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(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol + NADP+
? + NADPH + H+
enzyme is stereoselective for benzo[g]chrysene-11S,12S-dihydrodiol
-
-
?
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide + NADPH + H+
?
-
-
-
-
r
(5beta,20R)-20-hydroxypregnan-3-one + NADH + H+
?
-
-
-
-
r
(S)-alpha-tetralol + NADP+
alpha-tetralone + NADPH + H+
-
-
-
?
(S)-tetralol + NADP+
? + NADPH
-
-
-
?
1-(4'nitrophenyl)prop-2-en-1-ol + NAD+
1-(4'nitrophenyl)prop-2-en-1-one + NADH
1-(4'nitrophenyl)prop-2-yn-1-ol + NAD+
1-(4'nitrophenyl)prop-2-yn-1-one + NADH
1-acenaphthenol + NAD(P)+
1-acenaphthenone + NAD(P)H + H+
1-acenaphthenol + NADPH
?
-
-
-
-
?
1-acetophenone + NADPH
1-phenylethanol + NADP+
-
-
-
-
?
1-indanone + NADPH
?
-
-
-
?
10-oxonortriptyline + NADPH
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
the rate of dihydrotestosterone reduction over back-conversion is 2.4 and 5.9 for prostate and epididymis, respectively
-
r
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
17beta-hydroxy-5alpha-androstan-3-one + NADPH
3alpha,17beta-dihydroxy-5alpha-androstan + NADP+
-
-
-
r
2 tibolone + 2 NADPH + 2 H+
3alpha-hydroxytibolone + 3beta-hydroxytibolone + 2 NADP+
2-acetylpyridine + NADPH
1-(2-pyridyl)ethanol + NADP+
-
stereoselective catalysis producing mainly the (S)-alcohols
-
-
?
2-decalone + NADH
? + NAD+
-
pH 6.0
-
?
3-acetylpyridine + NADPH
1-(3-pyridyl)ethanol + NADP+
-
low activity, stereoselective catalysis producing mainly the (S)-alcohols
-
-
?
3-ketosteroids + NADPH
3-hydroxysteroids + NADP+
-
-
-
?
3-oxo-cholic acid + NAD(P)H + H+
cholic acid + NAD(P)+
84.5% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
3-oxo-deoxycholic acid + NAD(P)H + H+
deoxycholic acid + NAD(P)+
-
-
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
3alpha-androstanediol + NAD+
5alpha-dihydrotestosterone + NADH + H+
-
steroid reduction direction is preferred
-
-
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
5alpha-androstan-3,17-dione + NADH
3alpha-hydroxy-5alpha-androstan-17-one + NADP+
5alpha-androstan-3,17-dione + NADPH
4'-methoxyacetophenone + NADPH + H+
1-(4-methoxyphenyl)ethanol + NADP+
-
-
R,S-enantiomeric product
-
?
4-acetylpyridine + NADPH + H+
(S)-1-(4-pyridyl)ethanol + NADP+
-
-
-
-
?
4-acetylpyridine + NADPH + H+
1-(4-pyridyl)ethanol + NADP+
-
stereoselective catalysis producing mainly the (S)-alcohols
-
-
?
4-androsten-3alpha-ol-17-one + NADH + H+
4-androsten-3alpha,17beta-diol + NAD+
-
AKR1C17
-
-
r
4-androstene-3,17-dione + NADH + H+
4-androsten-3alpha-ol-17-one + NAD+
-
low activity
-
-
r
4-bromoacetophenone + NADPH + H+
1-(4-bromophenyl)ethanol + NADP+
-
-
-
-
?
4-cyanoacetophenone + NADPH + H+
1-(4-cyanophenyl)ethanol + NADP+
-
-
-
-
?
4-hydroxynonenal + NADPH
?
-
-
-
?
4-methylacetophenone + NADPH + H+
1-(4-methylphenyl)ethanol + NADP+
-
-
R,S-enantiomeric product
-
?
4-nitroacetophenone + NAD(P)H
1-(4-nitrophenyl)ethanol + NAD(P)+
-
pH 6.0
-
?
4-nitroacetophenone + NADPH + H+
1-(4-nitrophenyl)ethanol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NAD(P)H
(4-nitrophenyl)methanol + NAD(P)+
4-oxo-2-nonenal + NADPH + H+
4-hydroxynonenal + NADP+
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
-
-
?
5alpha-androstan-3,17-dione + NAD(P)H
3alpha-hydroxy-5alpha-androstan-17-one + NAD(P)+
5alpha-androstan-3alpha-ol-17-one + NADH + H+
5beta-androstan-3alpha,17beta-diol + NAD+
5alpha-androstane-3,17-dione + NADH
5alpha-androstan-3alpha-ol-17-one + NAD+
-
low activity
AKR1C9
-
r
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-androstane-17beta-ol-3-one + NADPH
-
-
-
r
5alpha-androstanedione + NADPH + H+
5alpha-androstan-3alpha-ol-17-one + NADP+
-
-
i.e. allopregnanolone
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
-
?
5alpha-dihydrotestosterone + NADH
?
-
low activity
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-dihydrotestosterone + NADPH + H+
3alpha-androstanediol + NADP+
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnan-3alpha-ol-20-one + NAD(P)+
-
regulation of the amount of allosteric agonists that can bind to the GABA receptor in brain
-
r
5alpha-pregnan-3alpha,21-diol-20-one + NADP+
5alpha-pregnan-21-ol-3,20-dione + NADPH
-
-
-
r
5alpha-pregnane-20alpha-ol-3-one + NADH
5alpha-pregnane-3,20alpha-diol + NAD+
-
-
-
-
?
5alpha-pregnane-3,20-dione + NADH
5alpha-pregnan-3alpha-ol-20-one + NAD+
-
low activity
-
-
r
5beta-androstan-3alpha-ol-17-one + NAD(P)+
5beta-androstane-3,17-dione + NAD(P)H
-
-
-
-
r
5beta-androstan-3alpha-ol-17-one + NADH
5beta-androstane-3alpha,17beta-diol + NAD+
-
-
-
-
r
5beta-androstan-3alpha-ol-17-one + NADP+
5beta-androstan-3,17-dione + NADPH
-
-
-
?
5beta-androstane-3,17-dione + NADH
5beta-androstan-3alpha-ol-17-one + NAD+
-
-
-
-
r
5beta-androstane-3alpha,17beta-diol + NADP+
5beta-androstane-17beta-ol-3-one + NADPH
-
-
-
r
5beta-dihydrocortisone + NADPH
3alpha,17alpha,21-trihydroxy-5beta-pregnan-11,20-dione + NADP+
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD(P)+
5beta-pregnane-3,20-dione + NAD(P)H
-
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NADP+
5beta-pregnane-3,20-dione + NADPH
-
-
-
r
5beta-pregnane-17alpha,20beta,21-triol-3,11-dione + NAD(P)H
5beta-pregnane-3alpha,17alpha,20beta,21-tetraol-11-one + NAD(P)+
5beta-pregnane-20alpha-ol-3-one + NADH + H+
5beta-pregnane-3,20alpha-diol + NAD+
-
-
-
-
?
5beta-pregnane-3,20-dione + NADH + H+
5beta-pregnan-3alpha-ol-20-one + NAD+
-
-
-
-
r
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH
?
-
the enzyme produces both R- and S-form products in a ratio of 2.3 : 1
-
-
?
7alpha,12alpha-dihydroxy-5beta-cholestan-3-one + NADPH + H+
5beta-cholestane-3alpha,7alpha,12alpha-triol + NADP+
-
-
-
-
?
7alpha-hydroxy-5beta-cholestan-3-one + NADPH + H+
5beta-cholestane-3alpha,7alpha-diol + NADP+
-
-
-
-
?
9,10-phenanthrenequinone + NAD(P)H
? + NAD(P)+
9,10-phenanthrenequinone + NADH
?
-
-
-
-
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
acetophenone + NADPH + H+
1-phenylethanol + NADP+
-
-
-
-
?
androstan-17beta-ol-3-one + NADH
androstan-3alpha,17beta-diol + NAD+
-
-
-
?
androstan-3,17-dione + NADH
androstan-3alpha-ol-17-one + NAD+
-
-
-
?
androsterone + NAD(P)+
5alpha-androstane-3,17-dione + NAD(P)H
-
-
-
-
r
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
-
-
-
-
r
androsterone + NAD+
androstanedione + NADH
androsterone + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
-
r
benzenedihydrodiol + NAD(P)+
?
benzo[c]phenanthrene-3,4-dihydrodiol + NADP+
? + NADPH + H+
enzyme metabolizes both stereoisomers of benzo[c]phenanthrene-3,4-dihydrodiol
-
-
?
beta-muricholic acid + NADH
?
-
low activity
-
-
?
chenodeoxycholic acid + NAD(P)+
3-oxo-chenodeoxycholic acid + NAD(P)H + H+
19.8% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
chenodeoxycholic acid + NADH
?
-
-
-
-
?
cholic acid + NAD(P)+
3-oxo-cholic acid + NAD(P)H + H+
65.5% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
cholic acid + NAD(P)+
3-oxocholate + NAD(P)H
cholic acid + NADH
?
-
low activity
-
-
?
choloyl-CoA + NAD(P)+
3-oxocholoyl-CoA + NAD(P)H + H+
dehydrolithocholic acid + NADH + H+
?
-
-
-
-
?
deoxycholic acid + NAD(P)+
3-oxo-deoxycholic acid + NAD(P)H + H+
71.7% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
deoxycholic acid + NADH
?
-
low activity
-
-
?
deoxycholoyl-CoA + NAD(P)+
3-oxodeoxycholoyl-CoA + NAD(P)H + H+
diacetyl + NADH
?
