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
• #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: CHEBI:28821
  CAS Number: 94-62-2
  DrugBank ID: DB12582
  TTD ID: D0H7PW

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
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[3]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[4]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[4]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[5]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Protein Interaction/Cellular Processes	[4]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Protein Interaction/Cellular Processes	[4]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Gene/Protein Processing	[4]
Cyclic AMP-dependent transcription factor ATF-2 (ATF2)	OTNIZPEA	ATF2_HUMAN	Protein Interaction/Cellular Processes	[3]
Cyclic AMP-responsive element-binding protein 1 (CREB1)	OT1MDLA1	CREB1_HUMAN	Protein Interaction/Cellular Processes	[3]
Cytochrome c (CYCS)	OTBFALJD	CYC_HUMAN	Protein Interaction/Cellular Processes	[4]

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

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 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.
• [4] 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.
• [5] 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.