Structure Database (LMSD)

Common Name
Juglanin
Systematic Name
Synonyms
LM ID
LMPK12111839
Formula
Exact Mass
Calculate m/z
418.09
Status
Curated

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

CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID

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

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Updated at
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