Information on EC 1.14.14.19 - steroid 17alpha-monooxygenase and Organism(s) Homo sapiens

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The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.19
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RECOMMENDED NAME
GeneOntology No.
steroid 17alpha-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2 = a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
the hydroxylation reaction is believed to proceed through a conventional Compound I rebound mechanism. Thr306 is a member of the conserved acid/alcohol pair essential for the efficient delivery of protons required for hydroperoxoanion heterolysis and formation of Compound I in the cytochromes P450. Involvement of a nucleophilic peroxo-anion rather than the traditional Compound I in catalysis. The peroxoanion is required to initiate O-O bond scission and formation of the Cpd I reactive intermediate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C-C bond cleavage
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C17-C20 bond cleavage
deacylation
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hydroxylation
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oxidation
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-
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen biosynthesis
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glucocorticoid biosynthesis
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androgen and estrogen metabolism
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Steroid hormone biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
steroid,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating)
Requires NADPH and EC 1.6.2.4, NADPH---hemoprotein reductase. A microsomal hemeprotein that catalyses two independent reactions at the same active site - the 17alpha-hydroxylation of pregnenolone and progesterone, which is part of glucocorticoid hormones biosynthesis, and the conversion of the 17alpha-hydroxylated products via a 17,20-lyase reaction to form androstenedione and dehydroepiandrosterone, leading to sex hormone biosynthesis (EC 1.14.14.32, 17alpha-hydroxyprogesterone deacetylase). The ratio of the 17alpha-hydroxylase and 17,20-lyase activities is an important factor in determining the directions of steroid hormone biosynthesis towards biosynthesis of glucocorticoid or sex hormones.
CAS REGISTRY NUMBER
COMMENTARY hide
9029-67-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
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
16,17-dehydropregnenolone + [reduced NADPH-hemoprotein reductase]+ O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
16,17-dehydroprogesterone + [reduced NADPH-hemoprotein reductase]+ O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + AH2 + O2
?
show the reaction diagram
-
-
-
-
?
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH + O2
5alpha-pregnan-17alpha-ol-3,20-dione + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NADPH + O2
5alpha-pregnan-3alpha,17alpha-diol-20-one + ?
show the reaction diagram
-
-
-
-
?
7-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
7-dehydro-17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
pregnenolone + ferrocytochrome b5 + O2
?
show the reaction diagram
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-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
show the reaction diagram
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reaction via 17alpha-hydroxyprogesterone
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-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
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-
-
-
?
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
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-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
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?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
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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
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
show the reaction diagram
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-
-
-
?
7-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
7-dehydro-17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
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-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
pregnenolone + ferrocytochrome b5 + O2
?
show the reaction diagram
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?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
show the reaction diagram
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reaction via 17alpha-hydroxyprogesterone
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?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
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?
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
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?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
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?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
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cytochrome P450
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ferrocytochrome b5
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
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(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
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(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
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(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
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(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
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(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
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(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
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(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
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(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
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(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
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(2Z)-3-[3-hydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
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41.34% inhibition at 0.01 mM
(2Z)-3-[4-methoxy-3-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
