Structure Database (LMSD)

Common Name
Oroxylin A
Systematic Name
Synonyms
LM ID
LMPK12111096
Formula
Exact Mass
Calculate m/z
284.068475
Status
Curated



Classification

Biological Context

Oroxylin A is a flavonoid that has been found in S. radix and has diverse biological activities.1,2,3 It inhibits decreases in cell viability and increases in nitric oxide (NO) production induced by polyinosinic-polycytidylic acid (poly(I:C)) in RAW 264.7 macrophages when used at concentrations ranging from 5 to 25 μM.2 Oroxylin A (10-50 μM) also inhibits poly(I:C)-induced increases in IL-1α, IL-1β, GM-CSF, IL-6, IL-10, monocyte chemoattractant protein-1 (MCP-1), and TNF-α production in RAW 264.7 cells. Oroxylin A (10 and 20 μM) inhibits hypoxia-induced migration and invasion of MCF-7, DU145, and HepG2 cells in wound healing and cell invasion assays, respectively.3 It is an inhibitor of the UDP-glucuronosyltransferase (UGT) isoform UGT1A1 (IC50 = 9.14 μM) and P-glycoprotein (IC50 = 78.3 μM).4,5 Oroxylin A increases the cytotoxicity of the P-glycoprotein substrate paraquat in MDR1-MDCKII cells and paclitaxel in MX-1 and MX-1/T cells.5

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
LKOJGSWUMISDOF-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-8,18-19H,1H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC=CC=3)=CC(=O)C=2C(O)=C1OC

Other Databases

Wikipedia
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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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