Structure via PubChem · Public domain (PubChem)
Epoxomicin
Sign in to saveEpoxomicin is a naturally occurring selective proteasome inhibitor with anti-inflammatory activity. It was originally discovered in 1992. Injected, it can induce Parkinson's-like symptoms in rats.
Chemical data
- Formula
- C28H50N4O7
- Molecular weight
- 554.7 g/mol
- IUPAC 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
- SMILES
- CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(CO1)C)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)C
- InChIKey
- DOGIDQKFVLKMLQ-JTHVHQAWSA-N
- XLogP
- 2.3
- Polar surface area
- 157 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Protein
via ChEMBL · EBI
Research
415 papers- Heterologous Expression of Epoxomicin in Escherichia coli.ACS synthetic biology · 2024
- From epoxomicin to carfilzomib: chemistry, biology, and medical outcomes.Natural product reports · 2013
- Epoxomicin, a Selective Proteasome Inhibitor, Activates AIM2 Inflammasome in Human Retinal Pigment Epithelium Cells.Antioxidants (Basel, Switzerland) · 2022
- Epoxomicin Sensitizes Resistant Osteosarcoma Cells to TRAIL Induced Apoptosis.Anti-cancer agents in medicinal chemistry · 2015
- Targeted intracellular protein degradation induced by a small molecule: En route to chemical proteomics.Bioorganic & medicinal chemistry letters · 2008
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 554.36794994
Show 4 more facts
- canonical SMILES
- CCC(C)C(C(=O)NC(C(C)O)C(=O)NC(CC(C)C)C(=O)C1(CO1)C)NC(=O)C(C(C)CC)N(C)C(=O)C
- chemical formula
- C₂₈H₅₀N₄O₇
- subject has role
- proteasome inhibitor
- isomeric SMILES
- CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(CO1)C)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- Further reading
Epoxomicin is a naturally occurring selective proteasome inhibitor with anti-inflammatory activity. It was originally discovered in 1992. Injected, it can induce Parkinson's-like symptoms in rats.
Derivatives of epoxomicin include carfilzomib.
Excerpted from Wikipedia’s “Epoxomicin” article, available under the CC BY-SA 4.0 licence.