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

• ChemBase ID: 106457
• Molecular Formular: C34H45N7O7
• Molecular Mass: 663.7638
• Monoisotopic Mass: 663.33804682
• SMILES: CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C34H45N7O7/c1-19(2)28(40-32(45)29(20(3)4)41-34(46)47-18-22-10-7-6-8-11-22)31(44)39-25(12-9-15-37-33(35)36)30(43)38-23-13-14-24-21(5)16-27(42)48-26(24)17-23/h6-8,10-11,13-14,16-17,19-20,25,28-29H,9,12,15,18H2,1-5H3,(H,38,43)(H,39,44)(H,40,45)(H,41,46)(H4,35,36,37)/t25-,28-,29-/m0/s1
• InChIKey: VCOVUYXJMHMVNV-FMYROPPKSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105963
• PubChem CID: 25108644

CALCULATED PROPERTIES

• Acid pKa: 12.070856
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): 0.5040307
• LogD (pH = 7.4): 0.50929075
• Log P: 2.4438136
• Molar Refractivity: 190.239 cm^3
• Polarizability: 68.85681 Å^3
• Polar Surface Area: 213.83 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC245

A fluorogenic substrate for Cathepsin S.

REFERENCES

• Bromme, D. et al., Biochem., 264:475 (1989).