pristimerin   Click here for help

GtoPdb Ligand ID: 13530

Synonyms: celastrol methyl ester
Compound class: Synthetic organic
Comment: Pristimerin is a naturally ocurring terpenoid compound that has been isolated from the seeds of the plant Celastrus paniculatus. It has been attributed with multiple biological activities, and is the subject of medicinal chemistry efforts to produce bioactive synthetic derivatives with therapeutic potential [2]. Molecular targets and mechanism of action are yet to be fully determined.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 1
Rotatable bonds 2
Topological polar surface area 63.6
Molecular weight 464.64
XLogP 8.3
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1=C(C(=O)C=C2C1=CC=C3[C@@]2(C)CC[C@@]4(C)[C@@H]5C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(=O)OC)O
Isomeric SMILES CC1=C(C(=O)C=C2C1=CC=C3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)OC)C)C)C)C)O
InChI InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1
InChI Key JFACETXYABVHFD-WXPPGMDDSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Chen Z, Zhang D, Yan S, Hu C, Huang Z, Li Z, Peng S, Li X, Zhu Y, Yu H et al.. (2019)
SAR study of celastrol analogs targeting Nur77-mediated inflammatory pathway.
Eur J Med Chem, 177: 171-187. [PMID:31132532]
2. Fu X, Jiao Y, Feng Y, Lin F, Zhang B, Mao Q, Wang J, Jiang W, Mou Y, Wang H et al.. (2024)
Scaffold Hopping of Pristimerin Provides Derivatives Containing a Privileged Quinoxaline Substructure as Potent Autophagy Inducers in Breast Cancer Cells.
J Nat Prod, 87 (8): 1952-1964. [PMID:39106494]
3. Ryu YB, Park SJ, Kim YM, Lee JY, Seo WD, Chang JS, Park KH, Rho MC, Lee WS. (2010)
SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii.
Bioorg Med Chem Lett, 20 (6): 1873-6. [PMID:20167482]
4. Xiong F, Ding X, Zhang H, Luo X, Chen K, Jiang H, Luo C, Xu H. (2021)
Discovery of novel reversible monoacylglycerol lipase inhibitors via docking-based virtual screening.
Bioorg Med Chem Lett, 41: 127986. [PMID:33766770]