Molecule ID: 10237

IUPAC Name: (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one

Description: The molecule is a benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species. It has a role as an agrochemical, a central nervous system stimulant, a GABA-gated chloride channel antagonist, a neurotoxin and a GABAA receptor antagonist. It is an isoquinoline alkaloid, a member of isoquinolines and a benzylisoquinoline alkaloid.

SMILES: CN1CCc2cc3c(cc2[C@H]1[C@@H]1OC(=O)c2c1ccc1c2OCO1)OCO3

SELFIES: [C][N][C][C][C][=C][C][=C][Branch2][Ring1][=N][C][=C][Ring1][=Branch1][C@H1][Ring1][#Branch2][C@@H1][O][C][=Branch1][C][=O][C][=C][Ring1][=Branch1][C][=C][C][=C][Ring1][=Branch1][O][C][O][Ring1][Branch1][O][C][O][Ring2][Ring1][Branch1]

InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1

Molecular Properties:
- Polar Surface Area: 66.5 Ų
- LogP: 2.6