Information on EC 1.14.99.9 - steroid 17alpha-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY
1.14.99.9
-
RECOMMENDED NAME
GeneOntology No.
steroid 17alpha-monooxygenase
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
show the reaction diagram
-
-
-
-
a C21-steroid + [reduced NADPH-hemoprotein reductase] + O2 = a 17alpha-hydroxy-C21-steroid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
the hydroxylation reaction is believed to proceed through a conventional Compound I rebound mechanism. Thr306 is a member of the conserved acid/alcohol pair essential for the efficient delivery of protons required for hydroperoxoanion heterolysis and formation of Compound I in the cytochromes P450. Involvement of a nucleophilic peroxo-anion rather than the traditional Compound I in catalysis. The peroxoanion is required to initiate O-O bond scission and formation of the Cpd I reactive intermediate
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C-C bond cleavage
-
C17-C20 bond cleavage
C-C-bond cleavage
-
-
deacylation
-
-
hydroxylation
-
-
-
-
hydroxylation
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
androgen and estrogen metabolism
-
-
androgen biosynthesis
-
-
glucocorticoid biosynthesis
-
-
Metabolic pathways
-
-
Steroid hormone biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
steroid,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating)
Requires NADPH and EC 1.6.2.4, NADPH---hemoprotein reductase. A microsomal hemeprotein that catalyses two independent reactions at the same active site - the 17alpha-hydroxylation of pregnenolone and progesterone, which is part of glucocorticoid hormones biosynthesis, and the conversion of the 17alpha-hydroxylated products via a 17,20-lyase reaction to form androstenedione and dehydroepiandrosterone, leading to sex hormone biosynthesis (EC 4.1.2.30, 7alpha-hydroxyprogesterone aldolase). The ratio of the 17alpha-hydroxylase and 17,20-lyase activities is an important factor in determining the directions of steroid hormone biosynthesis towards biosynthesis of glucocorticoid or sex hormones.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
17 alpha-hydroxylase/C17,20-lyase
-
-
17-alpha-hydroxylase/C17-20 lyase
-
-
17-hydroxylase/17,20-lyase
-
-
17-hydroxylase/17,20-lyase
P05093
-
17-hydroxylase/C17,20-lyase
-
-
17alphahydroxylase
P05093
-
17alpha-hydroxylase
-
-
17alpha-hydroxylase
-
-
17alpha-hydroxylase
-
-
17alpha-hydroxylase 17,20 lyase
-
-
17alpha-hydroxylase-17,20-lyase
-
-
17alpha-hydroxylase-C(17,20)-lyase
-
-
17alpha-hydroxylase-C17,20 lyase
-
-
-
-
17alpha-hydroxylase-C17,20-lyase
-
-
17alpha-hydroxylase/17,20 lyase
-
-
17alpha-hydroxylase/17,20-lyase
B2D2I4
-
17alpha-hydroxylase/17,20-lyase
-
-
17alpha-hydroxylase/17,20-lyase
P05093
-
17alpha-hydroxylase/17,20-lyase
-
-
17alpha-hydroxylase/C(17,20)-lyase
-
-
17alpha-lyase
-
-
17alpha-OHase
-
-
17alpha-OHase
-
-
17OHD
-
-
CYP 17
-
-
CYP17
A6P663
-
CYP17
-
gene name
CYP17
Q29497
-
CYP17A1
B2D2I4
gene name
CYP17A1
P05093
; isoform
CYPXVII
-
-
-
-
cytochrome P-450 (P45017alpha,lyase)
-
-
-
-
cytochrome P-45017alpha
-
-
cytochrome P450 17
-
gene name
cytochrome P450 17
P05093
-
cytochrome P450 17
-
-
cytochrome P450 17A1
P05093
-
cytochrome P450 17alpha-hydroxylase
-
-
cytochrome P450 17alpha-hydroxylase-17,20-lyase
-
-
cytochrome P450 17alpha-hydroxylase/17,20 lyase
A5HEW0
-
cytochrome P450 17alpha-hydroxylase/17,20 lyase
Capra hircus South African angora
A5HEW0
-
-
cytochrome P450 17alpha-hydroxylase/17,20 lyase
P05093
-
cytochrome P450 17alpha-hydroxylase/17,20 lyase
Q9GLD2
-
cytochrome P450 17alpha-hydroxylase/17,20 lyase
P19100
-
cytochrome P450 17alpha-hydroxylase/17,20-lyase
-
-
cytochrome P450 17alpha-hydroxylase/17,20-lyase
Q29497
-
cytochrome p450 17alpha-hydroxylase/C(17,20)-lyase
-
-
cytochrome p450 17alpha-hydroxylase/C(17,20)-lyase
Rattus norvegicus Wistar
-
-
-
cytochrome P450 17alpha-hydroxylase/C17,20-lyase
-
-
cytochrome P450 17alpha-hydroxylase/c17-20 lyase
C7B608
-
cytochrome P45017alpha
-
-
-
-
cytochrome P45017alpha
-
-
cytochrome P450c17
-
-
cytochrome P450c17
P05093
-
cytochrome P450c17
-
-
cytochrome P450c17
-
-
cytochrome P450c17alpha
-
-
cytochromeP450 17alpha-hydroxylase/C17-20 lyase
A6P663
-
EC 1.14.1.7
-
-
formerly
-
EC 1.99.1.9
-
-
formerly
-
P450 17
-
-
P450(17alpha)
-
-
P450-17alpha
-
-
P450-C17
-
-
-
-
P45017alpha
-
-
P45017alpha
-
-
P450c17
C7B608
-
P450c17
A6P663
-
P450c17
P05093
-
P450c17
Rattus norvegicus Wistar
-
-
-
P450c17
-
-
P450c17
B3VLB1, B6UPD2
-
P450c17-I
B2D2I4
-
Steroid 17-alpha-hydroxylase/17,20 lyase
-
-
-
-
steroid 17alpha-hydroxylase
-
-
-
-
steroid 17alpha-hydroxylase
-
-
steroid 17alphahydroxylase/17,20-lyase
P05093
-
CAS REGISTRY NUMBER
COMMENTARY
9029-67-8
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Capra hircus South African angora
-
UniProt
Manually annotated by BRENDA team
air-breathing catfish, gene p450c17
SwissProt
Manually annotated by BRENDA team
gene CYP17A1
UniProt
Manually annotated by BRENDA team
; CYP17A1; CYP17A1
UniProt
Manually annotated by BRENDA team
; gene CYP17
-
-
Manually annotated by BRENDA team
bifunctional 17alpha-hydroxylase and 17,20-lyase in steroid biosynthesis
-
-
Manually annotated by BRENDA team
female patient with a malignant mixed germ cell tumor
-
-
Manually annotated by BRENDA team
female patient with enzyme deficiency
-
-
Manually annotated by BRENDA team
gene CYP17
-
-
Manually annotated by BRENDA team
gene CYP17A1
-
-
Manually annotated by BRENDA team
gene CYP17A1
UniProt
Manually annotated by BRENDA team
recombinant enzyme
-
-
Manually annotated by BRENDA team
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
-
-
Manually annotated by BRENDA team
cynomolgus monkey
-
-
Manually annotated by BRENDA team
in addition to 17alphahydroxylase/17,20-lyase activity, enzyme can also act as squalene epoxidase
-
-
Manually annotated by BRENDA team
GenBank accession numbers L40335 and AF251388 encodng isozymes 1 and 2; two isozymes of cytochrome P450 17alpha-hydroxylase/17,20-lyase, that differ in two nucleotides, resulting in variants Ser210Gly and Tyr464Asn
UniProt
Manually annotated by BRENDA team
; male frogs
-
-
Manually annotated by BRENDA team
female Sprague-Dawley rats, gene CYP17
-
-
Manually annotated by BRENDA team
male sprague-dawley rats
-
-
Manually annotated by BRENDA team
Wistar rats
-
-
Manually annotated by BRENDA team
Rattus norvegicus Wistar
male
-
-
Manually annotated by BRENDA team
from Shandong coastal area, genes P450c17-I and P450c17-II
-
-
Manually annotated by BRENDA team
P450c17-I; male fish from an aquatic farm in Yantai City, Shandong, China, gene P450c17-I
UniProt
Manually annotated by BRENDA team
P450c17-II; male fish from an aquatic farm in Yantai City, Shandong, China, gene P450c17-II
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
-
the CYP17 enzymes from various species have 46-98% sequence homology, depending on the evolutionary distance between the organisms. Enzymes from different mammalian species show relatively high homology of amino acid sequences, but have different types of activity and different requirements for cytochrome b5
evolution
P05093
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
P05093
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
malfunction
-
deficiency of CYP17A1 causes hypertension
metabolism
-
CYP17 catalyzes the last step in androgen biosynthesis
metabolism
-
Cyp17 is important in the metabolism of androgens, overview
metabolism
-
CYP17 is the key enzyme for the biosynthesis of androgens
metabolism
-
CYP17 is the key enzyme in androgen biosynthesis pathway
metabolism
-
the enzyme is important in adrogene biosynthesis
metabolism
P05093
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
metabolism
P05093
CYP17-dependent alternative steroids biosynthesis, overview
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
physiological function
C7B608
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
-
the enzyme catalyzes two sequential and necessary reactions in the production of androgens
physiological function
B2D2I4
17alpha-hydroxylase/17,20-lyase is a critical enzyme in the production of androgens and estrogens in vertebrates
physiological function
-
17alpha-hydroxylase/C17,20-lyase, CYP17, a P450 enzyme, is responsible for catalyzing the final step in androgen biosynthesis
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
-
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
physiological function
P05093
CYP17A1 catalyzes the 17alpha-hydroxylase and 17,20-lyase reactions using various C21-steroids as substrates, overview
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
-
CYP17A1 plays an essential role in the production of steroid androgens by mediating two subsequent steps in the steroidogenic pathway
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
P05093
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
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
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. 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
-
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
Rattus norvegicus Wistar
-
the cytochrome P450 17alpha-hydroxylase/C(17,20)-lyase plays a pivotal role in the synthesis of dehydroepiandrosterone from pregnenolone and progesterone
-
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
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
Q9GLD2
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
P19100
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
A5HEW0
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
-
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
P05093
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
-
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
-
optimization and standardization of the porcine adrenal cortex microsome assay, 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
Capra hircus South African angora
-
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
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
17-hydroxyprogesterone + NADPH + H+ + O2
androstenedione + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxypregnenolone + AH2 + O2
dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxypregnenolone + AH2 + O2
dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
P05093
-
-
-
?
