Information on EC 1.1.1.B40 - 11beta-hydroxysteroid dehydrogenase (NAD+)

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The enzyme appears in 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+)
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an 11beta-hydroxysteroid + NAD+ = an 11-oxosteroid + NADH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
redox reaction
-
-
reduction
-
-
SYSTEMATIC NAME
IUBMB Comments
11beta-hydroxysteroid:NAD+ 11-oxidoreductase
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene 11beta-HSDsf, enzyme short form; Japanese eel, gene 11beta-HSDsf
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
type 2 enzyme
-
-
Manually annotated by BRENDA team
isozyme 11beta-HSD1; isozyme 11beta-HSD1
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Ovis aries aries
sheep, isoform 11beta-HSD2
-
-
Manually annotated by BRENDA team
isozyme 11beta-HSD2
-
-
Manually annotated by BRENDA team
isoform 11beta-HSD2
-
-
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
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NAD+
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADH
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH
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-hydroxytestosterone + NAD+
11-oxotestosterone + NADH
show the reaction diagram
-
-
-
?
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADH
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NAD+
show the reaction diagram
1beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH
show the reaction diagram
-
i.e. corticosterone, no reductase activity in aldosterone-sensitive collecting duct
-
-
ir
7-oxocholesterol + NADPH
7alpha-hydroxycholesterol + NADP+
show the reaction diagram
isozyme 11beta-HSD1, stereospecific reaction
-
-
?
7-oxocholesterol + NADPH
7beta-hydroxycholesterol + NADP+
show the reaction diagram
corticosterone + NAD+
11-dehydrocorticosterone + NADH
show the reaction diagram
cortisol + NAD+
cortisone + NADH
show the reaction diagram
cortisol + NAD+
cortisone + NADH + H+
show the reaction diagram
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
dexamethasone + NAD+
11-dehydromethasone + NADH
show the reaction diagram
additional information
?
-
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
11-dehydrocorticosterone + NADPH
corticosterone + NADP+
show the reaction diagram
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NAD+
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADH
show the reaction diagram
11beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH
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-hydroxytestosterone + NAD+
11-oxotestosterone + NADH
show the reaction diagram
Q05KC1
-
-
-
?
17,21-dihydroxy-pregn-4-ene-3,11,20-trione + NADH
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione + NAD+
show the reaction diagram
1beta,21-dihydroxypregn-4-en-3,20-dione + NAD+
21-hydroxy-pregn-4-en-3,11,20-trione + NADH
show the reaction diagram
-
i.e. corticosterone, no reductase activity in aldosterone-sensitive collecting duct
-
-
ir
corticosterone + NAD+
11-dehydrocorticosterone + NADH
show the reaction diagram
cortisol + NAD+
cortisone + NADH
show the reaction diagram
cortisone + NADPH
cortisol + NADP+
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
NADPH
additional information
-
NADH, no substrate affinity
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-gossypol
(+/-)-gossypol
(-)-gossypol
(1S,2R,3S,5R,6R)-4-methylidene-1-([(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl)-7-oxabicyclo[4.1.0]heptane-2,3,5-triol
-
-
(1S,2R,5R,6R)-4-(hydroxymethyl)-1-([(1S,4aR,6S,8aR)-6-hydroxy-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
