IMPPAT Phytochemical information: 
8,9,10-trimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
8,9,10-trimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
Summary

SMILES: COc1cc2C3C(CC=C4C3N(C)CC4)OC(c2c(c1OC)OC)O
InChI: InChI=1S/C19H25NO5/c1-20-8-7-10-5-6-12-14(16(10)20)11-9-13(22-2)17(23-3)18(24-4)15(11)19(21)25-12/h5,9,12,14,16,19,21H,6-8H2,1-4H3
InChIKey: MNAREALDHXFRFJ-UHFFFAOYSA-N
DeepSMILES: COcccCCCC=CC6NC)CC5)))))))OCc6cc%10OC)))OC))))O
Scaffold Graph/Node/Bond level: C1=C2CCNC2C2c3ccccc3COC2C1
Scaffold Graph/Node level: C1CCC2C(C1)COC1CCC3CCNC3C12
Scaffold Graph level: C1CCC2C(C1)CCC1CCC3CCCC3C12
Functional groups: cOC; CC=C(C)C; CN(C)C; cC(O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Homolycorine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
nerinine
External chemical identifiers:
CID:CID_573106
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
8,9,10-trimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 347.41
Log P RDKit 2.22
Topological polar surface area (Å2) RDKit 60.39
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
8,9,10-trimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.85
8,9,10-trimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes