(2S,3S,4S,5R,6R)-6-{[1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 163838
• Molecular Formular: C30H34N2O10
• Molecular Mass: 582.59836
• Monoisotopic Mass: 582.2213453
• SMILES: c1c(c(ccc1)OC)OCCNCC(COc1cccc2c1c1c([nH]2)cccc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: COc1ccccc1OCCNCC(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)COc1cccc2c1c1ccccc1[nH]2
• InChI: InChI=1S/C30H34N2O10/c1-38-21-10-4-5-11-22(21)39-14-13-31-15-17(41-30-27(35)25(33)26(34)28(42-30)29(36)37)16-40-23-12-6-9-20-24(23)18-7-2-3-8-19(18)32-20/h2-12,17,25-28,30-35H,13-16H2,1H3,(H,36,37)/t17?,25-,26-,27+,28-,30+/m0/s1
• InChIKey: PUVQFGCELBOSRN-VKTJNCFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-(9H-Carbazol-4-yloxy)-1-[[[2-(2-methoxyphenoxy)ethyl]amino]methyl]ethyl β-D-Glucopyranosiduronic Acid; Carvedilol Glucuronide; Carvedilol β-D-Glucuronide (mixture of diasteromers)

Database IDs

• CAS Number: 114869-83-9
• PubChem SID: 162257973
• PubChem CID: 49849580

CALCULATED PROPERTIES

• Acid pKa: 3.0725296
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -0.49848446
• LogD (pH = 7.4): -0.51738906
• Log P: -0.49813858
• Molar Refractivity: 147.9184 cm^3
• Polarizability: 61.325737 Å^3
• Polar Surface Area: 171.96 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Beige Solid
• Melting Point: 143-146°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C184640

A metabolite of Carvedilol (C184625).

REFERENCES

• McGurk, K., et al.: Biochem. Pharmacol., 55, 1005 (1998)
• Tukey, R., et al.: Annu. Rev. Pharmacol. Toxicol., 40, 581 (1998)
• Bowalgaha, K., et al.: Br. J. Clin. Pharmacol., 52, 605 (1998)
• Richardson, T., et al.: Drug Metab. Dispos., 34, 351 (1998)