(2S,3S,4S,5R,6S)-6-{7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174839
• Molecular Formular: C27H32FN3O10
• Molecular Mass: 577.5554832
• Monoisotopic Mass: 577.20717246
• SMILES: [C@@H]1([C@@H](O[C@@H]([C@H]([C@H]1O)O)C(=O)O)OC(=O)c1c(=O)c2cc(c(c(c2n(c1)C1CC1)OC)N1C[C@H]2[C@@H](C1)NCCC2)F)O
• Canonical SMILES: COc1c(N2C[C@@H]3[C@H](C2)CCCN3)c(F)cc2c1n(cc(c2=O)C(=O)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O)C1CC1
• InChI: InChI=1S/C27H32FN3O10/c1-39-23-17-13(7-15(28)18(23)30-8-11-3-2-6-29-16(11)10-30)19(32)14(9-31(17)12-4-5-12)26(38)41-27-22(35)20(33)21(34)24(40-27)25(36)37/h7,9,11-12,16,20-22,24,27,29,33-35H,2-6,8,10H2,1H3,(H,36,37)/t11-,16+,20-,21-,22+,24-,27-/m0/s1
• InChIKey: CAEIKPOEUGEJIR-XNYZSDPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{7-[(4aS,7aS)-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carbonyloxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylate] β-D-Glucopyranuronic Acid; rac cis-Moxifloxacin Acyl-β-D-glucuronide

Database IDs

• CAS Number: 733002-61-4
• PubChem SID: 164230749
• PubChem CID: 71750855

CALCULATED PROPERTIES

• Acid pKa: 2.6203887
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -2.2205498
• LogD (pH = 7.4): -2.2238002
• Log P: -2.2203279
• Molar Refractivity: 138.5226 cm^3
• Polarizability: 53.49734 Å^3
• Polar Surface Area: 178.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 170-173°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M745010

A metabolite of Moxifloxacin (M745000).

REFERENCES

• Steinijans, V., et al.: J. Clin. Pharmacol. Ther., 29, 323 (1991)
• Haria, M., et al.: Drugs, 51, 585 (1991)
• Pickerill, K., et al.: Pharmacotherapy, 20, 417(1991)