Structure Database (LMSD)
Common Name
Baicalein
Systematic Name
5,6,7-Trihydroxyflavone
Synonyms
- Noroxylin
3D model of Baicalein
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Baicalein is a flavonoid originally isolated from the roots of S. baicalensis that has diverse biological activities.1 It inhibits human platelet 12-lipoxygenase (12-LO) and human reticulocyte 15-LO-1 (IC50s = 0.64 and 1.6 µM, respectively) but is less potent at 15-LO-1 when the detergent Triton-X is present (IC50 = 38 µM).2 Baicalein inhibits lipid peroxidation, as assessed by production of thiobarbituric acid (TBARS; IC50 = 5 µM), and inhibits growth of Huh-7, KIM-1, and HLF human hepatocellular carcinoma cells (IC50s = 17-70 µg/ml).3,4 Baicalein increases intracellular calcium levels by increasing release from the endoplasmic reticulum and via PKC-dependent calcium channels in the plasma membrane, leading to increases in reactive oxygen species (ROS), caspase-9 and -3 activation, and apoptosis in ZR-75-1 human breast cancer cells.5 Baicalein increases levels of peroxisome proliferator-activated receptor β/δ (PPARβ/δ) in BV-2 microglia and primary microglia and decreases the level of 12- and 15-LO products.6 It also decreases symptoms of experimental autoimmune encephalomyelitis (EAE) in a mouse model of multiple sclerosis, when administered at a dose of 75 mg/kg per day.
This information has been provided by Cayman Chemical
References
2. Matsuzaki, Y., Korokawa, N., Terai, S., et al. Cell death induced by baicalein in human hepatocellular carcinoma cell lines. Jpn. J. Cancer Res. 87(2), 170-177 (1996).
3. Shibata, K., Iwata, S., and Nakamura, M. Baicalin, a new flavone-glucuronic acid compound from the roots of Scutellaria baicalensis. Acta Phytochimica 1, 105-139 (1923).
6. Xu, J., Zhang, Y., Xiao, Y., et al. Inhibition of 12/15-lipoxygenase by baicalein induces microglia PPARβ/δ: A potential therapeutic role for CNS autoimmune disease. Cell Death Dis. 4(4), e569 (2013).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
FXNFHKRTJBSTCS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
3
Aromatic Rings
3
Rotatable Bonds
1
Van der Waals Molecular Volume
221.11
Topological Polar Surface Area
90.90
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.48
Molar Refractivity
73.02
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Updated at
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