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Enzyme Nomenclature
Information on EC 1.14.14.19 - steroid 17alpha-monooxygenase
for references in articles please use BRENDA:EC1.14.14.19
Word Map on EC 1.14.14.19
- 1.14.14.19
-
androgen
- adrenal
- progesterone
- testosterone
- steroidogenesis
- androstenedione
- estrogen
- dehydroepiandrosterone
- pregnenolone
- cortisol
- aromatase
- cyp17a1
- testicular
- gonad
-
3beta-hydroxysteroid
-
adrenocortical
- p450scc
-
polycystic
- ketoconazole
- 17-hydroxyprogesterone
- 21-hydroxylase
- dheas
-
mineralocorticoid
-
theca
- p450arom
- hypokalemia
- 17alpha-hydroxyprogesterone
- 17-hydroxypregnenolone
- hyperandrogenism
- abiraterone
- 3beta-hsd
- orteronel
-
amenorrhea
- reticularis
-
delta4
-
acth-stimulated
- hirsutism
- pseudohermaphroditism
- aminoglutethimide
- 11-deoxycorticosterone
- 11-deoxycortisol
-
adrenarche
-
17-hydroxylation
-
17alpha-hydroxylation
- 17alpha-hydroxypregnenolone
- drug development
-
nonsteroidogenic
- analysis
-
c19-steroids
- medicine
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.14.19
-
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RECOMMENDED NAME
GeneOntology No.
steroid 17alpha-monooxygenase
-
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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
BRENDA Link
KEGG Link
MetaCyc Link
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GenBank accession numbers L40335 and AF251388 encodíng isozymes 1 and 2; two isozymes of cytochrome P450 17alpha-hydroxylase/17,20-lyase, that differ in two nucleotides, resulting in variants Ser210Gly and Tyr464Asn
UniProt
-
390115, 390116, 390117, 390118, 390119, 390121, 390122, 390123, 390124, 390125, 390128, 390131, 390132, 390133, 390136, 390137, 390145, 680978, 685308, 686511, 687964, 688979, 692540, 694117, 695150, 701962, 702581, 703542, 703551, 705013, 705509, 714461, 714465, 715857, 716053, 727367, 735281
-
-
-
390120, 716051, 726886, 726923, 726997, 727947, 728213, 733413, 734260, 734283, 734289, 735204, 743986, 744331, 745365, 745649, 746192, 746506
UniProt
recombinant enzyme, expression in Saccharomyces cerevisiae, enzyme catalyzes both 17alpha-hydroxylation and 17,20-lyase reaction which eliminates at C20,21 acetate to yield a C19 steroid
-
-
in addition to 17alphahydroxylase/17,20-lyase activity, enzyme can also act as squalene epoxidase
-
-
-
287096, 390116, 390118, 390119, 390121, 390122, 390126, 390130, 390137, 390147, 5129, 672600, 672605, 688687, 688979, 706778, 714413, 714461, 714465, 732996
-
-
P450c17-I; male fish from an aquatic farm in Yantai City, Shandong, China, gene P450c17-I
B3VLB1
UniProt
P450c17-II; male fish from an aquatic farm in Yantai City, Shandong, China, gene P450c17-II
UniProt
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
malfunction
-
natural mutations causing CYP17A1 deficiency, i.e. 17OHD, a rare form of congenital adrenal hyperplasia
malfunction
-
mutations resulting in only the 17,20-lyase deficiency are located either in the putative substrate-binding region of CYP17A1 or in the region responsible for interaction with cytochrome b5
metabolism
-
CYP17 catalyzes the 17alpha-hydroxylation reaction of delta4-C21 steroids (progesterone derivatives) and delta5-C21 steroids (pregnenolone derivatives) aswell as the 17,20-lyase reaction producing C19-steroids, a key branch point in steroid hormone biosynthesis. Depending on CYP17 activity, the steroid hormone biosynthesis pathway is directed to either the formation of mineralocorticoids and glucocorticoids or sex hormones; CYP17-dependent alternative steroids biosynthesis, overview
metabolism
-
cytochrome P450 CYP17A1 catalyzes a series of reactions that lie at the intersection of corticoid and androgen biosynthesis and thus occupies an essential role in steroid hormone metabolism
metabolism
-
cytochrome b5 plays an important role in the intracellular regulation of biosynthesis of androgens at the level of CYP17. Cytochrome b5 mainly stimulates 17,20-lyase activity of CYP17, but has no effect on the 17alpha-hydroxylation reaction
metabolism
-
the bifunctional enzyme is responsible for pregnenolone C17 hydroxylation, followed by a 17,20-lyase reaction to produce dehydroepiandrosterone, the key intermediate in human synthesis of androgen and estrogen sex steroids
