Information on EC 1.14.14.19 - steroid 17alpha-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.19
-
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
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C-C bond cleavage
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C17-C20 bond cleavage
C-C-bond cleavage
-
-
deacylation
-
-
hydroxylation
oxidation
-
-
-
-
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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Metabolic pathways
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Steroid hormone biosynthesis
-
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androgen and estrogen metabolism
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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 4.1.2.30, 7alpha-hydroxyprogesterone aldolase). 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
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UniProt
Manually annotated by BRENDA team
air-breathing catfish, gene p450c17
SwissProt
Manually annotated by BRENDA team
gene CYP17A1
UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
cynomolgus monkey
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-
Manually annotated by BRENDA team
GenBank accession numbers L40335 and AF251388 encodíng isozymes 1 and 2; two isozymes of cytochrome P450 17alpha-hydroxylase/17,20-lyase, that differ in two nucleotides, resulting in variants Ser210Gly and Tyr464Asn
UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
; male frogs
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-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
from Shandong coastal area, genes P450c17-I and P450c17-II
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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
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
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
pregnenolone + [reduced NADPH.hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + [reduced NADPH—hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH—hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
progesterone + 2 AH2 + 2 O2
androstenedione + acetate + 2 A + 2 H2O
show the reaction diagram
via 17alpha-hydroxyprogesterone
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
show the reaction diagram
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + H+ + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + 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
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-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
-
-
-
-
?
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
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
progesterone + 2 AH2 + 2 O2
androstenedione + acetate + 2 A + 2 H2O
show the reaction diagram
A6P663
via 17alpha-hydroxyprogesterone
-
-
?
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 + NADPH + H+ + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + 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
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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NADPH
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
(+)-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
(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
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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
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
-
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-(4-thiophen-3-yl-phenyl)ethyl)-1H-imidazole
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1-(1-(4-thiophen-3-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-(10-phenyl-decyl)-1H-imidazole
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65.2% inhibition at 0.01 mM
1-(10-phenyldecyl)-1H-1,2,4-triazole
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79.6% inhibition at 0.1 mM
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-(2-phenyl-ethyl)-1H-imidazole
-
10.6% inhibition at 0.01 mM
1-(2-phenylethyl)-1H-1,2,4-triazole
-
10.9% inhibition at 0.1 mM
1-(3,4-dichlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0122 mM, of 17,20-lyase activity at 0.0021 mM
1-(3,5-dibromobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0259 mM, of 17,20-lyase activity at 0.00316 mM
1-(3,5-dichlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0226 mM, of 17,20-lyase activity at 0.0033 mM
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
-
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1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(3-phenyl-propyl)-1H-imidazole
-
23.4% inhibition at 0.01 mM
1-(3-phenylpropyl)-1H-1,2,4-triazole
-
17.2% inhibition at 0.1 mM
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-bromobenzyl)-1H-imidazole
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50% inhibition of hydroxylase activity at 0.0165 mM, of 17,20-lyase activity at 0.0028 mM
1-(4-chlorobenzyl)-1H-imidazole
1-(4-fluorobenzyl)-1H-imidazole
-
-
