3-히드록시-3-메틸글루타산
3-Hydroxy-3-methylglutaric acid
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기본 정보
- CAS
503-49-1- 표준 SMILES
CC(O)(CC(=O)O)CC(=O)O- InChIKey
NPOAOTPXWNWTSH-UHFFFAOYSA-N- 분자식
- C6H10O5
- 평균 분자량
- 162.14 g/mol
- 단동위원소 질량
- 162.05282342
개요
3-hydroxy-3-methylglutaric acid is a dicarboxylic acid that is glutaric acid in which one of the two hydrogens at position 3 is substituted by a hydroxy group, while the other is substituted by a methyl group. It has been found to accumulate in urine of patients suffering from HMG-CoA lyase (3-hydroxy-3-methylglutaryl-CoA lyase, EC 4.1.3.4) deficiency. It occurs as a plant metabolite in Crotalaria dura. It has a role as an antimetabolite, an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor, an anticholesteremic drug, a plant metabolite and a human metabolite. It is a tertiary alcohol, a dicarboxylic acid and a 3-hydroxy carboxylic acid. It is functionally related to a glutaric acid. It is a conjugate acid of a 3-hydroxy-3-methylglutarate(1-).
이름 및 식별자
- 우선 이름
- 3-Hydroxy-3-methylglutaric acid
- IUPAC
- 3-hydroxy-3-methylpentanedioic acid
- 현지명
- 3-히드록시-3-메틸글루타산
- 영어명
- 3-HYDROXY-3-METHYLGLUTARIC ACID
- 분자식
- C6H10O5
- 분자량
- 162.14
이름 및 동의어
MEGLUTOL503-49-13-Hydroxy-3-methylglutaric acid3-Hydroxy-3-methylpentanedioic acidDicrotalic acidHMGAPentanedioic acid, 3-hydroxy-3-methyl-3-hydroxy-3-methyl-glutaric acidbeta-Hydroxy-beta-methylglutaric acidMeglutolumCB 337CB-337
이름 더 보기
3-히드록시-3-메틸글루타산머글루톨3-Hydroxymethylglutaric acidlipoglutarenAKOS 91366medroglutaricacidMeglutol (Standard)
3-Hydorxy-3-methylglutaric acid3-Hydroxy-3-methylglutarateCLA99KCD53(S)-MeglutolNSC-361411beta-Hydroxy-beta-Methylglutarate(S)-3-Hydroxy-3-methylglutaric acidCHEBI:16831
데이터베이스 식별자
- CAS
503-49-1- PubChem CID
- 1662
- DTXSID
DTXSID90198304- ChEMBL
CHEMBL50444
물성
구조 계산 물성보충 중
- XLogP
- -1.2
- 극성 표면적
- 94.8 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 11
- 형식 전하
- 0
- 복잡도
- 158
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antilipidemics
Pharmaceuticals -> Statins
Melting Point105 °C
Physical DescriptionSolid
Collision Cross Section
123.66 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
135.9 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
135.9 Ų [M+Na]+
물리화학적 성질
- 녹는점
- 105 · 105-108 °C (lit.)
- 끓는 점
- 120 °C · 120 °C / 13mmHg
- 밀도
- 1.2132 · 1.2132 (rough estimate)
- 굴절률
- 1.423 · 1.4230 (estimate)
- 저장 조건
- -20 °C · -20°C
- 용해도
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 5 mg/ml; PBS (pH 7.2): 10 mg/ml
- 산도 계수 (pKa)
- 3.95 · 3.95±0.10(Predicted)
- 물리적 상태
- powder to crystal
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
유해성 정보
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
독성 정보
Health EffectsChronically high levels of 3-hydroxymethylglutaric acid are associated with the inborn error of metabolism: 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
안전 데이터
- wgk
- 2
- rtecs
- MA3753000
- 독성
- LD50 in mice (g/kg): 7.33 orally; 3.23 i.p. (Savoie, Lupien)
- HS 번호
- 29181990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- F 고인화성물질
- 10
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
MeSH Pharmacological Classification
Substances used to lower plasma CHOLESTEROL levels.
Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Compounds that inhibit HYDROXYMETHYLGLUTARYL COA REDUCTASES. They have been shown to directly lower CHOLESTEROL synthesis.
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
용도 및 제조
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
응용 분야
개요Meglutol (β-hydroxy-β-methylglutaric acid; HMG) is a hypolipidemic agent that acts via the inhibition of cholesterol synthesis a t the stage of HMG-CoAreductase, blocking the conversion of HMG-CoA to mevalonate. This conversion is the rate-limiting step in cholesterol biosynthesis and is the point of physiological feedback control; as such, it appears to be the ideal locus of action for a hypolipidemic agent. Investigational compounds that act by this mechanism include the natural products compactin and mevinolin.
용도antihyperlipoproteinemia
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