ImmunoCR
A repository of plant based immunomodulatory compounds
ImmunoCR
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Nutraceutical Profile

ImmunCR Id : ICR78
Chemical Name : Carnosic acid
Plant Source : Rosmarinus officinalis
Nutraceutical information : Rosmarinus officinalis, Salvia officinalis
Mode of administration : ---
Immunomodulatory mechanism : Antioxidant (ROS (reactive oxygen species) scavenger, downregulate hydroperoxide formation in fatty acids); Antimicrobial (active against Gram negative and Gram positive bacteria); Anti-inflammatory (inhibits NF-κb, upregulates HO-1, NRF2 expression, downregulates TNF-α, NO); Neuroprotective (downregulate IL-1β, IL-6, NO (nitric oxide), inhibits NLRP3 activation, activates KEAP1/NRF2 pathway)
Description : Carnosic acid has a lipophilic structure and is a phenolic diterpene containing a single phenol group, also contains two hydroxyl groups at ortho positions C11, C12, first extracted from Salvia officinalis with more abundance of trichome along with it in the leaves. The hot and harsh enviornmental factors affect the carnosic acid levels in the plant leaves.

Chemical Structure Information

IUPAC Name (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid  
SMILES CC(C)C1=C(C(=C2C(=C1)CC[C@@H]3[C@@]2(CCCC3(C)C)C(=O)O)O)O
Formula C20H28O4
InchiKey QRYRORQUOLYVBU-VBKZILBWSA-N

Chemical Classification

Kingdom Organic compounds
Superclass Lipids and lipid-like molecules
Class Prenol lipids
Subclass Diterpenoids

Physicochemical properties

LogP 4.905
Molecular weight 332.434
Hydrogen Bond Acceptor 4
Hydrogen Bond Donor 3
Polar surface area 79.747
No. of rotatable bonds 2
Number of Aromatic Rings 1
Number of rings 3

ADMET Properties

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

Other Biological Properties

  • ---

References

    1. https://doi: 10.1016/B978-0-12-394591-4.00004-0
    2. https://doi.org/10.1016/j.phytochem.2014.12.026
    3. https://doi.org/10.3390/antiox11010124


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