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

• ChemBase ID: 170992
• Molecular Formular: C24H26N2O5
• Molecular Mass: 422.47364
• Monoisotopic Mass: 422.18417194
• SMILES: c1ccc2c(c1)c1c([nH]2)cccc1OC[C@H](CNCCOc1c(ccc(c1)O)OC)O
• Canonical SMILES: COc1ccc(cc1OCCNC[C@@H](COc1cccc2c1c1ccccc1[nH]2)O)O
• InChI: InChI=1S/C24H26N2O5/c1-29-21-10-9-16(27)13-23(21)30-12-11-25-14-17(28)15-31-22-8-4-7-20-24(22)18-5-2-3-6-19(18)26-20/h2-10,13,17,25-28H,11-12,14-15H2,1H3/t17-/m0/s1
• InChIKey: PVUVZUBTCLBJMT-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-{[(2S)-3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)-4-methoxyphenol
• IUPAC Traditional name: 3-(2-{[(2S)-3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)-4-methoxyphenol
• Synonyms: (S)-3-[2-[[3-(9H-Carbazol-4-yloxy)-2-hydroxypropyl]amino]ethoxy]-4-methoxyphenol; (S)-5-Hydroxycarvedilol; (S)-(+)-BM 140830; (S)-(+)-M4; (S)-(-)-M4; (S)-(-)-5'-Hydroxyphenyl Carvedilol

Database IDs

• CAS Number: 1217723-80-2
• PubChem SID: 164226902
• PubChem CID: 40425353

CALCULATED PROPERTIES

• Acid pKa: 9.955071
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.1877568
• LogD (pH = 7.4): 1.7786232
• Log P: 2.888631
• Molar Refractivity: 117.6186 cm^3
• Polarizability: 48.47619 Å^3
• Polar Surface Area: 95.97 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetic Acid; DMF; DMSO
• Apperance: Off-White Powder
• Melting Point: 205-207°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H949129

An optically active 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)
• Schaefer, W.H., et al.: Drug Metab. Dispos., 26, 10, 958 (1987)