Structure Database (LMSD)

Common Name
Eupatorin
Systematic Name
3',5-Dihydroxy-4',6,7-trimethoxyflavone
Synonyms
LM ID
LMPK12111239
Formula
C18H16O7
Exact Mass
Calculate m/z
344.089605
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

Eupatorin is a flavonoid that has been found in L. camara and has diverse biological activities.1,2,3,4 It inhibits the growth of HeLa, MK-1, and B16/F10 tumor cells (GI50s = 15, 58, and 44 µM, respectively).1 Eupatorin is active against T. cruzi epimastigotes and trypomastigotes (IC50s = 0.2 and 61.8 µg/ml, respectively) without inducing cytotoxicity in Vero cells (IC50 = >500 µg/ml).2 It induces vasorelaxation in isolated rat thoracic aortic rings precontracted with phenylephrine (pD2 = 6.66).3 Eupatorin (10 and 100 µM) reduces nuclear translocation of NF-κB and STAT1α in J774 murine macrophages and reduces paw edema in a mouse model of carrageenan-induced paw inflammation when administered at a dose of 50 mg/kg.4

This information has been provided by Cayman Chemical

References

1. Nagao, T., Abe, F., Kinjo, J., et al. Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. Biol. Pharm. Bull. 25(7), 875-879 (2002).
2. Beer, M.F., Frank, F.M., Germán Elso, O., et al. Trypanocidal and leishmanicidal activities of flavonoids isolated from Stevia satureiifolia var. satureiifolia. Pharm. Biol. 54(10), 2188-2195 (2016).
3. Yam, M.F., Tan, C.S., Ahmad, M., et al. Mechanism of vasorelaxation induced by eupatorin in the rats aortic ring. Eur. J. Pharmacol. 789, 27-36 (2016).
4. Laavola, M., Nieminen, R., Yam, M.F., et al. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 78(8), 779-786 (2012).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
KLAOKWJLUQKWIF-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=C(O)C(OC)=CC=3)=CC(=O)C=2C(O)=C1OC

Other Databases

CHEBI ID
136666
METABOLOMICS ID
FL3FECNS0013
PubChem CID
97214
Cayman ID
29599

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 3
Aromatic Rings 3
Rotatable Bonds 4
Van der Waals Molecular Volume 290.59
Topological Polar Surface Area 98.36
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 3.80
Molar Refractivity 91.01

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Updated at
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