4-[2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido)-4-methylpentanamido]-4-[(naphthalen-2-yl)carbamoyl]butanoic acid

• ChemBase ID: 133673
• Molecular Formular: C35H44N4O7
• Molecular Mass: 632.74646
• Monoisotopic Mass: 632.32099977
• SMILES: CC(C)CC(C(=O)NC(CCC(=O)O)C(=O)Nc1ccc2ccccc2c1)NC(=O)C(CC(C)C)NC(=O)OCc1ccccc1
• Canonical SMILES: CC(CC(C(=O)NC(C(=O)Nc1ccc2c(c1)cccc2)CCC(=O)O)NC(=O)C(NC(=O)OCc1ccccc1)CC(C)C)C
• InChI: InChI=1S/C35H44N4O7/c1-22(2)18-29(38-34(44)30(19-23(3)4)39-35(45)46-21-24-10-6-5-7-11-24)33(43)37-28(16-17-31(40)41)32(42)36-27-15-14-25-12-8-9-13-26(25)20-27/h5-15,20,22-23,28-30H,16-19,21H2,1-4H3,(H,36,42)(H,37,43)(H,38,44)(H,39,45)(H,40,41)
• InChIKey: MIYHULQEZFNUGE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido)-4-methylpentanamido]-4-[(naphthalen-2-yl)carbamoyl]butanoic acid
• IUPAC Traditional name: 4-[2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido)-4-methylpentanamido]-4-[(naphthalen-2-yl)carbamoyl]butanoic acid
• Synonyms: Cbz-LLE β-naphthylamine; Z-Leu-Leu-Glu β-naphthylamide

Database IDs

• CAS Number: 75873-85-7
• MDL Number: MFCD00058505
• PubChem SID: 162227950; 24892275
• PubChem CID: 4091799

CALCULATED PROPERTIES

• Acid pKa: 4.0646744
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 3.6422133
• LogD (pH = 7.4): 1.968895
• Log P: 5.0897098
• Molar Refractivity: 173.6372 cm^3
• Polarizability: 68.44052 Å^3
• Polar Surface Area: 162.93 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - C0788

Amino Acid Sequence
Z-Leu-Leu-Glu-βNA
Substrates
Substrate for the glutamylpeptidyl-peptide hydrolase activity of the 20S proteasome (multicatalytic proteinase complex).