Structure Database (LMSD)

Common Name
Baicalein
Systematic Name
5,6,7-Trihydroxyflavone
Synonyms
  • Noroxylin
LM ID
LMPK12111095
Formula
Exact Mass
Calculate m/z
270.052825
Status
Curated



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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