benzyl N-[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}butyl]carbamate

• ChemBase ID: 106554
• Molecular Formular: C31H41N9O5
• Molecular Mass: 619.71454
• Monoisotopic Mass: 619.32306546
• SMILES: COc1cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc2ccccc2)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc2ccccc2)CCCNC(=N)N)CCCNC(=N)N)cc2c1cccc2
• InChI: InChI=1S/C31H41N9O5/c1-44-26-18-22(17-21-11-5-6-12-23(21)26)38-27(41)24(13-7-15-36-29(32)33)39-28(42)25(14-8-16-37-30(34)35)40-31(43)45-19-20-9-3-2-4-10-20/h2-6,9-12,17-18,24-25H,7-8,13-16,19H2,1H3,(H,38,41)(H,39,42)(H,40,43)(H4,32,33,36)(H4,34,35,37)/t24-,25-/m0/s1
• InChIKey: UGENMPCCAUJPMX-DQEYMECFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}butyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}butyl]carbamate
• Synonyms: Z-Arg-Arg-MNA; Z-RR-MNA; Z-Arg-Arg-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105716
• PubChem CID: 22845249

CALCULATED PROPERTIES

• Acid pKa: 12.52824
• H Acceptors: 10
• H Donor: 9
• LogD (pH = 5.5): -3.3378208
• LogD (pH = 7.4): -3.3308322
• Log P: 0.93336314
• Molar Refractivity: 191.517 cm^3
• Polarizability: 66.04305 Å^3
• Polar Surface Area: 229.56 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA051

A fluorogenic/colorimetric 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).