-
-
(1S,2R,5R,6R)-4-(hydroxymethyl)-1-([(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
-
-
(2E,4S)-4-hydroxy-5-[(1S,5S,6S)-6-(hydroxymethyl)-2-methylidenebicyclo[3.1.1]hept-6-yl]-2-methylpent-2-enoic acid
-
-
(2S)-5-(acetyloxy)-2-hydroxypentyl acetate
-
-
(3alpha,18beta,20beta)-11-oxo-3-trifluoromethylsulfonylaminoolean-12-en-29-oic acid
-
-
(3alpha,18beta,20beta)-3-(acetylamino)-11-oxo-olean-12-en-29-oicacid
-
-
(3alpha,18beta,20beta)-3-methoxyamino-11-oxo-olean-12-en-29-oic acid
-
-
(3alpha,18beta,20beta)-3-methylsulfonylamino-11-oxo-olean-12-en-29-oic acid
-
-
(3beta)-3-(acetyloxy)-11-oxoolean-12-en-30-oic acid
-
-
(3beta)-3-hydroxy-11-oxoolean-12-en-30-amide
-
-
(3beta)-3-hydroxy-18,29-epoxyolean-12-ene-11,29-dione
-
IC50 value for isoform 11beta-HSD2 above 25 microM. Docking studies into isoforms 11beta-HSD1 and 11beta-HSD2 binding sites
(3beta)-3-hydroxyandrost-5-en-17-one
-
treatment of rats induces a shift from isoform 11beta-HSD1 to 11beta-HSD2 expression, increasing conversion from active to inactive glucocorticoids. Dehydroepiandrosterone likely modulates the transcription of 11beta-HSD2 in a phosphatidylinositol-3 kinase/Akt-dependent manner by increasing CCAAT/enhancer-binding protein beta mRNA and protein expression
(3beta)-3-[(3-carboxypropanoyl)oxy]urs-12-en-28-oic acid
-
IC50 value for isoform 11beta-HSD2 above 3 microM. Docking studies into isoforms 11beta-HSD1 and 11beta-HSD2 binding sites
(3beta)-30-[hydroxy(methyl)amino]-11,30-dioxoolean-12-en-3-yl acetate
-
IC50 value for isoform 11beta-HSD1 above 1 microM. Docking studies into isoforms 11beta-HSD1 and 11beta-HSD2 binding sites
(3beta)-N,3-dihydroxy-11-oxoolean-12-en-30-amide
-
-
(3beta,18beta,20beta)-11-oxo-3-succinylamino-olean-12-en-29-oic acid
-
-
(3beta,18beta,20beta)-11-oxo-3-trifluoromethylsulfonylaminoolean-12-en-29-oic acid
-
-
(3beta,18beta,20beta)-3,N-dihydroxy-N-methyl-11-oxo-olean-12-en-29-amide
-
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(3beta,18beta,20beta)-3-(2-carboxy-ethylsulfonylamino)-11-oxoolean-12-en-29-oic acid
-
-
(3beta,18beta,20beta)-3-(2-methoxycarbonyl-ethylsulfonylamino)-11-oxo-olean-12-en-29-oic acid
-
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(3beta,18beta,20beta)-3-(acetylamino)-11-oxo-olean-12-en-29-oic acid
-
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(3beta,18beta,20beta)-3-acetoxy-N-hydroxy-11-oxo-olean-12-en-29-amide
-
-
(3beta,18beta,20beta)-3-acetoxy-N-methoxy-11-oxo-olean-12-en-29-amide
-
-
(3beta,18beta,20beta)-3-acetoxy-N-methyl-N-hydroxy-11-oxoolean-12-en-29-amide
-
-
(3beta,18beta,20beta)-3-acetylamino-N-hydroxy-N-methyl-11-oxoolean-12-en-29-amide
-
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(3beta,18beta,20beta)-3-amino-11-oxoolean-12-en-29-oic acid, diphenylmethyl ester
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(3beta,18beta,20beta)-3-hydroxy-N-methoxy-11-oxo-olean-12-en-29-amide
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(3beta,18beta,20beta)-3-methoxyamino-11-oxo-olean-12-en-29-oic acid
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(3beta,18beta,20beta)-3-methylsulfonylamino-11-oxo-olean-12-en-29-oic acid
-
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(3beta,18beta,20beta)-N-hydroxy-N-methyl-11-oxo-3-[(trifluoromethylsulfonyl)amino]-olean-12-en-29-amide
-
-
(3beta,18beta,20beta)-N-hydroxy-N-methyl-3-methoxyamino-11-oxo-olean-12-en-29-amide
-
-
(3E)-3-(methoxyimino)-11-oxoolean-12-en-30-oic acid
-
-
(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-11-[(methylsulfonyl)amino]-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl acetate
