(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{5,8,14-triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene-14-carbonyloxy}oxane-2-carboxylic acid

• ChemBase ID: 179466
• Molecular Formular: C20H21N3O8
• Molecular Mass: 431.39604
• Monoisotopic Mass: 431.13286465
• SMILES: c12c(nccn1)cc1c(c2)C2CN(CC1C2)C(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=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/C20H21N3O8/c24-14-15(25)17(18(27)28)30-19(16(14)26)31-20(29)23-6-8-3-9(7-23)11-5-13-12(4-10(8)11)21-1-2-22-13/h1-2,4-5,8-9,14-17,19,24-26H,3,6-7H2,(H,27,28)/t8?,9?,14-,15-,16+,17-,19-/m0/s1
• InChIKey: FXQDTLDLQVLSRG-NUGMQPMESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 535920-98-0
• PubChem SID: 164235376
• PubChem CID: 71752933

CALCULATED PROPERTIES

• Acid pKa: 3.26411
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.0821807
• LogD (pH = 7.4): -4.2920494
• Log P: -0.8568262
• Molar Refractivity: 100.022 cm^3
• Polarizability: 41.101425 Å^3
• Polar Surface Area: 162.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 181-183°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - V098485

A metabolite of Varenicline.

REFERENCES

• Toide, K., et al.: Biochem. Pharmacol., 67, 1269 (2004)
• Coe, J., et al.: J. Med. Chem., 48, 3474 (2004)
• Doll, R., et al.: Br. J. Cancer, 92, 426 (2004)
• Obach, R., et al.: Drug Metab. Dispos., 33, 262 (2004)