Epoxomicin, 20S proteasome inhibitor

Key facts

CAS number

134381-21-8

Purity

>97%

Source

Actinomyces sp.

Molecular weight

554.7 Da

Molecular formula

C₂₈H₅₀N₄O₇

PubChem

3035402

Nature

Native

Solubility

Soluble in DMSO to 10 mM

Biochemical name

(2S,3S)-2-(Acetyl-methyl-amino)-3-methyl-pentanoic acid ((S)-1-{(R)-(R)-2-hydroxy-1-[(R)-3-methyl-1-((R)-2-methyl-oxiranecarbonyl)-butylcarbamoyl]-propylcarbamoyl}-2-methyl-butyl)-amide

Biological description

Potent, selective, irreversible and cell-permeable 20S proteasome inhibitor (IC₅₀ = 4 nM). Predominantly inhibits the chymotrypsin-like activity. Anti-inflammatory and antitumor agent. Active in vitro and in vivo.

Canonical smiles

CCC(C)C(C(=O)NC(=O)C(C(C)O)NC(CC(C)C)C(=O)C1(CO1)C)NC(=O)C(C(C)CC)N(C)C(=O)C

Isomeric smiles

CC[C@H](C)[C@@H](C(=O)NC(=O)[C@H]([C@@H](C)O)NC(CC(C)C)C(=O)[C@]1(CO1)C)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)C

InChi

InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-26(37)22(18(7)33)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,29,33H,11-14H2,1-10H3,(H,30,38)(H,31,36,37)/t16-,17-,18+,20?,21-,22-,23-,28+/m0/s1

InChiKey

ZWCBKZGIPPDRLY-TXLQCSLMSA-N

IUPAC Name

(2S,3S)-2-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-N-[(2S,3R)-3-hydroxy-2-[[4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]butanoyl]-3-methylpentanamide