Structure Database (LMSD)
Common Name
Apigenin 5,7,4'-trimethyl ether
Systematic Name
Synonyms
3D model of Apigenin 5,7,4'-trimethyl ether
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
4’,5,7-Trimethoxyflavone is a flavonoid that has been found in K. parviflora and has diverse biological activities.1,2,3 It inhibits acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) by 47.1 and 46.2%, respectively, in a cell-free assay when used at a concentration of 0.1 mg/ml.1 4’,5,7-Trimethoxyflavone (1 and 10 µM) scavenges radicals in a Trolox equivalent antioxidant capacity (TEAC) assay.2 It inhibits RANKL-induced osteoclastic differentiation of RAW 264.7 cells when used at a concentration of 10 µM. 4’,5,7-Trimethoxyflavone stimulates chloride secretion in Calu-3 human airway epithelial cells, which endogenously express cystic fibrosis transmembrane conductance regulator (CFTR) as their major apical chloride channel.3
This information has been provided by Cayman Chemical
References
1. Thao, N.P., Luyen, B.T.T., Lee, S.H., et al. Anti-osteoporotic and antioxidant activities by rhizomes of Kaempferia parviflora Wall. ex Baker. Nat. Prod. Sci. 22(1), 13-19 (2016).
3. Fischer, H., and Illek, B. Activation of the CFTR Cl- channel by trimethoxyflavone in vitro and in vivo. Cell. Physiol. Biochem. 22(5-6), 685-692 (2008).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
ZXJJBDHPUHUUHD-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3
SMILES (Click to copy)
C1(OC)=CC2OC(C3C=CC(OC)=CC=3)=CC(=O)C=2C(OC)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
3
Aromatic Rings
3
Rotatable Bonds
4
Van der Waals Molecular Volume
273.01
Topological Polar Surface Area
57.90
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
5
logP
4.39
Molar Refractivity
87.68
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Updated at
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