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Embelin (Standard)

CAT: 0804-HY-17473R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17473R-01Size:5 mg
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Description
Embelin (Standard) is the analytical standard of Embelin. This product is intended for research and analytical applications. Embelin (Embelic acid), a potent, nonpeptidic XIAP inhibitor (IC50=4.1 μM), inhibits cell growth, induces apoptosis, and activates caspase-9 in prostate cancer cells with high levels of XIAP. Embelin blocks NF-kappaB signaling pathway leading to suppression of NF-kappaB-regulated antiapoptotic and metastatic gene products. Embelin also induces autophagic and apoptotic cell death in human oral squamous cell carcinoma cells[1][2][3].
CAS Number
550-24-3
Product Name Alternative
Embelic acid (Standard) ; Emberine (Standard) ; NSC 91874 (Standard)
UNSPSC
12352211
Target
Apoptosis; Autophagy; IAP; NF-κB; Reference Standards
Type
Reference Standards
Related Pathways
Apoptosis; Autophagy; NF-κB; Others
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/embelin-standard.html
Smiles
O=C1C(O)=C(CCCCCCCCCCC)C(C(O)=C1)=O
Molecular Formula
C17H26O4
Molecular Weight
294.39
References & Citations
[1]Nikolovska-Coleska Z, et al. Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database. J Med Chem. 2004;47 (10) :2430-2440.|[2]Ahn KS, et al. Embelin, an inhibitor of X chromosome-linked inhibitor-of-apoptosis protein, blocks nuclear factor-kappaB (NF-kappaB) signaling pathway leading to suppression of NF-kappaB-regulated antiapoptotic and metastatic gene products. Mol Pharmacol. 2007;71 (1) :209-219.|[3]Lee YJ, et al. XIAP inhibitor embelin induces autophagic and apoptotic cell death in human oral squamous cell carcinoma cells. Environ Toxicol. 2017;32 (11) :2371-2378.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Embelin

Embelin is a member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, antineoplastic and inhibitory activity towards hepatitis C protease. It has a role as an antimicrobial agent, an antineoplastic agent, a hepatitis C protease inhibitor and a plant metabolite.

CAS Number550-24-3
PubChem CID3218
IUPAC Name2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Molecular FormulaC17H26O4
Molecular Weight294.4
XLogP5.4
Topological Polar Surface Area74.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count10
Heavy Atom Count21
Formal Charge0
Complexity432
SMILES
CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
InChI
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
InChIKey
IRSFLDGTOHBADP-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Embelin
CAS: 550-24-3
CID: 3218
Formula: C17H26O4
MW: 294.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight294.4
XLogP35.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count10
Exact Mass294.18310931
Monoisotopic Mass294.18310931
Topological Polar Surface Area74.6 Ų
Heavy Atom Count21
Formal Charge0
Complexity432
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
A8235-5.1Embelin

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