(2S,3S,4S,5R,6S)-6-{[13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 170443
• Molecular Formular: C25H27ClN2O7
• Molecular Mass: 502.94408
• Monoisotopic Mass: 502.15067889
• SMILES: C1(=C2CCNCC2)c2c(CCc3c1ncc(c3)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)cc(cc2)Cl
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cnc3c(c2)CCc2c(C3=C3CCNCC3)ccc(c2)Cl)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H27ClN2O7/c26-15-3-4-17-13(9-15)1-2-14-10-16(11-28-19(14)18(17)12-5-7-27-8-6-12)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h3-4,9-11,20-23,25,27,29-31H,1-2,5-8H2,(H,32,33)/t20-,21-,22+,23-,25+/m0/s1
• InChIKey: XLMRWMPRWQUMIJ-LYVDORBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-3-yl β-D-Glucopyranosiduronic Acid; M13 Metabolite; 3-Hydroxy Desloratadine β-D-Glucuronide

Database IDs

• CAS Number: 774538-89-5
• PubChem SID: 164226353
• PubChem CID: 29918869

CALCULATED PROPERTIES

• Acid pKa: 2.6567514
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.7620777
• LogD (pH = 7.4): -0.7562532
• Log P: -0.7552841
• Molar Refractivity: 135.0315 cm^3
• Polarizability: 49.534744 Å^3
• Polar Surface Area: 141.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H936760

A metabolite of Desloratadine.

REFERENCES

• Miners, J., et al.: Cancer Res., 57, 284 (1997)
• Strassburg, C., et al.: J. Biol. Chem., 273, 8719 (1997)
• Fisher, M., et al.: Drug Metab. Dispos., 28, 560 (1997)
• Soars, M., et al.: Drug Metab. Dispos., 31, 762 (2003)