oridonin   Click here for help

GtoPdb Ligand ID: 13088

Synonyms: lasidonin | rubescensin A
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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2D Structure
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Physico-chemical Properties
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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
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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
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
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