benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]carbamoyl}butyl]carbamoyl}ethyl]carbamate

• ChemBase ID: 106412
• Molecular Formular: C33H44N10O7
• Molecular Mass: 692.76526
• Monoisotopic Mass: 692.3394438
• SMILES: C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C33H44N10O7/c1-19-16-27(44)50-26-17-22(12-13-23(19)26)41-29(46)24(10-6-14-38-31(34)35)43-30(47)25(11-7-15-39-32(36)37)42-28(45)20(2)40-33(48)49-18-21-8-4-3-5-9-21/h3-5,8-9,12-13,16-17,20,24-25H,6-7,10-11,14-15,18H2,1-2H3,(H,40,48)(H,41,46)(H,42,45)(H,43,47)(H4,34,35,38)(H4,36,37,39)/t20-,24-,25-/m0/s1
• InChIKey: RACPARIFVUIBCA-OPXMRZJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]butyl]carbamoyl}butyl]carbamoyl}ethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]butyl]carbamoyl}butyl]carbamoyl}ethyl]carbamate
• Synonyms: Z-Ala-Arg-Arg-AMC; Z-ARR-AMC; Z-Ala-Arg-Arg-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105697
• PubChem CID: 25108603

CALCULATED PROPERTIES

• Acid pKa: 12.224881
• H Acceptors: 11
• H Donor: 10
• LogD (pH = 5.5): -4.59662
• LogD (pH = 7.4): -4.588308
• Log P: -0.33142036
• Molar Refractivity: 205.6736 cm^3
• Polarizability: 70.07218 Å^3
• Polar Surface Area: 275.73 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC055

A fluorogenic 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. and Berg, M.J. et al., Arch. Biochem. and Biophys., 259:131 (1987).