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
Immunopharmacology Comments
Andrographolide has anti-inflammatory activity, likely via inhibition of NF-κB p50 [1].