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

• ChemBase ID: 166411
• Molecular Formular: C23H24N2O4
• Molecular Mass: 392.44766
• Monoisotopic Mass: 392.17360726
• SMILES: c1ccc2c(c1)c1c([nH]2)cccc1OC[C@H](CNCCOc1c(cccc1)O)O
• Canonical SMILES: O[C@H](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/t16-/m0/s1
• InChIKey: XAUKPPPYYOKVQJ-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 123372-13-4
• PubChem SID: 162260544
• PubChem CID: 40425346

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: Off-White Solid
• Melting Point: 155-156°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291485

An optically active metabolite of Carvedilol (C184625), a nonselective β-adrenergic blocker with α1-blocking activity. [α]D= -18.7 (c= 0.1 methanol)

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)