-
IC50 value for isoform 11beta-HSD1 above 40 microM. Docking studies into isoforms 11beta-HSD1 and 11beta-HSD2 binding sites
(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
11-Dehydrocorticosterone
-
inhibition of isozyme 11beta-HSD2
11-dehydrocortisterone
-
-
11-deoxycorticosterone
11-oxo-3beta,5alpha-tetrathydrotestosterone
-
-
11-oxo-allopregnanolone
-
inhibition of both isozymes 11beta-HSD1 and of isozyme 11beta-HSD2
11-oxo-progesterone
-
-
11-oxo-testosterone
-
-
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione
-
i.e. cortisol
11beta,21-dihydroxypregn-4-en-3,20-dione
-
11-beta-HSD2, 50% inhibition at 0.00001 mM
11beta-hydroxy-allopregnanolone
-
-
11beta-hydroxyandrostanediol
-
-
11beta-hydroxyandrostenedione
-
-
11beta-hydroxyprogesterone
-
-
11beta-hydroxytestosterone
-
inhibition of both isozymes 11beta-HSD1 and of isozyme 11beta-HSD2
17beta-estradiol
-
decrease in isoform HSD2 protein in male, but not female, fetal lung explant
18beta-glycyrrhetinic acid
-
inhibits both 11beta-HSD1 and 11beta-HSD2, but preferentially inhibits 11beta-HSD2
2'-hydroxyflavanone
2-oxopentane-1,5-diyl diacetate
3,11-dioxoolean-12-en-30-oic acid
-
-
3,5-dimethyladamantylmethyl
-
3-((3r,5r,7r)-adamantan-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
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
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
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
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
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
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
3-(tricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine
3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate
-
IC50 in the presence of NADP+: 0.12 mM, IC50 in the presence of NAD+: 5.6 mM; i.e. CHAPS
3alpha,5alpha-tetrahydro-11-dehydrocorticosterone
-
-
3alpha,5alpha-tetrahydro-dehydrocortisterone
-
-
3alpha,5alpha-tetrahydroaldosterone
-
-
3alpha,5alpha-tetrahydrocorticosterone
-
inhibition of isozyme 11beta-HSD1 and isozyme isozyme 11beta-HSD2
3alpha,5alpha-tetrahydrocortisol
-
-
3beta-hydroxy-11-oxo-18beta-olean-12-en-30-oic-acid
4-n-octylphenol
-
inhibition of kidney isozyme 11beta-HSD2, IC50: 0.0235 mM
4-nonylphenol
-
inhibition of liver isozyme 11beta-HSD1 and kidney isozyme 11beta-HSD2, 11beta-HSD1 IC50: 49.3 mM, isozyme 11beta-HSD2 IC50: 0.0203 mM
4-pregnen-11,17-diol-3,20-dione
Ovis aries aries
-
IC50: 0.00035 mM
4-pregnen-11alpha-ol-3,20-dione
Ovis aries aries
-
IC50: 0.0001 mM
4-pregnen-11beta-ol-3,20-dione
Ovis aries aries
-
IC50: 0.00005 mM
4-pregnen-16alpha-ol-3,20-dione
Ovis aries aries
-
not inhibitory
4-pregnen-17,21-diol-3,20-dione
Ovis aries aries
-
not inhibitory
4-pregnen-17alpha,20alpha-diol-3-one
Ovis aries aries
-
not inhibitory
4-pregnen-17alpha-ol-3,20-dione
Ovis aries aries
-
IC50: 0.047 mM
4-pregnen-20alpha-ol-3-one
Ovis aries aries
-
IC50: 0.007 mM
4-pregnen-20beta-ol-3-one
Ovis aries aries
-
IC50: 0.008 mM
4-pregnen-21-ol-3,20-dione
Ovis aries aries
-
IC50: 0.001 mM
4-pregnen-3,11,20-trione
Ovis aries aries
-
IC50: 0.0004 mM
4-pregnen-3,20-dione
Ovis aries aries
-
IC50: 0.0011 mM
4-t-octylphenol
-
inhibition of kidney isozyme 11beta-HSD2, IC50: 0.0089 mM
5-hydroxy-4-oxopentyl acetate
5-pregnen-3beta,11beta-diol-20-one
Ovis aries aries
-
IC50: 0.0001 mM
5alpha-dihydrocorticosterone
-
-
5alpha-pregnan-11alpha-ol-3,20-dione
Ovis aries aries
-
IC50: 0.00035 mM
5alpha-pregnan-11beta,17alpha,21-triol-3,20-dione
Ovis aries aries
-
IC50: 0.0031 mM
5alpha-pregnan-11beta,21-diol-3,20-dione
Ovis aries aries
-
IC50: 0.00015 mM
5alpha-pregnan-3alpha,11beta,17alpha,21-tetrol-20-one
Ovis aries aries
-
IC50: 0.008 mM
5alpha-pregnan-3alpha,11beta,21-triol-20-one
Ovis aries aries
-
IC50: 0.00026 mM
5alpha-pregnan-3alpha,11beta-diol-20-one
Ovis aries aries
-
IC50: 0.00012 mM
5alpha-pregnan-3alpha,17alpha,21-triol-11,20-dione
Ovis aries aries
-
IC50: 0.0055 mM
5alpha-pregnan-3alpha,21-diol-11,20-dione
Ovis aries aries
-
IC50: 0.0008 mM
5alpha-Pregnan-3alpha,21-diol-20-one
Ovis aries aries
-
IC50: 0.0024 mM
5alpha-pregnan-3alpha-ol-20-one
Ovis aries aries
-
IC50: 0.008 mM
5beta-pregnan-3alpha,11alpha-diol-20-one
Ovis aries aries
-
not inhibitory
5beta-pregnan-3alpha,11beta,17alpha,21-tetrol-20-one
Ovis aries aries
-
not inhibitory
5beta-pregnan-3alpha,11beta,21-triol-20-one
Ovis aries aries
-
not inhibitory
5beta-pregnan-3alpha,11beta-diol-20-one
Ovis aries aries
-
not inhibitory
5beta-Pregnan-3alpha,21-diol-20-one
Ovis aries aries
-
not inhibitory
5beta-Pregnan-3alpha-ol-20-one
Ovis aries aries
-
not inhibitory
A23187
-
inhibits isozyme 11beta-HSD2 strongly
abietic acid
adamantyl triazole
-
adamantyl triazoles
-
aldosterone
BVT-14225
-
isozyme 11beta-HSD1 IC50: 52 nM, 1000fold less potent against isozyme 11beta-HSD2
carbenoxolone
chenodeoxycholic acid
cholic acid
-
IC50: 3.529 mM
curcumin
-
inhibitory against isoform 11beta-HSD2 in intact cells with IC50 value of 14.56 microM
dexamethasone
-
-
di-n-butyl phthalate
di-n-octyl phthalate
di-n-pentyl phthalate
dicyclohexyl phthalate
diethyl phthalate
dipropyl phthalate
end-products
-
inhibition at high levels
-
estradiol
-
50% inhibition, DTT protects at 10 mM, estradiol has a regulatory function on the isozymes in the liver
Ethacrynic acid
-
IC50: 0.452 mM
flavanone
forskolin
-
slight inhibitory effect in absence of interleukin-1beta
Furosemide
-
IC50: 0.059 mM, competitive
glycyrrhetinic acid
glycyrrhizinic acid
-
-
glycyrrhizininc acid
-
-
Interleukin-1beta
-
inhibits isozyme 11beta-HSD2, forskolin acts antagonistically strongly
-
interleukin-1beta or tissue necrosis factor-alpha simultaneously increase 11beta-HSD1 expression and down-regulate 11beta-HSD2
-
mono (2-ethylhexyl) phthalate
mono-(2-ethylhexyl) phthalate
-
mono-(2-ethylhexyl) phthalate inhibits mRNA level and enzyme activity of 11beta-HSD2 in LbetaT2 cells at 0.0001 mM
n-alkyl-substituted adamantyl triazoles
-
NADP+
-
50% inhibition at 220 nmol
naringenin
-
IC50: 0.336 mM
naringin
-
IC50: 2.373 mM
Nifed
-
inhibits isozyme 11beta-HSD2 slightly
perfluorooctane sulfonate
Phenylbutazone
-
IC50: 1.358 mM
progesterone
sistosterol
-
IC50: 1.395 mM
SQ-22536
-
inhibits isozyme 11beta-HSD2
sterenin A
-
isoindoline alkaloid inhibitor isolated from Stereum sp. SANK 21205
sterenin B
-
isoindoline alkaloid inhibitor isolated from Stereum sp. SANK 21205
sterenin C
-
isoindoline alkaloid inhibitor isolated from Stereum sp. SANK 21205
sterenin D
-
isoindoline alkaloid inhibitor isolated from Stereum sp. SANK 21205
stigmasterol
-
IC50: 1.968 mM
T0504
tributyltin
-
inhibition of kidney isozyme 11beta-HSD2, IC50: 0.0165 mM
Triphenyltin
-
inhibition of kidney isozyme 11beta-HSD2, IC50: 0.0033 mM
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17alpha,20beta-dihydroxy-4-pregnen-3-one
activates in immature testis
dexamethasone
-
after application of dexamethasone, 11beta-HSD1 mRNA increases in muscle of both diabetic and control subjects, whereas 11beta-HSD2 mRNA decreases. 11beta-HSD1 activity increases in diabetic subjects, but not in controls, whereas 11beta-HSD2 activity does not change in either group
prostaglandin E2
-
stimulation of progesterone production and of 11beta-hydroxysteroid dehydrogenase activity via the prostaglandin E receptor 2-cAMP signalling pathway in luteinizing granulosa cells
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00038 - 0.00085
11-Dehydrocorticosterone
0.000047 - 0.008
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione
0.0000051 - 0.00108
11beta,21-dihydroxypregn-4-en-3,20-dione
0.00089
17,21-dihydroxy-pregn-4-ene-3,11,20-trione
-
i.e. cortisone, temperature not specified in the publication, pH 5.5-6
0.0022
21-hydroxy-pregn-4-en-3,11,20-trione
-
temperature not specified in the publication, pH 5.5-6
0.000047 - 0.00028
corticosterone
0.000154 - 0.00136
cortisol
0.00052 - 0.00157
cortisone
0.0000044 - 0.091
NAD+
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002 - 0.2
2'-hydroxyflavanone
0.0021 - 0.011
abietic acid
0.00011 - 0.00094
carbenoxolone
0.00055 - 0.035
chenodeoxycholic acid
0.0012 - 0.2
flavanone
0.000028 - 0.00044
glycyrrhetinic acid
0.0018
progesterone
-
probably minimal physiological importance
0.000006 - 0.0018
T0504
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00061 - 0.00105
(+)-gossypol
0.00088 - 0.00105
(+/-)-gossypol
0.00133 - 0.0019
(-)-gossypol
0.0000049
(3alpha,18beta,20beta)-3-methoxyamino-11-oxo-olean-12-en-29-oic acid
Homo sapiens
-
pH not specified in the publication, 37C
0.00075
(3beta)-3-(acetyloxy)-11-oxoolean-12-en-30-oic acid
Homo sapiens
-
pH not specified in the publication, 37C
0.0000029
(3beta)-30-[hydroxy(methyl)amino]-11,30-dioxoolean-12-en-3-yl acetate
Homo sapiens
-
pH 7.4, 37C
0.000122
(3beta)-N,3-dihydroxy-11-oxoolean-12-en-30-amide
Homo sapiens
-
pH not specified in the publication, 37C
0.000458
(3beta,18beta,20beta)-3-(acetylamino)-11-oxo-olean-12-en-29-oic acid
Homo sapiens
-
pH not specified in the publication, 37C
0.0000611
(3beta,18beta,20beta)-3-acetoxy-N-hydroxy-11-oxo-olean-12-en-29-amide
Homo sapiens
-
pH not specified in the publication, 37C
0.0000029
(3beta,18beta,20beta)-3-acetoxy-N-methyl-N-hydroxy-11-oxoolean-12-en-29-amide
Homo sapiens
-
pH not specified in the publication, 37C
0.00213
(3beta,18beta,20beta)-3-hydroxy-N-methoxy-11-oxo-olean-12-en-29-amide
Homo sapiens
-
pH not specified in the publication, 37C
0.0000145
(3beta,18beta,20beta)-3-methoxyamino-11-oxo-olean-12-en-29-oic acid
Homo sapiens
-
pH not specified in the publication, 37C
0.000268
(3E)-3-(methoxyimino)-11-oxoolean-12-en-30-oic acid
Homo sapiens
-
pH not specified in the publication, 37C
0.0000069
(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-11-[(methylsulfonyl)amino]-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl acetate
Homo sapiens
-
pH 7.4, 37C
0.00047
11-dehydrocortisterone
Ovis aries
-
pH 8.4, 37C
0.001
11-deoxycorticosterone
Ovis aries aries
-
IC50: 0.001 mM
0.008
11-oxo-3beta,5alpha-tetrathydrotestosterone
Ovis aries
-
pH 8.4, 37C
0.0015
11-oxo-allopregnanolone
Ovis aries
-
pH 8.4, 37C
0.0004
11-oxo-progesterone
Ovis aries
-
pH 8.4, 37C
0.00135
11-oxo-testosterone
Ovis aries
-
pH 8.4, 37C
0.000061
11beta,17,21-trihydroxy-pregn-4-ene-3,20-dione
Homo sapiens
-
i.e. cortisol, pH and temperature not specified in the publication
0.0000051
11beta,21-dihydroxypregn-4-en-3,20-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.00012
11beta-hydroxy-allopregnanolone
Ovis aries
-
pH 8.4, 37C
0.0045
11beta-hydroxyandrostanediol
Ovis aries
-
pH 8.4, 37C
0.0078
11beta-hydroxyandrostenedione
Ovis aries
-
pH 8.4, 37C
0.00005
11beta-hydroxyprogesterone
Ovis aries
-
pH 8.4, 37C
0.00035
11beta-hydroxytestosterone
Ovis aries
-
pH 8.4, 37C
0.000257
18beta-glycyrrhetinic acid
Homo sapiens
-
37C, pH not specified in the publication
0.000329
3,11-dioxoolean-12-en-30-oic acid
Homo sapiens
-
pH not specified in the publication, 37C
5.6
3-[(3-cholamidopropyl)dimethylammonio]-1-propanesulfonate
Homo sapiens
-
pH and temperature not specified in the publication
0.0008
3alpha,5alpha-tetrahydro-dehydrocortisterone
Ovis aries
-
pH 8.4, 37C
0.0005
3alpha,5alpha-tetrahydroaldosterone
Ovis aries
-
pH 8.4, 37C
0.00026
3alpha,5alpha-tetrahydrocorticosterone
Ovis aries
-
pH 8.4, 37C
0.008
3alpha,5alpha-tetrahydrocortisol
Ovis aries
-
pH 8.4, 37C
0.000097 - 0.254
3beta-hydroxy-11-oxo-18beta-olean-12-en-30-oic-acid
0.0235
4-n-octylphenol
Homo sapiens
-
inhibition of kidney isozyme 11beta-HSD2, pH 7.4, 37C
0.0203
4-nonylphenol
Homo sapiens
-
inhibition of kidney isozyme 11beta-HSD2, pH 7.4, 37C
0.00035
4-pregnen-11,17-diol-3,20-dione
Ovis aries aries
-
IC50: 0.00035 mM
0.0001
4-pregnen-11alpha-ol-3,20-dione
Ovis aries aries
-
IC50: 0.0001 mM
0.00005
4-pregnen-11beta-ol-3,20-dione
Ovis aries aries
-
IC50: 0.00005 mM
0.047
4-pregnen-17alpha-ol-3,20-dione
Ovis aries aries
-
IC50: 0.047 mM
0.007
4-pregnen-20alpha-ol-3-one
Ovis aries aries
-
IC50: 0.007 mM
0.008
4-pregnen-20beta-ol-3-one
Ovis aries aries
-
IC50: 0.008 mM
0.001
4-pregnen-21-ol-3,20-dione
Ovis aries aries
-
IC50: 0.001 mM
0.0004
4-pregnen-3,11,20-trione
Ovis aries aries
-
IC50: 0.0004 mM
0.0011
4-pregnen-3,20-dione
Ovis aries aries
-
IC50: 0.0011 mM
0.0089
4-t-octylphenol
Homo sapiens
-
inhibition of kidney isozyme 11beta-HSD2, pH 7.4, 37C
0.0001
5-pregnen-3beta,11beta-diol-20-one
Ovis aries aries
-
IC50: 0.0001 mM
0.00015
5alpha-dihydrocorticosterone
Ovis aries
-
pH 8.4, 37C
0.00035
5alpha-pregnan-11alpha-ol-3,20-dione
Ovis aries aries
-
IC50: 0.00035 mM
0.0031
5alpha-pregnan-11beta,17alpha,21-triol-3,20-dione
Ovis aries aries
-
IC50: 0.0031 mM
0.00015
5alpha-pregnan-11beta,21-diol-3,20-dione
Ovis aries aries
-
IC50: 0.00015 mM
0.008
5alpha-pregnan-3alpha,11beta,17alpha,21-tetrol-20-one
Ovis aries aries
-
IC50: 0.008 mM
0.00026
5alpha-pregnan-3alpha,11beta,21-triol-20-one
Ovis aries aries
-
IC50: 0.00026 mM
0.00012
5alpha-pregnan-3alpha,11beta-diol-20-one
Ovis aries aries
-
IC50: 0.00012 mM
0.0055
5alpha-pregnan-3alpha,17alpha,21-triol-11,20-dione
Ovis aries aries
-
IC50: 0.0055 mM
0.0008
5alpha-pregnan-3alpha,21-diol-11,20-dione
Ovis aries aries
-
IC50: 0.0008 mM
0.0024
5alpha-Pregnan-3alpha,21-diol-20-one
Ovis aries aries
-
IC50: 0.0024 mM
0.008
5alpha-pregnan-3alpha-ol-20-one
Ovis aries aries
-
IC50: 0.008 mM
0.00002 - 0.00005
carbenoxolone
0.513
chenodeoxycholic acid
Cavia porcellus
-
IC50: 0.513 mM
3.529
cholic acid
Cavia porcellus
-
IC50: 3.529 mM
0.0089
dexamethasone
Homo sapiens
-
pH and temperature not specified in the publication
0.01369
di-n-butyl phthalate
Rattus norvegicus
-
-
0.03264 - 0.0465
dicyclohexyl phthalate
0.08559
dipropyl phthalate
Rattus norvegicus
-
-
0.452
Ethacrynic acid
Cavia porcellus
-
IC50: 0.452 mM
0.059
Furosemide
Cavia porcellus
-
IC50: 0.059 mM, competitive
0.0000024 - 0.000257
glycyrrhetinic acid
0.00000071
glycyrrhizinic acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00000071
glycyrrhizininc acid
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.1108 - 0.1218
mono (2-ethylhexyl) phthalate
0.0168 - 0.3279
mono-(2-ethylhexyl) phthalate
0.336
naringenin
Cavia porcellus
-
IC50: 0.336 mM
2.373
naringin
Cavia porcellus
-
IC50: 2.373 mM
0.000048 - 0.000293
perfluorooctane sulfonate
1.358
Phenylbutazone
Cavia porcellus
-
IC50: 1.358 mM
1.395
sistosterol
Cavia porcellus
-
IC50: 1.395 mM
0.01
sterenin A
Homo sapiens
-
value above, pH not specified in the publication, 26C
0.01
sterenin B
Homo sapiens
-
value above, pH not specified in the publication, 26C
0.01
sterenin C
Homo sapiens
-
