(1R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4,4-bis(2H3)methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

• ChemBase ID: 173079
• Molecular Formular: C11H17NO4
• Molecular Mass: 227.25698
• Monoisotopic Mass: 227.11575803
• SMILES: [C@]12([C@@H](OC1=O)C(C(=O)N2)(C)C)[C@H](C(C)C)O
• Canonical SMILES: CC([C@@H]([C@]12NC(=O)C([C@@H]2OC1=O)(C)C)O)C
• InChI: InChI=1S/C11H17NO4/c1-5(2)6(13)11-7(16-9(11)15)10(3,4)8(14)12-11/h5-7,13H,1-4H3,(H,12,14)/t6-,7-,11+/m0/s1
• InChIKey: SFIBAAAUUBBTJU-OKTBNZSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4,4-bis(^2H₃)methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• IUPAC Traditional name: (1R,5S)-1-[(1S)-1-hydroxy-2-methylpropyl]-4,4-bis(^2H₃)methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• Synonyms: (1R,5S)-1-[(1S)-1-Hydroxy-2-methylpropyl]-4,4-(dimethyl-d6)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione; (-)-7-Methylomuralide-d6; α-Methyl Omuralide-d6

Database IDs

• PubChem SID: 164228989
• PubChem CID: 71750125

CALCULATED PROPERTIES

• Acid pKa: 10.4539175
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.6447277
• LogD (pH = 7.4): 0.6443923
• Log P: 0.644732
• Molar Refractivity: 54.55 cm^3
• Polarizability: 22.218525 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M265147

A labelled potent, selective, irreversible inhibitor of proteasome function. A cell permeable α-methyl analog of clasto-Lactacytin (C562500).

REFERENCES

• Saravanan, P. et al.: J. Org. Chem. 68, 2760 (2003)
• Corey, E.J., et al.: Tetrahedron Lett. 39, 7475 (2003)