Eeyarestatin I

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 525595

CAS#: 412960-54-4

Description: Eeyarestatin I is an ERAD inhibitor, preferentially inhibiting membrane-bound p97 to disrupt ER homeostasis and to induce tumor cell death.

Chemical Structure

Eeyarestatin I
CAS# 412960-54-4

Theoretical Analysis

MedKoo Cat#: 525595
Name: Eeyarestatin I
CAS#: 412960-54-4
Chemical Formula: C21H23ClN6O6
Exact Mass: 490.1368
Molecular Weight: 490.901
Elemental Analysis: C, 51.38; H, 4.72; Cl, 7.22; N, 17.12; O, 19.55

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 2 Weeks
10.0mg USD 450.0 2 Weeks
25.0mg USD 750.0 2 Weeks
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Synonym: Eeyarestatin I

IUPAC/Chemical Name: 2-[3-(4-Chlorophenyl)-4-[hydroxy(methyl)amino]-5,5-dimethyl-2-oxoimidazolidin-1-yl]-N-[(E)-[(E)-3-(5-nitrofuran-2-yl)prop-2-enylidene]amino]acetamide


InChi Code: InChI=1S/C21H23ClN6O6/c1-21(2)19(25(3)31)27(15-8-6-14(22)7-9-15)20(30)26(21)13-17(29)24-23-12-4-5-16-10-11-18(34-16)28(32)33/h4-12,19,31H,13H2,1-3H3,(H,24,29)/b5-4+,23-12+

SMILES Code: O=C(N/N=C/C=C/C1=CC=C([N+]([O-])=O)O1)CN2C(C)(C)C(N(O)C)N(C3=CC=C(Cl)C=C3)C2=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 30.0 61.11

Preparing Stock Solutions

The following data is based on the product molecular weight 490.901 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ding R, Zhang T, Xie J, Williams J, Ye Y, Chen L. Eeyarestatin I derivatives with improved aqueous solubility. Bioorg Med Chem Lett. 2016 Nov 1;26(21):5177-5181. doi: 10.1016/j.bmcl.2016.09.068. Epub 2016 Sep 29. PubMed PMID: 27729187.

2: Berry GE, Asokan A. Chemical Modulation of Endocytic Sorting Augments Adeno-associated Viral Transduction. J Biol Chem. 2016 Jan 8;291(2):939-47. doi: 10.1074/jbc.M115.687657. Epub 2015 Nov 2. PubMed PMID: 26527686; PubMed Central PMCID: PMC4705411.

3: Meinig JM, Fu L, Peterson BR. Synthesis of Fluorophores that Target Small Molecules to the Endoplasmic Reticulum of Living Mammalian Cells. Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9696-9. doi: 10.1002/anie.201504156. Epub 2015 Jun 26. PubMed PMID: 26118368; PubMed Central PMCID: PMC4539238.

4: Shah PP, Beverly LJ. Regulation of VCP/p97 demonstrates the critical balance between cell death and epithelial-mesenchymal transition (EMT) downstream of ER stress. Oncotarget. 2015 Jul 10;6(19):17725-37. PubMed PMID: 25970786; PubMed Central PMCID: PMC4627341.

5: Han DY, Di XJ, Fu YL, Mu TW. Combining valosin-containing protein (VCP) inhibition and suberanilohydroxamic acid (SAHA) treatment additively enhances the folding, trafficking, and function of epilepsy-associated γ-aminobutyric acid, type A (GABAA) receptors. J Biol Chem. 2015 Jan 2;290(1):325-37. doi: 10.1074/jbc.M114.580324. Epub 2014 Nov 18. PubMed PMID: 25406314; PubMed Central PMCID: PMC4281735.

6: Babajani G, Kermode AR. Alteration of the proteostasis network of plant cells promotes the post-endoplasmic reticulum trafficking of recombinant mutant (L444P) human β-glucocerebrosidase. Plant Signal Behav. 2014;9(3):e28714. Epub 2014 Apr 8. PubMed PMID: 24713615; PubMed Central PMCID: PMC4091198.

7: Arrojo E Drigo R, Egri P, Jo S, Gereben B, Bianco AC. The type II deiodinase is retrotranslocated to the cytoplasm and proteasomes via p97/Atx3 complex. Mol Endocrinol. 2013 Dec;27(12):2105-15. doi: 10.1210/me.2013-1281. Epub 2013 Nov 6. PubMed PMID: 24196352; PubMed Central PMCID: PMC3857201.

8: Minogue PJ, Beyer EC, Berthoud VM. A connexin50 mutant, CX50fs, that causes cataracts is unstable, but is rescued by a proteasomal inhibitor. J Biol Chem. 2013 Jul 12;288(28):20427-34. doi: 10.1074/jbc.M113.452847. Epub 2013 May 17. PubMed PMID: 23720739; PubMed Central PMCID: PMC3711308.

9: Shinjo S, Mizotani Y, Tashiro E, Imoto M. Comparative analysis of the expression patterns of UPR-target genes caused by UPR-inducing compounds. Biosci Biotechnol Biochem. 2013;77(4):729-35. Epub 2013 Apr 7. PubMed PMID: 23563539.

