Information on EC 1.14.15.4 - steroid 11beta-monooxygenase

New: Word Map on EC 1.14.15.4
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Search Reference ID:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


The expected taxonomic range for this enzyme is: Opisthokonta

EC NUMBER
COMMENTARY hide
1.14.15.4
-
RECOMMENDED NAME
GeneOntology No.
steroid 11beta-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a steroid + 2 reduced adrenodoxin + O2 + 2 H+ = an 11beta-hydroxysteroid + 2 oxidized adrenodoxin + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
glucocorticoid biosynthesis
-
-
Metabolic pathways
-
-
mineralocorticoid biosynthesis
-
-
Steroid hormone biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
steroid,reduced-adrenal-ferredoxin:oxygen oxidoreductase (11beta-hydroxylating)
A heme-thiolate protein (P-450). Also hydroxylates steroids at the 18-position, and converts 18-hydroxycorticosterone into aldosterone.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-66-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain IBL02
-
-
Manually annotated by BRENDA team
strain IBL02
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Boedijn NRRL 2380
-
-
Manually annotated by BRENDA team
gene cyp11b, a protogynous hermaphroditic fish
UniProt
Manually annotated by BRENDA team
gene CYP11B
-
-
Manually annotated by BRENDA team
sole protogynous freshwater fish found that exhibits an adult sex change from functional females to males
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
although the active site pocket is lined by identical residues between CYP11B isoforms, most of the divergent residues that confer additional 18-oxidase activity of aldosterone synthase are located in the I-helix, vicinity of the O2 activation path and loops around the H-helix, affecting an egress channel closure required for retaining intermediates in the active site; although the active site pocket is lined by identical residues between CYP11B isoforms, most of the divergent residues that confer additional 18-oxidase activity of aldosterone synthase are located in the I-helix, vicinity of the O2 activation path and loops around the H-helix, affecting an egress channel closure required for retaining intermediates in the active site
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11-deoxy-cortisol + reduced ferredoxin + O2
cortisol + ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
11-deoxycorticosterone + adrenal ferredoxin + H2O
corticosterone + reduced adrenal ferredoxin + O2
show the reaction diagram
-
-
-
-
?
11-deoxycorticosterone + NADPH + O2
18-hydroxycorticosterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
11-deoxycorticosterone + reduced adrenal ferredoxin + 2 H+ + 2 O2
aldosterone + oxidized adrenal ferredoxin + 2 H2O
show the reaction diagram
11-deoxycorticosterone + reduced adrenal ferredoxin + O2
18-hydroxycorticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
11-deoxycorticosterone + reduced adrenal ferredoxin + O2
?
show the reaction diagram
-
-
-
?
11-deoxycorticosterone + reduced adrenal ferredoxin + O2
corticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
11-deoxycorticosterone + reduced adrenodoxin + O2
corticosterone + oxidized adrenodoxin + H2O
show the reaction diagram
11-deoxycortisol + adrenal ferredoxin + H2O
cortisol + reduced adrenal ferredoxin + O2
show the reaction diagram
-
-
-
-
?
11-deoxycortisol + NADPH + O2
cortisol + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
11-deoxycortisol + reduced adrenal ferredoxin + O2
14alpha-hydroxy-11-deoxycortisol + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
11alpha-hydroxylase activity
-
?
11-deoxycortisol + reduced adrenal ferredoxin + O2
cortisol + adrenal ferredoxin + H2O
show the reaction diagram
11-deoxycortisol + reduced adrenal ferredoxin + O2
cortisol + oxidized adrenal ferredoxin + H2O
show the reaction diagram
11-deoxycortisol + reduced adrenodoxin + O2
cortisol + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
16,17alpha-epoxyprogesterone + reduced adrenal ferredoxin + O2
11beta-hydroxy-16,17alpha-epoxyprogesterone + adrenal ferredoxin + H2O
show the reaction diagram
17alpha,21-dihydroxy-pregn-4-ene-3,20-dione + reduced adrenal ferredoxin + O2
11beta,17alpha,21-trihydroxy-pregn-4-ene-3,20-dione + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
i.e. Reichstein's compound, inducer
hydrocortisone, 60%, 11beta hydroxylation
?
17alpha,21-dihydroxy-pregn-4-ene-3,20-dione + reduced adrenal ferredoxin + O2
14alpha,17alpha,21-trihydroxy-pregn-4-ene-3,20-dione + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
i.e. Reichstein's compound, inducer
25%, 14alpha hydroxylation
?
18-hydroxy-corticosterone + reduced adrenal ferredoxin + O2
aldosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
18-hydroxylation, last 3 steps of pathway for aldosterone biosynthesis
-
?
