(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-(2H3)methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

• ChemBase ID: 177430
• 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-/m0/s1
• InChIKey: BHLYRWXGMIUIHG-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-(^2H₃)methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
• IUPAC Traditional name: (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-(^2H₃)methyl-3,4-dihydro-1H-isoquinolin-7-ol
• Synonyms: (1S)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-(methyl-d3)-7-isoquinolinol; (+)-Reticuline-d3; L-(+)-Reticuline-d3; Reticulin-d3; S-(+)-Reticuline-d3; d-Reticuline-d3; Reticuline-d3

Database IDs

• CAS Number: 1346603-23-3
• PubChem SID: 164233340
• PubChem CID: 71752017

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: 36.012 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 96-99°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R188502

Labelled Reticuline (R188500). Precursor of many aporphine and morphine-type alkaloids.

REFERENCES

• Kutchan, T., et al.: J. Biol. Chem., 270, 24475 (1995)
• Winkler, A., et al.: J. Biol. Chem., 282, 24437 (1995)
• Heuts, D., et al.: Biochem. J., 413, 175 (1995)