Structure Database (LMSD)

Common Name
Gossypetin
Systematic Name
Synonyms
LM ID
LMPK12113231
Formula
C15H10O8
Exact Mass
Calculate m/z
318.03757
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

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

Biological Context

Gossypetin is a flavonoid that has been found in H. sabdariffa and has diverse biological activities.1,2,3 It inhibits the MAP2K kinases MKK3 and MKK6 in a concentration-dependent manner, as well as induces apoptosis and cell cycle arrest at the G2 phase in KYSE-450 and KYSE-510 esophageal cancer cells when used at a concentration of 20 µM.1 Gossypetin scavenges DPPH radicals and inhibits copper-induced lipid peroxidation in cell-free assays.2 It reduces high-fat diet-induced increases in serum cholesterol, triglycerides, and LDL-cholesterol levels, as well as decreases aortic extracellular lipid and foam cell deposits in a rabbit model of atherosclerosis when administered at a dose of 10 mg/kg.3

This information has been provided by Cayman Chemical

References

1. Xie, X., Liu, K., Liu, F., et al. Gossypetin is a novel MKK3 and MKK6 inhibitor that suppresses esophageal cancer growth in vitro and in vivo. Cancer Lett. 442, 126-136 (2019).
2. Chen, J.-H., Tsai, C.-W., Wang, C.-P., et al. Anti-atherosclerotic potential of gossypetin via inhibiting LDL oxidation and foam cell formation. Toxicol. Appl. Pharmacol. 272(2), 313-324 (2013).
3. Lin, H.-H. In vitro and in vivo atheroprotective effects of gossypetin against endothelial cell injury by induction of autophagy. Chem. Res. Toxicol. 28(2), 202-215 (2015).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
YRRAGUMVDQQZIY-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H
SMILES (Click to copy)
C1(O)=C(O)C2OC(C3C=C(O)C(O)=CC=3)=C(O)C(=O)C=2C(O)=C1

Other Databases

Wikipedia
Gossypetin
KEGG ID
C04109
CHEBI ID
16400
METABOLOMICS ID
FL5FFCNS0001
PubChem CID
5280647
Cayman ID
33840

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 3
Aromatic Rings 3
Rotatable Bonds 1
Van der Waals Molecular Volume 247.48
Topological Polar Surface Area 151.59
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 8
logP 2.59
Molar Refractivity 78.02

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Updated at
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