clasto-Lactacystin beta-lactone, 20S proteasome inhibitor

Key facts

CAS number

154226-60-5

Purity

>95%

Form

Solid

form

Molecular weight

213.23 Da

Molecular formula

C₁₀H₁₅NO₄

PubChem

9794358

Nature

Synthetic

Solubility

Soluble in DMSO to 75 mM

Soluble in water to 10 mM

Biochemical name

Clasto-lactacystin beta-lactone

Biological description

Potent, irreversible and cell-permeable 20S proteasome inhibitor (IC₅₀ = 50 nM). Active metabolite of lactacystin (ab141411). Inhibits cell-cycle progression in cancer cells. Antitumor agent. Active in vivo and in vitro.

Canonical smiles

CC1C2C(C(=O)O2)(NC1=O)C(C(C)C)O

Isomeric smiles

C[C@@H]1[C@H]2[C@](C(=O)O2)(NC1=O)[C@H](C(C)C)O

InChi

InChI=1S/C10H15NO4/c1-4(2)6(12)10-7(15-9(10)14)5(3)8(13)11-10/h4-7,12H,1-3H3,(H,11,13)/t5-,6+,7+,10-/m1/s1

InChiKey

FWPWHHUJACGNMZ-NBBQQVJHSA-N

IUPAC Name

(1R,4R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione