5-(methoxycarbonyl)pyridine-2-carboxylic acid

• ChemBase ID: 40153
• Molecular Formular: C8H7NO4
• Molecular Mass: 181.14548
• Monoisotopic Mass: 181.03750771
• SMILES: c1(C(=O)OC)cnc(C(=O)O)cc1
• Canonical SMILES: COC(=O)c1ccc(nc1)C(=O)O
• InChI: InChI=1S/C8H7NO4/c1-13-8(12)5-2-3-6(7(10)11)9-4-5/h2-4H,1H3,(H,10,11)
• InChIKey: NTCKZTBRFXTYBD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(methoxycarbonyl)pyridine-2-carboxylic acid
• IUPAC Traditional name: 5-(methoxycarbonyl)pyridine-2-carboxylic acid
• Synonyms: 5-(Methoxycarbonyl)-2-pyridinecarboxylic acid; 5-(Methoxycarbonyl)picolinic acid; 5-(Methoxycarbonyl)pyridine-2-carboxylic acid; 2,5-Pyridinedicarboxylic Acid 5-Methyl Ester; 2-Carboxy-5-(methoxycarbonyl)pyridine; NSC 236641; 5-(Methoxycarbonyl)picolinic Acid

Database IDs

• CAS Number: 17874-79-2
• MDL Number: MFCD00179343
• PubChem SID: 162044916
• PubChem CID: 314992

CALCULATED PROPERTIES

• Acid pKa: 0.5498552
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.193751
• LogD (pH = 7.4): -2.5727923
• Log P: 0.80248356
• Molar Refractivity: 42.8106 cm^3
• Polarizability: 16.316387 Å^3
• Polar Surface Area: 76.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Melting Point: 180 - 182 °C; 180-182°C; 184 - 186°C
• Hydrophobicity(logP): 1.234

Safety Information

• Storage Warning: IRRITANT; Irritant
• TSCA Listed: false

Product Information

• Purity: > 95%; 95%; 95+%

DETAILS

Toronto Research Chemicals - M261640

Compound has been shown to have insulin mimetic properties.

REFERENCES

• Gaetjens, J., et al.: Chem. Eur. J., 9, 4924 (2003)