13095-47-1
2-hydroxypentanedioic acid
CAS: 13095-47-1
Molecular Formula: C5H8O5
13095-47-1 - Names and Identifiers
| Name | 2-hydroxypentanedioic acid |
| Synonyms | R-2-HYDROXYGLUTARATE D--Hydroxyglutaric Acid D-2-Hydroxyglutaric acid (R)-2-Hydroxyglutaric acid 2-hydroxypentanedioic acid D-alpha-Hydroxyglutaric acid (R)-alpha-Hydroxyglutaric acid Pentanedioic acid, 2-hydroxy-, (2R)- |
| CAS | 13095-47-1 |
| EINECS | 231-158-0 |
| InChI | InChI=1/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1 |
13095-47-1 - Physico-chemical Properties
| Molecular Formula | C5H8O5 |
| Molar Mass | 148.11 |
| Density | 1.508±0.06 g/cm3(Predicted) |
| Boling Point | 394.2±27.0 °C(Predicted) |
| Flash Point | 206.4°C |
| Vapor Presure | 7.55E-08mmHg at 25°C |
| pKa | 3.67±0.10(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.519 |
| In vitro study | D-α-Hydroxyglutaric acid ((R)-2-hydroxyglutarate) accumulates in human cancers carrying neomorphic mutations in the isocitrate dehydrogenase (IDH) 1 and 2 genes. A partial inhibition of KDM7A toward both H3K9me2 and H3K27me2 peptides is observed in the presence of 50 mM D-2-HG and 100 μM α-ketoglutarate (α-KG). Addition of 300 μM α-KG is capable of reversing the inhibition of Caenorhabditis elegans KDM7A (CeKDM7A) by 50 mM D-2-HG, indicating that D-2-HG is a weak competitive inhibitor against α-KG toward the CeKDM7A demethylase. D-α-Hydroxyglutaric acid is a weak inhibitor of TET hydroxylases. In the presence of 0.1 mM of α-KG, addition of 10 mM D-α-Hydroxyglutaric acid results in a partial (33%) inhibition of TET2 and addition of 50 mM D-α-Hydroxyglutaric acid results in more inhibition (83%) of TET2. D-α-Hydroxyglutaric acid exhibits a less pronounced inhibitory effect toward TET1. |
| In vivo study | D-α-Hydroxyglutaric acid strongly inhibits glucose utilization, CO 2 production and the respiratory chain in rat cerebral cortex and human skeletal muscle, as well as in submitochondrial particles from bovine heart, suggesting an impairment of the aerobic metabolism. D-α-Hydroxyglutaric acid has also been proposed as an endogenous excitotoxic organic acid because it significantly decreased cell viability in neuronal cultures from chick embryo telencephalons and from neonatal rat hippocampus through stimulation of specific NMDA glutamate receptors. D-α-Hydroxyglutaric acid (0.01-1 mM) significantly increases chemiluminescence and thiobarbituric acid-reactive substances (TBA-RS) and decreased total antioxidant reactivity (TAR) values in the cortical supernatants in 30-day-old-rats. |
13095-47-1 - Reference Information
| Biological activity | D-α-Hydroxyglutaric acid ((R)-2-Hydroxyglutarate) is the neurometabolic disease D-2-Hydroxyglutarate The main metabolite accumulated in aciduria. D-α-Hydroxyglutaric acid is a weakly competitive antagonist of α-ketoglutaric acid (α-KG) that inhibits a variety of α-KG-dependent dioxygenases (dioxygenases) with a Ki of 10.87 mM. D-α-Hydroxyglutaric acid can increase the production of reactive oxygen species (ROS). D-α-Hydroxyglutaric acid also binds to and inhibits ATP synthase and inhibits mTOR signaling. |
| target | Ki: 10.87 mM (α-KG-dependent dioxygenases) ATP synthase mTOR Reactive oxygen species (ROS) |
Last Update：2024-04-09 21:54:55
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