Page last updated: 2024-11-04

3-hydroxy-3-methylglutaryl-coenzyme a

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

3-hydroxy-3-methylglutaryl-coenzyme A: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-hydroxy-3-methylglutaryl-CoA : An alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(3S)-3-hydroxy-3-methylglutaryl-CoA : A 3-hydroxy-3-methylglutaryl-CoA where the 3-hydroxy-3-methylglutaryl component has (S)-configuration. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID445127
CHEMBL ID1794644
CHEBI ID15467
SCHEMBL ID1198
MeSH IDM0051584

Synonyms (32)

Synonym
gtpl3040
hmg-coenzyme a
CHEBI:15467 ,
(s)-3-hydroxy-3-methylglutaryl-coenzyme a
(3s)-3-hydroxy-3-methylglutaryl-coenzyme a
3'-phosphoadenosine 5'-{3-[(3r)-4-({3-[(2-{[(3s)-4-carboxy-3-hydroxy-3-methylbutanoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}
(3s)-3-hydroxy-3-methylglutaryl-coa
3-hydroxy-3-methylglutaryl-coenzyme a
C00356
hydroxymethylglutaroyl coenzyme a
3-hydroxy-3-methylglutaryl-coa
(s)-3-hydroxy-3-methylglutaryl-coa
hmg-coa
1553-55-5
hydroxymethylglutaryl-coa
3-HYDROXY-3-METHYL-GLUTARYL-COA ,
(3s)-5-[2-[3-[[(2r)-4-[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid
CHEMBL1794644
s-(hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme a
s-(hydrogen 3-hydroxy-3-methylglutaryl)coenzyme a
SCHEMBL1198
3s-hydroxy-3-methyl-5-carboxypentanoyl-coa
LMFA07050116
s-(hydrogen 3-hydroxy-3-methylpentanedioic acid
s-(hydrogen 3-hydroxy-3-methylpentanedioate
3-hydroxy-3-methyl-glutaryl-coenzyme a
hydroxymethylglutaryl-coenzyme a
Q307532
CABVTRNMFUVUDM-VRHQGPGLSA-N
26926-09-0
(s)-3-hydroxy-3-methylglutaryl coenzyme a
DTXSID40862689

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The most common adverse events reported after atorvastatin-headache and nausea-occurred as frequently after placebo."( Multiple-dose pharmacokinetics, pharmacodynamics, and safety of atorvastatin, an inhibitor of HMG-CoA reductase, in healthy subjects.
Cilla, DD; Gibson, DM; Posvar, EL; Sedman, AJ; Whitfield, LR, 1996
)
0.29
"Transaminase and creatine phosphokinase levels and adverse events were recorded."( An overview of the clinical safety profile of atorvastatin (lipitor), a new HMG-CoA reductase inhibitor.
Bakker-Arkema, RG; Black, DM; Nawrocki, JW, 1998
)
0.3
"Atorvastatin was well tolerated; fewer than 2% of the atorvastatin-treated patients withdrew due to drug-attributable adverse events."( An overview of the clinical safety profile of atorvastatin (lipitor), a new HMG-CoA reductase inhibitor.
Bakker-Arkema, RG; Black, DM; Nawrocki, JW, 1998
)
0.3

Pharmacokinetics

ExcerptReferenceRelevance
" Atorvastatin peak concentration and area under the plasma concentration-time curve (AUC) values increased more than proportionally with atorvastatin dose after both single and multiple drug doses."( Multiple-dose pharmacokinetics, pharmacodynamics, and safety of atorvastatin, an inhibitor of HMG-CoA reductase, in healthy subjects.
Cilla, DD; Gibson, DM; Posvar, EL; Sedman, AJ; Whitfield, LR, 1996
)
0.29
" Pharmacokinetic parameters of losartan and EXP-3174 in rats were determined after oral and intravenous administration of losartan (9 mg/kg) without and with HMG-CoA reductase inhibitors (1 mg/kg)."( Effects of HMG-CoA reductase inhibitors on the pharmacokinetics of losartan and its main metabolite EXP-3174 in rats: possible role of CYP3A4 and P-gp inhibition by HMG-CoA reductase inhibitors.
Choi, DH; Choi, JS; Yang, SH, 2011
)
0.37