10: Lopez-Castejon G, Luheshi NM, Compan V, High S, Whitehead RC, Flitsch S, Kirov A, Prudovsky I, Swanton E, Brough D. Deubiquitinases regulate the activity of caspase-1 and interleukin-1β secretion via assembly of the inflammasome. J Biol Chem. 2013 Jan 25;288(4):2721-33. doi: 10.1074/jbc.M112.422238. Epub 2012 Dec 3. PubMed PMID: 23209292; PubMed Central PMCID: PMC3554938.

11: Brem GJ, Mylonas I, Brüning A. Eeyarestatin causes cervical cancer cell sensitization to bortezomib treatment by augmenting ER stress and CHOP expression. Gynecol Oncol. 2013 Feb;128(2):383-90. doi: 10.1016/j.ygyno.2012.10.021. Epub 2012 Oct 26. PubMed PMID: 23107612.

12: Chung DW, Ponts N, Prudhomme J, Rodrigues EM, Le Roch KG. Characterization of the ubiquitylating components of the human malaria parasite's protein degradation pathway. PLoS One. 2012;7(8):e43477. doi: 10.1371/journal.pone.0043477. Epub 2012 Aug 17. PubMed PMID: 22912882; PubMed Central PMCID: PMC3422240.

13: Johnson N, Vilardi F, Lang S, Leznicki P, Zimmermann R, High S. TRC40 can deliver short secretory proteins to the Sec61 translocon. J Cell Sci. 2012 Aug 1;125(Pt 15):3612-20. Epub 2012 Apr 14. Erratum in: J Cell Sci. 2012 Sep 15;125(Pt 18):4414. PubMed PMID: 22505607; PubMed Central PMCID: PMC3445324.

14: Valle CW, Min T, Bodas M, Mazur S, Begum S, Tang D, Vij N. Critical role of VCP/p97 in the pathogenesis and progression of non-small cell lung carcinoma. PLoS One. 2011;6(12):e29073. doi: 10.1371/journal.pone.0029073. Epub 2011 Dec 22. PubMed PMID: 22216170; PubMed Central PMCID: PMC3245239.

15: McKibbin C, Mares A, Piacenti M, Williams H, Roboti P, Puumalainen M, Callan AC, Lesiak-Mieczkowska K, Linder S, Harant H, High S, Flitsch SL, Whitehead RC, Swanton E. Inhibition of protein translocation at the endoplasmic reticulum promotes activation of the unfolded protein response. Biochem J. 2012 Mar 15;442(3):639-48. doi: 10.1042/BJ20111220. PubMed PMID: 22145777; PubMed Central PMCID: PMC3286858.

16: Wang F, Song W, Brancati G, Segatori L. Inhibition of endoplasmic reticulum-associated degradation rescues native folding in loss of function protein misfolding diseases. J Biol Chem. 2011 Dec 16;286(50):43454-64. doi: 10.1074/jbc.M111.274332. Epub 2011 Oct 17. PubMed PMID: 22006919; PubMed Central PMCID: PMC3234808.

17: Aletrari MO, McKibbin C, Williams H, Pawar V, Pietroni P, Lord JM, Flitsch SL, Whitehead R, Swanton E, High S, Spooner RA. Eeyarestatin 1 interferes with both retrograde and anterograde intracellular trafficking pathways. PLoS One. 2011;6(7):e22713. doi: 10.1371/journal.pone.0022713. Epub 2011 Jul 25. PubMed PMID: 21799938; PubMed Central PMCID: PMC3143184.

18: Wang Q, Shinkre BA, Lee JG, Weniger MA, Liu Y, Chen W, Wiestner A, Trenkle WC, Ye Y. The ERAD inhibitor Eeyarestatin I is a bifunctional compound with a membrane-binding domain and a p97/VCP inhibitory group. PLoS One. 2010 Nov 12;5(11):e15479. doi: 10.1371/journal.pone.0015479. PubMed PMID: 21124757; PubMed Central PMCID: PMC2993181.

19: Griciuc A, Aron L, Roux MJ, Klein R, Giangrande A, Ueffing M. Inactivation of VCP/ter94 suppresses retinal pathology caused by misfolded rhodopsin in Drosophila. PLoS Genet. 2010 Aug 26;6(8). pii: e1001075. doi: 10.1371/journal.pgen.1001075. PubMed PMID: 20865169; PubMed Central PMCID: PMC2928793.

20: Cross BC, McKibbin C, Callan AC, Roboti P, Piacenti M, Rabu C, Wilson CM, Whitehead R, Flitsch SL, Pool MR, High S, Swanton E. Eeyarestatin I inhibits Sec61-mediated protein translocation at the endoplasmic reticulum. J Cell Sci. 2009 Dec 1;122(Pt 23):4393-400. doi: 10.1242/jcs.054494. Epub 2009 Nov 10. PubMed PMID: 19903691; PubMed Central PMCID: PMC2779136.