-
-
-
-
?
dihydroprogesterone + NADPH
androsterone + NADP+
-
-
-
-
?
etiocholane-3,17-dione + NADH
etiocholan-3alpha-ol-17-one + NAD+
-
-
-
?
glycochenodeoxycholic acid + NAD(P)+
? + NAD(P)H + H+
50.7% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
glycochenodeoxycholic acid + NADH
?
-
-
-
-
?
glycochenodeoxycholic acid + NADP+
7alpha-hydroxy-3-oxo-5beta-cholanoyl glycine + NADPH
-
-
-
?
glycocholic acid + NAD(P)+
? + NAD(P)H + H+
61.2% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
glycodeoxycholic acid + NAD(P)+
? + NAD(P)H + H+
57.8% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
glycolithocholic acid + NADH
?
-
-
-
-
?
glycolithocholic acid + NADP+
3-oxo-5beta-cholanoyl glycine + NADPH
-
-
-
?
glycoursodeoxycholic acid + NADH
?
-
-
-
-
?
hyodeoxycholic acid + NADH
?
-
low activity
-
-
?
isatin + NADH
?
-
-
-
-
?
lithocholic acid + NADH
?
-
-
-
-
?
lithocholic acid + NADP+
dehydrolithocholic acid + NADPH
-
-
-
r
murocholic acid + NADH
?
-
low activity
-
-
?
oracin + NADPH
? + NADP+
-
-
-
-
?
pregnane-11beta,17alpha,21-triol-3,20-dione + NADH
pregnane-3alpha,11beta,17alpha,21-tetrol-20-one + NAD+
-
-
-
?
progesterone + NAD(P)H
3alpha-hydroxy-pregn-4-ene-20-one + NAD(P)+
-
-
-
-
r
prostaglandin + NADP+
? + NADPH
-
types A1, A2, B1, B2, D2, E1, E2, F1, F2alpha and 15-keto-prostaglandinE2 and F2alpha
-
?
prostaglandin-F2alpha + NADP+
prostaglandin F2 + prostaglandin B2 + NADPH
-
-
-
?
taurochenodeoxycholic acid + NAD(P)+
? + NAD(P)H + H+
53.3% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
taurocholic acid + NAD(P)+
? + NAD(P)H + H+
63.9% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
taurodeoxychloic acid + NAD(P)+
? + NAD(P)H + H+
59.2% of the activity compared to the substrate 3-oxodeoxycholic acid
-
-
r
taurolithocholic acid + NADH
?
-
-
-
-
?
tauroursodeoxycholic acid + NADH
?
-
-
-
-
?
testosterone + NAD(P)H + H+
4-androsten-3alpha,17beta-diol + NAD(P)+
-
-
-
-
r
testosterone + NADH
?
-
low activity
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
ursodeoxycholic acid + NADH
?
-
-
-
-
?
additional information
?
-
1-(4'nitrophenyl)prop-2-en-1-ol + NAD+
1-(4'nitrophenyl)prop-2-en-1-one + NADH
-
-
-
?
1-(4'nitrophenyl)prop-2-en-1-ol + NAD+
1-(4'nitrophenyl)prop-2-en-1-one + NADH
-
-
-
?
1-(4'nitrophenyl)prop-2-yn-1-ol + NAD+
1-(4'nitrophenyl)prop-2-yn-1-one + NADH
-
-
-
?
1-(4'nitrophenyl)prop-2-yn-1-ol + NAD+
1-(4'nitrophenyl)prop-2-yn-1-one + NADH
-
-
-
?
1-acenaphthenol + NAD(P)+
1-acenaphthenone + NAD(P)H + H+
-
pH 9.0
-
?
1-acenaphthenol + NAD(P)+
1-acenaphthenone + NAD(P)H + H+
-
pH 9.0
-
?
10-oxonortriptyline + NADPH
?
-
-
-
?
10-oxonortriptyline + NADPH
?
a drug acting as substrate
-
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
-
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
termination of androgen action
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
conversion in animal tissues
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
regulation of the amount of androgen in prostate, high levels of substrate are required for normal and abnormal growth of prostate
-
r
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
termination of androgen action
-
?
2 tibolone + 2 NADPH + 2 H+
3alpha-hydroxytibolone + 3beta-hydroxytibolone + 2 NADP+
i.e. tibolone, a 3-ketosteroid androgen receptor, conversion to potent estrogen receptor alpha agonists, tibolone induces estrogen receptor alpha-dependent gene promoter activity through cis-acting estrogen response elements, increases the stimulatory effect of TGF-beta on Smad-dependent gene promoter activity, and enhances prostaglandin E2-induced activity of transcription factor Runx2, overview
3alpha-hydroxytibolone is the primary metabolite
-
r
2 tibolone + 2 NADPH + 2 H+
3alpha-hydroxytibolone + 3beta-hydroxytibolone + 2 NADP+
i.e. tibolone, a 3-ketosteroid androgen receptor, conversion to potent estrogen receptor alpha agonists, overview
3alpha-hydroxytibolone is the primary metabolite
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP, the enzyme catalyzes the biosynthesis and oxidation of 3alpha,5alpha-reduced neurosteroids as allopregnanolone, which stimulates GABAA receptors, sciatic nerves-induced analgesia results in increased enzyme levels in neuropathic rats, overview
-
-
r
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP
-
-
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
5alpha-androstan-3,17-dione + NADH
-
-
-
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
5alpha-androstan-3,17-dione + NADH
-
-
-
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
5alpha-androstan-3,17-dione + NADH
-
-
-
r
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
5alpha-androstan-3,17-dione + NADH
-
pH 9.0
-
?
3alpha-hydroxy-5alpha-androstan-17-one + NAD+
5alpha-androstan-3,17-dione + NADH
-
pH 9.0
-
?
3alpha-hydroxy-5alpha-androstan-17-one + NADP+
5alpha-androstan-3,17-dione + NADPH
-
-
-
r
3alpha-hydroxy-5alpha-androstan-17-one + NADP+
5alpha-androstan-3,17-dione + NADPH
-
-
-
r
4-nitrobenzaldehyde + NAD(P)H
(4-nitrophenyl)methanol + NAD(P)+
-
pH 6.0
-
?
4-nitrobenzaldehyde + NAD(P)H
(4-nitrophenyl)methanol + NAD(P)+
-
pH 6.0
-
?
4-nitrobenzaldehyde + NAD(P)H
(4-nitrophenyl)methanol + NAD(P)+
-
NADH as cofactor
-
?
5alpha-androstan-3,17-dione + NAD(P)H
3alpha-hydroxy-5alpha-androstan-17-one + NAD(P)+
-
-
r
5alpha-androstan-3,17-dione + NAD(P)H
3alpha-hydroxy-5alpha-androstan-17-one + NAD(P)+
-
pH 6.0 for reduction, pH 7.0 and 9.0 for androsterone oxidation
-
r
5alpha-androstan-3,17-dione + NAD(P)H
3alpha-hydroxy-5alpha-androstan-17-one + NAD(P)+
-
pH 6.0 for reduction, pH 7.0 and 9.0 for androsterone oxidation
-
r
5alpha-androstan-3alpha-ol-17-one + NADH + H+
5beta-androstan-3alpha,17beta-diol + NAD+
-
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NADH + H+
5beta-androstan-3alpha,17beta-diol + NAD+
-
-
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
androgen-inactivating enzyme
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
the enzyme is important in inactivation of DHT
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
the enzyme plays a crucial role in the regulation of the intracellular concentrations of testosterone and 5alpha-dihydrotestosterone, two steroids directly linked to the etiology and the progression of many prostate diseases and cancer, overview
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
i.e. DHT
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
i.e. DHT, substrate and cofactor binding site structure
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
i.e. DHT, the enzyme prefers the reductive reaction
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
i.e. DHT
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
i.e. DHT or 5alpha-androstane-17beta-ol-3-one, the reduction reaction is slightly preferred by the wild-type enzyme, which is determined by residue Arg276
i.e. 5alpha-androstane-3alpha,17beta-diol
-
?
5alpha-dihydrotestosterone + NADPH + H+
3alpha-androstanediol + NADP+
-
steroid reduction direction is preferred
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
3alpha-androstanediol + NADP+
-
the chemical oxidation step is rate-limiting, W227 is very important for cataylsis, steroid reduction direction is preferred
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate, fluorometric activity measurement in intact cells, overview
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
i.e. DHT
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
i.e. DHT
-
-
r
5beta-pregnane-17alpha,20beta,21-triol-3,11-dione + NAD(P)H
5beta-pregnane-3alpha,17alpha,20beta,21-tetraol-11-one + NAD(P)+
-
-
-
r
5beta-pregnane-17alpha,20beta,21-triol-3,11-dione + NAD(P)H
5beta-pregnane-3alpha,17alpha,20beta,21-tetraol-11-one + NAD(P)+
-
hepatic reduction in animal tissues
-
?
9,10-phenanthrenequinone + NAD(P)H
? + NAD(P)+
-
NADPH
-
?
9,10-phenanthrenequinone + NAD(P)H
? + NAD(P)+
-
pH 6.0
-
?
9,10-phenanthrenequinone + NAD(P)H
? + NAD(P)+
-
pH 6.0
-
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
-
competitive substrate, fluorometric activity measurement in intact cells, overview
-
-
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
-
competitive substrate
-
-
?
acetohexamide + NADPH
?
-
-
-
?
acetohexamide + NADPH
?
a drug acting as substrate
-
-
?
androsterone + NAD+
androstanedione + NADH
-
-
-
-
r
androsterone + NAD+
androstanedione + NADH
-
the intramolecular proton transfer is a rate-limiting step, with a concomitant releasing of protons to bulk solvent
-
-
r
befunolol + NADPH
?
-
-
-
?
befunolol + NADPH
?
a drug acting as substrate
-
-
?
benzenedihydrodiol + NAD(P)+
?
-
-
-
?
benzenedihydrodiol + NAD(P)+
?
-
pH 9.0
-
?
benzenedihydrodiol + NAD(P)+
?
-
pH 9.0
-
?
cholic acid + NAD(P)+
3-oxocholate + NAD(P)H
-
-
very little activity
?
cholic acid + NAD(P)+
3-oxocholate + NAD(P)H
-
-
very little activity
?
choloyl-CoA + NAD(P)+
3-oxocholoyl-CoA + NAD(P)H + H+
-
-
-
r
choloyl-CoA + NAD(P)+
3-oxocholoyl-CoA + NAD(P)H + H+
-
-
-
r
daunorubicin + NADPH
?
-
-
-
?
daunorubicin + NADPH
?
a drug acting as substrate
-
-
?
deoxycholoyl-CoA + NAD(P)+
3-oxodeoxycholoyl-CoA + NAD(P)H + H+
-
75% activity compared with cholyl-CoA
-
?
deoxycholoyl-CoA + NAD(P)+
3-oxodeoxycholoyl-CoA + NAD(P)H + H+
-
75% activity compared with cholyl-CoA
-
?
dolasetron + NADPH
?
-
-
-
?
dolasetron + NADPH
?
a drug acting as substrate
-
-
?
haloperidol + NADPH
?
-
-
-
?
haloperidol + NADPH
?
a drug acting as substrate
-
-
?
ketoprofen + NADPH
?
-
-
-
?
ketoprofen + NADPH
?
a drug acting as substrate
-
-
?
ketotifen + NADPH
?
-
-
-
?
ketotifen + NADPH
?
a drug acting as substrate
-
-
?
loxoprofen + NADPH
?
-
-
-
?
loxoprofen + NADPH
?
a drug acting as substrate
-
-
?
Naloxone + NADPH
?
-
-
-
?
Naloxone + NADPH
?
a drug acting as substrate
-
-
?
Naltrexone + NADPH
?
-
-
-
?
Naltrexone + NADPH
?
a drug acting as substrate
-
-
?
oracin + NADPH
?
-
-
-
?
oracin + NADPH
?
a drug acting as substrate
-
-
?
oxycodone + NADPH
?
-
-
-
?
oxycodone + NADPH
?
a drug acting as substrate
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
tibolone is used to treat climacteric symptoms and prevent osteoporosis, it exerts tissue-selective effects via site-specific metabolism into 3alpha- and 3beta-hydroxymetabolites and a DELTA4-isomer
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
i.e. [7alpha,17alpha]-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one, stereoselctive reaction to the 3alpha-hydroxytibolone product
-
-
?
additional information
?
-
-
bifunctional enzyme exhibiting 3alpha-hydroxysteroid dehydrogenase activity and carbonyl reductase activity
-
-
?
additional information
?
-
no activity with isodeoxycholic acid
-
-
-
additional information
?
-
-
no activity with cholate, chenodeoxycholate, deoxycholate, glycocholate, taurocholate, ursodeoxycholate and bile acid
-
-
?
additional information
?
-
-
no activity with cholate, chenodeoxycholate, deoxycholate, glycocholate, taurocholate, ursodeoxycholate and bile acid
-
-
?
additional information
?
-
the enzyme is important in the synthesis of neuroactive 5alpha/beta-pregnan-3alpha-ol-20-ones from their precursors, the enzyme plays a role in development and progression of prostate cancer
-
-
?
additional information
?
-
-
the enzyme is important in the synthesis of neuroactive 5alpha/beta-pregnan-3alpha-ol-20-ones from their precursors, the enzyme plays a role in development and progression of prostate cancer
-
-
?
additional information
?
-
the RODH like 3alpha/17beta-HSD, EC 1.1.1.239, regulates the transactivation of AKR1C2, overview
-
-
?
additional information
?
-
-
the RODH like 3alpha/17beta-HSD, EC 1.1.1.239, regulates the transactivation of AKR1C2, overview
-
-
?
additional information
?
-
besides 3alpha-hydroxysteroid dehydrogenase activity, the enzyme shows also 17beta-hydroxysteroid dehydrogenase activity towards 5alpha-dihydrotestosterone, EC 1.1.1.239, overview, the enzyme reveals an 'induced-fit' mechanism and a conserved basic motif involved in the binding of androgen, the enzyme also binds many structurally different molecules such as 4-hydroxynonenal, polycyclic aromatic hydrocarbons, and indanone
-
-
?
additional information
?
-
-
besides 3alpha-hydroxysteroid dehydrogenase activity, the enzyme shows also 17beta-hydroxysteroid dehydrogenase activity towards 5alpha-dihydrotestosterone, EC 1.1.1.239, overview, the enzyme reveals an 'induced-fit' mechanism and a conserved basic motif involved in the binding of androgen, the enzyme also binds many structurally different molecules such as 4-hydroxynonenal, polycyclic aromatic hydrocarbons, and indanone
-
-
?
additional information
?
-
-
AKR1C3 catalyzes androgen, estrogen, and prostaglandin metabolism, AKR1C3 is also involved in cancer development or progression
-
-
?
additional information
?
-
-
an androgen-inactivating enzyme, important in androgen and progesterone metabolism
-
-
?
additional information
?
-
-
the enzyme might play an important role in female physiology, substrate specificity, overview
-
-
?
additional information
?
-
-
metabolizes androgens and glucocorticoids, function as a dihydrodiol dehydrogenase as well as 9-, 11-, and 15-hydroxyprostaglandin dehydrogenase, enzyme catalyzes both oxidation and reduction reaction at physiological pH and is able to reduce aromatic ketones
-
-
?
additional information
?
-
-
the enzyme displays a distinct preference for the reduction of quinones, e.g. 9,10-phenanthrenequinone, and 3-oxo steroids, e.g. androstane, pregnane and cholane, over aromatic aldehydes and ketones, whereas 3alpha-hydroxy steroids are overwhelmingly more efficiently oxidized than are 1-acenaphthenol or benzenedihydrodiol. Ethanol and 3beta-hydroxy steroids no substrates
-
-
?
additional information
?
-
-
oxidation of 3alpha-hydroxysteroids, secondary alcohols and trans-dihydrodiol proximate carcinogens derived from polycyclic aromatic hydrocarbons, reduction of quinones, aromatic aldehydes and ketones, 9-, 11-, and 15-hydroxyprostaglandin dehydrogenase activity of enzyme
-
-
?
additional information
?
-
biosynthesis and inactivation of steroid hormones, physiological role is to inactivate circulating androgens, progestins and glucocorticoids
-
-
?
additional information
?
-
-
involved in biosynthesis of bile acids
-
-
?
additional information
?
-
-
inactivating circulating androgens, progestins and glucocorticoids. Regulation of hormone levels in endocrine target tissues and in carcinogen actibation
-
-
?
additional information
?
-
-
no activity with acetylpyrroles
-
-
?
additional information
?
-
-
AKR1C9 catalyzes androgen, estrogen, and prostaglandin metabolism
-
-
?
additional information
?
-
C/EBPdelta regulates the AKR1C9 gene promoter in osteoblasts, overview
-
-
?
additional information
?
-
-
acetophenone derivatives are reduced enantioselectively by rat liver 3alpha-HSD to give (S)-alcohols
-
-
?
additional information
?
-
-
substrate specificty, overview, recombinant AKR1C17 efficiently oxidizes 3alpha-hydroxysteroids and diverse bile acids using NAD+ as the preferred coenzyme, no activity with progesterone, cortisone, and aldosterone. The enzyme also reduces non-steroidal alpha-dicarbonyl compounds such as 9,10-phenanethrenequinone, isatin, 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one and diacetyl, but does not show significant activities towards 4-nitrobenzaldehyde and 4-nitroacetophenone
-
-
?
additional information
?
-
-
metabolizes androgens and glucocorticoids, function as a dihydrodiol dehydrogenase as well as 9-, 11-, and 15-hydroxyprostaglandin dehydrogenase, enzyme catalyzes both oxidation and reduction reaction at physiological pH and is able to reduce aromatic ketones
-
-
?
additional information
?
-
-
involved in biosynthesis of bile acids
-
-
?
additional information
?
-
-
the enzyme displays a distinct preference for the reduction of quinones, e.g. 9,10-phenanthrenequinone, and 3-oxo steroids, e.g. androstane, pregnane and cholane, over aromatic aldehydes and ketones, whereas 3alpha-hydroxy steroids are overwhelmingly more efficiently oxidized than are 1-acenaphthenol or benzenedihydrodiol. Ethanol and 3beta-hydroxy steroids no substrates
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
10-oxonortriptyline + NADPH
?
a drug acting as substrate
-
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
2 tibolone + 2 NADPH + 2 H+
3alpha-hydroxytibolone + 3beta-hydroxytibolone + 2 NADP+
i.e. tibolone, a 3-ketosteroid androgen receptor, conversion to potent estrogen receptor alpha agonists, tibolone induces estrogen receptor alpha-dependent gene promoter activity through cis-acting estrogen response elements, increases the stimulatory effect of TGF-beta on Smad-dependent gene promoter activity, and enhances prostaglandin E2-induced activity of transcription factor Runx2, overview
3alpha-hydroxytibolone is the primary metabolite
-
r
3-ketosteroids + NADPH
3-hydroxysteroids + NADP+
-
-
-
?