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43.27% inhibition at 0.01 mM
(2Z)-3-[4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
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45.5% inhibition at 0.01 mM
(4-(benzo[b]thiophen-5-yl)phenyl)methanol
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2% inhibition at 200 nM and 39% inhibition at 0.002 mM
(S)-(-)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate
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at 1.8 nM 50% C17,20-lyase inhibition, at 3.3 nM 50% 17alpha-hydroxylase inhibition
(S)-orteronel
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three times more inhibitory toward the conversion of 17alpha-hydroxypregnenolone to dehydroepiandrosterone than toward the 17alpha-hydroxylation of pregnenolone. The (S)-enantiomer of orteronel is more inhibitory than the (R) enantiomer
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1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
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1-((4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-methyl)-1H-imidazole
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19% inhibition at 200 nM and 74% inhibition at 0.002 mM
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
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1-((9H-fluoren-2-yl)methyl)-1H-imidazole
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1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
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1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
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1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
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1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
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1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
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1-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
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21% inhibition at 200 nM and 75% inhibition at 0.002 mM
1-(1-(4-(naphthalen-2-yl)phenyl)propyl)-1H-imidazole
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1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
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1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
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1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
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1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
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1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
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1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
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1-(1-biphenyl-4-yl-butyl)-1H-imidazole
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1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
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1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
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1-(1-biphenyl-4-yl-propyl)-1H-imidazole
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1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
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1-(1-[4-[5-(methylsulfanyl)thiophen-2-yl]phenyl]propyl)-1H-imidazole
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1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
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1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
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1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
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1-(1H-imidazol-5-yl)-2-methyl-1-(4-thiophen-3-ylphenyl)propan-1-ol
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1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
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1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
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1-(3-(4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)phenyl)pentan-3-yl)-1H-imidazole
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1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
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1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
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1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
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1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
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1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
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1-(4-(6-methoxynaphthalen-2-yl)phenyl)propan-1-ol
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7% inhibition at 200 nM and 43% inhibition at 0.002 mM
1-(4-(benzofuran-5-yl)benzyl)-1H-imidazole
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no inhibition at 200 nM and 21% inhibition at 0.002 mM
1-(4-chlorobenzyl)-1H-imidazole
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1-(4-fluorobenzyl)-1H-imidazole
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1-(4-furan-3-ylbenzyl)-1H-imidazole
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1-(4-methylbenzyl)-1H-imidazole
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1-(4-nitrobenzyl)-1H-imidazole
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1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
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1-(imidazol-1-ylmethyl)-4-bromo-9H-9-xanthenone
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at 0.0025 mM 98% inhibition
1-(imidazol-1-ylmethyl)-4-nitro-9H-9-xanthenone
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at 0.0025 mM 94% inhibition
1-(imidazol-1-ylmethyl)-9-oxo-9H-4-xanthenecarbonitrile
-
at 0.0025 mM 92% inhibition
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
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1-[(4-phenylthiophen-2-yl)methyl]-1H-imidazole
-
-
1-[(5,7-dibromobenzofuran-2-yl)methyl]imidazole
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at 185 nM 50% inhibition
1-[(5,7-dichlorobenzofuran-2-yl)methyl]imidazole
-
at 180 nM 50% inhibition
1-[(5-bromobenzofuran-2-yl)methyl]imidazole
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at 380 nM 50% inhibition
1-[(5-chlorobenzofuran-2-yl)methyl]imidazole
