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

• ChemBase ID: 106337
• Molecular Formular: C33H49F3N10O7
• Molecular Mass: 754.8001696
• Monoisotopic Mass: 754.37377862
• SMILES: CC(C)C[C@H](NC(=O)OC(C)(C)C)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: CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)CCCNC(=N)N)NC(=O)OC(C)(C)C)C
• InChI: InChI=1S/C33H49F3N10O7/c1-17(2)14-23(46-31(51)53-32(3,4)5)28(50)45-22(9-7-13-42-30(39)40)27(49)44-21(8-6-12-41-29(37)38)26(48)43-18-10-11-19-20(33(34,35)36)16-25(47)52-24(19)15-18/h10-11,15-17,21-23H,6-9,12-14H2,1-5H3,(H,43,48)(H,44,49)(H,45,50)(H,46,51)(H4,37,38,41)(H4,39,40,42)/t21-,22-,23-/m0/s1
• InChIKey: CUNYWAFDJKXXEP-VABKMULXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamate
• Synonyms: Boc-Leu-Arg-Arg-AFC; Boc-LRR-AFC; Boc-Leu-Arg-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105954
• PubChem CID: 25108557

CALCULATED PROPERTIES

• Acid pKa: 12.202899
• H Acceptors: 11
• H Donor: 10
• LogD (pH = 5.5): -3.6485767
• LogD (pH = 7.4): -3.6387448
• Log P: 0.6052639
• Molar Refractivity: 209.4727 cm^3
• Polarizability: 70.91234 Å^3
• Polar Surface Area: 275.73 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC113

A fluorogenic substrate for Cathepsin B.

REFERENCES

• Mizuno, K. et al., Biochem. Biophys. Res. Comm., 144:807 (1987).
• Mizuno, K. et al., Biochem. Biophys. Res. Comm., 159:305 (1989).