Structure Database (LMSD)
Common Name
Juglanin
Systematic Name
Synonyms
3D model of Juglanin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Juglanin is a flavonol that has been found in J. mandshurica and has diverse biological activities.1,2,3 It reduces the levels of reactive oxygen species (ROS) increased by oscillatory shear stress (OSS) in human aortic endothelial cells (HAECs) when used at concentrations of 2.5 and 5 µM.1 It also reduces OSS-induced increases in VCAM-1 and E-selectin protein levels in HAECs and decreases the attachment of THP-1 monocytes to HAECs. Juglanin (2.5, 5, and 10 µM) inhibits the proliferation of MCF-7 human breast cancer cells, as well as induces JNK activation, autophagosome formation, apoptosis, and cell cycle arrest at the G2/M phase in the same cells.2 It reduces tumor growth in an MCF-7 mouse xenograft model when administered at doses of 10 and 20 mg/kg. Juglanin (15 and 30 mg/kg) reduces body weight, renal fibrosis, and blood glucose levels, as well as serum and renal levels of Tnf-α, Il-1β, Il-6, and chemokine (C-C motif) ligand 2 (Ccl2), and improves glucose tolerance in a mouse model of high-fat diet- and obesity-induced kidney disease.3
This information has been provided by Cayman Chemical
References
1. Zhao, J., Quan, X., Xie, Z., et al. Juglanin suppresses oscillatory shear stress-induced endothelial dysfunction: An implication in atherosclerosis. Int. Immunopharmacol. 89(Pt B), 107048 (2020).
2. Sun, Z.-L., Dong, J.-L., and Wu, J. Juglanin induces apoptosis and autophagy in human breast cancer progression via ROS/JNK promotion. Biomed. Pharmacother. 85, 303-312 (2017).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
POQICXMTUPVZMX-UXYNSRGZSA-N
InChi (Click to copy)
InChI=1S/C20H18O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-1-3-9(22)4-2-8/h1-6,13,15,17,20-25,27H,7H2/t13-,15-,17+,20-/m0/s1
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC(O)=CC=3)=C(O[C@@H]3O[C@@H](CO)[C@H](O)[C@H]3O)C(=O)C=2C(O)=C1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
30
Rings
4
Aromatic Rings
3
Rotatable Bonds
4
Van der Waals Molecular Volume
339.20
Topological Polar Surface Area
172.12
Hydrogen Bond Donors
6
Hydrogen Bond Acceptors
10
logP
2.72
Molar Refractivity
103.95
Admin
Created at
-
Updated at
-