(1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

• ChemBase ID: 177431
• Molecular Formular: C19H23NO4
• Molecular Mass: 329.39022
• Monoisotopic Mass: 329.16270822
• SMILES: c1(c(cc2c(c1)[C@H](N(CC2)C)Cc1cc(c(cc1)OC)O)OC)O
• Canonical SMILES: COc1ccc(cc1O)C[C@H]1N(C)CCc2c1cc(O)c(c2)OC
• InChI: InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m1/s1
• InChIKey: BHLYRWXGMIUIHG-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
• IUPAC Traditional name: (-)-reticuline
• Synonyms: (1R)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-Isoquinolinol; (-)-Reticuline; (R)-(-)-Reticuline; L-Reticuline; (R)-Reticuline

Database IDs

• CAS Number: 3968-19-2
• PubChem SID: 164233341
• PubChem CID: 440586

CALCULATED PROPERTIES

• Acid pKa: 9.764061
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.7340227
• LogD (pH = 7.4): 2.4816308
• Log P: 3.1049592
• Molar Refractivity: 93.8363 cm^3
• Polarizability: 36.01199 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R188505

(R)-Reticuline is the (R)-enantiomer of Reticuline, a tetrahydrobenzylisoquinoline alkaloid found in opium. (R)-Reticuline is converted into Salutaridine by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum

REFERENCES

• Gerardy, R. et al.: Phytochemistry, 32, 79 (1992)
• Grobe, N. et al.: Proc. Mat. Acad. Sci. U.S.A., 107, 8147 (1992)