1.1.1.34: hydroxymethylglutaryl-CoA reductase (NADPH)

This is an abbreviated version, for detailed information about hydroxymethylglutaryl-CoA reductase (NADPH), go to the full flat file.

Reaction

(R)-mevalonate
+
CoA
+ 2 NADP+ =
(S)-3-hydroxy-3-methylglutaryl-CoA
+ 2 NADPH + 2 H+

Synonyms

3-hydroxy-3-methyl-glutaryl CoA reductase, 3-hydroxy-3-methylglutaryl Ccoenzyme A reductase 1, 3-hydroxy-3-methylglutaryl co-enzyme A reductase, 3-hydroxy-3-methylglutaryl CoA reductase, 3-hydroxy-3-methylglutaryl coenzyme A reductase, 3-hydroxy-3-methylglutaryl coenzyme A reductase 1, 3-hydroxy-3-methylglutaryl-CoA reductase, 3-hydroxy-3-methylglutaryl-CoA reductase (NADPH), 3-hydroxy-3-methylglutaryl-coenzyme A reductase, 3-hydroxymethylglutaryl coenzyme A reductase, acetoacetyl-coenzyme A thiolase/3-hydroxy-3-methylglutaryl-coenzyme A reductase, beta-hydroxy-beta-methylglutaryl coenzyme A reductase, beta-hydroxy-beta-methylglutaryl-Co A reductase, EuHMGR, HMG CoA reductase, HMG-CoA reductase, HMG-CoA-R, HMG-CoAR, HMG1, HMG2, HMG2.2, Hmg2p, HMG3.3, HMGCoA reductase, HMGCoA reductase-mevalonate:NADP-oxidoreductase (acetylating CoA), HMGCoAR, HMGCR, HMGR, HMGR1, HMGR1S, HMGR2, hydroxy-3-methylglutoryl-Coenzyme A reductase, hydroxymethylglutaryl CoA reductase (NADPH), hydroxymethylglutaryl-coenzyme A reductase (reduced nicotinamide adenine dinucleotide phosphate), mevalonate:NADP+ oxidoreductase (acetylating CoA), microsomal HMG-CoA reductase, NADPH-hydroxymethylglutaryl-CoA reductase, S-3-hydroxy-3-methylglutaryl-CoA reductase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.34 hydroxymethylglutaryl-CoA reductase (NADPH)

Inhibitors

Inhibitors on EC 1.1.1.34 - hydroxymethylglutaryl-CoA reductase (NADPH)