3alpha,5alpha-allopregnenolone + NAD(P)+
5alpha-dihydroprogesterone + NAD(P)H
-
i.e. 3alpha,5alpha-tetrahydroprogesterone or 3alpha,5alpha-THP, the enzyme catalyzes the biosynthesis and oxidation of 3alpha,5alpha-reduced neurosteroids as allopregnanolone, which stimulates GABAA receptors, sciatic nerves-induced analgesia results in increased enzyme levels in neuropathic rats, overview
-
-
r
3alpha-androstanediol + NAD+
5alpha-dihydrotestosterone + NADH + H+
-
steroid reduction direction is preferred
-
-
r
4-acetylpyridine + NADPH + H+
(S)-1-(4-pyridyl)ethanol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NAD(P)H + H+
5alpha-androstane-3alpha,17beta-diol + NAD(P)+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
5alpha-dihydrotestosterone + NADPH + H+
3alpha-androstanediol + NADP+
-
steroid reduction direction is preferred
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
5alpha-pregnan-3,20-dione + NAD(P)H + H+
5alpha-pregnan-3alpha-ol-20-one + NAD(P)+
-
regulation of the amount of allosteric agonists that can bind to the GABA receptor in brain
-
r
5beta-pregnane-17alpha,20beta,21-triol-3,11-dione + NAD(P)H
5beta-pregnane-3alpha,17alpha,20beta,21-tetraol-11-one + NAD(P)+
-
hepatic reduction in animal tissues
-
?
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADPH
9-[hydroxy(phenyl)methyl]-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one + NADP+
-
competitive substrate, fluorometric activity measurement in intact cells, overview
-
-
?
acetohexamide + NADPH
?
a drug acting as substrate
-
-
?
acetophenone + NADPH + H+
1-phenylethanol + NADP+
-
-
-
-
?
androsterone + NAD+
5alpha-androstane-3,17-dione + NADH
-
-
-
-
r
androsterone + NAD+
androstanedione + NADH
-
-
-
-
r
androsterone + NADP+
5alpha-androstane-3,17-dione + NADPH
-
-
-
-
r
befunolol + NADPH
?
a drug acting as substrate
-
-
?
daunorubicin + NADPH
?
a drug acting as substrate
-
-
?
dolasetron + NADPH
?
a drug acting as substrate
-
-
?
haloperidol + NADPH
?
a drug acting as substrate
-
-
?
ketoprofen + NADPH
?
a drug acting as substrate
-
-
?
ketotifen + NADPH
?
a drug acting as substrate
-
-
?
loxoprofen + NADPH
?
a drug acting as substrate
-
-
?
Naloxone + NADPH
?
a drug acting as substrate
-
-
?
Naltrexone + NADPH
?
a drug acting as substrate
-
-
?
oracin + NADPH
?
a drug acting as substrate
-
-
?
oxycodone + NADPH
?
a drug acting as substrate
-
-
?
tibolone + NADPH + H+
3-hydroxytibolone + NADP+
-
tibolone is used to treat climacteric symptoms and prevent osteoporosis, it exerts tissue-selective effects via site-specific metabolism into 3alpha- and 3beta-hydroxymetabolites and a DELTA4-isomer
-
-
?
additional information
?
-
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
-
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
termination of androgen action
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
conversion in animal tissues
-
?
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
regulation of the amount of androgen in prostate, high levels of substrate are required for normal and abnormal growth of prostate
-
r
17beta-hydroxy-5alpha-androstan-3-one + NAD(P)H + H+
3alpha,17beta-dihydroxy-5alpha-androstan + NAD(P)+
-
termination of androgen action
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
androgen-inactivating enzyme
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
the enzyme is important in inactivation of DHT
-
-
?
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
the enzyme plays a crucial role in the regulation of the intracellular concentrations of testosterone and 5alpha-dihydrotestosterone, two steroids directly linked to the etiology and the progression of many prostate diseases and cancer, overview
-
-
r
5alpha-dihydrotestosterone + NADPH
5alpha-androstane-3alpha,17beta-diol + NADP+
-
-
-
-
?
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate
-
-
r
5alpha-dihydrotestosterone + NADPH + H+
5alpha-androstan-3alpha,17beta-diol + NADP+
-
inactivation of the potent androgen in human prostate, fluorometric activity measurement in intact cells, overview
-
-
?
additional information
?
-
the enzyme is important in the synthesis of neuroactive 5alpha/beta-pregnan-3alpha-ol-20-ones from their precursors, the enzyme plays a role in development and progression of prostate cancer
-
-
?
additional information
?
-
-
the enzyme is important in the synthesis of neuroactive 5alpha/beta-pregnan-3alpha-ol-20-ones from their precursors, the enzyme plays a role in development and progression of prostate cancer
-
-
?
additional information
?
-
the RODH like 3alpha/17beta-HSD, EC 1.1.1.239, regulates the transactivation of AKR1C2, overview
-
-
?
additional information
?
-
-
the RODH like 3alpha/17beta-HSD, EC 1.1.1.239, regulates the transactivation of AKR1C2, overview
-
-
?
additional information
?
-
-
AKR1C3 catalyzes androgen, estrogen, and prostaglandin metabolism, AKR1C3 is also involved in cancer development or progression
-
-
?
additional information
?
-
-
an androgen-inactivating enzyme, important in androgen and progesterone metabolism
-
-
?
additional information
?
-
biosynthesis and inactivation of steroid hormones, physiological role is to inactivate circulating androgens, progestins and glucocorticoids
-
-
?
additional information
?
-
-
involved in biosynthesis of bile acids
-
-
?
additional information
?
-
-
inactivating circulating androgens, progestins and glucocorticoids. Regulation of hormone levels in endocrine target tissues and in carcinogen actibation
-
-
?
additional information
?
-
-
AKR1C9 catalyzes androgen, estrogen, and prostaglandin metabolism
-
-
?
additional information
?
-
C/EBPdelta regulates the AKR1C9 gene promoter in osteoblasts, overview
-
-
?
additional information
?
-
-
involved in biosynthesis of bile acids
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(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-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
93.5% inhibition at 0.1 mM
(E/Z)-sulfindac
-
wild-type, W86Y and W227Y
1,10-phenanthroline
-
wild-type, W86Y and W227Y
1,7-phenanthroline
-
wild-type, W86Y and W227Y
1-(4'nitrophenyl)prop-2-en-1-ol
-
inactivation dependent on NAD+ concentration, optimal at 0.5-1.0 mM NAD+, 2-mercaptoethanol prvides a concentration-dependent protection
1-(4'nitrophenyl)prop-2-en-1-one
-
inactivation can be retarded markedly in a concentration-dependent manner by both NADH and NADPH. Competitive inhibitor of NAD+ binding, measured for androsterone oxidation
1-(4'nitrophenyl)prop-2-yn-1-one
-
competitive inhibitor of NAD+ binding, measured for androsterone oxidation
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
17beta-bromoacetoxy-5alpha-dihydrotestosterone
-
inactivation by modification of steroid-binding site
2'-hydroxyflavanone
-
most potent inhibitor, 0.02 mM inhibits by 98.9% and in an uncompetitive manner
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-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
-
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
-
21-hydroxypregn-4-ene-3,20-dione
-
-
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-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-[[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
4-androstene-3,17-dione
-
versus substrate, the products, 4-androstene-3,17-dione and NADH, inhibit the activity uncompetitively and competitively, respectively, with respect to NAD+ in the presence of a saturated concentration of 0.004 mM of the substrate
5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
-
5beta-Pregnan-3beta-ol-20-one
-
-
6alpha-Methylprednisolone
-
-
7-hydroxyflavone
-
very potent inhibitor, 0.02 mM inhibits by 82.5%
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one
-
competitive
acetaminophen
-
non-competitive, only androsterone oxidation, pH 7.0
acetylenic ketones
-
inactivation by forming Michael adducts with enzyme nucleophiles
-
apigenin
-
0.02 mM inhibits by ca. 50%
aspirin
-
salicylate, non-competitive, only androsterone oxidation, pH 7.0
Betamethasone
-
non-competitive
celecoxib
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.050 mM in fluorometric assay, in vitro IC50: 0.050 mM in fluorometric assay
Cibacron blue
-
nucleotide analog, competitive with respect to NADP+, noncompetitive to androsterone
Cu2+
-
100% inhibition at 0.1 mM
D-glucose 6-phosphate
-
-
epigallocatechin gallate
-
-
iodoacetate
-
50% inhibition at 0.1 mM
Ketamine
-
specific inhibitor for AKR1C17, but no inhibition of AKR1C9
luteolin
-
0.02 mM inhibits by ca. 50%
Medroxyprogesterone acetate
-
-
Mefenamic acid
-
wild-type, W86Y and W227Y
NADH
-
the products, 4-androstene-3,17-dione and NADH, inhibit the activity uncompetitively and competitively, respectively, with respect to NAD+ in the presence of a saturated concentration of 0.004 mM of the substrate
naphthalene-1,2-dione
naphthalene-1,2-dione leads to the time and concentration dependent irreversible inactivation of AKR1C9 via alkylation
naproxen
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.0094 mM in fluorometric assay, 0.016 mM in radiometric assay, in vitro IC50: 0.0027 mM in fluorometric assay
naringenin
-
very potent inhibitor, 0.02 mM inhibits by 71.9%
non-steroidal anti-inflamatory drug
-
Oxyphenybutazone
-
competitive
p-chloromercuribenzenesulfonate
-
-
Phenolphthalein
-
AKR1C4-selective inhibitor, in vitro and in vivo inhibition, IC50: 0.0004 mM
ponalrestat
-
wild-type, W86Y and W227Y, weak inhibitor
Prednisolone
-
competitive
progesterone
