salvianolic acid A   Click here for help

GtoPdb Ligand ID: 13093

Synonyms: Dan Phenolic Acid A | Danshen | Sal A
Immunopharmacology Ligand
Compound class: Natural product
Comment: Salvianolic acid A is a plant-derived stilbenoid. A number of salvianolic acids have been extracted from a range of plants, some of which are used in Chinese herbal medicines (e.g. Danshen, Salvia miltiorrhiza). The therapeutic potential of salvianolic acids is under investigation [4], based on their proposed pharmacological effects which include anti-oxidant, anti-fibrotic, anti-coagulant/anti-thrombotic and anti-tumour activities [6-7].
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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.

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View interactive charts of activity data across species

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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 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.

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Hydrogen bond acceptors 10
Hydrogen bond donors 7
Rotatable bonds 9
Topological polar surface area 184.98
Molecular weight 494.45
XLogP 2.63
No. Lipinski's rules broken 1

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
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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.

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/)

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Canonical SMILES C(=C\C1=C(C(=CC=C1/C=C/C(=O)O[C@H](CC2=CC=C(C(=C2)O)O)C(=O)O)O)O)/C3=CC=C(C(=C3)O)O
Isomeric SMILES C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C/2=C(\C(=C(C=C2)O)O)/C=C/C3=CC(=C(C=C3)O)O)O)O
InChI InChI=1S/C26H22O10/c27-18-7-2-14(11-21(18)30)1-6-17-16(4-9-20(29)25(17)33)5-10-24(32)36-23(26(34)35)13-15-3-8-19(28)22(31)12-15/h1-12,23,27-31,33H,13H2,(H,34,35)/b6-1+,10-5+/t23-/m1/s1
InChI Key YMGFTDKNIWPMGF-UCPJVGPRSA-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. Chen J, Ruan Z, Lou H, Yang D, Shao R, Xu Y, Hu X, Jiang B. (2022)
First-in-human study to investigate the safety and pharmacokinetics of salvianolic acid A and pharmacokinetic simulation using a physiologically based pharmacokinetic model.
Front Pharmacol, 13: 907208. [PMID:36408276]
2. Karioti A, Ceruso M, Carta F, Bilia AR, Supuran CT. (2015)
New natural product carbonic anhydrase inhibitors incorporating phenol moieties.
Bioorg Med Chem, 23 (22): 7219-25. [PMID:26498393]
3. Lü S, Deng J, Liu H, Liu B, Yang J, Miao Y, Li J, Wang N, Jiang C, Xu Q et al.. (2018)
PKM2-dependent metabolic reprogramming in CD4+ T cells is crucial for hyperhomocysteinemia-accelerated atherosclerosis.
J Mol Med (Berl), 96 (6): 585-600. [PMID:29732501]
4. Ma L, Tang L, Yi Q. (2019)
Salvianolic Acids: Potential Source of Natural Drugs for the Treatment of Fibrosis Disease and Cancer.
Front Pharmacol, 10: 97. [PMID:30842735]
5. Shirai T, Nazarewicz RR, Wallis BB, Yanes RE, Watanabe R, Hilhorst M, Tian L, Harrison DG, Giacomini JC, Assimes TL et al.. (2016)
The glycolytic enzyme PKM2 bridges metabolic and inflammatory dysfunction in coronary artery disease.
J Exp Med, 213 (3): 337-54. [PMID:26926996]
6. Ye Z, Liu Y, Song J, Gao Y, Fang H, Hu Z, Zhang M, Liao W, Cui L, Liu Y. (2023)
Expanding the therapeutic potential of Salvia miltiorrhiza: a review of its pharmacological applications in musculoskeletal diseases.
Front Pharmacol, 14: 1276038. [PMID:38116081]
7. Zhu J, Chen H, Le Y, Guo J, Liu Z, Dou X, Lu D. (2022)
Salvianolic acid A regulates pyroptosis of endothelial cells via directly targeting PKM2 and ameliorates diabetic atherosclerosis.
Front Pharmacol, 13: 1009229. [PMID:36425580]