1.1.1.149: 20alpha-hydroxysteroid dehydrogenase
This is an abbreviated version!
For detailed information about 20alpha-hydroxysteroid dehydrogenase, go to the full flat file.
Word Map on EC 1.1.1.149
-
1.1.1.149
-
progesterone
-
androgen
-
prostate
-
reductases
-
testosterone
-
prostaglandin
-
akr1cs
-
steroidogenic
-
luteal
-
castration-resistant
-
srd5a1
-
androstenedione
-
5alpha-reductase
-
cyp17a1
-
dihydrotestosterone
-
progestin
-
akr1b10
-
17beta-hydroxysteroid
-
3alpha-hsds
-
abiraterone
-
neurosteroids
-
luteolysis
-
hsd3b1
-
5alpha-dihydrotestosterone
-
17beta-hsds
-
enzalutamide
-
flufenamic
-
17beta
-
ketosteroid
-
allopregnanolone
-
3beta-hsd
-
17alpha
-
17alpha-hydroxyprogesterone
-
hydrogenans
-
pgf2alpha
-
hsd17b3
-
pre-receptor
-
intracrine
-
3-ketosteroids
-
dihydrodiol
-
scarb1
-
analysis
-
biotechnology
-
food industry
-
medicine
-
environmental protection
- 1.1.1.149
- progesterone
- androgen
- prostate
- reductases
- testosterone
- prostaglandin
- akr1cs
-
steroidogenic
- luteal
-
castration-resistant
- srd5a1
- androstenedione
-
5alpha-reductase
- cyp17a1
- dihydrotestosterone
- progestin
- akr1b10
-
17beta-hydroxysteroid
- 3alpha-hsds
- abiraterone
-
neurosteroids
-
luteolysis
- hsd3b1
- 5alpha-dihydrotestosterone
- 17beta-hsds
-
enzalutamide
-
flufenamic
-
17beta
- ketosteroid
- allopregnanolone
- 3beta-hsd
-
17alpha
- 17alpha-hydroxyprogesterone
-
hydrogenans
-
pgf2alpha
- hsd17b3
-
pre-receptor
-
intracrine
- 3-ketosteroids
- dihydrodiol
-
scarb1
- analysis
- biotechnology
- food industry
- medicine
- environmental protection
Reaction
Synonyms
20-alpha-HSD, 20-alpha-hydroxysteroid dehydrogenase, 20alpha-HSD, 20alpha-HSDH, 20alpha-hydroxy steroid dehydrogenase, 20alpha-hydroxysteroid dehydrogenase, 20alpha-hydroxysteroid oxidoreductase, 20alpha-OH-SDH, 20beta-HSDH, 20beta-hydroxysteroid dehydrogenase, 3alpha-HSOR, 3alpha-hydroxysteroid oxidoreductase, AKR1C1, AKR1C14, AKR1C23, AKR1C3, AKR1C5, AKR1C9, aldo-keto reductase family 1 member C1, HSD1, More
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Substrates Products
Substrates Products on EC 1.1.1.149 - 20alpha-hydroxysteroid dehydrogenase
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REACTION DIAGRAM
(S)-tetralol + NAD(P)+
3,4-dihydronaphthalen-1(2H)-one + NAD(P)H + H+
-
-
-
?
17alpha,21-dihydroxy-5beta-pregnan-3,20-dione + NADPH + H+
17alpha,20alpha,21-trihydroxy-5beta-pregnane-3-one + NADP+
-
-
-
-
r
17alpha,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADPH + H+
17alpha,20alpha,21-trihydroxy-5beta-pregnane-3,11-dione + NADP+
-
-
-
-
r
17alpha,21-dihydroxyadrenocorticosteroid + NAD(P)H
? + NADP+
-
NADH preferred
-
?
17alpha-hydroxy-progesterone + NADH + H+
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD+
-
-
-
-
r
17alpha-hydroxycorticosterone + NADPH
? + NADP+
-
less reactive than with 17alpha-hydroxyrogesterone
-
?
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
2-amino-8-((2-fluoro-4-methoxybenzyl)thio)-1,9-dihydro-6H-purin-6-one + NADP+
?
-
-
-
-
r
20alpha-hydroxy-5alpha-pregnan-3-one + NADPH + H+
5alpha-pregnan-20alpha,3alpha-diol + NADP+
-
-
-
-
r
20alpha-hydroxy-5beta-pregnan-3-one + NADP+
5beta-pregnane-3,20-dione + NADPH
-
-
-
?
