Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 1.1.1.239 extracted from

  • Endo, S.; Matsunaga, T.; Fujimoto, A.; Kumada, S.; Arai, Y.; Miura, Y.; Mikamo, H.; El-Kabbani, O.; Yamano, S.; Iinuma, M.; Hara, A.
    Characterization of rabbit morphine 6-dehydrogenase and two NAD+-dependent 3alpha(17beta)-hydroxysteroid dehydrogenases (2013), Arch. Biochem. Biophys., 529, 131-139.
    View publication on PubMed
Search for more literature for 1.1.1.239

Cloned(Commentary)

Cloned (Comment) Organism
gene AKR1C26, DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)pLysS Oryctolagus cuniculus
gene AKR1C27, DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain BL21(DE3)pLysS Oryctolagus cuniculus
gene AKR1C28, DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21 (DE3) pLysS Oryctolagus cuniculus
gene AKR1C28, DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) pLysS Oryctolagus cuniculus
gene PGER6, DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain BL21 (DE3) pLysS Oryctolagus cuniculus

Protein Variants

Protein Variants Comment Organism
F310I site-directed mutagenesis Oryctolagus cuniculus
F310I site-directed mutagenesis, the mutant shows altered kinetic and substrate specificity compared to the wild-type enzyme Oryctolagus cuniculus
additional information a double mutation Y118F/F310I in AKR1C27 converts AKR1C27 to an enzyme with almost the same substrate specificity and inhibitor sensitivity as those of AKR1C28, overview Oryctolagus cuniculus
Y118F site-directed mutagenesis Oryctolagus cuniculus
Y118F site-directed mutagenesis, the mutant shows altered kinetic and substrate specificity compared to the wild-type enzyme Oryctolagus cuniculus
Y118F/F310I site-directed mutagenesis of Tyr118 and Phe310 in AKR1C27 to the corresponding residues (Phe and Ile, respectively) in AKR1C28 produces an enzyme that is similar to AKR1C28, suggesting their key roles in ligand binding Oryctolagus cuniculus
Y118F/F310I site-directed mutagenesis, the mutant shows altered kinetic and substrate specificity compared to the wild-type enzyme. The double mutation converts AKR1C27 to an enzyme with almost the same substrate specificity and inhibitor sensitivity as those of AKR1C28 Oryctolagus cuniculus

Inhibitors

Inhibitors Comment Organism Structure
Hexestrol competitive; competitive Oryctolagus cuniculus
hinokitiol competitive; competitive Oryctolagus cuniculus
icarisid II
-
 Oryctolagus cuniculus
ikarisoside A competitive; competitive Oryctolagus cuniculus
kaempferol
-
 Oryctolagus cuniculus
noranhydroicaritin
-
 Oryctolagus cuniculus
Phenolphthalein
-
 Oryctolagus cuniculus
quercetin
-
 Oryctolagus cuniculus
quercitrin
-
 Oryctolagus cuniculus
zearalenone competitive; competitive Oryctolagus cuniculus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
 additional information Michaelis-Menten kinetics Oryctolagus cuniculus
additional information
-
 additional information Michaelis-Menten kinetics of wild-type and mutant enzymes, overview Oryctolagus cuniculus
0.0001
-
 9,10-phenanthrenequinone pH 7.4, 25°C Oryctolagus cuniculus
0.0002
-
 9,10-phenanthrenequinone pH 7.4, 25°C Oryctolagus cuniculus
0.0005
-
 isatin pH 7.4, 25°C Oryctolagus cuniculus
0.0005
-
 5alpha-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.0006
-
 beta-ionol pH 7.4, 25°C Oryctolagus cuniculus
0.00067
-
 5alpha-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.00067
-
 5beta-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.00067
-
 5alpha-pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0007
-
 geranylgeraniol pH 7.4, 25°C Oryctolagus cuniculus
0.00074
-
 farnesol pH 7.4, 25°C Oryctolagus cuniculus
0.0008
-
 isatin pH 7.4, 25°C Oryctolagus cuniculus
0.0008
-
 1-phenyl-1,2-propanedione pH 7.4, 25°C Oryctolagus cuniculus
0.00083
-
 geranylgeraniol pH 7.4, 25°C Oryctolagus cuniculus
0.0011
-
 isatin pH 7.4, 25°C Oryctolagus cuniculus
0.0015
-
 5beta-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.00167
-
 testosterone pH 7.4, 25°C Oryctolagus cuniculus
0.0019
-
 (S)-camphorquinone pH 7.4, 25°C Oryctolagus cuniculus
0.0021
-
 17beta-estradiol pH 7.4, 25°C Oryctolagus cuniculus
0.0021
-
 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one pH 7.4, 25°C Oryctolagus cuniculus
0.0021
-
 16-oxoestrone pH 7.4, 25°C Oryctolagus cuniculus
0.0022
-
 5alpha-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.0022
-
 5beta-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.0023
-
 5beta-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.0025
-
 farnesol pH 7.4, 25°C Oryctolagus cuniculus
0.0026
-
 NADH pH 7.4, 25°C Oryctolagus cuniculus
0.0029
-
 (S)-camphorquinone pH 7.4, 25°C Oryctolagus cuniculus
0.003
-
 1-phenyl-1,2-propanedione pH 7.4, 25°C Oryctolagus cuniculus
0.003
-
 16-oxoestrone pH 7.4, 25°C Oryctolagus cuniculus
0.0035
-
 5alpha-pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0036
-
 5beta-Pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0037
-
 5beta-Pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0038
-
 alpha-tetralone pH 7.4, 25°C Oryctolagus cuniculus
0.004
-
 (S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C Oryctolagus cuniculus
0.0042
-
 geraniol pH 7.4, 25°C Oryctolagus cuniculus
0.0042
-
 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one pH 7.4, 25°C Oryctolagus cuniculus
0.0043
-
 NADH pH 7.4, 25°C Oryctolagus cuniculus
