IMPPAT Phytochemical information: 
Piperine
Piperine
Summary

SMILES: O=C(N1CCCCC1)/C=C/C=C/c1ccc2c(c1)OCO2
InChI: InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
InChIKey: MXXWOMGUGJBKIW-YPCIICBESA-N
DeepSMILES: O=CNCCCCC6))))))/C=C/C=C/cccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C(C=CC=Cc1ccc2c(c1)OCO2)N1CCCCC1
Scaffold Graph/Node level: OC(CCCCC1CCC2OCOC2C1)N1CCCCC1
Scaffold Graph level: CC(CCCCC1CCC2CCCC2C1)C1CCCCC1
Functional groups: c/C=C/C=C/C(=O)N(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
piperin, piperine, Piperine
External chemical identifiers:
CID:CID_638024; ChEMBL:CHEMBL43185; ChEBI:CHEBI:28821; ZINC:ZINC000001529772; FDASRS:U71XL721QK; SureChEMBL:SCHEMBL94058; MolPort-001-759-210
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Piperine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 285.34
Log P RDKit 3
Topological polar surface area (Å2) RDKit 38.77
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 21
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 11
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
Piperine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63
Piperine
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 -5.58
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Piperine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000295025REL700
ENSP00000296871CSF2700
ENSP00000306245FOS700
ENSP00000336528NR1I2700
ENSP00000387699CREB1700
ENSP00000382659TRPV1918
ENSP00000384273RELA700
ENSP00000269571ERBB2800
ENSP00000398698TNF725
ENSP00000459962848
ENSP00000356436PLA2G4A800
ENSP00000265724ABCB1859
ENSP00000301645CYP7A1800
ENSP00000263341IL1B700
ENSP00000260302MMP13815
ENSP00000258743IL6725
ENSP00000264110ATF2700
ENSP00000226574NFKB1700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.