(2S)-1-[(2S)-2-aminopropanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide

• ChemBase ID: 106299
• Molecular Formular: C18H18F3N3O4
• Molecular Mass: 397.3484296
• Monoisotopic Mass: 397.12494073
• SMILES: C[C@H](N)C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: O=C([C@@H]1CCCN1C(=O)[C@@H](N)C)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• InChI: InChI=1S/C18H18F3N3O4/c1-9(22)17(27)24-6-2-3-13(24)16(26)23-10-4-5-11-12(18(19,20)21)8-15(25)28-14(11)7-10/h4-5,7-9,13H,2-3,6,22H2,1H3,(H,23,26)/t9-,13-/m0/s1
• InChIKey: GGRRKBLWOMKWNS-ZANVPECISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-aminopropanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2S)-2-aminopropanoyl]-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pyrrolidine-2-carboxamide
• Synonyms: Ala-Pro-AFC; AP-AFC; Ala-Pro-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105387
• PubChem CID: 25108520

CALCULATED PROPERTIES

• Acid pKa: 12.781174
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3847843
• LogD (pH = 7.4): 0.30476585
• Log P: 1.0656726
• Molar Refractivity: 94.4662 cm^3
• Polarizability: 34.905426 Å^3
• Polar Surface Area: 101.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AFC042

A fluorogenic substrate for DPP-IV.

REFERENCES

• Loch, N. et al., Eur. J. Biochem., 210:161 (1992).
• Smith, R.E. et al., Histochem. J., 24:637 (1992).