prop-2-en-1-yl (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoate

• ChemBase ID: 172158
• Molecular Formular: C18H28N2O7S
• Molecular Mass: 416.48912
• Monoisotopic Mass: 416.16172225
• SMILES: C1(=O)[C@@H]([C@@H](C(N1)(C(=O)SC[C@H](C(=O)OCC=C)NC(=O)C)[C@@H](C(C)C)O)O)C
• Canonical SMILES: C=CCOC(=O)[C@H](NC(=O)C)CSC(=O)C1(NC(=O)[C@@H]([C@@H]1O)C)[C@@H](C(C)C)O
• InChI: InChI=1S/C18H28N2O7S/c1-6-7-27-16(25)12(19-11(5)21)8-28-17(26)18(13(22)9(2)3)14(23)10(4)15(24)20-18/h6,9-10,12-14,22-23H,1,7-8H2,2-5H3,(H,19,21)(H,20,24)/t10-,12-,13-,14+,18?/m1/s1
• InChIKey: RYUOBJYLYRDIEH-GZIDRAAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-yl (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoate
• IUPAC Traditional name: prop-2-en-1-yl (2S)-2-acetamido-3-[(3S,4R)-3-hydroxy-2-[(1R)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoate
• Synonyms: Lactacystin Allyl Ester; (+)-Lactacystin Allyl Ester

Database IDs

• PubChem SID: 164228068
• PubChem CID: 71749713

CALCULATED PROPERTIES

• Acid pKa: 10.407465
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.34597382
• LogD (pH = 7.4): -0.34634706
• Log P: -0.345969
• Molar Refractivity: 101.9645 cm^3
• Polarizability: 40.668224 Å^3
• Polar Surface Area: 142.03 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; DMSO; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 127-130°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L101030

The precursor to Lactacystin, 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 compl

REFERENCES

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