Information on EC 1.14.14.32 - 17alpha-hydroxyprogesterone deacetylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.32
-
RECOMMENDED NAME
GeneOntology No.
17alpha-hydroxyprogesterone deacetylase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
17alpha-hydroxypregnenolone + [reduced NADPH-hemoprotein reductase] + O2 = 3beta-hydroxyandrost-5-en-17-one + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(2)
-
-
-
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2 = androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C-C bond cleavage
deacylation
-
-
elimination
-
-
of an aldehyde, C-C bond cleavage
-
hydroxylation
-
17alpha-hydroxylation
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen biosynthesis
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-
androgen and estrogen metabolism
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-
Steroid hormone biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
17alpha-hydroxyprogesterone,NADPHhemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating, acetate-releasing)
A microsomal cytochrome P-450 (heme-thiolate) protein that catalyses two independent reactions at the same active site - the 17-hydroxylation of pregnenolone and progesterone, which is part of glucocorticoid hormones biosynthesis (EC 1.14.14.19), and the conversion of the 17-hydroxylated products via a 17,20-lyase reaction to form androstenedione and 3beta-hydroxyandrost-5-en-17-one, leading to sex hormone biosynthesis. The activity of this reaction is dependent on the allosteric interaction of the enzyme with cytochrome b5 without any transfer of electrons from the cytochrome [2,4]. The enzymes from different organisms differ in their substrate specificity. While the enzymes from pig, hamster, and rat accept both 17alpha-hydroxyprogesterone and 17alpha-hydroxypregnenolone, the enzymes from human, bovine, sheep, goat, and bison do not accept the former, and the enzyme from guinea pig does not accept the latter [1].
CAS REGISTRY NUMBER
COMMENTARY hide
62213-24-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
sea bass
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
cynomolgus monkey
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Golden Syrian hamster
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-
Manually annotated by BRENDA team
C57BL/6 mice
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-
Manually annotated by BRENDA team
rainbow trout
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-
Manually annotated by BRENDA team
New Zealand rabbit
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
17-hydroxy-5alpha-pregnan-3alpha-ol-20-one + [reduced NADPH-hemoprotein reductase] + O2
androsterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
17-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxy-5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2
5alpha-androstanedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
17alpha-Hydroxypregnenolone
Dehydroepiandrosterone + acetaldehyde
show the reaction diagram
17alpha-hydroxypregnenolone + ? + cytochrome b5
dehydroepiandrosterone + ?
show the reaction diagram
-
-
-
-
?
17alpha-hydroxypregnenolone + AH2 + O2
?
show the reaction diagram
-
-
-
-
?
17alpha-hydroxypregnenolone + AH2 + O2
dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
17alpha-hydroxypregnenolone + [reduced NADPH-hemoprotein reductase] + O2
3beta-hydroxyandrost-5-en-17-one + acetate + [oxidized NADPH-hemoprotein reductase] + H2
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + ?
androstenedione + ?
show the reaction diagram
-
-
-
?
17alpha-hydroxyprogesterone + AH2 + O2
dehydroepiandrosterone + androstenedione + A + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
17alpha-picolyl-androst-4-en-3beta,17beta-diol + [reduced NADPH-hemoprotein reductase] + O2
? + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
66% conversion in 17,20-lyase reaction
-
?
17beta-hydroxy-17alpha-picolyl-androst-4-en-3-one + [reduced NADPH-hemoprotein reductase] + O2
? + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
73% conversion in 17,20-lyase reaction
-
?
5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxy-5alpha-dihydroprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-17alpha-ol-3,20-dione + ?
androstanedione
show the reaction diagram
-
-
very little product formation
-
-
5alpha-pregnan-3alpha,17alpha-diol-20-one + ? + cytochrome b5
androsterone + ?
show the reaction diagram
-
better substrate than 17alpha-hydroxypregenolone
rapid reaction
-
?
5alpha-pregnan-3alpha-ol-20-one + [reduced NADPH-hemoprotein reductase] + O2
17-hydroxy-5alpha-pregnan-3alpha-ol-20-one + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
7,12-dimethylbenz[a]anthracene + AH2 + O2
?
show the reaction diagram
substrate for CYP17A1
-
-
?
