2-(2-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)phenol

• ChemBase ID: 166408
• Molecular Formular: C23H24N2O4
• Molecular Mass: 392.44766
• Monoisotopic Mass: 392.17360726
• SMILES: c12c(c(ccc1)OCC(CNCCOc1c(cccc1)O)O)c1c([nH]2)cccc1
• Canonical SMILES: OC(COc1cccc2c1c1ccccc1[nH]2)CNCCOc1ccccc1O
• InChI: InChI=1S/C23H24N2O4/c26-16(14-24-12-13-28-21-10-4-3-9-20(21)27)15-29-22-11-5-8-19-23(22)17-6-1-2-7-18(17)25-19/h1-11,16,24-27H,12-15H2
• InChIKey: XAUKPPPYYOKVQJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)phenol
• IUPAC Traditional name: 2-(2-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)phenol
• Synonyms: 2-[2-[[3-(9H-Carbazol-4-yloxy)-2-hydroxypropyl]amino]ethoxy]phenol; BM 14242; Desmethylcarvedilol; O-Desmethyl Carvedilol

Database IDs

• CAS Number: 72956-44-6
• PubChem SID: 162260541
• PubChem CID: 155763

CALCULATED PROPERTIES

• Acid pKa: 9.985159
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.33784595
• LogD (pH = 7.4): 1.9221545
• Log P: 3.0437684
• Molar Refractivity: 111.1554 cm^3
• Polarizability: 45.984562 Å^3
• Polar Surface Area: 86.74 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Hot Methanol; Tetrahydrofuran
• Apperance: White Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291475

A metabolite of Carvedilol (C184625), a nonselective β-adrenergic blocker with α1-blocking activity.

REFERENCES

• Sponer, G., et al.: J. Cardiovasc. Pharmacol., 9, 317 (1987)
• Fujimaki, M., et al.: Xenobiotica, 20, 1025 (1987)
• Ruffolo, R., et al.: Eur. J. Clin. Pharmacol., 38, S82 (1987)
• Clohs, L., et al.: J. Pharm. Biomed. Anal., 31, 407 (1987)