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Information on EC 1.14.14.19 - steroid 17alpha-monooxygenase
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1.14.14.19 steroid 17alpha-monooxygenaseIUBMB 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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Word Map
- 1.14.14.19
- adrenal
- androgen
- progesterone
- testosterone
- steroidogenesis
- androstenedione
- cortisol
- cyp17a1
- dehydroepiandrosterone
- estrogen
- pregnenolone
- aromatase
- estradiol
- testicular
- acth
-
adrenocortical
- p450scc
- 17-hydroxyprogesterone
- dheas
- hypokalemia
- 21-hydroxylase
-
3beta-hydroxysteroid
-
mineralocorticoid
- ketoconazole
- p450arom
- 3beta-hsd
- hyperandrogenism
- 17-hydroxypregnenolone
- abiraterone
-
theca
- 17alpha-hydroxyprogesterone
- reticularis
-
amenorrhea
- orteronel
- 11-deoxycortisol
-
alpha-hydroxypregnenolone
- pseudohermaphroditism
-
17-hydroxylation
-
delta4
-
acth-stimulated
- aminoglutethimide
-
adrenarche
- genitalia
- 11-deoxycorticosterone
-
17alpha-hydroxylation
- analysis
- cyp21a2
-
c19-steroids
-
nonsteroidogenic
-
hypergonadotropic
- medicine
- drug development
-
nci-h295r
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
17 alpha-hydroxylase/C17,20-lyase, 17,20-lyase, 17-alpha-hydroxylase/C17-20 lyase, 17-hydroxylase/17,20-lyase, 17-hydroxylase/C17,20-lyase, 17alphahydroxylase, 17alpha-hydroxylase, 17alpha-hydroxylase 17,20 lyase, 17alpha-hydroxylase-17,20-lyase, 17alpha-hydroxylase-C17,20 lyase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17 alpha-hydroxylase/C17,20-lyase
17,20-lyase
17-hydroxylase/17,20-lyase
17alpha-hydroxylase
17alpha-hydroxylase-C17,20 lyase
-
-
-
-
17alpha-hydroxylase-C17,20-lyase
17alpha-hydroxylase/17,20-lyase
17alpha-OHase
CYP17
CYP17A1
CYPXVII
-
-
-
-
cytochrome P-450 (P45017alpha,lyase)
-
-
-
-
cytochrome P450 17A1
cytochrome P450 17alpha-hydroxylase/17,20 lyase
cytochrome P450 17alpha-hydroxylase/17,20-lyase
cytochrome p450 17alpha-hydroxylase/C(17,20)-lyase
cytochrome P45017alpha
cytochrome P450c17
EC 1.14.1.7
-
-
formerly
-
EC 1.99.1.9
-
-
formerly
-
P450 17
P450-C17
-
-
-
-
P45017alpha
P450c17
Steroid 17-alpha-hydroxylase/17,20 lyase
-
-
-
-
steroid 17alpha-hydroxylase
CYP17
-
-
CYP17A1
-
cytochrome P45017alpha
-
-
-
-
steroid 17alpha-hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2 = a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2 = a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2 = a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
the hydroxylation reaction is believed to proceed through a conventional Compound I rebound mechanism. Thr306 is a member of the conserved acid/alcohol pair essential for the efficient delivery of protons required for hydroperoxoanion heterolysis and formation of Compound I in the cytochromes P450. Involvement of a nucleophilic peroxo-anion rather than the traditional Compound I in catalysis. The peroxoanion is required to initiate O-O bond scission and formation of the Cpd I reactive intermediate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydroxylation
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
hydroxylation
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
steroid,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating)
Requires NADPH and EC 1.6.2.4, NADPH---hemoprotein reductase. A microsomal hemeprotein that catalyses two independent reactions at the same active site - the 17alpha-hydroxylation of pregnenolone and progesterone, which is part of glucocorticoid hormones biosynthesis, and the conversion of the 17alpha-hydroxylated products via a 17,20-lyase reaction to form androstenedione and dehydroepiandrosterone, leading to sex hormone biosynthesis (EC 1.14.14.32, 17alpha-hydroxyprogesterone deacetylase). The ratio of the 17alpha-hydroxylase and 17,20-lyase activities is an important factor in determining the directions of steroid hormone biosynthesis towards biosynthesis of glucocorticoid or sex hormones.
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CAS REGISTRY NUMBER
COMMENTARY
9029-67-8
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
16,17-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
16,17-dehydroprogesterone + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
-
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH + O2
5alpha-pregnan-17alpha-ol-3,20-dione + NADP+ + H2O
-
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NADPH + O2
5alpha-pregnan-3alpha,17alpha-diol-20-one + ?
-
-
-
-
?
7-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
7-dehydro-17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
progesterone + 2 AH2 + 2 O2
androstenedione + acetate + 2 A + 2 H2O
via 17alpha-hydroxyprogesterone
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
cytochrome b5 also as cofactor
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
17,20-lyase activity
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
via Compound I intermediate
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
via the catalytic cycle involving an iron(IV) oxo intermediate
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
-
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
-
reaction via 17alpha-hydroxyprogesterone
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
product ratio is 3:1
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
isoform P450 17A1 has 3fold higher catalytic efficiency in the 17alpha-hydroxylation of progesterone than pregnenolone
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
17,20-lyase activity
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
via Compound I intermediate
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
additional information
?
-
-
the enzyme catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
?
additional information
?
-
-
the bifunctional enzyme also exhibits 17,20-lyase activity converting 17alpha-hydroxypregnenolone to dehydroepiandrosterone-S, EC 4.1.2.30, overview
-
-
?
additional information
?
-
enzyme effectively catalyzes hydroxylation reaction for both progesterone and pregnenolone, with 17alpha-hydroxyprogesterone, also 17,20-lyase activity is realized
-
-
?
additional information
?
-
-
the enzyme catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
?
additional information
?
-
-
the bifunctional enzyme also exhibits 17,20-lyase activity converting 17alpha-hydroxypregnenolone to dehydroepiandrosterone-S, EC 4.1.2.30, overview
-
-
?
additional information
?
-
P450c17 is an enzyme type that lacks lyase activity
-
-
?
additional information
?
-
-
P450c17 is an enzyme type that lacks lyase activity
-
-
?
additional information
?
-
isoform P450 17A1 also exhibits 17alpha,20-lyase activity
-
-
?
additional information
?
-
isoform P450 17A1 also exhibits 17alpha,20-lyase activity
-
-
?
additional information
?
-
-
isoform P450 17A1 also exhibits 17alpha,20-lyase activity
-
-
?
additional information
?
-
both the lyase and hydroxylase activities proceed from a common steroid-binding geometry by an iron oxene mechanism
-
-
?
additional information
?
-
-
both the lyase and hydroxylase activities proceed from a common steroid-binding geometry by an iron oxene mechanism
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
catalyzes the last step of androgen biosynthesis in both testes and adrenals
-
-
?
additional information
?
-
-
enzyme also catalyzes 17,20-lyase reaction, EC4.1.2.30
-
-
?
additional information
?
-
-
CYP17 is a key enzyme in steroid hormone biosynthesis
-
-
?
additional information
?
-
-
the enzyme is is essential for the maintenance of normal male and female sexual characteristics, as well as the stress response and mineral balance in all mammals
-
-
?
additional information
?
-
-
the enzyme is required for androgen production, genetic regulation, overview
-
-
?
additional information
?
-
-
the bifunctional enzyme also exhibits 17,20-lyase activity converting 17alpha-hydroxypregnenolone to dehydroepiandrosterone-S, EC 4.1.2.30, overview
-
-
?
additional information
?
-
-
the bifunctional enzyme also exhibits 17,20-lyase activity converting 17alpha-hydroxypregnenolone to dehydroepiandrosterone-S, EC 4.1.2.30, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes both the 17alpha-hydroxylation of C21-steroids, pregnenolone and progesterone, and the subsequent 17,20-lyase reaction, EC 4.1.2.30, cleaving the C17-C20 bond of 17alpha-hydroxylated intermediates, 17alpha-hydroxyprenenolone and 17alpha-hydroxyprogesterone to yield C19 androgens, dehydroepiandrosterone and androstenedione, respectively, overview
-
-
?
additional information
?
-
-
CYP17 is the cytochrome b5 modulated key enzyme for the biosynthesis of androgens, catalyzing the 17alpha-hydroxylation of pregnenolone and progesterone and the subsequent cleavage of the C 20,21-acetyl group to yield the corresponding androgens dehydroepiandrosterone and androstendione
-
-
?
additional information
?
-
-
CYP17 does not perform side-chain cleavage of cortisol and its metabolites, e.g. 11-oxo-etiocholanolone and 11beta-hydroxyetiocholanolone
-
-
?
additional information
?
