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

• ChemBase ID: 106555
• Molecular Formular: C34H38N6O5
• Molecular Mass: 610.70272
• Monoisotopic Mass: 610.29036835
• SMILES: COc1cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)CCCNC(=N)N)cc2c1cccc2
• InChI: InChI=1S/C34H38N6O5/c1-44-30-21-26(20-25-15-8-9-16-27(25)30)38-31(41)28(17-10-18-37-33(35)36)39-32(42)29(19-23-11-4-2-5-12-23)40-34(43)45-22-24-13-6-3-7-14-24/h2-9,11-16,20-21,28-29H,10,17-19,22H2,1H3,(H,38,41)(H,39,42)(H,40,43)(H4,35,36,37)/t28-,29-/m0/s1
• InChIKey: SKVCFQIWNJKEDN-VMPREFPWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105521
• PubChem CID: 25108712

CALCULATED PROPERTIES

• Acid pKa: 12.403241
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 1.6441641
• LogD (pH = 7.4): 1.6479777
• Log P: 3.69394
• Molar Refractivity: 182.7102 cm^3
• Polarizability: 67.09546 Å^3
• Polar Surface Area: 167.66 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA052

A fluorogenic/colorimetric substrate for Cathepsin C.

REFERENCES

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