1.1.1.146: 11beta-hydroxysteroid dehydrogenase

This is an abbreviated version, for detailed information about 11beta-hydroxysteroid dehydrogenase, go to the full flat file.

Reaction

an 11beta-hydroxysteroid
+
NADP+
=
an 11-oxosteroid
+
NADPH
+
H+

Synonyms

11 beta-hydroxysteroid dehydrogenase type 1, 11-beta-HSD1, 11-beta-HSD1 (oxidase) NADP+, 11-beta-HSD2, 11-beta-hydroxysteroid dehydrogenase type1, 11-DH, 11-DH2, 11-oxoreductase, 11beta hydroxysteroid dehydrogenase type 1, 11beta-HSD, 11beta-HSD 1, 11beta-HSD type 1, 11beta-HSD1, 11beta-HSD1A, 11beta-HSD2, 11beta-hydroxy steroid dehydrogenase, 11beta-hydroxysteroid dehydrogenase, 11beta-hydroxysteroid dehydrogenase 1, 11beta-hydroxysteroid dehydrogenase isoforms 1, 11beta-hydroxysteroid dehydrogenase type 1, 11beta-hydroxysteroid dehydrogenase type 2, 11beta-hydroxysteroid dehydrogenase type I, 11beta-hydroxysteroid dehydrogenase type-1, 11beta-hydroxysteroid dehydrogenase-1, 11beta-hydroxysteroid dehydrogenases type 1, 11beta-hydroxysteroid-dehydrogenase type I, 11betaHSD1, 11HSD1, beta-hydroxysteroid dehydrogenase, corticosteroid 11-reductase, corticosteroid 11beta-dehydrogenase, dehydrogenase, 11beta-hydroxy steroid, HSD1, HSD11B, Hsd11B2, isozyme 11beta-HSD1, More, NAD-dependent 11-beta-hydroxysteroid dehydrogenase, NADP(+)-dependent 11beta-dehydrogenase, NADP+-dependent 11beta-hydroxysteroid dehydrogenase 1, type 1 11beta-hydroxysteroid dehydrogenase

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.146 11beta-hydroxysteroid dehydrogenase

