benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}-2-phenylethyl]carbamate

• ChemBase ID: 106309
• Molecular Formular: C33H33F3N6O6
• Molecular Mass: 666.6469296
• Monoisotopic Mass: 666.24136747
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C33H33F3N6O6/c34-33(35,36)24-18-28(43)48-27-17-22(13-14-23(24)27)40-29(44)25(12-7-15-39-31(37)38)41-30(45)26(16-20-8-3-1-4-9-20)42-32(46)47-19-21-10-5-2-6-11-21/h1-6,8-11,13-14,17-18,25-26H,7,12,15-16,19H2,(H,40,44)(H,41,45)(H,42,46)(H4,37,38,39)/t25-,26-/m0/s1
• InChIKey: WXSWRWRSKKNURZ-UIOOFZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}-2-phenylethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}-2-phenylethyl]carbamate
• Synonyms: Z-Phe-Arg-AFC; Z-FR-AFC; Z-Phe-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• CAS Number: 65147-22-0
• PubChem SID: 162092923
• PubChem CID: 25108530

CALCULATED PROPERTIES

• Acid pKa: 11.53706
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 1.2863191
• LogD (pH = 7.4): 1.2920771
• Log P: 3.250952
• Molar Refractivity: 180.5019 cm^3
• Polarizability: 63.59414 Å^3
• Polar Surface Area: 184.73 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC052

A fluorogenic substrate for Cathepsin L and Kallikrein.

REFERENCES

• Maciewica, et al., Biomed. Biochem. Acta., 50:564 (1991).
• McDonald, J.K. et al., Biochem. Biophys. Res. Comm., 151:827 (1988).
• Marks, N. et al., Arch. Biochem. and Biophys., 259:131 (1987).