Structure Database (LMSD)
Common Name
Nobiletin
Systematic Name
Synonyms
3D model of Nobiletin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Nobiletin is a polymethoxylated flavonoid that has been found in C. unshiu and has diverse biological activities.1,2,3 It reduces LPS- and IFN-γ-induced increases in inducible nitric oxide synthase (iNOS) protein levels and NO production in RAW 264.7 cells when used at concentrations of 25, 50, and 100 µM.1 Nobiletin decreases proliferation of A549 lung, B16/4A5 melanoma, CCRF-HSB-2 leukemia, and TGBC11TKB gastric cancer cell lines with IC50 values of 22, 18, 13, and 8.3 µM, respectively.2 Dietary administration of nobiletin (0.3% w/w) reduces body weight, hepatic steatosis, and plasma LDL and HDL cholesterol levels in mice fed a high-fat, high-cholesterol diet for 18 weeks.3 It also inhibits increases in plasma glucose levels in an intraperitoneal glucose tolerance test in the same model.
This information has been provided by Cayman Chemical
References
1. Murakami, A., Nakamura, Y., Torikai, K., et al. Inhibitory effect of citrus nobiletin on phorbol ester-induced skin inflammation, oxidative stress, and tumor promotion in mice. Cancer Res. 60(18), 5059-5066 (2000).
3. Morrow, N.M., Burke, A.C., Samsoondar, J.P., et al. The citrus flavonoid nobiletin confers protection frommetabolic dysregulation in high-fat-fed mice independent of AMPK. J. Lipid Res. 61(3), 387-402 (2020).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
MRIAQLRQZPPODS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C21H22O8/c1-23-13-8-7-11(9-15(13)24-2)14-10-12(22)16-17(25-3)19(26-4)21(28-6)20(27-5)18(16)29-14/h7-10H,1-6H3
SMILES (Click to copy)
C1(OC)=C(OC)C2OC(C3C=CC(OC)=C(OC)C=3)=CC(=O)C=2C(OC)=C1OC
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
3
Aromatic Rings
3
Rotatable Bonds
7
Van der Waals Molecular Volume
351.28
Topological Polar Surface Area
85.59
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
8
logP
4.41
Molar Refractivity
107.34
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Updated at
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