18-hydroxycorticosterone + reduced adrenal ferredoxin + O2
aldosterone + adrenal ferredoxin + H2O
show the reaction diagram
18-hydroxycorticosterone + reduced adrenal ferredoxin + O2
aldosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
18-hydroxycorticosterone + reduced adrenodoxin + O2
aldosterone + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
18-hydroxycorticosterone + reduced ferredoxin + O2
aldosterone + ferredoxin + H2O
show the reaction diagram
19-hydroxy-11-deoxycorticosterone + reduced adrenal ferredoxin + O2
19-oxo-11-deoxycorticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
-
-
?
4-androstene-3,17-dione + reduced adrenal ferredoxin + O2
11beta-hydroxy-4-androstene-3,17-dione + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
i.e. testosterone, 11beta-/19-hydroxylase activity, good sustrate
-
?
4-androstene-3,17-dione + reduced adrenal ferredoxin + O2
19-hydroxy-4-androstene-3,17-dione + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
i.e. testosterone, 11beta-/19-hydroxylase activity, good sustrate
-
?
4-pregnen-21-ol-3,20-dione + reduced adrenal ferredoxin + O2
4-pregnene-11,21-diol-3,20-dione + oxidized adrenal ferredoxin + H2O
show the reaction diagram
4-pregnene-17,21-diol-3,20-dione + reduced adrenal ferredoxin + O2
4-pregnene-11,17,21-triol-3,20-dione + oxidized adrenal ferredoxin + H2O
show the reaction diagram
a steroid + reduced adrenodoxin + O2
an 11beta-hydroxysteroid + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
androstendione + reduced adrenodoxin + O2
? + oxidized adrenodoxin + H2O
show the reaction diagram
corticosterone + reduced adrenal ferredoxin + O2
11-deoxycorticosterone + adrenal ferredoxin + H2O
show the reaction diagram
corticosterone + reduced adrenal ferredoxin + O2
18-hydroxy-11-deoxycorticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
addition of adrenodoxin and adrenodoxin reductase
-
?
corticosterone + reduced adrenal ferredoxin + O2
18-hydroxy-corticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
18-hydroxylation, last 3 steps of pathway for aldosterone biosynthesis
-
?
corticosterone + reduced adrenal ferredoxin + O2
18-hydroxycorticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
corticosterone + reduced adrenal ferredoxin + O2
aldosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
corticosterone + reduced adrenodoxin + O2
18-hydroxycorticosterone + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
cortisol + reduced adrenal ferredoxin + O2
11-deoxycortisol + adrenal ferredoxin + H2O
show the reaction diagram
cortisol + reduced adrenal ferredoxin + O2
cortisone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
-
-
?
metyrapone + ?
metyrapol + ?
show the reaction diagram
-
plasma, product-stereoselective reductive metabolism
enantiomers
r
progesterone + reduced adrenodoxin + O2
11beta-hydroxyprogesterone + oxidized adrenodoxin + H2O
show the reaction diagram
testosterone + reduced adrenal ferredoxin + O2
11beta-hydroxytestosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
at low rate
-
-
?
testosterone + reduced adrenodoxin + O2
11-hydroxytestosterone + oxidized adrenodoxin + H2O
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-deoxy-cortisol + reduced ferredoxin + O2
cortisol + ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
11-deoxycorticosterone + reduced adrenal ferredoxin + O2
corticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
11beta-hydroxylation, last 3 steps of pathway for aldosterone biosynthesis
-
?
11-deoxycorticosterone + reduced adrenodoxin + O2
corticosterone + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
11-deoxycortisol + adrenal ferredoxin + H2O
cortisol + reduced adrenal ferredoxin + O2
show the reaction diagram
-
-
-
-
?
11-deoxycortisol + reduced adrenal ferredoxin + O2
cortisol + adrenal ferredoxin + H2O
show the reaction diagram
16,17alpha-epoxyprogesterone + reduced adrenal ferredoxin + O2
11beta-hydroxy-16,17alpha-epoxyprogesterone + adrenal ferredoxin + H2O
show the reaction diagram
18-hydroxy-corticosterone + reduced adrenal ferredoxin + O2
aldosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
18-hydroxylation, last 3 steps of pathway for aldosterone biosynthesis
-
?
18-hydroxycorticosterone + reduced adrenal ferredoxin + O2
aldosterone + adrenal ferredoxin + H2O
show the reaction diagram
18-hydroxycorticosterone + reduced adrenodoxin + O2
aldosterone + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
18-hydroxycorticosterone + reduced ferredoxin + O2
aldosterone + ferredoxin + H2O
show the reaction diagram
corticosterone + reduced adrenal ferredoxin + O2
11-deoxycorticosterone + adrenal ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
corticosterone + reduced adrenal ferredoxin + O2
18-hydroxy-corticosterone + oxidized adrenal ferredoxin + H2O
show the reaction diagram
-
18-hydroxylation, last 3 steps of pathway for aldosterone biosynthesis
-
?
