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Enzyme
JL (1981). "Solubilization and partial purification of a microsomal 3-ketosteroid reductase of cholesterol biosynthesis". Arch. Biochem. Biophys. 211 (1):
3-Ketosteroid_reductase
Chemical compound
ketosteroid, or an oxosteroid, is a steroid in which a hydrogen atom has been replaced with a ketone (C=O) group. A 17-ketosteroid is a ketosteroid in
Ketosteroid
Class of enzymes
1.51), also 17-ketosteroid reductases (17-KSR), are a group of alcohol oxidoreductases which catalyze the reduction of 17-ketosteroids and the dehydrogenation
17β-Hydroxysteroid dehydrogenase
17β-Hydroxysteroid_dehydrogenase
Class of enzymes
3-ketosteroid 9alpha-monooxygenase (EC 1.14.13.142, KshAB, 3-ketosteroid 9alpha-hydroxylase) is an enzyme with systematic name androsta-1,4-diene-3,17-dione
3-Ketosteroid 9alpha-monooxygenase
3-Ketosteroid_9alpha-monooxygenase
Chemical compound
3α-androstenol or 3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase. Androstadienone is related to the androgen sex hormones; however
Androstadienone
Class of enzymes
Δ4-5β-reductase, steroid 5β-reductase, testosterone 5β-reductase, Δ4-3-ketosteroid 5β-reductase, Δ4-5β-reductase, Δ4-hydrogenase, 4,5β-dihydrocortisone:NADP+
5β-Reductase
Class of oxidoreductase enzymes
hydroxysteroids. These enzymes also catalyze the reverse reaction, acting as ketosteroid reductases (KSRs). There are four types, classified by the number of
Hydroxysteroid_dehydrogenase
Enzyme
so on. This enzyme catalyzes the chemical reaction of conversion of 3-ketosteroids into 3α-hydroxysteroids. The enzyme has various protein isoforms (isozymes)
3α-Hydroxysteroid dehydrogenase
3α-Hydroxysteroid_dehydrogenase
Class of enzymes
Ketosteroid monooxygenase (EC 1.14.13.54, steroid-ketone monooxygenase, progesterone, NADPH2:oxygen oxidoreductase (20-hydroxylating, ester-producing)
Ketosteroid_monooxygenase
Primary male sex hormone
40% of testosterone is metabolized in equal proportions into the 17-ketosteroids androsterone and etiocholanolone via the combined actions of 5α- and
Testosterone
Chemical compound
the original publications on this chemical is the bromination of the 3-ketosteroid 1 to 2,4-dibromocholestanone (2): Djerassi, Carl; Caesar R. Scholz (January
Pyridinium_perbromide
Polycyclic organic compound having sterane as a core structure
C21-steroids for the pregnanes (mostly corticosteroids). The classification "17-ketosteroid" is also important in medicine. The gonane (steroid nucleus) is the parent
Steroid
Chemical compound
is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of testosterone. It causes fever
Etiocholanolone
Class of enzymes
adenine dinucleotide, phosphate:Delta4-3-ketosteroid 5alpha-oxidoreductase, 4-ene-5alpha-reductase, Delta4-3-ketosteroid 5alpha-oxidoreductase, cholest-4-en-3-one
Cholestenone_5alpha-reductase
Enlargement of the human male breast
Markers of testicular, adrenal, or other tumors, such as urinary 17-ketosteroid or serum dehydroepiandrosterone, may also be checked if there is evidence
Gynecomastia
Chemical compound
5α-reductase, and can be converted into 3α-androstenol or 3β-androstenol by 3-ketosteroid reductase. Depending upon the subject, androstenone can have an unpleasant
Androstenone
Class of chemicals derived from steroids
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Secosteroid
Steroid acid in the bile of animals
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Bile_acid
Chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Etiocholane
Swedish scientist (born 1943)
after his retirement, for example studies of their role as efficient ketosteroid isomerases and as enzymes involved in the biosynthesis of moulting hormones
