(2S)-1-[(2S)-2-amino-3-phenylpropanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide

• ChemBase ID: 106295
• Molecular Formular: C24H22F3N3O4
• Molecular Mass: 473.4443896
• Monoisotopic Mass: 473.15624086
• SMILES: N[C@@H](Cc1ccccc1)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](Cc1ccccc1)N)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• InChI: InChI=1S/C24H22F3N3O4/c25-24(26,27)17-13-21(31)34-20-12-15(8-9-16(17)20)29-22(32)19-7-4-10-30(19)23(33)18(28)11-14-5-2-1-3-6-14/h1-3,5-6,8-9,12-13,18-19H,4,7,10-11,28H2,(H,29,32)/t18-,19-/m0/s1
• InChIKey: KNTZFANRJMTRLY-OALUTQOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-amino-3-phenylpropanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2S)-2-amino-3-phenylpropanoyl]-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pyrrolidine-2-carboxamide
• Synonyms: Phe-Pro-AFC; FP-AFC; Phe-Pro-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105937
• PubChem CID: 25108516

CALCULATED PROPERTIES

• Acid pKa: 12.781168
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5774399
• LogD (pH = 7.4): 2.2453392
• Log P: 2.721999
• Molar Refractivity: 119.0852 cm^3
• Polarizability: 44.341644 Å^3
• Polar Surface Area: 101.73 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AFC037

A fluorogenic substrate for DPP-II and DPP-IV.

REFERENCES

• Sannes, P.L. et al., J. Histochem. and Cytochem., 34:983 (1986) (DPP-II)
• Smid, J.R. et al., Anat. Res., 233:394 (1992) (DPP-II).
• Loch, N. et al., Eur. J. Biochem., 210:161 (1992) (DPP-IV).
• Smith, R.E. et al., Histochem. J., 24:637 (1992) (DPP-IV).