{2-[4-(benzyloxy)-2-methoxyphenoxy]ethyl}[(2S)-3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amine

• ChemBase ID: 161860
• Molecular Formular: C31H32N2O5
• Molecular Mass: 512.59618
• Monoisotopic Mass: 512.23112213
• SMILES: c1ccc2c(c1)c1c([nH]2)cccc1OC[C@H](CNCCOc1c(cc(cc1)OCc1ccccc1)OC)O
• Canonical SMILES: COc1cc(OCc2ccccc2)ccc1OCCNC[C@@H](COc1cccc2c1c1ccccc1[nH]2)O
• InChI: InChI=1S/C31H32N2O5/c1-35-30-18-24(37-20-22-8-3-2-4-9-22)14-15-28(30)36-17-16-32-19-23(34)21-38-29-13-7-12-27-31(29)25-10-5-6-11-26(25)33-27/h2-15,18,23,32-34H,16-17,19-21H2,1H3/t23-/m0/s1
• InChIKey: WFGLUJVTGHMGCX-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[4-(benzyloxy)-2-methoxyphenoxy]ethyl}[(2S)-3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amine
• IUPAC Traditional name: {2-[4-(benzyloxy)-2-methoxyphenoxy]ethyl}[(2S)-3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amine
• Synonyms: (S)-(+)-1-(9H-Carbazol-4-yloxy)-3-[[2-[2-methoxy-4-(phenylmethoxy)phenoxy]ethyl]amino]-2-propanol; (S)-(-)-4’-Benzyloxy Carvedilol; (S)-(-)-4'-Benzyloxyphenyl Carvedilol

Database IDs

• CAS Number: 1217733-91-9
• PubChem SID: 162255995
• PubChem CID: 29973562

CALCULATED PROPERTIES

• Acid pKa: 14.030433
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.0437014
• LogD (pH = 7.4): 3.6229453
• Log P: 4.9916563
• Molar Refractivity: 146.7135 cm^3
• Polarizability: 60.017223 Å^3
• Polar Surface Area: 84.97 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B287658

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

REFERENCES

• Schaefer, W.H., et al.: Drug Metab. Dispos., 26, 10, 958 (1998)