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at 230 nM 50% inhibition
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
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1-[1,1'-biphenyl]-4-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
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1-[1-(3',4'-dimethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
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1-[1-(3'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
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1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
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1-[1-(4'-ethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
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1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
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1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
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1-[1-(4'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
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1-[1-(4'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
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1-[1-(4-thiophen-3-ylphenyl)ethyl]-1H-imidazole
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1-[1-(4-thiophen-3-ylphenyl)propyl]-1H-imidazole
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1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
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1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
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1-[1-[2-fluoro-4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
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1-[1-[4-(2-chlorothiophen-3-yl)phenyl]propyl]-1H-imidazole
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1-[1-[4-(3,4-difluorophenyl)thiophen-2-yl]propyl]-1H-imidazole
-
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1-[1-[4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
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1-[4-(1H-imidazol-1-ylmethyl)phenyl]methanimine
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1-[4-(4-methylthiophen-3-yl)benzyl]-1H-imidazole
-
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1-[4-[5-(methylsulfanyl)thiophen-2-yl]benzyl]-1H-imidazole
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1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
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1-[[4-(3,4-difluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
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1-[[4-(3,4-dimethoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
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1-[[4-(3-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
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1-[[4-(4-fluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
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1-[[4-(4-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
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17-((1-(2-(trifluoromethyl)-1H-benzimidazol-5-yl)imino)ethyl)-5-androsten-3beta-ol
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78.61% inhibition at 0.01 mM
17-((1-(6-methoxybenzothiazol-2-yl)imino)ethyl)-5-androsten-3beta-ol
-
81.99% inhibition at 0.01 mM
17-(1-(n-hexylamino)-1-hydroxyethyl)-5-androsten-3beta-ol
-
62.52% inhibition at 0.01 mM
17-(1H-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
-
at 19 nM 50% inhibition, also potent inhibitor of 5alpha-reductase
17-(1H-1,2,4-triazol-1-yl)androsta-4,16-dien-3-one
-
at 55 nM 50% inhibition, also potent inhibitor of 5alpha-reductase
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
17-(3'-pyrazolyl)androsta-4,16-dien-3beta-one
-
type II competitive inhibitor
17-(3'-pyrazolyl)androsta-5,16-dien-3beta-ol
-
type II competitive inhibitor
17-(3-pyridyl)-5alpha-androst-16-en-3-one
-
at 3 nM 50% inhibition of C17,20-lyase and at 4.7 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-5alpha-androst-16-en-3alpha-ol
-
at 2.5 nM 50% inhibition of C17,20-lyase and at 4.3 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-androst-5-en-3beta-ol
-
at 23 nM 50% inhibition of C17,20-lyase and at 47 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-androsta-4,16-dien-3,11-dione
-
at 2.9 nM 50% inhibition of C17,20-lyase and at 13 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-3,5,16-triene
-
at 5.6 nM 50% inhibition of C17,20-lyase and at 12.5 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-4,16-dien-3-one
-
at 2.1 nM 50% inhibition of C17,20-lyase and at 2.8 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-5,6-dien-3beta-ol
17-(3-pyridyl)estra-1,3,5[10],16-tetraen-3-ol
-
at 1.8 nM 50% inhibition of C17,20-lyase and at 2.6 nM 50% inhibition of 17alpha-hydroxylase activity
17-(5'-isooxazoloyl)androsta-4,16-dien-3-one
-
type II competitive inhibitor
17-hydroxypregnenolone
-
competitive inhibitor of 17alpha-hydrolase activity
17alpha-Hydroxy-4-androsten-3-one
-
competitive inhibitor of 17alpha-hydroxylation of pregnenolone and of the subsequent C17,20-side chain cleavage reaction
17beta-(cyclopropylamino)-androst-5-en-3beta-ol
-
mechanism-based inhibitor, irreversible inhibition
17beta-acetamidoandrost-4-en-3-one
-
-
17beta-ureidoandrosta-1,4-dien-3-one
-
-
19-azido-androstenedione
-
-
19-thiomethyl-androstenedione
-
-
2'-[[(E)-3-oxoandrost-4-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
-
1 microM, 54% inhibition
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
-
1 microM, 78% inhibition
2'-[[(E)-6-oxo-3alpha,5alpha-cycloandrostan-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
-
compound strongly depresses electrocatalytic activity of CYP17A1 toward pregnenolone at concentrations of 0.1 microM and 1 microM, but data do not obey the Michaelis-Menten catalytic model
2-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzamide
-
39.38% inhibition at 0.01 mM
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
-
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
-
2-(4-pyridyl)propan-2-yl 1-adamantanecarboxylate
-
at 2.7 nM 50% C17,20-lyase inhibition, at 8.8 nM 50% 17alpha-hydroxylase inhibition
2-(chloromethyl)-5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
2-fluoro-4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)phenol hydrobromide
-
-
2-fluoro-4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)phenol hydrobromide
-
-
2-fluoro-4-[5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]phenol
