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

• ChemBase ID: 179756
• Molecular Formular: C22H23NO7
• Molecular Mass: 413.42052
• Monoisotopic Mass: 413.14745208
• SMILES: c12C(=O)O[C@H]([C@H]3c4c(c5c(cc4CCN3C)OCO5)OC)c1ccc(c2OC)OC
• Canonical SMILES: COc1ccc2c(c1OC)C(=O)O[C@@H]2[C@@H]1N(C)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
• InChIKey: AKNNEGZIBPJZJG-MSOLQXFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-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-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one
• Synonyms: Gnoscopine; Opianine; Anarkotin; Tusscapine; Noscapine

Database IDs

• CAS Number: 128-62-1
• PubChem SID: 164235666
• PubChem CID: 275196

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: 41.770374 Å^3
• Polar Surface Area: 75.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Sigma receptor agonist

Product Information

• Application(s): Antitussive agent, of similar potency to and poss. with some advantages over codeine.; Mod. effective smooth muscle relaxant.

REFERENCES

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