Substrates Products

Substrates Products on EC 1.1.1.146 - 11beta-hydroxysteroid dehydrogenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-dehydrocortisol + NADP+
1,2-dehydrocortisone + NADPH
show the reaction diagram
-
-
-
-
r
1,2-dehydrocortisone + NADPH
1,2-dehydrocortisol + NADP+
show the reaction diagram
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
11-dehydrocorticosterone + NADPH + H+
corticosterone + NADP+
show the reaction diagram
11-oxo-progesterone + NADPH + H+
11beta-hydroxyprogesterone + NADP+
show the reaction diagram
11alpha-hydroxy-pregn-4-ene-3,20-dione + ?
pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + ?
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
-
i.e. cortisol
-
?
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NADP+
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADPH
show the reaction diagram
11beta,17beta-dihydroxyandrost-4-ene-3-one + ?
17beta-hydroxyandrost-4-ene-3,11-dione + ?
show the reaction diagram
11beta,20alpha-dihydroxypregn-4-ene-3-one + ?
20alpha-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
11beta,20beta-dihydroxypregn-4-ene-3-one + ?
20beta-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + ?
11-dehydro,21-hydroxy-pregn-4-en-3,20-dione + ?
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH + H+
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH + H+
show the reaction diagram
11beta-hydroxy-pregn-4-ene-3,20-dione + ?
pregn-4-ene-3,11,20-trione + ?
show the reaction diagram
11beta-hydroxyandrost-4-ene-3,17-dione + ?
androst-4-ene-3,11,17-trione + ?
show the reaction diagram
11beta-hydroxytestosterone + NAD+
11-oxotestosterone + NADH + H+
show the reaction diagram
-
-
-
-
?
12alpha-fluoro-11-dehydrocorticosterone + NADPH
12alpha-fluoro-corticosterone + NADP+
show the reaction diagram
-
-
-
ir
15-deoxy-D12,14-prostaglandin J2 + NADPH
?
show the reaction diagram
-
isozyme 11beta-HSD1
-
-
?
16alpha-methyl-1,2-dehydrocortisone + NADPH
16alpha-methyl-1,2-dehydrocortisol + NADP+
show the reaction diagram
16alpha-methylcortisol + NADP+
16alpha-methylcortisone + NADPH
show the reaction diagram
-
-
-
-
16alpha-methylcortisone + NADPH
16alpha-methylcortisol + NADP+
show the reaction diagram
16beta-methylcortisol + NADP+
16beta-methylcortisone + NADPH
show the reaction diagram
-
-
-
-
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADPH
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NADP+
show the reaction diagram
17alpha,21-dihydroxypregna-1,4-diene-3,11,20-trione + NADPH
11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione + NADP+
show the reaction diagram
-
i.e. prednisone
i.e. prednisolone
?
2,3-benzoylphenyl-propanoic acid + NADPH
2,3-benzoylphenyl-propanol + NADP+
show the reaction diagram
20alpha-hydroxypregn-4-ene-3-one + ?
20alpha-hydroxypregn-4-ene-3,11-dione + ?
show the reaction diagram
21-hydroxy-pregn-4-en-3,11,20-trione + NADPH
11beta,21-dihydroxypregn-4-en-3,20-dione + NADP+
show the reaction diagram
4-methylnitrosamine-1-(3-pyridiyl)-1-butanone + NADPH
4-methylnitrosamine-1-(3-pyridiyl)-1-butanol + NADP+
show the reaction diagram
-
-
-
-
?
4-methylnitrosamino-1-(3-pyridyl)-1-butanone + NADPH
4-methylnitrosamino-1-(3-pyridyl)-1-butanol + NADP+
show the reaction diagram
-
i.e. NNK, genotoxic compound from tobacco smoke, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184
-
-
r
5,5-dimethyl-3-(3-fluorphenyl)-4-(4-methylsulfonyl)phenyl-2-(5H-furanone)-lactol + NADP+
5,5-dimethyl-3-(3-fluorphenyl)-4-(4-methylsulfonyl)phenyl-2-(5H-furanone)-lactone + NADPH
show the reaction diagram
5alpha-androstane-3beta,7alpha,17beta-triol + NADP+
5alpha-androstane-3beta,7beta,17beta-triol + NADPH
show the reaction diagram
-
interconversion of 7alpha to 7beta isoform, ratio Vmax/Km is 2 pmol min-1 microgramm-1/microMol
-
-
r
5alpha-androstane-3beta,7beta,17beta-triol + NADP+
5alpha-androstane-3beta,7alpha,17beta-triol + NADP
show the reaction diagram
-
interconversion of 7beta to 7alpha isoform, ratio Vmax/Km is 0.5 pmol min-1 microgramm-1/microMol
-
-
r
6-[2-(2-hydroxy-ethylamino)-ethyl]-6H-indeno[1,2-c]isoquinoline-5,11-dione + NADPH
(+)-6-[2-(2-hydroxyethyl)aminoethyl]-5-oxo-11-hydroxy-5,6-dihydro-11H-indeno[1,2-c]isoquinoline + NADP+
show the reaction diagram