-
competitive to testosterone
prostaglandin A2alpha
-
-
prostaglandin F1alpha
-
-
quercetin
-
0.02 mM inhibits by ca. 50%
salicylate
-
non-competitive
silibinin
-
0.02 mM inhibits by ca. 50%
Tolmetin
-
competitive, only androsterone oxidation, pH 7.0
ursodeoxycholate
-
natural inhibitor, in vivo IC50: 0.00024 mM in fluorometric assay, 0.00014 mM in radiometric assay, in vitro IC50: 0.000049 mM in fluorometric assay
Zomepirac
-
competitive, only androsterone oxidation, pH 7.0
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
250fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
in complex with AKR1C3. Compound adopts a similar binding orientation as flufenamic acid, however, its phenylamino ring projects deeper into a subpocket and confers selectivity over the other AKR1C isoforms
dexamethasone
-
-
dexamethasone
-
non-competitive
Flufenamic acid
-
a nonsteroidalanti-inflammatory drug, IC50: 1.084 mM
Flufenamic acid
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.0040 mM in fluorometric assay, in vitro IC50: 0.00031 mM in fluorometric assay
Flufenamic acid
-
wild-type, W86Y and W227Y
Hexestrol
-
-
Hexestrol
-
hydroxysteroid analog, uncompetitive versus NADP+, competitive versus androsterone
Ibuprofen
-
synthetic, nonsteroidal anti-inflammatory inhibitor, in vivo IC50: 0.017 mM in fluorometric assay, in vitro IC50: 0.009 mM in fluorometric assay
indomethacin
-
non-steroidal anti-inflamatory drug, uncompetitive against NAD+, competitive against androsterone
indomethacin
-
competitive, IC50 for reduction of 9,10-phenanthrenequinone is 0.000735 mM and of androsterone 0.00333 mM
indomethacin
-
wild-type, W86Y and W227Y
Meclofenamic acid
-
competitive
Meclofenamic acid
-
wild-type, W86Y and W227Y
non-steroidal anti-inflamatory drug
-
-
-
non-steroidal anti-inflamatory drug
-
competitive
-
non-steroidal anti-inflamatory drug
-
-
-
p-chloromercuribenzoate
-
-
p-chloromercuribenzoate
-
non-competitive with respect to dihydrocortisone 46-100% inhibition at 0.01 mM, preincubation with NADH lowers the inhibitory effect
Prostaglandin
-
A2alpha
Prostaglandin
-
A1, B1, E1, F1, F1alpha, A2, B2, E2 and F2alpha, inhibit 9,10-phenanthrenequinone reduction and androsterone oxidation, the order of inhibitory potency is related to their lipophilicity
testosterone
-
competitive inhibitor of androsterone binding
testosterone
-
competitive to progesterone
zopolrestat
-
wild-type, W86Y and W227Y, weak inhibitor
additional information
-
no inhibition by the bile acid 5beta-cholanic acid-3alpha,7alpha-diol
-
additional information
-
dutasteride alters the expression level of the enzyme in breast cancer cells, the inhibitor affects the 5alpha-progesterone reductase and the progesterone metabolism, overview
-
additional information
-
is not inhibited by 0.02 mM caffeic acid, rutin, 4-hydroxybenzoic acid, cyanin chloride and taxifolin
-
additional information
-
not inhibited by dicoumarol, disulfiram and barbiturates. Inhibitory potency of non-steroidal anti-inflamatory drugs and salicylates falls sharply as the pH is increased from 6 to 9
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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Adenocarcinoma
Expression of dihydrodiol dehydrogenase and resistance to chemotherapy and radiotherapy in adenocarcinoma cells of lung.
Adenocarcinoma
[Gene expression profiling of human ovarian epithelial tumors by digo nucleotide microarray]
Breast Neoplasms
An indomethacin analogue, N-(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies.
Breast Neoplasms
Selective loss of AKR1C1 and AKR1C2 in breast cancer and their potential effect on progesterone signaling.
Carcinoma
Dihydrodiol dehydrogenase in drug resistance and sensitivity of human carcinomas.
Carcinoma
Expression and characterization of recombinant type 2 3 alpha-hydroxysteroid dehydrogenase (HSD) from human prostate: demonstration of bifunctional 3 alpha/17 beta-HSD activity and cellular distribution.
Carcinoma
Expression of dihydrodiol dehydrogenase plays important roles in apoptosis- and drug-resistance of A431 squamous cell carcinoma.
Carcinoma
Increased expression of dihydrodiol dehydrogenase induces resistance to cisplatin in human ovarian carcinoma cells.
Carcinoma
Inverse expression of dihydrodiol dehydrogenase and glutathione-S-transferase in patients with esophageal squamous cell carcinoma.
Carcinoma
Sequence of the cDNA of a human dihydrodiol dehydrogenase isoform (AKR1C2) and tissue distribution of its mRNA.
Carcinoma
Steroid-converting enzymes in human ovarian carcinomas.
Carcinoma
Ubiquitous induction of resistance to platinum drugs in human ovarian, cervical, germ-cell and lung carcinoma tumor cells overexpressing isoforms 1 and 2 of dihydrodiol dehydrogenase.
Carcinoma
[Gene expression profiling of human ovarian epithelial tumors by digo nucleotide microarray]
Carcinoma, Hepatocellular
Characterization of dihydrodiol dehydrogenase in rat H-4IIe hepatoma cells.
Carcinoma, Hepatocellular
Proteome analysis of rat hepatomas: carcinogen-dependent tumor-associated protein variants.
Carcinoma, Hepatocellular
Reduction of dihydrodiol dehydrogenase expression in resected hepatocellular carcinoma.
Carcinoma, Non-Small-Cell Lung
Expression of dihydrodiol dehydrogenase in the resected stage I non-small cell lung cancer.
Carcinoma, Non-Small-Cell Lung
Overexpression of dihydrodiol dehydrogenase as a prognostic marker of non-small cell lung cancer.
Carcinoma, Non-Small-Cell Lung
Proteomics-based identification of secreted protein dihydrodiol dehydrogenase as a novel serum markers of non-small cell lung cancer.
Carcinoma, Ovarian Epithelial
Steroid-converting enzymes in human ovarian carcinomas.
Carcinoma, Squamous Cell
Expression of dihydrodiol dehydrogenase plays important roles in apoptosis- and drug-resistance of A431 squamous cell carcinoma.
Cataract
Inhibition of naphthalene cataract in rats by aldose reductase inhibitors.
Colorectal Neoplasms
The long variant of human ileal bile acid-binding protein associated with colorectal cancer exhibits sub-cellular localization and lipid binding behaviour distinct from those of the common isoform.
Dupuytren Contracture
Common Variants of the ALDH2 and DHDH Genes and the Risk of Dupuytren's Disease.
Epilepsy
Characterization of the 5alpha-reductase-3alpha-hydroxysteroid dehydrogenase complex in the human brain.
Esophageal Squamous Cell Carcinoma
Inverse expression of dihydrodiol dehydrogenase and glutathione-S-transferase in patients with esophageal squamous cell carcinoma.
Glaucoma
Altered expression of 3 alpha-hydroxysteroid dehydrogenases in human glaucomatous optic nerve head astrocytes.
Hepatoblastoma
Hepatocyte nuclear factor (HNF)-4 alpha/gamma, HNF-1 alpha, and vHNF-1 regulate the cell-specific expression of the human dihydrodiol dehydrogenase (DD)4/AKR1C4 gene.
Hirsutism
3{alpha}-Hydroxysteroid Dehydrogenase Type III Deficiency: A Novel Mechanism for Hirsutism.
Hirsutism
Cutaneous androgen metabolism: basic research and clinical perspectives.
Hypercholesterolemia
Identification of a novel hypocholesterolemic protein, major royal jelly protein 1, derived from royal jelly.
Hyperglycemia
Pathogenesis of diabetic neuropathy--do hyperglycemia and aldose reductase inhibitors affect neuroactive steroid formation in the rat sciatic nerves?
Infections
Infection of human papillomavirus and overexpression of dihydrodiol dehydrogenase in uterine cervical cancer.
Liver Diseases
Serum bile acid concentrations in patients with liver disease.
Lung Neoplasms
A possible role for dihydrodiol dehydrogenase in the formation of benzo[a]pyrene-DNA adducts in lung cancer cells and tumor tissues.
Lung Neoplasms
Diagnostic value of serum dihydrodiol dehydrogenase 2 levels in patients with non-small-cell lung cancer.
Lung Neoplasms
Expression of dihydrodiol dehydrogenase in the resected stage I non-small cell lung cancer.
Lung Neoplasms
Overexpression of dihydrodiol dehydrogenase as a prognostic marker of non-small cell lung cancer.
Lung Neoplasms
Proteomics-based identification of secreted protein dihydrodiol dehydrogenase as a novel serum markers of non-small cell lung cancer.
Melanoma
Sebocytes are the key regulators of androgen homeostasis in human skin.
Neoplasm Metastasis
Extracts of Koelreuteria henryi Dummer induce apoptosis and autophagy by inhibiting dihydrodiol dehydrogenase, thus enhancing anticancer effects.
Neoplasm Metastasis
Hepatocyte growth factor and HER2/neu downregulate expression of apoptosis-inducing factor in non-small cell lung cancer.
Neoplasms
A possible role for dihydrodiol dehydrogenase in the formation of benzo[a]pyrene-DNA adducts in lung cancer cells and tumor tissues.
Neoplasms
An indomethacin analogue, N-(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies.
Neoplasms
Dihydrodiol dehydrogenases regulate the generation of reactive oxygen species and the development of cisplatin resistance in human ovarian carcinoma cells.
Neoplasms
Evaluation of the prognostic role of a panel of biomarkers in stage IB-IIIA non-small cell lung cancer patients.
Neoplasms
Extracts of Koelreuteria henryi Dummer induce apoptosis and autophagy by inhibiting dihydrodiol dehydrogenase, thus enhancing anticancer effects.
Neoplasms
Glutathione-related enzymes contribute to resistance of tumor cells and low toxicity in normal organs to artesunate.
Neoplasms
Hepatocyte growth factor and HER2/neu downregulate expression of apoptosis-inducing factor in non-small cell lung cancer.
