2,5-dioxopyrrolidin-1-yl 3-acetamidopropanoate

• ChemBase ID: 159077
• Molecular Formular: C9H12N2O5
• Molecular Mass: 228.20198
• Monoisotopic Mass: 228.07462149
• SMILES: C1(=O)CCC(=O)N1OC(=O)CCNC(=O)C
• Canonical SMILES: CC(=O)NCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C9H12N2O5/c1-6(12)10-5-4-9(15)16-11-7(13)2-3-8(11)14/h2-5H2,1H3,(H,10,12)
• InChIKey: SFMZMIJBTSYLSN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-acetamidopropanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-acetamidopropanoate
• Synonyms: N-[3-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-3-oxopropyl]acetamide; N-Acetyl-β-alanine N-Hydroxysuccinimide Ester

Database IDs

• CAS Number: 154194-69-1
• PubChem SID: 162253212
• PubChem CID: 45038076

CALCULATED PROPERTIES

• Acid pKa: 15.204599
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.722031
• LogD (pH = 7.4): -1.7220309
• Log P: -1.7220309
• Molar Refractivity: 50.7004 cm^3
• Polarizability: 20.080265 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 82-84°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A168075

Intermediate in the preparation of polyamide inducers of HL-60 cellular differentiation

REFERENCES

• Dubowchik, G., et al.: Bioorg. Med. Chem. Lett., 3, 1965 (1993)