Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
(+-)-2-Hydroxyglutaric acid
2-hydroxyglutarate · C02630 · α-Hydroxyglutaric Acid · alpha-hydroxyglutarate · a-Hydroxyglutaric Acid · 2,3-Dideoxypentaric Acid · DL-2-Hydroxyglutaric Acid
식별자 및 물리적 특성
| CAS No. | 2889-31-8 |
|---|---|
| 분자식 | C5H8O5 |
| 평균 분자량 | 148.11 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | -1 |
|---|---|
| 극성 표면적 | 94.8 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 4 |
| 무거운 원자 수 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 141 |
| 지질 | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105] |
| Physical Description | Solid |
| 녹는점 | 98-100 °C(Solv: ethyl acetate (141-78-6)) |
| 끓는 점 | 394.2±27.0 °C(Predicted) |
| 밀도 | 1.508±0.06 g/cm3(Predicted) |
| 저장 조건 | Store at -20°C |
| 용해도 | DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml |
| 물리적 상태 | Liquid |
| pKa(산도 계수) | 3.67±0.10(Predicted) |
| 색상 | Colorless to light yellow |
안전 및 규제
| 건강 영향 | 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. |
|---|---|
| 노출 경로 | Endogenous, Ingestion |
| 독성 요약 | 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). |
| 신호 어 | Danger |
| 유해·위험 문구 | 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H225 |
용도
용도
A potential inhibitor of glutamate carboxypeptidase.