3-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid

• ChemBase ID: 106434
• Molecular Formular: C29H33N3O8
• Molecular Mass: 551.58762
• Monoisotopic Mass: 551.22676503
• SMILES: CC(C)C[C@H](NC(=O)CCC(=O)O)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccc(cc1)O)NC(=O)CCC(=O)O)C
• InChI: InChI=1S/C29H33N3O8/c1-16(2)12-22(31-25(34)10-11-26(35)36)29(39)32-23(14-18-4-7-20(33)8-5-18)28(38)30-19-6-9-21-17(3)13-27(37)40-24(21)15-19/h4-9,13,15-16,22-23,33H,10-12,14H2,1-3H3,(H,30,38)(H,31,34)(H,32,39)(H,35,36)/t22-,23-/m0/s1
• InChIKey: RIYLNECMTVNMSO-GOTSBHOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]ethyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid
• Synonyms: Suc-Leu-Tyr-AMC; Suc-LY-AMC; Suc-Leu-Tyr-7-Amino-4-Methylcoumarin

Database IDs

• CAS Number: 94367-20-1
• PubChem SID: 162087319
• PubChem CID: 25108624

CALCULATED PROPERTIES

• Acid pKa: 4.3265214
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.4793577
• LogD (pH = 7.4): -0.26776293
• Log P: 2.6791606
• Molar Refractivity: 146.4552 cm^3
• Polarizability: 55.885635 Å^3
• Polar Surface Area: 171.13 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC117

A fluorogenic substrate for the quantitative determination of Calpain Isozymes I, Calpain Isozymes II and E. Coli Protease Ti. Also suitable for measuring the peptidase activity of the 20S proteasome. Typical concentrations range from 10 - 100 μM, depending on assay conditions. PROTECT FROM LIGHT. PROTECT FROM MOISTURE.
Excitation max.: ~380 nm
Emission max.: ~460 nm

REFERENCES

• Sasaki, T. et al., J. Biol. Chem., 259:12489 (1984).
• Woo, K.M. et al., J. Biol. Chem., 264:2088 (1989).
• Seol, J.H., et al. 1989. FEBS Lett. 247, 197.