An ERAD inhibitor
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Eeyarestatin 1

Item No. 10012609

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(4-chlorophenyl)-4-[[[(4-chlorophenyl)amino]carbonyl] hydroxyamino]-5,5-dimethyl-2-oxo-1- imidazolidineacetic acid 2-[3-(5-nitro-2-furanyl)-2-propen-1-ylidene]hydrazide
CAS Number
412960-54-4
Molecular Formula
C27H25Cl2N7O7
Formula Weight
630.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/ml
λmax
245, 285, 380 nm
SMILES
O=C1N(CC(N/N=C/C=C/C2=CC=C([N+]([O-])=O)O2)=O)C(C)(C)C(N(C(NC3=CC=C(Cl)C=C3)=O)O)N1C4=CC=C(Cl)C=C4
InChi Code
InChI=1S/C27H25Cl2N7O7/c1-27(2)24(35(40)25(38)31-19-9-5-17(28)6-10-19)34(20-11-7-18(29)8-12-20)26(39)33(27)16-22(37)32-30-15-3-4-21-13-14-23(43-21)36(41)42/h3-15,24,40H,16H2,1-2H3,(H,31,38)(H,32,37)/b4-3+,30-15+
InChi Key
JTUXTPWYZXWOIB-LWWHHIEBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $62

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    10 mg

    $116

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    25 mg

    $222

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    Product Description

    Terminally misfolded proteins, recognized by chaperones on the endoplasmic reticulum (ER), are transported to depots for ubiquitination and proteasomal degradation by the ER-associated protein degradation (ERAD) pathway. Eeyarestatin 1 is an inhibitor of the ERAD pathway, blocking the degradation of misfolded proteins at a dose of 8 µM.1 It associates with the p97-associated deubiquitinating complex in cells, preventing deubiquitination of substrates by ataxin-3.2,3 Eeyarestatin 1, at 4 µM, interferes with both retrograde and anterograde trafficking of proteins, including certain toxins, and potentially, viruses.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiebiger, E., Hirsch, C., Vyas, J.M., et al. Dissection of the dislocation pathway for type I membrane proteins with a new small molecule inhibitor, eeyarestatin. Mol. Biol. Cell 15(4), 1635-1646 (2004).

    2. Wang, Q., Li, L., and Ye, Y. Inhibition of p97-dependent protein degradation by Eeyarestatin I. The Journal of Biological Chemisty 283(12), 7445-7454 (2008).

    3. Wang, Q., Shinkre, B.A., Lee, J.G., et al. The ERAD inhibitor Eeyarestatin I is a bifunctional compound with a membrane-binding domain and a p97/VCP inhibitory group. PLoS One 5(11), 1-12 (2010).

    4. Aletrari, M.O., McKibbin, C., Williams, H., et al. Eeyarestatin 1 interferes with both retrograde and anterograde intracellular trafficking pathways. PLoS One 6(7), 1-11 (2011).