oridonin   Click here for help

GtoPdb Ligand ID: 13088

Synonyms: lasidonin | rubescensin A
Compound class: Natural product or derivative
Comment: Oridonin is a plant-derived terpenoid. It has been identified as an active ingredient in species including Rabdosia rubescens (Chinese sage) [12], Isodon rugosus and Isodon ternifolius. Oridonin is proposed to exhibit a wide range of pharmacological properties, including antineoplastic, anti-angiogenic, pro-apoptotic, anti-asthmatic, anti-inflammatory and anti-bacterial actions [1]. Rabdosia rubescens root extract has been used in traditional Chinese medicine to treat inflammatory diseases and oral cancer.
The dissection of oridonin's specific mechanism of action and identification of its molecular target(s) is ongoing. In respect of inflammation, oridonin binds covalently to NLRP3 and blocks its interaction with NEK7, which ultimately prevents NLRP3 inflammasone assembly and activation [2]. It does not suppress activation of NLRC4 or AIM2 inflammasomes. Oridonin also inhibits AKT serine/threonine kinases in vitro, which may be associated with its anti-tumour activity [8-9].
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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
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 6
Hydrogen bond donors 4
Rotatable bonds 0
Topological polar surface area 107.22
Molecular weight 364.43
XLogP 0.25
No. Lipinski's rules broken 0
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 C=C1[C@@H]2CC[C@H]3[C@]45CO[C@]([C@H]([C@@H]5C(C)(C)CC[C@@H]4O)O)([C@@]3(C1=O)[C@@H]2O)O
Isomeric SMILES CC1(CC[C@@H]([C@]23[C@@H]1[C@@H]([C@]([C@]45[C@H]2CC[C@H]([C@H]4O)C(=C)C5=O)(OC3)O)O)O)C
InChI InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1
InChI Key SDHTXBWLVGWJFT-XKCURVIJSA-N
Classification Click here for help
Compound class Natural product or derivative
Synonyms Click here for help
lasidonin | rubescensin A
Database Links Click here for help
BindingDB Ligand 50605174
CAS Registry No. 28957-04-2 (source: PubChem)
ChEBI CHEBI:138236
ChEMBL Ligand CHEMBL1164920
GtoPdb PubChem SID 491299870
PubChem CID 5321010
Search Google for chemical match using the InChIKey SDHTXBWLVGWJFT-XKCURVIJSA-N
Search Google for chemicals with the same backbone SDHTXBWLVGWJFT
UniChem Compound Search for chemical match using the InChIKey SDHTXBWLVGWJFT-XKCURVIJSA-N
UniChem Connectivity Search for chemical match using the InChIKey SDHTXBWLVGWJFT-XKCURVIJSA-N