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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2D Structure
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Physico-chemical Properties
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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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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/)

Bioactivity Comments
Experimental evidence suggests that SalB's anti-liver fibrosis action is mediated by regulation of the PDGF/PDGFRβ signalling pathway and inhibition of hepatic stellate cell activation (determined as inhibtion of α-SMA and collagen I expression) [7]. In addition, SalB inhibits aggregation and activation of platelets in in vitro and in vivo models [10-12].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
lysine demethylase 1A Hs Inhibitor Inhibition 7.0 pIC50 - 5
pIC50 7.0 (IC50 1.1x10-7 M) [5]
Selectivity at catalytic receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
platelet derived growth factor receptor beta Hs Inhibitor Binding 5.2 pKd - 7
pKd 5.2 (Kd 6.15x10-6 M) [7]
Description: Binding affinity determined by surface plasmon resonance analysis
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CD226 molecule Mm Inhibitor Inhibition - - -

Description: SalB-CD226 interaction demonstrated by flow cytometry analysis using Cy5-labeled SalB and CD226 expressed in HEK293T cells.