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D-2-Hydroxyglutaric acid

HCID 439391
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
13095-47-1
표준 SMILES
O=C(O)CC[C@@H](O)C(=O)O
InChIKey
HWXBTNAVRSUOJR-GSVOUGTGSA-N
분자식
C5H8O5
평균 분자량
148.11 g/mol
단동위원소 질량
148.03717336

개요

(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.

이름 및 식별자

우선 이름
D-2-Hydroxyglutaric acid
IUPAC
(2R)-2-hydroxypentanedioic acid
영어명
2-hydroxypentanedioic acid
분자식
C5H8O5
분자량
148.11

이름 및 동의어

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
이름 더 보기
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

데이터베이스 식별자

CAS
13095-47-1
PubChem CID
439391
DTXSID
DTXSID80897218
ChEMBL
CHEMBL1614745

물성

구조 계산 물성

XLogP
-1
극성 표면적
94.8 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
5
회전 가능 결합 수
4
무거운 원자 수
10
형식 전하
0
복잡도
141

실험 및 물리화학적 성질

Melting Point> 300 °C
Physical DescriptionSolid

물리화학적 성질

끓는 점
394.2 · 394.2±27.0 °C(Predicted)
밀도
1.508 · 1.508±0.06 g/cm3(Predicted)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
용해도
30 mg/mL; · DMF: 30 mg/mL; DMSO: 30 mg/mL; Ethanol: 30 mg/mL; PBS (pH 7.2): 10 mg/mL
산도 계수 (pKa)
3.67 · 3.67±0.10(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Health Effects · 1건

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 · 1건

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).

안전 데이터

신호 어
Danger
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H225

화학 및 산업

약리 정보

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

공급사18 곳

江苏生康迈翔科技有限公司18217475093 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
上海稳同科技有限公司02151600108 13062666369 · [email protected]
石家庄州昆医药科技有限公司0311-83784138 18633934202 · [email protected]
甘肃德通医药化学技术有限公司18993961550 18993966060 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
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