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Enzyme Nomenclature
Information on EC 1.1.1.239 - 3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)
for references in articles please use BRENDA:EC1.1.1.239
Word Map on EC 1.1.1.239
- 1.1.1.239
-
androgen
- estradiol
-
steroidogenic
- androstenedione
- 3beta-hsd
- akr1c3
-
3beta-hydroxysteroid
- aromatase
- estrone
-
steroidogenesis
- testicular
- dehydroepiandrosterone
-
5alpha-reductase
- 3alpha-hsds
- leydig
-
3alpha-hydroxysteroid
- dihydrotestosterone
- 5alpha-dihydrotestosterone
- p450scc
-
hydroxysteroids
-
4-dione
-
cochliobolus
- lunatus
- androsterone
- pseudohermaphroditism
- 4-androstene-3,17-dione
- p450arom
-
intracrine
- medicine
-
5alpha-dht
- coumestrol
- delta5-3beta-hsd
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
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EC NUMBER 
COMMENTARY 
1.1.1.239
-
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RECOMMENDED NAME
GeneOntology No.
3alpha(17beta)-hydroxysteroid dehydrogenase (NAD+)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
testosterone + NAD+ = androstenedione + NADH + H+
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
3alpha(or 17beta)-hydroxysteroid:NAD+ oxidoreductase
Also acts on other 17beta-hydroxysteroids and on the 3alpha-hydroxy group of pregnanes and bile acids. Different from EC 1.1.1.50 3alpha-hydroxysteroid dehydrogenase (Si-specific) or EC 1.1.1.213 3alpha-hydroxysteroid dehydrogenase (Re-specific).
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CAS REGISTRY NUMBER
COMMENTARY
126469-82-7
-
9028-62-0
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
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
physiological function
additional information
evolution
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the enzyme is a member of the aldo-keto reductase (AKR) superfamily that metabolizes endogenous substrates, such as carbohydrates, prostaglandins and steroids, and xenobiotics in a NAD(P)(H)-dependent manner
evolution
the enzyme is a member of the aldo–keto reductase (AKR) 1C subfamily in the AKR superfamily; the enzyme is a member of the aldo–keto reductase (AKR) 1C subfamily in the AKR superfamily; the enzyme is a member of the aldo–keto reductase (AKR) 1C subfamily in the AKR superfamily
evolution
enzyme AKR1C34 is a member of the aldo–keto reductase (AKR) 1C subfamily in the AKR superfamily
physiological function
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exposure of HCT-15 cells to cisplatin results in aquisition of cisplatin resistance and concomitant induction of isoform AKR1C3 and aldo-keto reductase AKR1C1 expression. The resistance lowers the sensitivity toward cellular damages evoked by oxidative stress-derived aldehydes, 4-hydroxy-2-nonenal and 4-oxo-2-nonenal that are detoxified by AKR1C1 and AKR1C3. Overexpression of AKR1C1 or AKR1C3 in the parental HCT15 cells mitigates the cytotoxicity of the aldehydes and cisplatin. Knockdown of both AKR1C1 and AKR1C3 in the resistant cells or treatment of the cells with specific inhibitors of the aldo-keto reductases increases the sensitivity to ciplatin toxicity
physiological function
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AKR1C3 catalyzes the conversion of the weak androgen precursors 4-androstene-3,17-dione and 5alpha-androstane-3,17-dione to the potent androgens testosterone and 5alpha-dihydrotestosterone (DHT), respectively, and is one of the most highly upregulated genes in castrate-resistant prostate cancer, CRPC
physiological function
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in LNCaP and LNCaP-AKR1C3 cells overexpressing isoform AKR1C3, metabolism proceeds via 5alpha-reduction to form 5alpha-androstane-3,17-dione and then (epi)androsterone-3-glucuronide. LNCaP-AKR1C3 cells make significantly higher amounts of testosterone-17beta-glucuronide. When 5alpha-reductase is inhibited by finasteride, the production of testosterone-17beta-glucuronide is further elevated in LNCaP-AKR1C3 cells. When AKR1C3 activity is inhibited with indomethacin the production of testosterone-17beta-glucuronide is significantly decreased. 4-Androstene-3,17-dione treatment stimulates cell proliferation in both cell lines. LNCaP-AKR1C3 cells are resistant to the growth inhibitory properties of finasteride, consistent with the diversion of 4-androstene-3,17-dione metabolism from 5alpha-reduced androgens to increased formation of testosterone
