salvianolic acid B   Click here for help

GtoPdb Ligand ID: 13515

Synonyms: danfensuan B | SalB
Compound class: Natural product
Comment: Salvianolic acid B 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 [9], based on their proposed pharmacological effects which include anti-oxidant, anti-fibrotic, anti-coagulant/anti-thrombotic, anti-inflammatory and anti-tumour activities [2-3,13,16-17]. Specifically, salvianolic acid B is reported to directly interact with the platelet-derived growth factor receptor β (PDGFRβ) [6], which is a well established fibrosis target that is expressed by hepatic stellate cells [1,8,14-15]. Inhibition of lysine-specific demethylase 1 (LSD1; KDM1A, an anticancer target) has also been reported [4].
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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 16
Hydrogen bond donors 9
Rotatable bonds 14
Topological polar surface area 278.04
Molecular weight 718.62
XLogP 1.68
No. Lipinski's rules broken 4

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 C1=C(C=C(C(=C1)O)O)C[C@H](C(=O)O)OC(=O)/C=C/C2=CC=C(C3=C2[C@@H]([C@@H](C4=CC=C(C(=C4)O)O)O3)C(=O)O[C@H](CC5=CC=C(C(=C5)O)O)C(=O)O)O
Isomeric SMILES C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C3[C@@H]([C@H](OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O[C@H](CC5=CC(=C(C=C5)O)O)C(=O)O)O)O
InChI InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1
InChI Key SNKFFCBZYFGCQN-VWUOOIFGSA-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. Bonner JC. (2004)
Regulation of PDGF and its receptors in fibrotic diseases.
Cytokine Growth Factor Rev, 15 (4): 255-73. [PMID:15207816]
2. Chen SC, Lin YL, Huang B, Wang DL, Cheng JJ. (2011)
Salvianolic acid B suppresses IFN-γ-induced JAK/STAT1 activation in endothelial cells.
Thromb Res, 128 (6): 560-4. [PMID:21992896]
3. Chen YL, Hu CS, Lin FY, Chen YH, Sheu LM, Ku HH, Shiao MS, Chen JW, Lin SJ. (2006)
Salvianolic acid B attenuates cyclooxygenase-2 expression in vitro in LPS-treated human aortic smooth muscle cells and in vivo in the apolipoprotein-E-deficient mouse aorta.
J Cell Biochem, 98 (3): 618-31. [PMID:16440326]
4. Fu DJ, Li J, Yu B. (2021)
Annual review of LSD1/KDM1A inhibitors in 2020.
Eur J Med Chem, 214: 113254. [PMID:33581557]
5. Lin Y, Han C, Xu Q, Wang W, Li L, Zhu D, Luo J, Kong L. (2020)
Integrative countercurrent chromatography for the target isolation of lysine-specific demethylase 1 inhibitors from the roots of Salvia miltiorrhiza.
Talanta, 206: 120195. [PMID:31514831]
6. Liu F, Li S, Chen P, Gu Y, Wang S, Wang L, Chen C, Wang R, Yuan Y. (2023)
Corrigendum to "Salvianolic acid B inhibits hepatic stellate cell activation and liver fibrosis by targeting PDGFRβ" [Int. Immunopharmacol. 122 (2023) 110550].
Int Immunopharmacol, 123: 110790. [PMID:37640621]
7. Liu F, Li S, Chen P, Gu Y, Wang S, Wang L, Chen C, Wang R, Yuan Y. (2023)
Salvianolic acid B inhibits hepatic stellate cell activation and liver fibrosis by targeting PDGFRβ.
Int Immunopharmacol, 122: 110550. [PMID:37451016]
8. Luo H, Zhao F, Zhang F, Liu N. (2018)
Influence of amygdalin on PDG, IGF and PDGFR expression in HSC-T6 cells.
Exp Ther Med, 15 (4): 3693-3698. [PMID:29556259]
9. 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]
10. Murata I, Sugai T, Murakawa Y, Miyamoto Y, Kobayashi J, Inoue Y, Kanamoto I. (2022)
Salvianolic acid B improves the survival rate, acute kidney dysfunction, inflammation and NETosis-mediated antibacterial action in a crush syndrome rat model.
Exp Ther Med, 23 (5): 320. [PMID:35386617]
11. Tang MK, Ren DC, Zhang JT, Du GH. (2002)
Effect of salvianolic acids from Radix Salviae miltiorrhizae on regional cerebral blood flow and platelet aggregation in rats.
Phytomedicine, 9 (5): 405-9. [PMID:12222659]
12. Xu S, Zhong A, Bu X, Ma H, Li W, Xu X, Zhang J. (2015)
Salvianolic acid B inhibits platelets-mediated inflammatory response in vascular endothelial cells.
Thromb Res, 135 (1): 137-45. [PMID:25466843]
13. 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]
14. Ying HZ, Chen Q, Zhang WY, Zhang HH, Ma Y, Zhang SZ, Fang J, Yu CH. (2017)
PDGF signaling pathway in hepatic fibrosis pathogenesis and therapeutics (Review).
Mol Med Rep, 16 (6): 7879-7889. [PMID:28983598]
15. Zhang CY, Yuan WG, He P, Lei JH, Wang CX. (2016)
Liver fibrosis and hepatic stellate cells: Etiology, pathological hallmarks and therapeutic targets.
World J Gastroenterol, 22 (48): 10512-10522. [PMID:28082803]
16. Zhang Z, Ji J, Zhang D, Ma M, Sun L. (2020)
Protective effects and potential mechanism of salvianolic acid B on sodium laurate-induced thromboangiitis obliterans in rats.
Phytomedicine, 66: 153110. [PMID:31790900]
17. 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]