(2S)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide; trifluoroacetic acid

• ChemBase ID: 155215
• Molecular Formular: C13H14F3N3O5
• Molecular Mass: 349.2625696
• Monoisotopic Mass: 349.08855522
• SMILES: c1cc(ccc1NC(=O)[C@@H]1CCCN1)[N+](=O)[O-].C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C([C@@H]1CCCN1)Nc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C11H13N3O3.C2HF3O2/c15-11(10-2-1-7-12-10)13-8-3-5-9(6-4-8)14(16)17;3-2(4,5)1(6)7/h3-6,10,12H,1-2,7H2,(H,13,15);(H,6,7)/t10-;/m0./s1
• InChIKey: KYRVEVYREUUAKH-PPHPATTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide; trifluoroacetic acid
• Synonyms: N-(4-Nitrophenyl)pyrrolidine-2-carboxamide; P-pNA; Pro-pNA; L-Proline p-nitroanilide trifluoroacetate salt

Database IDs

• CAS Number: 108321-19-3
• MDL Number: MFCD00069671
• PubChem SID: 162249353
• PubChem CID: 71312105

CALCULATED PROPERTIES

• Acid pKa: 12.697484
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.8840466
• LogD (pH = 7.4): -0.73189837
• Log P: 1.2771447
• Molar Refractivity: 63.6663 cm^3
• Polarizability: 23.432072 Å^3
• Polar Surface Area: 86.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C11H13N3O3 · C2HF3O2

DETAILS

Sigma Aldrich - P5267

Application
Proline p-nitroanilide (P-pNA) is a colorimetric substrate for prolyl aminopeptidase (proline iminopeptidase), an enzyme that releases proline from the N-terminus of small peptides.1,2