17alpha-hydroxypregnenolone + AH2 + O2
?
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + AH2 + O2
?
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + AH2 + O2
?
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + AH2 + O2
dehydroepiandrosterone + androstenedione + A + H2O
show the reaction diagram
-
-
-
-
?
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-3,20-dione + NADPH + O2
5alpha-pregnan-17alpha-ol-3,20-dione + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
5alpha-pregnan-3alpha-ol-20-one + NADPH + O2
5alpha-pregnan-3alpha,17alpha-diol-20-one + ?
show the reaction diagram
-
-
-
-
?
7,12-dimethylbenz[a]anthracene + AH2 + O2
?
show the reaction diagram
P05093
substrate for CYP17A1
-
-
?
7-dehydro-17alpha-hydroxypregnenolone + AH2 + O2
7-dehydro-dehydroepiandrosterone + A + H2O
show the reaction diagram
-
-
-
-
?
7-dehydro-17alpha-hydroxypregnenolone + AH2 + O2
7-dehydro-dehydroepiandrosterone + A + H2O
show the reaction diagram
P05093
low activity
-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxy-pregnenolone + A + H2O
show the reaction diagram
P05093
-
-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
P05093
-
-
-
?
7-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
7-dehydro-17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
P05093
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A2 + H2O
show the reaction diagram
-
i.e. pregn-5-en-3beta-ol-20-one
-
-
?
pregnenolone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
Q64410
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
P05093
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
cytochrome b5 also as cofactor
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
17,20-lyase activity
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
Q29497
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
via Compound I intermediate
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
via the catalytic cycle involving an iron(IV) oxo intermediate
-
-
?
pregnenolone + [reduced NADPH.hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + 2 AH2 + 2 O2
androstenedione + acetate + 2 A + 2 H2O
show the reaction diagram
A6P663
via 17alpha-hydroxyprogesterone
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
show the reaction diagram
C7B608
-
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
show the reaction diagram
-
reaction via 17alpha-hydroxyprogesterone
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
P05093
-
-
-
?
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + H+ + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
Q64410
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
17,20-lyase activity
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
-
-
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
P05093
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
product ratio is 3:1
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
Q29497
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
via Compound I intermediate
-
-
?
aflatoxin B1 + AH2 + O2
aflatoxin B1epoxide + A + H2O
show the reaction diagram
P05093
substrate for CYP17A1
-
-
?
additional information
?
-
P05093
both the lyase and hydroxylase activities proceed from a common steroid-binding geometry by an iron oxene mechanism, 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
?
-
Q64410
enzyme effectively catalyzes hydroxylation reaction for both progesterone and pregnenolone, with 17alpha-hydroxyprogesterone, also 17,20-lyase activity is realized
-
-
-
additional information
?
-
-
CYP17 is a key enzyme in steroid hormone biosynthesis
-
-
-
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 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 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 existence coincide with that of insulin and demarcated those of glucagon and somatostatin
-
-
-
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
?
-
-
the enzyme is involved in androstenedione production
-
-
-
additional information
?
-
-
CYP17 does not perform side-chain cleavage of cortisol and its metabolites, e.g. 11-oxo-etiocholanolone and 11beta-hydroxyetiocholanolone
-
-
-
additional information
?
-
C7B608
P450c17 is an enzyme type that lacks lyase activity
-
-
-
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
?
-
-
substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the baboon enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the bison enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the bovine enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the cat enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the chimp enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the goat enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the guinea pig enzyme belongs to the DELTA4-type CYP17, which has no, or very low, 17,20-lyase activity with 17alpha-hydroxy-pregnenolone with the formation of dehydroepiandrosterone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the horse enzyme belongs to the DELTA4,5-type of CYP17, which catalyses the 17alpha-hydroxylation of progesterone and pregnenolone and the 17,20-lyase reaction of 17alpha-hydroxy-progesterone and 17alpha-hydroxy-pregnenolone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
P05093
the human enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the pig enzyme belongs to the DELTA4,5-type of CYP17, which catalyses the 17alpha-hydroxylation of progesterone and pregnenolone and the 17,20-lyase reaction of 17alpha-hydroxy-progesterone and 17alpha-hydroxy-pregnenolone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the rat enzyme belongs to the DELTA4,5-type of CYP17, which catalyses the 17alpha-hydroxylation of progesterone and pregnenolone and the 17,20-lyase reaction of 17alpha-hydroxy-progesterone and 17alpha-hydroxy-pregnenolone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the sheep enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
both hydroxylation and C-C-bond cleavage steps require NADPH and oxygen
-
-
-
additional information
?
-
P05093
CYP17 has both 17alpha-hydroxylase and 17,20-lyase activities
-
-
-
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
?
-
P05093
no activity with 17alpha-hydroxyprogesterone
-
-
-
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
?
-
Q29497
the bifunctional enzyme catalyzes two types of reactions, namely, a 17alpha-hydroxylation reaction and a 17,20-lyase reaction
-
-
-
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
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
17alpha-hydroxypregnenolone + AH2 + O2
dehydroepiandrosterone + acetate + A + H2O
show the reaction diagram
-
-
-
-
?
2 progesterone + 2 AH2 + 2 O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + 2 A + 2 H2O
show the reaction diagram
-
-
-
-
?
7-dehydro-17alpha-hydroxypregnenolone + AH2 + O2
7-dehydro-dehydroepiandrosterone + A + H2O
show the reaction diagram
-
-
-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxy-pregnenolone + A + H2O
show the reaction diagram
P05093
-
-
-
?
7-dehydro-pregnenolone + AH2 + O2
7-dehydro-17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + AH2 + O2
17alpha-hydroxypregnenolone + A2 + H2O
show the reaction diagram
-
i.e. pregn-5-en-3beta-ol-20-one
-
-
?
pregnenolone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
P05093
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield dehydroepiandrosterone
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
-
cytochrome b5 also as cofactor
?
pregnenolone + NADPH + O2
17alpha-hydroxypregnenolone + NADP+ + H2O
show the reaction diagram
-
17,20-lyase activity
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
pregnenolone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
Q29497
-
-
-
?
progesterone + 2 AH2 + 2 O2
androstenedione + acetate + 2 A + 2 H2O
show the reaction diagram
A6P663
via 17alpha-hydroxyprogesterone
-
-
?
progesterone + 2 NADPH + 2 H+ + 2 O2
androstenedione + acetate + 2 NADP+ + 2 H2O
show the reaction diagram
-
reaction via 17alpha-hydroxyprogesterone
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + AH2 + O2
17alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
P05093
-
-
-
?
progesterone + ferrocytochrome b5 + O2
?
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + H+ + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
-
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
product eliminates at C20,21 acetate to yield androstenedione
?
progesterone + NADPH + O2
17alpha-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
17,20-lyase activity
-
-
?
progesterone + reduced acceptor + O2
17alpha-hydroxyprogesterone + acceptor + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + 16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
product ratio is 3:1
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
17alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
Q29497
-
-
-
?
7-dehydropregnenolone + [reduced NADPH-hemoprotein reductase] + O2
7-dehydro-17alpha-hydroxypregnenolone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
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 catalyzes the key branch point in the metabolic conversion of cholesterol either to androgens and estrogens, or to glucocorticoids
-
-
-
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 existence coincide with that of insulin and demarcated those of glucagon and somatostatin
-
-
-
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
?
-
-
the enzyme is involved in androstenedione production
-
-
-
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
?
-
-
substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the baboon enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the bison enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the bovine enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the cat enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the chimp enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the goat enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the guinea pig enzyme belongs to the DELTA4-type CYP17, which has no, or very low, 17,20-lyase activity with 17alpha-hydroxy-pregnenolone with the formation of dehydroepiandrosterone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the horse enzyme belongs to the DELTA4,5-type of CYP17, which catalyses the 17alpha-hydroxylation of progesterone and pregnenolone and the 17,20-lyase reaction of 17alpha-hydroxy-progesterone and 17alpha-hydroxy-pregnenolone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
P05093
the human enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, overview
-
-
-
additional information
?
-
-
the pig enzyme belongs to the DELTA4,5-type of CYP17, which catalyses the 17alpha-hydroxylation of progesterone and pregnenolone and the 17,20-lyase reaction of 17alpha-hydroxy-progesterone and 17alpha-hydroxy-pregnenolone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the rat enzyme belongs to the DELTA4,5-type of CYP17, which catalyses the 17alpha-hydroxylation of progesterone and pregnenolone and the 17,20-lyase reaction of 17alpha-hydroxy-progesterone and 17alpha-hydroxy-pregnenolone, substrate specificity, comparison of different species, overview
-
-
-
additional information
?
-
-
the sheep enzyme belongs to the DELTA5-type CYP17, which has no, or very low, 17,20-lyase activity with 17-OH-progesterone with the formation of androstendione, substrate specificity, comparison of different species, none of the primate enzymes has 17,20-lyase activity towards DELTA4-steroids, 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
?
