IMPPAT Phytochemical information: 
Pratorinine

Pratorinine
Summary

SMILES: COc1cc2c(cc1O)c1cccc3c1n(c2=O)cc3
InChI: InChI=1S/C16H11NO3/c1-20-14-8-12-11(7-13(14)18)10-4-2-3-9-5-6-17(15(9)10)16(12)19/h2-8,18H,1H3
InChIKey: BQBSEIUTJXPVJP-UHFFFAOYSA-N
DeepSMILES: COcccccc6O)))cccccc6nc%10=O))cc5
Scaffold Graph/Node/Bond level: O=c1c2ccccc2c2cccc3ccn1c32
Scaffold Graph/Node level: OC1C2CCCCC2C2CCCC3CCN1C32
Scaffold Graph level: CC1C2CCCCC2C2CCCC3CCC1C32
Functional groups: cO; cOC; c=O; cn(c)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Benzoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
pratorinine
Chemical structure download


Pratorinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 265.27
Log P RDKit 2.76
Topological polar surface area (Å2) RDKit 50.94
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
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 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 1
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


Pratorinine
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 0.538314


Pratorinine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -5.89
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No