2-(pyridin-3-ylformamido)acetic acid

• ChemBase ID: 45903
• Molecular Formular: C8H8N2O3
• Molecular Mass: 180.16072
• Monoisotopic Mass: 180.05349213
• SMILES: C(=O)(c1cnccc1)NCC(=O)O
• Canonical SMILES: OC(=O)CNC(=O)c1cccnc1
• InChI: InChI=1S/C8H8N2O3/c11-7(12)5-10-8(13)6-2-1-3-9-4-6/h1-4H,5H2,(H,10,13)(H,11,12)
• InChIKey: ZBSGKPYXQINNGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(pyridin-3-ylformamido)acetic acid
• IUPAC Traditional name: nicotinuric acid
• Synonyms: Nicotinuric acid; [(Pyridin-3-ylcarbonyl)amino]acetic acid; Nicotinylglycine; NICOTINURIC ACID; Nicotinuric acid; N-(3-Pyridinylcarbonyl)glycine; N-Nicotinoylglycine; 2-(Nicotinylamino)acetic Acid; NSC 71273; Nicotinoylglycine; 2-[(3-Pyridinylcarbonyl)amino]acetic acid; 2-(nicotinamido)acetic acid; 2-(pyridin-3-ylformamido)acetic acid

Database IDs

• CAS Number: 583-08-4
• EC Number: 209-497-0
• MDL Number: MFCD00023578
• PubChem SID: 162050666; 24897709
• PubChem CID: 68499

CALCULATED PROPERTIES

• Acid pKa: 2.943172
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.029622
• LogD (pH = 7.4): -4.1474614
• Log P: -1.4619281
• Molar Refractivity: 43.9608 cm^3
• Polarizability: 16.567488 Å^3
• Polar Surface Area: 79.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol; Water
• Apperance: White Solid
• Melting Point: 256-258°C (dec.)
• Hydrophobicity(logP): -0.099

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%

DETAILS

MP Biomedicals - 02102448

A nicotinic acid antagonist.

Sigma Aldrich - N4751

Biochem/physiol Actions
Nicotinuric acid (NUA) is a metabolite of niacin. Measurement of NUA levels in urine is used to indicate possible elevated nicotinamide adenine dinucleotide (NAD) catabolism. NUA may be used as a reference (standard curve) in analysis of NAD and NUA catabolism.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N4751.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - N433500

A Niacin analog for therapeutic use. Antiproliferative.

REFERENCES

• Carlson, L., et al.: Life Sci., et al.: 3, 867 (1964)
• Felsted, R., et al.: J. Biol. Chem., 242, 1274 (1964)
• Mrochek, J., et al.: Clin. Chem., 22, 1821 (1964)
• Ding, R., et al.: Clin. Pharmacol. Ther., 46, 642 (1964)
• Bottorff, M., et al.: Am. J. Cardiol