Structure Database (LMSD)

Common Name
Wogonin
Systematic Name
5,7-Dihydroxy-8-methoxyflavone
Synonyms
LM ID
LMPK12111330
Formula
C16H12O5
Exact Mass
Calculate m/z
284.068475
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavones and Flavonols [PK1211]

Biological Context

Wogonin is an O-methylated flavonoid isolated from the root of the traditional Chinese herb S. baicalensis with anti-inflammatory, antioxidant, and neuroprotective activities.1 At concentrations of 5-50 μM, wogonin inhibits inflammatory activation of cultured brain microglia by diminishing LPS-induced TNF-α, IL-1β, and nitric oxide production.2 Wogonin at 75 μM demonstrates tumor therapeutic potential inducing sub-G1 phase apoptosis through activation of caspase-3 activity in human osteocarcinoma cell lines.3

This information has been provided by Cayman Chemical

References

1. Lee, H., Kim, Y.O., Kim, H., et al. Flavonoid wogonin from medicinal herb is neuroprotective by inhibiting inflammatory activation of microglia. FASEB J. 17(13), 1943-1944 (2003).
2. Huang, W.H., Chien, P.Y., Yang, C.H., et al. Novel synthesis of flavonoids of Scutellaria baicalensis GEORGI. Chem. Pharm. Bull. (Tokyo) 51(3), 339-340 (2003).
3. Lin, C.C., Kuo, C.L., Lee, M.H., et al. Wogonin triggers apoptosis in human osteosarcoma U-2 OS cells through the endoplasmic reticulum stress, mitochondrial dysfunction and caspase-3-dependent signaling pathways. Int. J. Oncol. 39(1), 217-224 (2011).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
XLTFNNCXVBYBSX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3
SMILES (Click to copy)
C1(O)=C(OC)C2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1

Other Databases

Wikipedia
Wogonin
KEGG ID
C10197
CHEBI ID
10043
METABOLOMICS ID
FL3FF9NS0002
PubChem CID
5281703
Cayman ID
14248

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 3
Aromatic Rings 3
Rotatable Bonds 2
Van der Waals Molecular Volume 238.41
Topological Polar Surface Area 79.90
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 3.78
Molar Refractivity 77.91

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Updated at
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