Details of the Drug

General Information of Drug (ID: DMYEAB1)

Drug Name
PIPERINE
Synonyms
piperine; 94-62-2; 1-Piperoylpiperidine; Piperin; Bioperine; Piperoylpiperidine; (E,E)-1-piperoylpiperidine; N-[(E,E)-Piperoyl]piperidine; Piperidine, 1-piperoyl-, (E,E)-; UNII-U71XL721QK; FEMA No. 2909; CCRIS 5572; Piperine (aliphatic); 1-Piperoylpiperidine, (E,E)-; 7780-20-3; C17H19NO3; EINECS 202-348-0; NSC 21727; 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine; N-(E,E)-piperoyl-piperidine; CHEMBL43185; U71XL721QK; CHEBI:28821; MXXWOMGUGJBKIW-YPCIICBESA-N; NSC21727; piperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)
Indication
Disease Entry ICD 11 Status REF
Vitiligo ED63.0 Phase 1/2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 285.34
Logarithm of the Partition Coefficient (xlogp) 3.5
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C17H19NO3
IUPAC Name
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
Canonical SMILES
C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
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
Cross-matching ID
PubChem CID
638024
ChEBI ID
CHEMBL43185
CAS Number
94-62-2
UNII
U71XL721QK
DrugBank ID
DB12582
TTD ID
D0H7PW
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Monoamine oxidase type A (MAO-A) TT3WG5C AOFA_HUMAN Inhibitor [2]
Monoamine oxidase type B (MAO-B) TTGP7BY AOFB_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [3]
Cyclic AMP-dependent transcription factor ATF-2 (ATF2) OTNIZPEA ATF2_HUMAN Protein Interaction/Cellular Processes [4]
Cytochrome c (CYCS) OTBFALJD CYC_HUMAN Protein Interaction/Cellular Processes [5]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Protein Interaction/Cellular Processes [5]
Nuclear factor NF-kappa-B p105 subunit (NFKB1) OTNRRD8I NFKB1_HUMAN Protein Interaction/Cellular Processes [4]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [6]
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Protein Interaction/Cellular Processes [4]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Protein Interaction/Cellular Processes [4]
UDP-glucose 6-dehydrogenase OTZS0T6O UGDH_HUMAN Gene/Protein Processing [7]
Utrophin OT7TZ637 UTRN_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Vitiligo
ICD Disease Classification ED63.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Monoamine oxidase type B (MAO-B) DTT MAOB 2.65E-02 1.12E-02 0.07
Monoamine oxidase type A (MAO-A) DTT MAOA 8.14E-01 0.05 0.1
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2489).
2 Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases. Bioorg Med Chem Lett. 2010 Jan 15;20(2):537-40.
3 Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1. Toxicol Appl Pharmacol. 2013 Oct 1;272(1):96-107.
4 Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells. Int Immunopharmacol. 2004 Dec 20;4(14):1795-803. doi: 10.1016/j.intimp.2004.08.005.
5 Targeting hepatocellular carcinoma with piperine by radical-mediated mitochondrial pathway of apoptosis: an initro and inivo study. Food Chem Toxicol. 2017 Jul;105:106-118.
6 Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
7 Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression. J Biochem Mol Toxicol. 2005;19(5):279-88. doi: 10.1002/jbt.20099.
8 Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening. PLoS One. 2011;6(10):e26169. doi: 10.1371/journal.pone.0026169. Epub 2011 Oct 20.