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Information on EC 1.3.1.3 - DELTA4-3-oxosteroid 5beta-reductase
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1.3.1.3 DELTA4-3-oxosteroid 5beta-reductaseIUBMB Comments
The enzyme from human efficiently catalyses the reduction of progesterone, androstenedione, 17alpha-hydroxyprogesterone and testosterone to 5beta-reduced metabolites; it can also act on aldosterone, corticosterone and cortisol, but to a lesser extent . The bile acid intermediates 7alpha,12alpha-dihydroxy-4-cholesten-3-one and 7alpha-hydroxy-4-cholesten-3-one can also act as substrates .
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Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
akr1d1, 5beta-por, h5beta-red, progesterone 5beta-reductase, p5betar, steroid 5beta-reductase, srd5beta, aldo-keto reductase 1d1, 3-oxo-delta4-steroid 5beta-reductase, akr1d4, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3-oxo-DELTA4-steroid 5beta-reductase
4,5beta-dihydrocortisone:NADP+ DELTA4-oxidoreductase
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5-beta-reductase
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5beta-POR
AKR1D1
androstenedione 5beta-reductase
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cortisone 5beta-reductase
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cortisone beta-reductase
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DELTA 4-5beta-reductase
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DELTA4-3-ketosteroid 5beta-reductase
DELTA4-hydrogenase
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EC 1.3.1.23
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formerly
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P5betaR
progesterone 5beta-reductase
reductase, cholestenone 5beta.-
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reductase, cortisone DELTA4-5beta-
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steroid 5beta-reductase
steroid 5beta.-reductase
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testosterone 5-beta-reductase
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testosterone 5beta-reductase
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additional information
DELTA4-3-ketosteroid 5beta-reductase
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additional information
human 5beta-red belongs to the aldo-keto reductase, AKR, superfamily and is the first member of the 1D subfamily, AKR1D1
additional information
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cortisone 5beta-reduction (EC 1.3.1.3) and androstenedione reduction (EC 1.3.1.23) are catalyzed by the same catalytic site of a single protein
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+ = cortisone + NADPH + H+
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17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+ = cortisone + NADPH + H+
reaction mechanism, overview
17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+ = cortisone + NADPH + H+
catalyzes the reduction of the DELTA4 double bond of DELTA4-3-ketosteroids, converting those steroids into 5beta-dihydro-3-ketosteroids
5beta-cholestan-3-one + NADP+ = cholest-4-en-3-one + NADPH + H+
mechanism, Schiff-base intermediate not involved
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5beta-cholestan-3-one + NADP+ = cholest-4-en-3-one + NADPH + H+
reaction mechanism, overview
5beta-cholestan-3-one + NADP+ = cholest-4-en-3-one + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
reduction
redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
5beta-cholestan-3-one:NADP+ 4,5-oxidoreductase
The enzyme from human efficiently catalyses the reduction of progesterone, androstenedione, 17alpha-hydroxyprogesterone and testosterone to 5beta-reduced metabolites; it can also act on aldosterone, corticosterone and cortisol, but to a lesser extent [8]. The bile acid intermediates 7alpha,12alpha-dihydroxy-4-cholesten-3-one and 7alpha-hydroxy-4-cholesten-3-one can also act as substrates [9].
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CAS REGISTRY NUMBER
COMMENTARY
37255-35-9
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9029-08-7
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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
(20S)-21-hydroxy-20-methylpregn-4-en-3-one + NADPH + H+
? + NADP+
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-
-
?
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+
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-
-
?
4-androstene-3,17-dione + NADPH + H+
5beta-androstan-3,17-dione + NADP+
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-
?
7alpha,12alpha-dihydroxy-4-cholesten-3-one + NADPH
7alpha,12alpha-dihydroxy-5-beta-cholestan-3-one + NADP+
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?
7alpha,12beta-dihydroxy-4-cholesten-3-one + NADPH + H+
(5beta,7alpha,12beta)-7,12-dihydroxycholestan-3-one + NADP+
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?
7alpha-hydroxy-4-cholesten + NADPH
7alpha-hydroxy-5beta-cholestan-3-one + NADP+
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?
7alpha-hydroxy-4-cholesten-3-one + NADPH
(5beta,7alpha)-7-hydroxycholestan-3-one + NADP+
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?
7alpha-hydroxy-4-cholesten-3-one + NADPH + H+
7alpha-hydroxy-5beta-cholestan-3-one + NADP+
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r
cortisol + NADPH + H+
11beta,17,21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
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?
DELTA 4-cholestene-7alpha,12alpha-diol-3-one + NADPH + H+
5beta-cholestane-7alpha,12alpha-diol-3-one + NADP+
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a bile acid intermediate
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?
DELTA4-cholesten-7alpha-ol-3-one + NADPH + H+
5beta-cholestan-7alpha-ol-3-one + NADP+
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a bile acid intermediate
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?
dexamethasone + NADPH + H+
? + NADP+
substrate of splice variant AKR1D1-002
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?
prednisolone + NADPH + H+
? + NADP+
substrate of splice variant AKR1D1-002
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?
11beta,17alpha,21-trihydroxy-pregn-4-en-3,20-dione + NADPH
11beta,17alpha,21-trihydroxypregnan-3,20-dione + NADP+
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?
11beta,17alpha,21-trihydroxy-pregn-4-en-3,20-dione + NADPH
11beta,17alpha,21-trihydroxypregnan-3,20-dione + NADP+
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?
17alpha,21-dihydroxy-pregn-4-en-3,20-dione + NADPH
17alpha,21-dihydroxy-pregnan-3,20-dione + NADP+
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?
17alpha,21-dihydroxy-pregn-4-en-3,20-dione + NADPH
17alpha,21-dihydroxy-pregnan-3,20-dione + NADP+
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?
17alpha-methylestr-4-en-3-one + NADPH
17alpha-methylestran-3-one + NADP+
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?
17alpha-methylestr-4-en-3-one + NADPH
17alpha-methylestran-3-one + NADP+
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?
17beta-hydroxyandrost-4-en-3-one + NADPH
17beta-hydroxy-5beta-androstan-3-one + NADP+
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trivial name testosterone
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?
17beta-hydroxyandrost-4-en-3-one + NADPH
17beta-hydroxy-5beta-androstan-3-one + NADP+
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trivial name testosterone
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?
17beta-hydroxyandrost-4-en-3-one + NADPH
17beta-hydroxy-5beta-androstan-3-one + NADP+
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trivial name testosterone
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?
17beta-hydroxyestr-4-en-3-one + NADPH
17-hydroxyestran-3-one + NADP+
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?
17beta-hydroxyestr-4-en-3-one + NADPH
17-hydroxyestran-3-one + NADP+
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?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
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?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
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?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
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?
androst-4-en-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
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?
androst-4-en-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
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?
androst-4-en-3,17-dione + NADPH
5beta-androstan-3,17-dione + NADP+
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?
cortexone + NADPH
21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
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?
cortexone + NADPH
21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
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?
cortisol + NADPH
11beta,17,21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
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?
cortisol + NADPH
11beta,17,21-trihydroxy-5beta-pregnane-3,20-dione + NADP+
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?
cortisone + NADPH + H+
17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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high substrate specificity
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ir
cortisone + NADPH + H+
5beta-17,21dihydroxy-pregnan-3,11,20-trione + NADP+
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?
deoxycorticosterone + NADPH
pregnan-21-ol-3,20-dione + NADP+
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?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
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?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
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no substrate inhibition observed
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?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
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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
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ir
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
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stereospecific reduction of the 4-double-bond in cardenolide biosynthesis
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?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
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highest substrate specificity
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ir
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
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?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
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?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
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?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
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?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
substrate of splice variant AKR1D1-002
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?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
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?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
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?
additional information
?
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pregnenolone, 21-OH-pregenenolone and isoprogesterone are not accepted by recombinant 5beta-POR
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?
additional information
?
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pregnenolone, 21-OH-pregenenolone and isoprogesterone are not accepted by recombinant 5beta-POR
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?
additional information
?
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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
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?
additional information
?
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aldo-keto reductases are a major superfamily of monomeric NADPH-dependent carbonyl oxidoreductases, active site contains conserved residues D50, Y55, K84, and H117
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?
additional information
?
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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
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?
additional information
?
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the recombinant enzyme catalyzes the stereospecific reduction of the delta4-double bond of several steroids with a 3-oxo,delta4,5 structure
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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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
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?
additional information
?
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the enzyme catalyzes stereo-specifically reduces the DELTA4 double bond in 3-keto steroids and sterols to yield the 5beta-hydrogenated product
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?
additional information
?
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the enzyme catalyzes stereo-specifically reduces the DELTA4 double bond in 3-keto steroids and sterols to yield the 5beta-hydrogenated product
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?
additional information
?
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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
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additional information
?
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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
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additional information
?
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enzyme is involved in the biosynthesis of ecdysteroids, catalyzes the 5beta-reduction of a 3-oxo-DELTA4-diketol to a 3-oxo-5beta-diketol
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?
additional information
?
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enzyme reduces a variety of C19 and C21 steroids, highest activity with aldosterone
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?
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NATURAL SUBSTRATE
NATURAL 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
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
-
-
?
4-androstene-3,17-dione + NADPH
5beta-androstan-3,17-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+
-
-
-
-
?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5beta-pregnane-3,20-dione + NADP+
-
stereospecific reduction of the 4-double-bond in cardenolide biosynthesis
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
(5beta,17beta)-17-hydroxyandrostan-3-one + NADP+
-
-
-
?
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
?
-
-
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
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-
?
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
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH