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Information on EC 1.14.14.19 - steroid 17alpha-monooxygenase and Organism(s) Homo sapiens and UniProt Accession P05093

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IUBMB Comments
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.
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Homo sapiens
UNIPROT: P05093
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The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
Synonyms
17,20-lyase, 17ohd, p450 17, cyp 17, p450(17alpha), cytochrome p450c17alpha, cytochrome p450 17alpha-hydroxylase, 17-hydroxylase/17,20-lyase, 17 alpha-hydroxylase/c17,20-lyase, 17alpha-ohase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
17-hydroxylase/17,20-lyase
-
17alphahydroxylase
-
17alpha-hydroxylase/17,20-lyase
-
cytochrome P450 17A1
-
cytochrome P450 17alpha-hydroxylase/17,20 lyase
-
cytochrome P450 17alpha-hydroxylase/17,20-lyase
-
cytochrome P450c17
-
P450 17A1
-
steroidogenic cytochrome P450 17A1
-
17,20-lyase
-
-
17-alpha-hydroxylase/C17-20 lyase
-
-
17-hydroxylase/17,20-lyase
-
-
17-hydroxylase/C17,20-lyase
-
-
17alpha-hydroxylase
-
-
17alpha-hydroxylase 17,20 lyase
-
-
17alpha-hydroxylase-17,20-lyase
-
-
17alpha-hydroxylase-C17,20 lyase
-
-
-
-
17alpha-hydroxylase-C17,20-lyase
-
-
17alpha-hydroxylase/17,20 lyase
-
-
17alpha-hydroxylase/17,20-lyase
-
-
17alpha-OHase
-
-
17OHD
-
-
CYP 17
-
-
CYPXVII
-
-
-
-
cytochrome P-450 (P45017alpha,lyase)
-
-
-
-
cytochrome P450 17
-
-
cytochrome P450 17alpha-hydroxylase
-
-
cytochrome P450 17alpha-hydroxylase-17,20-lyase
-
-
cytochrome P450 17alpha-hydroxylase/17,20-lyase
-
-
cytochrome P45017alpha
cytochrome P450c17alpha
-
-
P450-17alpha
-
-
P450-C17
-
-
-
-
P45017alpha
-
-
Steroid 17-alpha-hydroxylase/17,20 lyase
-
-
-
-
steroid 17alpha-hydroxylase
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
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
deacylation
-
-
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
hydroxylation
-
-
-
-
C-C bond cleavage
-
C17-C20 bond cleavage
PATHWAY SOURCE
PATHWAYS
-
-, -, -, -
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
-
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
-
-
-
?
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 + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
progesterone + [reduced NADPH-hemoprotein reductase] + O2
16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
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
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
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
pregnenolone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
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
-
reaction via 17alpha-hydroxyprogesterone
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
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
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
pregnenolone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
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
-
reaction via 17alpha-hydroxyprogesterone
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
-
-
-
cytochrome P450
-
-
-
ferrocytochrome b5
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(S)-orteronel
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
17-hydroxypregnenolone
competitive inhibitor of 17alpha-hydrolase activity
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
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
-
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
-
ketoconazole
-
resveratrol
i.e. trans-3,5,4'-trihydroxystilbene
(+)-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
-
-
(+)-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)propyl][1,1'-biphenyl]-3-yl]acetamide
-
-
(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
(-)-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
-
-
(-)-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)propyl][1,1'-biphenyl]-3-yl]acetamide
-
-
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
(2Z)-3-[3-hydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
-
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
-
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
-
45.5% inhibition at 0.01 mM
(4-(benzo[b]thiophen-5-yl)phenyl)methanol
-
2% inhibition at 200 nM and 39% inhibition at 0.002 mM
(S)-(-)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate
-
at 1.8 nM 50% C17,20-lyase inhibition, at 3.3 nM 50% 17alpha-hydroxylase inhibition
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
-
1-((4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-methyl)-1H-imidazole
-
19% inhibition at 200 nM and 74% inhibition at 0.002 mM
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
-
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
-
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
-
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
-
21% inhibition at 200 nM and 75% inhibition at 0.002 mM
1-(1-(4-(naphthalen-2-yl)phenyl)propyl)-1H-imidazole
-
-
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
-
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
1-(1-[4-[5-(methylsulfanyl)thiophen-2-yl]phenyl]propyl)-1H-imidazole
-
-
1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
-
-
1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
-
-
1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
-
-
1-(1H-imidazol-5-yl)-2-methyl-1-(4-thiophen-3-ylphenyl)propan-1-ol
-
-
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
-
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
-
1-(3-(4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)phenyl)pentan-3-yl)-1H-imidazole