-
-
2-fluoro-4-[5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl]phenol
-
-
2-fluoro-5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
20-hydroxyiminopregna-4,14,16-trien-3-one
-
at 0.0002 mM 50% inhibition
20-hydroxyiminopregna-4,16-dien-3-one
-
at 0.0001 mM 50% inhibition
20-hydroxyiminopregna-5,14,16-trien-3beta-ol
-
at 0.0002 mM 50% inhibition
20-hydroxyiminopregna-5,16-dien-3beta-ol
-
at 0.00017 mM 50% inhibition
21-hydroxyiminopregn-4-en-3-one
-
at 0.0003 mM 50% inhibition, also 5alpha-reductase inhibitor
21-hydroxyiminopregn-5-en-3beta-ol
-
at 0.00027 mM 50% inhibition
21-hydroxyiminopregna-4,17(20)-dien-3-one
-
at 0.00018 mM 50% inhibition, also 5alpha-reductase inhibitor
21-hydroxyiminopregna-5,17(29)-dien-3beta-ol
-
at 0.000077 mM 50% inhibition
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3,5,4'-triacetylresveratrol
-
-
3,5,4'-trimethylresveratrol
-
inhibition by is more selective on the 17,20-lyase activity than hydroxylase activity of CYP17A1
3,5-diacetylresveratrol
-
-
3,5-dihydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]benzoic acid
-
83.21% inhibition at 0.01 mM
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
-
3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
3-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
3-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
3-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
3beta-acetoxy-17-(3-pyridyl)androsta-5,16-diene
-
at 17 nM 50% inhibition of C17,20-lyase and at 18 nM 50% inhibition of 17alpha-hydroxylase activity
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
3beta-hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene
-
at 150 nM 60% inhibition
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
3beta-hydroxy-23,24-bisnor-5-cholenic-hydroxamic acid
-
at 0.0025 mM 20% inhibition
3beta-hydroxy-5-androsten-17beta-hydroxamic acid
-
at 0.0025 mM 17% inhibition
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
-
4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
-
-
4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
-
-
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-3-methoxybenzoic acid
-
43.34% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
-
56.23% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(isoxazol-3-yl)benzenesulfonamide
-
81.78% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
-
16.27% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonamide
-
57.1% inhibition at 0.01 mM; 78.84% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonic acid
-
8.37% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzoic acid
-
49.21% inhibition at 0.01 mM
4-(1H-imidazol-1-ylmethyl)-7-[(3-methylbenzyl)oxy]-2H-chromen-2-one
-
-
4-(1H-imidazol-1-ylmethyl)-7-[[3-(trifluoromethyl)benzyl]oxy]-2Hchromen-2-one
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-methylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl benzenesulfonate
-
-
4-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(4-methoxyphenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
4-(6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(8-(1-(1H-imidazol-1-yl)propyl)quinolin-5-yl)phenol
-
17% inhibition at 200 nM and 71% inhibition at 0.002 mM
4-(benzo[b]thiophen-5-yl)benzaldehyde
-
7% inhibition at 200 nM and 40% inhibition at 0.002 mM
4-hydroxybenzyl imidazole
-
-
4-pyridylmethyl 1-adamantanecarboxylate
-
at 18 nM 50% C17,20-lyase inhibition, at 43 nM 50% 17alpha-hydroxylase inhibition
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
-
4-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]morpholine
-
-
4-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
4-[5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]benzene-1,2-diol
-
-
4-[5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl]benzene-1,2-diol
-
-
4-[6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]pyridine
-
-
4-[6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-methoxyphenyl)-1H-inden-3-yl]pyridine
-
-
5-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-(1-(1H-imidazol-1-yl)propyl)phenyl)-1H-indole
-
5% inhibition at 200 nM and 27% inhibition at 0.002 mM
5-(4-(1H-imidazol-1-ylmethyl)phenyl)-1H-indole
-
5% inhibition at 200 nM and 39% inhibition at 0.002 mM
5-(4-fluorophenyl)-1-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-fluorophenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyrimidine
-
-
6-(3,4-difluorophenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3,4-difluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(4-(1H-imidazol-1-ylmethyl)phenyl)benzo[d]thiazole
-
no inhibition at 200 nM and 17% inhibition at 0.002 mM
6-(4-(3-(1H-imidazol-1-yl)pentan-3-yl)phenyl)naphthalen-2-ol
-
16% inhibition at 200 nM and 74% inhibition at 0.002 mM
6-(4-fluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
-
-
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
-
7-[(3-chlorobenzyl)oxy]-4-(1H-imidazol-1-ylmethyl)-2H-chromen-2-one
-
-
7-[(3-fluorobenzyl)oxy]-4-(1H-imidazol-1-ylmethyl)-2H-chromen-2-one
-
-
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
abiraterone
abiraterone acetate
-
-
CYP21
-
direct molecular interactions, with electrostatic interactions playing a crucial role, between steroidogenic enzymes CYP17 and CYP21, EC 1.14.99.10, that are localized in endoplasmic reticulum membranes of adrenal cortex and involved in biosynthesis of corticosteroid hormones. The interaction in vitro reduces the catalytic activities of both enzymes at high ionic strength, i.e. 300 mM NaCl, while it increases activity at low ionic strength, i.e. 100 mM NaCl, overview
-
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
-
E-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 7% inhibition
ketoconazole
methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
-
-
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
-
N-(4,6-dimethylpyrimidin-2-yl)-4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzene sulfonamide
-
48.37% inhibition at 0.01 mM
N-(4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)phenyl)acetamide
-
40.02% inhibition at 0.01 mM
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
-
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
-
N-[4'-[1-hydroxy(1H-imidazol-4-yl)methyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]-N'-methylurea
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-4-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)ethyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[cyclopropyl(hydroxy)-1H-imidazol-4-ylmethyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
-
-
