Structure Database (LMSD)
Common Name
Demethylnobiletin
Systematic Name
5-Hydroxy-6,7,8,3',4'-pentamethoxyflavone
Synonyms
3D model of Demethylnobiletin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
5-O-Demethylnobiletin is a flavonoid that has been found in S. tragoriganum and has diverse biological activities.1,2,3,4 It induces neurite outgrowth and the expression of the genes encoding the neuronal differentiation and synapse formation markers growth-associated protein 43 (GAP43) and synaptophysin in PC12 cells when used at concentrations ranging from 10 to 20 µM.1 5-O-Demethylnobiletin (2.5-20 µM) reduces triglyceride levels in 3T3-L1 preadipocytes and decreases body weight, intra-abdominal fat, plasma and liver triglyceride levels, and plasma cholesterol levels in a mouse model of high-fat diet-induced obesity when administered at a dose of 25 mg/kg.2 It reduces hepatic fibrosis and malondialdehyde (MDA) levels in a mouse model of carbon tetrachloride-induced liver injury.3 5-O-Demethylnobiletin also reduces ear edema, inflammatory cell infiltration, and papillar fibrosis in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate (TPA).4
This information has been provided by Cayman Chemical
References
3. Chang, S.N., Kim, S.H., Dey, D.K., et al. 5-O-Demethylnobiletin alleviates CCL4-induced acute liver injury by equilibrating ROS-mediated apoptosis and autophagy induction. Int. J. Mol. Sci. 22(3), 1083 (2021).
4. Bas, E., Recio, M.C., Giner, R.M., et al. Anti-inflammatory activity of 5-O-demethylnobiletin, a polymethoxyflavone isolated from Sideritis tragoriganum. Planta Med. 72(2), 136-142 (2006).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
DOFJNFPSMUCECH-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C20H20O8/c1-23-12-7-6-10(8-14(12)24-2)13-9-11(21)15-16(22)18(25-3)20(27-5)19(26-4)17(15)28-13/h6-9,22H,1-5H3
SMILES (Click to copy)
C1(OC)=C(OC)C2OC(C3C=C(OC)C(OC)=CC=3)=CC(=O)C=2C(O)=C1OC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
3
Aromatic Rings
3
Rotatable Bonds
6
Van der Waals Molecular Volume
333.98
Topological Polar Surface Area
96.59
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
8
logP
4.11
Molar Refractivity
102.45
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