celastrol   Click here for help

GtoPdb Ligand ID: 10386

Immunopharmacology Ligand
Compound class: Natural product or derivative
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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]