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

• ChemBase ID: 175667
• Molecular Formular: C20H19NO6
• Molecular Mass: 369.36796
• Monoisotopic Mass: 369.12123733
• SMILES: c12c(cc3c(c1)[C@H](NCC3)[C@H]1c3c(C(=O)O1)c(c(cc3)OC)OC)OCO2
• Canonical SMILES: COc1c(OC)ccc2c1C(=O)O[C@H]2[C@H]1NCCc2c1cc1OCOc1c2
• InChI: InChI=1S/C20H19NO6/c1-23-13-4-3-11-16(19(13)24-2)20(22)27-18(11)17-12-8-15-14(25-9-26-15)7-10(12)5-6-21-17/h3-4,7-8,17-18,21H,5-6,9H2,1-2H3/t17-,18+/m0/s1
• InChIKey: VKUFOPJSFWVKKJ-ZWKOTPCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(5S)-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one
• IUPAC Traditional name: (3R)-3-[(5S)-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-3H-2-benzofuran-1-one
• Synonyms: (3S)-rel-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone; (+/-)-β-Norhydrastine; (+/-)-Nor-β-hydrastine

Database IDs

• CAS Number: 66408-36-4
• PubChem SID: 164231577
• PubChem CID: 71751220

CALCULATED PROPERTIES

• Acid pKa: 14.797986
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.04068105
• LogD (pH = 7.4): 1.689751
• Log P: 2.3553333
• Molar Refractivity: 95.3182 cm^3
• Polarizability: 37.393692 Å^3
• Polar Surface Area: 75.25 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N705600

GABAergic receptor-binding phthalideisoquinoline alkaloids.

REFERENCES

• Kardos, J., et al.: Biochem. Pharmacol., 33, 3537 (1984)