Bioavailability

ExcerptReferenceRelevance
" The most prominent effects were observed after co-incubation with Ferrlecit, probably caused by an increased bioavailability of the iron gluconate complex."( Influence of Fe(II) and Fe(III) on the expression of genes related to cholesterol- and fatty acid metabolism in human vascular smooth muscle cells.
Drynda, A; Hoehn, R; Peuster, M, 2010
)
0.36
" Consequently, the absolute bioavailability (F) of losartan after oral administration with simvastatin was significantly increased by 59."( Effects of HMG-CoA reductase inhibitors on the pharmacokinetics of losartan and its main metabolite EXP-3174 in rats: possible role of CYP3A4 and P-gp inhibition by HMG-CoA reductase inhibitors.
Choi, DH; Choi, JS; Yang, SH, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
"This multicenter, double-blind, placebo-controlled study was conducted to evaluate dose-response effects and safety of once-daily administration of pravastatin, a new inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase."( Once-daily pravastatin in patients with primary hypercholesterolemia: a dose-response study.
Berkson, DM; Colfer, HT; Cressman, MD; Farmer, JA; Farnham, DJ; Jones, PH; McKenney, JM; Proctor, JD; Wolfson, PM; Wright, JT, 1991
)
0.28
" The dosage of 1-methyl-4-phenyl pyridinium (MPP+) in the striatum by high-performance liquid chromatography indicated that fenofibrate did not affect MPTP metabolism."( Lipid-lowering drugs in the MPTP mouse model of Parkinson's disease: fenofibrate has a neuroprotective effect, whereas bezafibrate and HMG-CoA reductase inhibitors do not.
Bordet, R; Destée, A; Gelé, P; Kreisler, A; Lhermitte, M; Wiart, JF, 2007
)
0.34
" Sinapic acid was administered to rats orally at a dosage of 40 mg/kg everyday for a period of 4 weeks."( Prevention of cardiac dysfunction, kidney fibrosis and lipid metabolic alterations in l-NAME hypertensive rats by sinapic acid--Role of HMG-CoA reductase.
Chatterjee, S; Manivannan, J; Raja, B; Silambarasan, T, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
3-hydroxy-3-methylglutaryl-CoAAn alpha,omega dicarboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of 3-hydroxy-3-methylglutaric acid.
3-hydroxy fatty acyl-CoAA hydroxy fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any 3-hydroxy fatty acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (28)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Ketone body metabolism1019
Synthesis of Ketone Bodies817
Butanoate metabolism ( Butanoate metabolism )1518
(S)-3-Hydroxy-3-methyl-glutaryl-CoA = Acetyl-CoA + Acetoacetic acid ( Valine,Leucine and Isoleucine degradation )13
Steroids metabolism ( Steroids metabolism )1627
Valine,Leucine and Isoleucine degradation ( Valine,Leucine and Isoleucine degradation )2936
(S)-3-Hydroxy-3-methyl-glutaryl-CoA = 3-Methyl-glutaconyl-CoA + H2O ( Valine,Leucine and Isoleucine degradation )13
Cholesterol metabolism with Bloch and Kandutsch-Russell pathways039
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
Disorders in ketolysis58
Cholesterol synthesis disorders015
Metabolic reprogramming in pancreatic cancer4223
Mevalonate pathway010
Cholesterol metabolism214
Enterocyte cholesterol metabolism111
Ergosterol biosynthesis332
superpathway of sterol biosynthesis050
leucine degradation I020
Valine, leucine and isoleucine degradation034
Cholesterol biosynthesis pathway02
Metabolism overview078
Biochemical pathways: part I0466
Amino acid metabolism094
Statin inhibition of cholesterol production04
Ferroptosis133
Cerebral organic acidurias, including diseases527

Bioassays (6)

Assay IDTitleYearJournalArticle
AID613058Activity of Streptococcus pneumoniae recombinant HMGR class II expressed in Escherichia coli BL21(DE3) using HMG-CoA substrate after 1 min by microplate reader2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Specific inhibitions of annonaceous acetogenins on class II 3-hydroxy-3-methylglutaryl coenzyme A reductase from Streptococcus pneumoniae.
AID613062Activity of syrian hamsters HMGR class I expressed in Escherichia coli BL21(DE3) using HMG-CoA substrate after 1 min by microplate reader2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Specific inhibitions of annonaceous acetogenins on class II 3-hydroxy-3-methylglutaryl coenzyme A reductase from Streptococcus pneumoniae.
AID613061Activity of Haloferax volcanii HMGR class I expressed in Escherichia coli BL21(DE3) using HMG-CoA substrate after 1 min by microplate reader2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Specific inhibitions of annonaceous acetogenins on class II 3-hydroxy-3-methylglutaryl coenzyme A reductase from Streptococcus pneumoniae.
AID613059Activity of Listeria monocytogenes HMGR class II expressed in Escherichia coli BL21(DE3) using HMG-CoA substrate after 1 min by microplate reader2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Specific inhibitions of annonaceous acetogenins on class II 3-hydroxy-3-methylglutaryl coenzyme A reductase from Streptococcus pneumoniae.
AID613060Activity of Staphylococcus aureus HMGR class II expressed in Escherichia coli BL21(DE3) using HMG-CoA substrate after 1 min by microplate reader2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Specific inhibitions of annonaceous acetogenins on class II 3-hydroxy-3-methylglutaryl coenzyme A reductase from Streptococcus pneumoniae.
AID1346866Human hydroxymethylglutaryl-CoA synthase 1 (Lanosterol biosynthesis pathway)2010Analytical biochemistry, Jan-01, Volume: 396, Issue:1
A visible wavelength spectrophotometric assay suitable for high-throughput screening of 3-hydroxy-3-methylglutaryl-CoA synthase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (400)

TimeframeStudies, This Drug (%)All Drugs %
pre-199033 (8.25)18.7374
1990's82 (20.50)18.2507
2000's91 (22.75)29.6817
2010's159 (39.75)24.3611
2020's35 (8.75)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (2.94%)5.53%
Reviews47 (11.52%)6.00%
Case Studies7 (1.72%)4.05%
Observational0 (0.00%)0.25%
Other342 (83.82%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]