7-dehydro-17alpha-hydroxypregnenolone + AH2 + O2
7-dehydro-dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxy-pregnenolone + A + H2O
show the reaction diagram
-
-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
7alpha-hydroxypregnenolone + [reduced NADPH-hemoprotein reductase] + O2
3beta-hydroxyandrost-5-en-17-one + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
17,20-lyase activity
-
-
?
aflatoxin B1 + AH2 + O2
aflatoxin B1epoxide + A + H2O
show the reaction diagram
substrate for CYP17A1
-
-
?
allopregnanolone + [reduced NADPH-hemoprotein reductase] + O2
androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
?
pregnenolone + reduced acceptor + O2
17alpha-hydroxypregnenolone + oxidized acceptor + H2O
show the reaction diagram
-
i.e. pregn-5-en-3beta-ol-20-one
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + 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 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17-hydroxy-5alpha-pregnan-3alpha-ol-20-one + [reduced NADPH-hemoprotein reductase] + O2
androsterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxy-5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2
5alpha-androstanedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
17alpha-Hydroxypregnenolone
Dehydroepiandrosterone + acetaldehyde
show the reaction diagram
17alpha-hydroxypregnenolone + AH2 + O2
dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
androstenedione + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
5alpha-dihydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxy-5alpha-dihydroprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + [reduced NADPH-hemoprotein reductase] + O2
17-hydroxy-5alpha-pregnan-3alpha-ol-20-one + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
7-dehydro-17alpha-hydroxypregnenolone + AH2 + O2
7-dehydro-dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxy-pregnenolone + A + H2O
show the reaction diagram
P05093
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-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
7alpha-hydroxypregnenolone + [reduced NADPH-hemoprotein reductase] + O2
3beta-hydroxyandrost-5-en-17-one + acetate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
17,20-lyase activity
-
-
?
pregnenolone + reduced acceptor + O2
17alpha-hydroxypregnenolone + oxidized acceptor + H2O
show the reaction diagram
-
i.e. pregn-5-en-3beta-ol-20-one
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + 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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heme
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(17beta)-17-[(5R)-2-(2-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
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(17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
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-
(17beta)-17-[(5R)-2-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
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-
(17beta)-17-[(5R)-2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
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-
(17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
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(17beta)-17-[(5R)-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
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(2S,4aR,4bS,6aS,6bR,7S,9aS,10aS,10bS)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,9,9a,10,10a,10b,11-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-c][1,2]oxazol-2-ol
-
-
(2S,4aR,4bS,6aS,6bS,7S,10aS,10bS)-4a,6a,7-trimethyl-8-(4-methylphenyl)-1,2,3,4,4a,4b,5,6,6a,6b,7,8,10,10a,10b,11-hexadecahydronaphtho[2',1':4,5]indeno[2,1-c]pyrazol-2-ol
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-
(3beta,17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
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(3beta,17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
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(3beta,17beta)-17-[2-(4-chlorophenyl)-5,6-dihydro-4H-1,3-oxazin-4-yl]androst-5-en-3-ol
-
decreases enzyme activity by 70% at 50 M
(5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
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(5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
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(5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
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(5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
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(5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
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(5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
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(5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
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(5'R)-17beta-[2-(4-fluorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
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-
(5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
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1-(3-phenylpropyl)-1H-imidazole
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-
1-(4-bromobenzyl)-1H-imidazole
-
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1-(4-iodo-benzyl)-1H-imidazole
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1-(4-phenylbutyl)-1H-imidazole
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1-(5-phenylpentyl)-1H-imidazole
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1-(7-phenyl-heptyl)-1H-imidazole
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1-[3-(4-bromo-phenyl)-propyl]-1H-imidazole
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1-[3-(4-chlorophenyl)-propyl]-1H-imidazole
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1-[3-(4-fluorophenyl)-propyl]-1H-imidazole
-
-
1-[5-(4-bromo-phenyl)-pentyl]-1H-imidazole
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-
1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole
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-
1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole
-
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1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole
-
-
17(E)-picolinyliden-androst-4-en-3beta-ol
-
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17(E)-picolinyliden-androst-5-en-3beta-ol
-
-
17-(1H-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
-
VN/85-1
17-(1H-imidazole-1-yl)androsta-4,16-dien-3-one
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VN/108-1
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-4-en-3-one
-
; 91% relative conversion at 0.05 mM
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
; 74% relative conversion at 0.05 mM
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-4-en-3-one
-
; 78% relative conversion at 0.05 mM
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-4-en-3-one
-
; 34% relative conversion at 0.05 mM
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-4-en-3-one
-
; 69% relative conversio at 0.05 mMn
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-4-en-3-one
-
; 54% relative conversion at 0.05 mM
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
; 95% relative conversion at 0.05 mM
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-4-en-3-one
-
; 91% relative conversion at 0.05 mM
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolyl-3-pyrazolyl)androst-4-en-3-one
-
; 92% relative conversion at 0.05 mM
17beta-(1-p-tolyl-5-pyrazolyl)androst-4-en-3-one
-
; 86% relative conversion at 0.05 mM
17beta-(1-p-tolyl-5-pyrazolyl)androst-5-en-3beta-ol
-
89% relative conversion at 0.05 mM
17beta-(1-p-tolylphenyl-3-pyrazolyl)androst-5-en-3beta-
-
-
17beta-(1-p-tolylphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
93% relative conversion at 0.05 mM
17beta-(1-p-tolylphenyl-5-pyrazolyl)androst-5-en-3beta-
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-4-en-3-one
-
; 86% relative conversion at 0.05 mM
17beta-(1-phenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
; 65% relative conversion at 0.05 mM
17beta-(1-phenyl-5-pyrazolyl)androst-4-en-3-one
-
; 87% relative conversion at 0.05 mM
17beta-(1-phenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
; 92% relative conversion at 0.05 mM
17beta-(2-oxazolidon-5-yl)-androst-4-en-3-one
-
-
17beta-(2-oxazolidon-5-yl)androst-5-en-3beta-ol
-
-
17beta-[3-(N-3,5-dimethylphenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-3,5-dimethylphenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-bromophenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-bromophenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-chlorophenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-chlorophenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-fluorophenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-fluorophenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-methoxyphenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-methoxyphenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-phenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-phenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',4'-dimethyl-4',5'-dihydro-1',3'-oxazole
-
-
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
-
-
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
-
-
3-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
3-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
3beta-acetoxy-21-chloropregn-5-ene-20beta-N-phenylurethane
-
-
3beta-acetoxy-5alpha,6beta,17alpha,21-tetrabromo-pregnane-20-one
-
-
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
VN/87-1
3beta-hydroxy-17-(1H-benzimidazol-1-yl)androsta-5,16-diene
-
VN/124-1
3beta-hydroxy-17-(1H-benzimidazole-1-yl)androsta-5,16-diene
-
VN/124-1
3beta-hydroxy-17-(50-[30-methyl]-10,20,40-oxadiazolyl)androst-5,16-diene
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-nitrobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethylphenyl)-4-toluenesulfonate
-
-
4-iodobenzyl imidazole
-
-
4-nonylphenol
-
strong inhibitory effect at 0.1 mM
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-(4-fluorophenyl)-1-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-ol
-
-
6-(3,4-difluorophenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-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
-
-
abiraterone
abiraterone acetate
-
bitertanol
-
cyclopregnenolone
-
i.e. 3alpha5-cyclo-6beta-methoxy-5alpha-pregnane-20-one
diethylstilbestrol
-
-
dioctyltin chloride
-
-
estradiol-17beta
-
concentration of 0.3 mM both, testicular and male duodenal enzyme with exogenous 17alpha-hydroxyprogesterone as substrate are inhibited by 30-40%
fluconazole
-
flusilazole
Insulin
-
acute and selective
-
ketoconazole
methylmercury
-
-
O-3beta-acetoxyandrost-5,16-diene-17-acyl-p-methoxybenzamidoxime
-
compound displays in vitro cytotoxic activity against HeLa cells, MCF-7 cells, A-2780 cells and A-431 cells which are higher than or comparable to that of the reference cisplatin
O-3beta-acetoxyandrost-5,16-diene-17-acylacetamidoxime
-
compound displays in vitro cytotoxic activity against HeLa cells, MCF-7 cells, A-2780 cells and A-431 cells which are higher than or comparable to that of the reference cisplatin
Promegestone
-
competitive
Propiconazole
-
SU10603
tebuconazole
tetrabromobisphenol A
-
-
TOK-001
-
-
triadimenol
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
-
P450 oxidoreductase
-
-
-
PD98059
-
inhibitor of the MEK/ERK pathway. Treatment of cells with PD98059 (10 mM) at 24 and 48 h results in significant increases in the protein levels of CYP17. Production of androstenedione and estradiol significantly increases after treatment with PD98059
additional information
-
serine phosphorylation of P450c17
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00027 - 0.00039
17alpha-hydroxypregnenolone
0.000015 - 0.000675
17alpha-hydroxyprogesterone
0.0006
5alpha-pregnan-3alpha,17alpha-diol-20-one
-
pH 7.4
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
10 - 128
17alpha-hydroxypregnenolone
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000553 - 0.000207
1-(7-phenyl-heptyl)-1H-imidazole
0.00004 - 0.000208
1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole
0.000052 - 0.000265
1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole
0.0000215 - 0.0000775
1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole
0.000665 - 0.00124
ketoconazole
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.014
(17beta)-17-[(5R)-2-(2-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
Rattus norvegicus
-
37C
0.0048
(17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
Rattus norvegicus
-
37C
0.005
(17beta)-17-[(5R)-2-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
Rattus norvegicus
-
37C
0.052
(17beta)-17-[(5R)-2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
Rattus norvegicus
-
37C
0.0077
(17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
Rattus norvegicus
-
37C
0.03
(17beta)-17-[(5R)-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]androst-4-en-3-one
Rattus norvegicus
-
37C
0.026
(2S,4aR,4bS,6aS,6bR,7S,9aS,10aS,10bS)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,9,9a,10,10a,10b,11-hexadecahydro-1H-naphtho[2',1':4,5]indeno[2,1-c][1,2]oxazol-2-ol
Rattus norvegicus
-
37C
0.0058
(2S,4aR,4bS,6aS,6bS,7S,10aS,10bS)-4a,6a,7-trimethyl-8-(4-methylphenyl)-1,2,3,4,4a,4b,5,6,6a,6b,7,8,10,10a,10b,11-hexadecahydronaphtho[2',1':4,5]indeno[2,1-c]pyrazol-2-ol
Rattus norvegicus
-
37C
0.011
(3beta,17beta)-17-[(5R)-2-(3-chlorophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
Rattus norvegicus
-
37C
0.0079
(3beta,17beta)-17-[(5R)-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazol-5-yl]androst-5-en-3-ol
Rattus norvegicus
-
37C
0.0048
(5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
Rattus norvegicus
-
pH 7.3, 37C
0.014
(5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
Rattus norvegicus
-
pH 7.3, 37C
0.005
(5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
Rattus norvegicus
-
pH 7.3, 37C
0.052
(5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
Rattus norvegicus
-
pH 7.3, 37C
0.0077
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
Rattus norvegicus
-
pH 7.3, 37C
0.0079
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
