Structure Database (LMSD)

Common Name
Demethylnobiletin
Systematic Name
5-Hydroxy-6,7,8,3',4'-pentamethoxyflavone
Synonyms
LM ID
LMPK12111479
Formula
Exact Mass
Calculate m/z
388.11582
Status
Curated


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

HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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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Updated at
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