benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}-3-methylbutyl]carbamate

• ChemBase ID: 106556
• Molecular Formular: C31H40N6O5
• Molecular Mass: 576.6865
• Monoisotopic Mass: 576.30601841
• SMILES: COc1cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)OCc2ccccc2)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc2ccccc2)CC(C)C)CCCNC(=N)N)cc2c1cccc2
• InChI: InChI=1S/C31H40N6O5/c1-20(2)16-26(37-31(40)42-19-21-10-5-4-6-11-21)29(39)36-25(14-9-15-34-30(32)33)28(38)35-23-17-22-12-7-8-13-24(22)27(18-23)41-3/h4-8,10-13,17-18,20,25-26H,9,14-16,19H2,1-3H3,(H,35,38)(H,36,39)(H,37,40)(H4,32,33,34)/t25-,26-/m0/s1
• InChIKey: QYBJEDHFUWYTQH-UIOOFZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}-3-methylbutyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-[(4-methoxynaphthalen-2-yl)carbamoyl]butyl]carbamoyl}-3-methylbutyl]carbamate
• Synonyms: Z-Leu-Arg-MNA; Z-LR-MNA; Z-Leu-Arg-4-Methoxy-2-Naphthylamine

Database IDs

• PubChem SID: 162105968
• PubChem CID: 25108713

CALCULATED PROPERTIES

• Acid pKa: 12.428433
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 1.2419473
• LogD (pH = 7.4): 1.2457147
• Log P: 3.29694
• Molar Refractivity: 171.7648 cm^3
• Polarizability: 63.027477 Å^3
• Polar Surface Area: 167.66 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA053

A fluorogenic/colorimetric substrate for Cathepsin K, S and V.

REFERENCES

• Bromme, D. et al., J. Biol. Chem., 271:2126 (1996).
• Bromme, D. et al., Biochem., 38:2377 (1997).