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

• ChemBase ID: 175709
• Molecular Formular: C18H21NO4
• Molecular Mass: 315.36364
• Monoisotopic Mass: 315.14705816
• SMILES: c1(c(cc2c(c1)[C@@H](NCC2)Cc1cc(c(cc1)OC)O)OC)O
• Canonical SMILES: COc1ccc(cc1O)C[C@@H]1NCCc2c1cc(O)c(c2)OC
• InChI: InChI=1S/C18H21NO4/c1-22-17-4-3-11(8-15(17)20)7-14-13-10-16(21)18(23-2)9-12(13)5-6-19-14/h3-4,8-10,14,19-21H,5-7H2,1-2H3/t14-/m0/s1
• InChIKey: FVEMXQCEJGGXJB-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
• IUPAC Traditional name: (-)-norreticuline
• Synonyms: (S)-Norreticuline; Norreticuline; Nor Reticuline; (1S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-7-isoquinolinol; 2-Demethylreticuline; (-)-(S)-N-Norreticuline; (-)-Norreticuline

Database IDs

• CAS Number: 4781-58-2
• PubChem SID: 164231619
• PubChem CID: 441069

CALCULATED PROPERTIES

• Acid pKa: 9.815201
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.3122004
• LogD (pH = 7.4): 1.1626774
• Log P: 2.3571336
• Molar Refractivity: 88.5416 cm^3
• Polarizability: 34.171646 Å^3
• Polar Surface Area: 70.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N825850

Reticuline (R188500) analog. (S)-Norreticuline is the precursor for the biosynthesis of Erythrina alkaloids. (S)-Norreticuline and (S)-reticuline stimulated the proliferation of cultured cells from murine hair.

REFERENCES

• Hattori, M., et al.: J. Dermatol., 10, 45 (1983)
• Tanigaki, N., et al.: Arch. Dermatol. Res., 282, 402 (1983)