HuagongsheHuagongshe Chemistry Print Report · For research reference only
(+-)-2-Hydroxyglutaric acid
2-hydroxyglutarate · C02630 · α-Hydroxyglutaric Acid · alpha-hydroxyglutarate · a-Hydroxyglutaric Acid · 2,3-Dideoxypentaric Acid · DL-2-Hydroxyglutaric Acid
Identifiers & Physical Properties
| CAS No. | 2889-31-8 |
|---|---|
| Molecular formula | C5H8O5 |
| Average molar mass | 148.11 g/mol |
| Monoisotopic mass | 148.03717336 g/mol |
| SMILES | O=C(O)CCC(O)C(=O)O |
| InChIKey | HWXBTNAVRSUOJR-UHFFFAOYSA-N |
| PubChem CID | 43 |
| ChEMBL | CHEMBL4870693 |
| ChEBI | CHEBI:17084 |
| DTXSID | DTXSID40864360 |
Chemical & Physical Properties
| XLogP | -1 |
|---|---|
| Topological polar surface area | 94.8 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 4 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 141 |
| Lipids | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105] |
| Physical Description | Solid |
| Melting point | 98-100 °C(Solv: ethyl acetate (141-78-6)) |
| Boiling point | 394.2±27.0 °C(Predicted) |
| Density | 1.508±0.06 g/cm3(Predicted) |
| Storage conditions | Store at -20°C |
| Solubility | DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml |
| Physical state | Liquid |
| pKa (acidity coefficient) | 3.67±0.10(Predicted) |
| Color | Colorless to light yellow |
| FDA UNII | RS4M3UYS95 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H225-H319 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501 |
Safety & Regulations
| Health effects | High 2-Hydroxyglutarate levels are associated with gliomas and acute myeloid leukemia. L-2-Hydroxyglutarate can reversibly promote leukemogenesis in vitro. Chronically high levels of L-2-hydroxyglutaric acid are associated with the inborn error of metabolism called: D-2-Hydroxyglutaric Aciduria. The D form is rare, with symptoms including macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. |
|---|---|
| Exposure routes | Endogenous, Ingestion |
| Toxicity summary | 2-hydroxyglutarate is an oncometabolite. It is a competitive inhibitor of multiple α-ketoglutarate-dependent dioxygenases, including histone demethylases and the TET family of 5-methlycytosine (5mC) hydroxylases. As a result, high levels of 2-hydroxyglutarate lead to genome-wide histone and DNA methylation alterations, which in turn lead to mutations that ultimately cause cancer. High L-2-Hydroxyglutarate levels are associated with gliomas and acute myeloid leukemia. L-2-Hydroxyglutarate can reversibly promote leukemogenesis in vitro. D-2-hydroxyglutarate mediates its neurotoxicity through activation of N-methyl-D-aspartate receptors. D-2-hydroxyglutarate is structurally similar to the excitatory amino acid glutamate and stimulates neurodegeneration by mechanisms well-known for glutamate, NMDA or mitochondrial toxins (A15198). |
| Signs and Symptoms | Symptoms of chronic exposure to D-2-Hydroxyglutarate include macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness. |
| Carcinogen Classification | Not listed by IARC. Has been implicated in oncogenesis (A15091, A15090, A15088). |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07 |
| GHS hazard statements | H225-H319 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501 |
Applications & Uses
Uses
A potential inhibitor of glutamate carboxypeptidase.
Uses
2-Hydroxypentanedioic Acid is a mouse metabolite