benzyl N-[(1R)-1-{[(1R)-1-{[(12Z)-8-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-carbamimidamidopentanamido]-12H-10-oxa-5-azatetraphen-12-ylidene]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl]carbamate

• ChemBase ID: 106592
• Molecular Formular: C56H69N13O9
• Molecular Mass: 1068.22876
• Monoisotopic Mass: 1067.53412085
• SMILES: NC(=N)NCCC[C@@H](NC(=O)[C@@H](CC(C)C)NC(=O)OCc1ccccc1)C(=O)/N=c\1/cc2oc3cc(NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](NC(=O)OCc4ccccc4)CC(C)C)ccc3nc2c2c1cccc2
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc1c(n2)c2ccccc2/c(=N\C(=O)[C@H](NC(=O)[C@H](NC(=O)OCc2ccccc2)CC(C)C)CCCNC(=N)N)/c1)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C
• InChI: InChI=1S/C56H69N13O9/c1-33(2)27-44(68-55(74)76-31-35-15-7-5-8-16-35)51(72)65-41(21-13-25-61-53(57)58)49(70)63-37-23-24-40-46(29-37)78-47-30-43(38-19-11-12-20-39(38)48(47)64-40)67-50(71)42(22-14-26-62-54(59)60)66-52(73)45(28-34(3)4)69-56(75)77-32-36-17-9-6-10-18-36/h5-12,15-20,23-24,29-30,33-34,41-42,44-45H,13-14,21-22,25-28,31-32H2,1-4H3,(H,63,70)(H,65,72)(H,66,73)(H,68,74)(H,69,75)(H4,57,58,61)(H4,59,60,62)/b67-43-/t41-,42+,44-,45+/m0/s1
• InChIKey: SYBBLYDOJVMJAV-RDYSOLCBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1R)-1-{[(1R)-1-{[(12Z)-8-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-carbamimidamidopentanamido]-12H-10-oxa-5-azatetraphen-12-ylidene]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl]carbamate
• IUPAC Traditional name: benzyl N-[(1R)-1-{[(1R)-1-{[(12Z)-8-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-carbamimidamidopentanamido]-10-oxa-5-azatetraphen-12-ylidene]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-3-methylbutyl]carbamate
• Synonyms: Z-Leu-Arg-MR; Z-LR-MR; Z-Leu-Arg-Magic Red

Database IDs

• PubChem SID: 162105540
• PubChem CID: 71300130

CALCULATED PROPERTIES

• Acid pKa: 12.157019
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): 0.19756141
• LogD (pH = 7.4): 0.20676349
• Log P: 4.4435334
• Molar Refractivity: 317.2449 cm^3
• Polarizability: 111.96907 Å^3
• Polar Surface Area: 338.78 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MR053

A fluorogenic substrate for Cathepsin L
(Patent# 6,235,493-May 22, 2001)

REFERENCES

• Van Noorden, C.J.F. et al., Anal. Biochem. 252: 71 (1997).
• Boonacker, E. et al., J. Histochem. Cytochem 49: 1473 (2001).