2-oxopyrrolidine-1-carboxamide

• ChemBase ID: 179772
• Molecular Formular: C5H8N2O2
• Molecular Mass: 128.12922
• Monoisotopic Mass: 128.05857751
• SMILES: N1(C(=O)N)C(=O)CCC1
• Canonical SMILES: NC(=O)N1CCCC1=O
• InChI: InChI=1S/C5H8N2O2/c6-5(9)7-3-1-2-4(7)8/h1-3H2,(H2,6,9)
• InChIKey: XYVMBSCIEDOIJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxopyrrolidine-1-carboxamide
• IUPAC Traditional name: 2-oxopyrrolidine-1-carboxamide
• Synonyms: 1-Carbamoyl-2-pyrrolidone; 2-Oxo-1-pyrrolidinecarboxamide; Squamolone

Database IDs

• CAS Number: 40451-67-0
• PubChem SID: 164235682
• PubChem CID: 326996

CALCULATED PROPERTIES

• Acid pKa: 15.271453
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.92454654
• LogD (pH = 7.4): -0.92454654
• Log P: -0.92454654
• Molar Refractivity: 30.5005 cm^3
• Polarizability: 11.731229 Å^3
• Polar Surface Area: 63.4 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Potent inhibition of mitochondrial NADH

Product Information

• Biological Source: Constit. of Annona squamosa and Hexalobus crispiflorus (Annonaceae). Also from Asimina triloba
• Application(s): Cytostatic

REFERENCES

• Yang, T.H. et al., J. Chin. Chem. Soc. (Taipei), 1972, 19, 149; CA, 78, 16151w, (isol, uv, pmr, ms)
• Marquez, V.E. et al., J.O.C., 1980, 45, 5308, (struct, synth, ir, pmr, ms)
• Achenbach, H. et al., Annalen, 1982, 1623, (isol, cmr)
• Zhao, G.-X. et al., Phytochemistry, 1993, 33, 1065, (isol, synth)
• Sahai, M. et al., Indian J. Chem., Sect. B, 1996, 35, 510, (isol, synth, ir, pmr, cmr, ms)