-
-
cytochrome P-450 17alpha-hydroxylase-17,20-lyase, CYP17, is a multifunctional enzyme. CYP17 catalyzes at the same active site not only the hydroxylation process but also an acyl-carbon bond cleavage reaction which involves the nucleophilic attack of the ferric-peroxyanion, Fe(III)-O-O-, on the acyl-carbon to furnish a tetrahedral intermediate which fragments, leading to acyl-carbon cleavage
-
-
?
additional information
?
-
-
for the formation of the 16,17-ene steroid, the Fe(III)-O-O- species is trapped by the progestogen, prior to hydroxylation, and the resulting peroxy adduct decomposes to generate a C-17 radical, which is neutralized by a disproportionation reaction involving the loss of C-16-hydrogen atom, mechanism of the acyl-carbon bond cleavage reactions catalysed by CYP17, pathways for the formation of three cleavage products from peroxy adducts, overview
-
-
?
additional information
?
-
CYP17 is unique due to its ability to catalyze two independent reactions in the same active center, the 17alpha-hydroxylase and 17,20-lyase reactions
-
-
?
additional information
?
-
the multifunctional enzyme catalyzes the 17alpha-hydroxylation of DELTA4- and DELTA5-steroids progesterone and pregnenolone to form the corresponding 17alpha-hydroxy products through its hydroxylase activity, and a subsequent 17,20-carbon-carbon scission of pregnene-side chain produce the androgens androstenedione and dehydroepiandrosterone
-
-
?
additional information
?
-
21-trifluorosteroids mht by a substrates for CYP17A1, substrate specificity analysis of CP17A1 with diverse halogenated steroid substrates, e.g. introducing one or more halogen atom to the 17- and 21-positions of progesterone and pregnenolone, 21,21,21-tribromoprogesterone and 21,21,21-trichloroprogesterone, overview. No activity of the recombinant enzyme with 17-fluoroprogesterone and 17-fluoropregnenolone
-
-
?
additional information
?
-
cytochrome P450 17A1 is bifunctional and steroidogenic, it performs both steroid hydroxylation, which is unaffected by cytochrome b5, and an androgen-forming lyase reaction, a 17,20-lyase activity, which occurs via a different catalytic mechanism that is facilitated 10fold by cytochrome b5
-
-
?
additional information
?
-
human CYP17A1 also has progesterone 21-hydroxylase activity, EC 1.14.99.10. Product analysis by LC-MS/MS
-
-
?
additional information
?
-
a minor conformation may yield the minor 16alpha-hydroxyprogesterone metabolite from progesterone
-
-
?
additional information
?
-
-
a minor conformation may yield the minor 16alpha-hydroxyprogesterone metabolite from progesterone
-
-
?
additional information
?
-
the enzyme also shows 17,20-lyase activity which is stimulated by cytochrome b5
-
-
?
additional information
?
-
P450 17A1 is an inherently distributive enzyme but some processivity is present, i.e. some of the 17alpha-hydroxypregnenolone formed from pregnenolone does not dissociate from P450 17A1 before conversion to dehydroepiandrosterone
-
-
?
additional information
?
-
CYP17A1 wild-type and mutation A105L do not hydroxylate pregnenolone in 21- or 16alpha-position
-
-
?
additional information
?
-
-
CYP17A1 wild-type and mutation A105L do not hydroxylate pregnenolone in 21- or 16alpha-position
-
-
?
additional information
?
-
the bifunctional enzyme catalyzes two types of reactions, namely, a 17alpha-hydroxylation reaction and a 17,20-lyase reaction
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
CYP17 existence coincide with that of insulin and demarcated those of glucagon and somatostatin
-
-
?
additional information
?
-
-
the enzyme is involved in androstenedione production
-
-
?
additional information
?
-
-
both hydroxylation and C-C-bond cleavage steps require NADPH and oxygen
-
-
?
additional information
?
-
-
the enzyme catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
?
additional information
?
-
-
the bifunctional enzyme also exhibits 17,20-lyase activity converting 17alpha-hydroxypregnenolone to dehydroepiandrosterone-S, EC 4.1.2.30, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
-
-
-
-
?
7-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
7-dehydro-17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
progesterone + 2 AH2 + 2 O2
androstenedione + acetate + 2 A + 2 H2O
via 17alpha-hydroxyprogesterone
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
-
reaction via 17alpha-hydroxyprogesterone
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2
a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
cytochrome b5 also as cofactor
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
17,20-lyase activity
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
product ratio is 3:1
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
17,20-lyase activity
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
additional information
?
