(2S)-1-[(2S)-2,6-diaminohexanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide

• ChemBase ID: 106294
• Molecular Formular: C21H25F3N4O4
• Molecular Mass: 454.4428096
• Monoisotopic Mass: 454.18278996
• SMILES: NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)N
• InChI: InChI=1S/C21H25F3N4O4/c22-21(23,24)14-11-18(29)32-17-10-12(6-7-13(14)17)27-19(30)16-5-3-9-28(16)20(31)15(26)4-1-2-8-25/h6-7,10-11,15-16H,1-5,8-9,25-26H2,(H,27,30)/t15-,16-/m0/s1
• InChIKey: DJHKXOMEESUITB-HOTGVXAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2,6-diaminohexanoyl]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2S)-2,6-diaminohexanoyl]-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pyrrolidine-2-carboxamide
• Synonyms: Lys-Pro-AFC; LP-AFC; Lys-Pro-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105384
• PubChem CID: 25108515

CALCULATED PROPERTIES

• Acid pKa: 12.782327
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.577931
• LogD (pH = 7.4): -2.4739742
• Log P: 0.93377197
• Molar Refractivity: 111.7784 cm^3
• Polarizability: 41.87149 Å^3
• Polar Surface Area: 127.75 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03AFC036

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).