(2S,3S,4S,5R,6S)-6-[6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179382
• Molecular Formular: C22H24FN3O9S
• Molecular Mass: 525.5040632
• Monoisotopic Mass: 525.12172858
• SMILES: n12c(c(c(=O)c3c1cc(c(c3)F)N1CCNCC1)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)SC2C
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2c3SC(n3c3c(c2=O)cc(c(c3)N2CCNCC2)F)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H24FN3O9S/c1-8-26-11-7-12(25-4-2-24-3-5-25)10(23)6-9(11)14(27)13(19(26)36-8)21(33)35-22-17(30)15(28)16(29)18(34-22)20(31)32/h6-8,15-18,22,24,28-30H,2-5H2,1H3,(H,31,32)/t8?,15-,16-,17+,18-,22-/m0/s1
• InChIKey: UBVMKQULGWERHE-CZMFQLTOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1H-[1,3]thiazeto[3,2-a]quinoline-3-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate] β-D-Glucopyranose; Ulifloxacin Acyl-β-D-glucuronide

Database IDs

• CAS Number: 172040-93-6
• PubChem SID: 164235292
• PubChem CID: 71752882

CALCULATED PROPERTIES

• Acid pKa: 2.564015
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.2820349
• LogD (pH = 7.4): -2.3018959
• Log P: -2.2823236
• Molar Refractivity: 133.0071 cm^3
• Polarizability: 47.455185 Å^3
• Polar Surface Area: 169.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - U700710

The active metabolite of Prulifloxacin (P838885).

REFERENCES

• Kim, D., et al.: J. Pharm. Sci., 77, 200 (1988)
• Suzuki, T., et al.: Drug Metab. Dispos., 30, 1393 (1988)
• Sun, J., et al.: Eur. J. Pharm. Biopharm., 64, 238 (1988)