5-{[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-methoxyphenol

• ChemBase ID: 175670
• Molecular Formular: C19H23NO4
• Molecular Mass: 329.39022
• Monoisotopic Mass: 329.16270822
• SMILES: c1(c(cc2c(c1)[C@@H](NCC2)Cc1cc(c(cc1)OC)O)OC)OC
• Canonical SMILES: COc1ccc(cc1O)C[C@@H]1NCCc2c1cc(OC)c(c2)OC
• InChI: InChI=1S/C19H23NO4/c1-22-17-5-4-12(9-16(17)21)8-15-14-11-19(24-3)18(23-2)10-13(14)6-7-20-15/h4-5,9-11,15,20-21H,6-8H2,1-3H3/t15-/m0/s1
• InChIKey: PBARFBACJNHQIC-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-methoxyphenol
• IUPAC Traditional name: 5-{[(1S)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-methoxyphenol
• Synonyms: 2-Methoxy-5-[[(1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]phenol; (S)-Nor Laudanine

Database IDs

• CAS Number: 1206614-00-7
• PubChem SID: 164231580
• PubChem CID: 7055276

CALCULATED PROPERTIES

• Acid pKa: 10.102192
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.25587
• LogD (pH = 7.4): 1.0316805
• Log P: 2.4985206
• Molar Refractivity: 93.0239 cm^3
• Polarizability: 36.083626 Å^3
• Polar Surface Area: 59.95 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N710020

A minor Papaver somniferum opium benzyltetrahydoisoquinoline alkaloid, a Laudanine (L178500) derivative.

REFERENCES

• Brochmann-Hanssen, E., et al.: J. Pharm. Sci., 57, 940 (1968)
• Pyo, M., et al.: Bioorg. Med. Chem. Lett., 18, 4110 (1968)