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

• ChemBase ID: 106312
• Molecular Formular: C33H41F3N10O7
• Molecular Mass: 746.7366496
• Monoisotopic Mass: 746.31117836
• SMILES: C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)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)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C33H41F3N10O7/c1-18(43-32(51)52-17-19-7-3-2-4-8-19)27(48)45-24(10-6-14-42-31(39)40)29(50)46-23(9-5-13-41-30(37)38)28(49)44-20-11-12-21-22(33(34,35)36)16-26(47)53-25(21)15-20/h2-4,7-8,11-12,15-16,18,23-24H,5-6,9-10,13-14,17H2,1H3,(H,43,51)(H,44,49)(H,45,48)(H,46,50)(H4,37,38,41)(H4,39,40,42)/t18-,23-,24-/m0/s1
• InChIKey: PWPGGFDNLWOQAK-NWVWQQAFSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105391
• PubChem CID: 25108533

CALCULATED PROPERTIES

• Acid pKa: 12.180097
• H Acceptors: 11
• H Donor: 10
• LogD (pH = 5.5): -4.232169
• LogD (pH = 7.4): -4.2220097
• Log P: 0.01091189
• Molar Refractivity: 206.6061 cm^3
• Polarizability: 69.4477 Å^3
• Polar Surface Area: 275.73 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC055

A fluorogenic substrate for Cathepsin B.

REFERENCES

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