3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}(methyl)amino)propyl]-8-hydroxy-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one

• ChemBase ID: 166559
• Molecular Formular: C26H34N2O5
• Molecular Mass: 454.55856
• Monoisotopic Mass: 454.2467722
• SMILES: c1(c(cc2c(c1)CC(=O)N(CC2)CCCN(C[C@H]1Cc2c1cc(c(c2)OC)OC)C)OC)O
• Canonical SMILES: COc1cc2[C@@H](CN(CCCN3CCc4c(CC3=O)cc(c(c4)OC)O)C)Cc2cc1OC
• InChI: InChI=1S/C26H34N2O5/c1-27(16-20-10-19-13-24(32-3)25(33-4)15-21(19)20)7-5-8-28-9-6-17-12-23(31-2)22(29)11-18(17)14-26(28)30/h11-13,15,20,29H,5-10,14,16H2,1-4H3/t20-/m1/s1
• InChIKey: BMPIAMMIUINAOW-HXUWFJFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}(methyl)amino)propyl]-8-hydroxy-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one
• IUPAC Traditional name: 3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]methyl}(methyl)amino)propyl]-8-hydroxy-7-methoxy-4,5-dihydro-1H-3-benzazepin-2-one
• Synonyms: 3-[3-[[[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl]methylamino]propyl]-1,3,4,5-tetrahydro-8-hydroxy-7-methoxy-2H-3-benzazepin-2-one; S 33174; 8-Demethyl Ivabradine

Database IDs

• CAS Number: 304464-97-9
• PubChem SID: 162260692
• PubChem CID: 71315777

CALCULATED PROPERTIES

• Acid pKa: 9.967766
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.76757574
• LogD (pH = 7.4): 0.62140393
• Log P: 2.1087503
• Molar Refractivity: 129.023 cm^3
• Polarizability: 49.457684 Å^3
• Polar Surface Area: 71.47 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292990

Ivabradine (I940500) metabolite.

REFERENCES

• Duffull, S., et al.: Eur. J. Pharm. Sci., 10, 285 (2000)
• Portoles, A., et al.: J. Clin. Pharmacol., 46, 1195 (2000)