corticosterone + reduced adrenodoxin + O2
18-hydroxycorticosterone + oxidized adrenodoxin + H2O
show the reaction diagram
-
-
-
-
?
cortisol + reduced adrenal ferredoxin + O2
11-deoxycortisol + adrenal ferredoxin + H2O
show the reaction diagram
-
in the adrenal zona fasciculata
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
adrenodoxin
ascorbate
-
plus NADH very low conversion and no aldosterone production, in synergism with NADH, malate and NADP+ increase of aldosterone synthetase activity in zona glomerulosa, not zona fasciculate
Ferredoxin
NADP+
-
plus malate supports all 4 conversions, increase of aldosterone synthetase activity
reduced adrenal ferredoxin
additional information
-
cofactor screening, overview, the enzyme is active with NADPH
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
highly activating
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R)-2-[2-[(1S)-1-(4-chlorophenyl)ethyl]-3,3-dioxido-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazin-4-yl]-1-phenylethanol
-
-
(1S)-2-[2-[(1S)-1-(4-chlorophenyl)ethyl]-3,3-dioxido-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazin-4-yl]-1-phenylethanol
-
-
(5Z)-5-(1H-imidazol-5-ylmethylene)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile
-
50% inhibition at 0.0069 mM, selective for CYP11B1
(R)-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile
-
FAD286; FAD286, CYP11B2 inhibitor, inhibited CYP11B2 and CYP11B1 activities
1-(1H-inden-2-yl)-1H-imidazole
-
CYP11B2 IC50: 448 nM, no inhibition of CYP11B1, recombinant enzymes
1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole
-
CYP11B1 IC50: 639 nM, CYP11B2 IC50: 334 nM, recombinant enzymes
1-(3-bromobenzyl)-1H-imidazole
-
-
1-(3-chlorobenzyl)-1H-imidazole
-
-
1-(3-cyanobenzyl)-1H-imidazole
-
-
1-(3-fluorobenzyl)-1H-imidazole
-
-
1-(4-aminobenzyl)-1H-imidazole
-
-
1-(4-bromobenzyl)-1H-imidazole
-
-
1-(4-bromobenzyl)-5-phenyl-1H-imidazole
-
-
1-(4-chlorobenzyl)-1H-imidazole
-
-
1-(4-chlorobenzyl)-5-phenyl-1H-imidazole
-
-
1-(4-cyanobenzyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(2-fluorophenyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(2-methylphenyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(3-fluorophenyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(3-methylphenyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(4-fluorophenyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(4-methylphenyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(4-pyridyl)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(methyl carboxylate)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-(methylene-acetate)-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-bromo-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-formyl-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-hydroxymethyl-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-methyl-1H-imidazole
-
-
1-(4-cyanobenzyl)-5-phenyl-1H-imidazole
-
-
1-(4-fluorobenzyl)-1H-imidazole
-
-
1-(4-fluorobenzyl)-5-phenyl-1H-imidazole
-
-
1-(4-methoxybenzyl)-5-phenyl-1H-imidazole
-
-
1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole
-
CYP11B1 IC50: 763 nM, CYP11B2 IC50: 411 nM, recombinant enzymes
1-benzyl-5-phenyl-1H-imidazole
-
-
11beta-hydroxy-dehydroepiandrosterone
-
50% inhibition at 0.0033 mM
11beta-hydroxy-progesterone
-
50% inhibition at 0.0004 mM
11beta-hydroxy-testosterone
-
50% inhibition at 0.0017 mM
18-ethynylprogesterone
18-vinyldeoxycorticosterone
-
deoxycorticosterone analog, very strong and reversible inhibitor for deoxycorticosterone and corticosterone oxidation, 0.001 mM leads to decrease in corticosterone production with 30% of total activity after 1 min, 100fold more efficient than 18-vinylprogesterone for inhibition of 11beta-hydroxylation step, only 6fold of more inhibition of 18-hydroxylation step
18-vinylprogesterone
2,3-dichloro-N-(pyridin-3-yl)benzamide
-
51% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B22
2,4,5-trifluoro-N-(pyridin-3-yl)benzamide
-
70% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B23
2-(4-chlorobenzyl)-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-(4-fluorobenzyl)-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-benzyl-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-fluoro-N-(pyridin-3-yl)benzamide
-
34% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B19
2-[(1R)-1-(4-chlorophenyl)ethyl]-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-(3-methoxy-2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-(cyclopropylmethyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-[(3-methyloxetan-3-yl)methyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-[(propan-2-yloxy)methyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
3,4-difluoro-N-(pyridin-3-yl)benzamide
-
83% inhibition of CYP11B2 at 0.5 mM, 6% inhibition of CYP11B20
3,4-dimethoxy-N-(pyridin-3-yl)benzamide
-
-
3-(1-benzyl-1H-imidazol-5-yl)-1-propanol
-
-
3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine
-
CYP11B1 IC50: 2117 nM, CYP11B2 IC50: 30 nM, recombinant enzymes
3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine
-
CYP11B1 IC50: 1268 nM, CYP11B2 IC50: 7 nM, recombinant enzymes
3-(1H-imidazol-1-ylmethyl)aniline
-
-
3-(3,4-dihydronaphthalen-2-yl)pyridine
-
CYP11B1 IC50: 1729 nM, CYP11B2 IC50: 7 nM, recombinant enzymes
3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine
-
CYP11B1 IC50: 503 nM, CYP11B2 IC50: 5 nM, recombinant enzymes
3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine
-
CYP11B1 IC50: 1615 nM, CYP11B2 IC50: 176 nM, recombinant enzymes
3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine
-
CYP11B1 IC50: 1291 nM, CYP11B2 IC50: 13 nM, recombinant enzymes
3-(6-methoxy-1H-inden-2-yl)pyridine
-
competitive, CYP11B1 IC50: 5684 nM, CYP11B2 IC50: 4 nM, recombinant enzymes
3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
-
competitive, CYP11B1 IC50: 578 nM, CYP11B2 IC50: 2 nM, recombinant enzymes
3-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
-
CYP11B2 IC50: 45 nM, no inhibition of CYP11B1, recombinant enzymes
3-chloro-N-(pyridin-3-yl)benzamide
-
26% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B18
3-fluoro-N-(pyridin-3-yl)benzamide
-
47% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B17
3-[(Z)-2,3-dihydro-1H-inden-1-ylidenemethyl]pyridine
-
50% inhibition at 0.087 mM
3-[(Z)-2-phenylvinyl]pyridine
-
CYP11B1 IC50: 288 nM, CYP11B2 IC50: 735 nM, no inhibition by the 3-[(E)-2-phenylvinyl]pyridine isomer, recombinant enzymes
3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-1-propanol
-
-
3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-1-propanol
-
-
3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-1-propanol
-
-
3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-1-propanol
-
-
3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-1-propanol
-
-
3-[2-[(1S)-1-(4-chlorophenyl)ethyl]-3,3-dioxido-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazin-4-yl]-2-methylpropan-1-ol
-
-
4-((5-phenyl-1H-imidazol-1-yl)methyl)benzonitrile
-
-
4-(2-methylpropyl)-2-(thiophen-2-ylmethyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
4-(2-methylpropyl)-2-[4-(trifluoromethoxy)benzyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
4-(2-methylpropyl)-2-[4-(trifluoromethyl)benzyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
-
-
4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
-
CYP11B1 IC50: 2529 nM, CYP11B2 IC50: 2834 nM, recombinant enzymes
4-(7-benzyl-6-oxo-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile
-
-
4-bromo-N-(pyridin-3-yl)benzamide
-
64% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B9
4-chloro-N-(pyridin-3-yl)benzamide
-
88% inhibition of CYP11B2 at 0.5 mM, 5% inhibition of CYP11B8
4-cyano-N-(pyridin-3-yl)benzamide
-
81% inhibition of CYP11B2 at 0.5 mM, 9% inhibition of CYP11B15
4-fluoro-N-(pyridin-3-yl)benzamide
-
86% inhibition of CYP11B2 at 0.5 mM, 7% inhibition of CYP11B7
4-methoxy-N-(pyridin-3-yl)benzamide
-
19% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B10
4-methyl-N-(pyridin-3-yl)benzamide
-
25% inhibition of CYP11B2 at 0.5 mM, no% inhibition of CYP11B13
4-nitro-N-(pyridin-3-yl)benzamide
-
64% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B16
4-[(Z)-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methyl]pyridine
-
50% inhibition at 0.034 mM, selective for CYP11B1
5-bromo-N-(pyridin-3-yl)pyridine-3-carboxamide
-
29% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B5
5-[(1E)-1-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)ethyl]isoquinoline
-
50% inhibition at 0.096 mM
5-[(E)-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methyl]isoquinoline
-
50% inhibition at 0.058 mM, selective for CYP11B1
5-[(E)-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methyl]pyrimidine
-
50% inhibition at 0.027 mM, very selective for CYP11B1
5-[(Z)-(5-fluoro-2,3-dihydro-1H-inden-1-ylidene)methyl]isoquinoline
-
50% inhibition at 0.026 mM, selective for CYP11B1
5-[(Z)-2,3-dihydro-1H-inden-1-ylidenemethyl]-1H-imidazole
-
50% inhibition at 0.0061 mM
5-[(Z)-3,4-dihydronaphthalen-1(2H)-ylidenemethyl]-1H-imidazole
-
50% inhibition at 0.0033 mM
6,6-dimethyl-8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
6-(5,8-dihydroisoquinolin-4-yl)-3,4-dihydroquinolin-2(1H)-one
-
94% inhibition of CYP11B2 at 0.5 mM, 91% inhibition of CYP11B1
6-methoxydihydronaphthalene
-
-