physiological function
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crucial role of AKR1C3 in the acquisition of daunorubicin resistance of leukemic cells by metabolizing both daunorubicin and cytotoxic aldehydes derived from ROS-linked lipid peroxidation. Daunorubicin, at its sublethal doses, induces the expression of AKR1C1, EC 1.1.1.149, and AKR1C3, both of which reduce the daunorubicin sensitivity of the cells, AKR1C3 is more inducible than AKR1C1 by the daunorubicin treatment
physiological function
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aldo-keto reductase 1C3 (AKR1C3), also known as type 5 17beta-hydroxysteroid dehydrogenase, is a downstream steroidogenic enzyme and converts androgen precursors to the potent androgen receptor ligands testosterone and 5alpha-dihydrotestosterone. AKR1C3 is involved in the development of castration resistant prostate cancer (CRPC)
physiological function
enzyme AKR1C34 oxidizes various xenobiotic alicyclic alcohols using NAD+
additional information
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the structure of the AKR1C3-NADP+ complex is solved by molecular replacement, overview
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; structure analysis by homology modelling, overview; structure analysis by homology modelling, overview; 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
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; structure analysis by homology modelling, overview; structure analysis by homology modelling, overview; 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
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; structure analysis by homology modelling, overview; structure analysis by homology modelling, overview; 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
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (R)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH
-
i.e. (S)-tetralol
-
-
r
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADH + H+
i.e. (S)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NAD+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
i.e. (S)-tetralol
-
-
?
(S)-1,2,3,4-tetrahydro-1-naphthol + NADP+
3,4-dihydronaphthalen-1(2H)-one + NADPH + H+
i.e. (S)-tetralol
-
-
?
1-acenaphthenol + NAD+
acenaphthylen-1(2H)-one + NADH + H+
-
-
-
?
1-phenyl-1,2-propanedione + NADH + H+
? + NAD+
-
-
-
?
11alpha-hydroxytestosterone + NAD+
11alpha-hydroxyandrost-4-ene-3,17-dione + NADH
-
156% velocity compared to testosterone
-
r
15alpha-hydroxytestosterone + NAD+
15alpha-hydroxyandrost-4-ene-3,17-dione + NADH
-
131% velocity compared to testosterone
-
r
17beta-hydroxy-1alpha-methyl-5alpha-androstan-3-one + NAD+
1alpha-methyl-5alpha-androstane-3,17-dione + NADH
-
192% velocity compared to testosterone
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r
17beta-hydroxy-5beta-androstan-3-one + NAD+
5beta-androstane-3,17-dione + NADH
-
86% velocity compared to testosterone
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r
2-[(2-bromoethyl)(2-[[(2-hydroxyethyl)amino]methyl]-4,6-dinitrophenyl)amino]ethyl methanesulfonate + 2 NADH + 2 H+
2-[(2-bromoethyl)[4-(hydroxyamino)-2-[[(2-hydroxyethyl)amino]methyl]-6-nitrophenyl]amino]ethyl methanesulfonate + 2 NAD+ + H2O
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i.e. PR-104A, phosphate ester prodrug designed to exploit tumor hypoxia
i.e. PR-104H, enzyme acts as nitroreductase for activation of PR-104A
-
-
3beta-hydroxy-5alpha-androstane-17-one + NAD+
5alpha-androstane-3,17-dione + NADH
-
75% velocity compared to testosterone
-
r
4-pregnen-3alpha-ol-2-one + NAD+
4-pregnen-3,20-dione + NADH + H+
-
-
-
r
4-pregnen-3alpha-ol-20-one + NAD+
4-pregnen-3,20-dione + NADH + H+
-
-
-
?
5alpha-androstan-17beta-ol-3-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstan-3alpha,17beta-diol + NAD+
5alpha-androstan-3alpha-ol-17-one + NADH
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,20-dione + NADH + H+
-
-
-
?
5alpha-androstan-3beta-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstane-17beta-ol-3-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
5alpha-androstane-3,17-dione + NADH + H+
? + NAD+
-
-
-
?
5alpha-dihydrotestosterone + NAD+
5alpha-androstane-3,17-dione + NADH
-
133% velocity compared to testosterone
-
r
5alpha-dihydrotestosterone + NADH + H+
testosterone + NADH + H+
-
-
-
?
5alpha-pregnan-20alpha-ol-3-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3,21alpha-diol-20-one + NAD+
5alpha-pregnan-21-ol-3,20-dione + NADH
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3beta-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH
-
-
-
?
5beta-androstan-3alpha,17beta-diol + NAD+
5beta-androstan-3alpha-ol-17-one + NADH
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
5beta-androstane-17beta-ol-3-one + NAD+
5beta-nbdrostan-3,17-dione + NADH + H+
-
-
-
r
5beta-androstane-3,17-dione + NADH + H+
? + NAD+
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
5beta-androstane-3alpha-ol-17-one + NADH
-
57% velocity compared to testosterone
-
r
5beta-dihydrotestosterone + NAD+
androstanedione + NADH
-
50% initial velocity compared to testosterone
-
r
5beta-dihydrotestosterone + NAD+
testosterone + NADH + H+
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3alpha,21-diol-20-one + NAD+
5beta-pregnan-21-ol-3,20-dione + NADH
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH
-
-
-
?
5beta-pregnan-3beta-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one + NADH + H+
? + NAD+
-
-
-
?
6beta-hydroxytestosterone + NAD+
6beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
84% velocity compared to testosterone
-
r
9,10-phenanthrenequinone + NADH + H+
? + NAD+
-
-
-
?
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH
-
75% velocity compared to testosterone
-
r
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
-
-
-
-
?
androst-5-ene-3beta,17beta-diol + NAD+
androst-5-ene-3beta-ol-17-one + NADH
-
33% velocity compared to testosterone
-
r
glycochenodeoxycholic acid + NAD+
7alpha-hydroxy-3-oxo-5-beta-cholanoyl glycine + NADH
-
-
-
?
glycolithocholic acid + NAD+
3-oxo-5beta-cholanoyl glycine + NADH
-
-
-
?
lithocholic acid
5beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
-
lithocholic acid + NAD+
5-beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH
-
-
-
?
lithocholic acid + NAD+
5beta-cholan-3-one-24-oic acid + NADH + H+
-
-
-
?
morphine + NAD+
morphinone + NADH + H+
reaction of EC 1.1.1.218
-
-
?
naphthalene dihydrodiol + NAD+
? + NADH + H+
-
-
-
?
testosterone + NADP+
androst-4-ene-3,17-dione + NADPH + H+
-
NADP is 3fold less efficient as cofactor
-
r
testosterone + NADP+
androstenedione + NADPH + H+
-
-
-
r
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
-
-
-
?
(S)-1-indanol + NAD+
2,3-dihydro-1H-inden-1-one + NADH + H+
-
-
-
?
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
136% velocity compared to testosterone
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
-
-
r
11beta-hydroxytestosterone + NAD+
11beta-hydroxyandrost-4-ene-3,17-dione + NADH
-
76% of testosterone oxidation rate
-
r
17beta-estradiol + NAD+
estrone + NADH + H+
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
-
-
-
?
2-cyclohexen-1-ol + NAD+
2-cyclohexen-1-one + NADH + H+
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
?
5alpha-androstan-3alpha-ol-17-one + NAD+
5alpha-androstan-3,17-dione + NADH + H+
-
-
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
-
72% velocity compared to testosterone
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+
5alpha-androstane-3alpha-ol-17-one + NADH
-
204% velocity compared to testosterone
-
r
5alpha-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
-
-
-
?
5alpha-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
-
-
-
r
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
-
72% velocity compared to testosterone
-
r
5alpha-androstane-3beta,17beta-diol + NAD+
5alpha-androstane-3beta-ol-17-one + NADH
-
17% velocity compared to testosterone
-
r
5alpha-dihydrotestosterone + NAD+
androstanedione + NADH
-
119% initial velocity compared to testosterone
-
r
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NAD+
5alpha-pregnan-3,20-dione + NADH + H+
-
-
-
r
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-17beta-ol-3-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstan-3alpha-ol-17-one + NAD+
5beta-androstan-3,17-dione + NADH + H+
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
-
-
-
?
5beta-androstane-3alpha,17beta-diol + NAD+
? + NADH + H+
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
?
5beta-pregnan-3alpha-ol-20-one + NAD+
5beta-pregnan-3,20-dione + NADH + H+
-
-
-
r
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
-
-
?
beta-ionol + NAD+
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + NADH + H+
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
-
inactivation of the anticancer drug
-
-
r
daunorubicin + NADPH + H+
daunorubicinol + NADP+
-
the enzyme reduces daunorubicin to its corresponding alcohol daunorubicinol using NADPH as the coenzyme
-
-
r
estradiol + NAD+
estrone + NADH
-
72% velocity compared to testosterone oxidation
-
r
estradiol + NAD+
estrone + NADH
-
46% of testosterone oxidation rate
-
r
estradiol + NAD+
estrone + NADH
-
15% velocity compared to testosterone oxidation
-
r
testosterone + NAD+
4-androstenedione + NADPH + H+
-
-
-
?
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
-
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
-
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
-
testosterone + NAD+
androstenedione + NADH + H+
-
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
-
-
r
testosterone + NAD+
androstenedione + NADH + H+
-
-
-
r
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
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
-
-
-
additional information
?
-
the enzyme shows NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids
-
-
-
additional information
?
-
the enzyme shows NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids
-
-
-
additional information
?
-
the enzyme shows NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3beta,17beta-diol + NAD+
androst-4-ene-3beta-ol-17-one + NADH + H+
-
-
-
-
?
daunorubicin + NADPH + H+
daunorubicinol + NADP+
-
inactivation of the anticancer drug
-
-
r
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
-
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
-
testosterone + NAD+
androst-4-ene-3,17-dione + NADH + H+
-
-
-
-
testosterone + NAD+
androstenedione + NADH + H+
-
the enzyme shows LNCaP-AKR1C3 mediates formation of testosterone, conversion of 4-androstene-3,17-dione to testosterone
-
-
r
testosterone + NAD+
androstenedione + NADH + H+
G1T465, J7M9D0, J7MBS9
-
-
-
r
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NAD+
conserved residues Gln270 and Glu276 are critical residues for the NAD+ specificity
NADH
-
A-specific, i.e. transfer of pro-R-hydrogen from NADH to substrate
additional information
high preference for NAD+ compared to NADP+; 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; 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; 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
-
additional information
high preference for NAD+ compared to NADP+; 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; 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; 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
-
additional information
high preference for NAD+ compared to NADP+; 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; 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; 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
-
additional information
the enzyme shows high preference for NAD+ compared with NADP+
-
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoic acid
-
i.e. baccharin, a component of Brazilian propolis, exhibits a high inhibitory potency and selectivity for AKR1C3 over other AKR1C isoforms. When the cinnamic acid group of baccharin is esterified, there is a dramatic decrease in potency and selectivity for AKR1C3 in comparison to baccharin. Low or submicromolar inhibition is observed when the 3-prenyl group of baccharin is removed, and the selectivity over AKR1C2 is low. Inhibition of NAD+ dependent oxidation of S-tetralol
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
-
93.5% inhibition at 0.1 mM
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
-
37% inhibition at 0.010 mM
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-estradiol
-
0.175 mM, 25-40% inhibition of testosterone oxidation
2'-des-methyl-indomethacin
-
the cofactor binding cavity of AKR1C3 is not perturbed upon binding of the inhibitor
-
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
-
inhibitor is about 1000times more selective for isoform AKR1C3 over AKR1C2, and selectivity is even higher when compared with AKR1C1 and AKR1C4
