benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamate

• ChemBase ID: 106310
• Molecular Formular: C30H35F3N6O6
• Molecular Mass: 632.6307096
• Monoisotopic Mass: 632.25701753
• SMILES: CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C30H35F3N6O6/c1-17(2)13-23(39-29(43)44-16-18-7-4-3-5-8-18)27(42)38-22(9-6-12-36-28(34)35)26(41)37-19-10-11-20-21(30(31,32)33)15-25(40)45-24(20)14-19/h3-5,7-8,10-11,14-15,17,22-23H,6,9,12-13,16H2,1-2H3,(H,37,41)(H,38,42)(H,39,43)(H4,34,35,36)/t22-,23-/m0/s1
• InChIKey: FPXKSVQUCFQUMV-GOTSBHOMSA-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}-3-methylbutyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamate
• Synonyms: Z-Leu-Arg-AFC; Z-LR-AFC; Z-Leu-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105390
• PubChem CID: 25108531

CALCULATED PROPERTIES

• Acid pKa: 11.538206
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 0.8841029
• LogD (pH = 7.4): 0.8898543
• Log P: 2.8505878
• Molar Refractivity: 169.5565 cm^3
• Polarizability: 59.586838 Å^3
• Polar Surface Area: 184.73 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC053

A fluorogenic substrate for Cathepsins K,S and V.

REFERENCES

• Bromme, D. et al., J. Biol. Chem., 271:2126 (1996).
• Bromme, D. et al., Biochem., 38:2377 (1997).