andrographolide

Ligand id: 9675

Name: andrographolide

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Comments
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].
Database Links
BindingDB Ligand 50084419
GtoPdb PubChem SID 348353634
PubChem CID 5318517
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