value above, pH not specified in the publication, 26C
0.01
sterenin D
Homo sapiens
-
value above, pH not specified in the publication, 26C
1.968
stigmasterol
Cavia porcellus
-
IC50: 1.968 mM
0.0165
tributyltin
Homo sapiens
-
inhibition of kidney isozyme 11beta-HSD2, pH 7.4, 37C
0.0033
Triphenyltin
Homo sapiens
-
inhibition of kidney isozyme 11beta-HSD2, pH 7.4, 37C
additional information
(1S,2R,3S,5R,6R)-4-methylidene-1-([(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl)-7-oxabicyclo[4.1.0]heptane-2,3,5-triol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 6
-
oxidase activity
6.5
-
reductase activity
8
-
assay at
8.4
-
assay at
9
-
oxidase activity
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 10
-
11-dehydrogenase activity, broad range of pH optimum
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at room temperature
26
-
assay at
28
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
rectum, sigmoid colon
Manually annotated by BRENDA team
-
presence of 11beta-hydroxysteroid dehydrogenase mRNA transcripts and protein in all tissues of the reproductive tract examined, but cortison-cortisol interconversion is undetectable in the corpus and cauda epididymides, vas deferens, vesicular and prostate glands
Manually annotated by BRENDA team
-
aldosterone-sensitive, NAD+ specificity
Manually annotated by BRENDA team
-
presence of 11beta-hydroxysteroid dehydrogenase mRNA transcripts and protein in all tissues of the reproductive tract examined, but cortison-cortisol interconversion is undetectable in the corpus and cauda epididymides, vas deferens, vesicular and prostate glands
Manually annotated by BRENDA team
-
expression of mRNA for 11beta-hydroxysteroid dehydrogenase type 1, 11beta-hydroxysteroid dehydrogenase type 2 and for glucocorticoid receptor during the estrous cycle. Level of 11beta-hydroxysteroid dehydrogenase type 1 mRNA is higher at the regressed state than at the other stages, whereas level of 11beta-hydroxysteroid dehydrogenase type 2 mRNA is lower at the regressed stage than at the other stages
Manually annotated by BRENDA team
-
epithelium
Manually annotated by BRENDA team
-
of normotensive and hypertensive rats, the latter are hyperthrophied and fibrotic and have structural alterations in the coronary circulation, expression of isozymes 11beta-HSD1 and 11beta-HSD2, overview
Manually annotated by BRENDA team
-
11beta-HSD2, but not 11beta-HSD1, is strongly expressed in LbetaT2 cells
Manually annotated by BRENDA team
-
of neonatal pig. High expression of 11beta-hydroxysteroid dehydrogenase type 2 mRNA, resulting in oxidation from cortisol to cortison, with no detection of the reduction reaction. Activity of type 2 enzyme is higher than the oxidation activity of the type 1 enzyme
Manually annotated by BRENDA team
-
peripheral lymph nodes and mesenteric lymph nodes
Manually annotated by BRENDA team
-
lung epithelial cell line, isozymes HSD1 and HSD2
Manually annotated by BRENDA team
-
expression and activity of isozyme 11beta-HSD2 in probes of seven different women with ovarian cancer of different types, overview
Manually annotated by BRENDA team
-
high level of expression and activity
Manually annotated by BRENDA team
-
highly expressed
Manually annotated by BRENDA team
-
renal cortical collecting duct cell line
Manually annotated by BRENDA team
-
mainly isozyme 11beta-HSD2, the concentration of isozyme 11beta-HSD1 is 10-100fold lower, expression analysis, isozyme 11beta-HSD2 shows strong expression and activity in quiescent cells
Manually annotated by BRENDA team
-
