(2S,3S,4S,5R,6S)-6-{1-cyclopropyl-6-fluoro-4-oxo-7-[(2,2,3,3,5,5,6,6-2H8)piperazin-1-yl]-1,4-dihydroquinoline-3-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 164782
• Molecular Formular: C23H26FN3O9
• Molecular Mass: 507.4656432
• Monoisotopic Mass: 507.16530765
• SMILES: c1(c(cc2c(c1)n(cc(c2=O)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C1CC1)F)N1CCNCC1
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC(=O)c2cn(C3CC3)c3c(c2=O)cc(c(c3)N2CCNCC2)F)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H26FN3O9/c24-13-7-11-14(8-15(13)26-5-3-25-4-6-26)27(10-1-2-10)9-12(16(11)28)22(34)36-23-19(31)17(29)18(30)20(35-23)21(32)33/h7-10,17-20,23,25,29-31H,1-6H2,(H,32,33)/t17-,18-,19+,20-,23-/m0/s1
• InChIKey: KHGHUQNIHVSBBO-KLJBMEJHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{1-cyclopropyl-6-fluoro-4-oxo-7-[(2,2,3,3,5,5,6,6-^2H₈)piperazin-1-yl]-1,4-dihydroquinoline-3-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{1-cyclopropyl-6-fluoro-4-oxo-7-[(2,2,3,3,5,5,6,6-^2H₈)piperazin-1-yl]quinoline-3-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-(piperazinyl-d8)]-3-quinolinecarboxylate] β-D-Glucopyranuronic Acid; Ciprofloxacin-d8 β-D-Glucuronide

Database IDs

• PubChem SID: 162258917
• PubChem CID: 71314872

CALCULATED PROPERTIES

• Acid pKa: 2.6413245
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.6331077
• LogD (pH = 7.4): -2.6528633
• Log P: -2.6333401
• Molar Refractivity: 120.238 cm^3
• Polarizability: 46.18927 Å^3
• Polar Surface Area: 169.1 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C482512

A labelled metabolite of the fluorinated quinolone antibacterial Ciprofloxacin (C482500).

REFERENCES

• Tanimura, H. et al.: Arzneim.-Forsch., 36, 1417 (1986)
• Hoffken, G., et al.: Antimicrob. Ag. Chemother., 27, 375 (1986)
• Scully, B.E., et al.: Lancet, 1, 819 (1986)