8-(1H-imidazol-1-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(2,3'-bipyridin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(5-ethoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(5-fluoropyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(5-hydroxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(5-methoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(5-phenylpyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one
-
-
8-(isoquinolin-4-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-thione
-
-
8-(pyrimidin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(2,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(2-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(2-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(3,4-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(3,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(3-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(3-hydroxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(3-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(4-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(4-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(propan-2-yloxy)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-(trifluoromethyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
8-[5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
-
-
9-(5-methoxypyridin-3-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
-
-
9-(pyridin-3-yl)-1,2,6,7-tetrahydro-5H-pyrido[ 3,2,1-ij]quinolin-3-one
-
-
9-[6-(isoquinolin-4-yl)pyridin-3-yl]-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
-
-
acetone
-
10%, v/v, complete inhibition of hydroxylation
Anti-11beta-hydroxylase IgG
antiserum
-
produced by rabbits
-
ascorbate
-
without NADH, inhibition of aldosterone synthetase
atenolol
-
potent inhibition of CYP11B2, recombinant enzyme
clotrimazole
-
azole derivative, antimycotic drug, strong dose-dependent inhibition
corticosterone
-
competitive inhibition of 11beta-hydroxylase activity
deoxycorticosterone
-
competitive substrate inhibition
diphosphatidyl glycerol
-
cardiolipin, dipalmitoyl phasphatidylcholine vesicles, 50% inhibition with 4-5 mol%, complete inhibition at 15 mol%
EDTA
-
10 mM
erythromycin
-
potent inhibition of CYP11B2, recombinant enzyme
ethanol
-
10%, v/v, complete inhibition of hydroxylation
FAD286
-
inhibitor of 11-beta-hydroxylase CYP11B1
fadrozole
HgCl2
-
0.2 mM, 50% inhibition
iron-sulfur protein
-
adrenodoxin, at high concentrations, 25% inhibition
-
KCl
-
total inactivation
KCN
-
slight inhibitor
ketoconazole
ketoprofene
-
potent inhibition of CYP11B2, recombinant enzyme
methanol
-
10%, v/v, complete inhibition of hydroxylation
methyl 3-(1-benzyl-1H-imidazol-5-yl)-propanoate
-
-
methyl 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-propanoate
-
-
methyl 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-propanoate
-
-
methyl 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-propanoate
-
-
methyl 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-propanoate
-
-
methyl 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-propanoate
-
-
methyltrienolone
-
synthetic androgen, used as photoaffinity ligand and substrate analog, covalent binding, 0.1 mM inhibits cortisol synthesis, during photolabeling radioactivity incorporation via radioactive methyltrienolone is blocked by 11-deoxycorticosterone, so it binds to the conserved substrate binding region Trp428-Leu429-Asp430-Arg431 between beta3-sheet and the L-helix analysed by trypsin digest
metyrapol
-
11beta-hydroxylase inhibition, 40.8% by racemate, 38.1% by (+)-enantiomer and 33.8% by (-)-enantiomer, each 0.4 mM
Metyrapone
miconazole
-
azole derivative, antimycotic drug, strong dose-dependent inhibition
N-(pyridin-3-yl)-4-(trifluoromethoxy)benzamide
-
-
N-(pyridin-3-yl)-4-(trifluoromethyl)benzamide
-
-
N-(pyridin-3-yl)benzamide
-
30% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B6
N-(pyridin-3-yl)biphenyl-4-carboxamide
-
-
N-(pyridin-3-yl)pyridine-3-carboxamide
-
8% inhibition of CYP11B2 at 0.5 mM, no inhibition of CYP11B3
N-(pyridin-3-yl)pyridine-4-carboxamide
-
39% inhibition of CYP11B2 at 0.5 mM, 4% inhibition of CYP11B4
norharman
-
beta-carboline, high affinity type II ligand to both cytochromes, progesterone binding to CYP17 competitively inhibited
p-chloromercuribenzoate
-
1 mM
PCMB
-
0.1 mM, 50% inhibition
phenazine methosulfate
-
1 mM, crude extract
phosphate
-
-
phosphatidylcholine
-
unsaturated increasing dioleoyl/diphytanoyl phosphatidylcholine
progesterone
-
progesterone acts as a competitive inhibitor for 11beta-hydroxylase and aldosterone synthase, inhibits aldosterone production by wild-type CYP11B1 and chimeric mutant CYP11B1/B2 in HEK-293 cells. The wild-type is more strongly inhibited than the chimera
R-fadrozole
-
-
S-fadrozole
-
-
SKF 525A
-
