Structure Database (LMSD)
Common Name
Eupatorin
Systematic Name
3',5-Dihydroxy-4',6,7-trimethoxyflavone
Synonyms
3D model of Eupatorin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
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
METABOLOMICS ID
PubChem CID
Cayman ID
NP-MRD ID(NMR)
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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