(2S,3S,4S,5R,6R)-6-[(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylazaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 171576
• Molecular Formular: C25H32N2O6
• Molecular Mass: 456.53138
• Monoisotopic Mass: 456.22603675
• SMILES: c12N(c3c(CCc1cccc2)cccc3)CCC[N+]([C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])(C)C
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@H]([C@H]([C@H]([C@@H]1O)O)O)[N+](CCCN1c2ccccc2CCc2c1cccc2)(C)C
• InChI: InChI=1S/C25H32N2O6/c1-27(2,24-22(30)20(28)21(29)23(33-24)25(31)32)15-7-14-26-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)26/h3-6,8-11,20-24,28-30H,7,12-15H2,1-2H3/t20-,21-,22+,23-,24+/m0/s1
• InChIKey: CXPKQHSXFUNBMP-OSFFKXSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylazaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylammonio]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: N-β-D-Glucopyranuronosyl-10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanaminium Inner Salt; Imipramine N-Glucuronide; Imipramine N-β-D-Glucuronide

Database IDs

• CAS Number: 165602-94-8
• PubChem SID: 164227486
• PubChem CID: 46176835

CALCULATED PROPERTIES

• Acid pKa: 3.4046364
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.209809
• LogD (pH = 7.4): -1.2070023
• Log P: -1.9774554
• Molar Refractivity: 144.8858 cm^3
• Polarizability: 47.835148 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 133-136°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I465990

A metabolite of Imipramine (I465980).

REFERENCES

• Magdalou, J., et al.: J. Biol. Chem., 257, 13624 (1982)
• Orzechowski, A., et al.: Carcinogenesis, 15, 1549 (1982)
• Hawes, E., et al.: Drug Metab. Dispos., 26, 830 (1982)