little inhibition of the purified 11beta-hydroxylase, 18-hydroxylation and aldosterone synthesis of corticosterone are inhibited
Sodium cholate
-
0.2% effect nearly 20% inhibition
spironolactone
-
diuretic and antihypertensive drug, competitive aldosterone antagonist, slight inhibition
Stilbestrol
-
-
sulfhydryl reagents
-
strongly
testosterone
-
potent inhibition of CYP11B2, recombinant enzyme
[3-(1H-imidazol-1-ylmethyl)phenyl]methanol
-
-
[4-(1H-imidazol-1-ylmethyl)phenyl]methanol
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-oxoglutarate
-
most potent activator in intact mitochondria
fumarate
-
increase of activity
KCN
-
slight
lipid extract
-
from adrenocortical mitochondria, increase of aldosterone production from corticosterone
-
malate
-
plus NADP+ and in synergism with ascorbate plus NADH increase of aldosterone synthetase activity in zona glomerulosa, no stimulation of 11beta-/18-hydroxylation
NAD(P)H
-
enhance activity of crude extracts that show hydroxylation without any cofactor
phosphatidylcholine
-
saturated acyl chains such as dipalmitoyl/dimyristoyl phosphatidylcholine
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0008 - 0.18
11-deoxycorticosterone
0.077 - 0.338
11-deoxycortisol
0.013
4-androstene-3,17-dione
-
identical for both enzyme activities
0.002 - 0.0024
adrenal ferredoxin
0.0059 - 0.09
corticosterone
0.006 - 0.02
deoxycorticosterone
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.133 - 1.83
11-deoxycorticosterone
0.167 - 3.45
11-deoxycortisol
1 - 1.48
adrenal ferredoxin
0.0378
corticosterone
Bos taurus
-
+/-0.2268, calculatetd from Kcat/Km
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000008 - 0.0000022
(R)-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile
0.0000013
6-methoxydihydronaphthalene
-
recombinant enzyme
additional information
additional information
-
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000024
(1R)-2-[2-[(1S)-1-(4-chlorophenyl)ethyl]-3,3-dioxido-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazin-4-yl]-1-phenylethanol
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000003
(1S)-2-[2-[(1S)-1-(4-chlorophenyl)ethyl]-3,3-dioxido-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazin-4-yl]-1-phenylethanol
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000016 - 0.0000099
(R)-4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile
0.000448
1-(1H-inden-2-yl)-1H-imidazole
Homo sapiens
-
CYP11B2 IC50: 448 nM, no inhibition of CYP11B1, recombinant enzymes
0.000334 - 0.000639
1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole
0.000143 - 0.000365
1-(3-bromobenzyl)-1H-imidazole
0.000151 - 0.000457
1-(3-chlorobenzyl)-1H-imidazole
0.001
1-(3-cyanobenzyl)-1H-imidazole
Homo sapiens
-
above, inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication; above, inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.000206 - 0.000815
1-(3-fluorobenzyl)-1H-imidazole
0.000236 - 0.001
1-(4-aminobenzyl)-1H-imidazole
0.000211 - 0.000479
1-(4-bromobenzyl)-1H-imidazole
0.0000051 - 0.000007
1-(4-bromobenzyl)-5-phenyl-1H-imidazole
0.001
1-(4-chlorobenzyl)-1H-imidazole
Homo sapiens
-
above, inhibition of CYP11B1, pH not specified in the publication, temperature not specified in the publication; above, inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000058 - 0.000025
1-(4-chlorobenzyl)-5-phenyl-1H-imidazole
0.000368 - 0.000372
1-(4-cyanobenzyl)-1H-imidazole
0.0000023 - 0.00002
1-(4-cyanobenzyl)-5-(2-fluorophenyl)-1H-imidazole
0.0000037 - 0.0000057
1-(4-cyanobenzyl)-5-(2-methylphenyl)-1H-imidazole
0.0000055 - 0.000032
1-(4-cyanobenzyl)-5-(3-fluorophenyl)-1H-imidazole
0.0000052 - 0.0000062
1-(4-cyanobenzyl)-5-(3-methylphenyl)-1H-imidazole
0.000025 - 0.000027
1-(4-cyanobenzyl)-5-(4-fluorophenyl)-1H-imidazole
0.000117 - 0.00013
1-(4-cyanobenzyl)-5-(4-methylphenyl)-1H-imidazole
0.000307 - 0.000407
1-(4-cyanobenzyl)-5-(4-pyridyl)-1H-imidazole
0.000007 - 0.000048
1-(4-cyanobenzyl)-5-(methyl carboxylate)-1H-imidazole
0.000044 - 0.000213
1-(4-cyanobenzyl)-5-(methylene-acetate)-1H-imidazole
0.000023 - 0.000073
1-(4-cyanobenzyl)-5-bromo-1H-imidazole
0.000062 - 0.000478
1-(4-cyanobenzyl)-5-formyl-1H-imidazole
0.000029 - 0.000285
1-(4-cyanobenzyl)-5-hydroxymethyl-1H-imidazole
0.000012 - 0.000141
1-(4-cyanobenzyl)-5-methyl-1H-imidazole
0.0000017 - 0.000028
1-(4-cyanobenzyl)-5-phenyl-1H-imidazole
0.00033 - 0.001799
1-(4-fluorobenzyl)-1H-imidazole
0.000011 - 0.000016
1-(4-fluorobenzyl)-5-phenyl-1H-imidazole
0.000014
1-(4-methoxybenzyl)-5-phenyl-1H-imidazole
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.000411 - 0.000763
1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole
0.0000048 - 0.000011
1-benzyl-5-phenyl-1H-imidazole
0.0000161 - 0.000166
2,4,5-trifluoro-N-(pyridin-3-yl)benzamide
0.0000052