-
-
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4-(6-methoxynaphthalen-2-yl)phenyl)propan-1-ol
-
7% inhibition at 200 nM and 43% inhibition at 0.002 mM
1-(4-(benzofuran-5-yl)benzyl)-1H-imidazole
-
no inhibition at 200 nM and 21% inhibition at 0.002 mM
1-(4-chlorobenzyl)-1H-imidazole
-
-
1-(4-fluorobenzyl)-1H-imidazole
-
-
1-(4-furan-3-ylbenzyl)-1H-imidazole
-
-
1-(4-methylbenzyl)-1H-imidazole
-
-
1-(4-nitrobenzyl)-1H-imidazole
-
-
1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
1-(imidazol-1-ylmethyl)-4-bromo-9H-9-xanthenone
-
at 0.0025 mM 98% inhibition
1-(imidazol-1-ylmethyl)-4-nitro-9H-9-xanthenone
-
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
-
-
1-[(4-phenylthiophen-2-yl)methyl]-1H-imidazole
-
-
1-[(5,7-dibromobenzofuran-2-yl)methyl]imidazole
-
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
-
at 380 nM 50% inhibition
1-[(5-chlorobenzofuran-2-yl)methyl]imidazole
-
at 230 nM 50% inhibition
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-[1,1'-biphenyl]-4-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-[1-(3',4'-dimethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(3'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
-
1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-ethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
-
1-[1-(4'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
-
1-[1-(4'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4-thiophen-3-ylphenyl)ethyl]-1H-imidazole
-
-
1-[1-(4-thiophen-3-ylphenyl)propyl]-1H-imidazole
-
-
1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
-
-
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
-
1-[1-[2-fluoro-4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[1-[4-(2-chlorothiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[1-[4-(3,4-difluorophenyl)thiophen-2-yl]propyl]-1H-imidazole
-
-
1-[1-[4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[4-(1H-imidazol-1-ylmethyl)phenyl]methanimine
-
-
1-[4-(4-methylthiophen-3-yl)benzyl]-1H-imidazole
-
-
1-[4-[5-(methylsulfanyl)thiophen-2-yl]benzyl]-1H-imidazole
-
-
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
-
1-[[4-(3,4-difluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(3,4-dimethoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(3-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(4-fluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(4-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
17-((1-(2-(trifluoromethyl)-1H-benzimidazol-5-yl)imino)ethyl)-5-androsten-3beta-ol
-
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
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-((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-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
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
-
-
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
-
-
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
-
also named galeterone
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
-
-
YM-116
-
-
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
-
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
0.00038 - 0.0011
pregnenolone
0.0011 - 0.0105
progesterone
0.00056
17-hydroxypregnenolone
-
-
0.0017
17alpha-hydroxypregnenolone
-
-
0.018
5alpha-pregnan-3alpha-ol-20-one
-
pH 7.4
0.00025 - 0.0077
pregnenolone
0.00045 - 0.0063
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
0.0037 - 0.11
pregnenolone
0.0064 - 0.17
progesterone
0.00283
17alpha-hydroxypregnenolone
-
-
0.0483
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
0.0003 - 0.0008
17-hydroxypregnenolone
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
0.00124 - 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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
0.00329
17-((1-(2-(trifluoromethyl)-1H-benzimidazol-5-yl)imino)ethyl)-5-androsten-3beta-ol
Homo sapiens
-
at pH 7.4 and 37°C
0.00238
17-((1-(6-methoxybenzothiazol-2-yl)imino)ethyl)-5-androsten-3beta-ol
Homo sapiens
-
at pH 7.4 and 37°C
0.01859
17-(1-(n-hexylamino)-1-hydroxyethyl)-5-androsten-3beta-ol
Homo sapiens
-
at pH 7.4 and 37°C
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 37°C
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 37°C
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 37°C
0.00211
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(isoxazol-3-yl)benzenesulfonamide
Homo sapiens
-
at pH 7.4 and 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
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 37°C
0.0342
sulfamerazine
Homo sapiens
-
at pH 7.4 and 37°C
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
7.2
assay at
6.9 - 8.5
-
for 17alpha-hydroxylation of pregnenolone
7.2
-
assay at
7.4
-
assay at
8.5
-
for 17alpha-hydroxylation of progesterone
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
-
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
malfunction
-
natural mutations causing CYP17A1 deficiency, i.e. 17OHD, a rare form of congenital adrenal hyperplasia
metabolism
physiological function
additional information
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
CP17A_HUMAN
508
0
57371
Swiss-Prot
Secretory Pathway (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57000
-
-
SUBUNIT
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
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A105L
D216H
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
G162R
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
K89N
78% loss of 17,20-lyase activity and 20% loss of 17alpha-hydroxylase activity
R347H
R347K
the mutant exhibits similar 17-hydroxylase and b5-stimulated 17,20-lyase activity as the wild type enzyme
R358K