Neoplasms
Inhibition of 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C(18)-, C(19)- and C(21)-hydroxysteroids and ketosteroids.
Neoplasms
Temporal and spatial patterns of ovarian gene transcription following an ovulatory dose of gonadotropin in the rat.
Neoplasms
Ubiquitous induction of resistance to platinum drugs in human ovarian, cervical, germ-cell and lung carcinoma tumor cells overexpressing isoforms 1 and 2 of dihydrodiol dehydrogenase.
Neoplasms
[Gene expression profiling of human ovarian epithelial tumors by digo nucleotide microarray]
Neoplasms, Germ Cell and Embryonal
Dihydrodiol dehydrogenases regulate the generation of reactive oxygen species and the development of cisplatin resistance in human ovarian carcinoma cells.
Optic Nerve Injuries
Altered expression of 3 alpha-hydroxysteroid dehydrogenases in human glaucomatous optic nerve head astrocytes.
Ovarian Neoplasms
Overexpression of dihydrodiol dehydrogenase is associated with cisplatin-based chemotherapy resistance in ovarian cancer patients.
Pneumonia
Increased annexin A1 and A2 levels in bronchoalveolar lavage fluid are associated with resistance to respiratory disease in beef calves.
Prostatic Hyperplasia
Expression and characterization of recombinant type 2 3 alpha-hydroxysteroid dehydrogenase (HSD) from human prostate: demonstration of bifunctional 3 alpha/17 beta-HSD activity and cellular distribution.
Prostatic Hyperplasia
Function of human brain short chain L-3-hydroxyacyl coenzyme A dehydrogenase in androgen metabolism.
Prostatic Neoplasms
5alpha-androstane-3alpha,17beta-diol selectively activates the canonical PI3K/AKT pathway: a bioinformatics-based evidence for androgen-activated cytoplasmic signaling.
Prostatic Neoplasms
5alpha-androstane-3alpha,17beta-diol supports human prostate cancer cell survival and proliferation through androgen receptor-independent signaling pathways: implication of androgen-independent prostate cancer progression.
Stomach Neoplasms
Identification of genes differentially expressed between gastric cancers and normal gastric mucosa with cDNA microarrays.
Stomach Neoplasms
Overexpression of dihydrodiol dehydrogenase as a prognostic marker in resected gastric cancer patients.
Uterine Cervical Neoplasms
Infection of human papillomavirus and overexpression of dihydrodiol dehydrogenase in uterine cervical cancer.
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0.0027
(5beta,20R)-20-hydroxypregnan-3-one
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.0012 - 0.726
17beta-hydroxy-5alpha-androstan-3-one
3.54 - 33.7
2-decalone
-
-
0.179
3-oxo-deoxycholic acid
coenzyme: NADPH, pH 7.0, temperature not specified in the publication
-
0.0031
3alpha-androstanediol
-
pH 7.0, 25°C, recombinant enzyme
0.0013 - 0.408
3alpha-hydroxy-5alpha-androstan-17-one
0.163 - 0.211
4-nitrobenzaldehyde
-
-
0.0031
4-oxo-2-nonenal
pH 7.4, 25°C
0.0011 - 0.0304
5alpha-androstan-3,17-dione
0.00008 - 0.00065
5alpha-androstane-3,17-dione
0.781 - 7.331
5alpha-androstane-3alpha,17beta-diol
0.0013 - 0.012
5alpha-dihydrotestosterone
0.0021
5beta-androstane-3,17-dione
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.01
5beta-pregnane-17alpha,20beta,21-triol-3,11-dione
-
-
0.0024
5beta-pregnane-3,20-dione
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.023
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.00122 - 0.038
9,10-phenanthrenequinone
0.003
9-(phenylcarbonyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one
-
recombinant enzyme in intact COS-1 cells
0.00044 - 0.1
androsterone
0.004
Dehydrolithocholic acid
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.155
deoxycholic acid
coenzyme: NADP+, pH 10, temperature not specified in the publication
0.42
diacetyl
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.022
isatin
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
additional information
(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol
0.0012
17beta-hydroxy-5alpha-androstan-3-one
-
cloned human liver enzyme type I
0.0192
17beta-hydroxy-5alpha-androstan-3-one
-
cloned human liver enzyme type II
0.505
17beta-hydroxy-5alpha-androstan-3-one
-
NAD(H), prostate
0.614
17beta-hydroxy-5alpha-androstan-3-one
-
NADP(H), prostate
0.645
17beta-hydroxy-5alpha-androstan-3-one
-
NADP(H), epididymis
0.726
17beta-hydroxy-5alpha-androstan-3-one
-
NAD(H), epididymis
0.0013 - 0.0441
3alpha-hydroxy-5alpha-androstan-17-one
NAD+
0.0041 - 0.024
3alpha-hydroxy-5alpha-androstan-17-one
NADP+
0.0094
3alpha-hydroxy-5alpha-androstan-17-one
-
-
0.029
3alpha-hydroxy-5alpha-androstan-17-one
-
Y205F
0.042 - 0.408
3alpha-hydroxy-5alpha-androstan-17-one
-
-
0.046
3alpha-hydroxy-5alpha-androstan-17-one
-
recombinant wild type enzyme
0.047
3alpha-hydroxy-5alpha-androstan-17-one
-
-
0.0011 - 0.0039
5alpha-androstan-3,17-dione
NADPH
0.0017
5alpha-androstan-3,17-dione
-
-
0.0039 - 0.0304
5alpha-androstan-3,17-dione
NADH
0.0041
5alpha-androstan-3,17-dione
-
recombinant wild type enzyme
0.0042
5alpha-androstan-3,17-dione
-
Y205F
0.00008
5alpha-androstane-3,17-dione
-
-
0.00065
5alpha-androstane-3,17-dione
-
pH 7.0, 25, reduction reaction
0.781
5alpha-androstane-3alpha,17beta-diol
-
NAD(H), prostate
1.09
5alpha-androstane-3alpha,17beta-diol
-
NADP(H), prostate
3.042
5alpha-androstane-3alpha,17beta-diol
-
NAD(H), epididymis
7.331
5alpha-androstane-3alpha,17beta-diol
-
NADP(H), epididymis
0.0013
5alpha-dihydrotestosterone
-
recombinant enzyme in intact COS-1 cells
0.0029
5alpha-dihydrotestosterone
-
pH 7.0, 25°C, recombinant enzyme
0.0057
5alpha-dihydrotestosterone
pH 7.5, recombinant wild-type enzyme
0.0059
5alpha-dihydrotestosterone
pH 7.5, recombinant mutant R301L
0.012
5alpha-dihydrotestosterone
pH 7.5, recombinant mutant R304L
0.00122 - 0.0051
9,10-phenanthrenequinone
-
-
0.038
9,10-phenanthrenequinone
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.00044
androsterone
-
pH 9.0, 25°C, recombinant mutant S114A/Y155F
0.0041
androsterone
-
pH 7.0, 25, oxidation reaction
0.0051
androsterone
-
pH 10.4, 25°C, recombinant wild-type enzyme
0.0055
androsterone
-
pH 9.0, 25°C, recombinant wild-type enzyme
0.007
androsterone
-
pH 9.0, 25°C, recombinant mutant S114A
0.033
androsterone
-
pH 10.4, 25°C, recombinant mutant K159A
0.065
androsterone
-
pH 9.0, 25°C, recombinant mutant K159A
0.074
androsterone
-
pH 9.0, 25°C, recombinant mutant Y155F
0.1
androsterone
-
pH 9.0, 25°C, recombinant mutant Y155F/K159A
0.004 - 0.821
NAD+
-
0.94
NAD+
-
recombinant wild type enzyme
0.0057 - 0.0312
NADH
-
0.027
NADH
-
recombinant wild type enzyme
0.0026
NADP+
-
-
0.00016
NADPH
-
-
additional information
(11S,12S)-11,12-dihydrobenzo[g]chrysene-11,12-diol
racemic benzo[g]chrysene-11,12-dihydrodiol derived from the fjord-region parent hydrocarbon benzo[g]chrysene is oxidized with a kcat/Km of 1520 min/mM, which is more than 100 times greater than that observed with benzo[a]pyrene-7,8-dihydrodiol
additional information
benzo[a]pyrene-7,8-dihydrodiol
kcat/Km of 39 min/mM
additional information
additional information
-
kinetics
-
additional information
additional information
-
steady-state kinetics
-
additional information
additional information
-
transient-state and steady-state kinetics
-
additional information
additional information
-
equilibrium kinetics of wild-type and mutant enzymes
-
additional information
additional information
-
stereoselectivity, kinetics
-
additional information
additional information
-
transient single and multiple turnover kinetics, stopped flow kinetics, isotope kinetics, ligand binding analysis, kinetics with deuterium-substituted cofactor and binary complex of enzyme and cofactor, overview
-
additional information
additional information
-
cofactor kinetics of wild-type and mutant enzymes, overview
-
additional information
additional information
-
kinetics in absence and presence of co-solvents, overview
-
additional information
additional information
-
kinetics of wild-type and mutant enzymes in presence or absence of CAPS and methylamine, overview
-
additional information
additional information
-
steady-state, transient state kinetics, and kinetic isotope effects, kinetic analysis and mechanism, ordered bi-bi mechanism, detailed overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.00063 - 0.85
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
0.115
(5beta,20R)-20-hydroxypregnan-3-one
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
54.5
3-oxo-deoxycholic acid
coenzyme: NADPH, pH 7.0, temperature not specified in the publication
-
0.008
3alpha-androstanediol
-
pH 7.0, 25°C, recombinant enzyme
1.13 - 1.25
3alpha-hydroxy-5alpha-androstan-17-one
0.148
4-oxo-2-nonenal
pH 7.4, 25°C
0.35
5alpha-androstan-17beta-ol-3-one
-
-
0.267 - 0.567
5alpha-androstan-3,17-dione
1.33
5alpha-androstan-3alpha,17beta-diol
-
-
2.72
5alpha-Androstan-3alpha-ol-17-one
-
-
0.42
5alpha-androstane-3,17-dione
-
pH 7.0, 25, reduction reaction
0.037 - 0.43
5alpha-dihydroprogesterone
0.033 - 1339
5alpha-dihydrotestosterone
0.767
5alpha-pregnan-21-ol-3,20-one
-
-
0.233
5alpha-Pregnan-3alpha,21-diol-20-one
-
-
0.45
5beta-androstan-3,17-dione
-
-
1.2
5beta-Androstan-3alpha,17beta-diol
-
-
1.33
5beta-Androstan-3alpha-ol-17-one
-
-
0.047
5beta-androstane-3,17-dione
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.433
5beta-Dihydrocortisone
-
-
0.417
5beta-pregnan-3,20-dione
-
-
0.633
5beta-Pregnan-3alpha,21-diol-20-one
-
-
0.767
5beta-Pregnan-3alpha-ol-20-one
-
-
0.105
5beta-pregnane-3,20-dione
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.1
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.183 - 3.93
9,10-phenanthrenequinone
0.0028 - 318
androsterone
0.022 - 0.733
Dehydrolithocholic acid
55.9
deoxycholic acid
coenzyme: NADP+, pH 10, temperature not specified in the publication
0.167
diacetyl
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.2
glycochenodeoxycholic acid
-
-
0.233
glycolithocholic acid
-
-
0.283
isatin
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.217
lithocholic acid
-
-
additional information
additional information
-
0.00063
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
cofactor NADP+, pH 7.0, 25°C, steroid oxidation, recombinant mutant W227A
0.37
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
cofactor NADP+, pH 7.0, 25°C, steroid oxidation, recombinant wild-type enzyme
0.8
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
cofactor NADP+, pH 7.0, 25°C, steroid oxidation, recombinant mutant R276M
0.85
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
-
cofactor NAD+, pH 7.0, 25°C, steroid oxidation, recombinant wild-type enzyme
1.13
3alpha-hydroxy-5alpha-androstan-17-one
-
Y205F
1.25
3alpha-hydroxy-5alpha-androstan-17-one
-
recombinant wild type enzyme
0.267
5alpha-androstan-3,17-dione
-
Y205F
0.283
5alpha-androstan-3,17-dione
-
recombinant wild type enzyme
0.567
5alpha-androstan-3,17-dione
-
-
0.037
5alpha-dihydroprogesterone
-
cofactor NADPH, pH 7.0, 25°C, steroid reduction, recombinant mutant W227A
0.3
5alpha-dihydroprogesterone
-
cofactor NADPH, pH 7.0, 25°C, steroid reduction, recombinant wild-type enzyme
0.4
5alpha-dihydroprogesterone
-
cofactor NADPH, pH 7.0, 25°C, steroid reduction, recombinant mutant R276M
0.43
5alpha-dihydroprogesterone
-
cofactor NADH, pH 7.0, 25°C, steroid reduction, recombinant wild-type enzyme
0.033
5alpha-dihydrotestosterone
-
pH 7.0, 25°C, recombinant enzyme
5.9
5alpha-dihydrotestosterone
pH 7.5, recombinant mutant R304L
22.1
5alpha-dihydrotestosterone
pH 7.5, recombinant mutant R301L
1339
5alpha-dihydrotestosterone
pH 7.5, recombinant wild-type enzyme
0.183
9,10-phenanthrenequinone
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
1.17 - 3.93
9,10-phenanthrenequinone
-
-
0.0028
androsterone
-
pH 9.0, 25°C, recombinant mutant S114A/Y155F
0.003
androsterone
-
pH 9.0, 25°C, recombinant mutant Y155F/K159A
0.0053
androsterone
-
steady-state, pH 8.0, 25°C, recombinant mutant W227A
0.0083
androsterone
-
steady-state, pH 8.0, 25°C, recombinant mutant F118A
0.12
androsterone
-
pH 9.0, 25°C, recombinant mutant S114A
0.57
androsterone
-
steady-state, pH 8.0, 25°C, recombinant mutant T226A
0.82
androsterone
-
pH 7.0, 25, oxidation reaction
0.83
androsterone
-
steady-state, pH 8.0, 25°C, recombinant wild-type enzyme
1.5
androsterone
-
pH 9.0, 25°C, recombinant mutant Y155F
18.9
androsterone
-
pH 9.0, 25°C, recombinant mutant K159A
318
androsterone
-
pH 9.0, 25°C, recombinant wild-type enzyme
0.022
Dehydrolithocholic acid
-
pH 7.4, 25°C, recombinant wild-type AKR1C17
0.733
Dehydrolithocholic acid
-
-
1.13
NAD+
-
recombinant wild type enzyme
0.283
NADH
-
recombinant wild type enzyme
additional information
additional information
-
kcat in steady-state, single turnover, burst in multiple turnover, steady-state in multiple turnover
-
additional information
additional information
-
single turnover, and multiple burst and steady-state in turnover, kinetic isotope effects with 4-pro-R-[2H]-NADPH on recombinant wild-type and mutant enzymes
-
additional information
additional information
-
cofactor kinetics of wild-type and mutant enzymes, overview
-
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K159M
-
site-directed mutagenesis, the mutation changes the rate-limiting step to the hydride transfer, proton transfer is blocked in the mutant but can be rescued using exogenous proton acceptors, such as buffers, small primary amines, and azide, overview
S114A
-
site-directed mutagenesis, altered kinetics in comparison to the wild-type enzyme
S114A/Y155F
-
site-directed mutagenesis, altered kinetics in comparison to the wild-type enzyme
Y155F
-
site-directed mutagenesis, altered kinetics in comparison to the wild-type enzyme
Y155F/K159A
-
site-directed mutagenesis, altered kinetics in comparison to the wild-type enzyme
H5Q
a naturally occuring non-synonymous single nucleotide polymorphism (SNP), rs12529 C>G or AKR1C3-2 in exon 1 of AKR1C3
R301L
site-directed mutagenesis, the mutation greatly affects the 3alpha-hydroxysteroid dehydrogenase activity towards 5alpha-dihydrotestosterone and almost completely abolishes the 17beta-hydroxysteroid dehydrogenase activity of the enzyme
R304L
site-directed mutagenesis, the mutation greatly affects the 3alpha-hydroxysteroid dehydrogenase activity towards 5alpha-dihydrotestosterone and abolishes the 17beta-hydroxysteroid dehydrogenase activity of the enzyme
C217A
-
resistant to inactivation by secosteroids, therefore Cys217 is the point of covalent attachment of acetylenic ketones
D50E
-
1/30th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
D50N
-
1/30th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
E276R
-
site-directed mutagenesis, the mutation alters the cofactor specificity of AKR1C17 from NAD+ to NADP+, the switch is analogy th the residues of AKRc9 and its cofactor specificity, overview
H117A
-
1/500th catalytic efficiency of wild type, unlikely to be the general amino acid for catalysis
K84M
-
inactive, unable to bind steroids
K84R
-
inactive, unable to bind steroids
N167A
site-directed mutagenesis, most impaired enzyme
Q190A
site-directed mutagenesis, decreased binding affinity to NADP(H), only binding of cofactor is affected, residue is located at the catalytic cente
Q270K
-
site-directed mutagenesis, the mutation alters the cofactor specificity of AKR1C17 from NAD+ to NADP+, the switch is analogy th the residues of AKRc9 and its cofactor specificity, overview
Q270K/E276R
-
site-directed mutagenesis, the mutation alters the cofactor specificity of AKR1C17 from NAD+ to NADP+, the switch is analogy th the residues of AKRc9 and its cofactor specificity, overview
R276E
-
site-directed mutagenesis, the mutant shows increased preference for the oxidation reaction compared to the wild-type enzyme
R276G
-
site-directed mutagenesis, the mutant shows slightly increased preference for the reduction reaction compared to the wild-type enzyme
S166A
site-directed mutagenesis, decreased binding affinity to NADP(H), only binding of cofactor is affected, residue is located at the catalytic center
Y205F
-
kinetically indistinguishable from the wild type, no general amino acid for catalysis in 3alpha-hydroxysteroid dehydrogenase
Y216S
site-directed mutagenesis, decreased binding affinity to NADP(H), only binding of cofactor is affected, residue is located at the catalytic cente
Y55F
-
inactive, unable to perform steroid oxidoreduction, strongest candidate for the general amino acid
Y55S
-
inactive, strongest candidate for the general amino acid
K159A
-
site-directed mutagenesis, altered kinetics in comparison to the wild-type enzyme
K159A
-
site-directed mutagenesis, the mutation changes the rate-limiting step to the hydride transfer, proton transfer is blocked in the mutant but can be rescued using exogenous proton acceptors, such as buffers, small primary amines, and azide, overview
F118A
-
site-directed mutagenesis, highly reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
F118A
largest changes in kcat/Km
F129A
-
site-directed mutagenesis, highly reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
F129A
largest changes in kcat/Km, F129A alters the stereochemical preference from oxidizing predominantly the S,S-stereoisomer to oxidizing predominantly the R,R-stereoisomer of benzo[g]chrysene-11,12-dihydrodiol
L54A
-
site-directed mutagenesis, reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
L54A
mutant shows intermediate changes in kcat/Km versus wild type
N306A
-
site-directed mutagenesis, reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
N306A
mutant shows intermediate changes in kcat/Km versus wild type
R276M
elimination of salt bridge between Arg276 and the 2'-phosphate of AMP results in 100fold decrease of the affinity to NADP(H)
R276M
-
site-directed mutagenesis, mutant does no longer form a salt-linkage to the phosphate of 2'-AMP, and does no longer bind tightly to NAD(P)H, the burst phase kinetics for the NADP+-dependent oxidation of 3alpha-diol is eliminated
R276M
-
site-directed mutagenesis, the mutant shows slightly increased preference for the reduction reaction compared to the wild-type enzyme
T226A
-
site-directed mutagenesis, reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
T226A
smallest change in kcat/Km is observed when alanine is used to substitute hydrophilic residues
T24A
-
site-directed mutagenesis, reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
T24A
smallest change in kcat/Km is observed when alanine is used to substitute hydrophilic residues
W148Y
-
site-directed mutagenesis, kinetically similar to wild type enzyme, no function in ligand binding
W148Y
-
can catalyse steroid oxidoreduction similar to wild type, plays no role in steroid binding or catalysis
W227A
-
site-directed mutagenesis, highly reduced activity compared to the wild-type enzyme, 23fold decreased affinity for progesterone, effects of mutation on binding constants and kinetics, overview
W227A
-
site-directed mutagenesis, highly reduced activity compared to the wild-type, very slow chemical transformation
W227A
largest changes in kcat/Km
W227Y
-
site-directed mutagenesis, important role in binding steroid hormones, but not small substrates or inhibitors, interacts with the C and/or D-rings of steroid ligand
W227Y
-
mainly influenced in steroid binding
W86Y
-
site-directed mutagenesis, important in binding steroids and non-steroidal anti-inflamatory drugs, region in which it resides is part of the substrate/inhibitor binding pocket, near the A-, and B-rings of bound steroid
W86Y
-
plays role in cofactor and steroid binding
Y310A
-
site-directed mutagenesis, reduced activity compared to the wild-type enzyme, effects of mutation on binding constants and kinetics, overview
Y310A
mutant shows intermediate changes in kcat/Km versus wild type
additional information
-
co-immobilization of the enzyme with diaphorase of Clostridum sp. onto alkylamine glass beads through glutaraldehyde coupling for determination of bile acids, method opimization and evaluation, loss of 30% of activity after 4 months of regular use, overview
additional information
-
construction of insertion mutants, overview
additional information
-
potential CoA binding sites spanning residues 182 to 193. N-terminal region is thought to contain the NAD(P)+ binding site, the middle and C-terminal regions the active site of the enzyme
additional information
-
potential CoA binding sites spanning residues 182 to 193. N-terminal region is thought to contain the NAD(P)+ binding site, the middle and C-terminal regions the active site of the enzyme
-
additional information
-
positions of Tyr/Lys pair are conserved across the aldo-keto reductase and short-chain dehydrogenase/reductase family. Tyr retains ability to form ternary complex and acts as general acid
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Ohmura, M.; Hara, A.; Nakagawa, M.; Sawada, H.
