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

• ChemBase ID: 106425
• Molecular Formular: C27H28N4O8
• Molecular Mass: 536.53322
• Monoisotopic Mass: 536.19071388
• SMILES: Cc1cc(=O)oc2c1ccc(NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)CCC(=O)O)c2
• Canonical SMILES: O=C(N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)Cc1ccccc1)CNC(=O)CNC(=O)CCC(=O)O
• InChI: InChI=1S/C27H28N4O8/c1-16-11-26(37)39-21-13-18(7-8-19(16)21)30-27(38)20(12-17-5-3-2-4-6-17)31-24(34)15-29-23(33)14-28-22(32)9-10-25(35)36/h2-8,11,13,20H,9-10,12,14-15H2,1H3,(H,28,32)(H,29,33)(H,30,38)(H,31,34)(H,35,36)/t20-/m0/s1
• InChIKey: WFUPIIDEBOLNTM-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({[({[(1S)-1-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]-2-phenylethyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)propanoic acid
• IUPAC Traditional name: 3-({[({[(1S)-1-[(4-methyl-2-oxochromen-7-yl)carbamoyl]-2-phenylethyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)propanoic acid
• Synonyms: Suc-Gly-Gly-Phe-AMC; Suc-GGF-AMC; Suc-Gly-Gly-Phe-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105451
• PubChem CID: 25108615

CALCULATED PROPERTIES

• Acid pKa: 4.125661
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.3347087
• LogD (pH = 7.4): -3.0280802
• Log P: 0.054568227
• Molar Refractivity: 139.1103 cm^3
• Polarizability: 52.85465 Å^3
• Polar Surface Area: 180.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC087

A fluorogenic substrate for Cathepsin G.

REFERENCES

• Lively, M.O. et al., Biochimet. Biophys. Acta., 525:171 (1978).
• Yoshida, N. et al., Biochem., 19:5799 (1980).