1-(4-furan-3-ylbenzyl)-1H-imidazole
-
-
1-(4-iodobenzyl)-1H-imidazole
1-(4-methylbenzyl)-1H-imidazole
-
-
1-(4-nitrobenzyl)-1H-imidazole
1-(4-phenyl-butyl)-1H-imidazole
-
40.7% inhibition at 0.01 mM
1-(4-phenylbutyl)-1H-1,2,4-triazole
-
29% inhibition at 0.1 mM
1-(5-phenyl-pentyl)-1H-imidazole
-
59.7% inhibition at 0.01 mM
1-(5-phenylpentyl)-1H-1,2,4-triazole
-
55% inhibition at 0.1 mM
1-(6-phenyl-hexyl)-1H-imidazole
-
61.3% inhibition at 0.01 mM
1-(6-phenylhexyl)-1H-1,2,4-triazole
-
60.4% inhibition at 0.1 mM
1-(7-phenyl-heptyl)-1H-imidazole
-
67.5% inhibition at 0.01 mM
1-(7-phenylheptyl)-1H-1,2,4-triazole
-
73.2% inhibition at 0.1 mM
1-(8-phenyl-octyl)-1H-imidazole
-
70.2% inhibition at 0.01 mM
1-(8-phenyloctyl)-1H-1,2,4-triazole
-
76.6% inhibition at 0.1 mM
1-(9-phenyl-nonyl)-1H-imidazole
-
64.5% inhibition at 0.01 mM
1-(9-phenylnonyl)-1H-1,2,4-triazole
-
79.1% inhibition at 0.1 mM
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-benzyl-1H-1,2,4-triazole
-
6.8% inhibition at 0.1 mM
1-benzyl-1H-imidazole
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
1-[(5,7-dichlorobenzofuran-2-yl)methyl]imidazole
1-[(5-bromobenzofuran-2-yl)methyl]imidazole
1-[(5-chlorobenzofuran-2-yl)methyl]imidazole
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-[3-(4-bromophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.00295 mM, of 17,20-lyase activity at 0.00033 mM
1-[3-(4-chlorophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0058 mM, of 17,20-lyase activity at 0.00055 mM
1-[3-(4-fluorophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.02781 mM, of 17,20-lyase activity at 0.00196 mM
1-[4-(1H-imidazol-1-ylmethyl)phenyl]methanimine
-
-
1-[4-(4-methylthiophen-3-yl)benzyl]-1H-imidazole
-
-
1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
-
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(E)-picolinyliden-androst-4-en-3-one
-
complete inhibition at 0.05 mM
-
17(E)-picolinyliden-androst-4-en-3beta-ol
-
52% inhibition at 0.05 mM
-
17(E)-picolinyliden-androst-5-en-3beta-ol
-
55% inhibition at 0.05 mM
-
17-((1-(2-(trifluoromethyl)-1H-benzimidazol-5-yl)imino)ethyl)-5-pregnen-3beta-ol
-
78.61% inhibition at 0.01 mM
-
17-((1-(6-methoxybenzothiazol-2-yl)imino)ethyl)-5-pregnen-3beta-ol
-
81.99% inhibition at 0.01 mM
-
17-(1-(n-hexylamino)-1-hydroxyethyl)-5-pregnen-3beta-ol
-
62.52% inhibition at 0.01 mM
-
17-(1H-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
17-(1H-1,2,4-triazol-1-yl)androsta-4,16-dien-3-one
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
17-(2-amino-4-thiazolyl)-androsta-5,16-dien-3beta-ol
-
type II competitive inhibitor
17-(3'-pyrazolyl)androsta-4,16-dien-3beta-one
17-(3'-pyrazolyl)androsta-5,16-dien-3beta-ol
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
17-(methylthio)androst-5-en-3beta-ol S-oxide
-
type I 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
17alpha-picolyl-androst-4-en-3beta,17beta-diol
-
10% inhibition at 0.05 mM
-
17alpha-picolyl-androst-5-en-3beta,17beta-diol
-
5% inhibition at 0.05 mM
-
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-tolyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-tolylphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolylphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-phenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-phenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(cyclopropylamino)-androst-5-en-3beta-ol
-
mechanism-based inhibitor, irreversible inhibition
17beta-acetamidoandrost-4-en-3-one
-
-
17beta-hydroxy-17alpha-picolyl-androst-4-en-3-one
-
13% inhibition at 0.05 mM
-
17beta-ureidoandrosta-1,4-dien-3-one
-
-
19-azido-androstenedione
-
-
19-thiomethyl-androstenedione
-
-
2-((1-(5-pregnen-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-(1H-imidazol-4-ylmethyl)-9H-carbazole
-
suicide inhibitor
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(S)-20,21-aziridinylpregn-5-en-3beta-ol
-
type II competitive inhibitor
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
20xi-hydroxy-21-trifluoropregn-4-en-3-one
21-hydroxyimino-21-methylpregn-4-en-3-one
-
at 0.0036 mM 50% inhibition
21-hydroxyiminopregn-4-en-3-one
21-hydroxyiminopregn-5-en-3beta-ol
21-hydroxyiminopregna-4,17(20)-dien-3-one
21-hydroxyiminopregna-5,17(29)-dien-3beta-ol
21-methylpregn-5-en-3beta-ol-21-one
-
at 0.0098 mM 50% inhibition
21-trifluoropregn-4-en-3,20-dione
-
at 0.0021 mM 50% inhibition
21-trifluoropregn-5-en-3beta,20xi-diol
-
at 0.0044 mM 50% inhibition
22-Amino-23,24-bisnor-5-cholen-3beta-ol
-
type II competitive inhibitor
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-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-(6-Chloro-3-methyl-2-indenyl)pyridine
-
competitive inhibitor
3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3-pyridyl-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene
-
suicide inhibitor
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
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
3beta-hydroxy-23,24-bisnor-5-cholenic-hydroxamic acid
3beta-hydroxy-5-androsten-17beta-hydroxamic acid