-
trivial name oracin, cytostatic drug, 11beta-HSD 1 exhibits enzyme cooperativity for the formation of both hydroxy-enantiomers
24% (+)-stereoisomer
-
?
6-[2-(2-hydroxy-ethylamino)-ethyl]-6H-indeno[1,2-c]isoquinoline-5,11-dione + NADPH + H+
(-)-6-[2-(2-hydroxyethyl)aminoethyl]-5-oxo-11-hydroxy-5,6-dihydro-11H-indeno[1,2-c]isoquinoline + NADP+
show the reaction diagram
-
trivial name oracin, cytostatic drug
76% (-)-stereoisomer
-
?
7-ketodehydroepiandrosterone + 2 NADPH + 2 H+
7alpha-hydroxydehydroepiandrosterone + 7beta-hydroxydehydroepiandrosterone + 2 NADP+
show the reaction diagram
-
-
formation of alpha- and beta-product in almost equal amounts. In presence of hexose-6-phosphate dehydrogenase, the 7keto-substrate is almost fully metabolized and the 7beta-product is preferentially formed
-
?
7-oxo-5alpha-androstane-3beta,17beta-diol + NADPH
5alpha-androstane-3beta,7alpha,17beta-triol + 5alpha-androstane-3beta,7alpha,17beta-triol + NADP+
show the reaction diagram
-
-
-
-
r
7-oxocholesterol + NADPH
7beta-hydroxycholesterol + 7alpha-hydroxycholesterol + NADPH
show the reaction diagram
-
40% and 60%, respectively, in lysates of HEK-293 cells and intact HEK-293 cells expressing 11beta-HSD1
-
r
7-oxocholesterol + NADPH
7beta-hydroxycholesterol + NADP+
show the reaction diagram
7alpha-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
show the reaction diagram
in lysates of HEK-293 cells expressing 11beta-HSD1, no oxidation in intact HEK293 cells expressing 11beta-HSD1
-
-
r
7alpha-hydroxydehydroepiandrosterone + NADP+
7beta-hydroxydehydroepiandrosterone + 7-ketodehydroepiandrosterone + NADPH
show the reaction diagram
-
-
in presence of hexose-6-phosphate dehydrogenase, less substrate is metabolized and accumulation of 7-ketodehydroepiandrosterone is abolished
-
?
7beta-hydroxycholesterol + NADP+
7-oxocholesterol + NADPH
show the reaction diagram
7beta-hydroxydehydroepiandrosterone + NADP+
7alpha-hydroxydehydroepiandrosterone + 7-ketodehydroepiandrosterone + NADPH
show the reaction diagram
-
-
formation of products in almost equal amounts. In presence of hexose-6-phosphate dehydrogenase, less substrate is metabolized and accumulation of 7-ketodehydroepiandrosterone is abolished
-
?
9alpha-fluoro-11-oxoprogesterone + NADPH
9alpha-fluoro-11beta-hydroxyprogesterone + NADP+
show the reaction diagram
-
-
-
ir
9alpha-fluorocortisone + NADPH
9alpha-fluorocortisol + NADP+
show the reaction diagram
androst-4-ene-3,11,17-trione + NADPH
11beta-hydroxyandrost-4-ene-3,17-dione + NADP+
show the reaction diagram
androst-4-ene-3,11,17-trione + NADPH
11beta-hydroxyandrost-4-ene-3,17-one + NADP+
show the reaction diagram
androstenedione + NADPH + H+
testosterone + NADP+
show the reaction diagram
corticosterone + NADP+
11-dehydrocorticosterone + NADPH
show the reaction diagram
corticosterone + NADP+
11-dehydrocorticosterone + NADPH + H+
show the reaction diagram
corticosterone + NADP+
?
show the reaction diagram
-
-
-
-
?
corticosterone + NADPH
corticosterol + NADP+
show the reaction diagram
-
-
-
-
r
corticosterone + NADPH + H+
corticosterol + NADP+
show the reaction diagram
cortisol + NAD+
cortisone + NADH
show the reaction diagram
cortisol + NAD+
cortisone + NADH + H+
show the reaction diagram
cortisol + NADP+
cortisone + NADPH
show the reaction diagram
cortisone + NAD(P)H
cortisol + NAD(P)+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+ + H+
show the reaction diagram
cortisone + NADPH
cortisole + NADP+
show the reaction diagram
-
-
-
-
?
cortisone + NADPH + H+
cortisol + NADP+
show the reaction diagram
dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
dexamethasone + NADP+
11-dehydromethasone + NADPH
show the reaction diagram
metyrapone + NADPH
? + NADP+
show the reaction diagram
-
-
-
r
oracin + NADPH + H+
11-dihydrooracin + NADP+
show the reaction diagram
oracin + NADPH + H+
dihydrooracin + NADP+
show the reaction diagram
-
a cytostatic drug, isozyme 11beta-HSD1, carbonyl reductase activity, EC 1.1.1.184, stereochemical ratio of 3:1 for R:S enantiomers of the pro-chiral carbonyl centre of oracin, inactivation of the anti-cancer drug
-
-
r
pregn-4-ene-3,11,20-trione + NADPH
11beta-hydroxy-pregn-4-ene-3,20-dione + NADP+
show the reaction diagram
additional information
?
-