1.14.14.16: steroid 21-monooxygenase
This is an abbreviated version!
For detailed information about steroid 21-monooxygenase, go to the full flat file.
Word Map on EC 1.14.14.16
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1.14.14.16
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adrenal
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hyperplasia
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cortisol
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virilize
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androgen
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17-hydroxyprogesterone
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glucocorticoid
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children
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acth
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steroidogenic
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testosterone
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adrenocortical
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salt-wasting
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aldosterone
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hirsutism
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nonclassical
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prenatal
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girl
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androstenedione
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genitalia
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steroidogenesis
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mineralocorticoid
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hyperandrogenism
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hydrocortisone
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addison
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puberty
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11-deoxycortisol
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dehydroepiandrosterone
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beta-hydroxysteroid
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11beta-hydroxylase
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adrenarche
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p450scc
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c4a
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endocrinologist
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acth-stimulated
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pseudohermaphroditism
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debrisoquine
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biotechnology
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1'-hydroxylation
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hsd3b2
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incidentalomas
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cyp11b1
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masculinization
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bufuralol
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medicine
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deoxycorticosterone
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adrenocorticotropic
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11-deoxycorticosterone
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17alpha-hydroxylase
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dextromethorphan
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fludrocortisone
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hyperandrogenemia
- 1.14.14.16
- adrenal
- hyperplasia
- cortisol
-
virilize
- androgen
- 17-hydroxyprogesterone
- glucocorticoid
- children
- acth
-
steroidogenic
- testosterone
-
adrenocortical
-
salt-wasting
- aldosterone
- hirsutism
-
nonclassical
-
prenatal
- girl
- androstenedione
- genitalia
- steroidogenesis
-
mineralocorticoid
- hyperandrogenism
- hydrocortisone
- addison
- puberty
- 11-deoxycortisol
- dehydroepiandrosterone
-
beta-hydroxysteroid
-
11beta-hydroxylase
-
adrenarche
- p450scc
- c4a
-
endocrinologist
-
acth-stimulated
- pseudohermaphroditism
- debrisoquine
- biotechnology
-
1'-hydroxylation
- hsd3b2
-
incidentalomas
- cyp11b1
-
masculinization
- bufuralol
- medicine
- deoxycorticosterone
-
adrenocorticotropic
- 11-deoxycorticosterone
- 17alpha-hydroxylase
- dextromethorphan
-
fludrocortisone
-
hyperandrogenemia
Reaction
Synonyms
17alpha-hydroxyprogesterone 21-hydrolase, 21-hydroxylase, 21-hydroxylase cytochrome P-450, 21OH, C3B21RA protein, CYP21, CYP21A2, CYP2D, Cytochrome P-450 specific for steroid C-21 hydroxylation, cytochrome P-450-linked mixed function oxidase system, cytochrome P-450C-21, cytochrome p450 21A2, cytochrome P450 steroid 21-hydroxylase, cytochrome P450c21, EC 1.14.1.8, EC 1.14.99.10, EC 1.99.1.11, P-450(C21), P450 oxidoreductase-21-hydroxylase, P450-C21, P450-C21B, P450c21, Progesterone 21-hydroxylase, Steroid 21-hydroxylase, steroid 21-hydroxylase system, steroid 21-hydroxylation system, steroid cytochrome P450 21-hydroxylase
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.16 - steroid 21-monooxygenase
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REACTION DIAGRAM
(+)-benzphetamine + [reduced NADPH-cytochrome P-450 reductase] + O2
N-demethyl-benzphetamine + [oxidized NADPH-cytochrome P-450 reductase] + H2O
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-
-
?
16,17-dehydroprogesterone + NADPH + O2
16,17-dehydro-21-hydroxyprogesterone + NADP+ + H2O
-
-
-
?
17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one + [reduced NADPH-hemoprotein reductase] + O2
16beta-hydroxy-17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one + 16alpha-hydroxy-17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one + [oxidized NADPH-hemoprotein reductase] + H2O
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i.e. metandienone
product identification by GC-EI-MS analysis
-
?
