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

• ChemBase ID: 106557
• Molecular Formular: C34H46N10O6
• Molecular Mass: 690.79244
• Monoisotopic Mass: 690.36017924
• SMILES: COc1cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)OCc2ccccc2)cc2c1cccc2
• Canonical SMILES: COc1cc(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc2ccccc2)C)CCCNC(=N)N)CCCNC(=N)N)cc2c1cccc2
• InChI: InChI=1S/C34H46N10O6/c1-21(41-34(48)50-20-22-10-4-3-5-11-22)29(45)43-27(15-9-17-40-33(37)38)31(47)44-26(14-8-16-39-32(35)36)30(46)42-24-18-23-12-6-7-13-25(23)28(19-24)49-2/h3-7,10-13,18-19,21,26-27H,8-9,14-17,20H2,1-2H3,(H,41,48)(H,42,46)(H,43,45)(H,44,47)(H4,35,36,39)(H4,37,38,40)/t21-,26-,27-/m0/s1
• InChIKey: FDRPHVPMXLXYNU-PUUVEUEGSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105522
• PubChem CID: 20834230

CALCULATED PROPERTIES

• Acid pKa: 12.268457
• H Acceptors: 11
• H Donor: 10
• LogD (pH = 5.5): -3.874329
• LogD (pH = 7.4): -3.8665054
• Log P: 0.37300757
• Molar Refractivity: 208.81439 cm^3
• Polarizability: 72.79545 Å^3
• Polar Surface Area: 258.66 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MNA055

A fluorogenic/colorimetric substrate for Cathepsin B.

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).