pregnenolone
-
-
progesterone
-
-
resveratrol
-
i.e. trans-3,5,4'-trihydroxystilbene
siRNA
-
siRNA targeting the CYP17 gene
-
sulfamerazine
-
53.44% inhibition at 0.01 mM
sulfamethazine
-
49.34% inhibition at 0.01 mM
sulfamethoxazole
-
55.23% inhibition at 0.01 mM
TOK-001
VN/124-1
-
a 17alpha-hydroxylase/17,20 lyase inhibitor, is cytotoxic in prostate cancer cells and synergistically induces endoplasmic reticulum stress, mechanism, overview
VN/85-1
-
-
Z-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 5% inhibition
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
-
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CYP21
-
direct molecular interactions, with electrostatic interactions playing a crucial role, between steroidogenic enzymes CYP17 and CYP21, EC 1.14.99.10, that are localized in endoplasmic reticulum membranes of adrenal cortex and involved in biosynthesis of corticosteroid hormones. The interaction in vitro reduces the catalytic activities of both enzymes at high ionic strength, i.e. 300 mM NaCl, while it increases activity at low ionic strength, i.e. 100 mM NaCl, overview
-
cytochrome b5
-
additional information
-
not activating: antiepileptic drugs valproic acid, carbamazepine, topiramate, lamotrigine
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0004 - 0.0008
17-hydroxypregnenolone
0.0017
17alpha-hydroxypregnenolone
-
-
0.018
5alpha-pregnan-3alpha-ol-20-one
-
pH 7.4
0.00025 - 0.0077
pregnenolone
0.00045 - 0.0105
progesterone
additional information
additional information
-
calculation of intramolecular and intermolecular kinetic isotope effects for wild-type and mutant enzymes, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00283
17alpha-hydroxypregnenolone
-
-
0.0037 - 0.11
pregnenolone
0.0064 - 0.17
progesterone
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7.4 - 100
pregnenolone
4.7 - 40
progesterone
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.005
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
more than 0.005000
0.000112
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
-
0.000388
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
-
0.0031
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.003100
0.005
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.005000
0.002
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.002000
0.005
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
more than 0.005000
0.005
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.005000
0.0014
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
-
0.00046
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
-
0.00031
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
-
0.00078
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
-
0.00079
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
-
0.0021
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
-
0.00058
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
-
0.00105
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
-
0.0003
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
-
0.00045
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
-
0.0023
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
0.0038
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
-
0.0013
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
-
0.000756
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
0.000345
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
-
0.000168
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
-
0.00008
17-(1H-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
-
noncompetitive inhibitor
0.000041
17-(1H-1,2,4-triazol-1-yl)androsta-4,16-dien-3-one
-
noncompetitive inhibitor
0.0000019
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
-
noncompetitive inhibitor
0.0003 - 0.0008
17-hydroxypregnenolone
0.00124 - 0.0096
17alpha-hydroxyandrosten-3-one
0.000118
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
-
0.000282
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
-
0.005
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
more than 0.005000
0.0000014
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
noncompetitive inhibitor
0.000023
3beta-hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene
-
noncompetitive inhibitor
0.0000012
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
-
noncompetitive inhibitor
0.005
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
more than 0.005000
0.000375
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
0.0022
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
-
0.000099
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
-
0.000072
abiraterone
-
-
0.005
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
more than 0.005000
0.00278
ketoconazole
-
-
0.005
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
more than 0.005000
0.0008
pregnenolone
-
competitive substrate with progesterone
0.0032
progesterone
-
competitive substrate with pregnenolone
0.0017
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
-
0.005
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
-
more than 0.005000
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00006
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00027
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00034
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00024
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000092
(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000015
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000026
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000022
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000026
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0222
(2Z)-3-[3-hydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
Homo sapiens;
-
at pH 7.4 and 37C
0.0247
(2Z)-3-[4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
Homo sapiens;
-
at pH 7.4 and 37C
0.005
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
Homo sapiens;
-
-
0.000112
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
Homo sapiens;
-
-
0.000388
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
Homo sapiens;
-
-
0.0031
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
Homo sapiens;
-
-
0.005
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
Homo sapiens;
-
-
0.002
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
Homo sapiens;
-
-
0.005
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
Homo sapiens;
-
-
0.005
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
Homo sapiens;
-
-
0.667
1-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
