andrographolide   Click here for help

GtoPdb Ligand ID: 9675

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Andrographolide is a major component of the leaves of the traditionally used medicinal plant Andrographis paniculata (Acanthaceae) [3]. Andrographolide and analogues are being investigated for their potential anti-inflammatory activities [2], but andrographolide has also shown anti-viral, anti-thrombotic, hepatoprotective and anti-cancer properties [3]. Accumulated evidence indicates that the principal mechanism undelying andrographolide's anti-inflammatory action is inhibition of NF-κB. Additional studies show that Nrf2 activation by andrographolide likely enhances endogenous antioxidant defense mechanisms. Direct covalent interaction with Cys62, and non-covalent binding are both required for andrographolide-induced inhibition of NF-κB p50 [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 86.99
Molecular weight 350.21
XLogP 2.91
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC1(C)C(O)CCC2(C1CCC(=C)C2CC=C1C(O)COC1=O)C
Isomeric SMILES OC[C@]1(C)[C@H](O)CC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C/1\[C@H](O)COC1=O)C
InChI InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
InChI Key BOJKULTULYSRAS-OTESTREVSA-N
References
1. Nguyen VS, Loh XY, Wijaya H, Wang J, Lin Q, Lam Y, Wong WS, Mok YK. (2015)
Specificity and inhibitory mechanism of andrographolide and its analogues as antiasthma agents on NF-κB p50.
J Nat Prod, 78 (2): 208-17. [PMID:25615020]
2. Peng S, Gao J, Liu W, Jiang C, Yang X, Sun Y, Guo W, Xu Q. (2016)
Andrographolide ameliorates OVA-induced lung injury in mice by suppressing ROS-mediated NF-κB signaling and NLRP3 inflammasome activation.
Oncotarget, 7 (49): 80262-80274. [PMID:27793052]
3. Tan WSD, Liao W, Zhou S, Wong WSF. (2017)
Is there a future for andrographolide to be an anti-inflammatory drug? Deciphering its major mechanisms of action.
Biochem Pharmacol, 139: 71-81. [PMID:28377280]