IMPPAT Phytochemical information: 
Coumaperine

Coumaperine
Summary

SMILES: Oc1ccc(cc1)/C=C/C=C/C(=O)N1CCCCC1
InChI: InChI=1S/C16H19NO2/c18-15-10-8-14(9-11-15)6-2-3-7-16(19)17-12-4-1-5-13-17/h2-3,6-11,18H,1,4-5,12-13H2/b6-2+,7-3+
InChIKey: QDAARMDLSCDBFU-YPCIICBESA-N
DeepSMILES: Occcccc6))/C=C/C=C/C=O)NCCCCC6
Scaffold Graph/Node/Bond level: O=C(C=CC=Cc1ccccc1)N1CCCCC1
Scaffold Graph/Node level: OC(CCCCC1CCCCC1)N1CCCCC1
Scaffold Graph level: CC(CCCCC1CCCCC1)C1CCCCC1
Functional groups: cO; c/C=C/C=C/C(=O)N(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Piperidines
ClassyFire Subclass: N-acylpiperidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
n-5-(4-hydroxy-phenyl)-2e,4e-pentadienoylpiperidine
External chemical identifiers:
CID:CID_10131321; ChEMBL:CHEMBL4061010; ChEBI:CHEBI:169029; FDASRS:6M586HW0PD; SureChEMBL:SCHEMBL4919407
Chemical structure download


Coumaperine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 257.33
Log P RDKit 2.97
Topological polar surface area (Å2) RDKit 40.54
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 3
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 11
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Coumaperine
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 0.667742


Coumaperine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.72
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No