2-(4-chlorobenzyl)-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000186
2-benzyl-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000094
2-[(1R)-1-(4-chlorophenyl)ethyl]-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000617
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-(2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000007
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-(3-methoxy-2-methylpropyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000013
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-(cyclopropylmethyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000078
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-[(3-methyloxetan-3-yl)methyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000008
2-[(1S)-1-(4-chlorophenyl)ethyl]-4-[(propan-2-yloxy)methyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000059 - 0.0000535
3,4-difluoro-N-(pyridin-3-yl)benzamide
0.000181 - 0.000286
3-(1-benzyl-1H-imidazol-5-yl)-1-propanol
0.00003 - 0.002117
3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine
0.000007 - 0.001268
3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine
0.00039 - 0.0006
3-(1H-imidazol-1-ylmethyl)aniline
0.000007 - 0.001729
3-(3,4-dihydronaphthalen-2-yl)pyridine
0.000005 - 0.000503
3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine
0.000176 - 0.001615
3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine
0.000013 - 0.001291
3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine
0.000004 - 0.005684
3-(6-methoxy-1H-inden-2-yl)pyridine
0.000002 - 0.000578
3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.000045
3-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
Homo sapiens
-
CYP11B2 IC50: 45 nM, no inhibition of CYP11B1, recombinant enzymes
0.000288 - 0.000735
3-[(Z)-2-phenylvinyl]pyridine
0.0000062 - 0.000018
3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000044 - 0.000055
3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000013 - 0.000048
3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000016 - 0.000116
3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-1-propanol
0.000012 - 0.000059
3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-1-propanol
0.0000114
3-[2-[(1S)-1-(4-chlorophenyl)ethyl]-3,3-dioxido-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazin-4-yl]-2-methylpropan-1-ol
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.0000005 - 0.0000017
4-((5-phenyl-1H-imidazol-1-yl)methyl)benzonitrile
0.000117
4-(2-methylpropyl)-2-(thiophen-2-ylmethyl)-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.000104
4-(2-methylpropyl)-2-[4-(trifluoromethoxy)benzyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.000121
4-(2-methylpropyl)-2-[4-(trifluoromethyl)benzyl]-1,2-dihydroimidazo[5,1-d][1,2,5]thiadiazine 3,3-dioxide
Homo sapiens
-
inhibition of CYP11B2, pH not specified in the publication, temperature not specified in the publication
0.002529 - 0.002834
4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.000104 - 0.000167
4-bromo-N-(pyridin-3-yl)benzamide
0.0000102 - 0.000065
4-chloro-N-(pyridin-3-yl)benzamide
0.0000075 - 0.000078
4-cyano-N-(pyridin-3-yl)benzamide
0.0000143 - 0.000082
4-fluoro-N-(pyridin-3-yl)benzamide
0.0000248 - 0.000145
4-nitro-N-(pyridin-3-yl)benzamide
0.0000002 - 0.000033
6-(5,8-dihydroisoquinolin-4-yl)-3,4-dihydroquinolin-2(1H)-one
0.000089 - 0.002077
8-(1H-imidazol-1-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000001 - 0.000158
8-(5-ethoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000044 - 0.001288
8-(5-fluoropyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000043 - 0.002045
8-(5-hydroxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000006 - 0.000247
8-(5-methoxypyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000013 - 0.000058
8-(5-phenylpyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one
0.0000002 - 0.000013
8-(isoquinolin-4-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000011 - 0.000715
8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000012 - 0.000333
8-(pyridin-3-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline-4-thione
0.000056 - 0.02855
8-(pyrimidin-5-yl)-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000036 - 0.000183
8-[5-(2,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000007 - 0.000043
8-[5-(2-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000024 - 0.000128
8-[5-(2-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000023 - 0.000496
8-[5-(3,4-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000018 - 0.001748
8-[5-(3,5-difluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000014 - 0.00049
8-[5-(3-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000012 - 0.000044
8-[5-(3-hydroxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000046 - 0.001374