Bengt_Mannervik
Chemical compound
androst-5-en-3β-ol-17-one, is a naturally occurring androstane steroid and a 17-ketosteroid. It is closely related structurally to androstenediol (androst-5-ene-3β
Dehydroepiandrosterone
Class of enzymes
Other names in common use include ketosteroid isomerase (KSI), hydroxysteroid isomerase, steroid isomerase, Δ5-ketosteroid isomerase, Δ5(or Δ4)-3-keto steroid
Steroid_Delta-isomerase
Family of aldo-keto reductase enzymes
dehydrogenases, respectively. The AKR1C enzymes act as 3-, 17- and 20-ketosteroid reductases, while AKR1D1 acts as the sole 5β-reductase in humans. AKR1A1;
AKR1
Endogenous weak androgen
androst-4-ene-3,17-dione, is a naturally occurring androstane steroid and a 17-ketosteroid. It is closely related structurally to androstenediol (A5; androst-5-ene-3β
Androstenedione
Class of chemical compounds
sterols, with an example being cholesterol. Hydroxysteroid dehydrogenase Ketosteroid Hydroxysteroids at the U.S. National Library of Medicine Medical Subject
Hydroxysteroid
Index of enzymes associated with the same name
17beta-dehydrogenase 17β-Hydroxysteroid dehydrogenase (17β-HSD, HSD17B), also 17-ketosteroid reductases (17-KSR) This set index page lists enzyme articles associated
17beta_dehydrogenase
Group of protein families
subfamily 3 (NR3) that include receptors for estrogen (group NR3A) and 3-ketosteroids (group NR3C). In addition to nuclear receptors, several G protein-coupled
Steroid_hormone_receptor
Enzyme family
reductase Δ4-3-Ketosteroid-5α-oxidoreductase Δ4-3-Oxosteroid-5α-reductase 3-Keto-Δ4-steroid-5α-reductase Testosterone 5α-reductase 4-Ene-3-ketosteroid-5α-oxidoreductase
5α-Reductase
Class of steroids
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Norsteroid
Class of enzymes
Delta4-5alpha-reductase, microsomal steroid reductase (5alpha), Delta4-3-ketosteroid reductase (5alpha), Delta4-3-oxosteroid-5alpha-reductase,
Cortisone_alpha-reductase
Chemical compound
PMPH-USA. pp. 247–. ISBN 978-1-60795-008-0. Hamburger C (1952). "17-Ketosteroid Excretion and Modes of Administering Testosterone Preparations". Ciba
Testosterone_propionate
Class of enzymes
(R)-20-hydroxysteroid dehydrogenase, dehydrogenase, 20beta-hydroxy steroid, Delta4-3-ketosteroid hydrogenase, 20beta-hydroxysteroid dehydrogenase, 3alpha
3alpha(or 20beta)-hydroxysteroid dehydrogenase
3alpha(or_20beta)-hydroxysteroid_dehydrogenase
Chemical compound
developed by Ciba Pharmaceutical Company. A study found that, measured by 17-ketosteroid excretion, 300 mg testosterone propionate in oil solution had a duration
Testosterone_phenylacetate
Chemical compound
Kaspar E, Schenck M, "Production of 1,2-methylene and 16,17-methylene Ketosteroids ", issued 31 March 1964, assigned to Schering A.G. US 3234093, Wiechert
Cyproterone_acetate
Biological rhythm of about 7 days
resolution of low-frequency, small-amplitude rhythms in excreted 17-ketosteroid: probable androgen-induced circaseptan desynchronization". Acta Endocrinol
Circaseptan
Chemical compound
"Diethylstilbestrol therapy in young men with acne; correlation with the urinary 17-ketosteroids". A.M.A. Archives of Dermatology and Syphilology. 65 (5): 601–608. doi:10
Diethylstilbestrol
System of communication
subfamily 3 (NR3) that include receptors for estrogen (group NR3A) and 3-ketosteroids (group NR3C). In addition to nuclear receptors, several G protein-coupled
Cell_signaling
Corticosteroid medication
mediated by 11 beta-hydroxysteroid dehydrogenases (11[beta]-HSD) and 20-ketosteroid reductases. Methylprednisolone undergoes renal excretion of hydrophilic