the mutant exhibits similar 17-hydroxylase and b5-stimulated 17,20-lyase activity as the wild type enzyme
R358Q
R449L
site-directed mutagenesis, the mutant shows no cytochrome b5-CYP17A1 complex formation
S427A
site-directed mutagenesis
S427D
site-directed mutagenesis
S427E
site-directed mutagenesis
T306A
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
A174E/K388X
-
naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
E305G
-
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
H373L
-
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
-
the substitution results in markedly reduced production of 17alpha-hydroxyprogesterone at 0.2% of the wild-type P450c17 and no production of androstenedione
L465P
-
naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
R239Q
-
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
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R347H
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R358A
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R358Q
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R449A
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R96Q
-
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
-
significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
S258D
-
significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
T260D
-
significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
V178D/R440C
-
naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
additional information
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 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 His-tagged enzyme from Escherichia coli strain JM109 by nickel affinity chromatography
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
recombinant enzyme partially from Pichia pastoris strain GS115 by microsome preparation
-
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
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli JM109 cells
expression in HEK-293T cell
expression in Saccharomyces cerevisiae strain W303B of the K89N-mutant
expression of His-tagged enzyme in Escherichia coli strain JM109, coexpression with molecular chaperones GroES and GroEL
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
expression of wild-type and mutant enzymes in yeast microsomes, expression of modified CYP17A1 in Escherichia coli strain JM109
recombinant expression in yeast microsomes
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
-
DNA and amino acid sequence determination and analysis of wild-type and mutant enzymes, genotyping
-
expressed in Escherichia coli
-
expression in Escherichia coli cells
-
expression in Escherichia coli JM109, human gene with an (His)4-tail
-
expression in Escherichia coli XL1
-
expression in Escherichia coli, human gene with an (His)4-tail
-
expression in monkey kidney COS-1 cells
-
expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain JM109
-
functional expression of cytochrome P45017alpha in Pichia pastoris strain GS115, subcloning in Escherichia coli strain JM109
-
gene CYP17, coexpression in Escherichia coli with human NADPH-P450 reductase
-
gene CYp17, expression in Escherichia coli, coexpression with human cytochrome P450 reductase
-
gene CYP17, expression in HeLa cells
-
gene CYP17A1, DNA and amino acid sequence determination and analysis of wild-type and mutant enzymes, overview
-
gene CYP17A1, genotyping
-
recombinant expression in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is induced by forskolin
-
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
-
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
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
assay based on direct electrochemistry of CYP17A1 entrapped in didodecyldimethyl ammonium bromide-modified electrode under aerobic conditions in the supporting electrolyte solution
medicine
low apparent CYP17A1 activity, i.e. the combined 17alpha-hydroxylase/17,20-lyase activity, is associated with elevated daytime ambulatory blood pressure when salt intake is high. CYP17A1 activity is heritable and diminished in the elderly
drug development
medicine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hartmann, R.W.; Ehmer, P.B.; Haidar, S.; Hector, M.; Jose, J.; Klein, C.D.; Seidel, S.B.; Sergejew, T.F.; Wachall, B.G.; Wachter, G.A.; Zhuang, Y.
Inhibition of CYP 17, a new strategy for the treatment of prostata cancer
Arch. Pharm.
335
119-128
2002
Homo sapiens
Manually annotated by BRENDA team
Haidar, S.; Klein, C.D.; Hartmann, R.W.
Synthesis and evaluation of steroidal hydroxamic acids as inhibitors of P450 17 (1 alpha-hydroxylase/C17-20-lyase)
Arch. Pharm.
334
138-140
2001
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Recanatini, M.; Bisi, A.; Cavalli, A.; Belluti, F.; Gobbi, S.; Rampa, A.; Valenti, P.; Palzer, M.; Palusczak, A.; Hartmann, R.W.
A new class of nonsteroidal aromatase inhibitors: design and synthesis of chromone and xanthone derivatives and inhibition of the P450 enzymes aromatase and 17alpha-hydroxylase/C17,20-lyase
J. Med. Chem.
44
672-680
2001
Homo sapiens
Manually annotated by BRENDA team
Hartmann, R.W.; Hector, M.; Haidar, S.; Ehmer, P.B.; Reichert, W.; Jose, J.
Synthesis and evaluation of novel steroidal oxime inhibitors of P450 17 (17alpha-hydroxylase/C17-20-lyase) and 5alpha-reductase types 1 and 2
J. Med. Chem.
43
4266-4277
2000
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Njar, V.C.; Brodie, A.M.
Inhibitors of 17alpha-hydroxylase/17,20-lyase (CYP17): potential agents for the treatment of prostate cancer
Curr. Pharm. Des.
5
163-180
1999
Macacine alphaherpesvirus 1, Homo sapiens, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Auchus, R.J.; Miller, W.L.
