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

• ChemBase ID: 172242
• Molecular Formular: C20H25NO4
• Molecular Mass: 343.4168
• Monoisotopic Mass: 343.17835829
• SMILES: c1(c(cc2c(c1)[C@@H](N(CC2)C)Cc1cc(c(cc1)OC)O)OC)OC
• Canonical SMILES: COc1ccc(cc1O)C[C@@H]1N(C)CCc2c1cc(OC)c(c2)OC
• InChI: InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3/t16-/m0/s1
• InChIKey: MPYHGNAJOKCMAQ-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(1S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-methoxyphenol
• IUPAC Traditional name: 5-{[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl}-2-methoxyphenol
• Synonyms: 2-Methoxy-5-[[(1S)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-phenol; 1αH-Laudanidine; (+)-Laudanidine; L-(+)-Laudanidine; (S)-Laudanine

Database IDs

• CAS Number: 3122-95-0
• PubChem SID: 164228152
• PubChem CID: 821396

CALCULATED PROPERTIES

• Acid pKa: 10.018453
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.544392
• LogD (pH = 7.4): 2.3156016
• Log P: 3.1337082
• Molar Refractivity: 98.3186 cm^3
• Polarizability: 37.92474 Å^3
• Polar Surface Area: 51.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L178500

An alkaloid from Xylopia championii as antioxidant and antifungal agent.

REFERENCES

• Sonnet, P., et al.: J. Pharm. Sci., 60, 1254 (1971)
• Stevigny, C., et al.: Curr. Med. Chem., 5, 173 (1971)
• Costa, E., et al.: J. Nat. Prod., 69, 292 (1971)