Structure Database (LMSD)
Common Name
Embelin
Systematic Name
2,5-dihydroxy-3-undecyl-1,4-benzoquinone
Synonyms
3D model of Embelin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Embelin is a benzoquinone that has been found in E. ribes and has diverse biological activities.1 It inhibits viral replication of the influenza A subtype H1N1 and the influenza B subtype Victoria-like in MDCK cells (IC50s = 0.3 and 0.2 µM, respectively).2 It is also an inhibitor of X-linked inhibitor of apoptosis (XIAP; IC50 = 4.1 µM in a fluorescence polarization assay).3 Embelin (20-50 µM) induces apoptosis and increases caspase-9 levels in PC3 prostate cancer cells. It completely inhibits TNF-α-induced NF-κB and IκB kinase (IKK) activation and inhibits TNF-α-induced IκBα phosphorylation in KBM5 human myeloid cells when used at a concentration of 50 µM.1 It is active against the Gram-positive bacteria B. subtilis, S. aureus, and M. luteus (MICs = 20, 20, and 25 µg/ml, respectively) and the Gram-negative bacteria P. aeruginosa, K. pneumoniae, and E. coli (MICs = 25, 25, and 45 µg/ml, respectively).4
This information has been provided by Cayman Chemical
References
1. Ahn, K.S., Sethi, G., and Aggarwal, B.B. Embelin, an inhibitor of X chromosome-linked inhibitor-of-apoptosis protein, blocks nuclear factor-κB (NF-κB) signaling pathway leading to suppression of NF-κB-regulated antiapoptotic and metastatic gene products. Mol. Pharmacol. 71(1), 209-219 (2007).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Embelia schimperi
(#2595069)
Magnoliopsida
(#3398)
Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.,
Phytother Res, 2000
Phytother Res, 2000
Pubmed ID:
11054840
String Representations
InChiKey (Click to copy)
IRSFLDGTOHBADP-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
SMILES (Click to copy)
C1(O)C(=O)C(CCCCCCCCCCC)=C(O)C(=O)C=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
1
Aromatic Rings
0
Rotatable Bonds
10
Van der Waals Molecular Volume
314.90
Topological Polar Surface Area
74.60
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
4.31
Molar Refractivity
82.22
Admin
Created at
6th Jan 2021
Updated at
6th Jan 2021