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

• ChemBase ID: 106522
• Molecular Formular: C27H27FN2O4
• Molecular Mass: 462.5126832
• Monoisotopic Mass: 462.19548557
• SMILES: FCC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1
• Canonical SMILES: FCC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)Cc1ccccc1
• InChI: InChI=1S/C27H27FN2O4/c28-18-25(31)23(16-20-10-4-1-5-11-20)29-26(32)24(17-21-12-6-2-7-13-21)30-27(33)34-19-22-14-8-3-9-15-22/h1-15,23-24H,16-19H2,(H,29,32)(H,30,33)/t23-,24-/m0/s1
• InChIKey: CAILNONEKASNSH-ZEQRLZLVSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD03453604
• PubChem SID: 162105585
• PubChem CID: 11705307

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.7635026
• LogD (pH = 7.4): 4.7634964
• Log P: 4.7635026
• Molar Refractivity: 126.2739 cm^3
• Polarizability: 48.956646 Å^3
• Polar Surface Area: 84.5 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true
• Acid pKa: 12.203494

PROPERTIES

Physical Property

• 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: ≥98% (TLC)
• Empirical Formula (Hill Notation): C27H27N2O4F

DETAILS

MP Biomedicals - 03FK028

An inhibitor for Cathepsin B and L.

Sigma Aldrich - C9109

Amino Acid Sequence
Z-Phe-Phe-FMK
Application
Cathepsin B and Cathepsin L inhibitor

REFERENCES

• Esser, R. et al., J. of Rheumatology, 20(7):1176 (1993).
• Esser, R.E. et al., Arthritis Rheum., 37(21):236 (1994).