(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene-14-carboxylate

• ChemBase ID: 179465
• Molecular Formular: C21H23N3O8
• Molecular Mass: 445.42262
• Monoisotopic Mass: 445.14851471
• SMILES: c12c(nccn1)cc1c(c2)C2CN(CC1C2)C(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OC)O)O)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(=O)N2CC3CC(C2)c2c3cc3c(c2)nccn3)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H23N3O8/c1-30-19(28)18-16(26)15(25)17(27)20(31-18)32-21(29)24-7-9-4-10(8-24)12-6-14-13(5-11(9)12)22-2-3-23-14/h2-3,5-6,9-10,15-18,20,25-27H,4,7-8H2,1H3/t9?,10?,15-,16-,17+,18-,20-/m0/s1
• InChIKey: DKKDSFOEFCTGID-ZENVPFGISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl 5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaene-14-carboxylate
• IUPAC Traditional name: (2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(methoxycarbonyl)oxan-2-yl 5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaene-14-carboxylate
• Synonyms: 1-(6,7,9,10-Tetrahydro-6,10-methano-8H-pyrazino[2,3-h][3]benzazepin-8-carboxylate)β-D-Glucopyranuronic Acid Methyl Ester; Varenicline Carbamoyl β-D-Glucuronide Methyl Ester

Database IDs

• PubChem SID: 164235375
• PubChem CID: 71752932

CALCULATED PROPERTIES

• Acid pKa: 12.160342
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.7109745
• LogD (pH = 7.4): -0.71094024
• Log P: -0.71093214
• Molar Refractivity: 104.7911 cm^3
• Polarizability: 43.166084 Å^3
• Polar Surface Area: 151.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - V098480

A protected metabolite of Varenicline.