Molecular modeling of human P450c17 (17alpha-hydroxylase/17,20-lyase): insights into reaction mechanisms and effects of mutations
Mol. Endocrinol.
13
1169-1182
1999
Homo sapiens (P05093), Homo sapiens
Manually annotated by BRENDA team
Brock, B.J.; Waterman, M.R.
The use of random chimeragenesis to study structure/function properties of rat and human P450c17
Arch. Biochem. Biophys.
373
401-408
2000
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Njar, V.C.; Kato, K.; Nnane, I.P.; Grigoryev, D.N.; Long, B.J.; Brodie, A.M.
Novel 17-azolyl steroids, potent inhibitors of human cytochrome 17alpha-hydroxylase-C17,20-lyase (P450(17)alpha): potential agents for the treatment of prostate cancer
J. Med. Chem.
41
902-912
1998
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Bahshwan, S.A.; Owen, C.P.; Nicholls, P.J.; Smith, H.J.; Ahmadi, M.
Some 1-[(benzofuran-2-yl)methyl]imidazoles as inhibitors of 17alpha-hydroxylase: 17,20-lyase (P450 17) and their specificity patterns
J. Pharm. Pharmacol.
50
1109-1116
1998
Bos taurus, Homo sapiens
Manually annotated by BRENDA team
Beaudoin, C.; Lavallee, B.; Tremblay, Y.; Hu, D.W.; Breton, R.; De Launoit, Y.; Belanger, A.
Modulation of 17alpha-hydroxylase/17,20-lyase activity of guinea pig cytochrome P450c17 by site-directed mutagenesis
DNA Cell Biol.
17
707-715
1998
Cavia porcellus, Homo sapiens
Manually annotated by BRENDA team
Zhuang, Y.; Zapp, J.; Hartmann, R.W.
Synthesis of Z- and E-1-methyl-2-(1-hydroximinoethyl)-6-methoxy-3,4-dihydronaphthalene and evaluation as inhibitors of 17alpha-hydroxylase-C17,20-lyase (P450 17)
Arch. Pharm.
330
359-361
1997
Homo sapiens
Manually annotated by BRENDA team
Chan, F.C.; Potter, G.A.; Barrie, S.E.; Haynes, B.P.; Rowlands, M.G.; Houghton, J.; Jarman, M.
3- and 4-pyridylalkyl adamantanecarboxylates: inhibitors of human cytochrome P450(17alpha) (17alpha-hydroxylase/C17,20-lyase). Potential nonsteroidal agents for the treatment of prostatic cancer
J. Med. Chem.
39
3319-3323
1996
Homo sapiens
Manually annotated by BRENDA team
Potter, G.A.; Barrie, S.E.; Jarman, M.; Rowlands, M.G.
Novel steroidal inhibitors of human cytochrome P45017alpha (17alpha-hydroxylase-C17,20-lyase): potential agents for the treatment of prostatic cancer
J. Med. Chem.
38
2463-2471
1995
Homo sapiens
Manually annotated by BRENDA team
Imai, T.; Globerman, H.; Gertner, J.M.; Kagawa, N.; Waterman, M.R.
Expression and purification of functional human 17alpha-hydroxylase/17,20-lyase (P450c17) in Escherichia coli. Use of this system for study of a novel form of combined 17alpha-hydroxylase/17,20-lyase deficiency
J. Biol. Chem.
268
19681-19689
1993
Homo sapiens
Manually annotated by BRENDA team
Bicikova, M.; Hampl, R.; Hill, M.; Starka, L.
Inhibition of steroid 17alpha-hydroxylase and C17,20-lyase in the human testis by epitestosterone
J. Steroid Biochem. Mol. Biol.
46
515-518
1993
Homo sapiens
Manually annotated by BRENDA team
Angelastro, M.R.; Laughlin, M.E.; Schatzman, G.L.; Bey, P.; Blohm, T.R.
17beta-(Cyclopropylamino)-androst-5-en-3 beta-ol, a selective mechanism-based inhibitor of cytochrome P450(17alpha) (steroid 17alpha-hydroxylase/C17-20 lyase)
Biochem. Biophys. Res. Commun.
162
1571-1577
1989
Homo sapiens
Manually annotated by BRENDA team
Schatzman, G.L.; Laughlin, M.E.; Blohm, T.R.
A normal phase high-performance liquid chromatography system for steroid 17alpha-hydroxylase/C17-20 lyase (cytochrome P-45021scc) assays
Anal. Biochem.
175
219-226
1988
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Fan, D.F.; Oshima, H.; Troen, B.R.; Troen, P.
Studies of the human testis. IV. Testicular 20alpha-hydroxysteroid dehydrogenase and steroid 17alpha-hydroxylase
Biochim. Biophys. Acta
360
88-99
1974
Homo sapiens
Manually annotated by BRENDA team
Gupta, M.K.; Guryev, O.L.; Auchus, R.J.
5alpha-reduced C21 steroids are substrates for human cytochrome P450c17
Arch. Biochem. Biophys.
418
151-160
2003
Homo sapiens
Manually annotated by BRENDA team
Naffin-Olivos, J.L.; Auchus, R.J.
Human cytochrome b5 requires residues E48 and E49 to stimulate the 17,20-lyase activity of cytochrome P450c17
Biochemistry
45
755-762
2006
Homo sapiens
Manually annotated by BRENDA team
Flueck, C.E.; Yaworsky, D.C.; Miller, W.L.
Effects of anticonvulsants on human p450c17 (17alpha-hydroxylase/17,20 lyase) and 3beta-hydroxysteroid dehydrogenase type 2
Epilepsia
46
444-448
2005
Homo sapiens
Manually annotated by BRENDA team
Souter, I.; Munir, I.; Mallick, P.; Weitsman, S.R.; Geller, D.H.; Magoffin, D.A.
Mutagenesis of putative serine-threonine phosphorylation sites proximal to Arg255 of human cytochrome P450c17 does not selectively promote its 17,20-lyase activity
Fertil. Steril.
85 Suppl 1
1290-1299
2006
Homo sapiens
Manually annotated by BRENDA team
Brooke, A.M.; Taylor, N.F.; Shepherd, J.H.; Gore, M.E.; Ahmad, T.; Lin, L.; Rumsby, G.; Papari-Zareei, M.; Auchus, R.J.; Achermann, J.C.; Monson, J.P.
A novel point mutation in P450c17 (CYP17) causing combined 17alpha-hydroxylase/17,20-lyase deficiency
J. Clin. Endocrinol. Metab.
91
2428-2431
2006
Homo sapiens
Manually annotated by BRENDA team
Lee, L.S.; Shu, W.J.; Wu, C.M.; Hsieh, C.H.; Chen, S.M.; Hu, C.J.; Chen, W.Y.; Chung, B.C.
A novel compound heterozygous mutation of K494_V495 deletion plus R496L and D487_F489 deletion in extreme C-terminus of cytochrome P450c17 causes 17alpha-hydroxylase deficiency
Mol. Cell. Endocrinol.
249
16-20
2006
Homo sapiens
Manually annotated by BRENDA team
Kolar, N.W.; Swart, A.C.; Mason, J.I.; Swart, P.
Functional expression and characterisation of human cytochrome P45017alpha in Pichia pastoris
J. Biotechnol.
129
635-644
2007
Homo sapiens
Manually annotated by BRENDA team
Pechurskaya, T.A.; Lukashevich, O.P.; Gilep, A.A.; Usanov, S.A.
Engineering, expression, and purification of "soluble" human cytochrome P45017alpha and its functional characterization
Biochemistry (Moscow)
73
806-811
2008
Homo sapiens
Manually annotated by BRENDA team
Tiosano, D.; Knopf, C.; Koren, I.; Levanon, N.; Hartmann, M.F.; Hochberg, Z.; Wudy, S.A.
Metabolic evidence for impaired 17alpha-hydroxylase activity in a kindred bearing the E305G mutation for isolate 17,20-lyase activity
Eur. J. Endocrinol.
158
385-392
2008
Homo sapiens
Manually annotated by BRENDA team
Beshay, V.E.; Havelock, J.C.; Sirianni, R.; Ye, P.; Suzuki, T.; Rainey, W.E.; Carr, B.R.
The mechanism for protein kinase C inhibition of androgen production and 17alpha-hydroxylase expression in a theca cell tumor model
J. Clin. Endocrinol. Metab.
92
4802-4809
2007
Homo sapiens
Manually annotated by BRENDA team
Pattison, J.C.; Saltzman, W.; Abbott, D.H.; Hogan, B.K.; Nguyen, A.D.; Husen, B.; Einspanier, A.; Conley, A.J.; Bird, I.M.
Gender and gonadal status differences in zona reticularis expression in marmoset monkey adrenals: Cytochrome b5 localization with respect to cytochrome P450 17,20-lyase activity
Mol. Cell. Endocrinol.
265-266
93-101
2007
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Hu, Q.; Negri, M.; Jahn-Hoffmann, K.; Zhuang, Y.; Olgen, S.; Bartels, M.; Mueller-Vieira, U.; Lauterbach, T.; Hartmann, R.W.
Synthesis, biological evaluation, and molecular modeling studies of methylene imidazole substituted biaryls as inhibitors of human 17alpha-hydroxylase-17,20-lyase (CYP17)--part II: Core rigidification and influence of substituents at the methylene bridge
Bioorg. Med. Chem.
