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

• ChemBase ID: 106329
• Molecular Formular: C27H25F3N4O8
• Molecular Mass: 590.5046096
• Monoisotopic Mass: 590.16244844
• SMILES: OC(=O)CCC(=O)NCC(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: O=C(N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccccc1)CNC(=O)CNC(=O)CCC(=O)O
• InChI: InChI=1S/C27H25F3N4O8/c28-27(29,30)18-12-25(40)42-20-11-16(6-7-17(18)20)33-26(41)19(10-15-4-2-1-3-5-15)34-23(37)14-32-22(36)13-31-21(35)8-9-24(38)39/h1-7,11-12,19H,8-10,13-14H2,(H,31,35)(H,32,36)(H,33,41)(H,34,37)(H,38,39)/t19-/m0/s1
• InChIKey: RIQDWGVGHWQUPX-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105572
• PubChem CID: 25108549

CALCULATED PROPERTIES

• Acid pKa: 4.125661
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.9702818
• LogD (pH = 7.4): -2.6636703
• Log P: 0.41899532
• Molar Refractivity: 140.0428 cm^3
• Polarizability: 52.294586 Å^3
• Polar Surface Area: 180.0 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC087

A fluorogenic substrate for Cathepsin G.

REFERENCES

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