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0.14 - 0.26
(S)-1,2,3,4-tetrahydronaphth-1-ol
0.146 - 0.52
(S)-indan-1-ol
1
2-(1-imidazolyl)-1-(4-methoxyphenyl)-2-methyl-1-propanone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.025 - 0.028
3-dehydro-alpha-ecdysone
0.035
3-dehydro-beta-ecdysone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0105
3alpha-androstanediol
isoform AKR1C4, at pH 7.4 and 25°C
0.0152 - 0.0216
3alpha-hydroxydesogestrel
0.00212
4-androstenedione
pH 7.4, 37°C
0.0023 - 0.03362
4-hydroxyandrostenedione
-
0.00603 - 0.02687
4-hydroxytestosterone
-
0.9 - 1
4-Nitroacetophenone
1 - 1.09
4-nitrobenzaldehyde
0.0001 - 0.003
5alpha-androstan-17-beta-ol-3-one
0.002 - 0.0022
5alpha-Androstan-3alpha-ol-17-one
0.00144
5alpha-androstane-3,17-dione
isoform AKR1C4, at pH 7.4 and 25°C
0.0008 - 0.0031
5alpha-androstane-3alpha,17beta-diol
0.0018
5alpha-dihydroprogesterone
in 100 mM potassium phosphate, pH 7.0, at 25°C
0.0012 - 0.07103
5alpha-dihydrotestosterone
0.0002 - 0.0003
5alpha-pregnan-20alpha-ol-3-one
0.0006 - 0.003
5beta-androstan-3,17-dione
0.0006 - 0.0021
5beta-Androstan-3alpha-ol-17-one
0.0012 - 0.0022
5beta-androstane-3alpha,17beta-diol
0.0111 - 0.0201
5beta-dihydrotestosterone
0.0005 - 0.0023
5beta-pregnane-3,20-dione
0.001
5beta-pregnane-3alpha,20alpha-diol
0.208 - 0.22
9alpha,11beta-prostaglandin F2
0.0015
allopregnanolone
in 100 mM potassium phosphate, pH 7.0, at 25°C
0.0328
androstandiol
pH 8.9, temperature not specified in the publication, NAD(P)+
0.0357
androstandione
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0012
androstenol
reombinant His-tagged enzyme, pH 10.5, 25°C
0.0011 - 0.0029
chenodeoxycholic acid
51 - 2489
Dehydrocholic acid
0.0009 - 0.004
Dehydrolithocholic acid
0.0013 - 0.0097
deoxycholic acid
0.0011 - 0.016
dihydrotestosterone
0.0207
epiandrosterone
pH 8.9, temperature not specified in the publication, NAD(P)+
0.003 - 0.0068
Fusidic acid
0.001 - 0.0019
lithocholic acid
2.1
metyrapol
pH 8.9, temperature not specified in the publication, NAD(P)+
0.033
NADH
mutant F217S, pH 7.4, 25°C
0.00084 - 0.00213
pregn-4-en-3,20-dione
additional information
additional information
-
0.16
(R)-tetralol
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.38
(R)-tetralol
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.68
(R)-tetralol
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.14
(S)-1,2,3,4-tetrahydronaphth-1-ol
-
recombinant enzyme, at pH 7.4 and 25°C
0.26
(S)-1,2,3,4-tetrahydronaphth-1-ol
-
native enzyme, at pH 7.4 and 25°C
0.146
(S)-indan-1-ol
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.28
(S)-indan-1-ol
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.42
(S)-indan-1-ol
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.49
(S)-indan-1-ol
-
recombinant enzyme, at pH 7.4 and 25°C
0.52
(S)-indan-1-ol
-
native enzyme, at pH 7.4 and 25°C
0.11
(S)-tetralol
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.24
(S)-tetralol
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.29
(S)-tetralol
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.16
2-decalol
pH 10.5, 40°C
0.6
2-decalol
reombinant His-tagged enzyme, pH 10.5, 25°C
1.7
2-decalol
pH 10.5, 10°C
0.025
3-dehydro-alpha-ecdysone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.028
3-dehydro-alpha-ecdysone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0152
3alpha-hydroxydesogestrel
pH 8.9, temperature not specified in the publication, NAD(P)+
0.0216
3alpha-hydroxydesogestrel
pH 8.9, temperature not specified in the publication, NAD(P)+
0.0023
4-hydroxyandrostenedione
pH 7.4, 37°C
-
0.00843
4-hydroxyandrostenedione
pH 7.4, 37°C
-
0.00977
4-hydroxyandrostenedione
pH 7.4, 37°C
-
0.03362
4-hydroxyandrostenedione
pH 7.4, 37°C
-
0.00603
4-hydroxytestosterone
pH 7.4, 37°C
-
0.00622
4-hydroxytestosterone
pH 7.4, 37°C
-
0.02687
4-hydroxytestosterone
pH 7.4, 37°C
-
0.9
4-Nitroacetophenone
pH 7.0, temperature not specified in the publication, NAD(P)H
1
4-Nitroacetophenone
pH 7.0, temperature not specified in the publication, NAD(P)H
1
4-nitrobenzaldehyde
pH 7.0, temperature not specified in the publication, NAD(P)H
1.09
4-nitrobenzaldehyde
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0001
5alpha-androstan-17-beta-ol-3-one
mutant F217S, pH 7.4, 25°C
0.003
5alpha-androstan-17-beta-ol-3-one
wild-type, pH 7.4, 25°C
0.002
5alpha-Androstan-3alpha-ol-17-one
-
native enzyme, at pH 7.4 and 25°C
0.0022
5alpha-Androstan-3alpha-ol-17-one
-
recombinant enzyme, at pH 7.4 and 25°C
0.0008
5alpha-androstane-3alpha,17beta-diol