17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one + [reduced NADPH-hemoprotein reductase] + O2
20beta-hydroxy-17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one + [oxidized NADPH-hemoprotein reductase] + H2O
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i.e. metandienone
product identification by GC-EI-MS analysis
-
?
17-fluoro-progesterone + [reduced NADPH-P450 reductase] + O2
17-fluoro-11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O
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-
-
-
?
17-hydroxyprogesterone + NADPH + O2
corticosteroids + NADP+ + H2O
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-
-
?
17-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
17alpha-hydroxy-progesterone + NADH + O2
17alpha-hydroxy-11-deoxy-corticosterone + NAD+ + H2O
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preferred substrate
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-
?
17alpha-hydroxyprogesterone + AH2 + O2
11-deoxycortisol + A + H2O
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-
-
-
?
17alpha-hydroxyprogesterone + NADPH + O2
17,21-dihydroxyprogesterone + NADP+ + H2O
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-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
17alpha-hydroxyprogesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycortisol + [oxidized NADPH-P450 reductase] + H2O
a steroid + electron donor + O2
a 21-hydroxysteroid + oxidized electron donor + H2O
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essential step in synthesis of steroid hormones by adrenal gland
-
?
allopregnanolone + NADH + O2
21-hydroxy-allopregnanolone + NAD+ + H2O
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isozyme CYP2D4, CYP2D6
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
progesterone + [reduced NADPH-hemoprotein reductase] + O2
16alpha-hydroxy-progesterone + [oxidized NADPH-hemoprotein reductase] + H2O
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mutant V359A produces an additional metabolite, 16alpha-hydroxyprogesterone of progesterone, very low activity with the wild-type enzyme
product identification by TLC
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
16alpha-hydroxyprogesterone + [oxidized NADPH-hemoprotein reductase] + H2O
mutants V359A and V359G both produce an additional metabolite, 16alpha-hydroxyprogesterone
product identification by TLC
-
?
progesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O
17-hydroxy-11-deoxy-corticosterone + NAD+ + H2O
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-
-
-
?
17-hydroxy-progesterone + NADH + O2
17-hydroxy-11-deoxy-corticosterone + NAD+ + H2O
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isozyme CYP2D
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-
?
11-deoxycortisol + NADP+ + H2O
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-
-
-
?
17-hydroxyprogesterone + NADPH + H+ + O2
11-deoxycortisol + NADP+ + H2O
-
-
-
?
17-hydroxyprogesterone + NADPH + H+ + O2
11-deoxycortisol + NADP+ + H2O
the redox cofactor provides the electrons required for a P450-dependent hydroxylation. Maximal CYP 21 activity is observed in presence of low substrate concentrations of 0.2 mM. Higher substrate concentrations reduce the activity and inhibit the enzyme
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-
?
17,21-dihydroxyprogesterone + NAD+ + H2O
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-
-
?
17alpha-hydroxyprogesterone + NADH + O2
17,21-dihydroxyprogesterone + NAD+ + H2O
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-
-
?
17alpha-hydroxyprogesterone + NADH + O2
17,21-dihydroxyprogesterone + NAD+ + H2O
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-
-
-
?
17alpha-hydroxyprogesterone + NADH + O2
17,21-dihydroxyprogesterone + NAD+ + H2O
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-
-
?
17alpha-hydroxyprogesterone + NADH + O2
17,21-dihydroxyprogesterone + NAD+ + H2O
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-
-
?
11-deoxycortisol + NADP+ + H2O
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P450c21 catalyzes hydroxylation at C-21, 17alpha-hydroxyprogesterone is a better substrate for P450c21 than progesterone from the catalytic coupling with consumption of NADPH
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-
?
17alpha-hydroxyprogesterone + NADPH + H+ + O2
11-deoxycortisol + NADP+ + H2O
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-
-
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?
17,21-dihydroxyprogesterone + NADP+ + H2O
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-
-
?
17alpha-hydroxyprogesterone + NADPH + H+ + O2
17,21-dihydroxyprogesterone + NADP+ + H2O
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-
-
-
?