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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3R,5R)-7-(1-ethyl-3-(4-fluorophenyl)-4-methyl-5-[(5-methyl-pyrazin-2-ylmethyl)-carbamoyl]-1H-pyrrol-2-yl)-3,5-dihydroxy-heptanoic acid sodium salt
-
-
(3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-4-methyl-5-phenylcarbamoyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
-
-
(3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-5-(4-methoxybenzylcarbamoyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
-
(3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-5-(4-methoxycarbonyl-benzylcarbamoyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
-
(3R,5R)-7-[3-(4-fluoro-phenyl)-1-isopropyl-5-phenylcarbamoyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
-
(3R,5R)-7-[3-(4-fluorophenyl)-1-isopropyl-4-phenyl-5-phenylcarbamoyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
-
(3R,5R)-7-[3-(4-fluorophenyl)-5-[(3-methoxybenzyl)carbamoyl]-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
(3R,5R)-7-[3-(4-fluorophenyl)-5-[[4-(methoxymethyl)benzyl]carbamoyl]-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
(3R,5R)-7-[5-(4-carboxy-benzylcarbamoyl)-ethyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid disodium salt
-
-
(3R,5R)-7-[5-benzylcarbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid
-
-
(3R,5R)-7-[5-carbamoyl-1-ethyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
-
(3R,5R)-7-[5-carbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid sodium salt
-
-
(3R,5R)-7-[5-cyano-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
-
-
(3R,5R)-7-[5-[(3-carbamoylbenzyl)carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
(3R,5R)-7-[5-[(4-cyanobenzyl)carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
(3R,5R)-7-[5-[[4-(dimethylcarbamoyl)benzyl]carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
(5S)-5-hydroxy-4-{2-[(1S,2R,4aR)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]ethyl}furan-2(5H)-one
-
22.65% inhibition of HMG-CoA reductase at 0.001 mM concentration and maximum inhibition of 78.03% at 0.1 mM, the HMG-CoA reductase inhibitor, a clerodane diterpene from ethanolic extract of Polyalthia longifolia var. pendula, is a potential lipid lowering agent, molecular docking analysis, overview
(E,3R,5S)-7-(4-(3-(4-fluorophenyl)pentan-3-yl)-2-isopropylphenyl)-3,5-dihydroxyhept-6-enoic acid
-
competitive inhibitor, shows slight inhibitory activity
(R)-3-hydroxy-3-methylglutaryl-CoA
-
competitive inhibitor
(S)-4-carboxy-3-hydroxy-3-methylbutyryl-CoA
-
competitive inhibitor
(S)-4-carboxy-3-hydroxybutyryl-CoA
-
competitive inhibitor
1,10-phenanthroline
-
-
3,3-dimethylglutaryl-CoA
-
competitive inhibitor
3-hydroxy-3-methylglutaryl-CoA
-
0.05 mM
3-Hydroxyglutaryl-CoA
-
competitive inhibitor
3-methylglutaryl-CoA
-
competitive inhibitor
4-[[([5-[(3R,5R)-6-carboxy-3,5-dihydroxyhexyl]-4-(4-fluorophenyl)-1-(1-methylethyl)-3-phenyl-1H-pyrrol-2-yl]carbonyl)amino]methyl]benzoic acid
-
-
7-[3,4-bis(4-fluorophenyl)-1-(1-methylethyl)-5-(phenylcarbamoyl)-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3,4-bis(4-fluorophenyl)-5-[(3-hydroxyphenyl)carbamoyl]-1-(1-methylethyl)-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3,4-bis(4-fluorophenyl)-5-[(3-methoxyphenyl)carbamoyl]-1-(1-methylethyl)-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-5-(phenylcarbamoyl)-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-5-(propylcarbamoyl)-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-5-[(4-sulfamoylphenyl)carbamoyl]-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-5-[(pyridin-2-ylmethyl)carbamoyl]-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-5-[[(4-methyl-1,3-thiazol-2-yl)methyl]carbamoyl]-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-5-[[(5-methyl-1H-imidazol-2-yl)methyl]carbamoyl]-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-1-(1-methylethyl)-5-[[(5-methyl-1H-pyrazol-3-yl)methyl]carbamoyl]-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-5-(methylcarbamoyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-5-[(4-hydroxyphenyl)carbamoyl]-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[3-(4-fluorophenyl)-5-[(4-methoxybenzyl)carbamoyl]-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-(benzylcarbamoyl)-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-(cyclopropylcarbamoyl)-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-(dimethylcarbamoyl)-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-(ethylcarbamoyl)-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-carbamoyl-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-ethylcarbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
-
-
7-[5-[(4-carbamoylphenyl)carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-[(4-carboxyphenyl)carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-[[(1,5-dimethyl-1H-pyrazol-3-yl)methyl]carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-[[3-(dimethylcarbamoyl)phenyl]carbamoyl]-3,4-bis(4-fluorophenyl)-1-(1-methylethyl)-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