Demonstration of 3alpha(17beta)-hydroxysteroid dehydrogenase distinct from 3alpha-hydroxysteroid dehydrogenase in hamster liver
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1990
Mesocricetus auratus
brenda
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Kinetic and stereochemical characterization of hamster liver 3alpha-hydroxysteroid dehydrogenase and 3alpha(17beta)-hydroxysteroid dehydrogenase
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1991
Mesocricetus auratus
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The kinetic mechanism catalysed by homogeneous rat liver 3alpha-hydroxysteroid dehydrogenase. Evidence for binary and ternary dead-end complexes containing non-steroidal anti-inflammatory drugs
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Rattus norvegicus
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Cloning and sequencing of the cDNA for rat liver 3alpha-hydroxysteroid/dihydrodiol dehydrogenase
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A mammalian 3alpha-hydroxysteroid dehydrogenase
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Evidence that enzyme-generated aromatic Michael acceptors covalently modify the nucleotide-binding site of 3alpha-hydroxysteroid dehydrogenase
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Structure and function of 3alpha-hydroxysteroid dehydrogenase
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Rattus norvegicus
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Mutation of nicotinamide pocket residues in rat liver 3alpha-hydroxysteroid dehydrogenase reveals different modes of cofactor binding
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Rattus norvegicus (P23457)
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Dissection of the physiological interconversion of 5alpha-DHT and 3alpha-diol by rat 3alpha-HSD via transient kinetics shows that the chemical step is rate-determining: effect of mutating cofactor and substrate-binding pocket residues on catalysis
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43
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Rattus norvegicus
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Alanine scanning mutagenesis of the testosterone binding site of rat 3alpha-hydroxysteroid dehydrogenase demonstrates contact residues influence the rate-determining step
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43
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Multiplicity of mammalian reductases for xenobiotic carbonyl compounds
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21
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Mechanistic roles of Ser-114, Tyr-155, and Lys-159 in 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase from Comamonas testosteroni
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Multiple steps determine the overall rate of the reduction of 5alpha-dihydrotestosterone catalyzed by human type 3 3alpha-hydroxysteroid dehydrogenase: implications for the elimination of androgens
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45
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Homo sapiens
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Purification and characterization of rat liver enzyme catalyzing stereoselective reduction of acetylpyridines
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17
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2005
Rattus norvegicus
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Arginine 276 controls the directional preference of AKR1C9 (rat liver 3alpha-hydroxysteroid dehydrogenase) in human embryonic kidney 293 cells
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Comamonas testosteroni
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Tibolone metabolism in human liver is catalyzed by 3alpha/3beta-hydroxysteroid dehydrogenase activities of the four isoforms of the aldo-keto reductase (AKR)1C subfamily
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Dutasteride affects progesterone metabolizing enzyme activity/expression in human breast cell lines resulting in suppression of cell proliferation and detachment
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Isolation and characterization of a cDNA encoding mouse 3alpha-hydroxysteroid dehydrogenase: an androgen-inactivating enzyme selectively expressed in female tissues
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Identification of the major oxidative 3alpha-hydroxysteroid dehydrogenase in human prostate that converts 5alpha-androstane-3alpha,17beta-diol to 5alpha-dihydrotestosterone: a potential therapeutic target for androgen-dependent disease
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Rattus norvegicus (P23457)
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1970
Rattus norvegicus
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68
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Homo sapiens (P42330)
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Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3)
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Homo sapiens (P42330)
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Crystal structures of AKR1C3 containing an N-(aryl)amino-benzoate inhibitor and a bifunctional AKR1C3 inhibitor and androgen receptor antagonist. Therapeutic leads for castrate resistant prostate cancer
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5948-5951
2012
Homo sapiens (P42330)
brenda
Matsunaga, T.; Hojo, A.; Yamane, Y.; Endo, S.; El-Kabbani, O.; Hara, A.
Pathophysiological roles of aldo-keto reductases (AKR1C1 and AKR1C3) in development of cisplatin resistance in human colon cancers
Chem. Biol. Interact.
202
234-242
2013
Homo sapiens (P42330)
brenda
Heinrich, D.M.; Flanagan, J.U.; Jamieson, S.M.; Silva, S.; Rigoreau, L.J.; Trivier, E.; Raynham, T.; Turnbull, A.P.; Denny, W.A.
Synthesis and structure-activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3
Eur. J. Med. Chem.
62
738-744
2013
Homo sapiens (P42330)
brenda
Gazvoda, M.; Beranic, N.; Turk, S.; Burja, B.; Kocevar, M.; Rizner, T.L.; Gobec, S.; Polanc, S.
2,3-diarylpropenoic acids as selective non-steroidal inhibitors of type-5 17?-hydroxysteroid dehydrogenase (AKR1C3)
Eur. J. Med. Chem.
62
89-97
2013
Homo sapiens (P42330)
brenda
Zakharov, V.; Lin, H.K.; Azzarello, J.; McMeekin, S.; Moore, K.N.; Penning, T.M.; Fung, K.M.
Suppressed expression of type 2 3alpha/type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3) in endometrial hyperplasia and carcinoma
Int. J. Clin. Exp. Pathol.
3
608-617
2010
Homo sapiens (P42330)
brenda
Miller, V.L.; Lin, H.K.; Murugan, P.; Fan, M.; Penning, T.M.; Brame, L.S.; Yang, Q.; Fung, K.M.
Aldo-keto reductase family 1 member C3 (AKR1C3) is expressed in adenocarcinoma and squamous cell carcinoma but not small cell carcinoma
Int. J. Clin. Exp. Pathol.
5
278-289
2012
Homo sapiens
brenda
Brozic, P.; Turk, S.; Adeniji, A.O.; Konc, J.; Janezic, D.; Penning, T.M.; Lanisnik Rizner, T.; Gobec, S.
Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library
J. Med. Chem.
55
7417-7424
2012
Homo sapiens (P42330)
brenda
Byrns, M.C.; Mindnich, R.; Duan, L.; Penning, T.M.
Overexpression of aldo-keto reductase 1C3 (AKR1C3) in LNCaP cells diverts androgen metabolism towards testosterone resulting in resistance to the 5alpha-reductase inhibitor finasteride
J. Steroid Biochem. Mol. Biol.
130
7-15
2012
Homo sapiens (P42330)
brenda
Milivojevic, V.; Feinn, R.; Kranzler, H.R.; Covault, J.
Variation in AKR1C3, which encodes the neuroactive steroid synthetic enzyme 3alpha-HSD type 2 (17beta-HSD type 5), moderates the subjective effects of alcohol
Psychopharmacology
231
3597-3608
2014
Homo sapiens (P42330)
brenda
Mythen, S.; Devendran, S.; Mndez-Garca, C.; Cann, I.; Ridlon, J.
Targeted synthesis and characterization of a gene cluster encoding NAD(P)H-dependent 3alpha-, 3beta-, and 12alpha-hydroxysteroid dehydrogenases from Eggerthella CAG 298, a gut metagenomic sequence
Appl. Environ. Microbiol.
84
e02475-17
2018
Eggerthella sp. CAG:298 (R7B6R4)
brenda