3-Hydroxyhippuricacid

• CAS: 1637-75-8
• Catalog Number: ACM1637758-2
• Category: Main Products
• Molecular Weight: 195.17
• Molecular Formula: C9H9NO4
• Synonyms: N-(3-Hydroxybenzoyl-)Glycine
• IUPAC Name: 2-[(3-Hydroxybenzoyl)amino]acetic acid
• Canonical SMILES: C1=CC(=CC(=C1)O)C(=O)NCC(=O)O
• InChI: InChI=1S/C9H9NO4/c11-7-3-1-2-6(4-7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
• InChI Key: XDOFWFNMYJRHEW-UHFFFAOYSA-N
• Boiling Point: 489.8±30.0 °C
• Melting Point: 185 °C
• Flash Point: 250ºC
• Density: 1.400±0.06 g/cm³
• Solubility: Slightly soluble in chloroform, methanol
• Appearance: White to off-white solid
• Storage: Refrigerator
• Complexity: 229
• Exact Mass: 195.05315777
• Monoisotopic Mass: 195.05315777
• pKa: 3.70±0.10(Predicted)
• Topological Polar Surface Area: 86.6 Ų

Case Study

Metabolites Such as 3-Hydroxyhippuricacid May Be Used As Early Diagnostic Markers for Severe Sepsis

Liang, Qun, et al. RSC advances, 2016, 6(49), 43293-43298.

The study examined serum samples from healthy controls and severe sepsis (SS) patients who were age-matched using a UPLC-QTOF/MS-based metabolomics analysis.
· The analysis identified six unique metabolites which comprised 3-phenyllactic acid, vanillactic acid, 3-hydroxyhippuric acid, ketoleucine, 2-phenylaminoadenosine, and 3-methoxytyrosine. Three biomarkers were discovered to increase while three others decreased in SS patient serum samples.
· Among them, 3-hydroxyhippuric acid functions as an acylglycine which is commonly a minor fatty acid metabolite but its excretion can rise during various metabolic disorders. Measuring these metabolites in body fluids can aid in diagnosing conditions related to mitochondrial fatty acid beta-oxidation.
· Additionally, two serum biomarkers-3-phenyllactic acid and 3-hydroxyhippuric acid-demonstrated high accuracy, sensitivity, and specificity in differentiating AD patients from controls. ROC models achieved over 95% classification accuracy, indicating a significant difference in the serum metabolic profile of SS patients compared to normal controls. These combinations of metabolites also suggest potential predictive value for SS.

Homo sapiens Kynureninase-3-Hydroxyhippuric Acid Inhibitor Complex

Lima, Santiago, et al. Journal of medicinal chemistry, 2009, 52(2), 389-396.

This study presented the crystal structure of Homo sapiens kynureninase (HKynase) complexed with 3-hydroxyhippuric acid (5), a competitive inhibitor of the enzyme. The HKynase-5 complex provides crucial insights for designing and screening new substrate analogs and inhibitors.
· Firstly, potential hydrogen bonding partners for the ligand include the δ-oxygen of Asn-333*, the hydroxyl oxygen of Tyr-275, and the γ-oxygen of Ser-75.
· Secondly, it is essential to preserve hydrophobic interactions between the aromatic substituents of the tested ligands and the side chains of Ile-110*, Trp-305*, Phe-306*, and Phe-314*. The interactions in the HKynase-5 complex indicate a significant quadrupole molecular alignment involving the side chains of Trp-305*, Phe-314*, and the aromatic ring of 5, along with π-stacking between the ligand and the side chain of His-102*.
· Thirdly, electrostatic and hydrogen bonding interactions should be expected between ligand atoms and the guanidino nitrogens of Arg-434, as well as the imidazole nitrogen atoms of His-253.
· Lastly, the findings highlight that His-102 and Asn-333 play a key role in determining substrate specificity for 3-OH-Kyn, making the interactions between these residues and ligand atoms important for assessing binding modes in docking studies.