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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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 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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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 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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(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
Database Links Click here for help
BindingDB Ligand 50084419
GtoPdb PubChem SID 348353634
PubChem CID 5318517
Search Google for chemical match using the InChIKey BOJKULTULYSRAS-OTESTREVSA-N
Search Google for chemicals with the same backbone BOJKULTULYSRAS
UniChem Compound Search for chemical match using the InChIKey BOJKULTULYSRAS-OTESTREVSA-N
UniChem Connectivity Search for chemical match using the InChIKey BOJKULTULYSRAS-OTESTREVSA-N