Structure Database (LMSD)

Common Name
Apigenin 5,7,4'-trimethyl ether
Systematic Name
Synonyms
LM ID
LMPK12111071
Formula
Exact Mass
Calculate m/z
312.099775
Status
Curated


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

HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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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