(3R)-6,7-dimethoxy-3-[(5S)-6-(2H3)methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one

• ChemBase ID: 170027
• Molecular Formular: C21H21NO6
• Molecular Mass: 383.39454
• Monoisotopic Mass: 383.1368874
• SMILES: c12c(cc3c(c1)[C@H](N(CC3)C)[C@H]1c3c(C(=O)O1)c(c(cc3)OC)OC)OCO2
• Canonical SMILES: COc1c(OC)ccc2c1C(=O)O[C@H]2[C@H]1N(C)CCc2c1cc1OCOc1c2
• InChI: InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m0/s1
• InChIKey: JZUTXVTYJDCMDU-RBUKOAKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-6,7-dimethoxy-3-[(5S)-6-(^2H₃)methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one
• IUPAC Traditional name: (3R)-6,7-dimethoxy-3-[(5S)-6-(^2H₃)methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
• Synonyms: (3S)-rel-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-6-(methyl-d3)-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone; (+/-)-Hydrastine-d3; (+/-)-β-Hydrastine-d3

Database IDs

• PubChem SID: 164225937
• PubChem CID: 71748775

CALCULATED PROPERTIES

• Acid pKa: 14.781298
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.8118249
• LogD (pH = 7.4): 2.4206343
• Log P: 2.7383814
• Molar Refractivity: 100.6129 cm^3
• Polarizability: 39.227493 Å^3
• Polar Surface Area: 66.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H675692

Labelled (+/-)-β-Hydrastine (H675692). Inhibitor of Dopamine biosynthesis.

REFERENCES

• Jones, D., et al.: Drug Metab. Disposition, 35, 1466 (2007)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2007)