3-cyclopentyl-4-[(2S)-2-hydroxy-3-{[2-(2H3)methyl(2H6)propan-2-yl]amino}propoxy]phenol hydrochloride

• ChemBase ID: 171045
• Molecular Formular: C18H30ClNO3
• Molecular Mass: 343.8887
• Monoisotopic Mass: 343.19142151
• SMILES: c1c(ccc(c1C1CCCC1)OC[C@H](CNC(C)(C)C)O)O.Cl
• Canonical SMILES: O[C@H](COc1ccc(cc1C1CCCC1)O)CNC(C)(C)C.Cl
• InChI: InChI=1S/C18H29NO3.ClH/c1-18(2,3)19-11-15(21)12-22-17-9-8-14(20)10-16(17)13-6-4-5-7-13;/h8-10,13,15,19-21H,4-7,11-12H2,1-3H3;1H/t15-;/m0./s1
• InChIKey: IRXCLCQOLQYHQP-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-cyclopentyl-4-[(2S)-2-hydroxy-3-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}propoxy]phenol hydrochloride
• IUPAC Traditional name: 3-cyclopentyl-4-[(2S)-2-hydroxy-3-{[2-(^2H₃)methyl(^2H₆)propan-2-yl]amino}propoxy]phenol hydrochloride
• Synonyms: 3-Cyclopentyl-4-[(2S)-3-[(1,1-dimethylethyl-d9)amino]-2-hydroxypropoxy]phenol Hydrochloride; (S)-3-Cyclopentyl-4-[3-[(1,1-dimethylethyl-d9)amino]-2-hydroxypropoxy]phenol Hydrochloride; (S)-4-Hydroxy Penbutolol-d9 Hydrochloride

Database IDs

• PubChem SID: 164226955
• PubChem CID: 71749234

CALCULATED PROPERTIES

• Acid pKa: 10.198081
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.040713277
• LogD (pH = 7.4): 0.94549
• Log P: 2.7605824
• Molar Refractivity: 88.5852 cm^3
• Polarizability: 35.045265 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948947

A hydroxylated labelled metabolite of Penbutolol (P220500).

REFERENCES

• Giudicelli, J., et al.: Br. J. Clin. Pharmacol., 4, 135 (1977)
• Lehr, K., et a.l.: Arzneim.-Forsch., 37, 1373 (1977)
• Radulovic, D., et al.: J. Pharm. Biomed. Anal., 8, 739 (1977)