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H6132

Sigma-Aldrich

DL-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt hydrate

≥90% (HPLC)

Synonim(y):
HMG-CoA
Empirical Formula (Hill Notation):
C27H42N7Na2O20P3S · xH2O
Numer CAS:
Masa cząsteczkowa:
955.62 (anhydrous basis)
Identyfikator substancji w PubChem:
NACRES:
NA.51

Poziom jakości

200

próba

≥90% (HPLC)

temp. przechowywania

−20°C

SMILES string

O.[Na+].[Na+].CC(O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n2cnc3c(N)ncnc23

InChI

1S/C27H44N7O20P3S.2Na.H2O/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34;;;/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45);;;1H2/q;2*+1;/p-2/t14-,19-,20-,21-,25-,27?;;;/m1.../s1

InChI key

QGWMCHPRNDWWMT-UAUHQYJPSA-L

Powiązane kategorie

Opis ogólny

DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) is obtained from acetyl-CoA and acetoacetyl-CoA during condensation with the help of HMG-CoA synthase.

Zastosowanie

DL-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt hydrate has been used in drug treatment to study its effect on mTORC1 regulation. It has also been used to compare the acylomes of two reactive acyl-CoA species, like HMG-CoA and glutaryl-CoA.

Opakowanie

5 mg in glass bottle
10, 25 mg in poly bottle

Działania biochem./fizjol.

DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) acts as a precursor of cholesterol synthesis. Inhibition of HMG-CoA can decrease cholesterol synthesis. This can be converted to β-hydroxybutyrate in the blood. HMG-CoA is a regulatory enzyme for cholesterol biosynthesis, it couples with LDL receptor to regulate cholesterol synthesis, once it is inhibited it would decrease cholesterol synthesis.
DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) is a substrate used to study the specificity and kinetics of the enzyme 3-hydroxyl-3-methyl-glutaryl coenzyme A (HMG-CoA) reductase. HMG-CoA is the key intermediate in the biosynthsis of terpenes and ketone bodies. Its metabolism is the target of statin drugs used to control cholesterol levels.

Kod klasy składowania

13 - Non Combustible Solids

WGK

WGK 3

Temperatura zapłonu °F

Not applicable

Temperatura zapłonu °C

Not applicable

Środki ochrony indywidualnej

Eyeshields, Gloves, type N95 (US)

Certyfikat analizy

Świadectwo pochodzenia

Yoshiko Mizuno et al.
Journal of atherosclerosis and thrombosis, 18(5), 351-358 (2011-03-24)
Atherosclerosis is a progressive disease causally associated with multiple cardiovascular risk factors, including dyslipidemia. Without effective intervention, atherosclerosis becomes evidenced clinically as coronary artery and cerebrovascular disease, both of which remain the leading causes of death worldwide. Multiple lines of
Anti-Inflammatory Treatment
Coronary Artery Disease, 237-271 (2018)
Leucine Signals to mTORC1 via Its Metabolite Acetyl-Coenzyme A
Son SM, et al.
Cell Metabolism, 29(1), 192-201 (2019)
Sarah Statt et al.
American journal of respiratory cell and molecular biology, 53(5), 689-702 (2015-04-16)
Statins are widely used to prevent cardiovascular disease. In addition to their inhibitory effects on cholesterol synthesis, statins have beneficial effects in patients with sepsis and pneumonia, although molecular mechanisms have mostly remained unclear. Using human airway epithelial cells as
Rajakrishnan Veluthakal et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 39(6), 2110-2120 (2016-11-02)
At least 300 prenylated proteins are identified in the human genome; the majority of which partake in a variety of cellular processes including growth, differentiation, cytoskeletal organization/dynamics and vesicle trafficking. Aberrant prenylation of proteins is implicated in human pathologies including

Produkty

Dietary Terpenes

Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.

Cholesterol Biosynthesis

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

Antilipemic Agents

Randomized controlled clinical studies have suggested 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors (statins) are effective in both primary and secondary prevention of cardiovascular disease (CVD) events.

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