Amentoflavone

Category	Respiratory syncytial Virus (RSV)
CAS	1617-53-4
Description	Amentoflavone, a natural flavonoid isolated from the the seed of Ginkgo biloba L, exhibits anti-inflammatory activity, and inhibits NF-κB/DNA binding activity potently along with inhibition of degradation of IκBα and NF-κB translocation into nucleus in TNFα-activated A549 cells. Amentoflavone has the inhibition of LPS-induced NO formation, due to its inhibition of NF-kappaB by blocking degradation, which may be the mechanistic basis of the anti-inflammatory effects of amentoflavone.

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Product Information

Synonyms	4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 3''',8-Biflavone, 4',4''',5,5'',7,7''-hexahydroxy-; 8-[5-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Ginkgetin, didemethyl-; Amenthoflavone; I3',II8-Biapigenin; NSC 295677; Tridemethylsciadopitysin
IUPAC Name	8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Molecular Weight	538.46
Molecular Formula	C30H18O10
Canonical SMILES	C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
InChI	InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
InChIKey	YUSWMAULDXZHPY-UHFFFAOYSA-N
Boiling Point	910.5±65.0°C at 760 mmHg
Melting Point	245-250°C (dec.)
Flash Point	308.5±27.8 °C
Purity	>98%
Density	1.656±0.06 g/cm3
Solubility	Soluble in DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)
Appearance	Pale Yellow to Yellow Solid
Application	Cytochrome P-450 CYP2C9 Inhibitors
Shelf Life	2 years
Storage	Store in a cool and dry place and at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Complexity	1050
Exact Mass	538.090027
Index Of Refraction	1.793
In Vitro	Amentoflavone (1-60 µM) inhibits the production of nitric oxide in a concentration-dependent manner in RAW 264.7 cells Amentoflavone (50-200 µM) inhibits the viability of U-87 MG cells with IC50 value of 100 µM at 48 h Amentoflavone (0, 50, 100 µM; 48 h) induces Apoptosis and cell cycle arrest at sub-G1 phase Amentoflavone (0, 50, 100 µM; 48 h) inhibits NF-ĸB activation and decreases the expression of MCL1 and C-FLIP protein in 87 MG cells Amentoflavone (0-32 µg/ml) shows antibacterial activity with MICs of 8, 4, 32, 8, 16, 8 µg/ml for E. faecium ATCC 19434, Saureus ATCC 25923, S. mutans ATCC 3065, E. coli O-157 ATCC 25922, E. coli ATCC 43895, P. aeruginosa ATCC 27853, respectively.
In Vivo	Amentoflavone (1-60 µM) inhibits the production of nitric oxide in a concentration-dependent manner in RAW 264.7 cells.
PSA	181.80000
Target	Reactive Oxygen Species; Apoptosis; Bacterial; Fungal; RSV; GABA Receptor
Vapor Pressure	0.0±0.3 mmHg at 25°C
XLogP3-AA	5