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

• ChemBase ID: 106308
• Molecular Formular: C30H36F3N9O6
• Molecular Mass: 675.6587496
• Monoisotopic Mass: 675.27406458
• SMILES: NC(=N)NCCC[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: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CCCNC(=N)N
• InChI: InChI=1S/C30H36F3N9O6/c31-30(32,33)20-15-24(43)48-23-14-18(10-11-19(20)23)40-25(44)21(8-4-12-38-27(34)35)41-26(45)22(9-5-13-39-28(36)37)42-29(46)47-16-17-6-2-1-3-7-17/h1-3,6-7,10-11,14-15,21-22H,4-5,8-9,12-13,16H2,(H,40,44)(H,41,45)(H,42,46)(H4,34,35,38)(H4,36,37,39)/t21-,22-/m0/s1
• InChIKey: NPCWNQGCRWSNGB-VXKWHMMOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105489
• PubChem CID: 25108529

CALCULATED PROPERTIES

• Acid pKa: 11.39991
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -3.695666
• LogD (pH = 7.4): -3.6867592
• Log P: 0.5781762
• Molar Refractivity: 189.3087 cm^3
• Polarizability: 62.673824 Å^3
• Polar Surface Area: 246.63 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC051

HYGROSCOPIC. Store in desiccator. A fluorogenic substrate for Cathepsin B.

REFERENCES

• Trabandt, A. et al., Arth. and Rheum., 34(11):1444 (1991).
• Hasnain, S. et al., Biol. Chem. Hoppe-Seyler, 373:413 (1992).
• Smith, R.E. et al., Antican. Res., 8:525 (1988).