at baseline, mRNA levels are similar in diabetic and control sugjects for 11beta-HSD1, 11beta-HSD2, and hexose-6-phosphate dehydrogenase. 11beta-HSD1 activity is reduced in diabetic subjects, while 11beta-HSD2 activity is increased. After application of dexamethasone, 11beta-HSD1 mRNA increases in both groups, whereas 11beta-HSD2 mRNA decreases. 11beta-HSD1 activity increases in diabetic subjects, but not in controls, whereas 11beta-HSD2 activity does not change in either group; mRNA levels are similar in diabetic and control subjects for 11beta-hydroxysteroid dehydrogenase 1 and 11beta-hydroxysteroid dehydrogenase 2. 11beta-Hydroxysteroid dehydrogenase 2-activity is higher in diabetic patients. After treatment with dexamethasone, 11beta-hydroxysteroid dehydrogenase 1-mRNA increases in both groups, whereas 11beta-hydroxysteroid dehydrogenase 2-mRNA decreases. 11beta-Hydroxysteroid dehydrogenase 1-activity increases in diabetic patients, but not in control, whereas 11beta-hydroxysteroid dehydrogenase 2-activity does not change in either group
Manually annotated by BRENDA team
-
low levels of mRNA
Manually annotated by BRENDA team
-
isoform 11beta-HSD1 is clearly expressed while isoform 11beta-HSD2 is much less prominent, 11beta-HSD1 protein expression predominates in endothelial cells and varies during periods of growth
Manually annotated by BRENDA team
-
NAD+-dependent 11beta-hydroxysteroid dehydrogenase activity
Manually annotated by BRENDA team
-
splanchnic activity
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
isozyme 11beta-HSD2
Manually annotated by BRENDA team
additional information
-
subcellular localization of isozyme 11beta-HSD2, overview, isozyme 11beta-HSD2 activity and plasma corticosterone are determined in toads from pre- (PR), post- (P), and reproductive (R) periods, overview
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000
x * 32000, recombinant isozyme 11beta-HSD1, SDS-PAGE
36000
-
x * 36000, calculated
42000
-
11beta-HSD2, SDS-PAGE
44140
-
x * 44140, calculation from cDNA sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer or trimer
-
x * 40000, isozyme HSD2, SDS-PAGE
additional information
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
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 0.01 M sodium phosphate, pH 7.4, 0.25 M sucrose, 6 weeks
-
-20C, cytosol depleted fraction, 10 mM phosphate buffer, 0.25 M sucrose, stable for 2 days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli by nickel affinity chromatography and gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in HEK-293 cell
expression in CHO cells
-
expression in CHOP-C4 cells
-
expression in HEK-293 cell
-
expression in Xenopus oocytes
-
expression of FLAG-tagged isozyme 11beta-HSD1 in HEK-293 cells
expression of His6-tagged enzyme in Escherichia coli
-
expression of isozyme 11beta-HSD1 in HEK-293 cells
gene 11beta-HSDsf, DNA and amino acid sequence determination and analysis, in vitro expression of the enzyme using the wheat germ cell-free protein synthesis system
gene HSD11B2, DNA and amino acid sequence determination and analysis, microsatellite genotyping
-
isoform 11beta-HSD2, expression in Sf9 cell
-
isozyme 11beta-HSD1, expression in HEK-293 cells
overexpressed in HEK-293 cell
-
stable expression of isozymes 11beta-HSD1 and 11beta-HSD2 in CHO cells
-
the 11beta-HSD2 enzyme is produced in HEK-293 cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
isozyme expression analysis
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
the enzyme is a target for inhibitor design and development; the enzyme is a target for inhibitor design and development
medicine
pharmacology
-
the enzyme is an important therapeutic target for diabetes in humans