-
Q29497
the bifunctional enzyme catalyzes two types of reactions, namely, a 17alpha-hydroxylation reaction and a 17,20-lyase reaction
-
-
-
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
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome b5
P05093
without effect on steroid 17alpha-hydroxylation, cytochrome b5 causes a 5-10fold stimulation of the 17,20-lyase reaction mediated by CYP17
-
cytochrome b5
-
-
-
cytochrome b5
-
-
-
cytochrome P450
-
-
-
ferrocytochrome b5
-
-
heme
-
computer model of the tertiary structure of the hemeprotein
NADPH
-
dependent on
NADPH
C7B608
-
NADPH
-
required
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe3+
-
-
Fe3+
-
heme
Fe3+
-
heme content more than 0.8 nM/nM protein
Fe3+
-
11.1 nM heme per mg protein
Fe3+
-
8 nM per mg protein
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
-
-
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
-
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
-
(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
-
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
-
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
-
-
(4-(benzo[b]thiophen-5-yl)phenyl)methanol
-
2% inhibition at 200 nM and 39% inhibition at 0.002 mM
(5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
-
(5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
-
(5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
-
(5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
-
(5'R)-17beta-[2-(4-fluorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
-
(5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
-
(S)-(-)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate
-
at 1.8 nM 50% C17,20-lyase inhibition, at 3.3 nM 50% 17alpha-hydroxylase inhibition
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
-
1-((4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-methyl)-1H-imidazole
-
19% inhibition at 200 nM and 74% inhibition at 0.002 mM
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
-
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
-
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
-
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
-
21% inhibition at 200 nM and 75% inhibition at 0.002 mM
1-(1-(4-(naphthalen-2-yl)phenyl)propyl)-1H-imidazole
-
-
1-(1-(4-thiophen-3-yl-phenyl)ethyl)-1H-imidazole
-
-
1-(1-(4-thiophen-3-yl-phenyl)propyl)-1H-imidazole
-
-
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
-
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
1-(1-[4-[5-(methylsulfanyl)thiophen-2-yl]phenyl]propyl)-1H-imidazole
-
-
1-(10-phenyl-decyl)-1H-imidazole
-
65.2% inhibition at 0.01 mM
1-(10-phenyldecyl)-1H-1,2,4-triazole
-
79.6% inhibition at 0.1 mM
1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
-
-
1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
-
-
1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
-
-
1-(1H-imidazol-5-yl)-2-methyl-1-(4-thiophen-3-ylphenyl)propan-1-ol
-
-
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
-
1-(2-phenyl-ethyl)-1H-imidazole
-
10.6% inhibition at 0.01 mM
1-(2-phenylethyl)-1H-1,2,4-triazole
-
10.9% inhibition at 0.1 mM
1-(3,4-dichlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0122 mM, of 17,20-lyase activity at 0.0021 mM
1-(3,5-dibromobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0259 mM, of 17,20-lyase activity at 0.00316 mM
1-(3,5-dichlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0226 mM, of 17,20-lyase activity at 0.0033 mM
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
-
1-(3-(4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)phenyl)pentan-3-yl)-1H-imidazole
-
-
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(3-phenyl-propyl)-1H-imidazole
-
23.4% inhibition at 0.01 mM
1-(3-phenylpropyl)-1H-1,2,4-triazole
-
17.2% inhibition at 0.1 mM
1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-(4-(6-methoxynaphthalen-2-yl)phenyl)propan-1-ol
-
7% inhibition at 200 nM and 43% inhibition at 0.002 mM
1-(4-(benzofuran-5-yl)benzyl)-1H-imidazole
-
no inhibition at 200 nM and 21% inhibition at 0.002 mM
1-(4-bromobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0165 mM, of 17,20-lyase activity at 0.0028 mM
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-chlorobenzyl)-1H-imidazole
-
-
1-(4-fluorobenzyl)-1H-imidazole
-
-
1-(4-furan-3-ylbenzyl)-1H-imidazole
-
-
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-iodobenzyl)-1H-imidazole
-
-
1-(4-methylbenzyl)-1H-imidazole
-
-
1-(4-nitrobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0254 mM, of 17,20-lyase activity at 0.0072 mM
1-(4-nitrobenzyl)-1H-imidazole
-
-
1-(4-phenyl-butyl)-1H-imidazole
-
40.7% inhibition at 0.01 mM
1-(4-phenylbutyl)-1H-1,2,4-triazole
-
29% inhibition at 0.1 mM
1-(5-phenyl-pentyl)-1H-imidazole
-
59.7% inhibition at 0.01 mM
1-(5-phenylpentyl)-1H-1,2,4-triazole
-
55% inhibition at 0.1 mM
1-(6-phenyl-hexyl)-1H-imidazole
-
61.3% inhibition at 0.01 mM
1-(6-phenylhexyl)-1H-1,2,4-triazole
-
60.4% inhibition at 0.1 mM
1-(7-phenyl-heptyl)-1H-imidazole
-
67.5% inhibition at 0.01 mM
1-(7-phenylheptyl)-1H-1,2,4-triazole
-
73.2% inhibition at 0.1 mM
1-(8-phenyl-octyl)-1H-imidazole
-
70.2% inhibition at 0.01 mM
1-(8-phenyloctyl)-1H-1,2,4-triazole
-
76.6% inhibition at 0.1 mM
1-(9-phenyl-nonyl)-1H-imidazole
-
64.5% inhibition at 0.01 mM
1-(9-phenylnonyl)-1H-1,2,4-triazole
-
79.1% inhibition at 0.1 mM
1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
1-(imidazol-1-ylmethyl)-4-bromo-9H-9-xanthenone
-
at 0.0025 mM 98% inhibition
1-(imidazol-1-ylmethyl)-4-nitro-9H-9-xanthenone
-
at 0.0025 mM 94% inhibition
1-(imidazol-1-ylmethyl)-9-oxo-9H-4-xanthenecarbonitrile
-
at 0.0025 mM 92% inhibition
1-benzyl-1H-1,2,4-triazole
-
6.8% inhibition at 0.1 mM
1-benzyl-1H-imidazole
-
13.5% inhibition at 0.01 mM
1-benzyl-1H-imidazole
-
-
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
-
1-[(4-phenylthiophen-2-yl)methyl]-1H-imidazole
-
-
1-[(5,7-dibromobenzofuran-2-yl)methyl]imidazole
-
at 1150 nM 50% inhibition
1-[(5,7-dibromobenzofuran-2-yl)methyl]imidazole
-
at 185 nM 50% inhibition
1-[(5,7-dichlorobenzofuran-2-yl)methyl]imidazole
-
at 1300 nM 50% inhibition
1-[(5,7-dichlorobenzofuran-2-yl)methyl]imidazole
-
at 180 nM 50% inhibition
1-[(5-bromobenzofuran-2-yl)methyl]imidazole
-
at 1540 nM 50% inhibition
1-[(5-bromobenzofuran-2-yl)methyl]imidazole
-
at 380 nM 50% inhibition
1-[(5-chlorobenzofuran-2-yl)methyl]imidazole
-
at 1800 nM 50% inhibition
1-[(5-chlorobenzofuran-2-yl)methyl]imidazole
-
at 230 nM 50% inhibition
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-[1,1'-biphenyl]-4-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
-
1-[1-(3',4'-dimethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(3'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
-
1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-ethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
-
1-[1-(4'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
-
1-[1-(4'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4-thiophen-3-ylphenyl)ethyl]-1H-imidazole
-
-
1-[1-(4-thiophen-3-ylphenyl)propyl]-1H-imidazole
-
-
1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
-
-
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
-
1-[1-[2-fluoro-4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[1-[4-(2-chlorothiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[1-[4-(3,4-difluorophenyl)thiophen-2-yl]propyl]-1H-imidazole
-
-
1-[1-[4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[3-(4-bromophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.00295 mM, of 17,20-lyase activity at 0.00033 mM
1-[3-(4-chlorophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0058 mM, of 17,20-lyase activity at 0.00055 mM
1-[3-(4-fluorophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.02781 mM, of 17,20-lyase activity at 0.00196 mM
1-[4-(1H-imidazol-1-ylmethyl)phenyl]methanimine
-
-
1-[4-(4-methylthiophen-3-yl)benzyl]-1H-imidazole
-
-
1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
-
1-[4-[5-(methylsulfanyl)thiophen-2-yl]benzyl]-1H-imidazole
-
-
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
-
1-[[4-(3,4-difluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(3,4-dimethoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(3-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(4-fluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(4-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
17-(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
-
-
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
-
at 7 nM 50% inhibition, also potent inhibitor of 5alpha-reductase
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
-
at 8 nM 50% inhibition
17-(2-amino-4-thiazolyl)-androsta-5,16-dien-3beta-ol
-
type II competitive inhibitor
17-(3'-pyrazolyl)androsta-4,16-dien-3beta-one
-
type II competitive inhibitor
17-(3'-pyrazolyl)androsta-5,16-dien-3beta-ol
-
type II competitive inhibitor
17-(3-pyridyl)-5alpha-androst-16-en-3-one
-
at 3 nM 50% inhibition of C17,20-lyase and at 4.7 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-5alpha-androst-16-en-3alpha-ol
-
at 2.5 nM 50% inhibition of C17,20-lyase and at 4.3 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-androst-5-en-3beta-ol
-
at 23 nM 50% inhibition of C17,20-lyase and at 47 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-androsta-4,16-dien-3,11-dione
-
at 2.9 nM 50% inhibition of C17,20-lyase and at 13 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-3,5,16-triene
-
at 5.6 nM 50% inhibition of C17,20-lyase and at 12.5 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-4,16-dien-3-one
-
at 2.1 nM 50% inhibition of C17,20-lyase and at 2.8 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-5,6-dien-3beta-ol
-
-
17-(3-pyridyl)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-(3-pyridyl)estra-1,3,5[10],16-tetraen-3-ol
-
at 1.8 nM 50% inhibition of C17,20-lyase and at 2.6 nM 50% inhibition of 17alpha-hydroxylase activity
17-(5'-isooxazoloyl)androsta-4,16-dien-3-one
-
type II competitive inhibitor
17-(methylthio)androst-5-en-3beta-ol S-oxide
-
type I competitive inhibitor
17-hydroxypregnenolone
-
competitive inhibitor of 17alpha-hydrolase activity
17alpha-Hydroxy-4-androsten-3-one
-
competitive inhibitor of 17alpha-hydroxylation of pregnenolone and of the subsequent C17,20-side chain cleavage reaction
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-tolyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-tolylphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolylphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-phenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-phenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(2-oxazolidon-5-yl)-androst-4-en-3-one
-
-
17beta-(2-oxazolidon-5-yl)androst-5-en-3beta-ol
-
-
17beta-(cyclopropylamino)-androst-5-en-3beta-ol
-
mechanism-based inhibitor, irreversible inhibition
17beta-acetamidoandrost-4-en-3-one
-
-
17beta-ureidoandrosta-1,4-dien-3-one
-
-
17beta-[3-(N-3,5-dimethylphenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-3,5-dimethylphenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-bromophenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-bromophenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-chlorophenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-chlorophenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-fluorophenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-fluorophenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-4-methoxyphenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-4-methoxyphenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
17beta-[3-(N-phenyl)-2-oxazolidon-5-yl]androst-4-en-3-one
-
-
17beta-[3-(N-phenyl)-2-oxazolidon-5-yl]androst-5-en-3beta-ol
-
-
19-azido-androstenedione
-
-
19-thiomethyl-androstenedione
-
-
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
-
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
-
