2-(carboxyformamido)acetic acid

• ChemBase ID: 12422
• Molecular Formular: C4H5NO5
• Molecular Mass: 147.0862
• Monoisotopic Mass: 147.01677227
• SMILES: OC(=O)C(=O)NCC(=O)O
• Canonical SMILES: OC(=O)CNC(=O)C(=O)O
• InChI: InChI=1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10)
• InChIKey: BIMZLRFONYSTPT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(carboxyformamido)acetic acid
• IUPAC Traditional name: N-oxalylglycine
• Synonyms: N-Oxalylglycine; [(Carboxymethyl)amino](oxo)acetic acid; N-Oxalylglycine

Database IDs

• CAS Number: 5262-39-5
• MDL Number: MFCD00913253
• PubChem SID: 160975729
• PubChem CID: 3080614
• CHEMBL: 90852
• Chemspider ID: 2338366
• Wikipedia Title: N-Oxalylglycine

CALCULATED PROPERTIES

• Acid pKa: 2.28052
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -6.552223
• LogD (pH = 7.4): -8.307106
• Log P: -1.3690348
• Molar Refractivity: 27.2421 cm^3
• Polarizability: 10.786729 Å^3
• Polar Surface Area: 103.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: deionized water: >10 mg/mL
• Apperance: colourless crystals; solid
• Partition Coefficient: 1.232
• pKa: 2.827
• pKb: 11.170

Safety Information

• Storage Condition: desiccated
• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 98%
• Empirical Formula (Hill Notation): C4H5NO5

DETAILS

Sigma Aldrich - O9390

Biochem/physiol Actions
N-Oxalylglycine is an inhibitor of α-ketoglutarate-dependent enzymes and mimics the initial steps but does not initiate the hydroxylation process. N-Oxalylglycine has been used to inhibit Jumonji C-domain-containing histone lysine demethylases.