physiological function
-
the enzyme catalyzes two sequential and necessary reactions in the production of androgens
physiological function
17alpha-hydroxylase/17,20-lyase is a critical enzyme in the production of androgens and estrogens in vertebrates
physiological function
cytochromeP450 17alpha-hydroxylase/c17-20 lyase is one of the key enzymes involved in the steroidogenic shift that occurs prior to oocyte maturation in teleosts
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
-
17alpha-hydroxylase/C17,20-lyase, CYP17, a P450 enzyme, is responsible for catalyzing the final step in androgen biosynthesis
physiological function
-
the cytochrome P450 17alpha-hydroxylase/C(17,20)-lyase plays a pivotal role in the synthesis of dehydroepiandrosterone from pregnenolone and progesterone
physiological function
-
CYP17 is involved in endometrial cancinogenesis through apoptosis and invasion pathways. CYP17 affects endometrial carcinoma KLE cell apoptosis by regulating expression of several apoptosis related genes, overview
physiological function
-
cytochrome CYP17 is a key enzyme of steroid hormone biosynthesis. Bifunctional CYP17 catalyzes two independent reactions in the same active center, the 17alpha-hydroxylase and 17,20-lyase reactions
physiological function
B3VLB1;, B6UPD2;
P450c17, a key steroidogenic enzyme, plays important roles in the production of sex steroid and cortisol. In teleost, there are two types of P450c17, P450c17-I possessing 17alpha-hydroxylase and 17,20-lyase activities, and P450c17-II only possessing 17alpha-hydroxylase activity. Only P450c17-II is involved in the production of cortisol in barfin flounder; P450c17, a key steroidogenic enzyme, plays important roles in the production of sex steroid and cortisol. In teleost, there are two types of P450c17, P450c17-I possessing 17alpha-hydroxylase and 17,20-lyase activities, and P450c17-II only possessing 17alpha-hydroxylase activity. P450c17-I is not involved in the production of cortisol in barfin flounder
physiological function
-
the enzyme plays a critical role in the production of androgens and estrogens in vertebrates, important role of P450c17-I during shift in steroidogenesis
physiological function
-
CYP17A1 plays an essential role in the production of steroid androgens by mediating two subsequent steps in the steroidogenic pathway
physiological function
cytochrome P450c17 is a steroidogenic enzyme that catalyzes the steroid 17alpha-hydroxylation needed for glucocorticoid synthesis
physiological function
-
human steroidogenic cytochrome P450 CYP17A1 is required for the biosynthesis of androgens, glucocorticoids, and mineralocorticoids
physiological function
-
the enzyme produces dehydroepiandrosterone, which is the most abundant circulating endogenous sex steroid precursor. Dehydroepiandrosterone plays a key role in e.g. sexual functioning and development
physiological function
-
the enzyme produces dehydroepiandrosterone, which is the most abundant circulating endogenous sex steroid precursor. Dehydroepiandrosterone plays a key role in e.g. sexual functioning and development
physiological function
-
close interactions within living cells between cytochrome P450c17 and cytochrome b5. Residues E48 and E49 residues in cytochrome b5 are essential for activity. The wild type cytochrome b5, but not a mutated, E48G/E49G cyt b5, alters the kinetics of electron transfer between the electrode and the P450c17 during quartz crystal microbalance studies
physiological function
-
the cytochrome P450 17alpha-hydroxylase/C(17,20)-lyase plays a pivotal role in the synthesis of dehydroepiandrosterone from pregnenolone and progesterone
-
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
-
the following factors contribute to the regulation of CYP17 activities: 1. the ratio of NADPH-cytochrome P450 reductase to CYP17, i.e. the rate of delivery of reducing equivalents to the P450, 2. the presence of cytochrome b5 either as an allosteric effector or as an electron donor, 3. phosphorylation of the CYP17 protein, which affects its stability and activity, and 4. retention of the intermediate, 17-OHP5 or 17-OHP4, in the active site of CYP17, which facilitates the 17,20-lyase reaction. Expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries
additional information
