ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR100
Chemical Name : Piperine
Plant Source : Piper cubeba
Nutraceutical information : Edible, Most common source is Black pepper
Mode of administration : Oral
Immunomodulatory mechanism : Anti-cancer (upregulates Bax, p53, inhibits Bcl-xl, cyclin A, suppresses ER, MMP-9, MMP-2, VEGF, c-Myc, IL-8, E-cadherin); Anti-diabetic (downregulates AST, ALT, alkaline phosphatase, NLRP3, TXNIP (thioredoxin-interacting protein) expression, MA (malondialdehyde), serum creatinine, proteinuria); Anti-obesity (reduces mrna expression (SREBP-1c, C/ebpβ, master adipogenic transcription factor, pparγ target genes), Ensures normal activity of lipid metabolic biomarkers (HMG-coa, FAS (fatty acid synthase), ACC (acetyl-coa carboxylase), LCAT (lecithin-cholesterol acyl transferase), CPT (carnithine palmitoyltransferase)), reduced oxidative stress); Cardioprotective (upregulates p27(kip1) expression, LCAT, CYP7A1, HMG-coa, LDL receptor, high density lipoprotein, mrna expression of cyclin D/E/PCNA), downregulates ERK1/2, inhibits ROS generation, p38 MAPK phosphorylation); Anti-aging (downregulates IL-8, caspase-3,9, upregulates acetylcholinestrase, maintains Bcl/Bax ratio); Anti-allergic (downregulates intracellular Ca2+, IL-4, TNF-α, IL-6, IL-1β, IL-13, inhibits release of (β-hexosaminidase, histamine), ige signaling pathways, phosphorylation of (Erk, Ras, p38, Lyn)); anti-inflammatory (downregulates IL-1β, IL-6, IL-10, TNF-α, TLR-4, TLR-2, inhibits NF-κb , I-κb, mapks, JNK, p65, ERK, p38); Hepatoprotective (downregulates expression of CTP1 gene(carnithine palmitoyl transferase 1), AST, ALT, IRS-1 (insulin substrate receptor-1) phosphorylation)
Description : Piperine is extracted from multiple plants of Piper species, it is an alkaloid and is extensively studied for its many therapeutic potentials. Due to its ability to metabolize enzymes it is also used to enhance bioavailability of other drugs as well.

Chemical Structure Information

IUPAC Name (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one 
SMILES C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3  
Formula C17H19NO3
InchiKey MXXWOMGUGJBKIW-YPCIICBESA-N

Chemical Classification

Kingdom Organic compounds
Superclass Alkaloids and derivatives
Class ---
Subclass ---

Physicochemical properties

LogP 2.864
Molecular weight 285.338
Hydrogen Bond Acceptor 3
Hydrogen Bond Donor 0
Polar surface area 38.513
No. of rotatable bonds 3
Number of Aromatic Rings 1
Number of rings 3

ADMET Properties

Absorption level Good
Solubility level Very Soluble
Blood Brain Barrier High
Plasma protein binding Binder
CYP2D6 inhibition Non-Inhibitor

Other Biological Properties

  • ---

References

    1. https://doi.org/10.13040/IJPSR.0975-8232.12(10).5229-37
    2. https://doi.org/10.1002/ptr.6855


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