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

• ChemBase ID: 106368
• Molecular Formular: C34H42F3N7O7
• Molecular Mass: 717.7351896
• Monoisotopic Mass: 717.30978138
• SMILES: CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C34H42F3N7O7/c1-18(2)27(43-31(48)28(19(3)4)44-33(49)50-17-20-9-6-5-7-10-20)30(47)42-24(11-8-14-40-32(38)39)29(46)41-21-12-13-22-23(34(35,36)37)16-26(45)51-25(22)15-21/h5-7,9-10,12-13,15-16,18-19,24,27-28H,8,11,14,17H2,1-4H3,(H,41,46)(H,42,47)(H,43,48)(H,44,49)(H4,38,39,40)/t24-,27-,28-/m0/s1
• InChIKey: YNPJFGSBIUOIHV-WIRXVTQYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105419
• PubChem CID: 25108587

CALCULATED PROPERTIES

• Acid pKa: 11.43987
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): 0.8684795
• LogD (pH = 7.4): 0.875414
• Log P: 2.7673433
• Molar Refractivity: 191.1715 cm^3
• Polarizability: 68.18231 Å^3
• Polar Surface Area: 213.83 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC245

A fluorogenic substrate for Cathepsin S.

REFERENCES

• Bromme, D. et al., Biochem., 264:475 (1989).