chemother., 42, 2060 (1998)