IMPPAT Phytochemical information: 
(8Br,13ar)-2,3,6,7-tetramethoxy-8b,9,12,13-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-13a(11h)-ol
(8Br,13ar)-2,3,6,7-tetramethoxy-8b,9,12,13-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-13a(11h)-ol
Summary

SMILES: COc1cc2[C@H]3CN4CCC[C@]4(C=C3c3c(-c2cc1OC)cc(c(c3)OC)OC)O
InChI: InChI=1S/C24H27NO5/c1-27-20-8-14-15-9-21(28-2)23(30-4)11-17(15)19-13-25-7-5-6-24(25,26)12-18(19)16(14)10-22(20)29-3/h8-12,19,26H,5-7,13H2,1-4H3/t19-,24-/m1/s1
InChIKey: KKOZIXJFGMEJCY-NTKDMRAZSA-N
DeepSMILES: COccc[C@H]CNCCC[C@]5C=C9cc-c%13cc%17OC)))))cccc6)OC)))OC))))))))O
Scaffold Graph/Node/Bond level: C1=C2c3ccccc3-c3ccccc3C2CN2CCCC12
Scaffold Graph/Node level: C1CCC2C(C1)C1CCCCC1C1CN3CCCC3CC21
Scaffold Graph level: C1CC2CC3C4CCCCC4C4CCCCC4C3CC2C1
Functional groups: cOC; cC1=C[C@](O)(C)N(C)CC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
Synonymous chemical names:
Tyloindicine G, tyloindicine g
External chemical identifiers:
CID:CID_373659; ChEMBL:CHEMBL1984171; ZINC:ZINC000005839261; SureChEMBL:SCHEMBL8977404
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(8Br,13ar)-2,3,6,7-tetramethoxy-8b,9,12,13-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-13a(11h)-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 409.48
Log P RDKit 3.67
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 24
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 4
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
(8Br,13ar)-2,3,6,7-tetramethoxy-8b,9,12,13-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-13a(11h)-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 0.831639
(8Br,13ar)-2,3,6,7-tetramethoxy-8b,9,12,13-tetrahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinolin-13a(11h)-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 -6.72
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes