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Literature summary for 1.1.1.239 extracted from

  • Endo, S.; Noda, M.; Ikari, A.; Tatematsu, K.; El-Kabbani, O.; Hara, A.; Kitade, Y.; Matsunaga, T.
    Characterization of hamster NAD+-dependent 3(17)beta-hydroxysteroid dehydrogenase belonging to the aldo-keto reductase 1C subfamily (2015), J. Biochem., 158, 425-434.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene AKR1C35, cloned from liver, DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)pLysS Mesocricetus auratus

Inhibitors

Inhibitors Comment Organism Structure
Hexestrol
-
Mesocricetus auratus
hinokitiol
-
Mesocricetus auratus
additional information no or poor inhibition by 7-hydroxyflavone, chrysin, quercetin, genistein, galangin, lithocholic acid, and zearalenone Mesocricetus auratus
Phenolphthalein
-
Mesocricetus auratus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information Michaelis-Menten kinetics Mesocricetus auratus
0.0012
-
geranylgeraniol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.0097
-
beta-ionol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.011
-
farnesol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.013
-
beta-3-hydroxyhexobarbital pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.013
-
NADH pH 7.4, 25°C, with substrate S-camphorquinone Mesocricetus auratus
0.013
-
NAD+ pH 7.4, 25°C, with substrate S-tetralol Mesocricetus auratus
0.03
-
alpha-3-hydroxyhexobarbital pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.061
-
(S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.076
-
geraniol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.095
-
(R)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.148
-
1-Acenaphthenol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.162
-
nerol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.181
-
(S)-1-indanol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.569
-
2-Cyclohexen-1-ol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.63
-
cis-benzene dihydrodiol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
1
-
trans-benzene dihydrodiol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
1.38
-
NADP+ pH 7.4, 25°C, with substrate S-camphorquinone Mesocricetus auratus

Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
-
Mesocricetus auratus 5829
-

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
37000
-
recombinant His-tagged enzyme, SDS-PAGE Mesocricetus auratus

Organism

Organism UniProt Comment Textmining
Mesocricetus auratus A0A097ZMY7
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3)pLysS by nickel affinity chromatography, ultrafiltration, and dialysis Mesocricetus auratus

Source Tissue

Source Tissue Comment Organism Textmining
adrenal gland in male hamsters Mesocricetus auratus
-
colon in male hamsters Mesocricetus auratus
-
heart in female hamsters Mesocricetus auratus
-
kidney in male hamsters Mesocricetus auratus
-
liver
-
Mesocricetus auratus
-
additional information mRNA for AKR1C34 is expressed liver-specific in female hamsters and ubiquitously in male hamsters Mesocricetus auratus
-
small intestine in male hamsters Mesocricetus auratus
-
testis in male hamsters Mesocricetus auratus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+ i.e. (R)-tetralol Mesocricetus auratus 3,4-dihydronaphthalen-1(2H)-one + NADH + H+
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+ i.e. (S)-tetralol Mesocricetus auratus 3,4-dihydronaphthalen-1(2H)-one + NADH + H+
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+ i.e. (S)-tetralol Mesocricetus auratus 3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
-
?
(S)-1-indanol + NAD+
-
Mesocricetus auratus 2,3-dihydro-1H-inden-1-one + NADH + H+
-
?
(S)-camphorquinone + NADH + H+
-
Mesocricetus auratus ? + NAD+
-
?
(S)-camphorquinone + NADPH + H+
-
Mesocricetus auratus ? + NADP+
-
?
1-acenaphthenol + NAD+
-
Mesocricetus auratus acenaphthylen-1(2H)-one + NADH + H+
-
?
17beta-estradiol + NAD+
-
Mesocricetus auratus estrone + NADH + H+
-
?
2-cyclohexen-1-ol + NAD+
-
Mesocricetus auratus 2-cyclohexen-1-one + NADH + H+
-
?
20alpha-hydroxyprogesterone + NADH + H+
-
Mesocricetus auratus ? + NAD+
-
?
3alpha-hydroxyprogesterone + NADH + H+
-
Mesocricetus auratus ? + NAD+
-
?
3beta-hydroxyprogesterone + NADH + H+
-
Mesocricetus auratus ? + NAD+
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
-
Mesocricetus auratus 5alpha-androstan-3,17-dione + NADH + H+
-
?
5alpha-androstan-3beta-ol-17-one + NAD+
-
Mesocricetus auratus 5alpha-androstan-3,17-dione + NADH + H+
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
-
Mesocricetus auratus ?
-
?
5alpha-androstane-3beta,17beta-diol + NAD+
-
Mesocricetus auratus ?
-
?
5alpha-dihydrotestosterone + NAD+
-
Mesocricetus auratus 5alpha-androstane-3,17-dione + NADH + H+
-
?
5alpha-pregnan-20alpha-ol-3-one + NAD+
-
Mesocricetus auratus 5alpha-pregnan-3,20-dione + NADH + H+
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
-
Mesocricetus auratus 5alpha-pregnan-3,20-dione + NADH + H+
-
?
5alpha-pregnan-3beta-ol-20-one + NAD+
-
Mesocricetus auratus 5alpha-pregnan-3,20-dione + NADH + H+
-
?
5beta-androstan-17beta-ol-3-one + NAD+
-
Mesocricetus auratus 5beta-androstan-3,17-dione + NADH + H+
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
-
Mesocricetus auratus 5beta-androstan-3,17-dione + NADH + H+
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
-
Mesocricetus auratus ?
-
?
5beta-androstane-3beta,17beta-diol + NAD+
-
Mesocricetus auratus ?
-
?
5beta-dihydrotestosterone + NAD+
-
Mesocricetus auratus androstanedione + NADH + H+
-
?
5beta-pregnan-20alpha-ol-3-one + NAD+
-
Mesocricetus auratus 5beta-pregnan-3,20-dione + NADH + H+
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
-
Mesocricetus auratus 5beta-pregnan-3,20-dione + NADH + H+
-
?
5beta-pregnan-3beta,21-diol-20-one + NAD+
-
Mesocricetus auratus ?
-
?
5beta-pregnan-3beta-ol-20-one + NAD+
-
Mesocricetus auratus 5beta-pregnan-3,20-dione + NADH + H+
-
?
alpha-3-hydroxyhexobarbital + NAD+
-
Mesocricetus auratus ?
-
?
beta-3-hydroxyhexobarbital + NAD+
-
Mesocricetus auratus ?
-
?
beta-ionol + NAD+
-
Mesocricetus auratus (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
?
cis-benzene dihydrodiol + NAD+
-
Mesocricetus auratus ?
-
?
dehydroepiandrosterone + NAD+
-
Mesocricetus auratus ? + NADH + H+
-
?
farnesol + NAD+
-
Mesocricetus auratus farnesal + NADH + H+
-
?
geraniol + NAD+
-
Mesocricetus auratus geranial + NADH + H+
-
?
geranylgeraniol + NAD+
-
Mesocricetus auratus geranylgeranial + NADH + H+
-
?
additional information the enzyme AKR1C34 shows 3alpha/17beta/20alpha-hydroxysteroid dehydrogenase activities, substrate specificity, detailed overview. Ala54 plays a critical role in non-/recognition of the steroidal substrates. Reaction products identification by thin-layer chromatography (TLC) and liquid chromatography/mass spectrometry (LC/MS). AKR1C34 also has morphine dehydrogenase activity, EC 1.1.1.218. No activity with cyclohexanol Mesocricetus auratus ?
-
?
nerol + NAD+
-
Mesocricetus auratus neral + NADH + H+
-
?
testosterone + NAD+
-
Mesocricetus auratus 4-androstenedione + NADH + H+
-
?
trans-benzene dihydrodiol + NAD+
-
Mesocricetus auratus ?
-
?

Subunits

Subunits Comment Organism
? x * 37000, recombinant His-tagged enzyme, SDS-PAGE Mesocricetus auratus

Synonyms

Synonyms Comment Organism
AKR1C34
-
Mesocricetus auratus
More cf. EC 1.1.1.218, morphine 6-dehydrogenase Mesocricetus auratus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at Mesocricetus auratus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.0045
-
farnesol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.0075
-
(R)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.0153
-
geraniol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.025
-
NAD+ pH 7.4, 25°C, with substrate S-tetralol Mesocricetus auratus
0.028
-
2-Cyclohexen-1-ol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.032
-
cis-benzene dihydrodiol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.038
-
geranylgeraniol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.04
-
alpha-3-hydroxyhexobarbital pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.045
-
trans-benzene dihydrodiol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.053
-
beta-ionol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.0917
-
NADP+ pH 7.4, 25°C, with substrate S-camphorquinone Mesocricetus auratus
0.0967
-
beta-3-hydroxyhexobarbital pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.1
-
(S)-1-indanol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.105
-
(S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.115
-
nerol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.167
-
NADH pH 7.4, 25°C, with substrate S-camphorquinone Mesocricetus auratus
0.283
-
1-Acenaphthenol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
10
-
substrate oxidation Mesocricetus auratus

Cofactor

Cofactor Comment Organism Structure
additional information the enzyme shows high preference for NAD+ compared with NADP+ Mesocricetus auratus
NAD+ conserved residues Gln270 and Glu276 are critical residues for the NAD+ specificity Mesocricetus auratus
NADH
-
Mesocricetus auratus
NADP+
-
Mesocricetus auratus
NADPH
-
Mesocricetus auratus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00065
-
pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus Phenolphthalein
0.0032
-
pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus hinokitiol
0.013
-
pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus Hexestrol

General Information

General Information Comment Organism
evolution enzyme AKR1C34 is a member of the aldo–keto reductase (AKR) 1C subfamily in the AKR superfamily Mesocricetus auratus
physiological function enzyme AKR1C34 oxidizes various xenobiotic alicyclic alcohols using NAD+ Mesocricetus auratus

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.05
-
trans-benzene dihydrodiol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.05
-
2-Cyclohexen-1-ol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.05
-
cis-benzene dihydrodiol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.067
-
nerol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.067
-
NADP+ pH 7.4, 25°C, with substrate S-camphorquinone Mesocricetus auratus
0.083
-
(R)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.2
-
geraniol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.42
-
farnesol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
0.55
-
(S)-1-indanol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
1.67
-
(S)-1,2,3,4-tetrahydro-1-naphthol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
1.83
-
1-Acenaphthenol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
2
-
NAD+ pH 7.4, 25°C, with substrate S-tetralol Mesocricetus auratus
2.17
-
alpha-3-hydroxyhexobarbital pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
5.3
-
beta-ionol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
7.5
-
beta-3-hydroxyhexobarbital pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus
12.67
-
NADH pH 7.4, 25°C, with substrate S-camphorquinone Mesocricetus auratus
33.3
-
geranylgeraniol pH 7.4, 25°C, recombinant enzyme Mesocricetus auratus