(2S,3S,4S,5R,6R)-6-({2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylazaniumyl)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 163634
• Molecular Formular: C22H27ClN2O7
• Molecular Mass: 466.91198
• Monoisotopic Mass: 466.15067889
• SMILES: c1(ncccc1)C(OCC[N+]([C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])(C)C)c1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)C(c1ccccn1)OCC[N+]([C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)(C)C
• InChI: InChI=1S/C22H27ClN2O7/c1-25(2,21-18(28)16(26)17(27)20(32-21)22(29)30)11-12-31-19(15-5-3-4-10-24-15)13-6-8-14(23)9-7-13/h3-10,16-21,26-28H,11-12H2,1-2H3/t16-,17-,18+,19?,20-,21+/m0/s1
• InChIKey: NAEXCCUZPJWPMZ-RBGXYZBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-({2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylazaniumyl)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-({2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylammonio)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: N-β-D-Glucopyranuronosyl-N,N-dimethyl-2-[1-chlorophenyl-1-(2-pyridinyl)methoxy]ethanaminium Inner Salt; Carbinoxamine β-D-Glucuronide

Database IDs

• PubChem SID: 162257769
• PubChem CID: 71314508

CALCULATED PROPERTIES

• Acid pKa: 2.9696789
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.2182088
• LogD (pH = 7.4): -2.2136528
• Log P: -2.9904664
• Molar Refractivity: 136.408 cm^3
• Polarizability: 45.648926 Å^3
• Polar Surface Area: 132.17 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C175945

A metabolite of Carbinoxamine (C175920).