8-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-4-methoxy-4-oxobutanamido]-12H-10-oxa-5-azatetraphen-12-iminium chloride

• ChemBase ID: 106593
• Molecular Formular: C45H50ClN7O13
• Molecular Mass: 932.3706
• Monoisotopic Mass: 931.31551238
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](CC(=O)OC)NC(=O)OCc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)OC)C(=O)Nc1cc2oc3c(nc2cc1)c1c(c(=[NH2+])c3)cccc1.[Cl-]
• Canonical SMILES: COC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc1c(n2)c2ccccc2c(=[NH2+])c1)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(=O)OC)CCC(=O)OC.[Cl-]
• InChI: InChI=1S/C45H49N7O13.ClH/c1-24(2)39(52-41(56)31(17-18-36(53)61-3)49-43(58)33(22-38(55)63-5)51-45(60)64-23-25-11-7-6-8-12-25)44(59)50-32(21-37(54)62-4)42(57)47-26-15-16-30-34(19-26)65-35-20-29(46)27-13-9-10-14-28(27)40(35)48-30;/h6-16,19-20,24,31-33,39,46H,17-18,21-23H2,1-5H3,(H,47,57)(H,49,58)(H,50,59)(H,51,60)(H,52,56);1H/t31-,32-,33-,39-;/m0./s1
• InChIKey: AALZXJWZTJYCKW-GQWTYJKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-4-methoxy-4-oxobutanamido]-12H-10-oxa-5-azatetraphen-12-iminium chloride
• IUPAC Traditional name: 8-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-4-methoxy-4-oxobutanamido]-10-oxa-5-azatetraphen-12-iminium chloride
• Synonyms: Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-MAGIC RED; Z-D(OMe)E(OMe)VD(OMe)-MAGIC RED; Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-MAGIC RED

Database IDs

• PubChem SID: 162105721
• PubChem CID: 25108750

CALCULATED PROPERTIES

• Acid pKa: 11.460146
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): 0.76904
• LogD (pH = 7.4): 2.037536
• Log P: 2.1487553
• Molar Refractivity: 244.823 cm^3
• Polarizability: 89.11929 Å^3
• Polar Surface Area: 280.81 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03MR138

A fluorogenic substrate for Cathepsin K
(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).