(2S)-7-fluoro-2-methyl-6-(N-{2-[N-(2H3)methylformamido]ethyl}formamido)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid

• ChemBase ID: 166223
• Molecular Formular: C18H18FN3O6
• Molecular Mass: 391.3504232
• Monoisotopic Mass: 391.11796353
• SMILES: C(CN(C)C=O)N(c1c2c3c(cc1F)c(=O)c(cn3[C@H](CO2)C)C(=O)O)C=O
• Canonical SMILES: O=CN(c1c(F)cc2c3c1OC[C@@H](n3cc(c2=O)C(=O)O)C)CCN(C=O)C
• InChI: InChI=1S/C18H18FN3O6/c1-10-7-28-17-14-11(16(25)12(18(26)27)6-22(10)14)5-13(19)15(17)21(9-24)4-3-20(2)8-23/h5-6,8-10H,3-4,7H2,1-2H3,(H,26,27)/t10-/m0/s1
• InChIKey: HTOKHJLTWLBPPN-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-7-fluoro-2-methyl-6-(N-{2-[N-(^2H₃)methylformamido]ethyl}formamido)-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)-7-fluoro-2-methyl-6-(N-{2-[N-(^2H₃)methylformamido]ethyl}formamido)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0^5,^1^3]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• Synonyms: (S)-9-Fluoro-10-[formyl[2-(formyl(methyl-d3)amino)ethyl]amino]-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid; N,N'-Desethylene-N,N'-diformyl Levofloxacin-d3

Database IDs

• PubChem SID: 162260356
• PubChem CID: 71315633

CALCULATED PROPERTIES

• Acid pKa: 5.6864896
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.36453217
• LogD (pH = 7.4): -1.8621417
• Log P: -0.14689593
• Molar Refractivity: 95.7454 cm^3
• Polarizability: 35.44712 Å^3
• Polar Surface Area: 107.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289332

Labelled Levofloxacin (L360000) impurity. A photodegradation product of Levofloxacin (L360000) in aqueous solution.

REFERENCES

• Yoshida, Y., et al.: Arzneim.-Forsch., 43, 601 (1993)