Rattus norvegicus
-
pH 7.3, 37C
0.03
(5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
Rattus norvegicus
-
pH 7.3, 37C
0.00614 - 0.03095
1-(3-phenylpropyl)-1H-imidazole
0.00285 - 0.01655
1-(4-bromobenzyl)-1H-imidazole
0.00158 - 0.01006
1-(4-iodo-benzyl)-1H-imidazole
0.00223 - 0.00865
1-(4-phenylbutyl)-1H-imidazole
0.00131 - 0.0022
1-(5-phenylpentyl)-1H-imidazole
0.0001 - 0.00032
1-(7-phenyl-heptyl)-1H-imidazole
0.00033 - 0.00295
1-[3-(4-bromo-phenyl)-propyl]-1H-imidazole
0.00055 - 0.00585
1-[3-(4-chlorophenyl)-propyl]-1H-imidazole
0.00196 - 0.02781
1-[3-(4-fluorophenyl)-propyl]-1H-imidazole
0.000058 - 0.0005
1-[5-(4-bromo-phenyl)-pentyl]-1H-imidazole
0.000086 - 0.00057
1-[5-(4-chlorophenyl)-pentyl]-1H-imidazole
0.0001 - 0.00075
1-[5-(4-fluorophenyl)-pentyl]-1H-imidazole
0.000057 - 0.00017
1-[7-(4-fluorophenyl)-heptyl]-1H-imidazole
0.014
17(E)-picolinyliden-androst-4-en-3beta-ol
Rattus norvegicus
-
C17,20-lyase activity, pH 7.3, 37C
0.0082
17(E)-picolinyliden-androst-5-en-3beta-ol
Rattus norvegicus
-
C17,20-lyase activity, pH 7.3, 37C
0.022
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-4-en-3-one
Rattus norvegicus
-
; pH and temperature not specified in the publication
0.059
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-4-en-3-one
Rattus norvegicus
-
-
0.059
17beta-(1-phenyl-5-pyrazolyl)androst-4-en-3-one
Rattus norvegicus
-
pH and temperature not specified in the publication
0.003
17beta-(2-oxazolidon-5-yl)-androst-4-en-3-one
Rattus norvegicus
-
-
0.013
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',4'-dimethyl-4',5'-dihydro-1',3'-oxazole
Homo sapiens
-
at pH 7.4 and 37C
0.0009
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
Homo sapiens
-
at pH 7.4 and 37C
0.00006
3beta-hydroxy-17-(50-[30-methyl]-10,20,40-oxadiazolyl)androst-5,16-diene
Rattus norvegicus
-
pH 7.3, 37C
0.0002908
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
Rattus norvegicus
-
at 37C
0.0000704
4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
Rattus norvegicus
-
at 37C
0.0000987
4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
Rattus norvegicus
-
at 37C
0.00021
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
Rattus norvegicus
-
at 37C
0.0000651
4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
Rattus norvegicus
-
at 37C
0.0001009
4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
Rattus norvegicus
-
at 37C
0.000085
4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
Rattus norvegicus
-
at 37C
0.00023
4-(1H-imidazol-1-ylmethylphenyl)-4-toluenesulfonate
Rattus norvegicus
-
at 37C
0.00158
4-iodobenzyl imidazole
Rattus norvegicus
-
at 37C
0.0000012 - 0.0013
abiraterone
0.014
diethylstilbestrol
Sus scrofa
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.000084
dioctyltin chloride
Homo sapiens
-
H295R cell assay, pH and temperature not specified in the publication
0.00013 - 0.016
flusilazole
0.000032 - 0.00376
ketoconazole
0.02 - 2
methylmercury
Sus scrofa
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.000039 - 0.000061
SU10603
0.00014
tebuconazole
Sus scrofa
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.093
tetrabromobisphenol A
Sus scrofa
-
adrenal cortex microsomes, pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000073
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.0000375
-
H295R cell assay, pH and temperature not specified in the publication
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3
-
assay at
7.4
-
activity assay
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
weakly present
Manually annotated by BRENDA team
-
human adrenocorticocarcinoma cell line
Manually annotated by BRENDA team
-
is most consistent in the testicular interstitial cells surrounding existing or developing cysts
Manually annotated by BRENDA team
weakly present
Manually annotated by BRENDA team
-
peripheral blood leukocyte
Manually annotated by BRENDA team
-
ovarian granulosa-like tumor cell line, most of the cells are strongly positive for CYP17 and CYP19, especially in the perinuclear region
Manually annotated by BRENDA team
-
peripheral blood leukocyte
Manually annotated by BRENDA team
-
intensely present during the breeding season
Manually annotated by BRENDA team
weakly present
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
perinucleus
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
54000
-
immunoblot analysis
57000
-
Western blotting, SDS-PAGE
58000
-
x * 58000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
resonance Raman spectroscopy of ferric form reveals that binding of substrate causes variable degrees of conversion from the low spin to high spin state, with the nonhydroxylated progesterone and pregnenolone yielding almost complete high spin form, while the two hydroxylated substrates (17-hydroxyprogesterone and 17-hydroxypregnenolone) give only about a 60% conversion to high spin. The heme structure and its interactions with the active site protein residues remain constant for all four substrates
