1.3.1.3: DELTA4-3-oxosteroid 5beta-reductase
This is an abbreviated version!
For detailed information about DELTA4-3-oxosteroid 5beta-reductase, go to the full flat file.
Word Map on EC 1.3.1.3
Reaction
Synonyms
3-oxo-DELTA4-steroid 5beta-reductase, 4,5beta-dihydrocortisone:NADP+ DELTA4-oxidoreductase, 5-beta-reductase, 5beta-POR, 5beta-red, AKR1D1, AKR1D4, aldo-keto reductase, aldo-keto reductase 1D1, aldo–keto reductase 1D1, androstenedione 5beta-reductase, CARUB_v10005016mg, cortisone 5beta-reductase, cortisone beta-reductase, DELTA 4-5beta-reductase, DELTA4-3-ketosteroid 5beta-reductase, DELTA4-3-oxosteroid 5beta-reductase, DELTA4-hydrogenase, EC 1.3.1.23, EC 1.3.1.3, h5beta-red, h5beta-reductase, More, P5betaR, progesterone 5beta-reductase, reductase, cholestenone 5beta.-, reductase, cortisone DELTA4-5beta-, SRD5beta, St5betaR1, steroid 5beta-reductase, steroid 5beta.-reductase, testosterone 5-beta-reductase, testosterone 5beta-reductase
ECTree
1.3.1.3 DELTA4-3-oxosteroid 5beta-reductaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 1.3.1.3 - DELTA4-3-oxosteroid 5beta-reductase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
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
(20S)-21-hydroxy-20-methylpregn-4-en-3-one + NADPH + H+
? + NADP+
-
-
-
?
11beta,17alpha,21-trihydroxy-pregn-4-en-3,20-dione + NADPH
11beta,17alpha,21-trihydroxypregnan-3,20-dione + NADP+
17alpha,21-dihydroxy-pregn-4-en-3,20-dione + NADPH
17alpha,21-dihydroxy-pregnan-3,20-dione + NADP+
4-androstene-3,17-dione + NADPH + H+
5beta-androstan-3,15-dione + 3alpha-hydroxy-5beta-androstan-17-one + NADP+
-
-
-
?
4-androstene-3,17-dione + NADPH + H+
5beta-androstan-3,17-dione + NADP+
-
-
-
?
7alpha,12alpha-dihydroxy-4-cholesten-3-one + NADPH
7alpha,12alpha-dihydroxy-5-beta-cholestan-3-one + NADP+
-
-
-
-
?
7alpha,12beta-dihydroxy-4-cholesten-3-one + NADPH + H+
(5beta,7alpha,12beta)-7,12-dihydroxycholestan-3-one + NADP+
-
-
-
?
7alpha-hydroxy-4-cholesten + NADPH
7alpha-hydroxy-5beta-cholestan-3-one + NADP+
-
-
-
?
7alpha-hydroxy-4-cholesten-3-one + NADPH
(5beta,7alpha)-7-hydroxycholestan-3-one + NADP+
-
-
-
?
7alpha-hydroxy-4-cholesten-3-one + NADPH + H+
7alpha-hydroxy-5beta-cholestan-3-one + NADP+
-
-
-
-
r
cortisol + NADPH + H+
11beta,17,21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
-
-
-
?
DELTA 4-cholestene-7alpha,12alpha-diol-3-one + NADPH + H+
5beta-cholestane-7alpha,12alpha-diol-3-one + NADP+
-
a bile acid intermediate
-
-
?
DELTA4-cholesten-7alpha-ol-3-one + NADPH + H+
5beta-cholestan-7alpha-ol-3-one + NADP+
-
a bile acid intermediate
-
-
?
dexamethasone + NADPH + H+
? + NADP+
substrate of splice variant AKR1D1-002
-
-
?
prednisolone + NADPH + H+
? + NADP+
substrate of splice variant AKR1D1-002
-
-
?
11beta,17alpha,21-trihydroxy-pregn-4-en-3,20-dione + NADPH
11beta,17alpha,21-trihydroxypregnan-3,20-dione + NADP+
-
-
-
?
11beta,17alpha,21-trihydroxy-pregn-4-en-3,20-dione + NADPH
11beta,17alpha,21-trihydroxypregnan-3,20-dione + NADP+
-
-
-
?
17alpha,21-dihydroxy-pregn-4-en-3,20-dione + NADPH
17alpha,21-dihydroxy-pregnan-3,20-dione + NADP+
-
-
-
?
17alpha,21-dihydroxy-pregn-4-en-3,20-dione + NADPH
17alpha,21-dihydroxy-pregnan-3,20-dione + NADP+
-
-
-
?
17alpha-methylestr-4-en-3-one + NADPH
17alpha-methylestran-3-one + NADP+
-
-
-
?
17alpha-methylestr-4-en-3-one + NADPH
17alpha-methylestran-3-one + NADP+
-
-
-
?
17beta-hydroxyandrost-4-en-3-one + NADPH
17beta-hydroxy-5beta-androstan-3-one + NADP+
-
trivial name testosterone
-
?
17beta-hydroxyandrost-4-en-3-one + NADPH
17beta-hydroxy-5beta-androstan-3-one + NADP+
-
trivial name testosterone
-
?
17beta-hydroxyandrost-4-en-3-one + NADPH
17beta-hydroxy-5beta-androstan-3-one + NADP+
-
trivial name testosterone
-
?
17beta-hydroxyestr-4-en-3-one + NADPH
17-hydroxyestran-3-one + NADP+
-
-
-
?
17beta-hydroxyestr-4-en-3-one + NADPH
17-hydroxyestran-3-one + NADP+
-
-
-
?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
-
-
-
?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
-
-
-
?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
-
-
-
-
?
androst-4-en-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
-
-
-
?
androst-4-en-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
-
-
-
?
androst-4-en-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
-
-
-
?
cortexone + NADPH
21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
-
-
-
?
cortexone + NADPH
21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
-
-
-
?
cortisol + NADPH
11beta,17,21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
-
-
-
?
cortisol + NADPH
11beta,17,21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
-
-
-
?
cortisone + NADPH + H+
17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+
-
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
high substrate specificity
-
ir
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
-
-
-
?
deoxycorticosterone + NADPH
pregnan-21-ol-3,20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
no substrate inhibition observed
-
-
?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
-
-
ir
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
5alpha-pregnane-3,20-dione, the 5alpha-isomer of the pregnane-3,20-dione is not formed
-
-
ir
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
stereospecific reduction of the 4-double-bond in cardenolide biosynthesis
-
-
?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
highest substrate specificity
-
-
ir
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
substrate of splice variant AKR1D1-002
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
-
?
additional information
?
-
pregnenolone, 21-OH-pregenenolone and isoprogesterone are not accepted by recombinant 5beta-POR
-
-
?
additional information
?
-
-
pregnenolone, 21-OH-pregenenolone and isoprogesterone are not accepted by recombinant 5beta-POR
-
-
?
additional information
?
-
-
AKR1D1 catalyzes the stereospecific reduction of the delta4-double-bond of circulating steroid hormones that contain the delta4-3-ketosteroid functionality, e.g. the reduction of testosteron, progesterone and cortisol to yield the corresponding 5-dihydrosteroid
-
-
?
additional information
?
-
-
aldo-keto reductases are a major superfamily of monomeric NADPH-dependent carbonyl oxidoreductases, active site contains conserved residues D50, Y55, K84, and H117
-
-
?
additional information
?
-
-
the steroid 5beta-reductases catalyze a reaction that is unique in steroid enzymology since the resultant product contains a cis-A/B ring configuration and accordingly contains a 90° bend, the cis-A/B ring configuration is an essential characteristic of cardiac glycosides, e.g. digioxin and bile acids and their precursors
-
-
?
additional information
?
-
-
the recombinant enzyme catalyzes the stereospecific reduction of the delta4-double bond of several steroids with a 3-oxo,delta4,5 structure
-
-
?
additional information
?
-
AKR1D1 catalyzes reduction of DELTA4-ene double bonds in steroid hormones and bile acid precursors. Determination of reaction mechanism by mutational analysis revealing that the 4-pro-R hydride is transferred from the re-face of the nicotinamide ring to C5 of the steroid substrate. E120, a unique substitution in the AKR catalytic tetrad, permits a deeper penetration of the steroid substrate into the active site to promote optimal reactant positioning. It participates with Y58 to create a superacidic oxyanion hole for polarization of the C3 ketone, no role for K87 in the proton relay, overview
-
-
?
additional information
?
-
-
AKR1D1 catalyzes reduction of DELTA4-ene double bonds in steroid hormones and bile acid precursors. Determination of reaction mechanism by mutational analysis revealing that the 4-pro-R hydride is transferred from the re-face of the nicotinamide ring to C5 of the steroid substrate. E120, a unique substitution in the AKR catalytic tetrad, permits a deeper penetration of the steroid substrate into the active site to promote optimal reactant positioning. It participates with Y58 to create a superacidic oxyanion hole for polarization of the C3 ketone, no role for K87 in the proton relay, overview
-
-
?
additional information
?
-
the large steroid-binding site of this enzyme also contains a subsite in which the androstenedione molecule is bound, steroid-binding cavity structure of h5 beta-red, structure comparison
-
-
?
additional information
?
-
-
the large steroid-binding site of this enzyme also contains a subsite in which the androstenedione molecule is bound, steroid-binding cavity structure of h5 beta-red, structure comparison
-
-
?
additional information
?
-
-
AKR1D1 catalyzes the central 5beta-reduction step and reduces bile acid precursors such as DELTA4-cholesten-7alpha-ol-3-one and DELTA 4-cholestene-7alpha,12alpha-diol-3-one to 5beta-cholestan-7alpha-ol-3-one and 5beta-cholestane-7alpha,12alpha-diol-3-one, respectively
-
-
?
additional information
?
-
-
substrate specificity of homogeneous human recombinant AKR1D1 using C18, C19, C21, and C27 DELTA4-ketosteroids, AKR1D1 proficiently reduces all the steroids tested at physiological pH, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes stereo-specifically reduces the DELTA4 double bond in 3-keto steroids and sterols to yield the 5beta-hydrogenated product
-
-
?
additional information
?
-
the enzyme catalyzes stereo-specifically reduces the DELTA4 double bond in 3-keto steroids and sterols to yield the 5beta-hydrogenated product
-
-
?
additional information
?
-
splice variant AKR1D1-002 efficiently metabolizes glucocorticoids and androgens and decreases receptor activation. Variants AKR1D1-001 and AKR1D1-006 poorly metabolize dexamethasone, but do not metabolize cortisol, prednisolone, testosterone or androstenedione
-
-
-
additional information
?
-
-
splice variant AKR1D1-002 efficiently metabolizes glucocorticoids and androgens and decreases receptor activation. Variants AKR1D1-001 and AKR1D1-006 poorly metabolize dexamethasone, but do not metabolize cortisol, prednisolone, testosterone or androstenedione
-
-
-
additional information
?
-
-
enzyme is involved in the biosynthesis of ecdysteroids, catalyzes the 5beta-reduction of a 3-oxo-DELTA4-diketol to a 3-oxo-5beta-diketol
-
-
?
additional information
?
-
-
enzyme reduces a variety of C19 and C21 steroids, highest activity with aldosterone
-
-
?