0.005
-
 1-phenyl-1,2-propanedione pH 7.4, 25°C Oryctolagus cuniculus
0.0057
-
 4-pregnen-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0067
-
 (S)-camphorquinone pH 7.4, 25°C Oryctolagus cuniculus
0.0073
-
 4-pregnen-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0076
-
 5beta-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.0078
-
 5alpha-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.0078
-
 5alpha-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.009
-
 beta-ionol pH 7.4, 25°C Oryctolagus cuniculus
0.0092
-
 5alpha-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.0096
-
 NAD+ pH 7.4, 25°C Oryctolagus cuniculus
0.01
-
 16-oxoestrone pH 7.4, 25°C Oryctolagus cuniculus
0.012
-
 NAD+ pH 7.4, 25°C Oryctolagus cuniculus
0.012
-
 geraniol pH 7.4, 25°C Oryctolagus cuniculus
0.012
-
 lithocholic acid pH 7.4, 25°C Oryctolagus cuniculus
0.014
-
 (S)-1-indanol pH 7.4, 25°C Oryctolagus cuniculus
0.02
-
 NAD+ pH 7.4, 25°C Oryctolagus cuniculus
0.02
-
 5beta-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.022
-
 (S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C Oryctolagus cuniculus
0.027
-
 benzene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.027
-
 Naphthalene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.03
-
 5beta-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.033
-
 NADH pH 7.4, 25°C Oryctolagus cuniculus
0.035
-
 2-Cyclohexen-1-ol pH 7.4, 25°C Oryctolagus cuniculus
0.037
-
 testosterone pH 7.4, 25°C Oryctolagus cuniculus
0.042
-
 (S)-1-indanol pH 7.4, 25°C Oryctolagus cuniculus
0.06
-
 alpha-tetralone pH 7.4, 25°C Oryctolagus cuniculus
0.066
-
 2-Cyclohexen-1-ol pH 7.4, 25°C Oryctolagus cuniculus
0.081
-
 4-pregnen-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.1
-
 17beta-estradiol pH 7.4, 25°C Oryctolagus cuniculus
0.101
-
 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one pH 7.4, 25°C Oryctolagus cuniculus
0.11
-
 (S)-1-indanol pH 7.4, 25°C Oryctolagus cuniculus
0.12
-
 benzene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.13
-
 5alpha-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.14
-
 lithocholic acid pH 7.4, 25°C Oryctolagus cuniculus
0.15
-
 alpha-tetralone pH 7.4, 25°C Oryctolagus cuniculus
0.17
-
 5beta-Pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.19
-
 2,3-Butanedione pH 7.4, 25°C Oryctolagus cuniculus
0.21
-
 2,3-Butanedione pH 7.4, 25°C Oryctolagus cuniculus
0.25
-
 testosterone pH 7.4, 25°C Oryctolagus cuniculus
0.25
-
 (S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C Oryctolagus cuniculus
0.29
-
 Pyridine-3-aldehyde pH 7.4, 25°C Oryctolagus cuniculus
0.3
-
 Pyridine-3-aldehyde pH 7.4, 25°C Oryctolagus cuniculus
0.371
-
 2,3-Butanedione pH 7.4, 25°C Oryctolagus cuniculus
0.52
-
 morphine pH 7.4, 25°C Oryctolagus cuniculus
0.57
-
 geraniol pH 7.4, 25°C Oryctolagus cuniculus
0.67
-
 2-Cyclohexen-1-ol pH 7.4, 25°C Oryctolagus cuniculus
1.1
-
 Pyridine-3-aldehyde pH 7.4, 25°C Oryctolagus cuniculus
1.11
-
 benzene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
testosterone + NAD+ Oryctolagus cuniculus
-
 androstenedione + NADH + H+
-
 r

Organism

Organism UniProt Comment Textmining
Oryctolagus cuniculus G1T465
-
-
Oryctolagus cuniculus J7M9D0
-
-
Oryctolagus cuniculus J7MBS9
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3) pLysS by nickel affinity chromatography, ultrafiltration, and dialysis Oryctolagus cuniculus
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli strain BL21 (DE3) pLysS by nickel affinity chromatography, ultrafiltration, and dialysis Oryctolagus cuniculus

Source Tissue

Source Tissue Comment Organism Textmining
adrenal gland high expression level of AKR1C26 Oryctolagus cuniculus
-
colon high expression level of AKR1C27 Oryctolagus cuniculus
-
colon high expression level of AKR1C28 Oryctolagus cuniculus
-
kidney high expression level of AKR1C26 Oryctolagus cuniculus
-
liver high expression level of AKR1C26 Oryctolagus cuniculus
-
liver low expression level of AKR1C27 Oryctolagus cuniculus
-
additional information ubiquitous expression in rabbit tissues Oryctolagus cuniculus
-
small intestine high expression level of AKR1C28 Oryctolagus cuniculus
-
stomach high expression level of AKR1C26 Oryctolagus cuniculus
-
testis high expression level of AKR1C26 Oryctolagus cuniculus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+ i.e. (S)-tetralol Oryctolagus cuniculus 3,4-dihydronaphthalen-1(2H)-one + NADH + H+
-
 ?
(S)-1-indanol + NAD+
-
 Oryctolagus cuniculus 2,3-dihydro-1H-inden-1-one + NADH + H+
-
 ?
(S)-camphorquinone + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
1-phenyl-1,2-propanedione + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
16-oxoestrone + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
17beta-estradiol + NAD+
-
 Oryctolagus cuniculus estrone + NADH + H+
-
 ?
17beta-estradiol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 r
2,3-butanedione + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
2-cyclohexen-1-ol + NAD+
-
 Oryctolagus cuniculus 2-cyclohexen-1-one + NADH + H+
-
 ?
4-pregnen-3alpha-ol-2-one + NAD+
-
 Oryctolagus cuniculus 4-pregnen-3,20-dione + NADH + H+
-
 r
4-pregnen-3alpha-ol-20-one + NAD+
-
 Oryctolagus cuniculus 4-pregnen-3,20-dione + NADH + H+
-
 ?
5alpha-androstan-17beta-ol-3-one + NAD+
-
 Oryctolagus cuniculus 5alpha-androstan-3,17-dione + NADH + H+
-
 ?
5alpha-androstan-3alpha-ol-17-one + NAD+
-
 Oryctolagus cuniculus 5alpha-androstan-3,17-dione + NADH + H+
-
 ?
5alpha-androstan-3alpha-ol-17-one + NAD+
-
 Oryctolagus cuniculus 5alpha-androstan-3,17-dione + NADH + H+
-
 r
5alpha-androstane-17beta-ol-3-one + NAD+
-
 Oryctolagus cuniculus 5alpha-androstan-3,17-dione + NADH + H+
-
 r
5alpha-androstane-3,17-dione + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
5alpha-androstane-3alpha,17beta-diol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
5alpha-androstane-3alpha,17beta-diol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 r
5alpha-pregnan-3alpha-ol-20-one + NAD+
-
 Oryctolagus cuniculus 5alpha-pregnan-3,20-dione + NADH + H+
-
 ?
5alpha-pregnan-3alpha-ol-20-one + NAD+
-
 Oryctolagus cuniculus 5alpha-pregnan-3,20-dione + NADH + H+
-
 r
5beta-androstan-17beta-ol-3-one + NAD+
-
 Oryctolagus cuniculus 5beta-androstan-3,17-dione + NADH + H+
-
 ?
5beta-androstan-3alpha-ol-17-one + NAD+
-
 Oryctolagus cuniculus 5beta-androstan-3,17-dione + NADH + H+
-
 ?
5beta-androstan-3alpha-ol-17-one + NAD+
-
 Oryctolagus cuniculus 5beta-androstan-3,17-dione + NADH + H+
-
 r
5beta-androstane-17beta-ol-3-one + NAD+
-
 Oryctolagus cuniculus 5beta-androstan-3,17-dione + NADH + H+
-
 r
5beta-androstane-3,17-dione + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
5beta-androstane-3alpha,17beta-diol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
5beta-androstane-3alpha,17beta-diol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 r
5beta-pregnan-3alpha-ol-20-one + NAD+
-
 Oryctolagus cuniculus 5beta-pregnan-3,20-dione + NADH + H+
-
 ?
5beta-pregnan-3alpha-ol-20-one + NAD+
-
 Oryctolagus cuniculus 5beta-pregnan-3,20-dione + NADH + H+
-
 r
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
9,10-phenanthrenequinone + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
alpha-tetralone + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
benzene dihydrodiol + NAD+
-
 Oryctolagus cuniculus ?
-
 ?
benzene dihydrodiol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
beta-ionol + NAD+
-
 Oryctolagus cuniculus (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
 ?
farnesol + NAD+
-
 Oryctolagus cuniculus ?
-
 ?
farnesol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
geraniol + NAD+
-
 Oryctolagus cuniculus ?
-
 ?
geraniol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
geranylgeraniol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
geranylgeraniol + NAD+
-
 Oryctolagus cuniculus ?
-
 ?
isatin + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
lithocholic acid
-
 Oryctolagus cuniculus 5beta-cholan-3-one-24-oic acid + NADH + H+
-
 ?
lithocholic acid + NAD+
-
 Oryctolagus cuniculus 5-beta-cholan-3-one-24-oic acid + NADH + H+
-
 ?
lithocholic acid + NAD+
-
 Oryctolagus cuniculus 5beta-cholan-3-one-24-oic acid + NADH + H+
-
 ?
additional information residues Tyr118 and Phe310 play key roles in ligand binding in AKR1C27 and AKR1C28, Glu276 that is a critical residue for the NAD+ specificity is conserved in the enzymes. In the reverse reaction, the enzymes reduces several a-dicarbonyl compounds including scamphorquinone using NADH as the coenzyme. The enzyme oxidizes 3alpha- and 17beta-hydroxysteroids and also shows S-tetralol dehydrogenase activity, cf. EC 1.1.1.121 and (S)-specific secondary alcohol dehydrogenase. AKR1C28 exhibits low dehydrogenase activity for 20alpha-hydroxysteroids, but does not oxidize 3beta-hydroxysteroids (5alpha/beta-androstan-3beta-ol-17-ones and 5alpha/beta-pregnan-3beta-ol-20-ones), 17alpha-hydroxysteroids (4-androsten-17alpha-ol-3-one and 17alpha-estradiol) and 20beta-hydroxysteroids (4-pregnene-17alpha/20beta-diol-3-one and 5alpha-pregnan-20beta-ol-3-one). In the NADH-linked reverse reaction, AKR1C28 highly reduces non-steroidal alpha-dicarbonyl compounds, and also exhibits moderate activities towards TBE, alpha-tetralone and pyridine-3-aldehyde. AKR1C28 shows higher kcat/Km values for 17beta-hydroxy-C19-steroids than those for 3alpha-hydroxysteroids, and most efficiently oxidized 17beta-estradiol. Substrate specificity, overview Oryctolagus cuniculus ?
-
 ?
additional information residues Tyr118 and Phe310 play key roles in ligand binding in AKR1C27 and AKR1C28, Glu276 that is a critical residue for the NAD+ specificity is conserved in the enzymes. In the reverse reaction, the enzymes reduces several a-dicarbonyl compounds including scamphorquinone using NADH as the coenzyme. The enzyme oxidizes 3alpha- and 17beta-hydroxysteroids and also shows S-tetralol dehydrogenase activity, cf. EC 1.1.1.121 and (S)-specific secondary alcohol dehydrogenase. In the NADH-linked reverse reaction, AKR1C27 highly reduces non-steroidal alpha-dicarbonyl compounds, and also exhibits moderate activities towards TBE, alpha-tetralone and pyridine-3-aldehyde. Substrate specificity, detailed overview Oryctolagus cuniculus ?
-
 ?
additional information the enzyme show NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids. No or poor activity with naphthalene dihydrodiol, morphine, and 5alpha-pregnan-20alpha-ol-3-one Oryctolagus cuniculus ?
-
 ?
additional information the enzyme show NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids. No or poor activity with naphthalene dihydrodiol, morphine, beta-ionol, geraniogeraniol, farnesol, 5alpha-androstane-3alpha,17beta-diol, 5alpha-pregnan-20alpha-ol-3-one, and 4-pregnen-20alpha-3-one Oryctolagus cuniculus ?
-
 ?
additional information the enzyme shows NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids Oryctolagus cuniculus ?
-
 ?
morphine + NAD+ reaction of EC 1.1.1.218 Oryctolagus cuniculus morphinone + NADH + H+
-
 ?
naphthalene dihydrodiol + NAD+
-
 Oryctolagus cuniculus ? + NADH + H+
-
 ?
pyridine-3-aldehyde + NADH + H+
-
 Oryctolagus cuniculus ? + NAD+
-
 ?
testosterone + NAD+
-
 Oryctolagus cuniculus androstenedione + NADH + H+
-
 r
testosterone + NAD+
-
 Oryctolagus cuniculus 4-androstenedione + NADH + H+
-
 ?
testosterone + NADP+
-
 Oryctolagus cuniculus androstenedione + NADPH + H+
-
 r

Synonyms

Synonyms Comment Organism
3alpha(17beta)-hydroxysteroid dehydrogenase
-
 Oryctolagus cuniculus
AKR1C26
-
 Oryctolagus cuniculus
AKR1C27
-
 Oryctolagus cuniculus
AKR1C28
-
 Oryctolagus cuniculus
More cf. EC 1.1.1.218 Oryctolagus cuniculus
NAD+-dependent 3alpha(17beta)-hydroxysteroid dehydrogenase
-
 Oryctolagus cuniculus
NAD+-dependent 3beta(17beta)-hydroxysteroid dehydrogenase
-
 Oryctolagus cuniculus
NAD+-linked S-tetralol dehydrogenase
-
 Oryctolagus cuniculus
PGER6
-
 Oryctolagus cuniculus
PGER6 UniProt Oryctolagus cuniculus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Oryctolagus cuniculus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.00067
-
 lithocholic acid pH 7.4, 25°C Oryctolagus cuniculus
0.0008
-
 geranylgeraniol pH 7.4, 25°C Oryctolagus cuniculus
0.0012
-
 5alpha-pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0014
-
 4-pregnen-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.002
-
 5beta-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.0023
-
 5beta-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.0027
-
 5alpha-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.0032
-
 5beta-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.0032
-
 4-pregnen-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0033
-
 5alpha-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.004
-
 NAD+ pH 7.4, 25°C Oryctolagus cuniculus
0.004
-
 5beta-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.005
-
 5beta-Pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0052
-
 5alpha-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.0055
-
 farnesol pH 7.4, 25°C Oryctolagus cuniculus
0.0063
-
 17beta-estradiol pH 7.4, 25°C Oryctolagus cuniculus
0.0072
-
 5alpha-pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0074
-
 5beta-Pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0075
-
 beta-ionol pH 7.4, 25°C Oryctolagus cuniculus
0.0079
-
 testosterone pH 7.4, 25°C Oryctolagus cuniculus
0.0082
-
 testosterone pH 7.4, 25°C Oryctolagus cuniculus
0.0103
-
 5alpha-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.012
-
 4-pregnen-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.0122
-
 5beta-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.0127
-
 geranylgeraniol pH 7.4, 25°C Oryctolagus cuniculus
0.0143
-
 alpha-tetralone pH 7.4, 25°C Oryctolagus cuniculus
0.015
-
 geraniol pH 7.4, 25°C Oryctolagus cuniculus
0.015
-
 lithocholic acid pH 7.4, 25°C Oryctolagus cuniculus
0.0167
-
 5beta-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.018
-
 lithocholic acid pH 7.4, 25°C Oryctolagus cuniculus
0.019
-
 geraniol pH 7.4, 25°C Oryctolagus cuniculus
0.0217
-
 17beta-estradiol pH 7.4, 25°C Oryctolagus cuniculus
0.023
-
 5beta-Pregnan-3alpha-ol-20-one pH 7.4, 25°C Oryctolagus cuniculus
0.025
-
 Pyridine-3-aldehyde pH 7.4, 25°C Oryctolagus cuniculus
0.027
-
 farnesol pH 7.4, 25°C Oryctolagus cuniculus
0.028
-
 geraniol pH 7.4, 25°C Oryctolagus cuniculus
0.028
-
 beta-ionol pH 7.4, 25°C Oryctolagus cuniculus
0.039
-
 (S)-1-indanol pH 7.4, 25°C Oryctolagus cuniculus
0.042
-
 (S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C Oryctolagus cuniculus
0.052
-
 5beta-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.052
-
 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one pH 7.4, 25°C Oryctolagus cuniculus
0.055
-
 5alpha-androstane-3alpha,17beta-diol pH 7.4, 25°C Oryctolagus cuniculus
0.058
-
 5alpha-Androstan-3alpha-ol-17-one pH 7.4, 25°C Oryctolagus cuniculus
0.06
-
 2-Cyclohexen-1-ol pH 7.4, 25°C Oryctolagus cuniculus
0.065
-
 5alpha-androstan-17beta-ol-3-one pH 7.4, 25°C Oryctolagus cuniculus
0.067
-
 Naphthalene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.07
-
 alpha-tetralone pH 7.4, 25°C Oryctolagus cuniculus
0.072
-
 2-Cyclohexen-1-ol pH 7.4, 25°C Oryctolagus cuniculus
0.085
-
 Pyridine-3-aldehyde pH 7.4, 25°C Oryctolagus cuniculus
0.088
-
 benzene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.098
-
 testosterone pH 7.4, 25°C Oryctolagus cuniculus
0.1
-
 NAD+ pH 7.4, 25°C Oryctolagus cuniculus
0.1
-
 (S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C Oryctolagus cuniculus
0.108
-
 6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one pH 7.4, 25°C Oryctolagus cuniculus
0.118
-
 2,3-Butanedione pH 7.4, 25°C Oryctolagus cuniculus
0.123
-
 NADH pH 7.4, 25°C Oryctolagus cuniculus
0.127
-
 benzene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.13
-
 (S)-1-indanol pH 7.4, 25°C Oryctolagus cuniculus
0.152
-
 9,10-phenanthrenequinone pH 7.4, 25°C Oryctolagus cuniculus
0.155
-
 1-phenyl-1,2-propanedione pH 7.4, 25°C Oryctolagus cuniculus
0.157
-
 16-oxoestrone pH 7.4, 25°C Oryctolagus cuniculus
0.16
-
 2-Cyclohexen-1-ol pH 7.4, 25°C Oryctolagus cuniculus
0.183
-
 isatin pH 7.4, 25°C Oryctolagus cuniculus
0.183
-
 (S)-camphorquinone pH 7.4, 25°C Oryctolagus cuniculus
0.2
-
 Pyridine-3-aldehyde pH 7.4, 25°C Oryctolagus cuniculus
0.2
-
 1-phenyl-1,2-propanedione pH 7.4, 25°C Oryctolagus cuniculus
0.2
-
 alpha-tetralone pH 7.4, 25°C Oryctolagus cuniculus
0.217
-
 NADH pH 7.4, 25°C Oryctolagus cuniculus
0.217
-
 isatin pH 7.4, 25°C Oryctolagus cuniculus
0.233
-
 9,10-phenanthrenequinone pH 7.4, 25°C Oryctolagus cuniculus
0.233
-
 2,3-Butanedione pH 7.4, 25°C Oryctolagus cuniculus
0.267
-
 16-oxoestrone pH 7.4, 25°C Oryctolagus cuniculus
0.283
-
 NAD+ pH 7.4, 25°C Oryctolagus cuniculus
0.29
-
 benzene dihydrodiol pH 7.4, 25°C Oryctolagus cuniculus
0.367
-
 (S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C Oryctolagus cuniculus
0.4
-
 (S)-1-indanol pH 7.4, 25°C Oryctolagus cuniculus
0.45
-
 1-phenyl-1,2-propanedione pH 7.4, 25°C Oryctolagus cuniculus
0.49
-
 morphine pH 7.4, 25°C Oryctolagus cuniculus
0.55
-
 2,3-Butanedione pH 7.4, 25°C Oryctolagus cuniculus
0.617
-
 9,10-phenanthrenequinone pH 7.4, 25°C Oryctolagus cuniculus
0.65
-
 isatin pH 7.4, 25°C Oryctolagus cuniculus
0.683
-
 NADH pH 7.4, 25°C Oryctolagus cuniculus
0.867
-
 16-oxoestrone pH 7.4, 25°C Oryctolagus cuniculus
0.98
-
 (S)-camphorquinone pH 7.4, 25°C Oryctolagus cuniculus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
 NADH-linked (S)-camphorquinone reduction activity Oryctolagus cuniculus
7.4
-
 assay at Oryctolagus cuniculus
9.5 10 NAD+-linked (S)-tetralol dehydrogenase activity Oryctolagus cuniculus