20alpha-hydroxypregn-4-en-3-one + 3-acetylpyridine adenine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + nicotinamide 1,N6-ethenoadenine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + nicotinamide hypoxanthine dinucleotide phosphate
?
-
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + thionicotinamide adenine dinucleotide phosphate
?
-
-
-
-
r
3alpha-hydroxy-5-alpha-pregnan-20-one + NADPH + H+
5alpha-pregnan-3alpha,20alpha-diol + NADP+
-
-
-
-
r
3alpha-hydroxy-5alpha-pregnan-20-one + NADPH + H+
5alpha-pregnan-3alpha,20alpha-diol + NADP+
-
-
-
-
r
4-pregnen-20alpha-ol-3-one + NAD(P)+
4-pregnen-3,20-dione + NAD(P)H + H+
-
-
-
-
r
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
5alpha-pregnan-3,20-dione + NAD(P)H
-
-
-
-
r
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
5alpha-pregnane-3,20-dione + NAD(P)H
-
-
-
-
r
5alpha-pregnan-20alpha-ol-3-one + NADP+
5beta-pregnan-3,20-dione + NADPH + H+
-
-
-
-
r
5alpha-pregnan-3alpha-ol-20-one + NAD(P)H
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5alpha-pregnan-3alpha-ol-20-one + NAD(P)H + H+
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5alpha-pregnane-21-ol-3,20-dione + NAD(P)H
5alpha-pregnane-20alpha,21-diol-3-one + NAD(P)+
-
-
-
-
r
5alpha-pregnane-3,20-dione + NAD(P)H
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
-
-
-
-
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
5alpha-pregnane-3alpha,21-diol-20-one + NAD(P)H + H+
5alpha-pregnane-3alpha,20alpha,21-triol + NAD(P)+
-
-
-
-
r
5beta-pregnan-20alpha-ol-3-one + NAD(P)+
5beta-pregnan-3,20-dione + NAD(P)H
-
-
-
-
r
5beta-pregnan-3,20-dione + NADPH + H+
5alpha-pregnan-20alpha-ol-3-one + NADP+
-
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H
5beta-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
-
-
-
-
r
5beta-pregnan-3alpha-ol-20-one + NAD(P)H + H+
5alpha-pregnan-3alpha,20alpha-diol + NAD(P)+
-
-
-
?
5beta-pregnane-3,20-dione + NAD(P)H + H+
5alpha-pregnan-20alpha-ol-3-one + NAD(P)+
-
-
-
-
r
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
benzene dihydrodiol + NADP+
2-hydroxycyclohexa-3,5-diene-1-one + NADPH + H+
-
-
-
-
r
corticosterone + NADPH + H+
? + NADP+
-
less reactive than with 17alpha-hydroxyprogesterone
-
?
progesterone + NADPH + H+
20alpha-hydroxyprogesterone + NADP+
-
-
-
-
?
methyl acetoacetate + NADPH + H+
-
-
-
-
r
(S)-methyl 3-hydroxybutyrate + NADP+
methyl acetoacetate + NADPH + H+
-
-
-
-
r
?
-
66% activity compared to pyridine 3-aldehyde
-
-
r
1,2-cyclohexanedione + NADP+
?
-
50% activity compared to pyridine 3-aldehyde
-
-
r
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
-
-
-
?
11-deoxycorticosterone + NAD(P)H
4-pregnen-20alpha,21-diol-3-one + NAD(P)+
-
-
-
-
?
? + NAD+
i.e. 4-pregnen-17,21-diol-3,20-dione, 66.03% compared to the activity with cortisol
-
-
?
11-deoxycortisol + NADH + H+
? + NAD+
i.e. 4-pregnen-17,21-diol-3,20-dione, 66.03% compared to the activity with cortisol
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H
-
-
-
-
r
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
17alpha-hydroxyprogesterone + NAD(P)H
-
inactive molecule form
hormone
-
r
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
the aldo-keto reductase, AKR1C23, also shows 20alpha-hydroxysteroid dehydrogenase activity in vivo, enzyme regulation in preovulatory follicles and corpora lutea, overview
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
the enzyme activity is highest in women with visceral obesity
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
NADPH is preferred to NADH in liver, while the kidney enzyme is specific for NADPH
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
progesterone catabolism
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
regulation of enzyme expression during pregnancy, the enzyme is required for prostaglandin F2alpha-dependent progesterone down-regulation before parturition, overview
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
progesterone catabolism
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H
17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
-
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
NADPH preferred
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
-
-
-
?
