4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2-hydroxybenzoic acid

• ChemBase ID: 104168
• Molecular Formular: C11H7NO5
• Molecular Mass: 233.17698
• Monoisotopic Mass: 233.03242233
• SMILES: OC(=O)c1c(O)cc(cc1)N1C(=O)C=CC1=O
• Canonical SMILES: O=C1C=CC(=O)N1c1ccc(c(c1)O)C(=O)O
• InChI: InChI=1S/C11H7NO5/c13-8-5-6(1-2-7(8)11(16)17)12-9(14)3-4-10(12)15/h1-5,13H,(H,16,17)
• InChIKey: SMSVFCGGVBWUJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-2-hydroxybenzoic acid
• IUPAC Traditional name: 4-(2,5-dioxopyrrol-1-yl)-2-hydroxybenzoic acid
• Synonyms: N-(4-Carboxy-3-hydroxyphenyl)maleimide; N-(4-CARBOXY-3-HYDROXY-PHENYL)MALEIMIDE

Database IDs

• CAS Number: 19232-43-0
• MDL Number: MFCD00022571
• PubChem SID: 162091671
• PubChem CID: 4302

CALCULATED PROPERTIES

• Acid pKa: 2.73522
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.4475708
• LogD (pH = 7.4): -2.249092
• Log P: 1.2497492
• Molar Refractivity: 57.2628 cm^3
• Polarizability: 21.066133 Å^3
• Polar Surface Area: 94.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

MP Biomedicals - 02154939

Reported to be an irreversible inhibitor of LDH isoenzyme M.

REFERENCES

• Carvajal, G., et al., National Cancer Institute Monograph, 27: 111, (1967).