2-(1H-imidazol-4-ylmethyl)-9H-carbazole
-
suicide inhibitor
2-(4-pyridyl)propan-2-yl 1-adamantanecarboxylate
-
at 2.7 nM 50% C17,20-lyase inhibition, at 8.8 nM 50% 17alpha-hydroxylase inhibition
2-(chloromethyl)-5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
2-fluoro-4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)phenol hydrobromide
-
-
2-fluoro-4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)phenol hydrobromide
-
-
2-fluoro-4-[5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]phenol
-
-
2-fluoro-4-[5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl]phenol
-
-
2-fluoro-5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
20(S)-20,21-aziridinylpregn-5-en-3beta-ol
-
type II competitive inhibitor
20-hydroxyiminopregna-4,14,16-trien-3-one
-
at 0.0002 mM 50% inhibition
20-hydroxyiminopregna-4,16-dien-3-one
-
at 0.0001 mM 50% inhibition
20-hydroxyiminopregna-5,14,16-trien-3beta-ol
-
at 0.0002 mM 50% inhibition
20-hydroxyiminopregna-5,16-dien-3beta-ol
-
at 0.00017 mM 50% inhibition
20xi-hydroxy-21-trifluoropregn-4-en-3-one
-
type I competitive inhibitor
20xi-hydroxy-21-trifluoropregn-4-en-3-one
-
at 0.0006 mM 50% inhibition
21-hydroxyimino-21-methylpregn-4-en-3-one
-
at 0.0036 mM 50% inhibition
21-hydroxyiminopregn-4-en-3-one
-
at 0.0003 mM 50% inhibition, also 5alpha-reductase inhibitor
21-hydroxyiminopregn-5-en-3beta-ol
-
at 0.00027 mM 50% inhibition
21-hydroxyiminopregn-5-en-3beta-ol
-
at 0.00276 mM 50% inhibition
21-hydroxyiminopregna-4,17(20)-dien-3-one
-
at 0.00018 mM 50% inhibition, also 5alpha-reductase inhibitor
21-hydroxyiminopregna-4,17(20)-dien-3-one
-
at 0.00014 mM 50% inhibition
21-hydroxyiminopregna-5,17(29)-dien-3beta-ol
-
at 0.000077 mM 50% inhibition
21-hydroxyiminopregna-5,17(29)-dien-3beta-ol
-
at 0.00052 mM 50% inhibition
21-methylpregn-5-en-3beta-ol-21-one
-
at 0.0098 mM 50% inhibition
21-trifluoropregn-4-en-3,20-dione
-
at 0.0021 mM 50% inhibition
21-trifluoropregn-5-en-3beta,20xi-diol
-
at 0.0044 mM 50% inhibition
22-Amino-23,24-bisnor-5-cholen-3beta-ol
-
type II competitive inhibitor
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
-
3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
3-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
3-(6-Chloro-3-methyl-2-indenyl)pyridine
-
competitive inhibitor
3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3-pyridyl-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene
-
suicide inhibitor
3-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
3-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
3-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
3beta-acetoxy-17-(3-pyridyl)androsta-5,16-diene
-
at 17 nM 50% inhibition of C17,20-lyase and at 18 nM 50% inhibition of 17alpha-hydroxylase activity
3beta-acetoxy-21-chloropregn-5-ene-20beta-N-phenylurethane
-
-
3beta-acetoxy-5alpha,6beta,17alpha,21-tetrabromo-pregnane-20-one
-
-
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
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 0.0025 mM 17% inhibition
3beta-hydroxy-5-androsten-17beta-hydroxamic acid
-
at 0.125 mM 18% inhibition
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
-
4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
-
-
4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
-
-
4-(1H-imidazol-1-ylmethyl)-7-[(3-methylbenzyl)oxy]-2H-chromen-2-one
-
-
4-(1H-imidazol-1-ylmethyl)-7-[[3-(trifluoromethyl)benzyl]oxy]-2Hchromen-2-one
-
-
4-(1H-imidazol-1-ylmethyl)phenol
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-methylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl benzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
-
-
4-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(4-methoxyphenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
4-(6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(8-(1-(1H-imidazol-1-yl)propyl)quinolin-5-yl)phenol
-
17% inhibition at 200 nM and 71% inhibition at 0.002 mM
4-(benzo[b]thiophen-5-yl)benzaldehyde
-
7% inhibition at 200 nM and 40% inhibition at 0.002 mM
4-amino-17beta-(cyclopropylamino)-androst-4-en-3-one
-
suicide inhibitor
4-amino-17beta-(cyclopropyloxy)-androst-4,6-dien-3-one
-
suicide inhibitor
4-amino-17beta-(cyclopropyloxy)-androst-4-en-3-one
-
suicide inhibitor
4-chloro-3,4-dihydro-2-(3-pyridyl)-1-(2H)-naphthalenone
-
competitive inhibitor
4-hydroxybenzyl imidazole
-
-
4-hydroxybenzyl imidazole
-
-
4-iodobenzyl imidazole
-
-
4-pyridylmethyl 1-adamantanecarboxylate
-
at 18 nM 50% C17,20-lyase inhibition, at 43 nM 50% 17alpha-hydroxylase inhibition
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
-
4-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]morpholine
-
-
4-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
4-[5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]benzene-1,2-diol
-
-
4-[5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl]benzene-1,2-diol
-
-
4-[6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]pyridine
-
-
4-[6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-methoxyphenyl)-1H-inden-3-yl]pyridine
-
-
5-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-(1-(1H-imidazol-1-yl)propyl)phenyl)-1H-indole
-
5% inhibition at 200 nM and 27% inhibition at 0.002 mM
5-(4-(1H-imidazol-1-ylmethyl)phenyl)-1H-indole
-
5% inhibition at 200 nM and 39% inhibition at 0.002 mM
5-(4-fluorophenyl)-1-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-fluorophenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-[(3-chlorophenyl-1H-imidazole-1-yl)methyl]-1H-benzimidazole
-
suicide inhibitor
5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyrimidine
-
-
6-(3,4-difluorophenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3,4-difluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(4-(1H-imidazol-1-ylmethyl)phenyl)benzo[d]thiazole
-
no inhibition at 200 nM and 17% inhibition at 0.002 mM
6-(4-(3-(1H-imidazol-1-yl)pentan-3-yl)phenyl)naphthalen-2-ol
-
16% inhibition at 200 nM and 74% inhibition at 0.002 mM
6-(4-fluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
-
-
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
-
7-[(3-chlorobenzyl)oxy]-4-(1H-imidazol-1-ylmethyl)-2H-chromen-2-one
-
-
7-[(3-fluorobenzyl)oxy]-4-(1H-imidazol-1-ylmethyl)-2H-chromen-2-one
-
-
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
-
abiraterone
-
-
abiraterone
-
i.e. 17-(3-pyridyl)androsta-5,16-dien-3beta-ol
abiraterone acetate
-
-
abiraterone acetate
-
-
benzyl imidazole
-
-
bitertanol
P05093
-
cyclopregnenolone
-
i.e. 3alpha5-cyclo-6beta-methoxy-5alpha-pregnane-20-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
-
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
-
diethylstilbestrol
-
-
dioctyltin chloride
-
-
-
E-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 7% inhibition
Emulgen 913
-
at 0.2% w/v 94% inhibition
estradiol-17beta
-
inhibits both and C17,20 lyase activity in testis and duodenum, competitive inhibitor
fluconazole
P05093
-
flusilazole
-
-
flusilazole
-
-
iodoacetate
-
at 1 mM 100% inhibition of 17alpha-hydroxylation and 50% inhibition of lyase activity
ketoconazole
-
at 0.00074 mM 50% inhibition
ketoconazole
-
at 150 nM 67% inhibition
ketoconazole
-
at 0.0019 mM 50% inhibition
ketoconazole
-
50% inhibition of hydroxylase activity at 0.00376 mM, of 17,20-lyase activity at 0.00166 mM
ketoconazole
-
-
ketoconazole
-
61.5% inhibition at 0.01 mM
ketoconazole
-
is a weak inhibitor of CYP17, 29% inhibition at 0.0002 mM
ketoconazole
-
unspecific inhibitor
ketoconazole
A6P663
-
ketoconazole
-
i.e. cis-1-acetyl-4-[4[[2,4-(dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]-methoxy]phenyl]piperazine
ketoconazole
-
-
methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
-
-
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
-
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
-
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
-
N-[4'-[(1S)-1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]biphenyl-3-yl]acetamide
-
-
N-[4'-[1-hydroxy(1H-imidazol-4-yl)methyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]-N'-methylurea
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-4-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)ethyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[4'-[cyclopropyl(hydroxy)-1H-imidazol-4-ylmethyl][1,1'-biphenyl]-3-yl]acetamide
-
-
N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
-
N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
-
-
nitrogen
-
complete inhibition
p-chloromercuribenzoate
-
at 1 mM complete inhibition
pregnenolone
-
-
progesterone
-
-
Propiconazole
P05093
-
siRNA
-
siRNA targeting the CYP17 gene
-
Sodium cholate
-
at 0.3% w/v 87% inhibition
Sodium cholate
-
-
tebuconazole
P05093
highest affinity for human CYP17A1
tebuconazole
-
-
tetrabromobisphenol A
-
-
toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
-
-
transforming growth factor-beta1
-
inhibits 17alpha-hydroxylation in vitro by a noncompetitive mechanism
-
triadimenol
P05093
-
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
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
-
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
-
-
methylmercury
-
-
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
-
synthesis and inhibitory potency of inhibitors, overview
-
additional information
-
molecular modelling and docking studies, overview
-
additional information
-
inhibitor development and synthesis, inhibitory potencies of compounds, 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
-
inhibition with anti-P-450 reductase or limitation of NADPH preferentially reduce the lyase activity
-
additional information
-
no enzyme inhibition by (5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol and (5'R)-17beta-[2-(4-fluoroophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
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
-
not inhibited by acetyl pregnenolone
-
additional information
P05093
itraconazole has no effect on human CYP17A1
-
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
-
additional information
P05093
pyridinyl imidazole drugs SB202190 and SB203580 inhibit 17,20 lyase but not 17alpha-hydroxylase activity in human adrenocortical HCI-H295A cells
-
additional information
-
no effect by valproic acid, triclosan, tebuconazole, bisphenol A, tetrabromobisphenol A, methoxyacetic acid, cyclosporin A, endosulfan, methylmercury, perfluorobutane sulfonic acid, perfluorohexane sulfonic acid, perfluorononanoic acid, perfluorooctanoic acid, perfluorooctane sulfate, glufosinate ammonium, dibutyl phthalate, diethylhexyl phthalate, mono-ethylhexyl phthalate, epicatechin, genistein, D-mannitol, diethylstilbestrol, atrazine, retinoic acid, and 4-hydroxy-androstenedione
-
additional information
-
no effect by valproic acid, triclosan, bisphenol A, methoxyacetic acid, cyclosporin A, forskolin, endosulfan, dioctyltin chloride, perfluorobutane sulfonic acid, perfluorohexane sulfonic acid, perfluorononanoic acid, perfluorooctanoic acid, perfluorooctane sulfate, glufosinate ammonium, dibutyl phthalate, diethylhexyl phthalate, mono-ethylhexyl phthalate, epicatechin, genistein, D-mannitol, atrazine, retinoic acid, and 4-hydroxy-androstenedione
-
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
-
cytochrome b5
-
acts as allosteric facilitator but not as electron donor, increases 17,20-lyase activity
-
cytochrome b5
-
-
-
cytochrome b5
-
above pH 6.3-6.5 stimulates 17alpha-hydrolase and c17,20-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
-
plays an important role in regulating the 17,20-lyase reaction catalyzed by CYP17. Rat cytochrome b5 stimulates the 17,20-lyase activity of bovine CYP17A1 by a factor of 4-5
-
cytochrome b5
-
plays an important role in regulating the 17,20-lyase reaction catalyzed by CYP17
-
cytochrome b5
P05093
plays an important role in regulating the 17,20-lyase reaction catalyzed by CYP17. Rat cytochrome b5 stimulates the 17,20-lyase activity of human CYP17A1 by a factor of 5. The H67A mutant of cytochrome b5 and Zn-substituted b5 are both unable to bind heme and therefore fail to stimulate the catalytic activity of CYP17
-
cytochrome b5
-
plays an important role in regulating the 17,20-lyase reaction catalyzed by CYP17
-
cytochrome b5
-
plays an important role in regulating the 17,20-lyase reaction catalyzed by CYP17. Rat cytochrome b5 stimulates the 17,20-lyase activity of bovine CYP17A1 by a factor of 4-5
-
cytochrome b5
-
plays an important role in regulating the 17,20-lyase reaction catalyzed by CYP17
-
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
-
phosphatidylcholine
-
incorporation of P450 into liposomal membranes composed of phosphatidylcholine increases 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
-
not activating: antiepileptic drugs valproic acid, carbamazepine, topiramate, lamotrigine
-
additional information
-
cytochrome B5 does not affect the 17alpha-hydroxylase activity
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0004
17-hydroxypregnenolone
-
wild type enzyme
0.00056
17-hydroxypregnenolone
-
-
0.0008
17-hydroxypregnenolone
-
K89N mutant expressed in Saccharomyces cerevisiae
0.0009
17alpha-hydroxypregnenolone
-
adrenal gland
0.0017
17alpha-hydroxypregnenolone
-
-
0.000525
17alpha-hydroxyprogesterone
-
C17,20 lyase activity in testis
0.000637
17alpha-hydroxyprogesterone
-
C17,20 lyase activity in female duodenum
0.000675
17alpha-hydroxyprogesterone
-
C17,20 lyase activity in male duodenum
0.0024
17alpha-hydroxyprogesterone
-
-
0.0025
17alpha-hydroxyprogesterone
-
adrenal gland
0.00008
pregnenolone
-
wild type enzyme
0.00022
pregnenolone
-
R200N mutant
0.00025
pregnenolone
-
-
0.00055
pregnenolone
-
-
0.0008
pregnenolone
-
adrenal gland
0.0017
pregnenolone
Q29497
isozyme 1, pH 7.4, temperature not specified in the publication
0.0019
pregnenolone
Q29497
isozyme 2, pH 7.4, temperature not specified in the publication
0.0025
pregnenolone
-
-
0.0077
pregnenolone
-
-
0.0000142
progesterone
-
17alpha-hydroxylation in testis
0.0000232
progesterone
-
17alpha-hydroxylation in female duodenum
0.0000238
progesterone
-
17alpha-hydroxylation in male duodenum
0.00024
progesterone
-
wild type enzyme
0.00031
progesterone
-
R200N mutant
0.00045
progesterone
-
-
0.0015
progesterone
-
-
0.0016
progesterone
Q29497
isozyme 1, pH 7.4, temperature not specified in the publication
0.0018
progesterone
-
adrenal gland
0.0018
progesterone
Q29497
isozyme 2, pH 7.4, temperature not specified in the publication
0.0023
progesterone
-
-
0.0063
progesterone
-
-
0.018
5alpha-pregnan-3alpha-ol-20-one
-
pH 7.4
additional information
additional information
-
calculation of intramolecular and intermolecular kinetic isotope effects for wild-type and mutant enzymes, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00283
17alpha-hydroxypregnenolone
-
-
0.0483
progesterone
-
-
0.258
progesterone
-
-
1.55
progesterone
-
17alpha-hydroxylase activity
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.005
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
more than 0.005000
0.000112
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
-
0.000388
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
-
0.0031
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.003100
0.005
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.005000
0.002
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.002000
0.005
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
more than 0.005000
0.005
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
more than 0.005000
0.0014
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
-
0.00046
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
-
0.00031
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
-
0.00078
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
-
0.00079
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
-
0.0021
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
-
0.00058
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
-
0.00105
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
-
0.0003
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
-
0.00045
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
-
0.0023
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
0.0038
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
-
0.0013
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
-
0.000756
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
0.000345
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
-
0.000168
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
-
0.00008
17-(1H-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
-
noncompetitive inhibitor
0.000041
17-(1H-1,2,4-triazol-1-yl)androsta-4,16-dien-3-one
-
noncompetitive inhibitor
0.0000019
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
-
noncompetitive inhibitor
0.0003
17-hydroxypregnenolone
-
R347H-mutant, inhibiton of 17alpha-hydrolase activity
0.0005
17-hydroxypregnenolone
-
K89N-mutant, inhibiton of 17alpha-hydrolase activity
0.0007
17-hydroxypregnenolone
-
wild type, inhibiton of 17alpha-hydrolase activity
0.0008
17-hydroxypregnenolone
-
R358Q-mutant, inhibiton of 17alpha-hydrolase activity
0.00124
17alpha-hydroxyandrosten-3-one
-
C17,20-lyase activity
0.0096
17alpha-hydroxyandrosten-3-one
-
17alpha-hydroxylase activity
0.000118
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
-
0.000282
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
-
0.000029
22-Amino-23,24-bisnor-5-cholen-3beta-ol
-
17alpha-hydroxylase activity
0.005
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
more than 0.005000
0.00004
3-(6-Chloro-3-methyl-2-indenyl)pyridine
-
-
0.0000014
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
-
noncompetitive inhibitor
0.000023
3beta-hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene
-
noncompetitive inhibitor
0.0000012
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
-
noncompetitive inhibitor
0.005
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
more than 0.005000
0.000375
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
0.0003
4-chloro-3,4-dihydro-2-(3-pyridyl)-1-(2H)-naphthalenone
-
-
0.0022
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
-
0.000099
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
-
0.000072
abiraterone
-
-
0.005
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
more than 0.005000
0.00278
ketoconazole
-
-
0.005
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
more than 0.005000
0.0008
pregnenolone
-
competitive substrate with progesterone
0.0032
progesterone
-
competitive substrate with pregnenolone
0.0000000464
transforming growth factor-beta1
-
-
-
0.0017
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
-
0.005
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
-
more than 0.005000
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00006
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00018
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00011
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00027
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00034
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00077
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00024
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00045
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000092
(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.001
(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
IC50 above 0.001 mM, in 75 mM phosphate buffer (pH 7.4), at 37C
0.00001
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37C
0.000015
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00001
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000014
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000026
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000022
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000026
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000033
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000021
(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000028
(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0048
(5'R)-17beta-[2-(2-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
pH 7.3, 37C
0.014
(5'R)-17beta-[2-(3-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
pH 7.3, 37C
0.005
(5'R)-17beta-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
pH 7.3, 37C
0.052
(5'R)-17beta-[2-(4-chlorophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
pH 7.3, 37C
0.0077
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
pH 7.3, 37C
0.0079
(5'R)-17beta-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3beta-ol
-
pH 7.3, 37C
0.03
(5'R)-17beta-[2-phenyl-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
-
pH 7.3, 37C
0.005
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
-
0.000112
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
-
0.000388
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
-
0.0031
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
-
0.005
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
-
0.002
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
0.005
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
-
0.005
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
0.667
1-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
-
-
0.0014
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
-
0.00046
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
-
0.00031
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
-
0.00078
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
-
0.00079
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
-
0.0021
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
-
0.00058
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
-
0.00105
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
-
0.0003
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
-
0.00045
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
-
0.0018
1-(10-phenyl-decyl)-1H-imidazole
-
pH 7.4, 37C
0.00001
1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00013
1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000054
1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00012
1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00015
1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00021
1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0038
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
-
0.0013
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
-
0.000756
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
0.031
1-(3-phenyl-propyl)-1H-imidazole
-
pH 7.4, 37C
0.000019
1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000049
1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000028
1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000029
1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0000083
1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000027
1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000028
1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000164
1-(4-iodobenzyl)-1H-imidazole
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.0076
1-(4-iodobenzyl)-1H-imidazole
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.0087
1-(4-phenyl-butyl)-1H-imidazole
-
pH 7.4, 37C
0.0022
1-(5-phenyl-pentyl)-1H-imidazole
-
pH 7.4, 37C
0.0009
1-(6-phenyl-hexyl)-1H-imidazole
-
pH 7.4, 37C
0.00032
1-(7-phenyl-heptyl)-1H-imidazole
-
pH 7.4, 37C
0.00025
1-(8-phenyl-octyl)-1H-imidazole
-
pH 7.4, 37C
0.00011
1-(9-phenyl-nonyl)-1H-imidazole
-
pH 7.4, 37C
0.0023
1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
0.003
1-benzyl-1H-imidazole
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.1542
1-benzyl-1H-imidazole
-
pH 7.4, 37C
0.000091
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0002
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000015
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000018
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000033
1-[1,1'-biphenyl]-4-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000188
1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
0.000345
1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
0.000168
1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
-
-
0.000206
1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00266
1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.000014
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000028
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.022
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-4-en-3-one
-
pH and temperature not specified in the publication
0.059
17beta-(1-phenyl-5-pyrazolyl)androst-4-en-3-one
-
pH and temperature not specified in the publication
0.003
17beta-(2-oxazolidon-5-yl)-androst-4-en-3-one
-
-
0.000118
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
-
0.000282
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
-
0.000064
2-fluoro-4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)phenol hydrobromide
-
-
0.000188
2-fluoro-4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)phenol hydrobromide
-
-
0.000052
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
0.00009
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
0.005
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
-
0.02
3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
above
0.00235
3-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
0.000217
3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
0.005
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
-
0.000379
4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
-
-
0.000261
4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
-
-
0.000152
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
0.000195
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
-
-
0.000164
4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
-
-
0.000231
4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
0.000375
4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
0.000044
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000049
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000071
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00016
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00147
4-(1H-imidazol-1-ylmethyl)phenol
-
inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.0025
4-(1H-imidazol-1-ylmethyl)phenol
-
inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.000034
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00104
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.00004
4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00007
4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.00002
4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00011
4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.000014
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.0002
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.00013
4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.00016
4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00003
4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00121
4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.00001
4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.0001
4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.000233
4-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
0.02
4-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
above
0.005
4-(5-(4-methoxyphenyl)-3H-inden-1-yl)pyridine hydrochloride
-
above
0.000144
4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
0.000307
4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
0.00122
4-(6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
0.005
4-(6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
above
0.000163
4-(6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
0.005
4-(6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
above
0.00147
4-hydroxybenzyl imidazole
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication
0.002496
4-hydroxybenzyl imidazole
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication
0.000164
4-iodobenzyl imidazole
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication
0.00073
4-iodobenzyl imidazole
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication
0.0022
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
-
0.01
5-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
above
0.02
5-(4-fluorophenyl)-1-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-ol
-
above
0.000333
5-(4-fluorophenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
0.02
5-(4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
above
0.000423
6-(3,4-difluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
0.005
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
above
0.000587
6-(4-fluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
0.000036
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000042
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000019
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00007
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00001
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37C
0.00003
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00016
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.0002
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000012
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000039
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000012
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000075
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000006
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000016
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000013
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000038
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000099
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
-
0.00001
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37C
0.000018
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000015
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000022
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000072
abiraterone
-
-
0.00022
abiraterone
-
-
0.003
benzyl imidazole
-
IC50 above 0.003 mM against 17,20-lyase activity, pH and temperature not specified in the publication; IC50 above 0.003 mM against 17alpha-hydroxylase activity, pH and temperature not specified in the publication
0.005
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
-
0.014
diethylstilbestrol
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.000084
dioctyltin chloride
-
H295R cell assay, pH and temperature not specified in the publication
-
0.00013
flusilazole
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.016
flusilazole
-
H295R cell assay, pH and temperature not specified in the publication
0.000051
ketoconazole
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.00007
ketoconazole
-
H295R cell assay, pH and temperature not specified in the publication
0.000206
ketoconazole
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication
0.00035
ketoconazole
-
-
0.00266
ketoconazole
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication
0.00278
ketoconazole
-
-
0.00378
ketoconazole
-
-
0.0038
ketoconazole
-
pH 7.4, 37C
0.000024
methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000043
methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.02 - 2
methylmercury
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.000011
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000036
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000011
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000046
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.005
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
-
0.000077
N-[4'-[1-hydroxy(1H-imidazol-4-yl)methyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00032
N-[4'-[1-hydroxy(1H-imidazol-4-yl)methyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000021
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]-N'-methylurea
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000024
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]-N'-methylurea
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000017
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000024
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000024
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-4-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00012
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-4-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000038
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)ethyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000062
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)ethyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000025
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.00004
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000045
N-[4'-[cyclopropyl(hydroxy)-1H-imidazol-4-ylmethyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000081
N-[4'-[cyclopropyl(hydroxy)-1H-imidazol-4-ylmethyl][1,1'-biphenyl]-3-yl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000036
N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000053
N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000029
N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000039
N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
-
in 75 mM phosphate buffer (pH 7.4), at 37C
0.000039
SU10603
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.000061
SU10603
-
H295R cell assay, pH and temperature not specified in the publication
0.00014
tebuconazole
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.093
tetrabromobisphenol A
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.00003
toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
-
IC50 against 17,20-lyase activity, pH and temperature not specified in the publication; inhibition of 17alpha-hydroxylase activity, pH not specified in the publication, temperature not specified in the publication
0.00004
toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
-
IC50 against 17alpha-hydroxylase activity, pH and temperature not specified in the publication; inhibition of 17,20-lyase activity, pH not specified in the publication, temperature not specified in the publication
0.0017
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
-
0.005
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000073
-
adrenal cortex microsomes, pH and temperature not specified in the publication
0.0000375
-
H295R cell assay, pH and temperature not specified in the publication
0.008
-
lyase activity
0.023
-
hydroxylase activity
0.058
-
purified recombinant enzyme, activity with progesterone
0.1
-
purified recombinant enzyme, activity with pregnenolone
0.125
-
purified recombinant enzyme, activity with progesterone
0.28
-
purified recombinant enzyme, activity with pregnenolone
0.47
-
purified recombinant enzyme, activity with progesterone
additional information
-
17alpha-hydroxylase and 17,20-lyase activity of recombinant wild-type and mutant enzymes
additional information
-
17alpha-hydroxylase and 17,20-lyase activities of purified enzyme, comparisons of different species, overview
additional information
P05093
17alpha-hydroxylase and 17,20-lyase activities of purified enzyme, comparisons of different species, overview
additional information
-
17alpha-hydroxylase and 17,20-lyase activities of purified enzyme, comparisons of different species, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.1
-
both 17alpha-hydroxylation and C17,20-lyase actiivty
6.6
-
C17,20-lyase activity after addition of cytochrome b5
6.9 - 8.5
-
for 17alpha-hydroxylation of pregnenolone
7
-
17alpha-hydroxylation after addition of cytochrome b5
7.2
-
assay at
7.3
-
assay at
7.4
-
assay at
