IMPPAT Phytochemical information: 
Taliscanine

Taliscanine
Summary

SMILES: COc1cc2C(=O)Nc3c2c(c1OC)c1cccc(c1c3)OC
InChI: InChI=1S/C18H15NO4/c1-21-13-6-4-5-9-10(13)7-12-15-11(18(20)19-12)8-14(22-2)17(23-3)16(9)15/h4-8H,1-3H3,(H,19,20)
InChIKey: DCWZBQMWCAMEEF-UHFFFAOYSA-N
DeepSMILES: COcccC=O)Ncc5cc9OC)))cccccc6c%10))OC
Scaffold Graph/Node/Bond level: O=C1Nc2cc3ccccc3c3cccc1c23
Scaffold Graph/Node level: OC1NC2CC3CCCCC3C3CCCC1C23
Scaffold Graph level: CC1CC2CC3CCCCC3C3CCCC1C23
Functional groups: cOC; cNC(=O)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aristolactams
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids
Synonymous chemical names:
taliscanine, Taliscanine
External chemical identifiers:
CID:CID_10859838
Chemical structure download


Taliscanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.32
Log P RDKit 3.58
Topological polar surface area (Å2) RDKit 56.79
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Taliscanine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.751293


Taliscanine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.88
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No