benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate

• ChemBase ID: 155683
• Molecular Formular: C29H39N3O5
• Molecular Mass: 509.63706
• Monoisotopic Mass: 509.28897136
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](Cc1ccccc1)C=O)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C29H39N3O5/c1-20(2)15-25(27(34)30-24(18-33)17-22-11-7-5-8-12-22)31-28(35)26(16-21(3)4)32-29(36)37-19-23-13-9-6-10-14-23/h5-14,18,20-21,24-26H,15-17,19H2,1-4H3,(H,30,34)(H,31,35)(H,32,36)/t24-,25-,26-/m0/s1
• InChIKey: LIOIGKLWXFXXEG-GSDHBNRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-3-methyl-1-{[(1S)-3-methyl-1-{[(2S)-1-oxo-3-phenylpropan-2-yl]carbamoyl}butyl]carbamoyl}butyl]carbamate
• Synonyms: Cbz-Leu-Leu-Phe-CHO; Z-LLF-CHO; Z-Leu-Leu-Phe-CHO

Database IDs

• MDL Number: MFCD01862616
• PubChem SID: 162249821
• PubChem CID: 10255743

CALCULATED PROPERTIES

• Acid pKa: 12.380965
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.516792
• LogD (pH = 7.4): 4.516788
• Log P: 4.516792
• Molar Refractivity: 141.8129 cm^3
• Polarizability: 55.619354 Å^3
• Polar Surface Area: 113.6 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C29H39N3O5

DETAILS

Sigma Aldrich - C0358

Amino Acid Sequence
Z-Leu-Leu-Phe-al
Biochem/physiol Actions
Cell permeable proteasome inhibitor acting on the chymotrypsin-like activity of the multicatalytic proteinase complex.
General description
Manufactured for Sigma by Boston Biochem., Inc.