Grundinformationen
- CAS
503-49-1- Standard-SMILES
CC(O)(CC(=O)O)CC(=O)O- InChIKey
NPOAOTPXWNWTSH-UHFFFAOYSA-N- Summenformel
- C6H10O5
- Durchschnittliche Molmasse
- 162,14 g/mol
- Monoisotopische Masse
- 162,05282342
Überblick
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-).
Namen und Bezeichner
- Bevorzugter Name
- 3-Hydroxy-3-methylglutaric acid
- IUPAC
- 3-hydroxy-3-methylpentanedioic acid
- Lokaler Name
- Meglutol
- Englischer Name
- 3-HYDROXY-3-METHYLGLUTARIC ACID
- Summenformel
- C6H10O5
- Molmasse
- 162.14
Namen und Synonyme
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
Weitere Namen anzeigen
3-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
Datenbank-Bezeichner
- CAS
503-49-1- PubChem CID
- 1662
- DTXSID
DTXSID90198304- ChEMBL
CHEMBL50444- ChEBI
CHEBI:16831- UNII
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,2
- Polarare Oberfläche (TPSA)
- 94,8 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 11
- Formalladung
- 0
- Komplexität
- 158
Experimentelle und physikochemische Eigenschaften
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]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 105 · 105-108 °C (lit.)
- Siedepunkt
- 120 °C · 120 °C / 13mmHg
- Dichte
- 1.2132 · 1.2132 (rough estimate)
- Brechungsindex
- 1.423 · 1.4230 (estimate)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxikologische Informationen
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).
Sicherheitsdaten
- F
- 10
- wgk
- 2
- hs_code
- 29181990
- RTECS-Nr.
- MA3753000
- risk_code
- 36/37/38
- Toxizität
- LD50 in mice (g/kg): 7.33 orally; 3.23 i.p. (Savoie, Lupien)
- hazard_code
- Xi
- safety_code
- 22-24/25-36-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Anwendungen
BeschreibungMeglutol (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.
Verwendenantihyperlipoproteinemia
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