IMPPAT Phytochemical information: 
Perloline

Perloline
Summary

SMILES: COc1cc(ccc1OC)[n+]1cc2c(=O)[nH]ccc2c2c1cccc2
InChI: InChI=1S/C20H16N2O3/c1-24-18-8-7-13(11-19(18)25-2)22-12-16-14(9-10-21-20(16)23)15-5-3-4-6-17(15)22/h3-12H,1-2H3/p+1
InChIKey: OWAVOYPOZCUWDT-UHFFFAOYSA-O
DeepSMILES: COcccccc6OC)))))[n+]ccc=O)[nH]ccc6cc%10cccc6
Scaffold Graph/Node/Bond level: O=c1[nH]ccc2c1c[n+](-c1ccccc1)c1ccccc21
Scaffold Graph/Node level: OC1NCCC2C1CN(C1CCCCC1)C1CCCCC21
Scaffold Graph level: CC1CCCC2C1CC(C1CCCCC1)C1CCCCC21
Functional groups: cOC; c-[n+](c)c; c=O; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Phenylquinolines
Synonymous chemical names:
perloline, Perloline
External chemical identifiers:
CID:CID_115025
Chemical structure download


Perloline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 333.37
Log P RDKit 2.98
Topological polar surface area (Å2) RDKit 55.2
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
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 18
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
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


Perloline
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 0.463154


Perloline
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 -5.97
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes