N-(naphthalen-2-yl)-5-oxopyrrolidine-2-carboxamide

• ChemBase ID: 129203
• Molecular Formular: C15H14N2O2
• Molecular Mass: 254.28386
• Monoisotopic Mass: 254.1055277
• SMILES: O=C(Nc1cc2ccccc2cc1)C1NC(=O)CC1
• Canonical SMILES: O=C1CCC(N1)C(=O)Nc1ccc2c(c1)cccc2
• InChI: InChI=1S/C15H14N2O2/c18-14-8-7-13(17-14)15(19)16-12-6-5-10-3-1-2-4-11(10)9-12/h1-6,9,13H,7-8H2,(H,16,19)(H,17,18)
• InChIKey: BZEPQNMASTUAMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(naphthalen-2-yl)-5-oxopyrrolidine-2-carboxamide
• IUPAC Traditional name: pyrrolidonyl-β-naphthylamide
• Synonyms: Pyrrolidonyl-beta-naphthylamide; (S)-N-(2-Naphthyl)-5-oxopyrrolidine-2-carboxamide; L-Pyrrolidonecarboxy-β-naphthylamide; L-Pyroglutamic Acid β-Naphthylamide

Database IDs

• CAS Number: 22155-91-5
• PubChem SID: 162223500
• PubChem CID: 90745
• Chemspider ID: 81932
• Wikipedia Title: Pyrrolidonyl-beta-naphthylamide

CALCULATED PROPERTIES

• Acid pKa: 11.574959
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.5341086
• LogD (pH = 7.4): 1.5340832
• Log P: 1.534109
• Molar Refractivity: 72.8153 cm^3
• Polarizability: 28.718498 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol (200mg/4ml)
• Apperance: Off-White Solid
• Melting Point: 184-185°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P997500

A substrate for pyroglutamate aminopeptidase. Used for colorimetric determination of pyrrolidonyl peptidase activity in bacteria.

REFERENCES

• Szewczuk, A., et al.: Eur. J. Biochem., 8, 63 (1969)
• Szewczuk, A., et al.: Anal. Biochem., 39, 268 (1971)