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0026
5alpha-androstane-3alpha,17beta-diol
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0031
5alpha-androstane-3alpha,17beta-diol
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0012
5alpha-dihydrotestosterone
apparent Km-value, pH 7.4, 37°C
0.00218
5alpha-dihydrotestosterone
pH 7.4, 37°C, recombinant wild-type enzyme
0.0034
5alpha-dihydrotestosterone
isoform AKR1C4, at pH 7.4 and 25°C
0.0161
5alpha-dihydrotestosterone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.019
5alpha-dihydrotestosterone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0192
5alpha-dihydrotestosterone
apparent Km-value, pH 7.4, 37°C
0.07103
5alpha-dihydrotestosterone
pH 7.4, 37°C, recombinant mutant V54L
0.0002
5alpha-pregnan-20alpha-ol-3-one
mutant F217S, pH 7.4, 25°C
0.0003
5alpha-pregnan-20alpha-ol-3-one
wild-type, pH 7.4, 25°C
0.0006
5beta-androstan-3,17-dione
mutant F217S, pH 7.4, 25°C
0.003
5beta-androstan-3,17-dione
wild-type, pH 7.4, 25°C
0.0006
5beta-Androstan-3alpha-ol-17-one
mutant F217S, pH 7.4, 25°C
0.0009
5beta-Androstan-3alpha-ol-17-one
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0014
5beta-Androstan-3alpha-ol-17-one
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0018
5beta-Androstan-3alpha-ol-17-one
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0021
5beta-Androstan-3alpha-ol-17-one
wild-type, pH 7.4, 25°C
0.0012
5beta-androstane-3alpha,17beta-diol
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0021
5beta-androstane-3alpha,17beta-diol
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0022
5beta-androstane-3alpha,17beta-diol
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0111
5beta-dihydrotestosterone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0201
5beta-dihydrotestosterone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.0005
5beta-pregnane-3,20-dione
mutant F217S, pH 7.4, 25°C
0.0023
5beta-pregnane-3,20-dione
wild-type, pH 7.4, 25°C
0.001
5beta-pregnane-3alpha,20alpha-diol
-
native enzyme, at pH 7.4 and 25°C
0.001
5beta-pregnane-3alpha,20alpha-diol
-
recombinant enzyme, at pH 7.4 and 25°C
0.208
9alpha,11beta-prostaglandin F2
-
native enzyme, at pH 7.4 and 25°C
0.22
9alpha,11beta-prostaglandin F2
-
recombinant enzyme, at pH 7.4 and 25°C
0.0005
androsterone
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0022
androsterone
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0027
androsterone
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0028
androsterone
reombinant His-tagged enzyme, pH 10.5, 25°C
0.00504
androsterone
isoform AKR1C4, at pH 7.4 and 25°C
0.0244
androsterone
pH 8.9, temperature not specified in the publication, NAD(P)+
0.0267
androsterone
pH 8.9, temperature not specified in the publication, NAD(P)+
14
androsterone
pH 10.5, 40°C
0.0011
chenodeoxycholic acid
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0023
chenodeoxycholic acid
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0029
chenodeoxycholic acid
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.025
cholic acid
pH 8.9, temperature not specified in the publication, NAD(P)+
0.0301
cholic acid
pH 8.9, temperature not specified in the publication, NAD(P)+
0.032
cholic acid
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.041
cholic acid
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.059
cholic acid
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
56
cholic acid
-
recombinant His-tagged wild-type enzyme, pH 8.0, 37°C
78
cholic acid
-
recombinant His-tagged mutant S114A/Y153F, pH 8.0, 37°C
96
cholic acid
-
recombinant His-tagged mutant K157A, pH 8.0, 37°C
468
cholic acid
-
recombinant His-tagged mutant Y153F, pH 8.0, 37°C
586
cholic acid
-
recombinant His-tagged mutant S114A, pH 8.0, 37°C
27
Cyclohexanol
reombinant His-tagged enzyme, pH 10.5, 25°C
48
Cyclohexanol
pH 10.5, 40°C
51
Dehydrocholic acid
-
recombinant His-tagged wild-type enzyme, pH 8.0, 37°C
239
Dehydrocholic acid
-
recombinant His-tagged mutant S114A, pH 8.0, 37°C
2489
Dehydrocholic acid
-
recombinant His-tagged mutant Y153F, pH 8.0, 37°C
0.0009
Dehydrolithocholic acid
mutant F217S, pH 7.4, 25°C
0.004
Dehydrolithocholic acid
wild-type, pH 7.4, 25°C
0.0013
deoxycholic acid
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0014
deoxycholic acid
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0097
deoxycholic acid
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0011
dihydrotestosterone
pH 7.5, 37°C
0.00311
dihydrotestosterone
-
pH 7.2, 37°C, recombinant enzyme
0.00342
dihydrotestosterone
pH 7.2, 37°C, recombinant enzyme
