IMPPAT Phytochemical information: 
(3S)-7-hydroxy-6-methoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
(3S)-7-hydroxy-6-methoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Summary

SMILES: COc1c2c(CCN([C@H]2[C@H]2OC(=O)c3c2ccc(c3O)OC)C)cc2c1OCO2
InChI: InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-19(28-9-27-13)20(26-3)14(10)16(22)18-11-4-5-12(25-2)17(23)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1
InChIKey: ICGJAAVPMLXDHF-AEFFLSMTSA-N
DeepSMILES: COcccCCN[C@H]6[C@H]OC=O)cc5cccc6O))OC)))))))))))C))))ccc6OCO5
Scaffold Graph/Node/Bond level: O=C1OC(C2NCCc3cc4c(cc32)OCO4)c2ccccc21
Scaffold Graph/Node level: OC1OC(C2NCCC3CC4OCOC4CC32)C2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC3CC4CCCC4CC32)C2CCCCC12
Functional groups: cOC; CN(C)C; cC(=O)OC; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Phthalide isoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
5'-o-demethylnarcotine
External chemical identifiers:
CID:CID_11372950; ChEMBL:CHEMBL224797; SureChEMBL:SCHEMBL15656749
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3S)-7-hydroxy-6-methoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 399.4
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 86.69
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(3S)-7-hydroxy-6-methoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.79
(3S)-7-hydroxy-6-methoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.66
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No