[(1R)-3-methyl-1-[(2R)-3-(2H5)phenyl-2-(pyrazin-2-ylformamido)(2H3)propanamido]butyl]boronic acid

• ChemBase ID: 162700
• Molecular Formular: C19H25BN4O4
• Molecular Mass: 384.2372
• Monoisotopic Mass: 384.1968857
• SMILES: c1cncc(n1)C(=O)N[C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)Cc1ccccc1
• Canonical SMILES: CC(C[C@@H](B(O)O)NC(=O)[C@H](NC(=O)c1cnccn1)Cc1ccccc1)C
• InChI: InChI=1S/C19H25BN4O4/c1-13(2)10-17(20(27)28)24-18(25)15(11-14-6-4-3-5-7-14)23-19(26)16-12-21-8-9-22-16/h3-9,12-13,15,17,27-28H,10-11H2,1-2H3,(H,23,26)(H,24,25)/t15-,17+/m1/s1
• InChIKey: GXJABQQUPOEUTA-WBVHZDCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R)-3-methyl-1-[(2R)-3-(^2H₅)phenyl-2-(pyrazin-2-ylformamido)(^2H₃)propanamido]butyl]boronic acid
• IUPAC Traditional name: (1R)-3-methyl-1-[(2R)-3-(^2H₅)phenyl-2-(pyrazin-2-ylformamido)(^2H₃)propanamido]butylboronic acid
• Synonyms: Velcade-D8, [(1R)-3-Methyl-1-[[(2S)-1-oxo-3-phenyl-2-[(pyrazinylcarbonyl)amino]propyl]amino]butyl]-boronic Acid-D8; Bortezomib-D8 (Major)

Database IDs

• PubChem SID: 162256835
• PubChem CID: 45038428

CALCULATED PROPERTIES

• Acid pKa: 13.037311
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.5302998
• LogD (pH = 7.4): 1.5302991
• Log P: 1.5303
• Molar Refractivity: 99.3738 cm^3
• Polarizability: 40.181385 Å^3
• Polar Surface Area: 124.44 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethanol; Methanol
• Apperance: Off-White Solid
• Melting Point: 115-117°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B675702

Labelled Bortezomib, whcih the first proteasome inhibitor to be approved b the US FDA for multiple myeloma, a blood cancer. A reversible inhibitor of the 26S proteasome-a barrel-shaped multiprotein particle found in the nucleus and cytosol of all eukaryo

REFERENCES

• Nawrocki, S.T., et al: Cancer Research, 65, 11510 (2005)