Homo sapiens;
-
-
0.0014
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
Homo sapiens;
-
-
0.00046
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
Homo sapiens;
-
-
0.00031
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
Homo sapiens;
-
-
0.00078
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
Homo sapiens;
-
-
0.00079
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
Homo sapiens;
-
-
0.0021
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
Homo sapiens;
-
-
0.00058
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
Homo sapiens;
-
-
0.00105
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
Homo sapiens;
-
-
0.0003
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
Homo sapiens;
-
-
0.00045
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
Homo sapiens;
-
-
0.00013
1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000054
1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00015
1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0038
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
Homo sapiens;
-
-
0.0013
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
Homo sapiens;
-
-
0.000756
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
Homo sapiens;
-
-
0.000049
1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000028
1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000027
1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0023
1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
Homo sapiens;
-
-
0.0002
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000018
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000033
1-[1,1'-biphenyl]-4-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000188
1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
Homo sapiens;
-
-
0.000345
1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
Homo sapiens;
-
-
0.000168
1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
Homo sapiens;
-
-
0.000028
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00329
17-((1-(2-(trifluoromethyl)-1H-benzimidazol-5-yl)imino)ethyl)-5-androsten-3beta-ol
Homo sapiens;
-
at pH 7.4 and 37C
0.00238
17-((1-(6-methoxybenzothiazol-2-yl)imino)ethyl)-5-androsten-3beta-ol
Homo sapiens;
-
at pH 7.4 and 37C
0.01859
17-(1-(n-hexylamino)-1-hydroxyethyl)-5-androsten-3beta-ol
Homo sapiens;
-
at pH 7.4 and 37C
0.000118
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
Homo sapiens;
-
-
0.000282
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
Homo sapiens;
-
-
0.000064
2-fluoro-4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)phenol hydrobromide
Homo sapiens;
-
-
0.000188
2-fluoro-4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)phenol hydrobromide
Homo sapiens;
-
-
0.000052
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
Homo sapiens;
-
-
0.00009
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
Homo sapiens;
-
-
0.00129
3,5-dihydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]benzoic acid
Homo sapiens;
-
at pH 7.4 and 37C
0.005
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
Homo sapiens;
-
-
0.02
3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
Homo sapiens;
-
above
0.00235
3-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
Homo sapiens;
-
-
0.000217
3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
Homo sapiens;
-
-
0.005
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
Homo sapiens;
-
-
0.000379
4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
Homo sapiens;
-
-
0.000261
4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
Homo sapiens;
-
-
0.000152
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
Homo sapiens;
-
-
0.000195
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
Homo sapiens;
-
-
0.000164
4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
Homo sapiens;
-
-
0.000231
4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
Homo sapiens;
-
-
0.000375
4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
Homo sapiens;
-
-
0.000044
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00016
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00211
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(isoxazol-3-yl)benzenesulfonamide
Homo sapiens;
-
at pH 7.4 and 37C
0.00311 - 0.0198
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonamide
0.000233
4-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
Homo sapiens;
-
-
0.02
4-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
Homo sapiens;
-
above
0.005
4-(5-(4-methoxyphenyl)-3H-inden-1-yl)pyridine hydrochloride
Homo sapiens;
-
above
0.000144
4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
Homo sapiens;
-
-
0.000307
4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
Homo sapiens;
-
-
0.00122
4-(6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
Homo sapiens;
-
-
0.005
4-(6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
Homo sapiens;
-
above
0.000163
4-(6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
Homo sapiens;
-
-
0.005
4-(6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
Homo sapiens;
-
above
0.0022
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
Homo sapiens;
-
-
0.01
5-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
Homo sapiens;
-
above
0.02
5-(4-fluorophenyl)-1-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-ol
Homo sapiens;
-
above
0.000333
5-(4-fluorophenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
Homo sapiens;
-
-
0.02
5-(4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
Homo sapiens;
-
above
0.000423
6-(3,4-difluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
Homo sapiens;
-
-
0.005
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
Homo sapiens;
-
above
0.000587
6-(4-fluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
Homo sapiens;
-
-
0.000036
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00003
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00016
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000039
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000075
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000016
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000038
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000099
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
Homo sapiens;
-
-
0.000018
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000022
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000072
abiraterone
0.005
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
Homo sapiens;
-
-
0.00278 - 0.00378
ketoconazole
0.000024
methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000036
