2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

• ChemBase ID: 172481
• Molecular Formular: C6H5NO4
• Molecular Mass: 155.1082
• Monoisotopic Mass: 155.02185765
• SMILES: C1(=O)C=CC(=O)N1CC(=O)O
• Canonical SMILES: OC(=O)CN1C(=O)C=CC1=O
• InChI: InChI=1S/C6H5NO4/c8-4-1-2-5(9)7(4)3-6(10)11/h1-2H,3H2,(H,10,11)
• InChIKey: GBKPNGVKZQBPCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid
• IUPAC Traditional name: N-maleoylglycine
• Synonyms: 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-acetic Acid; N-(Carboxymethyl)maleimide; N-Maleimidoglycine; N-Maleoylglycine; NSC 266055; Maleimidoacetic Acid; 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid; 2-Maleimido acetic acid 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Database IDs

• CAS Number: 25021-08-3
• MDL Number: MFCD00457254
• PubChem SID: 164228391
• PubChem CID: 319935

CALCULATED PROPERTIES

• Acid pKa: 3.3415997
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -3.077551
• LogD (pH = 7.4): -4.3511953
• Log P: -0.93424356
• Molar Refractivity: 34.3327 cm^3
• Polarizability: 12.835224 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 113-118°C
• Hydrophobicity(logP): -0.609

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95%; 95+%; 98%

REFERENCES

• Brownlee, J., et al.: Bioorg. Chem., 34, 424 (2006)