ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR53
Chemical Name : Nobiletin
Plant Source : Citrus sps.
Nutraceutical information : Edible, High content in lemons, Mandarin orange (Citrus reticulata), Citrus depressa, sweet oranges.
Mode of administration : Oral, intraperitoneal
Immunomodulatory mechanism : Neuroprotective (activates ERK signaling pathway, reduces acetylcholinesterase (ache) levels, increased levels of glutathione peroxidase, manganese-superoxide dimutase, prevents camkii, MAP2, glur1 protein level reduction, prevents dopaminergic neuron damage against MPP+ toxicity); Antioxidant (inhibits ROS, lipid peroxidation, elevates GSH levels, downregulates SOD2, CYP51A1 genes); Apoptosis (downregulates BCL2 gene expression); interacts with ERK, CREB, P13K/AKT signaling pathways; Anti-cancer (arrest S, G2/M phase, downregulates Wnt pathway, CD44v6 marker, inhibits TGF-β, ZEB, Slug, Snail, oncogene factors STAT3, NF-κb, P13K, AKT, upregulates onco-suppressor factors microrna-7, 200b); Cardioprotective (activates ABCG2, AKR1B1)
Description : Nobiletin or 3′,4′,5,6,7,8-hexamethoxyflavone is a bioactive polymethoxylated flavones found in citrus fruits, with high absorption rate across cytoplasmic membrane credited to the lipophilic nature and its structure.

Chemical Structure Information

IUPAC Name 2-(3,4-dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one  
SMILES COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
Formula C21H22O8
InchiKey MRIAQLRQZPPODS-UHFFFAOYSA-N

Chemical Classification

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

Physicochemical properties

LogP 3.038
Molecular weight 402.395
Hydrogen Bond Acceptor 8
Hydrogen Bond Donor 0
Polar surface area 79.811
No. of rotatable bonds 7
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

  • Antidiabetic, anti-inflammatory, hepatoprotective, anti-obesity

References

    1. https://doi.org/10.1002/fft2.129
    2. https://doi.org/10.3390/ijms20143380
    3. https://doi.org/10.3390/ijms21155340
    4. https://doi.org/10.3390/cancers13163927
    5. https://doi:10.3390/biomedicines8050110


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