1.1.1.239: 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

This is an abbreviated version, for detailed information about 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+), go to the full flat file.

Reaction

testosterone
+
NAD+
=
androstenedione
+
NADH
+
H+

Synonyms

17-ketoreductase, 17beta-HSD, 17beta-hydroxysteroid dehydrogenase type 5, 3alpha(17beta)-HSD, 3alpha(17beta)-hydroxysteroid dehydrogenase, AKR1C26, AKR1C27, AKR1C28, AKR1C3, AKR1C34, aldo-keto reductase 1C3, dehydrogenase, 3alpha,17beta-hydroxy steroid, More, NAD+-dependent 3alpha(17beta)-hydroxysteroid dehydrogenase, NAD+-dependent 3beta(17beta)-hydroxysteroid dehydrogenase, NAD+-linked S-tetralol dehydrogenase, PGER6, type 2 3alpha-HSD, type 2 3alpha-hxdroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase, type 2 3alppha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase, type 3 17beta-hydroxysteroid dehydrogenase, type 5 17beta-HSD, type 5 17beta-hydroxysteroid dehydrogenase, type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase, type 5 beta-hydroxysteroid dehydrogenase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.239 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

Inhibitors

Inhibitors on EC 1.1.1.239 - 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E)-3-(3,3-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)prop-2-enoate
-
-
(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
93.3% inhibition at 0.1 mM
(2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
89.1% inhibition at 0.1 mM
(2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
92.7% inhibition at 0.1 mM
(2E)-3-prop-2-enoic acid
-
-
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoic acid
-
i.e. baccharin, a component of Brazilian propolis, exhibits a high inhibitory potency and selectivity for AKR1C3 over other AKR1C isoforms. When the cinnamic acid group of baccharin is esterified, there is a dramatic decrease in potency and selectivity for AKR1C3 in comparison to baccharin. Low or submicromolar inhibition is observed when the 3-prenyl group of baccharin is removed, and the selectivity over AKR1C2 is low. Inhibition of NAD+ dependent oxidation of S-tetralol
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
-
-
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
-
-
(2E)-3-[4-(benzoyloxy)phenyl]prop-2-enoic acid
-
-
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
93.5% inhibition at 0.1 mM
(2E)-3-[4-(pyridine-4-carbonyloxy)phenyl]prop-2-enoic acid
-
-
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
-
37% inhibition at 0.010 mM
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
-
-
(E)-3-(3-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
-
-
(Z/E)-3-(4-((3-phenylpropanoyl)oxy)phenyl)acrylic acid
-
-
(Z/E)-tert-butyl 3-(4-(3-phenylpropanoyloxy)phenyl)acrylate
-
-
1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
-
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 11 nM
1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
-
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 22 nM
1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
-
IC50 value in HCT-116 cells engineered to over-express AKR1C3 is 24 nM
17alpha-methyltestosterone
-
competitive inhibition
17beta-estradiol
-
0.175 mM, 25-40% inhibition of testosterone oxidation
2'-des-methyl-indomethacin
-
the cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
-
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
-
inhibitor is about 1000times more selective for isoform AKR1C3 over AKR1C2, and selectivity is even higher when compared with AKR1C1 and AKR1C4
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
-
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
-
-
21-hydroxypregn-4-ene-3,20-dione
-
0.010 mM, 73% inhibition
3-((4-nitronaphthalen-1-yl)amino)benzoic acid
-
inhibitor nanomolar potency and selective inhibition of isoform AKR1C3 but also acts as an androgen receptor antagonist. It inhibits 5alpha-dihydrotestosterone stimulated androgen receptor reporter gene activity with an IC50 value of 4.7 microM and produces a concentration dependent reduction in androgen receptor levels in prostate cancer cells
3-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)benzoic acids
-
-
-
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
-
-
3-(phenylamino)benzoic acid
-
-
-
3-phenoxybenzoic acid
-
inhibitor carboxylic acid binds to the oxyanion site, in which the carboxylate group very closely overlays the acetate molecule found in other AKR1C3 structures and forms hydrogen bonds to the enzyme catalytic residues His117 and Tyr55, as well as to a conserved water network located in and near the SP3 subpocket. The 3-phenoxy ring extends into the SP1 subpocket and makes van der Waals contacts with the aromatic residues Phe306, Phe311 and Tyr319 that line the pocket
3-[(4-nitrophenyl)amino]benzoic acid
-
94fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(5-chlorothiophene-2-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
-
-
3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
-
360fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
-
inhibitor shows 17fold and 30fold selectivity against isoforms AKR1C2 and AKR1C1, respectively, and much higher selectivity against AKR1C4
3beta-cyclohexylethyl-androsterone
-
potent inhibitor
3beta-n-hexyl-androsterone
-
potent inhibitor
3beta-phenylethyl-androsterone
-
potent inhibitor
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
-
-
5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
-
5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
-
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
-
-
5alpha-Androstan-3beta-ol-17-one
-
0.005 mM, 55% inhibition
5alpha-pregnan-3beta-ol-20-one
-
0.005 mM, 52% inhibition
5beta-androstan-3,17-dione
-
product inhibition, forward reaction
5beta-androstan-3beta-ol-17-one
-
0.005 mM, 87% inhibition
5beta-dihydrotestosterone
-
product inhibition, reverse reaction
5beta-Pregnan-3beta-ol-20-one
-
0.005 mM, 81% inhibition
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
-
7-hydroxyflavone
-
0.007 mM, 50% inhibition, oxidation of androstandiol
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
-
-
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
-
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
-
-
abietic acid
-
0.010 mM, 50% inhibition, oxidation of androstandiol
Ag+
-
0.1 mM, complete inhibition
androstendione
-
-
baccharin
-
-
-
biochain A
-
0.014 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.008 mM, oxidation of androstanediol
chrysin
-
0.010 mM, 50% inhibition, oxidation of androstandiol
Cibacron blue
-
-
coumestrol
-
0.005 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.011 mM, 50% inhibition, oxidation of androstanediol
CuCl2
-
1 mM, complete inhibition
dexamethasone
-
0.10 mM, 39% inhibition
Dienstrol
-
0.010 mM, 60% inhibition
FeCl3
-
10 mM, 46% inhibition
ferulic acid
-
-
Hexestrol
Hexoestrol
Hg2+
-
0.1 mM, complete inhibition
hinokitiol
ikarisoside A
competitive; competitive
-
indomethacin
kaempferol
m-coumaric acid
-
-
Medroxyprogesterone acetate
-
0.010 mM, 22% inhibition
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
-
-
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
-
-
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
-
-
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
-
-
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
-
-
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
-
-
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
N-(4-chlorobenzoyl)-melatonin
-
-
N-benzoylanthranilic acids
-
-
-
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
NaCN
-
1 mM, 50% inhibition
naringenin
-
0.010 mM, 50% inhibition, oxidation of androstandiol
noranhydroicaritin
-
-
p-chloromercuribenzoate
-
0.1 mM, complete inhibition
p-coumaric acid
-
-
Phenolphthalein
quercetin
Sodium amytal
-
10 mM, 25% inhibition
stilboestrol
-
0.010 mM, 61% inhibition
tert-butyl(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
thiazolidinedione
-
-
Triton X-100
-
immediate loss of 60-70% activity, remaining activity is stable for 4 days, competitive vs. testosterone, non-competitive vs. NAD+
zearalenone
ZnCl2
-
10 mM, 10% inhibition
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
-
-
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
-
-
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
-
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
-
-
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
-
-
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
-
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
-
-
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
additional information
-