Methylprednisolone
Chemical compound
[Process for the preparation of 16α-methyl-16β-halomethyl-17-ketosteroids]", published 1964-03-12, assigned to Merck AG Vitali R, Gardi R, Falconi
Mesabolone
Pharmaceutical compound
ISBN 978-0-08-053620-0. Hamburger C (August 1958). "Testosterone treatment and 17-ketosteroid excretion. V. Administration of testosterone per rectum". Acta Endocrinologica
Pharmacokinetics of testosterone
Pharmacokinetics_of_testosterone
Chemical compound
(March 1987). "Identification of cortisone 5 beta-reductase as delta 4-3-ketosteroid 5 beta-reductase". Biochimica et Biophysica Acta (BBA) - Protein Structure
Dihydrocortisone
Chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Estrin_(molecule)
Chemical compound
is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D₂, and other endogenous and xenobiotic carbonyl compounds"
Hexobarbital
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Pregnenedione
Sex hormone
Gobec S, Rižner TL (May 2011). "Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3". Chemico-Biological Interactions. 191
Progesterone
Progestin medication
in men employing doses of 20 to 50 mg/day observed suppression of 17-ketosteroid excretion, increased estrogen excretion (due to conversion into ethinylestradiol)
Norethisterone
Rare autosomal recessive disorder causing impaired masculinisation
17β-Hydroxysteroid dehydrogenase III deficiency Other names 17 alpha ketosteroid reductase deficiency of testis, 46,XY difference of sex development due
17β-Hydroxysteroid dehydrogenase III deficiency
17β-Hydroxysteroid_dehydrogenase_III_deficiency
Androgen and anabolic steroid
Testosterone esters Hamburger C (August 1956). "Testosterone treatment and 17-ketosteroid excretion. IV. Administration of testosterone beta-cyclopentylpropionate
Testosterone_furoate
Class of enzymes
3-oxosteroid Delta1-dehydrogenase, Delta1-dehydrogenase, 3-ketosteroid-1-en-dehydrogenase, 3-ketosteroid-Delta1-dehydrogenase, 1-ene-dehydrogenase, 3-oxosteroid:(2
3-oxosteroid_1-dehydrogenase
Tetracyclic hydrocarbon parent of the steroids
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Gonane
Mammalian protein found in Homo sapiens
"A tale of two isomerases: compact versus extended active sites in ketosteroid isomerase and phosphoglucose isomerase". Biochemistry. 50 (43): 9283–9295
Glucose-6-phosphate_isomerase
Chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Pregnane
Catalysis of chemical reactions by enzymes
2014). "Extreme electric fields power catalysis in the active site of ketosteroid isomerase". Science. 346 (6216). New York, N.Y.: 1510–4. Bibcode:2014Sci
Enzyme_catalysis
Chemical compound
perfused testis since Medrogestone is a potent inhibitor of the Δ5-3-ketosteroid isomerase enzyme (52) and should therefore inhibit testosterone biosynthesis
Medrogestone
Class of enzymes
and properties of 3-beta-hydroxysteroid dehydrogenase and delta-5-3-ketosteroid isomerase from bovine corpora lutea". Biochim. Biophys. Acta. 122 (1):
3β-Hydroxysteroid dehydrogenase
3β-Hydroxysteroid_dehydrogenase
Procedure for identifying or quantifying a chemical compound or group
determination tests for specific amino acids The Zimmermann test tests for ketosteroids Seliwanoff's test differentiates between aldose and ketose sugars Test
Chemical_test
Chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Cardanolide
Chemical compound
Gobec S, Rižner TL (May 2011). "Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3". Chemico-Biological Interactions. 191
Dydrogesterone
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
List_of_androstanes
Protein family
