(2S)-2-(2-aminoacetamido)-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-3-phenylpropanamide

• ChemBase ID: 106291
• Molecular Formular: C21H18F3N3O4
• Molecular Mass: 433.3805296
• Monoisotopic Mass: 433.12494073
• SMILES: NCC(=O)N[C@@H](Cc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCC(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccccc1
• InChI: InChI=1S/C21H18F3N3O4/c22-21(23,24)15-10-19(29)31-17-9-13(6-7-14(15)17)26-20(30)16(27-18(28)11-25)8-12-4-2-1-3-5-12/h1-7,9-10,16H,8,11,25H2,(H,26,30)(H,27,28)/t16-/m0/s1
• InChIKey: NHUKEOWPMJKWGH-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-aminoacetamido)-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-3-phenylpropanamide
• IUPAC Traditional name: (2S)-2-(2-aminoacetamido)-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]-3-phenylpropanamide
• Synonyms: Gly-Phe-AFC; GF-AFC; Gly-Phe-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105935
• PubChem CID: 24753988

CALCULATED PROPERTIES

• Acid pKa: 11.484978
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.38011587
• LogD (pH = 7.4): 1.308072
• Log P: 1.8805692
• Molar Refractivity: 106.9022 cm^3
• Polarizability: 39.58552 Å^3
• Polar Surface Area: 110.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AFC033

A fluorogenic substrate for Cathepsin C (DPP-I).

REFERENCES

• Smith, M.J. et al., J. Imm., 154:6299 (1995).