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Information on EC 1.1.1.B40 - 11beta-hydroxysteroid dehydrogenase (NAD+) and Organism(s) Mus musculus and UniProt Accession P51661
for references in articles please use BRENDA:EC1.1.1.B40preliminary BRENDA-supplied EC number
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1.1.1.B40 11beta-hydroxysteroid dehydrogenase (NAD+)Specify your search results
Word Map
- 1.1.1.B40
- glucocorticoid
-
mineralocorticoid
- cortisone
- aldosterone
- hypertension
- adrenal
- 11-dehydrocorticosterone
- dexamethasone
- urinary
- fetal
- carbenoxolone
-
glycyrrhetinic
- 11beta-hsds
-
beta-hsd1
- nadp
- acth
- renin
- hypokalemia
- spironolactone
- tetrahydrocortisol
-
cortisol-cortisone
-
liquorice
- thf
-
adrenalectomized
-
cushing
-
11-keto
-
beta-reductase
-
glycyrrhizic
-
hypopituitary
- medicine
-
3hcorticosterone
-
prereceptor
- pharmacology
-
11-beta-hydroxysteroid
-
feto-placental
-
low-renin
- drug development
-
11-dehydro
-
oxo-reductase
The taxonomic range for the selected organisms is: Mus musculus
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
11 beta-hydroxysteroid dehydrogenase, 11 beta-hydroxysteroid dehydrogenase type 2, 11beta-hsd type 2, 11beta-ohsd, 11beta-hsd 2, 11-beta hydroxysteroid dehydrogenase type 2, 11beta hydroxysteroid dehydrogenase type 2, type 2 11beta-hydroxysteroid dehydrogenase, 11beta-hydroxysteroid dehydrogenase type-2, nad(+)-dependent 11beta-dehydrogenase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an 11beta-hydroxysteroid + NAD+ = an 11-oxosteroid + NADH + H+
substrate binding site structure, reaction mechanism involving Lys187 and Tyr183, active site structure involving a S-Y-K catalytic triad
-
an 11beta-hydroxysteroid + NAD+ = an 11-oxosteroid + NADH + H+
the three-dimensional organization of the hydrophobic substrate binding pocket is responsible for species-specific variability of activity with different substrates, overview
-
SYSTEMATIC NAME
IUBMB Comments
11beta-hydroxysteroid:NAD+ 11-oxidoreductase
-
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
cortisol + NAD+
cortisone + NADH
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
-
isozyme 11beta-HSD1
-
-
?
7-oxocholesterol + NADPH + H+
7beta-hydroxycholesterol + NADP+
-
isozyme 11beta-HSD1, stereospecific reaction
-
-
?
cortisol + NAD+
cortisone + NADH
-
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
corticosterone + NAD+
11-dehydrocorticosterone + NADH + H+
-
-
-
-
ir
corticosterone + NAD+
11-dehydrocorticosterone + NADH + H+
-
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
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
cortisol + NAD+
cortisone + NADH
isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+
-
-
ir
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
-
isozyme 11beta-HSD1
-
-
?
corticosterone + NAD+
11-dehydrocorticosterone + NADH + H+
-
-
-
-
ir
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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-(adamantan-1-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
isozyme 11beta-HSD1 IC50: 98 nM, isozyme 11beta-HSD2 IC50: above 0.01 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 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
-
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
-
-
(4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
-
-
(4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a,6-tetramethyl-3,4,4a,5,8,8a-hexahydronaphthalen-2(1H)-one
-
-
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
-
mono-(2-ethylhexyl) phthalate inhibits mRNA level and enzyme activity of 11beta-HSD2 in LbetaT2 cells at 0.0001 mM
additional information
-
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
LITERATURE
IMAGE
additional information
-
interleukin-1beta or tissue necrosis factor-alpha simultaneously increase 11beta-HSD1 expression and down-regulate 11beta-HSD2
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00038
11-Dehydrocorticosterone
-
pH 7.4, 37°C, recombinant isozyme 11beta-HSD1
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.019
2'-hydroxyflavanone
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.0064
abietic acid
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.00011
carbenoxolone
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.0025
chenodeoxycholic acid
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.034
flavanone
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.00012
glycyrrhetinic acid
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
0.000082
T0504
-
pH 7.4, 37°C, isozyme 11beta-HSD1, inhibition of cortisol oxidation
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
(4aS,5R,8aR)-5,6-bis(hydroxymethyl)-1,1,4a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
0.0168
mono-(2-ethylhexyl) phthalate
Mus musculus
-
11beta-HSD2 from LbetaT2 cell microsomes, in PBS (pH 7.4), at 37°C
0.3279
mono-(2-ethylhexyl) phthalate
Mus musculus
-
11beta-HSD2 from kidney microsomes, in PBS (pH 7.4), at 37°C
additional information
(4aS,5R,8aR)-5,6-bis(hydroxymethyl)-1,1,4a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
Mus musculus
-
IC50 = 0.2505 mg/ml, pH not specified in the publication, temperature not specified in the publication
additional information
(4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol
Mus musculus
-
IC50 = 0.3303 mg/ml, pH not specified in the publication, temperature not specified in the publication
additional information
(4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a,6-tetramethyl-3,4,4a,5,8,8a-hexahydronaphthalen-2(1H)-one
Mus musculus
-
IC50 = 0.5002 mg/ml, pH not specified in the publication, temperature not specified in the publication
additional information
2-oxopentane-1,5-diyl diacetate
Mus musculus
-
IC50 = 0.0323 mg/ml, pH not specified in the publication, temperature not specified in the publication
additional information
5-hydroxy-4-oxopentyl acetate
Mus musculus
-
IC50 = 0.1291 mg/ml, pH not specified in the publication, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
11beta-HSD2 in the adult brain is thought to protect mineralocorticoid receptors from inactivation by corticosterone
-
11beta-HSD2, but not 11beta-HSD1, is strongly expressed in LbetaT2 cells
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli by nickel affinity chromatography and gel filtration
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pharmacology
-
the enzyme is an important therapeutic target for diabetes in humans
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Holmes, M.C.; Yau, J.L.W.; Kotelevtsev, Y.; Mullins, J.J.; Seckl, J.R.
11beta-Hydroxysteroid dehydrogenases in the brain: two enzymes two roles
Ann. N. Y. Acad. Sci.
1007
357-366
2003
Mus musculus, Rattus norvegicus
Zhang, J.; Osslund, T.D.; Plant, M.H.; Clogston, C.L.; Nybo, R.E.; Xiong, F.; Delaney, J.M.; Jordan, S.R.
Crystal structure of murine 11 beta-hydroxysteroid dehydrogenase 1: an important therapeutic target for diabetes
Biochemistry
44
6948-6957
2005
Mus musculus
Olson, S.; Aster, S.D.; Brown, K.; Carbin, L.; Graham, D.W.; Hermanowski-Vosatka, A.; LeGrand, C.B.; Mundt, S.S.; Robbins, M.A.; Schaeffer, J.M.; Slossberg, L.H.; Szymonifka, M.J.; Thieringer, R.; Wright, S.D.; Balkovec, J.M.
Adamantyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type 1
Bioorg. Med. Chem. Lett.
15
4359-4362
2005
Mus musculus (P51661), Homo sapiens (P80365)
Arampatzis, S.; Kadereit, B.; Schuster, D.; Balazs, Z.; Schweizer, R.A.; Frey, F.J.; Langer, T.; Odermatt, A.
Comparative enzymology of 11beta-hydroxysteroid dehydrogenase type 1 from six species
J. Mol. Endocrinol.
35
89-101
2005
Canis lupus familiaris, Cavia porcellus (Q6QLL4), Homo sapiens (P28845), Homo sapiens (P80365), Mesocricetus auratus (Q6R0J2), Mus musculus, Rattus norvegicus
Hong, D.; Li, X.W.; Lian, Q.Q.; Lamba, P.; Bernard, D.J.; Hardy, D.O.; Chen, H.X.; Ge, R.S.
Mono-(2-ethylhexyl) phthalate (MEHP) regulates glucocorticoid metabolism through 11beta-hydroxysteroid dehydrogenase 2 in murine gonadotrope cells
Biochem. Biophys. Res. Commun.
389
305-309
2009
Mus musculus
Chapman, K.E.; Coutinho, A.E.; Gray, M.; Gilmour, J.S.; Savill, J.S.; Seckl, J.R.
The role and regulation of 11beta-hydroxysteroid dehydrogenase type 1 in the inflammatory response
Mol. Cell. Endocrinol.
301
123-131
2009
Homo sapiens, Mus musculus
Xu, D.; Sheng, Y.; Zhou, Z.Y.; Liu, R.; Leng, Y.; Liu, J.K.
Sesquiterpenes from cultures of the basidiomycete Clitocybe conglobata and their 11 beta-hydroxysteroid dehydrogenase inhibitory activity
Chem. Pharm. Bull.
57
433-435
2009
Homo sapiens, Mus musculus
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