celastrol   Click here for help

GtoPdb Ligand ID: 10386

Immunopharmacology Ligand
Comment: Celastrol is a plant-derived (from Tripterygium wilfordi, the Thunder god vine) natural product that has antioxidant, anti-inflammatory [1,6] and anti-obesity effects [3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 74.6
Molecular weight 450.28
XLogP 7.98
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C1C=C2C(=CC=C3C2(C)CCC2(C3(C)CCC3(C2CC(C)(CC3)C(=O)O)C)C)C(=C1O)C
Isomeric SMILES O=C1C=C2C(=CC=C3[C@@]2(C)CC[C@@]2([C@]3(C)CC[C@@]3([C@H]2C[C@@](C)(CC3)C(=O)O)C)C)C(=C1O)C
InChI InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
InChI Key KQJSQWZMSAGSHN-JJWQIEBTSA-N
References
1. Allison AC, Cacabelos R, Lombardi VR, Alvarez XA, Vigo C. (2001)
Celastrol, a potent antioxidant and anti-inflammatory drug, as a possible treatment for Alzheimer's disease.
Prog Neuropsychopharmacol Biol Psychiatry, 25 (7): 1341-57. [PMID:11513350]
2. Feng X, Guan D, Auen T, Choi JW, Salazar Hernández MA, Lee J, Chun H, Faruk F, Kaplun E, Herbert Z et al.. (2019)
IL1R1 is required for celastrol's leptin-sensitization and antiobesity effects.
Nat Med, 25 (4): 575-582. [PMID:30833749]
3. Pfuhlmann K, Schriever SC, Baumann P, Kabra DG, Harrison L, Mazibuko-Mbeje SE, Contreras RE, Kyriakou E, Simonds SE, Tiganis T et al.. (2018)
Celastrol-Induced Weight Loss Is Driven by Hypophagia and Independent From UCP1.
Diabetes, 67 (11): 2456-2465. [PMID:30158241]
4. Shi K, Chen X, Xie B, Yang SS, Liu D, Dai G, Chen Q. (2018)
Celastrol Alleviates Chronic Obstructive Pulmonary Disease by Inhibiting Cellular Inflammation Induced by Cigarette Smoke via the Ednrb/Kng1 Signaling Pathway.
Front Pharmacol, 9: 1276. [PMID:30498444]
5. Venkatesha SH, Moudgil KD. (2019)
Celastrol suppresses experimental autoimmune encephalomyelitis via MAPK/SGK1-regulated mediators of autoimmune pathology.
Inflamm Res, 68 (4): 285-296. [PMID:30820608]
6. Wong VKW, Qiu C, Xu SW, Law BYK, Zeng W, Wang H, Michelangeli F, Dias IRSR, Qu YQ, Chan TW et al.. (2019)
Ca2+ signalling plays a role in celastrol-mediated suppression of synovial fibroblasts of rheumatoid arthritis patients and experimental arthritis in rats.
Br J Pharmacol, 176 (16): 2922-2944. [PMID:31124139]
7. Zhan X, Yan C, Chen Y, Wei X, Xiao J, Deng L, Yang Y, Qiu P, Chen Q. (2018)
Celastrol antagonizes high glucose-evoked podocyte injury, inflammation and insulin resistance by restoring the HO-1-mediated autophagy pathway.
Mol Immunol, 104: 61-68. [PMID:30439604]
8. Zhang J, Zhou K, Zhang X, Zhou Y, Li Z, Shang F. (2019)
Celastrol Ameliorates Inflammation in Human Retinal Pigment Epithelial Cells by Suppressing NF-κB Signaling.
J Ocul Pharmacol Ther, 35 (2): 116-123. [PMID:30596540]
9. Zhou X, Cao X, Tu H, Zhang ZR, Deng L. (2019)
Inflammation-Targeted Delivery of Celastrol via Neutrophil Membrane-Coated Nanoparticles in the Management of Acute Pancreatitis.
Mol Pharm, 16 (3): 1397-1405. [PMID:30753778]