IMPPAT Phytochemical information: 
Piperlongumine

Piperlongumine
Summary

SMILES: COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc(c1OC)OC
InChI: InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChIKey: VABYUUZNAVQNPG-BQYQJAHWSA-N
DeepSMILES: COccc/C=C/C=O)NCCC=CC6=O))))))))))ccc6OC)))OC
Scaffold Graph/Node/Bond level: O=C1C=CCCN1C(=O)C=Cc1ccccc1
Scaffold Graph/Node level: OC1CCCCN1C(O)CCC1CCCCC1
Scaffold Graph level: CC1CCCCC1C(C)CCC1CCCCC1
Functional groups: cOC; c/C=C/C(=O)N1CCC=CC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
Synonymous chemical names:
piplartine, Piperlongumine, piperlongumine
External chemical identifiers:
CID:CID_637858; ChEMBL:CHEMBL465843; ChEBI:CHEBI:8241; ZINC:ZINC000000899053; FDASRS:SGD66V4SVJ; SureChEMBL:SCHEMBL173092; MolPort-001-741-398
Chemical structure download


Piperlongumine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 317.34
Log P RDKit 2.04
Topological polar surface area (Å2) RDKit 65.07
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
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 12
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 4
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Piperlongumine
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 0.77766


Piperlongumine
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 -6.77
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Piperlongumine
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_001705ENSG00000125618PAX87849ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_001644ENSG00000198431TXNRD17296ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001278ENSG00000205220PSMB105699ChEMBL
TAR_EXP_001467ENSG00000188130MAPK126300ChEMBL
TAR_EXP_001373ENSG00000239713APOBEC3G60489NPASS
TAR_EXP_001273ENSG00000100804PSMB55693ChEMBL
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001274ENSG00000142507PSMB65694ChEMBL
TAR_EXP_001275ENSG00000136930PSMB75695ChEMBL
TAR_EXP_001276ENSG00000235715PSMB85696ChEMBL
TAR_EXP_001277ENSG00000239836PSMB95698ChEMBL
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774ChEMBL, NPASS
TAR_EXP_001269ENSG00000277791PSMB35691ChEMBL
TAR_EXP_000877ENSG00000187098MITF4286ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000002ENSG00000117020AKT310000ChEMBL
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000174ENSG00000222028PSMB11122706ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000223ENSG00000154611PSMA8143471ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_000242ENSG00000168036CTNNB11499ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL
TAR_EXP_000475ENSG00000120948TARDBP23435ChEMBL, NPASS
TAR_EXP_000453ENSG00000118689FOXO32309BindingDB, ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001270ENSG00000159377PSMB45692ChEMBL
TAR_EXP_000983ENSG00000141458NPC14864NPASS
TAR_EXP_001179ENSG00000164830OXR155074ChEMBL
TAR_EXP_001267ENSG00000126067PSMB25690ChEMBL
TAR_EXP_000393ENSG00000105221AKT2208ChEMBL
TAR_EXP_001266ENSG00000008018PSMB15689ChEMBL
TAR_EXP_001265ENSG00000101182PSMA75688ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053ChEMBL, NPASS
TAR_EXP_001263ENSG00000143106PSMA55686ChEMBL
TAR_EXP_001262ENSG00000041357PSMA45685ChEMBL
TAR_EXP_001264ENSG00000100902PSMA65687ChEMBL
TAR_EXP_001260ENSG00000106588PSMA25683ChEMBL
TAR_EXP_001259ENSG00000129084PSMA15682ChEMBL
TAR_EXP_001239ENSG00000156711MAPK135603ChEMBL
TAR_EXP_001236ENSG00000185386MAPK115600ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001261ENSG00000100567PSMA35684ChEMBL