"Structural Coupling Throughout the Active Site Hydrogen Bond Networks of Ketosteroid Isomerase and Photoactive Yellow Protein". Journal of the American Chemical
Photoactive_yellow_protein
Chemical compound
(August 2001). "Gene structure, chromosomal localization and analysis of 3-ketosteroid reductase activity of the human 3(alpha-->beta)-hydroxysteroid epimerase"
Epiandrosterone
Medical usage of the prasterone compound
androst-5-en-3β-ol-17-one, is a naturally occurring androstane steroid and a 17-ketosteroid. It is closely related structurally to androstenediol (androst-5-ene-3β
Prasterone
Chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
19-Norpregnane
Class of chemical compounds
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Pregnatriene
Addition reaction
the preparation of steroid hormones. For example, ethynylation of 17-ketosteroids produces important contraceptive medications known as progestins. Examples
Alkynylation
Protein
Estrogen-related receptor-β ESRRB NR3B3 ERRγ Estrogen-related receptor-γ ESRRG C 3-Ketosteroid receptors NR3C1 GR Glucocorticoid receptor NR3C1 cortisol NR3C2 MR Mineralocorticoid
Nuclear_receptor
Drug class
trilostane inhibit the conversion of Δ5-3β-hydroxysteroids into Δ4-3-ketosteroids and thereby inhibit the production of most of the steroid hormones. Due
Steroidogenesis_inhibitor
Class of chemical compounds
Claisen rearrangement with a catalytic dyad similar to that found in ketosteroid isomerase. A Spiroligomer peptidomimetic was designed to mimic P53 and
Spiroligomer
Chemical compound
17α-hydroxypregnenolone, dehydroepiandrosterone (DHEA), and androstenediol, into Δ4-3-ketosteroids, including progesterone, 17α-hydroxyprogesterone, androstenedione, and
Trilostane
Protein-coding gene in the species Homo sapiens
binding protein binding carboxylic acid binding oxidoreductase activity ketosteroid monooxygenase activity alcohol dehydrogenase (NADP+) activity steroid
AKR1C1
Type of enzyme
(CYP1, 2, 3) – estrogen metabolism Hydroxysteroid dehydrogenases (and ketosteroid reductases) 3α-Hydroxysteroid dehydrogenase – androgen, progestogen,
Steroidogenic_enzyme
Chemical compound
nuclear reduced nicotinamide adenine dinucleotide phosphate: delta 4-3-ketosteroid 5 alpha-oxidoreductase of rat prostate". The Journal of Biological Chemistry
5α-Pregnan-17α-ol-3,20-dione
Class of chemical compounds
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Azasteroid
Chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Estrane
Type of medication
"Diethylstilbestrol therapy in young men with acne; correlation with the urinary 17-ketosteroids". AMA Arch Dermatol Syphilol. 65 (5): 601–8. doi:10.1001/archderm.1952
Estrogen_(medication)
Class of organic compounds
reaction is the basis of the Zimmermann test used for the detection of ketosteroids. The Jackson–Meisenheimer complex was named after the American organic
Meisenheimer_complex
Chemical compound
Chen M, Penning TM (May 2014). "5β-Reduced steroids and human Δ(4)-3-ketosteroid 5β-reductase (AKR1D1)". Steroids. 83: 17–26. doi:10.1016/j.steroids.2014
Tetrahydrocortisol
Organic redox reaction in chemistry
6-3-ketosteroids with benzoquinone as the hydrogen acceptor. This reaction is useful in that it affords a one-step preparation of Δ 4,6-3-ketosteroids. In
Oppenauer_oxidation
Spanish scientist (1917–1999)
of adrenal corticosteroids and the chromatographic separation of 17-ketosteroids. In 1953, with a grant from the Institute of International Education
Sara_Borrell_Ruiz
Organic reaction
; Kritchevsky, Theodore H. (1950). "Perbenzoic Acid Oxidation of 20-Ketosteroids and the Stereochemistry of C-17". J. Am. Chem. Soc. 72 (2): 882–885.