8-[5-(3-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000009 - 0.00004
8-[5-(4-fluorophenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000014 - 0.000021
8-[5-(4-methoxyphenyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000022 - 0.000103
8-[5-(propan-2-yloxy)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000059 - 0.000141
8-[5-(trifluoromethyl)pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000016 - 0.002058
8-[5-[3-(trifluoromethoxy)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.000033 - 0.004646
8-[5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
0.0000009 - 0.000545
9-(5-methoxypyridin-3-yl)-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
0.0000024 - 0.002296
9-(pyridin-3-yl)-1,2,6,7-tetrahydro-5H-pyrido[ 3,2,1-ij]quinolin-3-one
0.0000002 - 0.000034
9-[6-(isoquinolin-4-yl)pyridin-3-yl]-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-5-one
0.000001 - 0.00001
fadrozole
0.000081 - 0.000224
ketoconazole
0.000193 - 0.000326
methyl 3-(1-benzyl-1H-imidazol-5-yl)-propanoate
0.000004 - 0.000057
methyl 3-[1-(4-bromobenzyl)-1H-imidazol-5-yl]-propanoate
0.000123 - 0.000177
methyl 3-[1-(4-chlorobenzyl)-1H-imidazol-5-yl]-propanoate
0.0000035 - 0.000031
methyl 3-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]-propanoate
0.00005 - 0.000104
methyl 3-[1-(4-fluorobenzyl)-1H-imidazol-5-yl]-propanoate
0.000111 - 0.000121
methyl 3-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]-propanoate
0.0000146 - 0.000072
Metyrapone
0.000006 - 0.000119
R-fadrozole
0.00004 - 0.000171
S-fadrozole
0.000206 - 0.001174
[3-(1H-imidazol-1-ylmethyl)phenyl]methanol
0.000695 - 0.001
[4-(1H-imidazol-1-ylmethyl)phenyl]methanol
0.0001
additional information
Homo sapiens
-
development and analysis of inhibitory potency of diverse inhibitors by superimposition of active and non-active compounds, modelling based on two pyridyl substituted acenaphthene derivatives, IC50 values of good inhibitors below 100 nM and of weak inhibi
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000314
-
aldosterone production, mitochondria from zona glomerulosa
0.0000236
-
18-hydroxycorticosterone production, mitochondria from zona fasciculata
0.00003
-
18-hydroxylation
0.000119
-
18-hydroxycorticosterone production, mitochondria from zona glomerulosa
0.000171
-
18-hydroxylation activity, 4% O2, 96% N2
0.000211
-
18-hydroxylation activity, 21% O2, 79% N2
0.001061
-
deoxycorticosterone, 18-hydroxylation activity in
0.00205
-
11beta-hydroxylation activity, 4% O2, 96% N2
0.00206
-
18-hydroxydeoxycorticosterone production, mitochondria from zona glomerulosa
0.00278
-
11beta-hydroxylation activity, 21% O2, 79% N2
0.0053
-
11beta-hydroxylation
0.00599
-
18-hydroxydeoxycorticosterone production, mitochondria from zona fasciculata
0.00691
-
corticosterone production, mitochondria from zona glomerulosa
0.00951
-
corticosterone production, mitochondria from zona fasciculata
0.00968
-
+/-0.00126, 40.8% inhibition by 0.4 mM metyrapol, adrenal tissue
0.00986
-
+/-0.00044, 39.7% inhibition by 0.4 mM metyrapone, adrenal tissue
0.01011
-
+/-0.00126, 38.1% inhibition by 0.4 mM (+)-metyrapol, adrenal tissue
0.01081
-
+/-0.00269, 33.8% inhibition by 0.4 mM (-)-metyrapol, adrenal tissue
0.01193
-
deoxycorticosterone, 11beta-hydroxylation activity
0.01633
-
+/-0.00237, no inhibitor, adrenal tissue
0.0198
-
purified recombinant enzyme
1.35 - 1.36
-
corticosterone, enzyme incorporated into liposomes
1.38
-
corticosterone, soluble form of enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2
-
assay at; assay at
7.5
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 7.2
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26
-
assay at
35
-
30 mM sodium phosphate buffer
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2 - 50
-
at 50°C almost no activity
2 - 15
-
2fold decrease of activity with increase of temperature, temperatures above 25°C unfavourable
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
isolated mitochondria from human NCI-H295 adrenal cells
Manually annotated by BRENDA team
-
cerebellar granule layer
Manually annotated by BRENDA team
-
corresponding to mammalian adrenal gland, P-450(11beta,aldo) and adrenodoxin reductase exist more in outer regions of frogs during the spring and the summer
Manually annotated by BRENDA team
higher enzyme expression level
Manually annotated by BRENDA team
slightly expressed
Manually annotated by BRENDA team
-
pharmacokinetics of metyrapone and metyrapol
Manually annotated by BRENDA team
-
adrenocortical tumor cell line Y-1
Manually annotated by BRENDA team
CYP11B1 expression
Manually annotated by BRENDA team
CYP11B1 expression
Manually annotated by BRENDA team
additional information