2-acetamido-3-[3-hydroxy-2-(1-hydroxy-2-methylpropyl)-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid

• ChemBase ID: 106010
• Molecular Formular: C15H24N2O7S
• Molecular Mass: 376.42526
• Monoisotopic Mass: 376.13042212
• SMILES: CC(C)C(O)C1(NC(=O)C(C)C1O)C(=O)SCC(NC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)NC(C(=O)O)CSC(=O)C1(NC(=O)C(C1O)C)C(C(C)C)O
• InChI: InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)
• InChIKey: DAQAKHDKYAWHCG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-[3-hydroxy-2-(1-hydroxy-2-methylpropyl)-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid
• IUPAC Traditional name: 2-acetamido-3-[3-hydroxy-2-(1-hydroxy-2-methylpropyl)-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid
• Synonyms: LACTACYSTIN

Database IDs

• CAS Number: 133343-34-7
• PubChem SID: 162089017
• PubChem CID: 3870

CALCULATED PROPERTIES

• Acid pKa: 3.6403015
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.0795863
• LogD (pH = 7.4): -4.552016
• Log P: -1.2231128
• Molar Refractivity: 88.0327 cm^3
• Polarizability: 35.217537 Å^3
• Polar Surface Area: 153.03 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02195863

Synthetic Cell permeable 20S proteasome inhibitor. Induces neurite outgrowth in mouse neuroblastoma cells and inhibits progression of synchronized Neuro 2A cells and MG-63 human osteosarcoma cells beyond the G₁ phase. Appears to induce apoptosis in human monoblast cells.