Baeyer–Villiger_oxidation
1,2-migration of an alkyl or aryl group
effects were observed in studies of the rearrangement of 17-hydroxy-20-ketosteroids. In this case, Lewis-acidic conditions switched the sense of stereoselectivity
Α-Ketol_rearrangement
{{cite book}}: ISBN / Date incompatibility (help) Hamburger C (1952). "17-Ketosteroid Excretion and Modes of Administering Testosterone Preparations". Ciba
Pharmacokinetics of progesterone
Pharmacokinetics_of_progesterone
Change in chemical reaction rate due to isotopic substitution
inside a reaction site provides tunneling-promoting vibration. Studies on ketosteroid isomerase have provided experimental evidence that the enzyme actually
Kinetic_isotope_effect
Chemical compound
"Characterization and application of fusidane antibiotic biosynethsis enzyme 3-ketosteroid-∆1-dehydrogenase in steroid transformation". Appl Microbiol Biotechnol
Fusidane
Protein-coding gene in the species Homo sapiens
Moller G, et al. (2004). "Closing the gap: identification of human 3-ketosteroid reductase, the last unknown enzyme of mammalian cholesterol biosynthesis"
HSD17B7
trenbolone MeSH D04.808.496.699 – testolactone MeSH D04.808.578.502 – 17-ketosteroids MeSH D04.808.578.502.112 – androstenedione MeSH D04.808.578.502.195 –
List_of_MeSH_codes_(D04)
Now EC 1.14.14.89, 4′-methoxyisoflavone 2′-hydroxylase EC 1.14.13.54: ketosteroid monooxygenase EC 1.14.13.55: Now EC 1.14.14.98, protopine 6-monooxygenase
List_of_EC_numbers_(EC_1)
Chemical compound
(2012). "Metabolism of the synthetic progestogen norethynodrel by human ketosteroid reductases of the aldo-keto reductase superfamily". J. Steroid Biochem
Noretynodrel
Danish endocrinologist
gonadotropin. His later research covered topics including androgen hormones, 17-ketosteroids, antigonadotropins, and methods for administering sex hormones. Hamburger
Christian_Hamburger
Trans male author
Martino and other technicians took a 17-ketosteroid urine test, where it was found that he had "the 17-ketosteroids of a 17-year-old male". While working
Mario_Martino
Protein-coding gene in the species Homo sapiens
JF, Miller WL (Dec 1989). "Regulation of the gene for estrogenic 17-ketosteroid reductase lying on chromosome 17cen----q25". The Journal of Biological
HSD17B1
Species of bacterium
[Production of 20 beta-hydroxysteroids from 17 alpha, 21-dihydroxy-20-ketosteroids by microbiological hydration with Streptomyces hydrogenans]. Hoppe-Seyler's
Streptomyces_hydrogenans
Chemical compound
Rundle A (July 1956). "Changes in the excretion pattern of neutral 17-ketosteroids during oestrogen administration to male subjects". The Journal of Endocrinology
Estradiol_undecylate
Chemical compound
Gobec S, Rižner TL (2011). "Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3". Chem. Biol. Interact. 191 (1–3): 227–33
20α-Dihydroprogesterone
limonene-1,2-epoxide hydrolase, SnoaL polyketide cyclase, and delta-5-3-ketosteroid isomerase (KSI). Most, if not all, of the members of the NTF2 superfamily
Orange_carotenoid_protein
Steroid chemical compound
Cardanolide C24 Cholane Bile acid C27 Cholestane Functional group 17-Ketosteroid Hydroxysteroid Halogenated steroid Elements removed Norsteroid Secosteroid
Allopregnane
(2001). "Gene structure, chromosomal localization and analysis of 3-ketosteroid reductase activity of the human 3(alpha-->beta)-hydroxysteroid epimerase"
HSD17B6
Species of bacterium
intermediate ratio indicated that 7-β dehydratase affected NADH levels. baiI (Δ-ketosteroid isomerase/7-β dehydratase): baiI, the furthest downstream gene of the
Clostridium_scindens
Chemical compound
genistein, daidzein, coumestrol and C18-, C19- and C21 hydroxysteroids and ketosteroids". Steroids. 70 (8): 507–514. doi:10.1016/j.steroids.2005.01.004. PMID 15894034
Coumestrol
American scientist
Elizabeth; Hopkins, Carl E. (June 1965). "I. Urinary excretion of neutral 17-ketosteroids and pregnanediol by patients with breast cancer and benign breast disease"
Jessie_Marmorston
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