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimethyl sulfoxide
-
5% v/v, no significant reduction of activity
propylene glycol
-
3% v/v, no significant reduction of activity
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Pichia pastoris
-
full length cDNA clone encoding cytochrome P-450c17 (17alpha-hydrolase/17,20 lyase), expression in mammalian COS-1 cells
-
full length cDNA clone encoding cytochrome P450C17 expressed in COS 1 cells
-
gene CYP17A1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, expression of wild-type and mutant enzymes in COS-1 cells
gene encoding cytochrome P450 17alpha-hydrolase/C17-20-lyase (P450 17alpha)
-
recombinant expression in Escherichia coli
-
sequence comparisons and phylogenetic analysis
wild-type or mutant CYP17A1 cDNA, after addition of an N-terminal myc-tag, inserted into a pcDNA3.1 vector, transiently transfected into confluent COS-1 cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CYP17 mRNA levels are reduced by 50% in CYP17 chimeric compared to wild-type mouse brain, whereas the levels of brain dehydroepiandrosterone levels are comparable
CYP17A1 gene expression continuously rises throughout the ovarian development, except for a slight drop during the primary yolk stage. During the atretic follicles stage, the expression of CYP17A1 is remarkably upregulated and reaches the highest level. During the tertiary yolk stage, brain CYP17AI expression is 3.1fold higher than the primary yolk stage, and 4.4fold higher than that at atretic follicles stage
in the brain, during the atretic follicles stage, the gene expression drops sharply to the lowest level
shRNA treatment significantly decreases CYP17 mRNA and protein levels in vitro. Silence efficiency of three constructed lentivirus shRNAs is 65.5%, 73.7% and 77.4%, respectively. Three constructed lentivirus shRNAs also have silencing effects on CYP17 protein expression, and their silence efficiencies are 50%, 50% and 61%, respectively. In vivo, shRNA still has a specific silencing effect on CYP17
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A355T
-
shows a complete loss of enzymatic activity. Is expressed in transfected COS-1 cells in a fashion comparable to the wild-type protein. Less severely affected patient with ambiguous genitalia
D298V
mutant without heme-binding properties
DELTAF54
-
partially reduces enzymatic activities
E305G
-
naturally occurring P450 17A1 mutation, impairs 17,20-lyase activity. Cytochrome b5 fails to rescue the poor coupling with 17-hydroxypregnenolone
G111D
mutant without heme-binding properties
G111S
-
shows a complete loss of enzymatic activity. Is expressed in transfected COS-1 cells in a fashion comparable to the wild-type protein. Leads to complete lack of masculinization in the patient
G301I
mutant without heme-binding properties
G90D
the mutation results in loss of the 17alpha-hydroxylase and 17,20-lyase activities
H373N
-
mutation almost completely eliminates enzymatic activities
I332T
-
retains some residual 17,20-lyase activity (10%). Is expressed in transfected COS-1 cells in a fashion comparable to the wild-type protein. Less severely affected patient with ambiguous genitalia
P342T
the mutant shows 20% of wild type activity
Q461stop
naturally occuring mutation, inactive mutant
R358Q
naturally occuring mutation, results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions, the mutant CYP17A1 loses the ability to interact with cytochrome b5 in recombinant COS-1 cells. Molecular modeling experiments indicate that substitution R358Q neutralizes surface positive charges in the region responsible for redox-partner binding; the mutation results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions
R358X
-
mutant, CGA to TGA, alteration introduces premature stop codon, inactive protein
R440H
-
shows a complete loss of enzymatic activity. Leads to complete lack of masculinization in the patient
R449A
naturally occuring mutation, results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions; the mutation causes loss of 17,20-lyase activity
R496C
naturally occuring mutation, the mutant has low 17alpha-hydroxylase and 17,20-lyase activities
R96W
the mutation results in loss of the 17alpha-hydroxylase and 17,20-lyase activities
S106P
the mutation results in loss of the 17alpha-hydroxylase and 17,20-lyase activities
T64S
the mutant shows 15% of wild type activity
Y329DEL-SUB
-
mutant, TAC to AA, alteration introduces premature stop codon, inactive protein
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
medicine