Cofactor

Cofactor Comment Organism Structure
additional information high preference for NAD+ compared to NADP+ Oryctolagus cuniculus
additional information the rabbit enzyme shows high coenzyme preference for NAD+ over NADP+. Also in the reverse reaction, the enzymes reduces several alpha-dicarbonyl compounds including (S)-camphorquinone using NADH as the coenzyme, exhibiting low Km values of 0.004-0.006 mM. The reductase activity of the enzyme determined with NADPH as the coenzyme is less than 40% of their NADH-linked activity Oryctolagus cuniculus
additional information the rabbit enzymes show high coenzyme preference for NAD+ over NADP+. Also in the reverse reaction, the enzymes reduces several alpha-dicarbonyl compounds including S-camphorquinone using NADH as the coenzyme, exhibiting low Km values of 0.004-0.006 mM. The reductase activity of the enzyme determined with NADPH as the coenzyme is less than 40% of their NADH-linked activity Oryctolagus cuniculus
NAD+
-
 Oryctolagus cuniculus
NAD+ dependent on Oryctolagus cuniculus
NADH
-
 Oryctolagus cuniculus

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000024
-
 ikarisoside A pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus
0.00038
-
 quercitrin pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus
0.00056
-
 hinokitiol pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus
0.0007
-
 noranhydroicaritin pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus
0.0029
-
 Hexestrol pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus
0.003
-
 zearalenone pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00013
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus ikarisoside A
0.0004
-
 pH 7.4, 25°C, recombinant mutant Y118F/F310I enzyme Oryctolagus cuniculus ikarisoside A
0.00049
-
 pH 7.4, 25°C, recombinant mutant Y118F enzyme Oryctolagus cuniculus ikarisoside A
0.002
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus hinokitiol
0.0022
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus noranhydroicaritin
0.0024
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus quercitrin
0.0025
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus quercitrin
0.0026
-
 pH 7.4, 25°C, recombinant mutant Y118F/F310I enzyme Oryctolagus cuniculus hinokitiol
0.0064
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus noranhydroicaritin
0.007
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus Phenolphthalein
0.009
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus Hexestrol
0.009
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus ikarisoside A
0.009
-
 pH 7.4, 25°C, recombinant wild-type enzyme Oryctolagus cuniculus ikarisoside A
0.0091
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus zearalenone
0.01
-
 pH 7.4, 25°C, recombinant mutant Y118F enzyme Oryctolagus cuniculus hinokitiol
0.012
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus quercetin
0.013
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus ikarisoside A
0.013
-
 pH 7.4, 25°C, recombinant mutant F310I enzyme Oryctolagus cuniculus hinokitiol
0.015
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus kaempferol
0.015
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus noranhydroicaritin
0.017
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus Phenolphthalein
0.017
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus icarisid II
0.018
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus quercetin
0.02
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus kaempferol
0.02
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus Phenolphthalein
0.02
-
 above, pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus kaempferol
0.02
-
 pH 7.4, 25°C, recombinant mutant F310I enzyme Oryctolagus cuniculus ikarisoside A
0.021
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus icarisid II
0.026
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus quercetin
0.037
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus hinokitiol
0.04
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus quercitrin
0.042
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus hinokitiol
0.05
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus Hexestrol
0.05
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus zearalenone
0.05
-
 above, pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus zearalenone
0.05
-
 above, pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus icarisid II
0.05
-
 above, pH 7.4, 25°C, recombinant wild-type and mutant enzymes Oryctolagus cuniculus Hexestrol
0.05
-
 above, pH 7.4, 25°C, recombinant wild-type and mutant enzymesenzyme Oryctolagus cuniculus zearalenone
0.073
-
 pH 7.4, 25°C, recombinant enzyme Oryctolagus cuniculus Hexestrol

General Information

General Information Comment Organism
evolution the enzyme is a member of the aldo–keto reductase (AKR) 1C subfamily in the AKR superfamily Oryctolagus cuniculus
malfunction mutation of Tyr118 and Phe310 in AKR1C27 to the corresponding residues (Phe and Ile, respectively) in AKR1C28 produces an enzyme that is similar to AKR1C28 Oryctolagus cuniculus
additional information Homology structure modeling of AKR1C28 on the basis of sequence alignment and crystal structure analysis of the AKR1C5 ternary complex, PDB ID 1Q13, overview Oryctolagus cuniculus
additional information structure analysis by homology modelling, overview Oryctolagus cuniculus
additional information Tyr118 and Phe310 play key roles in ligand binding. Homology structure modeling of AKR1C27 on the basis of sequence alignment and crystal structure analysis of the AKR1C5 ternary complex, PDB ID 1Q13, overview Oryctolagus cuniculus