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D-2-Hydroxyglutaric acid

HCID 439391
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
13095-47-1
標準SMILES
O=C(O)CC[C@@H](O)C(=O)O
InChIKey
HWXBTNAVRSUOJR-GSVOUGTGSA-N
分子式
C5H8O5
平均分子量
148.11 g/mol
単同位体質量
148.03717336

概要

(R)-2-hydroxyglutaric acid is the (R)-enantiomer of 2-hydroxyglutaric acid. It has a role as a biomarker, a human metabolite and an algal metabolite. It is a conjugate acid of a (R)-2-hydroxyglutarate(2-). It is an enantiomer of a (S)-2-hydroxyglutaric acid.

名称と識別子

優先名称
D-2-Hydroxyglutaric acid
IUPAC
(2R)-2-hydroxypentanedioic acid
英語名
2-hydroxypentanedioic acid
分子式
C5H8O5
分子量
148.11

名称と別名

13095-47-1(2R)-2-hydroxypentanedioic acidD-2-Hydroxyglutaric acidR9UK2G8Y792-Hydroxyglutaric acid, (R)-DTXSID80897218RefChem:1082844DTXCID001326609(R)-2-Hydroxypentanedioic acid(R)-2-hydroxyglutaric acid(R)-2-hydroxyglutarated-alpha-hydroxyglutaric acid
名称をさらに表示
(R)-2-ヒドロキシグルタル酸D-2-hydroxyglutarateD-α-Hydroxyglutaric AcidR-2-HYDROXYGLUTARATED--Hydroxyglutaric Acid(2R)-hydroxyglutaric acid2-hydroxypentanedioic acidD-2-Hydroxyglutaric acid D4
Pentanedioic acid, 2-hydroxy-, (2R)-(R)-HydroxyglutarateMFCD16251406D-|A-Hydroxyglutaric acid(R)-alpha-Hydroxyglutaric acidCHEMBL1614745Glutaric acid, 2-hydroxy-, D-(R)-(-)-2-Hydroxyglutaric acid

データベース識別子

CAS
13095-47-1
PubChem CID
439391
DTXSID
DTXSID80897218
ChEMBL
CHEMBL1614745
ChEBI
CHEBI:32796
UNII
R9UK2G8Y79
Nikkaji
J1.280.876C

物性

構造計算による物性

XLogP
-1
極性表面積
94.8 Ų
水素結合供与体数
3
水素結合受容体数
5
回転可能結合数
4
重原子数
10
形式電荷
0
複雑度
141

実験および物理化学的性質

Melting Point> 300 °C
Physical DescriptionSolid

物理化学的性質

沸点
394.2 · 394.2±27.0 °C(Predicted)
比重(密度)
1.508 · 1.508±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · Sealed in dry,Store in freezer, under -20°C
溶解性
30 mg/mL; · DMF: 30 mg/mL; DMSO: 30 mg/mL; Ethanol: 30 mg/mL; PBS (pH 7.2): 10 mg/mL
酸解離定数(Pka)
3.67 · 3.67±0.10(Predicted)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Health Effects · 1 件

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 RoutesEndogenous, Ingestion
Toxicity Summary · 1 件

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 SymptomsSymptoms of chronic exposure to D-2-Hydroxyglutarate include macrocephaly, cardiomyopathy, mental retardation, hypotonia, and cortical blindness.
Carcinogen ClassificationNot listed by IARC. Has been implicated in oncogenesis (A15091, A15090, A15088).

安全データ

危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H225

化学と産業

薬理情報

Metabolism/Metabolites2-hydroxyglutarate can be converted to α-ketoglutaric acid through the action of a 2-hydroxyglutarate dehydrogenase.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysThe oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria

サプライヤー18 社

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ChemeGen 中国18818260767 · [email protected]
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