MedKoo Cat#: 561692 | Name: Epoxomicin

Description:

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

Epoxomicin is an irreversible, selective proteasome inhibitor.

Chemical Structure

Epoxomicin
Epoxomicin
CAS#134381-21-8

Theoretical Analysis

MedKoo Cat#: 561692

Name: Epoxomicin

CAS#: 134381-21-8

Chemical Formula: C28H50N4O7

Exact Mass: 554.3679

Molecular Weight: 554.72

Elemental Analysis: C, 60.63; H, 9.09; N, 10.10; O, 20.19

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Epoxomicin;
IUPAC/Chemical Name
(2S,3S)-2-[[(2S,3S)-2-[Acetyl(methyl)amino]-3-methylpentanoyl]amino]-N-[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]-3-methylpentanamide
InChi Key
DOGIDQKFVLKMLQ-JTHVHQAWSA-N
InChi Code
InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1
SMILES Code
CC[C@H](C)[C@H](NC([C@@H](N(C(C)=O)C)[C@@H](C)CC)=O)C(N[C@@H]([C@H](O)C)C(N[C@@H](CC(C)C)C([C@]1(C)OC1)=O)=O)=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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 554.72 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
1: Kerns K, Morales P, Sutovsky P. Regulation of Sperm Capacitation by the 26S Proteasome: An Emerging New Paradigm in Spermatology. Biol Reprod. 2016 May;94(5):117. doi: 10.1095/biolreprod.115.136622. Epub 2016 Apr 6. Review. PubMed PMID: 27053366. 2: Newman DJ. Developing natural product drugs: Supply problems and how they have been overcome. Pharmacol Ther. 2016 Jun;162:1-9. doi: 10.1016/j.pharmthera.2015.12.002. Epub 2015 Dec 17. Review. PubMed PMID: 26706239. 3: Carmony KC, Kim KB. Activity-based imaging probes of the proteasome. Cell Biochem Biophys. 2013 Sep;67(1):91-101. doi: 10.1007/s12013-013-9626-4. Review. PubMed PMID: 23700161; PubMed Central PMCID: PMC3758798. 4: Kim KB, Crews CM. From epoxomicin to carfilzomib: chemistry, biology, and medical outcomes. Nat Prod Rep. 2013 May;30(5):600-4. doi: 10.1039/c3np20126k. Review. PubMed PMID: 23575525; PubMed Central PMCID: PMC3815659. 5: Morales P, Díaz ES, Kong M. Proteasome activity and its relationship with protein phosphorylation during capacitation and acrosome reaction in human spermatozoa. Soc Reprod Fertil Suppl. 2007;65:269-73. Review. PubMed PMID: 17644968. 6: Ceravolo R, Sgadò P, Frosini D, Corsini GU. Assessing neuroprotection in Parkinson's disease: from the animal models to molecular neuroimaging in vivo. J Neural Transm Suppl. 2006;(71):133-41. Review. PubMed PMID: 17447424. 7: Granot Z, Melamed-Book N, Bahat A, Orly J. Turnover of StAR protein: roles for the proteasome and mitochondrial proteases. Mol Cell Endocrinol. 2007 Feb;265-266:51-8. Epub 2007 Jan 10. Review. PubMed PMID: 17218054. 8: Gough JD, Crews CM. Probing protein function with small molecules. Ernst Schering Res Found Workshop. 2006;(58):61-74. Review. PubMed PMID: 16708999. 9: Kawate H, Ohnaka K, Takayanagi R. [Development of BMP-related drugs]. Nihon Rinsho. 2005 Oct;63 Suppl 10:463-6. Review. Japanese. PubMed PMID: 16279683. 10: Groll M, Huber R. Inhibitors of the eukaryotic 20S proteasome core particle: a structural approach. Biochim Biophys Acta. 2004 Nov 29;1695(1-3):33-44. Review. PubMed PMID: 15571807. 11: Bogyo M, Wang EW. Proteasome inhibitors: complex tools for a complex enzyme. Curr Top Microbiol Immunol. 2002;268:185-208. Review. PubMed PMID: 12083006.