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0268
N-(4,6-dimethylpyrimidin-2-yl)-4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzene sulfonamide
Homo sapiens;
-
at pH 7.4 and 37C
0.000046
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.005
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
Homo sapiens;
-
-
0.000077
N-[4'-[1-hydroxy(1H-imidazol-4-yl)methyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000021
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]-N'-methylurea
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000024
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00012
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-4-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000038
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)ethyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00004
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000045
N-[4'-[cyclopropyl(hydroxy)-1H-imidazol-4-ylmethyl][1,1'-biphenyl]-3-yl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000036
N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000039
N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
Homo sapiens;
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0342
sulfamerazine
Homo sapiens;
-
at pH 7.4 and 37C
0.0017
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
Homo sapiens;
-
-
0.005
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
Homo sapiens;
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
17alpha-hydroxylase and 17,20-lyase activity of recombinant wild-type and mutant enzymes
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.9 - 8.5
-
for 17alpha-hydroxylation of pregnenolone
8.5
-
for 17alpha-hydroxylation of progesterone
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
androgen-secreting, from females with polycystic ovary syndrome undergoing hysterectomy or ovarian wedge resection; polycystic ovary syndrome, PCOS, theca cell
Manually annotated by BRENDA team
-
a adrenal cortex tissue layer that excretes androgens
Manually annotated by BRENDA team
additional information
-
immunohistochemic determination of the enzyme in fetal neural tissues and during development, detailed overview
Manually annotated by BRENDA team
PDB
SCOP
CATH
UNIPROT
ORGANISM
Homo sapiens;
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57000
-
-
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
Ser/Thr phosphorylation of P450c17 appears to promote P450 oxidoreductase-P450c17 interaction. The kinase that phosphorylates P450c17 is p38alpha, the p38beta isozyme is inactive
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular docking of inhibitors to the active site
-
mutant enzyme A105L in complex with progesterone, pregnenolone, 17alpha-hydroxypregnenolone, or abiraterone is crystallized by the hanging drop vapor diffusion method using 100 mM Tris-HCl, pH 8.5, 25% (w/v) PEG 4000, 150 mM magnesium chloride hexahydrate, and 4-6% (v/v) glycerol. Mutant enzyme A105L in complex with 17alpha-hydroxyprogesterone is crystallized by the hanging drop vapor diffusion method using 175 mM Tris-HCl, pH 8.5, 30% (w/v) PEG 3350, 250 mM lithium sulfate, and 3% (v/v) glycerol
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 0.25 M sucrose, pH 7.4, 2 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
metal affinity and ion exchange chromatography
-
nickel-nitrilotriacetic acid affinity resin column chromatography, His Select resin column chromatography, and Sartorius Vivapure-S spin column chromatography
-
nickel-nitrilotriacetic acid-agarose resin column chromatography, carboxymethyl-Sepharose column chromatography, and Superdex 200 gel filtration
-
recombinant enzyme partially from Pichia pastoris strain GS115 by microsome preparation
-
recombinant His-tagged enzyme from Escherichia coli strain JM109 by nickel affinity chromatography
-
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli strain JM109 by anion exchange and nickel affinity chromatography, hydroxyapatite chromatography, and gel filtration
-
recombinant membrane-embedded His-tagged wild-type and mutant enzymes from Escherichia coli strain JM109 by nickel affinity chromatography
recombinant wild-type and mutant enzymes from yeast mcirosomes, recombinant modified CYP17A1 from Escherichia coli strain JM109 to homogeneity
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
co-expression of CYP17 and NADPH-P450 reductase in Escherichia coli, expression of the enzyme in insect cells via baculovirus transfection
-
CYP17, expression in Escherichia coli, co-expression with NADPH-P450 reductase
-
CYP17A1, DNA and amino acid sequence determination and analysis, expression of mutant R239Q in HEK-293 cells
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DNA and amino acid sequence determination and analysis of wild-type and mutant enzymes, genotyping
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expressed in Escherichia coli
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expressed in Escherichia coli JM109 cells
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expression in Escherichia coli cells; gene CYp17, expression in Escherichia coli, coexpression with human cytochrome P450 reductase
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expression in Escherichia coli JM109, human gene with an (His)4-tail
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expression in Escherichia coli XL1
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expression in Escherichia coli, human gene with an (His)4-tail
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expression in HEK-293T cell
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expression in monkey kidney COS-1 cells
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expression in Saccharomyces cerevisiae strain W303B of the K89N-mutant
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expression of His-tagged enzyme in Escherichia coli strain JM109, coexpression with molecular chaperones GroES and GroEL
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expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain JM109
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expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain JM109, co-expression of P450c17 and p38 in COS-1 cells
expression of wild-type and mutant C-terminally Bis-tagged enzymes lacking the N-terminal transmembrane helix in Escherichia coli strain JM109
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expression of wild-type and mutant enzymes in yeast microsomes, expression of modified CYP17A1 in Escherichia coli strain JM109
