(2S,3S,4S,5R,6S)-6-[(2S)-7-fluoro-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-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172280
• Molecular Formular: C24H28FN3O10
• Molecular Mass: 537.4916232
• Monoisotopic Mass: 537.17587233
• SMILES: C1CN(CCN1c1c2c3c(cc1F)c(=O)c(cn3[C@H](CO2)C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C
• Canonical SMILES: CN1CCN(CC1)c1c(F)cc2c3c1OC[C@@H](n3cc(c2=O)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C24H28FN3O10/c1-10-9-36-20-14-11(7-13(25)15(20)27-5-3-26(2)4-6-27)16(29)12(8-28(10)14)23(35)38-24-19(32)17(30)18(31)21(37-24)22(33)34/h7-8,10,17-19,21,24,30-32H,3-6,9H2,1-2H3,(H,33,34)/t10-,17-,18-,19+,21-,24-/m0/s1
• InChIKey: GACUZKDACXKMSN-VVQRKAEQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2S)-7-fluoro-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-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2S)-7-fluoro-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-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(3S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate]-β-D-glucopyranuronic Acid; Levofloxacin Glucuronide; Levofloxacin Acyl-β-D-glucuronide 80%

Database IDs

• CAS Number: 160962-46-9
• PubChem SID: 164228190
• PubChem CID: 71749775

CALCULATED PROPERTIES

• Acid pKa: 2.6091032
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -2.9013093
• LogD (pH = 7.4): -3.5748515
• Log P: -2.831279
• Molar Refractivity: 127.2345 cm^3
• Polarizability: 48.7525 Å^3
• Polar Surface Area: 169.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L360010

A glucuronide metabolite of Levofloxacin (L360000).

REFERENCES

• Baillie, T., et al.: Chem. Res. Toxicol., 19, 889 (2006)
• Baba, A., et al.: Chem. Res. Toxicol., 22, 158 (2006)
• Usui, T., et al.: Drug Metab. Dispos., 37, 2383 (2006)