(2S,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-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: 179464
• Molecular Formular: C27H29N3O11
• Molecular Mass: 571.53266
• Monoisotopic Mass: 571.18020876
• 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)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(=O)N2CC3CC(C2)c2c3cc3c(c2)nccn3)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C27H29N3O11/c1-12(31)37-21-22(38-13(2)32)24(39-14(3)33)26(40-23(21)25(34)36-4)41-27(35)30-10-15-7-16(11-30)18-9-20-19(8-17(15)18)28-5-6-29-20/h5-6,8-9,15-16,21-24,26H,7,10-11H2,1-4H3/t15?,16?,21-,22-,23-,24+,26-/m0/s1
• InChIKey: FAXWOZNAILXBTR-CXBYFGHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-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-tris(acetyloxy)-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)2,3,4-Tri-O-acetyl-β-D-glucopyranuronic Acid Methyl Ester; Varenicline Carbamoyl 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164235374
• PubChem CID: 71752931

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 0.6124018
• LogD (pH = 7.4): 0.61244357
• Log P: 0.6124441
• Molar Refractivity: 132.2456 cm^3
• Polarizability: 54.732056 Å^3
• Polar Surface Area: 169.75 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - V098470

A protected metabolite of Varenicline.