(3S,4S,6R)-2-(hydroxymethyl)-6-{5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaen-14-yl}oxane-3,4,5-triol

• ChemBase ID: 179469
• Molecular Formular: C19H23N3O5
• Molecular Mass: 373.40302
• Monoisotopic Mass: 373.16377085
• SMILES: c12c(nccn1)cc1c(c2)C2CN(CC1C2)[C@@H]1OC([C@H]([C@@H](C1O)O)O)CO
• Canonical SMILES: OCC1O[C@@H](N2CC3CC(C2)c2c3cc3c(c2)nccn3)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C19H23N3O5/c23-8-15-16(24)17(25)18(26)19(27-15)22-6-9-3-10(7-22)12-5-14-13(4-11(9)12)20-1-2-21-14/h1-2,4-5,9-10,15-19,23-26H,3,6-8H2/t9?,10?,15?,16-,17+,18?,19-/m1/s1
• InChIKey: DVIDZVKOJXFIIZ-LYRYMMDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6R)-2-(hydroxymethyl)-6-{5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaen-14-yl}oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4S,6R)-2-(hydroxymethyl)-6-{5,8,14-triazatetracyclo[10.3.1.0^2,^1^1.0^4,^9]hexadeca-2,4,6,8,10-pentaen-14-yl}oxane-3,4,5-triol
• Synonyms: 8-β-D-Glucopyranosyl-7,8,9,10-tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine; Varenicline N-Glucoside

Database IDs

• CAS Number: 873302-31-9
• PubChem SID: 164235379
• PubChem CID: 46783235

CALCULATED PROPERTIES

• Acid pKa: 12.450547
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.1232069
• LogD (pH = 7.4): -1.0247022
• Log P: -1.0232862
• Molar Refractivity: 94.2598 cm^3
• Polarizability: 38.690315 Å^3
• Polar Surface Area: 119.17 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V098495

A metabolite of Varenicline. Metabolite M7.

REFERENCES

• Dow, J., et al.: Drug Metab. Dispos., 22, 738 (1994)
• Toide, K., et al.: Biochem. Pharmacol., 67, 1269 (1994)
• Coe, J., et al.: J. Med. Chem., 48, 3474 (1994)
• Doll, R., et al.: Br. J. Cancer, 92, 426 (1994)