(2S)-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 165576
• Molecular Formular: C18H21N3O4
• Molecular Mass: 343.37704
• Monoisotopic Mass: 343.15320617
• SMILES: c12c3c(=O)c(cn1[C@H](COc2c(cc3)N1CCN(CC1)C)C)C(=O)O
• Canonical SMILES: C[C@H]1COc2c3n1cc(C(=O)O)c(=O)c3ccc2N1CCN(CC1)C
• InChI: InChI=1S/C18H21N3O4/c1-11-10-25-17-14(20-7-5-19(2)6-8-20)4-3-12-15(17)21(11)9-13(16(12)22)18(23)24/h3-4,9,11H,5-8,10H2,1-2H3,(H,23,24)/t11-/m0/s1
• InChIKey: ANLIAKDHRADSBT-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• IUPAC Traditional name: (2S)-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• Synonyms: (3S)-2,3-Dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; Defluoro Levofloxacin

Database IDs

• CAS Number: 117620-85-6
• PubChem SID: 162259709
• PubChem CID: 23651701

CALCULATED PROPERTIES

• Acid pKa: 5.576947
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.02383336
• LogD (pH = 7.4): -0.4265919
• Log P: 0.13290048
• Molar Refractivity: 94.7195 cm^3
• Polarizability: 35.082195 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol.
• Apperance: Off-White to Yellow Solid
• Melting Point: 217-223°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D229020

Nonfluorinated analog of Levofloxacin (L360000).

REFERENCES

• Koga, H., et al.: J. Med. Chem., 23, 1358 (1980)
• Fujita, M., et al.: Chem. Pharm. Bull., 44, 987 (1980)
• Graul, A., et al.: Drugs Future, 24, 1324 (1980)
• Takahata, M., et al.: Antimicrob. Agents Chemother., 43, 1077 (1980)