7-[5-[[4-(dimethylcarbamoyl)phenyl]carbamoyl]-3-(4-fluorophenyl)-1-(1-methylethyl)-4-phenyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoate
-
-
8-hydroxygeraniol
-
competitive inhibition mechanism, binds at the catalytic site, docking experiments, overview
acetoacetyl-CoA
-
-
acetyl-CoA
-
-
adenosine-2'-monophospho-5'-diphosphoribose
-
competitive inhibitor for NADPH binding site
AFGYVAE
-
-
atorvastatin
brutieridin
-
i.e. hesperetin 7-(2''-alpha-rhamnosyl-6''-(3''''-hydroxy-3''''-methylglutaryl)-beta-D-glucoside), a flavonoid conjugate from bergamot fruit extract, structural analogue of statins, computational study, overview
ceramide
-
treatment with exogenous ceramides, or increasing the endogenous ceramide levels inhibits HMGCR by 6080%
cerivastatin
CoA disulfide
-
no inactivation in presence of NADPH 1 mM, or HMG-CoA 0.5 mM
CoASH
Compactin
cycloheximide
daidzein
-
isoflavone, isolated and purified from korean soybean paste, structural analysis
deoxycholate
-
-
DFGYVAE
-
-
digitonine
-
2% digitonin, 80% inhibition
EDTA
-
inhibits the subsequent reactions of the mevalonate pathway in Hevea latex
EFGYVAE
-
-
eicosapentaenoic acid
-
inhibits translation of the enzyme about 50% at 0.15 mM, downregulation, slightly increases downregulation of protein synthesis by cycloheximide
F(4-fluoro)VAE
-
HMG-CoA competitive inhibitor
FFGYVAE
-
-
FFYVAE
-
-
FG-(4-fluoro)FVAE
-
-
FGYVAE
-
-
fluvastatin
FPYVAE
-
-
FVAE
-
HMG-CoA competitive inhibitor
genistein
-
isoflavone, isolated and purified from korean soybean paste, structural analysis
GFGYVAE
-
-
GFPDGG
-
designed on the basis of the rigid peptide backbone, increases the inhibitory potency more than 300 times compared to the first isolated LPYP from soybean, overview
GFPEGG
-
HMG-CoA competitive inhibitor
GFPTGG
GLPDGG
-
NADPH and HMG-CoA competitive inhibitor
GLPEGG
-
NADPH and HMG-CoA competitive inhibitor
GLPTGG
glycitein
-
isoflavone, isolated and purified from korean soybean paste, structural analysis
Hydroxymethylglutarate
IAVE
-
HMG-CoA competitive inhibitor
IAVP
-
NADPH competitive inhibitor
IAVPGEVA
-
isolated from soybean by pepsin
IAVPTGVA
-
-
IFGYVAE
-
-
Ile-Ala-Val-Glu
-
-
Ile-Ala-Val-Pro-Gly-Glu-Val-Ala
-
-
Ile-Val-Ala-Glu
-
-
IVAE
-
HMG-CoA competitive inhibitor
Leu-Pro-Tyr-Pro
-
-
LFGYVAE
-
-
lovastatin
LPYP
-
from soybean
melitidin
-
i.e. naringenin 7-(2''-alpha-rhamnosyl-6''-(3''''-hydroxy-3''''-methylglutaryl)-beta-D-glucoside), a flavonoid conjugate from bergamot fruit extract, structural analogue of statins, computational study, overview
mevastatin
Mevinolin
-
competitive with 3-hydroxy-3-methylglutaryl-CoA
MgATP2-
myriocin
-
concomitant reduction of both HMGR activity and the sterol content by depletion of the sphingolipid pathway. At 0.01 mM myriocin decrease to ca. 55% of the HMGR activity in control plants. Myriocin-induced down-regulation of HMGR activity is exerted at the post-translational level, like the regulatory response of HMGR to enhancement or depletion of the flux through the sterol pathway
p-chloromercuribenzoate
-
1 mM, complete inhibition
p-hydroxymercuribenzoate
PFGYVAE
-
-
pravastatin
resveratrol
inhibits the cell growth as well as the activity of recombinant enzyme. Resveratrol shows antitrypanosomal activity with an IC50 value of 0.00013 mM and moderate antipromastigote activity against Leishmania major with IC50 value: 0.153 mM
rosuvastatin
SFGYVAE peptide
-
most active inhibitory peptide; shows high ability to inhibit HMGR by competitive inhibition with respect to (S)-3-hydroxy-3-methylglutaryl-CoA
simvastatin
simvastatin acid
inhibitory as lactone or in as free aid
-
simvastatin lactone
inhibitory as lactone or in as free aid
-
small heterodimer partner nuclear receptor
-
directly regulates cholesterol biosynthesis through inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase
-
SMase C
-
treatment of fibroblasts with SMase C results in a 90% inhibition of HMGCR
-
SMase D
-
treatment of fibroblasts with SMase D inhibits by 29%
-
sodium (E,3R,5S)-7-(2-(2-fluorophenyl)-4-(3-phenylpentan-3-yl)phenyl)-3,5-dihydroxy-hept-6-enoate
-
has almost no effect on the activity
sodium (E,3R,5S)-7-(2-(3-fluorophenyl)-4-(3-phenylpentan-3-yl)phenyl)-3,5-dihydroxy-hept-6-enoate
-
-
sodium (E,3R,5S)-7-(2-(4-fluorophenyl)-4-(3-phenylpentan-3-yl)phenyl)-3,5-dihydroxy-hept-6-enoate
-
shows the most potent inhibitory activity among compounds comparable with that of clinically useful mevastatin
sodium (E,3R,5S)-7-(2-phenyl-4-(3-phenylpentan-3-yl)phenyl)-3,5-dihydroxyhept-6-enoate
-
has almost no effect on the activity
sodium (E,3R,5S)-7-(4-(3-(2-fluorophenyl)pentan-3-yl)-2-isopropylphenyl)-3,5-dihydroxyhept-6-enoate
-
-
sodium (E,3R,5S)-7-(4-(3-(3-fluorophenyl)pentan-3-yl)-2-isopropylphenyl)-3,5-dihydroxyhept-6-enoate
-
-
sodium (E,3R,5S)-7-(4-(3-phenylpentan-3-yl)-2-isopropylphenyl)-3,5-dihydroxyhept-6-enoate
-
-
squalestatin
-
mutant plants, not wild-type plants, become sterile
TFGYVAE
-
-
Tyr-Ala-Val-Glu
-
-
Tyr-Val-Ala-Glu
-
-
VFGYVAE
-
-
YAVE
-
HMG-CoA competitive inhibitor
YVAE
-
HMG-CoA competitive inhibitor
additional information
-