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

• ChemBase ID: 170985
• Molecular Formular: C24H26N2O5
• Molecular Mass: 422.47364
• Monoisotopic Mass: 422.18417194
• SMILES: c1ccc2c(c1)c1c([nH]2)cccc1OCC(CNCCOc1c(cc(cc1)O)OC)O
• Canonical SMILES: COc1cc(O)ccc1OCCNCC(COc1cccc2c1c1ccccc1[nH]2)O
• InChI: InChI=1S/C24H26N2O5/c1-29-23-13-16(27)9-10-21(23)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
• InChIKey: ZCJHEORDHXCJNB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)-3-methoxyphenol
• IUPAC Traditional name: 4-(2-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}ethoxy)-3-methoxyphenol
• Synonyms: 4-[2-[[3-(9H-Carbazol-4-yloxy)-2-hydroxypropyl]amino]ethoxy]-3-methoxyphenol; 4-Hydroxycarvedilol; BM 140686; BM 14686; 4'-Hydroxyphenyl Carvedilol

Database IDs

• CAS Number: 142227-49-4
• PubChem SID: 164226895
• PubChem CID: 4572774

CALCULATED PROPERTIES

• Acid pKa: 9.949964
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.17337397
• LogD (pH = 7.4): 1.751418
• Log P: 2.8772461
• Molar Refractivity: 117.6186 cm^3
• Polarizability: 48.476192 Å^3
• Polar Surface Area: 95.97 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 176-178°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H949120

A metabolite of Carvedilol (C184625). It is used in the treatment of hypertension.

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)