(2R)-6,7-difluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 175812
• Molecular Formular: C13H9F2NO4
• Molecular Mass: 281.2116664
• Monoisotopic Mass: 281.04996421
• SMILES: Fc1c2c3c(cc1F)c(=O)c(cn3[C@@H](CO2)C)C(=O)O
• Canonical SMILES: OC(=O)c1cn2[C@H](C)COc3c2c(c1=O)cc(c3F)F
• InChI: InChI=1S/C13H9F2NO4/c1-5-4-20-12-9(15)8(14)2-6-10(12)16(5)3-7(11(6)17)13(18)19/h2-3,5H,4H2,1H3,(H,18,19)/t5-/m1/s1
• InChIKey: NVKWWNNJFKZNJO-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-6,7-difluoro-2-methyl-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: (2R)-6,7-difluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• Synonyms: (3R)-9,10-Difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; (R)-Ofloxacin Carboxylic Acid (Dextrofloxacin Difluoro Impurity)

Database IDs

• PubChem SID: 164231722
• PubChem CID: 688334

CALCULATED PROPERTIES

• Acid pKa: 5.5150814
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.4524573
• LogD (pH = 7.4): -0.13491902
• Log P: 1.7458881
• Molar Refractivity: 64.6736 cm^3
• Polarizability: 23.55114 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O245760

The R-enantiomer of Levofloxacin Carboxylic Acid (L360250); an impurity of Levofloxacin. The (S)-enantiomer is substantially the more active.

REFERENCES

• Liu, Bo; Y., et al.: Bioorg. Med. Chem., 13, 2451 (2005)
• Lalitha D., et al.: J. Pharm. Biomed. Anal., 50, 710 (2005)