ImmunoCR
A repository of plant based immunomodulatory compounds
ImmunoCR
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Nutraceutical Profile

ImmunCR Id : ICR52
Chemical Name : Tangeretin
Plant Source : Citrus sps.
Nutraceutical information : Edible, High content in orange fruits and juices.
Mode of administration : Oral
Immunomodulatory mechanism : Renoprotective (attenuates serum creatinine, BUN, MDA level, upregulates Nrf2 signalling pathway, Keap1 pathway, NGAL (neutrophil gelatinase-associated lipocaline) pathway for renal injury or apoptosis); Anti-inflammatory (downregulates TNF-α, NF-κb, inos pathway, IL-6, IL-1β); Anti-tumor (mitochondrial dysfunction, inactivate caspase-3,9, cytochrome C, modulate Bax, Bcl-2, G2/M phase arrest, CYP1A1/CYP1B1 modulation of Tangeretin to 4-hydroxyl Tangeretin, deregulating STAT signalling pathway, suppresses PCNA, ki-67, COX-2, downregulates MMP-2, MMP-9, upregulates p53/p21); Neuroprotective (inhibits JNK, TNF-α, COX-2, inos signaling pathways, dopaminergic degeneration, upregulates PI3k/Akt signaling pathways); Antidiabetic (upregulates Bcl-2, SOD, CAT, GPX via inhibiting NF-Kb signaling pathway, inhibits ERK pathway); Hepatoprotective (upregulates HO-1, Nrf2, NQO-1, and MAPK pathways, increased GSH, GPX activity); Antiasthmatic (inhibit Notch-1 signal pathway); other immunomodulatory pathways (ZO-1, CXCL-8, ccl); Antioxidant ( upregulates SOD, CAT genes via Nrf2 signaling pathway)
Description : A flavonoid with a bitter taste found in citrus peel with multiple therapeutic effects.

Chemical Structure Information

IUPAC Name 5,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one  
SMILES COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC
Formula C20H20O7
InchiKey ULSUXBXHSYSGDT-UHFFFAOYSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Phenylpropanoids and polyketides
Class Flavonoids
Subclass O-methylated flavonoids

Physicochemical properties

LogP 3.054
Molecular weight 372.369
Hydrogen Bond Acceptor 7
Hydrogen Bond Donor 0
Polar surface area 70.881
No. of rotatable bonds 6
Number of Aromatic Rings 2
Number of rings 3

ADMET Properties

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

Other Biological Properties

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References

    1. https://doi.org/10.1002/fft2.129
    2. https://doi:10.1515/jbcpp-2019-0191 


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