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

• ChemBase ID: 175740
• Molecular Formular: C22H23NO8
• Molecular Mass: 429.41992
• Monoisotopic Mass: 429.1423667
• SMILES: c12c(c(c3c(c1)CC[N+]([C@H]3[C@@H]1c3c(C(=O)O1)c(c(cc3)OC)OC)([O-])C)OC)OCO2
• Canonical SMILES: COc1ccc2c(c1OC)C(=O)O[C@@H]2[C@H]1c2c(CC[N+]1([O-])C)cc1c(c2OC)OCO1
• InChI: InChI=1S/C22H23NO8/c1-23(25)8-7-11-9-14-20(30-10-29-14)21(28-4)15(11)17(23)18-12-5-6-13(26-2)19(27-3)16(12)22(24)31-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+,23?/m1/s1
• InChIKey: HFGDOEGDRDVXPX-BATLZEKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(1S)-4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl]-4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-6-olate
• IUPAC Traditional name: (5R)-5-[(1S)-4,5-dimethoxy-3-oxo-1H-2-benzofuran-1-yl]-4-methoxy-6-methyl-2H,5H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-6-olate
• Synonyms: [S-(R*,S*)]-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-6-oxido-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3H)-isobenzofuranone; Narcotine N-oxide; α-Narcotine N-Oxide; Noscapine N-Oxide

Database IDs

• CAS Number: 54383-36-7
• PubChem SID: 164231650
• PubChem CID: 13996815

CALCULATED PROPERTIES

• Acid pKa: 14.257973
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.4563334
• LogD (pH = 7.4): 1.4563348
• Log P: 1.4563348
• Molar Refractivity: 109.121 cm^3
• Polarizability: 42.03672 Å^3
• Polar Surface Area: 99.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N882015

An oxidized Noscapine derivative.

REFERENCES

• Tunnicliff, G., et al.: Neurochem. Int., 3, 371 (1981)