4-(sulfanylmethyl)pyridine-2,6-dicarboxylic acid

• ChemBase ID: 172681
• Molecular Formular: C8H7NO4S
• Molecular Mass: 213.21048
• Monoisotopic Mass: 213.00957871
• SMILES: c1c(nc(cc1CS)C(=O)O)C(=O)O
• Canonical SMILES: SCc1cc(nc(c1)C(=O)O)C(=O)O
• InChI: InChI=1S/C8H7NO4S/c10-7(11)5-1-4(3-14)2-6(9-5)8(12)13/h1-2,14H,3H2,(H,10,11)(H,12,13)
• InChIKey: WSVZILXOOFJPGD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(sulfanylmethyl)pyridine-2,6-dicarboxylic acid
• IUPAC Traditional name: 4-(sulfanylmethyl)pyridine-2,6-dicarboxylic acid
• Synonyms: 4-(Mercaptomethyl)-2,6-pyridinedicarboxylic Acid; 4-MMDPA; 4-Mercaptomethyl Dipicolinic Acid

Database IDs

• CAS Number: 1040401-18-0
• PubChem SID: 164228591
• PubChem CID: 71749968

CALCULATED PROPERTIES

• Acid pKa: 3.2285593
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.4640691
• LogD (pH = 7.4): -5.340544
• Log P: 1.3264595
• Molar Refractivity: 50.514 cm^3
• Polarizability: 19.13979 Å^3
• Polar Surface Area: 87.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 219-222°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M225380

A Dipicolinic acid tag for rigid lanthanide tagging of proteins and paramagnetic NMR Spectroscopy. The tag, 4-mercaptomethyl-dipicolinic acid, binds lanthanide ions with nanomolar affinity, is readily attached to proteins via a disulfide bond, and avoids

REFERENCES

• Ikegami, T., et al.: J. Biomol. NMR, 29, 339 (2004)
• Su, X., et al.: Chembiochem., 7, 1599 (2004)
• Vlasie, M., et al.: Chem.-Eur. J., 13, 1715 (2004)