Structure Database (LMSD)

Common Name
Chrysosplenetin
Systematic Name
5,4'-Dihydroxy-3,6,7,3'-tetramethoxyflavone
Synonyms
  • Quercetagetin 3,6,7,3'-tetramethyl ether
LM ID
LMPK12113009
Formula
C19H18O8
Exact Mass
Calculate m/z
374.10017
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

Chrysosplenetin is a flavonoid that has been found in A. annua and has diverse biological activities.1,2,3 It is active against P. falciparum in vitro (IC50 = 23 µM).1 Chrysosplenetin inhibits the cytopathic effect of enterovirus 71 (EV71) in Vero cells (EC50 = 0.68 µM) and increases survival in a neonatal mouse model of EV71 infection when administered at doses of 1 and 5 mg/kg.2 It also increases proliferation and osteogenic differentiation of isolated human bone marrow stromal cells (BMSCs) and prevents estrogen deficiency-induced bone loss in ovariectomized mice.3

This information has been provided by Cayman Chemical

References

1. Liu, K.C., Yang, S.L., Roberts, M.F., et al. Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures. Plant Cell Rep. 11(12), 637-640 (1992).
2. Dai, W., Bi, J., Li, F., et al. Antiviral efficacy of flavonoids against enterovirus 71 infection in vitro and in newborn mice. Viruses 11(7), 625 (2019).
3. Hong, G., He, X., Shen, Y., et al. Chrysosplenetin promotes osteoblastogenesis of bone marrow stromal cells via Wnt/β-catenin pathway and enhances osteogenesis in estrogen deficiency-induced bone loss. Stem Cell Res. Ther. 10(1), 277 (2019).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
NBVTYGIYKCPHQN-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C19H18O8/c1-23-11-7-9(5-6-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=C(OC)C(O)=CC=3)=C(OC)C(=O)C=2C(O)=C1OC

Other Databases

Wikipedia
Chrysosplenetin
KEGG ID
C10030
CHEBI ID
3689
METABOLOMICS ID
FL5FECNS0028
PubChem CID
5281608
Cayman ID
30625

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 3
Aromatic Rings 3
Rotatable Bonds 5
Van der Waals Molecular Volume 316.68
Topological Polar Surface Area 107.59
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 8
logP 3.81
Molar Refractivity 97.57

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Updated at
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