Information on EC 1.1.1.B40 - 11beta-hydroxysteroid dehydrogenase (NAD+) and Organism(s) Mus musculus and UniProt Accession P51661

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Mus musculus
UNIPROT: P51661


The taxonomic range for the selected organisms is: Mus musculus

The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.1.1.B40
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
11beta-hydroxysteroid dehydrogenase (NAD+)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an 11beta-hydroxysteroid + NAD+ = an 11-oxosteroid + NADH + H+
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
11beta-hydroxysteroid:NAD+ 11-oxidoreductase
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isozymes 11beta-HSD1 and 11beta-HSD2
SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
cortisol + NAD+
cortisone + NADH
show the reaction diagram
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
-
isozyme 11beta-HSD1
-
-
?
7-oxocholesterol + NADPH
7beta-hydroxycholesterol + NADP+
show the reaction diagram
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isozyme 11beta-HSD1, stereospecific reaction
-
-
?
corticosterone + NAD+
11-dehydrocorticosterone + NADH
show the reaction diagram
cortisol + NAD+
cortisone + NADH
show the reaction diagram
-
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
cortisol + NAD+
cortisone + NADH + H+
show the reaction diagram
-
-
-
-
?
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cortisol + NAD+
cortisone + NADH
show the reaction diagram
P51661
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
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isozyme 11beta-HSD1
-
-
?
corticosterone + NAD+
11-dehydrocorticosterone + NADH
show the reaction diagram
-
-
-
-
ir
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
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isozyme 11beta-HSD1, activation
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
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NADPH
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-((3r,5r,7r)-adamantan-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 74 nM, isozyme 11beta-HSD2 IC50: 0.004 mM
3-(3,4,7-trimethyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 180 nM, isozyme 11beta-HSD2 IC50: 0.004 mM
3-(3,4-dimethyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 13 nM, isozyme 11beta-HSD2 IC50: 0.00255 mM
3-(3,5-dimethyladamantylmethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 36 nM, isozyme 11beta-HSD2 IC50: 0.0176 mM
3-(3-bromotricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 23 nM, isozyme 11beta-HSD2 IC50: 0.004 mM
3-(3-fluorotricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 37 nM, isozyme 11beta-HSD2 IC50: 0.004 mM
3-(3-phenyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 2.3 nM, isozyme 11beta-HSD2 IC50: 23 nM
3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)tricyclo[3.3.1.13,7]decan-1-ol
isozyme 11beta-HSD1 IC50: 739 nM, isozyme 11beta-HSD2 IC50: 0.004 mM
3-(tricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
isozyme 11beta-HSD1 IC50: 7.7 nM, isozyme 11beta-HSD2 IC50: 0.004 mM
adamantyl triazole
isozyme 11beta-HSD1 IC50: 7.8 nM, isozyme 11beta-HSD2 IC50: above 0.003 mM
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adamantyl triazoles
eight derivatives of different ring size, IC50 of 1.4-2180 nM for isozyme 11beta-HSD1, and of 8.7-2000 nM for isozyme 11beta-HSD2, the IC50 value decreases with increasing ring size, overview
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n-alkyl-substituted adamantyl triazoles
substituted with methyl to butyl groups, IC50: of 3-72 nM for isozyme 11beta-HSD1, and of about 0.004 mM for isozyme 11beta-HSD2, overview
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(4aS,5R,8aR)-5,6-bis(hydroxymethyl)-1,1,4a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
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(4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
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(4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a,6-tetramethyl-3,4,4a,5,8,8a-hexahydronaphthalen-2(1H)-one
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2'-hydroxyflavanone
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2-oxopentane-1,5-diyl diacetate
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5-hydroxy-4-oxopentyl acetate
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abietic acid
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carbenoxolone
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chenodeoxycholic acid
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flavanone
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glycyrrhetinic acid
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interleukin-1beta or tissue necrosis factor-alpha simultaneously increase 11beta-HSD1 expression and down-regulate 11beta-HSD2
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mono-(2-ethylhexyl) phthalate
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mono-(2-ethylhexyl) phthalate inhibits mRNA level and enzyme activity of 11beta-HSD2 in LbetaT2 cells at 0.0001 mM
T0504
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additional information
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inhibitory effects in intact cells and IC50 values, overview, structure-based pharmacophore models for isozyme 11beta-HSD1 inhibitors using crystal structure 1XU7, 1XU9, and 2 BEL
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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interleukin-1beta or tissue necrosis factor-alpha simultaneously increase 11beta-HSD1 expression and down-regulate 11beta-HSD2
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00038
11-Dehydrocorticosterone
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pH 7.4, 37C, recombinant isozyme 11beta-HSD1
0.00052
cortisone
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pH 7.4, 37C, recombinant isozyme 11beta-HSD1
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.019
2'-hydroxyflavanone
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.0064
abietic acid
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.00011
carbenoxolone
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.0025
chenodeoxycholic acid
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.034
flavanone
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.00012
glycyrrhetinic acid
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.000082
T0504
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pH 7.4, 37C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0168 - 0.3279
mono-(2-ethylhexyl) phthalate
additional information
(4aS,5R,8aR)-5,6-bis(hydroxymethyl)-1,1,4a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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11beta-HSD2 in the adult brain is thought to protect mineralocorticoid receptors from inactivation by corticosterone
Manually annotated by BRENDA team
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11beta-HSD2, but not 11beta-HSD1, is strongly expressed in LbetaT2 cells
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
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peripheral lymph nodes and mesenteric lymph nodes
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
33000
-
x * 33000, recombinant isozyme 11beta-HSD1, SDS-PAGE
42000
-
11beta-HSD2, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 33000, recombinant isozyme 11beta-HSD1, SDS-PAGE
additional information
-
structure molecular modeling
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified recombinant His6-tagged enzyme, hanging drop vapour diffusion method, 25 mg/ml protein in 20 mM Tris-HCl, pH 8.0, 0.2 M NaCl, 0.1& Triton, 5% glycerol, and 2 mM EDTA, mixed with equal volume of well solution containing 1.8 M Li2O4, and 0.1 M HEOES, pH 7.5, at room temperature, derivatization with 1 mM ethylmercuric chloride, soaking of crystals with NADH and corticoserone containing solution, X-ray diffraction structure determination and analysis at 3.0 A resolution
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli by nickel affinity chromatography and gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in HEK-293 cell
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expression of His6-tagged enzyme in Escherichia coli
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isozyme 11beta-HSD1, expression in HEK-293 cells
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pharmacology
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the enzyme is an important therapeutic target for diabetes in humans