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
-
-
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
-
-
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-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(5-chlorothiophene-2-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
-
-
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
-
-
3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
-
360fold selectivity for the inhibition of isoform AKR1C3 over AKR1C2
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
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
-
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
-
-
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
-
-
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
-
-
biochain A
-
0.014 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.008 mM, oxidation of androstanediol
coumestrol
-
0.005 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.011 mM, 50% inhibition, oxidation of androstanediol
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
-
-
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
-
-
tert-butyl(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
-
-
Triton X-100
-
immediate loss of 60-70% activity, remaining activity is stable for 4 days, competitive vs. testosterone, non-competitive vs. NAD+
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
-
-
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
quercetin
-
0.009 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.005 mM, oxidation of androstanediol
zearalenone
-
0.004 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.002 mM, oxidation of androstanediol
additional information
-
development of potent and selective indomethacin analogues for the inhibition of AKR1C3 in castrate-resistant prostate cancer, overview. Increasing the length of the aliphatic side chain of indomethacin from -ethyl to -propyl leads to a 2fold reduction in AKR1C3 potency, but the compound retained 257fold selectivity for AKR1C3 over AKR1C2
-
additional information
-
screening of baccharin analogues as selective inhibitors against type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3), selectivity versus AKR1C2
-
additional information
no or poor inhibition by 7-hydroxyflavone, chrysin, quercetin, genistein, galangin, lithocholic acid, and zearalenone
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.095
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.03
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.013
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.63
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.004
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C
0.022
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C
0.061
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.25
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C
0.00067
5alpha-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0078
5alpha-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.13
5alpha-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0022
5alpha-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.0092
5alpha-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.0005
5alpha-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.0078
5alpha-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.00067
5alpha-pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.0035
5alpha-pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.00067
5beta-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0076
5beta-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.03
5beta-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0015
5beta-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.0023
5beta-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.0022
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.02
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.0036
5beta-Pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.0037
5beta-Pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.0021
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
pH 7.4, 25°C
0.0042
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
pH 7.4, 25°C
0.101
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
pH 7.4, 25°C
0.0001
9,10-phenanthrenequinone
pH 7.4, 25°C; pH 7.4, 25°C
0.0185
NAD+
-
enzyme avtivity in hepatic microsomes, one individual animal
0.0174
testosterone
-
enzyme avtivity in hepatic microsomes, one individual animal
additional information
additional information
Michaelis-Menten kinetics; Michaelis-Menten kinetics; Michaelis-Menten kinetics of wild-type and mutant enzymes, overview
-
additional information
additional information
Michaelis-Menten kinetics; Michaelis-Menten kinetics; Michaelis-Menten kinetics of wild-type and mutant enzymes, overview
-
additional information
additional information
Michaelis-Menten kinetics; Michaelis-Menten kinetics; Michaelis-Menten kinetics of wild-type and mutant enzymes, overview
-
additional information
additional information
Michaelis-Menten kinetics
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0075
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.04
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.0967
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.032
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.045
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.042
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C
0.1
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C
0.105
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
0.367
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C
0.183
(S)-camphorquinone
pH 7.4, 25°C; pH 7.4, 25°C
-
0.0052
5alpha-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0103
5alpha-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.065
5alpha-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0033
5alpha-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.058
5alpha-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.0027
5alpha-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.055
5alpha-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.0012
5alpha-pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.0072
5alpha-pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.002
5beta-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0032
5beta-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0167
5beta-androstan-17beta-ol-3-one
pH 7.4, 25°C
0.0023
5beta-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.052
5beta-Androstan-3alpha-ol-17-one
pH 7.4, 25°C
0.004
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.0122
5beta-androstane-3alpha,17beta-diol
pH 7.4, 25°C
0.005
5beta-Pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.0074
5beta-Pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.023
5beta-Pregnan-3alpha-ol-20-one
pH 7.4, 25°C
0.052
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
pH 7.4, 25°C
0.108
6-tert-butyl-2,3-epoxy-4-hydroxy-5-cyclohexen-1-one
pH 7.4, 25°C; pH 7.4, 25°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.083
(R)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
1.67
(S)-1,2,3,4-tetrahydro-1-naphthol
pH 7.4, 25°C, recombinant enzyme
2.17
alpha-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
7.5
beta-3-hydroxyhexobarbital
pH 7.4, 25°C, recombinant enzyme
-
0.05
cis-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
0.05
trans-benzene dihydrodiol
pH 7.4, 25°C, recombinant enzyme
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000107
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
-
pH 7.0, temperature not specified in the publication
0.00273
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
-
pH 7.0, temperature not specified in the publication
0.0029
Hexestrol
pH 7.4, 25°C, recombinant enzyme
0.00056
hinokitiol
pH 7.4, 25°C, recombinant enzyme
0.000024
ikarisoside A
pH 7.4, 25°C, recombinant enzyme
-
0.0007
noranhydroicaritin
pH 7.4, 25°C, recombinant enzyme
-
0.00038
quercitrin
pH 7.4, 25°C, recombinant enzyme
0.003
zearalenone
pH 7.4, 25°C, recombinant enzyme
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.021
(2E)-3-(3,3-dimethyl-3,4-dihydro-2H-1-benzopyran-6-yl)prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.0136
(2E)-3-(4-bromophenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0136
(2E)-3-(4-ethylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0134
(2E)-3-(4-methylphenyl)-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0001
(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
0.0086
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.00044
(2E)-3-[4-(acetyloxy)-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
Homo sapiens
-
pH 7.0, 37°C
0.0058
(2E)-3-[4-(methylsulfanyl)phenyl]-2-[4-(methylsulfonyl)phenyl]prop-2-enoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0097
(2E)-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.00356
(4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.632
(Z/E)-tert-butyl 3-(4-(3-phenylpropanoyloxy)phenyl)acrylate
Homo sapiens
-
pH 7.0, 37°C
0.000094
1-(4-[[(2R)-2-methylpiperidin-1-yl]sulfonyl]phenyl)-1,3-dihydro-2H-pyrrol-2-one
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.000056
1-(4-[[(2R,6S)-2,6-dimethylpiperidin-1-yl]sulfonyl]phenyl)pyrrolidin-2-one
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.000052
1-[4-(3,4-dihydroisoquinolin-2(1H)-ylsulfonyl)phenyl]pyrrolidin-2-one
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.000213
2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(2-hydroxyphenyl)acetamide
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.00882
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(2-methylbenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00111
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-cyanobenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00786
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-fluorobenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0058
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methoxybenzene-1-sulfonyl)acetamide
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0124
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-methylbenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00252
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(4-phenoxybenzene-1-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00373
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(5-chlorothiophene-2-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.012
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(methanesulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00119
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(naphthalene-2-sulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00021
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00265
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[3-(trifluoromethyl)benzene-1-sulfonyl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00634
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]acetamide
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00207
2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00074
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(trifluoromethanesulfonyl)acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0052
