ImmunoCR
A repository of plant based immunomodulatory compounds
ImmunoCR
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Nutraceutical Profile

ImmunCR Id : ICR35
Chemical Name : Chlorogenic acid
Plant Source : Malus domestica
Nutraceutical information : Edible, apples, pears, carrots, tomatoes, coffee and sweet potatoes
Mode of administration : OraL, Liquid
Immunomodulatory mechanism : Inhibit glucose 6-phosphate hydrolysis, inhibitor of Hepatic Glucose-6-phosphate translocase; potent antioxidants found in certain foods and drinks, most notably in coffee. Anti-hypertension effect: blood-pressure reduction through improved endothelial function and nitric oxide bioavailability in the arterial vasculature. Reduce the relative risks of type 2 diabetes,4, 5 obesity,6 Alzheimer's disease,7, 8 eclampsia and stroke; found in:eucommia ulmoides and honeysuckle, coffee, black and green tea, Mate, cocoa, Pome fruits:(apple, pear), berry fruits, grapes and wines, citrus fruits, stone fruits, Brassicas (kale, cabbage and Brussels sprouts), Chenopodiaceae – spinach and beetroot, Asteraceae, potato tubers, tomato, pineapple, cereals, beer, wheat, pulses and legumes; antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension, free radicals scavenger and a central nervous system (CNS) stimulator.; could reverse HFD-induced activation of TLR4 signaling pathway and expression of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in liver. Meanwhile, CGA increased the content of Bifidobacterium and reduced the content of Escherichia coli in feces. Furthermore, CGA could increase the expression of tight junction proteins Occludin and zonula occludens-1 (ZO-1) in intestinal tissue. Moreover, CGA could the level of LPS and increased the level of GLP-1 in portal vein. These results indicated that CGA protected against HFD-induced hepatic steatosis and inflammation probably through its anti-inflammatory effects associated with regulation of gut microbiota and an increase of GLP-1 secretion and thus could be used as a potential drug for prevention and treatment of NAFLD; alkyl peroxyl radical (ROO•) scavenging property
Description : It is an ester between quinic acid (1 l—1 [OH], 3, 4/5-tetrahydroxycyclohexane carboxylic acid) and trans-cinnamic acid (such as caffeic, ferulic and coumaric acid).

Chemical Structure Information

IUPAC Name (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid  
SMILES C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
Formula C16H18O9
InchiKey CWVRJTMFETXNAD-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Organic oxygen compounds
Class Organooxygen compounds
Subclass Alcohols and polyols

Physicochemical properties

LogP -0.34
Molecular weight 354.309
Hydrogen Bond Acceptor 9
Hydrogen Bond Donor 6
Polar surface area 168.424
No. of rotatable bonds 5
Number of Aromatic Rings 1
Number of rings 2

ADMET Properties

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

Other Biological Properties

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References

    1. https://doi.org/10.1002/fft2.129
    2. https://doi.org/10.1021/jm9607360
    3. https://doi.org/10.1038/hr.2011.195
    4. https://doi:10.1002/(sici)1097-0010(19990301)79:3<362::aid-jsfa256>3.0.co;2-d
    5. https://doi: 10.3389/fphar.2021.693048.


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