scutellarin   Click here for help

GtoPdb Ligand ID: 13075

Synonyms: breviscapin | scutellarein-7-glucuronide
Compound class: Natural product
Comment: Scutellarin is a bioactive plant-derived flavinoid compound that has been isolated from plants including Scoparia dulcis (sweet broom), Sempervivum ruthenicum (houseleek), the daisy-like plant Erigeron breviscapus and Scutellaria species (skullcaps). It has been used as a traditional herbal remedy, and has more recently been investigated for actions that support anti-cancer potential [3-5]. Integrated network pharmacology predictive analysis followed by experimental validation suggests that the c-Jun N-terminal kinases (JNK) pathway is important for scutellarin's bioactivity in acute myeloid leukemia (AML) models [1].

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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 12
Hydrogen bond donors 7
Rotatable bonds 4
Topological polar surface area 203.44
Molecular weight 462.36
XLogP 0.07
No. Lipinski's rules broken 2

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=CC(=CC=C1C2=CC(=O)C3=C(C=C(C(=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O4)O)O)O)O2)O
Isomeric SMILES C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O)O
InChI InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChI Key DJSISFGPUUYILV-ZFORQUDYSA-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. Huang Z, Yang Y, Fan X, Ma W. (2022)
Network pharmacology-based investigation and experimental validation of the mechanism of scutellarin in the treatment of acute myeloid leukemia.
Front Pharmacol, 13: 952677. [PMID:36160389]
2. Li L, Zou Y, Wang L, Yang L, Li Y, Liao A, Chen Z, Yu Z, Guo J, Han S. (2023)
Nanodelivery of scutellarin induces immunogenic cell death for treating hepatocellular carcinoma.
Int J Pharm, 642: 123114. [PMID:37301243]
3. Mei X, Ouyang H, Zhang H, Jia W, Lu B, Zhang J, Ji L. (2023)
Scutellarin suppresses the metastasis of triple-negative breast cancer via targeting TNFα/TNFR2-RUNX1-triggered G-CSF expression in endothelial cells.
Biochem Pharmacol, 217: 115808. [PMID:37716622]
4. Tuli HS, Bhushan S, Kumar A, Aggarwal P, Sak K, Ramniwas S, Vashishth K, Behl T, Rana R, Haque S et al.. (2023)
Autophagy Induction by Scutellaria Flavones in Cancer: Recent Advances.
Pharmaceuticals (Basel), 16 (2). [PMID:37259445]
5. Vesaghhamedani S, Mazloumi Kiapey SS, Gowhari Shabgah A, Amiresmaili S, Jahanara A, Oveisee M, Shekarchi A, Gheibihayat SM, Jadidi-Niaragh F, Gholizadeh Navashenaq J. (2023)
From traditional medicine to modern oncology: Scutellarin, a promising natural compound in cancer treatment.
Prog Biophys Mol Biol, 180-181: 19-27. [PMID:37080435]
6. Wang F, Bao MC, Xu J, Shi LL, Niu RZ, Wang TH, Liu J. (2023)
Scutellarin inhibits the glioma cell proliferation by downregulating BIRC5 to promote cell apoptosis.
J Cell Mol Med, 27 (14): 1975-1987. [PMID:37340587]
7. Yu P, Li J, Luo Y, Sun J, Hu Y, Lin B, Meng X, Xiang L. (2023)
Mechanistic Role of Scutellaria baicalensis Georgi in Breast Cancer Therapy.
Am J Chin Med, 51 (2): 279-308. [PMID:36655686]
8. Zhang J, Li X, Huang L. (2020)
Anticancer activities of phytoconstituents and their liposomal targeting strategies against tumor cells and the microenvironment.
Adv Drug Deliv Rev, 154-155: 245-273. [PMID:32473991]