2-[[(3-hydroxyphenyl)carbonyl]amino]-4,5-dimethoxybenzoic acid
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.00084
2-[[(3-hydroxyphenyl)carbonyl]amino]-5-nitrobenzoic acid
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.08
3-((4-nitronaphthalen-1-yl)amino)benzoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.1
3-(5-methoxy-2-methyl-1H-indol-3-yl)propanoic acid
Homo sapiens
-
above, 100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.000036
3-[(4-nitrophenyl)amino]benzoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00015
3-[1-(4-chlorobenzoyl)-2-ethyl-5-methoxy-1H-indol-3-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00029
3-[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00022
3-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00012
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00029
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-2-methylpropanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00325
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(2-methylbenzene-1-sulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00311
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(4-methylbenzene-1-sulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00553
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)-2-methylpropanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00034
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(methanesulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00254
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(naphthalene-2-sulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00144
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-(trifluoromethanesulfonyl)propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00469
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(propan-2-yl)benzene-1-sulfonyl]propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0025
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethoxy)benzene-1-sulfonyl]propanamide
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00111
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]-N-[4-(trifluoromethyl)benzene-1-sulfonyl]propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00013
3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.000054
3-[[4-(methoxymethyl)phenyl]amino]benzoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.000062
3-[[4-(trifluoromethyl)phenyl]amino]benzoic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00546
3a-phenyl-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]benzimidazol-1-one
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.00015
4-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]butanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0019
5-bromo-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.0022
5-chloro-2-[[(3-hydroxyphenyl)carbonyl]amino]benzoic acid
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.0024
5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.000279
6-methoxy-9-[3-(trifluoromethyl)benzoyl]-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00034
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00016
9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00507
9-(4-chlorobenzoyl)-N-(methanesulfonyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0001
indomethacin
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.02278
methyl 5-methoxy-3-(2-oxobutyl)-1H-indole-1-carboxylate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.01134
methyl [1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00564
methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00209
N-(4-acetylbenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00265
N-(4-acetylbenzene-1-sulfonyl)-3-[1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl]propanamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00397
N-(4-bromobenzene-1-sulfonyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00194
N-[2,5-bis(trifluoromethyl)benzene-1-sulfonyl]-2-[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetamide
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
607
tert-butyl(2E)-3-[3-(3-methylbut-2-en-1-yl)-4-[(3-phenylpropanoyl)oxy]phenyl]prop-2-enoate
Homo sapiens
-
pH 7.0, 37°C
0.0005
[1-(4-chlorobenzoyl)-5-fluoro-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00025
[1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00096
[1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00007
[1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00496
[1-(4-fluorobenzoyl)-5-methoxy-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00071
[1-(4-fluorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00012
[1-[4-(chloromethyl)benzoyl]-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00223
[5-fluoro-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00014
[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00521
[5-methoxy-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00108
[5-methoxy-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00016
[5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00244
[5-methoxy-2-methyl-1-[3-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00027
[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-1H-indol-3-yl]acetic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00007
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00009
3-[1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl]propanoic acid
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.05
Hexestrol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
