1-{3-acetyl-4-[(2S)-2-hydroxy-3-{[2-(2H3)methyl(2H6)propan-2-yl]amino}propoxy]phenyl}-3,3-diethylurea hydrochloride

• ChemBase ID: 163960
• Molecular Formular: C20H34ClN3O4
• Molecular Mass: 415.95466
• Monoisotopic Mass: 415.22378426
• SMILES: c1(c(ccc(c1)NC(=O)N(CC)CC)OC[C@H](CNC(C)(C)C)O)C(=O)C.Cl
• Canonical SMILES: CCN(C(=O)Nc1ccc(c(c1)C(=O)C)OC[C@H](CNC(C)(C)C)O)CC.Cl
• InChI: InChI=1S/C20H33N3O4.ClH/c1-7-23(8-2)19(26)22-15-9-10-18(17(11-15)14(3)24)27-13-16(25)12-21-20(4,5)6;/h9-11,16,21,25H,7-8,12-13H2,1-6H3,(H,22,26);1H/t16-;/m0./s1
• InChIKey: VKJHTUVLJYWAEY-NTISSMGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-acetyl-4-[(2S)-2-hydroxy-3-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}propoxy]phenyl}-3,3-diethylurea hydrochloride
• IUPAC Traditional name: 1-{3-acetyl-4-[(2S)-2-hydroxy-3-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}propoxy]phenyl}-3,3-diethylurea hydrochloride
• Synonyms: N'-[3-Acetyl-4-[(2S)-3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]phenyl]-N,N-diethylurea-d9 Hydrochloride; (-)-(S)-Celiprolol-d9 Hydrochloride; (-)-Celiprolol-d9 Hydrochloride; (S)-Celiprolol-d9 Hydrochloride; l-Celiprolol-d9 Hydrochloride; (S)-(-)-Celiprolol-d9 Hydrochloride

Database IDs

• PubChem SID: 162258095
• PubChem CID: 71314633

CALCULATED PROPERTIES

• Acid pKa: 13.554427
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.6949553
• LogD (pH = 7.4): -0.72177505
• Log P: 1.4975762
• Molar Refractivity: 108.2468 cm^3
• Polarizability: 41.324116 Å^3
• Polar Surface Area: 90.9 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C254497

Labelled analog of a Cardioselective β1-adrenergic blocker. Antihypertensive, antianginal.

REFERENCES

• Mazzo, D.J., et al.: Anal. Profiles Drug Subs., 20, 237 (1991)
• Meininger, C., et al.: Biochem. J., 349, 353 (1991)
• Ruan, H., et al.: Diabetes, 51, 1319 (1991)
• Liao, Y., et al.: Circulation, 110, 692 (1991)