(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-(13C,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: 175739
• Molecular Formular: C22H23NO7
• Molecular Mass: 414.41317484
• Monoisotopic Mass: 414.15080692
• SMILES: c12c(c(c3c(c1)CCN([C@H]3[C@@H]1c3c(C(=O)O1)c(c(cc3)OC)OC)[13CH3])OC)OCO2
• Canonical SMILES: COc1ccc2c(c1OC)C(=O)O[C@@H]2[C@@H]1N([13CH3])CCc2c1c(OC)c1c(c2)OCO1
• InChI: InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1/i1+1
• InChIKey: AKNNEGZIBPJZJG-BUNRNNAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-(^1^3C,^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: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-(^1^3C,^2H₃)methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
• Synonyms: (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone-13C,d3; (-)-α-Narcotine-13C,d3; (-)-Narcotine-13C,d3; α-Narcotine-13C,d3; Capval-13C,d3; Coscopin-13C,d3; Noscapine-13C,d3

Database IDs

• PubChem SID: 164231649
• PubChem CID: 71751263

CALCULATED PROPERTIES

• Acid pKa: 14.593244
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.5909894
• LogD (pH = 7.4): 2.5351286
• Log P: 2.58071
• Molar Refractivity: 107.0761 cm^3
• Polarizability: 41.770386 Å^3
• Polar Surface Area: 75.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 174-176°C

DETAILS

Toronto Research Chemicals - N882002

Antitussive.

REFERENCES

• Tsunoda, N., et al.: Xenobiotica, 9, 181 (1979)
• Dhalstroem, B., et al.: Eur. J. Clin. Pharmacol., 22, 535 (1979)
• Al-Yahya, M.A., et al.: Anal. Profiles Drug Subs., 11, 407 (1979)