-
-
the enzyme catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
?
additional information
?
-
-
the enzyme catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
catalyzes the last step of androgen biosynthesis in both testes and adrenals
-
-
?
additional information
?
-
-
CYP17 is a key enzyme in steroid hormone biosynthesis
-
-
?
additional information
?
-
-
the enzyme is is essential for the maintenance of normal male and female sexual characteristics, as well as the stress response and mineral balance in all mammals
-
-
?
additional information
?
-
-
the enzyme is required for androgen production, genetic regulation, overview
-
-
?
additional information
?
-
-
CYP17 is the cytochrome b5 modulated key enzyme for the biosynthesis of androgens, catalyzing the 17alpha-hydroxylation of pregnenolone and progesterone and the subsequent cleavage of the C 20,21-acetyl group to yield the corresponding androgens dehydroepiandrosterone and androstendione
-
-
?
additional information
?
-
-
cytochrome P-450 17alpha-hydroxylase-17,20-lyase, CYP17, is a multifunctional enzyme. CYP17 catalyzes at the same active site not only the hydroxylation process but also an acyl-carbon bond cleavage reaction which involves the nucleophilic attack of the ferric-peroxyanion, Fe(III)-O-O-, on the acyl-carbon to furnish a tetrahedral intermediate which fragments, leading to acyl-carbon cleavage
-
-
?
additional information
?
-
CYP17 is unique due to its ability to catalyze two independent reactions in the same active center, the 17alpha-hydroxylase and 17,20-lyase reactions
-
-
?
additional information
?
-
the multifunctional enzyme catalyzes the 17alpha-hydroxylation of DELTA4- and DELTA5-steroids progesterone and pregnenolone to form the corresponding 17alpha-hydroxy products through its hydroxylase activity, and a subsequent 17,20-carbon-carbon scission of pregnene-side chain produce the androgens androstenedione and dehydroepiandrosterone
-
-
?
additional information
?
-
a minor conformation may yield the minor 16alpha-hydroxyprogesterone metabolite from progesterone
-
-
?
additional information
?
-
-
a minor conformation may yield the minor 16alpha-hydroxyprogesterone metabolite from progesterone
-
-
?
additional information
?
-
the enzyme also shows 17,20-lyase activity which is stimulated by cytochrome b5
-
-
?
additional information
?
-
the bifunctional enzyme catalyzes two types of reactions, namely, a 17alpha-hydroxylation reaction and a 17,20-lyase reaction
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
it catalyzes steroid 17alpha-hydroxylase and 17,20-lyase activities in the biosynthesis of androgens, estrogens and cortisol
-
-
?
additional information
?
-
-
CYP17 existence coincide with that of insulin and demarcated those of glucagon and somatostatin
-
-
?
additional information
?
-
-
the enzyme is involved in androstenedione production
-
-
?
additional information
?
-
-
the enzyme catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe3+
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
(-)-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
(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
-
-
(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
(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
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-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
-
21% inhibition at 200 nM and 75% inhibition at 0.002 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-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)phenyl)pentan-3-yl)-1H-imidazole
-
-
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
-
50% inhibition of hydroxylase activity at 0.0165 mM, of 17,20-lyase activity at 0.0028 mM
1-(imidazol-1-ylmethyl)-9-oxo-9H-4-xanthenecarbonitrile
-
at 0.0025 mM 92% inhibition
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-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
-
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-(2-amino-4-thiazolyl)-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)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-hydroxypregnenolone
competitive inhibitor of 17alpha-hydrolase activity
17alpha-Hydroxy-4-androsten-3-one
-
competitive inhibitor of 17alpha-hydroxylation of pregnenolone and of the subsequent C17,20-side chain cleavage reaction
17beta-(cyclopropylamino)-androst-5-en-3beta-ol
-
mechanism-based inhibitor, irreversible inhibition
17beta-hydroxy-17alpha-picolyl-androst-4-en-3-one
-
13% inhibition at 0.05 mM
2'-[[(E)-3-oxoandrost-4-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
1 microM, 54% inhibition
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
1 microM, 78% inhibition
2'-[[(E)-6-oxo-3alpha,5alpha-cycloandrostan-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
compound strongly depresses electrocatalytic activity of CYP17A1 toward pregnenolone at concentrations of 0.1 microM and 1 microM, but data do not obey the Michaelis-Menten catalytic model
2-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzamide
-
39.38% inhibition at 0.01 mM
2-(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-fluoro-4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)phenol hydrobromide
-
-
3,5,4'-trimethylresveratrol
inhibition by is more selective on the 17,20-lyase activity than hydroxylase activity of CYP17A1
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-pyridyl-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene
-
suicide inhibitor
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
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-3-methoxybenzoic acid
-
43.34% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