CYP17 also exhibits 16alpha-hydroxylase activity towards progesterone in some species, with only human and chimp CYP17 catalysing the biosynthesis of substantial amounts of 16-hydroxy-progesterone. Residue 105 is responsible for the activity, homology modelling, overview
additional information
-
CYP17 also exhibits 16alpha-hydroxylase activity towards progesterone in some species, with only human and chimp CYP17 catalysing the biosynthesis of substantial amounts of 16-hydroxy-progesterone. Residue 105 is responsible for the activity, homology modelling, overview
additional information
CYP17 also exhibits 16alpha-hydroxylase activity towards progesterone in some species, with only human and chimp CYP17 catalysing the biosynthesis of substantial amounts of 16-hydroxy-progesterone. Residue 105 is responsible for the activity, homology modelling, overview
additional information
CYP17 also exhibits 16alpha-hydroxylase activity towards progesterone in some species, with only human and chimp CYP17 catalysing the biosynthesis of substantial amounts of 16-hydroxy-progesterone. Residue 105 is responsible for the activity, homology modelling, overview
additional information
-
in the case of CYP17 the attack of Fe(III)-O-O(-) on the target carbon is promoted by cytochrome b5, which acts as a conformational regulator of CYP17. It is this regulation of CYP17 that provides a safety mechanism which ensures that during corticoid biosynthesis, which involves 17alpha-hydroxylation by CYP17, androgen formation is avoided
additional information
-
knockdown of CYP17 by siRNA affects cellular proliferation
additional information
-
modeling of tertiary structure of CYP17, overview. Direct molecular interactions, with electrostatic interactions playing a crucial role, between steroidogenic enzymes CYP17 and CYP21 that are localized in endoplasmic reticulum membranes of adrenal cortex and involved in biosynthesis of corticosteroid hormones, overview
additional information
-
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, NMR analysis, overview. 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
additional information
-
optimization and standardization of the porcine adrenal cortex microsome assay, overview
additional information
-
CYP17 also exhibits 16alpha-hydroxylase activity towards progesterone in some species, with only human and chimp CYP17 catalysing the biosynthesis of substantial amounts of 16-hydroxy-progesterone. Residue 105 is responsible for the activity, homology modelling, overview
-
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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
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
390123, 390131, 390137, 390145, 657657, 680978, 685308, 686511, 688979, 691232, 704824, 716053, 746506
-
-
?
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
-
-
-
-
?
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
-
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 + 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
-
-
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
?
-
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
?
-
-
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
?
-
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 SUBSTRATES
NATURAL PRODUCTS
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
A6P663
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
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
P05093
-
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
-
-
-
-
?
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
Q29497
-
-
-
?
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 + 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
-
-
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
Q29497
-
-
-
?
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
?
-
P05093
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
?
-
-
the enzyme also shows 17,20-lyase activity which is stimulated by cytochrome b5
-
-
-
additional information
?
-
Q29497
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
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe3+
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INHIBITORS
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
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
0.03