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
-
-
r
17alpha-hydroxyprogesterone + NAD(P)H + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NAD(P)+
-
NADPH preferred
-
-
?
17alpha,20alpha-dihydroxyprogesterone + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha,20alpha-dihydroxyprogesterone + NADP+
-
-
-
?
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
-
r
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
best substrate
-
r
17alpha-hydroxyprogesterone + NADPH + H+
17alpha,20alpha-dihydroxy-pregn-4-en-3-one + NADP+
-
-
-
-
r
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
r
5alpha-dihydroprogesterone + NADPH + H+
5alpha,20alpha-tetrahydroprogesterone + NADP+
-
-
-
-
r
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
-
-
-
-
r
5alpha-pregnane-3alpha,20alpha-diol + NAD(P)+
3alpha-hydroxy-5alpha-pregnan-20-one + NAD(P)H + H+
-
-
-
?
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
-
-
-
-
?
5beta-pregnane-3alpha,20alpha-diol + NAD(P)+
5beta-pregnan-20alpha-ol-3-one + NAD(P)H + H+
-
-
-
-
r
? + NAD+
i.e. 4-pregnen-11beta,21-diol-3,20-dione, 33.32% compared to the activity with cortisol
-
-
?
corticosterone + NADH + H+
? + NAD+
i.e. 4-pregnen-11beta,21-diol-3,20-dione, 33.32% compared to the activity with cortisol
-
-
?
20beta-hydroxycortisol + NAD+
-
-
-
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
no activity with NADPH
-
-
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
-
-
-
?
cortisol + NADH + H+
20beta-hydroxycortisol + NAD+
no activity with NADPH
-
-
?
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
4-androsten-3alpha,17beta-diol + NADP+
reaction of EC 1.1.1.357
-
-
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
reaction of EC 1.1.1.357
-
-
r
dihydrotestosterone + NADPH + H+
4-androsten-3alpha,17beta-diol + NADP+
-
reaction of EC 1.1.1.357
-
-
r
glycerol 3-phosphate + NADP+
-
-
-
-
r
DL-glyceraldehyde 3-phosphate + NADPH + H+
glycerol 3-phosphate + NADP+
-
-
-
-
r
(S)-ethyl 3-hydroxybutyrate + NADP+
-
-
-
-
?
ethyl acetoaetate + NADPH
(S)-ethyl 3-hydroxybutyrate + NADP+
-
-
-
r
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
-
-
-
-
r
progesterone + NAD(P)H
20alpha-hydroxypregn-4-en-3-one + NAD(P)+
-
i.e. pregn-4-en-3-one, importance of sulfhydryl groups in the functioning of the enzyme
-
-
r
progesterone + NAD(P)H
20alpha-hydroxyprogesterone + NAD(P)+
-
NADPH much more efficient, 4-fold lower Km
-
?
progesterone + NAD(P)H + H+
20alpha-hydroxyprogesterone + NAD(P)+
-
maternal and fetal 20alpha-HSD play a role in maintaining normal pregnancy at least partially by reducing progesterone concentrations in fetuses
-
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
central role in luteolysis and parturition
-
?
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
-
-
r
progesterone + NADPH
20alpha-hydroxyprogesterone + NADP+
-
less reactive than with 17alpha-hydroxyprogesterone
-
-
?
? + NAD+
i.e. 5beta-pregnan-3alpha,11beta,17,21-tetrol-20-one, 44.29% compared to the activity with cortisol
-
-
?
tetrahydrocortisol + NADH + H+
? + NAD+
i.e. 5beta-pregnan-3alpha,11beta,17,21-tetrol-20-one, 44.29% compared to the activity with cortisol
-
-
?
?
-
-
androstenedione and corticosterone not substrates
-
-
?
additional information
?
-
-
negligible activity with dehydroepiandrosterone, estrone estradiol, 4-androstenendione, testosterone and diydrotestosterone as substrates
-
-
?
additional information
?
-
-
pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups, lactation inhibits enzyme expression, X-zone regulation, overview
-
-
?
additional information
?
-
-
pregnancy induces X-zone regression and abolishes 20alphaHSD expression, which is partially restored in animals that are kept from nursing their pups, lactation inhibits enzyme expression, X-zone regulation, overview
-
-
?
additional information
?
-
-
no activity with 5beta-androstan-17beta-ol-3-one, 5beta-pregnan-20alpha-ol-3-one, testosterone and 20alpha-hydroxy progesterone
-
-
?
additional information
?
-
-
no activity with corticosterone and 5alpha-dihydrotestosterone as substrates, other substrate: 17alpha-hydroxyprogesterone
-
-
?
additional information
?
-
-
high activity for neuroactive steroids, 9,10-phenanthrenequinone and 4-nitrobenzaldehyde, low activity for 17alpha hydroxypregnenolone, D,L-glyceraldehyde and prostaglandin E2, no activity for 20beta-hydroxy-pregn-4-en-3-one, andro-, testosterone, 17alpha-, 17beta-oestradiol, oestrone and 5alpha-dihydrotestosterone, other substrates: DL-glyceraldehyde, prostaglandin E2, D-glucose, prednisolone, D-galactose, prednisone, pregnenolone, 5alpha-pregnane-3,20-dione, 9,10-phenanthrenequinone
-
-
?
additional information
?
-
-
no activity with 20beta isomer of 20alpha-hydroxyprogesterone, rising activity with 20alpha-hydroxyprogesterone concentrations over the range 0.05-1.0 mM, increasing activity with NADP+ over the range 0.01-0.2 mM, no NAD+ activity over this concentration range
-
-
?
additional information
?
-
-
no activity with 20beta-hydroxypregn-4-en-3-one, 5alpha-pregnan-3,20-dione, 3beta-hydroxy-5alpha-pregnan-20-one and 3alpha,20alpha-dihydroxy-5alpha-pregnane
-
-
?
additional information
?
-
-
no activity with 20alpha-hydroxy-4-pregnen-3-one
-
-
?
additional information
?
-
-
benzaldehyde, DL-glyceraldehyde, 4-nitrobenzaldehyde and glucose very efficient substrates, methylglyoxal, 9,10-phenanthrenquinone and D-galactose less active, no activity with corticosterone and 5alpha-dihydrotestosterone
-
-
?
additional information
?
-
-
no activity with corticosterone and 5alpha-dihydrotestosterone as substrates, other substrate: 17alpha-hydroxyprogesterone
-
-
?
additional information
?
-
-
less or no activity with 5beta-androstane-3,17-dione, 17beta-hydroxy-5beta-androstan-3-one, progesterone, 5beta-pregnane-3,20-dione, cortisone oestrone, 20-oxopregnenes without 17alpha-hydroxy group, 20-oxopregnanes, corticosteroides, 3- or 17-oxosteroids, 20beta-hydroxysteroids, 3- or 17-hydroxysteroids, alcohols as substrate, other substrates: isatin, ethyl acetoacetate, camphorquinone, pyridine-3-aldehyde, 1,2-cyclohexanedione, 2,4-pentanedione, 4-nitrobenzaldehyde, benzene-dihydrodiol
-
-
?
additional information
?
-
-
other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate
-
-
?
additional information
?
-
-
role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
-
-
?
additional information
?
-
-
role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
-
-
?
additional information
?
-
-
other substrates: 2,3-butanedione to 2,3-heptanedione, 1-phenyl-1,2-propanedione, ethyl 2-methylacetoacetate, acetoacetyl-CoA, ethyl pyruvate, ethyl 4-chloroacetoacetate, isatin, pyridine-3-aldehyde , not 20beta-hydroxysteroids, 1,2-cyclohexanedione, methyl acetoacetate, 2,4-pentanedione, acetoin, 4-nitrobenzaldehyde, ethyl 3-oxovalerate, 3,4-hexanedione, D-glyceraldehyde, ethyl benzoylacetate, D-lactaldehyde, DL-glceraldehyde 3-phosphate, pyridine-4-aldehyde, (S)-ethyl-3-hydroxybutyrate, trans-benzene-1S,2S-dihydrodiol, cis-benzene-1,2-dihydrodiol, (S)-methyl 3-hydroxybutyrate
-
-
?
additional information
?
-
-
role of enzyme suggested to be for detoxication or metabolism of carbonyl compounds because of broad substrate specificity
-
-
?
additional information
?
-
-
17alpha-hydroxyprogesterone inducer but not substrate
-
-
?