11-deoxycortisol + NADP+ + H2O
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-
-
?
17alpha-hydroxyprogesterone + NADPH + O2
11-deoxycortisol + NADP+ + H2O
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-
-
?
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
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-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
preferred substrate. The 17alpha-hydroxyprogesterone metabolites formed by mutants of V470 and I471 include a second, unidentified product. Both mutants V359A and V359G also metabolize 17alpha-hydroxyprogesterone to 11-deoxycortisol and this second product, and for mutation V359G, the unidentified compound is the major product. The second compound is not androstenedione and is neither the 16alpha- nor 6beta-hydroxylation products (pregn-4-ene-16alpha,17alpha-diol-3,20-dione and pregn-4-ene-6beta,17alpha-diol-3,20-dione, respectively)
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-
?
11-deoxycortisol + [oxidized NADPH-P450 reductase] + H2O
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-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycortisol + [oxidized NADPH-P450 reductase] + H2O
two 17alpha-hydroxyprogesterone molecules are bound to the enzyme, the distal one being located at the entrance of the substrate access channel and the proximal one bound in the active site
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-
?
17alpha-hydroxyprogesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycortisol + [oxidized NADPH-P450 reductase] + H2O
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-
-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycortisol + [oxidized NADPH-P450 reductase] + H2O
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-
-
?
deoxycorticosterone + NAD+ + H2O
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-
very small yields, presumably via dehydrogenation followed by C-21 hydroxylation
?
DELTA5-pregnen-3beta-ol-20-one + NADH + O2
deoxycorticosterone + NAD+ + H2O
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no substrate of cytochrome P-450-linked mixed function oxidase system
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-
?
progesterone + NADH + O2
deoxycorticosterone + NAD+ + H2O
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isozyme CYP2D
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-
?
11-deoxycorticosterone + NADP+ + H2O
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P450c21 catalyzes hydroxylation at C-21
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-
?
progesterone + NADPH + H+ + O2
11-deoxycorticosterone + NADP+ + H2O
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-
-
?
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
?
11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O
-
-
-
?
progesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O
-
-
-
-
?
progesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-P450 reductase] + H2O
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-
-
?
?
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-
no substrate: 17alpha-hydroxy-progesterone
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-
?
additional information
?
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enzyme deficiency, i.e. 21-OHD, causes congenital adrenal hyperplasia in pubertal subjects
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-
?
additional information
?
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CYP21 performs the regio- and stereo-selective 21-hydroxylation of 17-alpha-hydroxyprogesterone when recombinantly expressed in Schizosaccharomyces pombe
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-
?
additional information
?
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CYP21 performs the regio- and stereo-selective 21-hydroxylation of 17-alpha-hydroxyprogesterone when recombinantly expressed in Schizosaccharomyces pombe
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-
?
additional information
?
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metandienone hydroxylation activities and metabolism in vivo, product analysis, overview
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-
?
additional information
?
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17alpha-hydroxyprogesterone is hydroxylated 28times faster than progesterone by the wild-type enzyme. No activity of the wild-type enzyme with pregnenolone, 17alpha-hydroxypregnenolone, and 5alpha-pregnane-3alpha-ol-20-one (allopregnanolone)
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-
?
additional information
?
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-
17alpha-hydroxyprogesterone is hydroxylated 28times faster than progesterone by the wild-type enzyme. No activity of the wild-type enzyme with pregnenolone, 17alpha-hydroxypregnenolone, and 5alpha-pregnane-3alpha-ol-20-one (allopregnanolone)
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-
?
additional information
?
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-
21-trifluorosteroids mht by a substrates for CYP21A2, substrate specificity analysis of CP21A2 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
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-
?
additional information
?
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-
human CYP21A2 also has progesterone 16alpha-hydroxylase activity. Product analysis by LC-MS/MS
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-
?
additional information
?
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C-H bond breaking is a rate-limiting step over a 10000fold range of catalytic efficiency
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?
additional information
?
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C-H bond breaking is a rate-limiting step over a 10000fold range of catalytic efficiency
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-
?