ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR107
Chemical Name : Para-coumaric acid
Plant Source : Carica papaya L.
Nutraceutical information : Edible, apple, pear, tomato, oat, onion, grape, wheat, potato, maize, beans, tomato, berries.
Mode of administration : Oral
Immunomodulatory mechanism : Antioxidant (inhibits lipid peroxidation, erectogenic enzymes, upregulates GST-M2 (glutathione S- transferase Mu 2), free radical scavenging, SOD, CAT (catalase), GSH, activates ARF/Nrf2 pathway); Anti-inflammatory (downregulates IL-6, TNF-α, IL-1β, inhibits NF-kb, upregulates IL-10, IL-4); Anti-cancer (upregulates Bcl-2, Bcl-xl, caspase-9, caspase-3, Bcl-xs, Bad, Bax, Mcl-1, G2/M phase cell cycle arrest, inhibits AKT/ERK signaling pathway); Anti-diabetic (downregulates TLR-4, TGF-β1, IL-6, inhibits alpha-glucosidase, upregulates phosphorylation of AMPK (AMP activated protein kinase), ACC (acetyl coa carboxylase), CPT-mrna (carnithine palmitoyltransferase-1), PRAR (peroxisome proliferator-activated receptor))
Description : P-coumaric acid is a phenolic secondary compound, the hydroxyl (-OH) group is responsible for attributing to its antioxidant property, it is a part of HCA (hydroxycinnamic acid) family. It is spread across the plant kingdom, found abundantly among the fruits, cereals, and vegetables. It is the most common isomer of coumaric acid and is formed using tyrosine and phenylalanine as precursors via shikimic pathway.

Chemical Structure Information

IUPAC Name (E)-3-(4-hydroxyphenyl)prop-2-enoic acid  
SMILES C1=CC(=CC=C1C=CC(=O)O)O
Formula C9H8O3
InchiKey NGSWKAQJJWESNS-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Phenylpropanoids and polyketides
Class Cinnamic acids and derivatives
Subclass Hydroxycinnamic acids and derivatives

Physicochemical properties

LogP 1.685
Molecular weight 164.158
Hydrogen Bond Acceptor 3
Hydrogen Bond Donor 2
Polar surface area 58.931
No. of rotatable bonds 2
Number of Aromatic Rings 1
Number of rings 1

ADMET Properties

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

Other Biological Properties

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References

    1. https://doi.org/10.13040/IJPSR.0975-8232.12(10).5229-37
    2. https://doi.org/10.3390/antiox10081205


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