Structure Database (LMSD)

Common Name
3,5,6,7,8,3',4'-Heptamethoxyflavone
Systematic Name
2-(3,4-Dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-4H-1-benzopyran-4-one
Synonyms
LM ID
LMPK12113345
Formula
Exact Mass
Calculate m/z
432.142035
Status
Curated

Classification

Biological Context

3,5,6,7,8,3',4'-Heptamethoxyflavone (HMF) is a polymethoxyflavone that has been found in C. reticulata and has diverse biological activities.1,2,3,4 It inhibits the efflux of Hoechst 33342 by breast cancer resistance protein (BCRP) and rhodamine 123 by P-glycoprotein (P-gp), also known as multidrug resistance protein 1 (MDR1), in MDCK cells expressing the human transporters (IC50s = 1.4 and 31 µM, respectively).1 HMF (50, 100, and 200 µg/ml) prevents UVB-induced decreases in type I procollagen in primary human dermal fibroblast neonatal (HDFn) cells.2 It inhibits the proliferation of B16 melanoma 4A5, CCRF-HSB-2 leukemia, and TGBC11TKB gastric cancer cells (IC50s = 38, 29, and 9 µM, respectively).3 HMF (50 mg/kg) prevents corticosterone-induced increases in immobility time in the forced swim test in mice.4

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/
Citrus sinensis (#2711)
Magnoliopsida (#3398)
Orange Peel Constituents, Flavones of Neutral Fraction of Benzene Extractables of Orange Peel Juice,
J Agric Food Chem, 1965

String Representations

InChiKey (Click to copy)
SSXJHQZOHUYEGD-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H24O9/c1-24-12-9-8-11(10-13(12)25-2)16-19(27-4)15(23)14-17(26-3)20(28-5)22(30-7)21(29-6)18(14)31-16/h8-10H,1-7H3
SMILES (Click to copy)
C1(OC)=C(OC)C2OC(C3C=C(OC)C(OC)=CC=3)=C(OC)C(=O)C=2C(OC)=C1OC

Other Databases

HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 3
Rotatable Bonds 8
Van der Waals Molecular Volume 377.37
Topological Polar Surface Area 94.82
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 9
logP 4.42
Molar Refractivity 113.89

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Created at
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Updated at
18th Sep 2025