4-[(2R,4S,5S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-5'-methyl-4λ5-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolan]-4-ylium

• ChemBase ID: 163878
• Molecular Formular: C16H25NO7S
• Molecular Mass: 375.4372
• Monoisotopic Mass: 375.13517315
• SMILES: C1CC2CC[N+]1(CC12OC(SC1)C)[C@@H]1OC([C@H]([C@@H](C1O)O)O)C(=O)[O-]
• Canonical SMILES: CC1SCC2(O1)C[N+]1(CCC2CC1)[C@@H]1OC(C(=O)[O-])[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C16H25NO7S/c1-8-24-16(7-25-8)6-17(4-2-9(16)3-5-17)14-12(20)10(18)11(19)13(23-14)15(21)22/h8-14,18-20H,2-7H2,1H3/t8?,9?,10-,11-,12?,13?,14+,16?,17?/m0/s1
• InChIKey: AJUQHTURZRZKHV-FTSSGJODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R,4S,5S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-5'-methyl-4λ^5-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolan]-4-ylium
• IUPAC Traditional name: 4-[(2R,4S,5S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-5'-methyl-4λ^5-azaspiro[bicyclo[2.2.2]octane-2,2'-[1,4]oxathiolan]-4-ylium
• Synonyms: (2'R,3R)-rel-1-Deoxy-1-[2'-Methylspiro[1-azabicyclo[2.2.2]octane-3,5'-oxathiolane]] β-D-Glucopyranuronic Acid; Cevimeline N-Glucuronide(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162258013
• PubChem CID: 71314587

CALCULATED PROPERTIES

• Acid pKa: 3.3361325
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -4.491549
• LogD (pH = 7.4): -4.4891596
• Log P: -5.259618
• Molar Refractivity: 110.2023 cm^3
• Polarizability: 35.671062 Å^3
• Polar Surface Area: 119.28 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C283505

A metabolite of Cevimeline (C283500).