0.00884
dihydrotestosterone
pH 7.4, 37°C
0.01029
dihydrotestosterone
pH 7.4, 37°C
0.0117
dihydrotestosterone
pH 7.4, 37°C
0.016
dihydrotestosterone
pH 7.4, 37°C
0.003
Fusidic acid
pH 8.9, temperature not specified in the publication, NAD(P)+
0.0061
Fusidic acid
pH 8.9, temperature not specified in the publication
0.0068
Fusidic acid
pH 8.9, temperature not specified in the publication, NAD(P)+
0.001
lithocholic acid
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0018
lithocholic acid
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0019
lithocholic acid
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.61
Metyrapone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.63
Metyrapone
pH 7.0, temperature not specified in the publication, NAD(P)H
0.081
NAD+
mutant F217S, pH 7.4, 25°C
0.14
NAD+
reombinant His-tagged enzyme, pH 10.5, 25°C, with androstenol
0.39
NAD+
reombinant His-tagged enzyme, pH 10.5, 25°C, with androsterone
0.97
NAD+
wild-type, pH 7.4, 25°C
1
NAD+
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
1
NAD+
mutant N272T, pH 7.4, 25°C
1.2
NAD+
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
1.2
NAD+
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0002
NADP+
mutant F217S, pH 7.4, 25°C
0.00023
NADP+
in 100 mM potassium phosphate, pH 7.0, at 25°C
0.0005
NADP+
-
mutant enzyme H216Y, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0006
NADP+
-
mutant enzyme H216F, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.0017
NADP+
-
wild type enzyme, in 0.1 M potassium phosphate, pH 7.4, at 25°C
0.017
NADP+
wild-type, pH 7.4, 25°C
0.017
NADP+
mutant N272T, pH 7.4, 25°C
0.00007
NADPH
in 100 mM potassium phosphate, pH 7.0, at 25°C
0.0004
NADPH
mutant F217S, pH 7.4, 25°C
0.0084
NADPH
wild-type, pH 7.4, 25°C
0.009
NADPH
mutant N272T, pH 7.4, 25°C
0.00084
pregn-4-en-3,20-dione
pH 7.4, 37°C, recombinant wild-type enzyme
0.00213
pregn-4-en-3,20-dione
pH 7.4, 37°C, recombinant mutant V54L
additional information
additional information
steady-state kinetics
-
additional information
additional information
-
steady-state kinetics
-
additional information
additional information
Km-value for the 17beta-oxidation of testosterone is 0.00067 mM, and Km-value for the 17beta-reduction of androstenedione is 0.00138 mM
-
additional information
additional information
steady-state kinetics, and stopped-flow study, kinetics of enzyme mutants P185A, P185G, T188A, and T188S showing an increase in kcat, Ka drosterone and KiNAD and equal primary isotope effects of DV and D(V/K)
-
additional information
additional information
steady-state kinetics of 3alpha-HSD/CR catalyzed reaction of NADþ with androsterone and the truncated analogues, overview. The uniform binding energy from the B-ring of steroids with the active site of 3alpha-HSD/CR equally contributes 2.1 kcal/mol to stabilize both the transition state and ground state of the ternary complex, leading to the similarity in kcat for 2-decalol and cyclohexanol. Differential binding interactions of the remote BCD-ring and CD-ring of androsterone with the active site of 3alpha-HSD/CR contribute 8.5 and 6.4 kcal/mol to the stabilization of the transition state, respectively. The removal of the carbonyl group at C17 of androsterone has small effects on catalysis. Both uniform and differential binding energies from the remote sites of androsterone compared to cyclohexanol contribute to the 3a-HSD/CR catalysis, resulting in the increases in kcat and kcat/KB
-
additional information
additional information
AKR1C isozymes kinetics analysis, steady-state Michaelis-Menten kinetics
-
additional information
additional information
AKR1C isozymes kinetics analysis, steady-state Michaelis-Menten kinetics
-
additional information
additional information
AKR1C isozymes kinetics analysis, steady-state Michaelis-Menten kinetics
-
additional information
additional information
AKR1C isozymes kinetics analysis, steady-state Michaelis-Menten kinetics
-
additional information
additional information
steady-state kinetics and thermodynamics. The effects of temperature on kcat/Km for 3alpha-HSD/CR acting on androsterone, 2-decalol, and cyclohexanol show the reactions are entropically favorable but enthalpically unfavorable. Thermodynamic analysis from the temperature-dependent values of Km and kcat shows the binding of the E-NAD+ complex with either 2-decalol or cyclohexanol to form the ternary complex is endothermic and entropy-driven, and the subsequent conversion to the transition state is both enthalpically and entropically unfavorable
-