ImmunoCR
A repository of plant based immunomodulatory compounds
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Nutraceutical Profile

ImmunCR Id : ICR87
Chemical Name : Celastrol
Plant Source : Tripterygium wilford II
Nutraceutical information : ---
Mode of administration : Oral
Immunomodulatory mechanism : Anti-obesity (leptin sensitizer, upregulates STAT3 pathway, AGRP (Agouti-related peptide), reduced PERK phosphorylation (lower ER stress), ALT, AST, inhibits NF-κb, HSP90); Anti-inflammatory (inhibits NF-κb, ikkα, ikkβ, downregulates TGF-β, upregulates IL-10, activates caspase-3, JNK, ERK, p38 MAPK pathways); Anti-cancer (increases iκb-α, p27, Bax via inhibition of proteasomes, regulates P13K/Akt/mtor pathway, inhibits HIF-1, topoisomerase II); Neuroprotective (inhibits ROS production, MHC-II expression, lipid peroxidation, regulates BACE-1, downregulates CD40, TNF-α, GFAP, inos); Anti-atherosclerotic (inhibits LOX-1, ROS production, downregulates P-selectin, glycoprotein iib/iiia, VEGF expression); Antioxidant (regulates HO-1, gsts, NADP(H), NQO1, Nrf2 pathway, reduces inos, NO); Anti-angiogenesis (inhibits VEGF induced Akt/mtor/p70s6 K signaling, HIF-1α, Hsp90, Akt/enos signaling, ICAM-1, VCAM-1, suppresses TLR4 mediated NF-kb activation, VEGFR-1, VEGFR-2)
Description : Celastrol, (9b,13a,14b,20a)-3-hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid is a pentacyclic triterpenoid compound obtained from roots of thunder god vine. It has a pale brown to orange crystalline presence with high solubility in non polar compounds like ethanol, DMSO.

Chemical Structure Information

IUPAC Name (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid 
SMILES CC1=C(C(=O)C=C2C1=CC=C3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C)O
Formula C29H38O4
InchiKey KQJSQWZMSAGSHN-UHFFFAOYSA-N

Chemical Classification

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

Physicochemical properties

LogP 5.475
Molecular weight 450.61
Hydrogen Bond Acceptor 4
Hydrogen Bond Donor 2
Polar surface area 76.232
No. of rotatable bonds 1
Number of Aromatic Rings 0
Number of rings 5

ADMET Properties

Absorption level Moderate
Solubility level Very Soluble
Blood Brain Barrier Undefined
Plasma protein binding Non-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.cell.2015.05.011
    3. https://doi:10.1016/j.bbrc.2010.03.050 


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