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) [6]. Andrographolide and analogues are being investigated for their potential anti-inflammatory activities [4], but andrographolide has also shown anti-viral, anti-thrombotic, hepatoprotective and anti-cancer properties [6]. 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 [3].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

andrographolide is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Behrens M, Brockhoff A, Batram C, Kuhn C, Appendino G, Meyerhof W. (2009)
The human bitter taste receptor hTAS2R50 is activated by the two natural bitter terpenoids andrographolide and amarogentin.
J Agric Food Chem, 57 (21): 9860-6. [PMID:19817411]
2. Fotsing JR, Darmohusodo V, Patron AP, Ching BW, Brady T, Arellano M, Chen Q, Davis TJ, Liu H, Servant G et al.. (2020)
Discovery and Development of S6821 and S7958 as Potent TAS2R8 Antagonists.
J Med Chem, 63 (9): 4957-4977. [PMID:32330040]
3. 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]
4. 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]
5. Roudnitzky N, Behrens M, Engel A, Kohl S, Thalmann S, Hübner S, Lossow K, Wooding SP, Meyerhof W. (2015)
Receptor Polymorphism and Genomic Structure Interact to Shape Bitter Taste Perception.
PLoS Genet, 11 (9): e1005530. [PMID:26406243]
6. 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]