D-α-Hydroxyglutaric acid

• Description :

  D-α-Hydroxyglutaric acid ((R) -2-Hydroxyglutarate) is the principal metabolite accumulating in neurometabolic disease D-2-hydroxyglutaric aciduria. D-α-Hydroxyglutaric acid is a weak competitive antagonist of α-ketoglutarate (α-KG) and inhibits multiple α-KG-dependent dioxygenases with a Ki of 10.87 mM. D-α-Hydroxyglutaric acid increases reactive oxygen species (ROS) production. D-α-Hydroxyglutaric acid binds and inhibits ATP synthase and inhibits mTOR signaling[1][2][3][4][5].

• Product Name Alternative :

  (R) -2-Hydroxyglutarate; (R) -2-Hydroxyglutaric acid; (R) -2-Hydroxypentanedioic acid

• UNSPSC :

  12352211

• Hazard Statement :

  H302, H312, H332

• Target :

  ATP Synthase; Endogenous Metabolite; mTOR; Reactive Oxygen Species (ROS)

• Type :

  Natural Products

• Related Pathways :

  Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; NF-κB; PI3K/Akt/mTOR

• Applications :

  COVID-19-immunoregulation

• Field of Research :

  Cancer; Inflammation/Immunology; Neurological Disease

• Assay Protocol :

  https://www.medchemexpress.com/d-α-hydroxyglutaric-acid.html

• Purity :

  98.0

• Solubility :

  DMSO : 100 mg/mL|H2O : 200 mg/mL (ultrasonic)

• Smiles :

  O=C(O)[C@H](O)CCC(O)=O

• Molecular Formula :

  C5H8O5

• Molecular Weight :

  148.11

• Precautions :

  H302, H312, H332

• References & Citations :

  [1]Xu W, et al. Oncometabolite 2-hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases. Cancer Cell. 2011 Jan 18;19 (1) :17-30.|[2]Fu X, et al. 2-Hydroxyglutarate Inhibits ATP Synthase and mTOR Signaling. Cell Metab. 2015 Sep 1;22 (3) :508-15.|[3]Martijn Kranendijk, et al. Progress in understanding 2-hydroxyglutaric acidurias. J Inherit Metab Dis. 2012 Jul;35 (4) :571-87.|[4]Martin Böttcher, et al. D-2-hydroxyglutarate interferes with HIF-1α stability skewing T-cell metabolism towards oxidative phosphorylation and impairing Th17 polarization. Oncoimmunology. 2018 Mar 26;7 (7) :e1445454.|[5]Alexandra Latini , et al. D-2-hydroxyglutaric acid induces oxidative stress in cerebral cortex of young rats. Eur J Neurosci. 2003 May;17 (10) :2017-22.

• Shipping Conditions :

  Room Temperature

• Storage Conditions :

  -20°C, 3 years; 4°C, 2 years (Powder)

• Scientific Category :

  Natural Products

• Clinical Information :

  No Development Reported

• Isoform :

  Human Endogenous Metabolite; Microbial Metabolite

• Citation 01 :

  Research Square Preprint. 2024 Apr 19.|Biosensors (Basel) . 2022 Jan 25;12 (2) :66.|Research Square Preprint. 2024 Mar 20.

• CAS Number :

  [13095-47-1]