above, pH 7.4, 25°C, recombinant wild-type and mutant enzymes; pH 7.4, 25°C, recombinant enzyme
0.002
hinokitiol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.0026
hinokitiol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant mutant Y118F/F310I enzyme
0.01
hinokitiol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant mutant Y118F enzyme
0.013
hinokitiol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant mutant F310I enzyme
0.037
hinokitiol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.042
hinokitiol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.017
icarisid II
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.021
icarisid II
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.05
icarisid II
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
above, pH 7.4, 25°C, recombinant enzyme
-
0.00013
ikarisoside A
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.0004
ikarisoside A
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant mutant Y118F/F310I enzyme
-
0.00049
ikarisoside A
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant mutant Y118F enzyme
-
0.009
ikarisoside A
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme; pH 7.4, 25°C, recombinant wild-type enzyme
-
0.013
ikarisoside A
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.02
ikarisoside A
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant mutant F310I enzyme
-
0.015
kaempferol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.02
kaempferol
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
above, pH 7.4, 25°C, recombinant enzyme; above, pH 7.4, 25°C, recombinant enzyme; pH 7.4, 25°C, recombinant enzyme
0.00224
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00759
methyl [5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl]acetate
Homo sapiens
-
100 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.00754
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
Homo sapiens
-
110 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.01571
methyl [5-methoxy-2-methyl-1-(4-methylbenzoyl)-1H-indol-3-yl]acetate
Homo sapiens
-
111 mM Tris-HCl buffer, 37°C, pH not specified in the publication
0.0022
noranhydroicaritin
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.0064
noranhydroicaritin
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.015
noranhydroicaritin
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
-
0.007
Phenolphthalein
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.017
Phenolphthalein
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.02
Phenolphthalein
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.0024
quercitrin
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.0025
quercitrin
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.0091
zearalenone
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
pH 7.4, 25°C, recombinant enzyme
0.05
zearalenone
Oryctolagus cuniculus
G1T465, J7M9D0, J7MBS9
above, pH 7.4, 25°C, recombinant enzyme; above, pH 7.4, 25°C, recombinant wild-type and mutant enzymesenzyme; pH 7.4, 25°C, recombinant enzyme
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
0.046 micromol min/g liver, microsomes, substrate 5alpha-dihydrotestosterone, coenzyme NADP+; 0.086 micromol min/g liver, microsomes, substrate testosterone, coenzyme NADP+; 0.144 micromol min/g liver, microsomes, substrate 5beta-dihydrotestosterone, coenzyme NADP+; 0.1556 micromol min/g liver, microsomes, substrate 5alpha-dihydrotestosterone, coenzyme NAD+; 0.186 micromol min/g liver, microsomes, substrate testosterone, coenzyme NAD+; 0.388 micromol min/g liver, microsomes, substrate 5beta-dihydrotestosterone, coenzyme NAD+
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
9 - 10
-
oxidation of testosterone, equal velocity of oxidation and reduction at pH 8.0
9.5 - 10
NAD+-linked (S)-tetralol dehydrogenase activity; NAD+-linked (S)-tetralol dehydrogenase activity; NAD+-linked (S)-tetralol dehydrogenase activity
10
6
NADH-linked (S)-camphorquinone reduction activity; NADH-linked (S)-camphorquinone reduction activity; NADH-linked (S)-camphorquinone reduction activity
7
-
oxidation of testosterone, equal velocity of oxidation and reduction at pH 6.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
45
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
uniform, diffuse, and strong expression of isoform AKR1C3 in normal endometrial epithelium but not in endometrial stromal cells. The expression of AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
-
uniform, diffuse, and strong expression of isoform AKR1C3 in normal endometrial epithelium but not in endometrial stromal cells. The expression of AKR1C3 is reduced in both hyperplastic and carcinomatous endometrial epithelium
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
strong isoform AKR1C3 immunoreactivity in columnar epithelium but only weak immunoreactivity in squamous epithelium of the gastrointestinal junction
-
pre- and peri-pubertal changes promote expression of the enzyme in Leydig cells
-
strong isoform AKR1C3 immunoreactivity in bronchial epithelium but not in bronchial glands or alveolar pneumocytes
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
-
in contrast to the normal adult testis, the pediatric cryptorchid testis shows AKR1C3 expression in 18%-26% of Sertoli cells in patients at Tanner stages 2 and beyond
-
positive AKR1C3 immunoreactivity is extensively present in both adenocarcinoma and squamous cell carcinoma arising from the lung and the gastroesophageal junction
additional information
high expression level of AKR1C27; high expression level of AKR1C28
high expression level of AKR1C26; low expression level of AKR1C27