Structure Database (LMSD)

Common Name
Fisetin
Systematic Name
3,3',4',7-Tetrahydroxyflavone
Synonyms
LM ID
LMPK12111566
Formula
C15H10O6
Exact Mass
Calculate m/z
286.04774
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

Fisetin is a flavonoid that has been found in various fruits and vegetables and has diverse biological activities.1,2,3,4 It scavenges radicals in a Trolox equivalent antioxidant capacity (TEAC) assay and inhibits oxidative burst induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) in isolated human polymorphonuclear neutrophils (PMNs) when used at a concentration of 10 µM.1,3 Fisetin (10-60 µM) induces cell cycle arrest at the G1 phase and apoptosis in, as well as inhibits the proliferation of, LNCaP prostate cancer cells.2 It inhibits LPS-induced production of nitrite, prostaglandin E2 (PGE2), and NF-κB activation in RAW 264.7 cells.3 Fisetin (1 mg/animal) reduces tumor growth in a CWR22Rυ1 prostate cancer mouse xenograft model.4

This information has been provided by Cayman Chemical

References

1. Khan, N., Asim, M., Afaq, F., et al. A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice. Cancer Res. 68(20), 8555-8563 (2008).
2. Wang, L., Tu, Y.-C., Lian, T.-W., et al. Distinctive antioxidant and antiinflammatory effects of flavonols. J. Agric. Food Chem. 54(26), 9798-9804 (2006).
3. Khan, N., Afaq, F., Syed, D.N., et al. Fisetin, a novel dietary flavonoid, causes apoptosis and cell cycle arrest in human prostate cancer LNCaP cells. Carcinogenesis 29(5), 1049-1056 (2008).
4. Khan, N., Syed, D.N., Ahmad, N., et al. Fisetin: A dietary antioxidant for health promotion. Antioxid. Redox Signal. 19(2), 151-162 (2013).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
XHEFDIBZLJXQHF-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
SMILES (Click to copy)
C1(O)=CC2OC(C3C=C(O)C(O)=CC=3)=C(O)C(=O)C=2C=C1

Other Databases

Wikipedia
Fisetin
KEGG ID
C10041
CHEBI ID
42567
METABOLOMICS ID
FL5F1CNS0001
PubChem CID
5281614
Cayman ID
15246
PDB ID
FSE
GuidePharm ID
5182

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 229.90
Topological Polar Surface Area 111.13
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 3.18
Molar Refractivity 74.69

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Updated at
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