16
7715-7727
2008
Homo sapiens
Manually annotated by BRENDA team
Du, J.; Liang, X.; Zeng, H.; Shu, Y.; Yao, S.; Zhu, B.; Zhuang, G.
Effect of small interfering RNAs of cytochrome P450 17alpha-hydroxylase/17,20-lyase (CYP17) on androgen biosynthesis in theca cells
Cell Biol. Int.
32
469-472
2008
Homo sapiens
Manually annotated by BRENDA team
Tian, Q.; Zhang, Y.; Lu, Z.
Partial 17alpha-hydroxylase/17,20-lyase deficiency-clinical report of five Chinese 46,XX cases
Gynecol. Endocrinol.
24
362-367
2008
Homo sapiens
Manually annotated by BRENDA team
Bruno, R.D.; Gover, T.D.; Burger, A.M.; Brodie, A.M.; Njar, V.C.
17alpha-Hydroxylase/17,20 lyase inhibitor VN/124-1 inhibits growth of androgen-independent prostate cancer cells via induction of the endoplasmic reticulum stress response
Mol. Cancer Ther.
7
2828-2836
2008
Homo sapiens
Manually annotated by BRENDA team
Shackleton, C.H.; Neres, M.S.; Hughes, B.A.; Stewart, P.M.; Kater, C.E.
17-Hydroxylase/C17,20-lyase (CYP17) is not the enzyme responsible for side-chain cleavage of cortisol and its metabolites
Steroids
73
652-656
2008
Homo sapiens
Manually annotated by BRENDA team
Pinto-Bazurco Mendieta, M.; Negri, M.; Hu, Q.; Hille, U.; Jagusch, C.; Jahn-Hoffmann, K.; Mueller-Vieira, U.; Schmidt, D.; Lauterbach, T.; Hartmann, R.
CYP17 inhibitors. Annulations of additional rings in methylene imidazole substituted biphenyls: Synthesis, biological evaluation and molecular modelling
Arch. Pharm.
341
547-609
2008
Homo sapiens
Manually annotated by BRENDA team
Ahmed, S.; Shahid, I.; Dhanani, S.; Owen, C.P.
Synthesis and biochemical evaluation of a range of sulfonated derivatives of 4-hydroxybenzyl imidazole as highly potent inhibitors of rat testicular 17alpha-hydroxylase/17,20-lyase (P-450(17alpha))
Bioorg. Med. Chem. Lett.
19
4698-4701
2009
Homo sapiens
Manually annotated by BRENDA team
Turan, S.; Bereket, A.; Guran, T.; Akcay, T.; Papari-Zareei, M.; Auchus, R.J.
Puberty in a case with novel 17-hydroxylase mutation and the putative role of estrogen in development of pubic hair
Eur. J. Endocrinol.
160
325-330
2009
Homo sapiens
Manually annotated by BRENDA team
Hille, U.E.; Hu, Q.; Vock, C.; Negri, M.; Bartels, M.; Mueller-Vieira, U.; Lauterbach, T.; Hartmann, R.W.
Novel CYP17 inhibitors: synthesis, biological evaluation, structure-activity relationships and modelling of methoxy- and hydroxy-substituted methyleneimidazolyl biphenyls
Eur. J. Med. Chem.
44
2765-2775
2009
Homo sapiens
Manually annotated by BRENDA team
Dhir, V.; Reisch, N.; Bleicken, C.M.; Lebl, J.; Kamrath, C.; Schwarz, H.P.; Groetzinger, J.; Sippell, W.G.; Riepe, F.G.; Arlt, W.; Krone, N.
Steroid 17alpha-hydroxylase deficiency: functional characterization of four mutations (A174E, V178D, R440C, L465P) in the CYP17A1 gene
J. Clin. Endocrinol. Metab.
94
3058-3064
2009
Homo sapiens
Manually annotated by BRENDA team
Pinto-Bazurco Mendieta, M.A.; Negri, M.; Jagusch, C.; Mueller-Vieira, U.; Lauterbach, T.; Hartmann, R.W.
Synthesis, biological evaluation, and molecular modeling of abiraterone analogues: novel CYP17 inhibitors for the treatment of prostate cancer
J. Med. Chem.
51
5009-5018
2008
Homo sapiens
Manually annotated by BRENDA team
Katsumata, N.; Ogawa, E.; Fujiwara, I.; Fujikura, K.
Novel CYP17A1 mutation in a Japanese patient with combined 17alpha-hydroxylase/17,20-lyase deficiency
Metab. Clin. Exp.
59
275-278
2009
Homo sapiens
Manually annotated by BRENDA team
Kaku, T.; Matsunaga, N.; Ojida, A.; Tanaka, T.; Hara, T.; Yamaoka, M.; Kusaka, M.; Tasaka, A.
