Structure Database (LMSD)

Common Name
Nobiletin
Systematic Name
Synonyms
LM ID
LMPK12111468
Formula
Exact Mass
Calculate m/z
402.13147
Status
Curated


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

Admin

Created at
-
Updated at
-