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 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 0.77766


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
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216117HMOX1800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.