N-[(5-Hydroxy-3-pyridinyl)carbonyl]-L-glutamic acid
[CAS# 112193-35-8]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glutamic acid derivative
• Name: N-[(5-Hydroxy-3-pyridinyl)carbonyl]-L-glutamic acid
• Synonyms: Nooglutil; Nooglutyl; ONK 10
• Molecular Formula: C₁₁H₁₂N₂O₆
• Molecular Weight: 268.22
• Protein Sequence: v
• CAS Registry Number: 112193-35-8
• SMILES: C1=C(C=NC=C1O)C(=O)N[C@@H](CCC(=O)O)C(=O)O

Properties

• Solubility: Freely soluble (160 g/L) (25 °C), Calc.^*
• Density: 1.514±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 704.7±60.0 °C 760 mmHg (Calc.)^*
• Flash point: 380.0±32.9 °C (Calc.)^*
• Index of refraction: 1.611 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

N-[(5-Hydroxy-3-pyridinyl)carbonyl]-L-glutamic acid, more commonly known as picolinic acid conjugated L-glutamic acid or 5-hydroxy-3-pyridinecarboxylic acid-L-glutamate, is a synthetic or semisynthetic derivative designed to integrate key biological motifs: a pyridine-based aromatic ring with a hydroxyl group and the amino acid L-glutamic acid. The molecule is structurally analogous to natural compounds found in mammalian and microbial metabolism, and it has potential as a building block in biochemical research, drug design, and diagnostics.

The core structure of this compound combines a hydroxy-substituted pyridine ring—a common motif in bioactive molecules—with L-glutamic acid, a critical neurotransmitter and metabolic intermediate. The presence of a hydroxy group on the pyridine ring increases the hydrophilicity and potential for hydrogen bonding, while the carboxamide linkage to glutamic acid allows for incorporation into peptide chains or metabolic pathways. This makes the compound relevant to studies on molecular recognition, enzyme-substrate interactions, and potential pharmaceutical applications.

Though not a naturally occurring metabolite, N-[(5-Hydroxy-3-pyridinyl)carbonyl]-L-glutamic acid can serve as a functional analog in the development of enzyme inhibitors or drug delivery systems. Pyridine-containing ligands are well known to interact with metal centers and biological macromolecules, and the glutamate moiety can facilitate cellular uptake or receptor-specific targeting. For example, derivatives of picolinic acid have been investigated for their role in metal ion transport and immune modulation, while glutamic acid analogs have long been used in targeting cancer cells due to their high expression of glutamate transporters.

Moreover, such a hybrid structure may be studied in the context of synthetic bioconjugates for use in radiolabeling or fluorescent tagging, especially when linked to diagnostic markers or therapeutic agents. The molecule’s amphiphilic nature also allows for incorporation into polymeric systems or liposomes.

No direct biological or pharmaceutical product currently features this exact compound, but its closely related structures, such as picolinic acid derivatives and glutamate conjugates, are being actively investigated for applications in neurobiology, oncology, and metal chelation therapies.

References

Kiselev AV, Vedenkin AS, Stovbun IS, Sergienko VI, Kalinina TS (2019) Calcium salt of N-(5-hydroxynicotinoyl)-L-glutamic acid weakens depressive-like behavior and Parkinsonian syndrome in experiment on rodents. Bulletin of Experimental Biology and Medicine 167 2 215–218 DOI: 10.1007/s10517-019-04643-5

Kiselev AV, Machula AA, Efimov SI, Pashkova EB, Stovbun SV (2019) A new synthesis of calcium N-(5-hydroxynicotinoyl)-L-glutamate and its X-ray diffraction structure. Russian Journal of Organic Chemistry 55 5 768–772 DOI: 10.1134/S1070428019050063

Kopelevich VM, Gunar VI (1999) Some approaches to the directed search for new drugs based on nicotinic acid. Pharmaceutical Chemistry Journal 33 4 194–197 DOI: 10.1007/BF02509934