IMPPAT Phytochemical information: 
(8Bs,13as)-3,6,7-trimethoxy-8b,9,11,12,13,13a-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-4-ol
(8Bs,13as)-3,6,7-trimethoxy-8b,9,11,12,13,13a-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-4-ol
Summary

SMILES: COc1cc2-c3c(C4=C[C@H]5N(C[C@@H]4c2cc1OC)CCC5)ccc(c3O)OC
InChI: InChI=1S/C23H25NO4/c1-26-19-7-6-14-15-9-13-5-4-8-24(13)12-18(15)16-10-20(27-2)21(28-3)11-17(16)22(14)23(19)25/h6-7,9-11,13,18,25H,4-5,8,12H2,1-3H3/t13-,18-/m0/s1
InChIKey: KXSJHSREHJDQJT-UGSOOPFHSA-N
DeepSMILES: COccc-ccC=C[C@H]NC[C@@H]6c%10cc%14OC)))))))CCC5)))))))cccc6O))OC
Scaffold Graph/Node/Bond level: C1=C2c3ccccc3-c3ccccc3C2CN2CCCC12
Scaffold Graph/Node level: C1CCC2C(C1)C1CCCCC1C1CN3CCCC3CC21
Scaffold Graph level: C1CC2CC3C4CCCCC4C4CCCCC4C3CC2C1
Functional groups: cOC; cC(=CC)C; CN(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
tyloindicine h, Tyloindicine H
External chemical identifiers:
CID:CID_373660; ChEMBL:CHEMBL1970992; ZINC:ZINC000005839269
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(8Bs,13as)-3,6,7-trimethoxy-8b,9,11,12,13,13a-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-4-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 379.46
Log P RDKit 4.04
Topological polar surface area (Å2) RDKit 51.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.39
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 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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(8Bs,13as)-3,6,7-trimethoxy-8b,9,11,12,13,13a-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-4-ol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.872164
(8Bs,13as)-3,6,7-trimethoxy-8b,9,11,12,13,13a-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-4-ol
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.22
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes