benzyl N-[(1S)-1-{[(1S)-1-{[(3S)-1-fluoro-5-methyl-2-oxohexan-3-yl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamate

• ChemBase ID: 106514
• Molecular Formular: C27H42FN3O5
• Molecular Mass: 507.6378832
• Monoisotopic Mass: 507.31084968
• SMILES: CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C(=O)CF
• Canonical SMILES: FCC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)CC(C)C)CC(C)C
• InChI: InChI=1S/C27H42FN3O5/c1-17(2)12-21(24(32)15-28)29-25(33)22(13-18(3)4)30-26(34)23(14-19(5)6)31-27(35)36-16-20-10-8-7-9-11-20/h7-11,17-19,21-23H,12-16H2,1-6H3,(H,29,33)(H,30,34)(H,31,35)/t21-,22-,23-/m0/s1
• InChIKey: HLXJVMRDGBCZCM-VABKMULXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(1S)-1-{[(3S)-1-fluoro-5-methyl-2-oxohexan-3-yl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(1S)-1-{[(3S)-1-fluoro-5-methyl-2-oxohexan-3-yl]carbamoyl}-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamate
• Synonyms: Z-Leu-Leu-Leu-FMK; Z-LLL-FMK; Z-Leu-Leu-Leu-Fluoromethylketone; Z-Leu-Leu-Leu-fluoromethyl ketone

Database IDs

• MDL Number: MFCD03453603
• PubChem SID: 162106011
• PubChem CID: 11555247

CALCULATED PROPERTIES

• Acid pKa: 12.04407
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 4.676661
• LogD (pH = 7.4): 4.6766524
• Log P: 4.6766615
• Molar Refractivity: 135.3541 cm^3
• Polarizability: 53.12192 Å^3
• Polar Surface Area: 113.6 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

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: ≥90% (TLC)
• Empirical Formula (Hill Notation): C27H42N3O5F

DETAILS

MP Biomedicals - 03FK020

An inhibitor for Proteasomes

Sigma Aldrich - C8984

Amino Acid Sequence
Z-Leu-Leu-Leu-FMK
Biochem/physiol Actions
Z-Leu-Leu-Leu-fluoromethyl ketone is a proteosome inhibitor.

REFERENCES

• Steinhilb, ml. et al. J. Biol. Chem., 276:4476 (2001).
• Meriin, AB. et al. J. Biol. Chem., 273:6373 (1998).