-
56.23% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(isoxazol-3-yl)benzenesulfonamide
-
81.78% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
-
16.27% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonamide
-
57.1% inhibition at 0.01 mM; 78.84% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonic acid
-
8.37% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzoic acid
-
49.21% inhibition at 0.01 mM
4-(1H-imidazol-1-ylmethyl)-7-[[3-(trifluoromethyl)benzyl]oxy]-2Hchromen-2-one
-
-
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-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-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-pyridylmethyl 1-adamantanecarboxylate
-
at 18 nM 50% C17,20-lyase inhibition, at 43 nM 50% 17alpha-hydroxylase inhibition
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-[(3-chlorophenyl-1H-imidazole-1-yl)methyl]-1H-benzimidazole
-
suicide inhibitor
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-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
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
-
E-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 7% 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
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-[4'-[(1S)-1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]biphenyl-3-yl]acetamide
-
-
transforming growth factor-beta1
-
inhibits 17alpha-hydroxylation in vitro by a noncompetitive mechanism
-
VN/124-1
-
a 17alpha-hydroxylase/17,20 lyase inhibitor, is cytotoxic in prostate cancer cells and synergistically induces endoplasmic reticulum stress, mechanism, overview
Z-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 5% inhibition
(+)-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]-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
-
-
(+)-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)-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-[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
-
-
(+)-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]-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
-
-
(-)-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)-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-[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
-
-
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
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-[1,10-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-(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-chlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0316 mM, of 17,20-lyase activity at 0.00281 mM
1-(4-chlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0298 mM, of 17,20-lyase activity at 0.0049 mM
1-(4-iodobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0110 mM, of 17,20-lyase activity at 0.00158 mM
1-(4-nitrobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0254 mM, of 17,20-lyase activity at 0.0072 mM
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
-
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
-
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
-
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-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
-
at 9 nM 50% inhibition
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-1,2,4-triazol-1-yl)androsta-4,16-dien-3-one
-
at 11 nM 50% inhibition
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
-
at 7 nM 50% inhibition, also potent inhibitor of 5alpha-reductase
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)androsta-5,6-dien-3beta-ol
-
at 2.9 nM 50% inhibition of C17,20-lyase and at 4 nM 50% inhibition of 17alpha-hydroxylase activity
17-(5'-isooxazoloyl)androsta-4,16-dien-3-one
-
type II competitive inhibitor
21-hydroxyiminopregn-4-en-3-one
-
at 0.0003 mM 50% inhibition, also 5alpha-reductase inhibitor
21-hydroxyiminopregn-4-en-3-one
-
at 0.0003 mM 50% inhibition, also 5alpha-reductase inhibitor
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 0.00052 mM 50% inhibition
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
type II competitive inhibitor
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
at 150 nM 94% inhibition
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
at 10 nM 50% inhibition
3beta-hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene
-
at 150 nM 60% inhibition
3beta-hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene
-
at 26 nM 50% inhibition
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
-
type II competitive inhibitor
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
-
at 150 nM 97% inhibition
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
-
at 9 nM 50% inhibition
3beta-hydroxy-23,24-bisnor-5-cholenic-hydroxamic acid
-
at 0.0025 mM 20% inhibition
3beta-hydroxy-23,24-bisnor-5-cholenic-hydroxamic acid
-
at 0.125 mM 19% inhibition
3beta-hydroxy-5-androsten-17beta-hydroxamic acid
-
at 0.125 mM 18% inhibition
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-carboxamide
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
-
-
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]-2,3-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-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
-
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,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,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-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]-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
-
-
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
ketoconazole
-
50% inhibition of hydroxylase activity at 0.00376 mM, of 17,20-lyase activity at 0.00166 mM
