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-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 60–80%
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
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
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
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
-