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

• ChemBase ID: 172157
• Molecular Formular: C15H24N2O7S
• Molecular Mass: 376.42526
• Monoisotopic Mass: 376.13042212
• SMILES: C1(=O)[C@@H]([C@@H](C(N1)(C(=O)SC[C@@H](NC(=O)C)C(=O)O)[C@@H](C(C)C)O)O)C
• Canonical SMILES: CC(=O)N[C@@H](C(=O)O)CSC(=O)C1(NC(=O)[C@@H]([C@@H]1O)C)[C@@H](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)/t7-,9-,10-,11+,15?/m1/s1
• InChIKey: DAQAKHDKYAWHCG-DTYGTVRDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid
• IUPAC Traditional name: (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid
• Synonyms: N-Acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-D-prolyl]-L-cysteine; Lactacystin; (+)-Lactacystin

Database IDs

• CAS Number: 133343-34-7
• PubChem SID: 164228067
• PubChem CID: 71749712

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

Physical Property

• Solubility: DMSO; Methanol; Pyridine; Water
• Apperance: White Solid
• Melting Point: >200°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L101000

A selective and potent inhibitor of proteasome-mediated degradation of ubiquitin-tagged proteins. A Streptomyces metabolite that acts as a highly specific inhibitor of the 20S proteasome (MCP: multicatalytic proteinase complex).

REFERENCES

• Fenteany, G., et al.: Science, 268, 726 (1995)
• Fenteany, G., et al.: Proc. Natl. Acad. Sci. USA, 91, 3358 (1995)