17,20-lyase inhibitors. Part 4: design, synthesis and structure-activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors
Bioorg. Med. Chem.
19
1751-1770
2011
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Kaku, T.; Tsujimoto, S.; Matsunaga, N.; Tanaka, T.; Hara, T.; Yamaoka, M.; Kusaka, M.; Tasaka, A.
17,20-Lyase inhibitors. Part 3: Design, synthesis, and structure-activity relationships of biphenylylmethylimidazole derivatives as novel 17,20-lyase inhibitors
Bioorg. Med. Chem.
19
2428-2442
2011
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Stefanachi, A.; Favia, A.; Nicolotti, O.; Leonetti, F.; Pisani, L.; Catto, M.; Zimmer, C.; Hartmann, R.; Carotti, A.
Design, synthesis, and biological evaluation of imidazolyl derivatives of 4,7-disubstituted coumarins as aromatase inhibitors selective over 17-alpha-hydroxylase/C17-20 lyase
J. Med. Chem.
54
1613-1625
2011
Homo sapiens
Manually annotated by BRENDA team
Swart, A.C.; Storbeck, K.H.; Swart, P.
A single amino acid residue, Ala 105, confers 16alpha-hydroxylase activity to human cytochrome P450 17alpha-hydroxylase/17,20 lyase
J. Steroid Biochem. Mol. Biol.
119
112-120
2010
Capra hircus (A5HEW0), Capra hircus, Capra hircus South African angora (A5HEW0), Homo sapiens (P05093), Homo sapiens, Papio ursinus (Q9GLD2), Sus scrofa (P19100), Sus scrofa
Manually annotated by BRENDA team
Akhtar, M.; Wright, J.N.; Lee-Robichaud, P.
A review of mechanistic studies on aromatase (CYP19) and 17alpha-hydroxylase-17,20-lyase (CYP17)
J. Steroid Biochem. Mol. Biol.
125
2-12
2010
Homo sapiens
Manually annotated by BRENDA team
Chen, Y.; Saini, S.; Zaman, M.S.; Hirata, H.; Shahryari, V.; Deng, G.; Dahiya, R.
Cytochrome P450 17 (CYP17) is involved in endometrial cancinogenesis through apoptosis and invasion pathways
Mol. Carcinog.
50
16-23
2011
Homo sapiens
Manually annotated by BRENDA team
Khatri, Y.; Gregory, M.C.; Grinkova, Y.V.; Denisov, I.G.; Sligar, S.G.
Active site proton delivery and the lyase activity of human CYP17A1
Biochem. Biophys. Res. Commun.
443
179-184
2014
Homo sapiens (P05093)
Manually annotated by BRENDA team
Sushko, T.A.; Gilep, A.A.; Usanov, S.A.
Mechanism of intermolecular interactions of microsomal cytochrome P450s CYP17 and CYP21 involved in steroid hormone biosynthesis
Biochemistry (Moscow)
77
585-592
2012
Homo sapiens (P05093)
Manually annotated by BRENDA team
Yoshimoto, F.K.; Zhou, Y.; Peng, H.M.; Stidd, D.; Yoshimoto, J.A.; Sharma, K.K.; Matthew, S.; Auchus, R.J.
Minor activities and transition state properties of the human steroid hydroxylases cytochromes P450c17 and P450c21, from reactions observed with deuterium-labeled substrates
Biochemistry
51
7064-7077
2012
Homo sapiens (P05093)
Manually annotated by BRENDA team
Schonemann, M.D.; Muench, M.O.; Tee, M.K.; Miller, W.L.; Mellon, S.H.
Expression of P450c17 in the human fetal nervous system
Endocrinology
153
2494-2505
2012
Homo sapiens
Manually annotated by BRENDA team
Estrada, D.F.; Laurence, J.S.; Scott, E.E.
Substrate-modulated cytochrome P450 17A1 and cytochrome b5 interactions revealed by NMR
J. Biol. Chem.
288
17008-17018
2013
Homo sapiens (P05093)
Manually annotated by BRENDA team
Tee, M.K.; Miller, W.L.
Phosphorylation of human cytochrome P450c17 by p38alpha selectively increases 17,20 lyase activity and androgen biosynthesis
J. Biol. Chem.
288
23903-23913
2013
Homo sapiens (P05093)
Manually annotated by BRENDA team
Yoshimoto, F.K.; Desilets, M.C.; Auchus, R.J.
Synthesis of halogenated pregnanes, mechanistic probes of steroid hydroxylases CYP17A1 and CYP21A2
J. Steroid Biochem. Mol. Biol.
128
38-50
2012
Homo sapiens (P05093)
Manually annotated by BRENDA team
Cui, Y.L.; Xue, Q.; Zheng, Q.C.; Zhang, J.L.; Kong, C.P.; Fan, J.R.; Zhang, H.X.