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functional expression of cytochrome P45017alpha in Pichia pastoris strain GS115, subcloning in Escherichia coli strain JM109
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gene CYP17, coexpression in Escherichia coli with human NADPH-P450 reductase
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gene CYP17, expression in HeLa cells
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gene CYP17A1, DNA and amino acid sequence determination and analysis of wild-type and mutant enzymes, overview
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gene CYP17A1, genotyping
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recombinant expression in Escherichia coli
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recombinant expression in yeast microsomes
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
RNAi effectively reduces the expression of exogenous CYP17 in HeLa cells by up to 50%. The CYP17 mRNA and androstenedione production of theca cells are slightly, but not significantly, reduced when compared with non-specific siRNA
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the enzyme is induced by forskolin
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the expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries. At least three factors, NF1, SF1 and SF3, control the expression level of human CYP17A1 in adrenals. Regions of the CYP17A1 gene responsible for binding transcriptional factors are: nt -107 to -85 and nt -178 to -152 for NF1-1C, nt -227 to -184 for SF1 and SF3
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A174E/K388X
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naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
D216H
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natural genetic variant. Cells transiently expressing D216H demonstrate a selective impairment of 16alpha-hydroxyprogesterone synthesis by 2.1fold compared to wild-type CYP17A1, no effect on 17alpha-hydroxyprogesterone synthesis is observed
E305G
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naturally occuring mutation, the active site mutant shows lack of 17,20-lyase activity and reduced 17alpha-hydroxylase activity compared to the wild-type, males homozygous show a phenotype with severe micropenis, perineal hypospadias, chordae, and bifid scrotum, while females show normal genitalia, genotyping of two families, overview
G162R
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natural genetic variant. Mutation leads to decreased CYP17A1 protein stability with a near 70% reduction in protein levels compared to wild-type. Mutant is preferentially ubiquitinated and degraded prematurely, with an enzyme half-life of about 2.5 h, proteasome inhibitor treatment recovers G162R protein expression
H373L
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the replacement causes complete loss of both 17alpha-hydroxylase and 17,20-lyase activities with a defect in heme binding due to a global alteration of P450c17 structure. The mutation is combined with another mutation, a deletion of codon 53 or 54 encoding Phe, TTC, in exon 1, DELTAF54, on a maternal allele. Both mutations together partially abolish both 17alpha-hydroxylase and 17,20-lyase activities. Enzyme deficiency causes clitoromegaly, phenotype, overview
H373N
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the substitution results in markedly reduced production of 17alpha-hydroxyprogesterone at 0.2% of the wild-type P450c17 and no production of androstenedione
K89N
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78% loss of 17,20-lyase activity and 20% loss of 17alpha-hydroxylase activity
L465P
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naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
R239Q
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naturally occuring mutation leading to loss of function of CYP17A1 and to enzyme deficiency resulting in failure in synthesizing cortisol, andrenal androgens, and gonadal steroids, phenotype, detailed overview
R347A
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site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R347K
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the mutant exhibits similar 17-hydroxylase and b5-stimulated 17,20-lyase activity as the wild type enzyme
R358A
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site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R358K
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the mutant exhibits similar 17-hydroxylase and b5-stimulated 17,20-lyase activity as the wild type enzyme
R449A
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site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R449L
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site-directed mutagenesis, the mutant shows no cytochrome b5-CYP17A1 complex formation
R96Q
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mutation identified in a female patient with a malignant mixed germ cell tumor. Mutation affects a key substrate-binding region and results in complete inactivity of enzyme
S258A
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significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
S258D
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significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
S427A
site-directed mutagenesis
S427D
site-directed mutagenesis
S427E
site-directed mutagenesis
T260D
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significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
T306A
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site-directed mutagenesis, the mutant shows highly reduced hydroxylation activity compared to the wild-type enzyme. due to a high degree of uncoupling in which reducing equivalents and protons are funneled into non-productive pathways. The catalysis of carbon-carbon bond scission by the T306A mutant is largely unimpeded by disruption of the CYP17A1 acid-alcohol pair
T341A
site-directed mutagenesis
T341A/S427A
site-directed mutagenesis
T341D
site-directed mutagenesis
T341E
site-directed mutagenesis
V178D/R440C
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naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
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assay based on direct electrochemistry of CYP17A1 entrapped in didodecyldimethyl ammonium bromide-modified electrode under aerobic conditions in the supporting electrolyte solution
drug development
medicine