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1.1.1.B40: 11beta-hydroxysteroid dehydrogenase (NAD+)

This is an abbreviated version!
For detailed information about 11beta-hydroxysteroid dehydrogenase (NAD+), go to the full flat file.

Word Map on EC 1.1.1.B40

Reaction

an 11beta-hydroxysteroid
+
NAD+
=
an 11-oxosteroid
 +
NADH
 +
H+

Synonyms

11 beta-hydroxysteroid dehydrogenase, 11 beta-hydroxysteroid dehydrogenase type 2, 11-beta hydroxysteroid dehydrogenase type 1, 11-beta hydroxysteroid dehydrogenase type 2, 11-beta-HSD2, 11beta hydroxysteroid dehydrogenase type 2, 11beta-HSD, 11beta-HSD 2, 11beta-HSD type 2, 11beta-HSD1, 11beta-HSD2, 11beta-HSD2 (oxidase) NAD+, 11beta-HSD2/HSD11B2, 11beta-hydroxysteroid dehydrogenase 2, 11beta-hydroxysteroid dehydrogenase isoforms 2, 11beta-hydroxysteroid dehydrogenase type 1, 11beta-hydroxysteroid dehydrogenase type 2, 11beta-hydroxysteroid dehydrogenase type-2, 11beta-hydroxysteroid dehydrogenases type 2, 11beta-OHSD, 11betaHSD2, 11HSD1, 7-alpha-HCD, 7-alpha-hydroxycholesterol dehydrogenase, corticosteroid 11-beta-dehydrogenase isozyme 1, HSD 2, HSD11B type 1, HSD11B type 2, Hsd11B2, isozyme 11beta-HSD2, More, NAD(+)-dependent 11beta-dehydrogenase, NAD+-dependent 11beta-hydroxysteroid dehydrogenase 2, type 2 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.B40 11beta-hydroxysteroid dehydrogenase (NAD+)

Inhibitors

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

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INHIBITOR
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
-
-
(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
-
-
(3beta,18beta,20beta)-3-(acetylamino)-11-oxo-olean-12-en-29-oic acid
-
-
(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
-
-
(3beta,18beta,20beta)-3-amino-11-oxoolean-12-en-29-oic acid, diphenylmethyl ester
-
-
(3beta,18beta,20beta)-3-hydroxy-N-methoxy-11-oxo-olean-12-en-29-amide
-
-
(3beta,18beta,20beta)-3-methoxyamino-11-oxo-olean-12-en-29-oic acid
-
-
(3beta,18beta,20beta)-3-methylsulfonylamino-11-oxo-olean-12-en-29-oic acid
-
-
(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-((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-(3,5-dimethyladamantylmethyl)-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-(adamantan-1-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine
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 triazoles
-
aldosterone
BVT-14225
-
isozyme 11beta-HSD1 IC50: 52 nM, 1000fold less potent against isozyme 11beta-HSD2
carbenoxolone
Cd2+
the ERK1/2 inhibitor U0126 can block cadmium-induced inhibition of placental 11beta-HSD2. Cadmium does not alter activities of p38 MAPK, JNK, or PI3 kinase. Cadmium specifically activates the ERK1/2 signaling pathway in human trophoblast cells
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
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
-