Structural features and dynamic investigations of the membrane-bound cytochrome P450 17A1
Biochim. Biophys. Acta
1848
2013-2021
2015
Homo sapiens (P05093)
Manually annotated by BRENDA team
Estrada, D.F.; Skinner, A.L.; Laurence, J.S.; Scott, E.E.
Human cytochrome P450 17A1 conformational selection: modulation by ligand and cytochrome b5
J. Biol. Chem.
289
14310-14320
2014
Homo sapiens (P05093), Homo sapiens
Manually annotated by BRENDA team
Petrunak, E.M.; DeVore, N.M.; Porubsky, P.R.; Scott, E.E.
Structures of human steroidogenic cytochrome P450 17A1 with substrates
J. Biol. Chem.
289
32952-32964
2014
Homo sapiens (P05093), Homo sapiens
Manually annotated by BRENDA team
Peng, H.M.; Liu, J.; Forsberg, S.E.; Tran, H.T.; Anderson, S.M.; Auchus, R.J.
Catalytically relevant electrostatic interactions of cytochrome P450c17 (CYP17A1) and cytochrome b5
J. Biol. Chem.
289
33838-33849
2014
Homo sapiens (P05093)
Manually annotated by BRENDA team
Oskarsson, A.; Spatafora, C.; Tringali, C.; Andersson, A.O.
Inhibition of CYP17A1 activity by resveratrol, piceatannol, and synthetic resveratrol analogs
Prostate
74
839-851
2014
Homo sapiens (P05093)
Manually annotated by BRENDA team
Al-Masoudi, N.A.; Mahdi, K.M.; Abdul-Rida, N.A.; Saeed, B.A.; Engel, M.
A new pregnenolone analogues as privileged scaffolds in inhibition of CYP17 hydroxylase enzyme. Synthesis and in silico molecular docking study
Steroids
100
52-59
2015
Homo sapiens
Manually annotated by BRENDA team
Ackermann, D.; Pruijm, M.; Ponte, B.; Guessous, I.; Ehret, G.; Escher, G.; Dick, B.; Al-Alwan, H.; Vuistiner, P.; Paccaud, F.; Burnier, M.; Pechere-Bertschi, A.; Martin, P.Y.; Vogt, B.; Mohaupt, M.; Bochud, M.
CYP17A1 enzyme activity is linked to ambulatory blood pressure in a family-based population study
Am. J. Hypertens.
29
484-493
2016
Homo sapiens (P05093)
Manually annotated by BRENDA team
Yoshimoto, F.K.; Peng, H.M.; Zhang, H.; Anderson, S.M.; Auchus, R.J.
Epoxidation activities of human cytochromes P450c17 and P450c21
Biochemistry
53
7531-7540
2014
Homo sapiens (P05093), Homo sapiens
Manually annotated by BRENDA team
Gonzalez, E.; Guengerich, F.P.
Kinetic processivity of the two-step oxidations of progesterone and pregnenolone to androgens by human cytochrome P450 17A1
J. Biol. Chem.
292
13168-13185
2017
Homo sapiens (P05093)
Manually annotated by BRENDA team
Capper, C.P.; Liu, J.; McIntosh, L.R.; Larios, J.M.; Johnson, M.D.; Hollenberg, P.F.; Osawa, Y.; Auchus, R.J.; Rae, J.M.
Functional characterization of the G162R and D216H genetic variants of human CYP17A1
J. Steroid Biochem. Mol. Biol.
178
159-166
2017
Homo sapiens (P05093)
Manually annotated by BRENDA team
Simonov, A.N.; Holien, J.K.; Yeung, J.C.; Nguyen, A.D.; Corbin, C.J.; Zheng, J.; Kuznetsov, V.L.; Auchus, R.J.; Conley, A.J.; Bond, A.M.; Parker, M.W.; Rodgers, R.J.; Martin, L.L.
Mechanistic scrutiny identifies a kinetic role for cytochrome b5 regulation of human cytochrome P450c17 (CYP17A1, P450 17A1)
PLoS ONE
10
e0141252
2015
Homo sapiens (P05093)
Manually annotated by BRENDA team
Kostin, V.A.; Zolottsev, V.A.; Kuzikov, A.V.; Masamrekh, R.A.; Shumyantseva, V.V.; Veselovsky, A.V.; Stulov, S.V.; Novikov, R.A.; Timofeev, V.P.; Misharin, A.Y.
Oxazolinyl derivatives of [17(20)E]-21-norpregnene differing in the structure of A and B rings. Facile synthesis and inhibition of CYP17A1 catalytic activity
Steroids
115
114-122
2016
Homo sapiens (P05093)
Manually annotated by BRENDA team