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-pregnen-3beta-ol-17-yl)ethylidene)amino)-3-methoxybenzoic acid
-
43.34% inhibition at 0.01 mM
-
4-((1-(5-pregnen-3beta-ol-17-yl)ethylidene)amino)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
-
56.23% inhibition at 0.01 mM
-
4-((1-(5-pregnen-3beta-ol-17-yl)ethylidene)amino)-N-(isoxazol-3-yl)benzenesulfonamide
-
81.78% inhibition at 0.01 mM
-
4-((1-(5-pregnen-3beta-ol-17-yl)ethylidene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
-
16.27% inhibition at 0.01 mM
-
4-((1-(5-pregnen-3beta-ol-17-yl)ethylidene)amino)benzenesulfonamide
-
57.1% inhibition at 0.01 mM; 78.84% inhibition at 0.01 mM
-
4-((1-(5-pregnen-3beta-ol-17-yl)ethylidene)amino)benzenesulfonic acid
-
8.37% inhibition at 0.01 mM
-
4-((1-(5-pregnen-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)phenol
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
-
-
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 4-pentylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl benzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
-
-
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-amino-17beta-(cyclopropylamino)-androst-4-en-3-one
-
suicide inhibitor
4-amino-17beta-(cyclopropyloxy)-androst-4,6-dien-3-one
-
suicide inhibitor
4-amino-17beta-(cyclopropyloxy)-androst-4-en-3-one
-
suicide inhibitor
4-chloro-3,4-dihydro-2-(3-pyridyl)-1-(2H)-naphthalenone
-
competitive inhibitor
4-hydroxybenzyl imidazole
4-iodobenzyl 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-[(3-chlorophenyl-1H-imidazole-1-yl)methyl]-1H-benzimidazole
-
suicide inhibitor
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
and 3,5,4'-trimethylresveratrol
-
inhibition by is more selective on the 17,20-lyase activity than hydroxylase activity of CYP17A1
-
benzyl imidazole
-
-
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
-
supresses 17alpha-hydrolase and C17,20-lyase activity below pH 6.3-6.5
-
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
Emulgen 913
-
at 0.2% w/v 94% inhibition
estradiol-17beta
-
inhibits both and C17,20 lyase activity in testis and duodenum, competitive inhibitor
iodoacetate
-
at 1 mM 100% inhibition of 17alpha-hydroxylation and 50% inhibition of lyase activity
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-pregnen-3beta-ol-17-yl)ethylidene)amino)benzene sulfonamide
-
48.37% inhibition at 0.01 mM
-
N-(4-((1-(5-pregnen-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'-[(1S)-1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]biphenyl-3-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
nitrogen
-
complete inhibition
p-chloromercuribenzoate
-
at 1 mM complete inhibition
pregnenolone
-
-
progesterone
-
-
resveratrol
-
i.e. trans-3,5,4'-trihydroxystilbene
siRNA
-
siRNA targeting the CYP17 gene
-
sodium cholate
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
-
toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
-
-
transforming growth factor-beta1
-
inhibits 17alpha-hydroxylation in vitro by a noncompetitive mechanism
-
VN/124-1
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a 17alpha-hydroxylase/17,20 lyase inhibitor, is cytotoxic in prostate cancer cells and synergistically induces endoplasmic reticulum stress, mechanism, overview
VN/85-1
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-
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YM-116
Z-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
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at 0.0025 mM 5% inhibition
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
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[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
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[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
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-
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CYP21
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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
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cytochrome b5
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phosphatidylcholine
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incorporation of P450 into liposomal membranes composed of phosphatidylcholine increases activity
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0004 - 0.0008
17-hydroxypregnenolone
0.0009 - 0.0017
17alpha-hydroxypregnenolone
0.000525 - 0.0025
17alpha-hydroxyprogesterone
0.018
5alpha-pregnan-3alpha-ol-20-one
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pH 7.4
0.00008 - 0.0093
pregnenolone
0.0000142 - 0.03
progesterone
additional information
additional information
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calculation of intramolecular and intermolecular kinetic isotope effects for wild-type and mutant enzymes, overview
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00283
17alpha-hydroxypregnenolone
Homo sapiens
-
-
0.0065 - 0.85
pregnenolone
0.017 - 1.6
progesterone