benzyl N-[(1S)-1-{[(2S)-4-fluoro-3-oxobutan-2-yl]carbamoyl}-2-phenylethyl]carbamate

• ChemBase ID: 106523
• Molecular Formular: C21H23FN2O4
• Molecular Mass: 386.4167232
• Monoisotopic Mass: 386.16418545
• SMILES: C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)CF
• Canonical SMILES: FCC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C21H23FN2O4/c1-15(19(25)13-22)23-20(26)18(12-16-8-4-2-5-9-16)24-21(27)28-14-17-10-6-3-7-11-17/h2-11,15,18H,12-14H2,1H3,(H,23,26)(H,24,27)/t15-,18-/m0/s1
• InChIKey: ASXVEBPEZMSPHB-YJBOKZPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(2S)-4-fluoro-3-oxobutan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(2S)-4-fluoro-3-oxobutan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• Synonyms: Z-Phe-Ala-FMK; Z-FA-FMK; Z-Phe-Ala-Fluoromethylketone; Z-Phe-Ala fluoromethyl ketone

Database IDs

• CAS Number: 96922-64-4
• MDL Number: MFCD00883668
• PubChem SID: 162087690
• PubChem CID: 5311161

CALCULATED PROPERTIES

• Acid pKa: 12.239405
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.107176
• LogD (pH = 7.4): 3.1071706
• Log P: 3.107176
• Molar Refractivity: 101.6549 cm^3
• Polarizability: 39.398052 Å^3
• Polar Surface Area: 84.5 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO or DMF: soluble20 mM
• Apperance: white to off-white powder

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)
• Shipped in: dry ice
• Linear Formula: C21H23N2O4F

DETAILS

MP Biomedicals - 03FK029

A cell-permeable, irreversible cathepsin B inhibitor. Blocks LPS-induced production of IL-1a and IL-1b. Suitable as a negative control for caspase-1 and caspase-2 inhibitors because it lacks an aspartic acid residue at the P1 position.

Sigma Aldrich - C1480

Application
An inhibitor of cysteine proteases, such as cathepsin B, which do not require a P1 Asp residue. It may be used as a negative control inhibitor for FMK P1 Asp caspase inhibitors.

REFERENCES

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