7.4
-
assay at
7.4
-
assay at
7.4
C7B608
assay at
7.4
Q29497
assay at
7.5
-
assay at
7.5
A6P663
assay at
8.5
-
for 17alpha-hydroxylation of progesterone
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
-
assay at
25
-
assay at
25
A6P663
assay at
37
-
assay at
37
-
assay at
37
C7B608
assay at
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 44
-
hydroxylase and lyase activity decrease proportionally
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
P05093
highest expression
Manually annotated by BRENDA team
-
little lyase activity
Manually annotated by BRENDA team
-
fetal and postnatal
Manually annotated by BRENDA team
-
telencephalon, diencephalon, mesencephalon, metencephalon. Immunoreactivity is almost exclusively located in neurons, distribution in the telencephalon, diencephalon, mesencephalon and metencephalon, detailed expression analysis, overview
Manually annotated by BRENDA team
B2D2I4
expression in ovary during gonad development
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
A6P663
n somatic cells of the indifferent gonad of males and in the interstitial cell of the testis. CYP17 expression is higher in the indifferent gonad during sex differentiation in male than in female tadpoles of Rana rugosa, overview
Manually annotated by BRENDA team
-
fetal and postnatal
Manually annotated by BRENDA team
-
human adrenocorticocarcinoma cell line
Manually annotated by BRENDA team
B2D2I4
low expression level
Manually annotated by BRENDA team
B3VLB1, B6UPD2
high level of P450c17-II expression
Manually annotated by BRENDA team
B3VLB1, B6UPD2
-
Manually annotated by BRENDA team
-
mouse tumor leydig cell defective in 17alphahydroxylase/17,20-lyase activity
Manually annotated by BRENDA team
-
follicles cultured in vitro and lacking estrogen receptor alpha exhibit at late stage a markedly increased expression of steroid 17alpha-hydroxylase and secrete much greater amounts of androstenedione than control. They also exhibit increased testosterone synthesis. Estrogen receptor alpha functions as a repressor of steroid 17alpha-hydroxylase synthesis
Manually annotated by BRENDA team
-
theca-interstitial cell
Manually annotated by BRENDA team
B2D2I4
expression in ovary during gonad development
Manually annotated by BRENDA team
-
islets of Langerhans
Manually annotated by BRENDA team
-
pars distalis, pars intermedia, in the pars distalis and pars intermedia of the pituitary, detailed expression analysis, overview
Manually annotated by BRENDA team
B3VLB1, B6UPD2
-
Manually annotated by BRENDA team
-
neonatal
Manually annotated by BRENDA team
P05093
highest expression
Manually annotated by BRENDA team
-
adult and foetal
Manually annotated by BRENDA team
-
greater lyase than hydroxylase activity
Manually annotated by BRENDA team
A6P663
intestitial cells
Manually annotated by BRENDA team
B3VLB1, B6UPD2
high level of P450c17-I
Manually annotated by BRENDA team
-
polycystic ovary syndrome, PCOS, theca cell, androgen-secreting, from females with polycystic ovary syndrome undergoing hysterectomy or ovarian wedge resection
Manually annotated by BRENDA team
-
a adrenal cortex tissue layer that excretes androgens
Manually annotated by BRENDA team
additional information
A6P663
immunohistochemic analysis of enzyme localization, overview
Manually annotated by BRENDA team
additional information
-
immunohistochemic enzyme localization analysis, overview
Manually annotated by BRENDA team
additional information
C7B608
tissue- and developmental stage-dependent expression patterns, overview. p450c17 expression and ratio of lyase to hydroxylase is high in preparatory and pre-spawning phases of ovary and low in spawning phase. Expression of p450c17 correlats well with testicular recrudescence with maximum expression in preparatory and spawning phases. Neither protein expression nor lyase/hydroxylase activity change significantly during hCG-induced oocyte maturation, while in vitro and in vivo though mRNA levels increase
Manually annotated by BRENDA team
additional information
-
immunohistochemical localisation and molecular expression of P450C17 in the superior, lateral, medial and inferior vestibular nuclei
Manually annotated by BRENDA team
additional information
B2D2I4
semi-quantitative RT-PCR analysis of spatial expression
Manually annotated by BRENDA team
additional information
-
the tissue-specific expression pattern of the CYP17 gene differs among species
Manually annotated by BRENDA team
additional information
P05093
the tissue-specific expression pattern of the CYP17 gene differs among species. The human mRNA appears to be ubiquitously expressed in all tissues,with the highest levels detected in testis and adrenals, and also in various human fetal tissues. The enzyme occurs in steroidogenic cells
Manually annotated by BRENDA team
additional information
-
enzyme expression pattern during the reproductive cycle in ovoviviparous Korean rockfish, quantitative real-time PCR enzyme tissue expression analysis, overview
Manually annotated by BRENDA team
additional information
-
immunohistochemic determination of the enzyme in fetal neural tissues and during development, detailed overview
Manually annotated by BRENDA team
additional information
B3VLB1, B6UPD2
semiquantitative RT-PCR enzyme tissue expression analysis, P450c17-I mRNA expression during the testicular cycle, overview
Manually annotated by BRENDA team
additional information
B3VLB1, B6UPD2
semiquantitative RT-PCR enzyme tissue expression analysis, P450c17-II mRNA expression during the testicular cycle, overview
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
46000
-
SDS-PAGE
390134
53000
-
SDS-PAGE
390141
54000
-
SDS-PAGE
390140
57000
-
-
390147
57000
-
-
692540
59000
-
SDS-PAGE and denaturating gel filtration
390143
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
-
alpha, 1 * 57000
monomer
-
alpha, 1 * 59000
additional information
-
modeling of the tertiary structure of CYP17
additional information
-
modeling of tertiary structure of CYP17, overview
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phosphoprotein
P05093
phosphorylation of the CYP17 protein affects its stability and activity
phosphoprotein
P05093
Ser/Thr phosphorylation of P450c17 appears to promote P450 oxidoreductase-P450c17 interaction. The kinase that phosphorylates P450c17 is p38alpha, the p38beta isozyme is inactive
glycoprotein
-
two N-glycosylation sites in P450c17-I, 191NSSY and 282NNTA, and one N-glycosylation site in P450c17-II, 251NSSL
glycoprotein
-
-
glycoprotein
-
three glucosamine residues per molecule
phospholipoprotein
-
40 nmol phospholipid per mg of protein
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 0.25 M sucrose, pH 7.4, 2 months
-
-70C, 0.2% Emulgen 913 v/v and 20% glycerol v/v, 6 months, no detectable loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant fusion enzyme from Escherichia coli by 2',5'-ADP affinity chromatography
-
recombinant enzyme partially from Pichia pastoris strain GS115 by microsome preparation
-
recombinant His-tagged enzyme from Escherichia coli strain JM109 by nickel affinity chromatography
-
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli strain JM109 by anion exchange and nickel affinity chromatography, hydroxyapatite chromatography, and gel filtration
-
recombinant membrane-embedded His-tagged wild-type and mutant enzymes from Escherichia coli strain JM109 by nickel affinity chromatography
P05093
recombinant wild-type and mutant enzymes from yeast mcirosomes, recombinant modified CYP17A1 from Escherichia coli strain JM109 to homogeneity
-
native enzyme partially from brain microsomes
-
native enzyme partially from pancreatic cell microsomes
-
purification system especially useful for steroid enzyme assays utilizing radiolabeled substrates
-
recombinant fusion enzyme from Escherichia coli by 2',5'-ADP affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sequence comparisons and phylogenetic analysis
-
expression in Saccharomyces cerevisiae strain AH22, fused with yeast reductase, greater 17alpha-hydroxylase activity
-
sequence comparisons and phylogenetic analysis
-
the P450c17 domain of the coding sequence is connected to a truncated form of rat NADPH-P450 reductase by a linker sequence encoding Ser-Thr, functional expression of fusion proteins in Escherichia coli
-
sequence comparisons and phylogenetic analysis
-
expression in monkey kidney COS-1 cells
-
sequence comparisons and phylogenetic analysis
-
the P450c17 domain of the coding sequence is connected to a truncated form of rat NADPH-P450 reductase by a linker sequence encoding Ser-Thr, functional expression of fusion proteins in Escherichia coli
-
gene p450c17, cDNA from ovary, DNA and amino acid sequence determination and analysis, phylogenetic tree, transient expression in COS-7 cells, overexpression in Escherichia coli
C7B608
gene CYP17A1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, semi-quantitative RT-PCR analysis of spatial expression
B2D2I4
sequence comparisons and phylogenetic analysis
-
CYP17, real-time RT-PCR expression analysis
A6P663
co-expression of CYP17 and NADPH-P450 reductase in Escherichia coli, expression of the enzyme in insect cells via baculovirus transfection
-
CYP17, expression in Escherichia coli, co-expression with NADPH-P450 reductase
-
CYP17A1, DNA and amino acid sequence determination and analysis, expression of mutant R239Q in HEK-293 cells
-
DNA and amino acid sequence determination and analysis of wild-type and mutant enzymes, genotyping
-
expression in Escherichia coli cells; gene CYp17, expression in Escherichia coli, coexpression with human cytochrome P450 reductase
-
expression in Escherichia coli JM109, human gene with an (His)4-tail
-
expression in Escherichia coli XL1
-
expression in Escherichia coli, human gene with an (His)4-tail
-
expression in monkey kidney COS-1 cells
-
expression in Saccharomyces cerevisiae strain W303B of the K89N-mutant
-
expression of His-tagged enzyme in Escherichia coli strain JM109, coexpression with molecular chaperones GroES and GroEL
-
expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain JM109
-
expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain JM109, co-expression of P450c17 and p38 in COS-1 cells
P05093
expression of wild-type and mutant C-terminally Bis-tagged enzymes lacking the N-terminal transmembrane helix in Escherichia coli strain JM109
-
expression of wild-type and mutant enzymes in yeast microsomes, expression of modified CYP17A1 in Escherichia coli strain JM109
-
functional expression of cytochrome P45017alpha in Pichia pastoris strain GS115, subcloning in Escherichia coli strain JM109
-
gene CYP17, coexpression in Escherichia coli with human NADPH-P450 reductase
-
gene CYP17, expression in HeLa cells
-
gene CYP17A1, DNA and amino acid sequence determination and analysis of wild-type and mutant enzymes, overview
-
gene CYP17A1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, expression of wild-type and mutant enzymes in COS-1 cells
P05093
gene CYP17A1, genotyping
-
recombinant expression in Escherichia coli
-
recombinant expression in yeast microsomes
-
expression in Cos-1 cells
-
sequence comparisons and phylogenetic analysis
-
DNA and amino acid sequence determination and analysis, CYP17 genotyping, realtime PCR expression analysis
Q29497
sequence comparisons and phylogenetic analysis
-
expression in Escherichia coli JM109, human gene with an (His)4-tail
-
gene CYP17, expression analysis
-
sequence comparisons and phylogenetic analysis
-
genes P450c17-I and P450c17-II, DNA and amino acid sequence determination and analysis, phylogenetic analysis, and quantitative real-time PCR expression analysis
-
sequence comparisons and phylogenetic analysis
-
the P450c17 domain of the coding sequence is connected to a truncated form of rat NADPH-P450 reductase by a linker sequence encoding Ser-Thr, functional expression of fusion proteins in Escherichia coli
