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

• ChemBase ID: 132558
• Molecular Formular: C10H15NO4
• Molecular Mass: 213.2304
• Monoisotopic Mass: 213.10010797
• SMILES: C[C@@H]1[C@H]2[C@](C(=O)O2)(NC1=O)[C@H](C(C)C)O
• Canonical SMILES: CC([C@@H]([C@]12NC(=O)[C@@H]([C@@H]2OC1=O)C)O)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• IUPAC Traditional name: (1R,4R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• Synonyms: clasto-Lactacystin β-lactone; (1R,4R,5S)-1-[(1S)-1-Hydroxy-2-methylpropyl]-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione; Clasto-lactacystin β-Lactone; Omuralide; Clasto-lactacystin(Omuralide)

Database IDs

• CAS Number: 154226-60-5
• MDL Number: MFCD01076526
• PubChem SID: 24896450; 162226835
• PubChem CID: 9794358

CALCULATED PROPERTIES

• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 10.381994
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.08871266
• LogD (pH = 7.4): 0.08831688
• Log P: 0.08871772
• Molar Refractivity: 50.049 cm^3
• Polarizability: 20.396214 Å^3
• Polar Surface Area: 75.63 Å^2

PROPERTIES

Physical Property

• Solubility: DMF; Ethanol; Hot Ethyl Acetate; Methanol; Pyridine
• Apperance: White Solid
• Melting Point: 186-187°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - L7035

Biochem/physiol Actions
Cell-permeable and irreversible proteasome inhibitor. Lactacystin acts as a precursor for clasto-lactacystin β-lactone.

Toronto Research Chemicals - C562500

A cell permeable, irreversible proteasome inhibitor. It is 20-fold more potent than Lactacystin. Lactacytstin spontaneously converts to clasto-lactacystin in biological systems. Clasto-lactacystin is the only cell permeable form of lactacystin. Induce

REFERENCES

• Craiu, A., et al.: J. Biol. Chem., 272, 13437 (1997)
• Dick, G.L.R., et al.: J. Biol. Chem., 272, 182 (1997)
• Fenteany, G. and Schreiber, S.: J. Biol. Chem., 273, 8545 (1997)
• Corey, E.J., et al.: J.A.C.S., 120, 2330 (1998)