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
-
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
-
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
-
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]-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]-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)-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-[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-(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
-
-
additional information
-
not inhibitory: antiepileptic drugs valproic acid, carbamazepine, topiramate, lamotrigine
-
additional information
-
c-fos is an activator protein-1 transcription factor involved in the regulation of CYP17 expression in theca cells, tetradecanoylphorbol acetate increases c-fos 37fold leading to complete suppression of the enzyme, overview
-
additional information
-
synthesis and inhibitory potency of inhibitors, inhibitor molecular modelling studies, ligand binding modes, overview
-
additional information
-
CYP17 inhibitory activities, docking and molecular modelling of inhibitors, overview
-
additional information
-
inhibitor design and synthesis via Suzuki-cross-coupling, Grignard reaction and CDI-assisted SNt-reaction with imidazole, overview
-
additional information
-
inhibition design, synthesis, and molecular modelling, overview
-
additional information
pyridinyl imidazole drugs SB202190 and SB203580 inhibit 17,20 lyase but not 17alpha-hydroxylase activity in human adrenocortical HCI-H295A cells
-
additional information
-
synthesis and inhibitory potency of inhibitors, overview
-
additional information
-
inhibition with anti-P-450 reductase or limitation of NADPH preferentially reduce the lyase activity
-
additional information
-
inhibitory effects of synthesized 3beta-hydroxy-17beta-exo-heterocyclic steroids and the corresponding DELTA4-3-ketosteroids on the testicular C17,20-lyase activity are analyzed by an in vitro radioligand incubation technique, overview
-
additional information
-
synthesis and inhibitory activity of a range of 4-substituted phenylsulfonate derivatives of 4-hydroxybenzyl imidazole against the two components of 17alpha-hydroxylase/17,20-lyase, namely, 17alpha-hydroxylase and 17,20-lyase, overview
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
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
-
phosphatidylcholine
-
incorporation of P450 into liposomal membranes composed of phosphatidylcholine increases activity
cytochrome b5
-
above pH 6.3-6.5 stimulates 17alpha-hydrolase and c17,20-lyase activity
-
cytochrome b5
acts as allosteric facilitator but not as electron donor, increases 17,20-lyase activity
-
cytochrome b5
-
specific stimulation of 17,20-lyase activity of enzyme, up to 10fold increase in lyase activity, while 17alpha-hydroxylase activity is little affected
-
cytochrome b5
-
expression of cytochrome b5 in the zona reticularis, at the onset of adrenarche, increases along with the acyl-carbon bond cleavage activity of CYP17, cytochrome plays a regulatory role for CYP17 activity
-
cytochrome b5
recombinant human microsomal wild-type protein and mutants E48Q, E49Q, and V50S, enzyme interaction analysis by NMR, overview. Substrate-modulated interactions of cytochrome P450 17A1 and cytochrome b5, by reversible binding, involving enzyme anionic residues Glu48 or Glu49 and corresponding cationic CYP17A1 residues Arg347, Arg358, and Arg449. The CYP17A1/b5 interaction is stronger when the hydroxylase substrate pregnenolone is present in the CYP17A1 active site than when the lyase substrate 17alpha-hydroxypregnenolone is in the active site
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additional information
-
cytochrome B5 does not affect the 17alpha-hydroxylase activity
-
additional information
-
cytochrome B5 does not affect the 17alpha-hydroxylase activity
-
additional information
-
not activating: antiepileptic drugs valproic acid, carbamazepine, topiramate, lamotrigine
-
additional information
-
cytochrome B5 does not affect the 17alpha-hydroxylase activity
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
calculation of intramolecular and intermolecular kinetic isotope effects for wild-type and mutant enzymes, overview
-
0.0008
17-hydroxypregnenolone
K89N mutant expressed in Saccharomyces cerevisiae
0.000637
17alpha-hydroxyprogesterone
-
C17,20 lyase activity in female duodenum
0.000675
17alpha-hydroxyprogesterone
-
C17,20 lyase activity in male duodenum
0.0017
pregnenolone
isozyme 1, pH 7.4, temperature not specified in the publication
0.0019
pregnenolone
isozyme 2, pH 7.4, temperature not specified in the publication
0.0016
progesterone
isozyme 1, pH 7.4, temperature not specified in the publication
0.0018
progesterone
isozyme 2, pH 7.4, temperature not specified in the publication
0.0043
progesterone
17alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
0.0053
progesterone
16alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.025
progesterone
16alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
0.17
progesterone
17alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
100
pregnenolone
17alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
4.7
progesterone
16alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
40
progesterone
17alpha-hydroxylation, pH 7.4, 37°C, presence of cytochrome b5
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.005
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
more than 0.005000
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
0.00008
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
0.005
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
0.000099