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
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 0.632788
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL, NPASS
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000350ENSG00000106546AHR196ChEMBL, NPASS
TAR_EXP_000311ENSG00000102967DHODH1723BindingDB, ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL, NPASS
TAR_EXP_000521ENSG00000022355GABRA12554BindingDB, ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_001171ENSG00000132170PPARG5468NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_000983ENSG00000141458NPC14864ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_000248ENSG00000117984CTSD1509BindingDB, ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001547ENSG00000275349SMN16606ChEMBL, NPASS
TAR_EXP_001549ENSG00000166311SMPD16609NPASS
TAR_EXP_001557ENSG00000012048BRCA1672ChEMBL, NPASS
TAR_EXP_001670ENSG00000196689TRPV17442BindingDB, ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB
TAR_EXP_001684ENSG00000104267CA2760BindingDB
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599NPASS