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

• ChemBase ID: 104578
• Molecular Formular: C15H14N2O2
• Molecular Mass: 254.28386
• Monoisotopic Mass: 254.1055277
• SMILES: O=C1CC[C@H](N1)C(=O)Nc1cc2c(cccc2)cc1
• Canonical SMILES: O=C1CC[C@H](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)/t13-/m0/s1
• InChIKey: BZEPQNMASTUAMY-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-(naphthalen-2-yl)-5-oxopyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-N-(naphthalen-2-yl)-5-oxopyrrolidine-2-carboxamide
• Synonyms: L-Pyroglutamic acid β-naphthylamide; L-Pyrrolidonyl-β-naphthylamide; N1-(2-Naphthyl)-L-pyroglutamic acid; PYR; L-Pyroglutamic acid 2-naphthylamide; L-Pyrrolidonyl-β-naphthylamide; L-PYROGLUTAMIC ACID β-NAPHTHYLAMIDE

Database IDs

• CAS Number: 22155-91-5
• EC Number: 244-809-9
• MDL Number: MFCD00055911
• Beilstein Number: 5066652
• PubChem SID: 162092266
• PubChem CID: 6950551

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

• Melting Point: 187-189°C

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (TLC)

DETAILS

MP Biomedicals - 02156463

A substrate for pyroglutamate aminopeptidase.

Sigma Aldrich - P5891

Application
A substrate for pyroglutamate aminopeptidase.1 Used for differentiation of Group A streptococci and enterococci from other streptococci.2

REFERENCES

• Szewczuk, A. and Mulcyzk, M., Eur. J. Biochem. , 8 : 63 (1969).