-
gene P450c17-I, DNA and amino acid sequence determination and analysis, phylogenetic analysis, semiquantitative RT-PCR enzyme expression analysis; gene P450c17-II, DNA and amino acid sequence determination and analysis, phylogenetic analysis, semiquantitative RT-PCR enzyme expression analysis
B3VLB1, B6UPD2
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
p450c17 expression and ratio of lyase to hydroxylase is high in preparatory and pre-spawning phases of ovary and low in spawning phase. Expression of p450c17 correlates well with testicular recrudescence with maximum expression in preparatory and spawning phases. Neither protein expression nor lyase/hydroxylase activity change significantly during hCG-induced oocyte maturation, while in vitro and in vivo though mRNA levels increase
C7B608
RNAi effectively reduces the expression of exogenous CYP17 in HeLa cells by up to 50%. The CYP17 mRNA and androstenedione production of theca cells are slightly, but not significantly, reduced when compared with non-specific siRNA
-
the expression level of CYP17A1 in adrenals is regulated by ACTH and by gonadotropic hormone in the testis and ovaries. At least three factors, NF1, SF1 and SF3, control the expression level of human CYP17A1 in adrenals. Regions of the CYP17A1 gene responsible for binding transcriptional factors are: nt -107 to -85 and nt -178 to -152 for NF1-1C, nt -227 to -184 for SF1 and SF3
P05093
the enzyme is induced by forskolin
-
three CYP17-targeting lentivirus shRNAs, targeting different sites of CYP17, are constructed and synthesized, that all have a silencing effect on CYP17 mRNA and protein, which leads to a decline of all the levels of androstenedione, 17-hydroxyprogesterone and testosterone to a certain degree, but progesterone levels decline significantly
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L105A
A5HEW0
site-directed mutagenesis, the single point mutation is sufficient to confer 16-hydroxylase activity to the enzyme. It also reduced the rate of progesterone conversion
R200N
-
increased reactivity towards pregnenolone, converts pregnenolone to 17alpha-hydroxypregnenolone and dehydroepiandrosterone, at the expense of 17,20-lyase activity towards 17alpha-hydroxyprogesterone
A105L
-
site-directed mutagenesis, the single point mutation is sufficient to strongly reduce the 16-hydroxylase activity of the enzyme
A105L
-
site-directed mutagenesis, the mutant shows low 21-hydroxylation activity compared to the wild-type enzyme
A174E/K388X
-
naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
D298V
P05093
mutant without heme-binding properties
E305G
-
naturally occuring mutation, the active site mutant shows lack of 17,20-lyase activity and reduced 17alpha-hydroxylase activity compared to the wild-type, males homozygous show a phenotype with severe micropenis, perineal hypospadias, chordae, and bifid scrotum, while females show normal genitalia, genotyping of two families, overview
G111D
P05093
mutant without heme-binding properties
G301I
P05093
mutant without heme-binding properties
G90D
P05093
the mutation results in loss of the 17alpha-hydroxylase and 17,20-lyase activities
H373L
-
the replacement causes complete loss of both 17alpha-hydroxylase and 17,20-lyase activities with a defect in heme binding due to a global alteration of P450c17 structure. The mutation is combined with another mutation, a deletion of codon 53 or 54 encoding Phe, TTC, in exon 1, DELTAF54, on a maternal allele. Both mutations together partially abolish both 17alpha-hydroxylase and 17,20-lyase activities. Enzyme deficiency causes clitoromegaly, phenotype, overview
H373N
-
the substitution results in markedly reduced production of 17alpha-hydroxyprogesterone at 0.2% of the wild-type P450c17 and no production of androstenedione
K89N
-
78% loss of 17,20-lyase activity and 20% loss of 17alpha-hydroxylase activity
P342T
P05093
the mutant shows 20% of wild type activity
Q461stop
P05093
naturally occuring mutation, inactive mutant
R239Q
-
naturally occuring mutation leading to loss of function of CYP17A1 and to enzyme deficiency resulting in failure in synthesizing cortisol, andrenal androgens, and gonadal steroids, phenotype, detailed overview
R347A
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R347H
-
loss of 17,20-lyase activity to a greater extent than 17alpha-hydroxylase activity
R347H
P05093
naturally occuring mutation, results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions, the mutant CYP17A1 loses the ability to interact with cytochrome b5 in recombinant COS-1 cells. Molecular modeling experiments indicate that substitution R347H neutralizes surface positive charges in the region responsible for redox-partner binding
R347H
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R347H
P05093
the mutation results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions
R347H
-
site-directed mutagenesis, the mutant shows no cytochrome b5-CYP17A1 complex formation
R358A
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R358Q
-
loss of 17,20-lyase activity to a greater extent than 17alpha-hydroxylase activity
R358Q
P05093
naturally occuring mutation, results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions, the mutant CYP17A1 loses the ability to interact with cytochrome b5 in recombinant COS-1 cells. Molecular modeling experiments indicate that substitution R358Q neutralizes surface positive charges in the region responsible for redox-partner binding
R358Q
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R358Q
P05093
the mutation results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions
R358Q
-
site-directed mutagenesis, the mutant shows altered cytochrome b5-CYP17A1 complex formation, CYP17A1 R358Q mutant may interact with cytochrome b5 but clearly not in a way that corresponds to wild-type CYP17A1 binding of cytochrome b5
R449A
P05093
naturally occuring mutation, results in loss of the ability of CYP17A1 to catalyze 17,20-lyase reactions
R449A
-
site-directed mutagenesis, the mutant shows abolished activation by cytochrome b5 for the hydroxylase activity and overall highly reduced lyase activityindependently of cytochrome b5
R449A
P05093
the mutation causes loss of 17,20-lyase activity
R449L
-
site-directed mutagenesis, the mutant shows no cytochrome b5-CYP17A1 complex formation
R496C
P05093
naturally occuring mutation, the mutant has low 17alpha-hydroxylase and 17,20-lyase activities
R96Q
-
mutation identified in a female patient with a malignant mixed germ cell tumor. Mutation affects a key substrate-binding region and results in complete inactivity of enzyme
R96W
P05093
the mutation results in loss of the 17alpha-hydroxylase and 17,20-lyase activities
S106P
P05093
the mutation results in loss of the 17alpha-hydroxylase and 17,20-lyase activities
S258A
-
significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
S258D
-
significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
S427A
P05093
site-directed mutagenesis
S427D
P05093
site-directed mutagenesis
S427E
P05093
site-directed mutagenesis
T260D
-
significant decrease in both 17alpha-hydroxylase and 17,20-lyase activity
T306A
-
site-directed mutagenesis, the mutant shows highly reduced hydroxylation activity compared to the wild-type enzyme. due to a high degree of uncoupling in which reducing equivalents and protons are funneled into non-productive pathways. The catalysis of carbon-carbon bond scission by the T306A mutant is largely unimpeded by disruption of the CYP17A1 acid-alcohol pair
T341A
P05093
site-directed mutagenesis
T341A/S427A
P05093
site-directed mutagenesis
T341D
P05093
site-directed mutagenesis
T341E
P05093
site-directed mutagenesis
T64S
P05093
the mutant shows 15% of wild type activity
L105A
Q9GLD2
site-directed mutagenesis, the single point mutation is sufficient to confer 16-hydroxylase activity to the enzyme. It also reduced the rate of progesterone conversion
L105A
P19100
site-directed mutagenesis, the single point mutation is sufficient to confer 16-hydroxylase activity to the enzyme. It also reduced the rate of progesterone conversion
L105A
Capra hircus South African angora
-
site-directed mutagenesis, the single point mutation is sufficient to confer 16-hydroxylase activity to the enzyme. It also reduced the rate of progesterone conversion
-
additional information
Q64410
chimeric constructions of enzyme from Bos taurus and from Cavia porcellus, structural element responsible for switching activity between DELTA4- or DELTA5-pathway is located in the region of polypeptide chain coded by exons II-V of CYP17 gene
L465P
-
naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
additional information
-
FLAG-tagged enzyme shows catalytic parameters undistinguishable from wild-type
additional information
-
mutation of K494_V495 deletion plus R496L and D487_F489 deletion in extreme C-terminus of cytochrome P450c17 identified in a female patient results in complete loss of enzyme activity
additional information
-
construction of a soluble enzyme form by N-terminal truncations, CYP17mod containing hydrophilic FG-loop, a mutant with deleted hydrophobic N-terminal sequence DELTA23 and with a substituted cluster of hydrophobic amino acid residues in the region of the FG-loop, is mostly localized in the cytosolic fraction, replacement of hydrophobic amino acid residues in the FG-loop region does not change the metabolic profile during hydroxylation of steroids that is characteristic for wild type CYP17, overview
additional information
-
reduced c-fos expression in polycystic ovary syndrome leads to reduced enzyme suppression, increased expression and activity resulting in increased androgen production
additional information
-
complete 17-hydroxylase deficiency, 17HD, does not play a role in C19 steroid metabolism, but cortisol-treated 17HD patients cannot produce androstenedione, phenotype, overview
additional information
-
downregulation of CYP17 by siRNA in HeLa cells
additional information
-
knockdown of CYP17 by siRNA
additional information
P05093
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, several patients with 17,20-lyase deficiency carry the substitutions Q461stop and R496C. Mutant Q461stop is not active, whereas mutant R496C has low 17alpha-hydroxylase and 17,20-lyase activities
V178D/R440C
-
naturally occuring mutation leading to CYP17A1 deficiency and adrenal hyperplasia, phenotype, overview
additional information
-
17alphahydroxylase/17,20-lyase knock-down clone shows dramatically reducued human chorionic gonadotropin-induced progesterone formation and de novo synthesis of steroids. Addition of squalene epoxide, lanosterol, zymosterol, and desmosterol can rescue the hormone-induced progesterone formation
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug development
-
the enzyme is a target for inhibitor design
drug development
-
CYP17 is a target for inhibitor design as a target in treatment of prostate cancer
drug development
-
the enzyme is a target for drug development in treatment of prostate cancer, in which androgens play a pivotal role, overview
medicine
-
inhibition of steroid 17alpha-monooxygenase is an important therapeutic strategy in order to inhibit tumor growth in prostate cancer
medicine
-
women with epilepsy have a higher incidence of polycystronic ovary syndrome. At concentrations normally used in antiepileptic drug therapy, the drugs valproic acid, carbamazepine, topiramate, lamotrigine do not influence 17alpha-hydroxylase/17,20-lyase and 3beta-hydroxysteroid dehydrogenase type 2 activities
medicine
-
CYP17 inhibitors are synthesized for the potential treatment of prostate cancer
medicine
-
partial 17alpha-hydroxylase/17,20-lyase deficiency is a very rare form of congenital adrenal hyperplasia
medicine
-
the vital role of CYP17 in androgen biosynthesis makes it a potential molecular target for gene therapetutic strategy