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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

Reaction

a C21 steroid
+
[reduced NADPH-hemoprotein reductase]
+
O2
=
a 21-hydroxy-C21-steroid
+
[oxidized NADPH-hemoprotein reductase]
+
H2O

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

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.14.16 steroid 21-monooxygenase

Substrates Products

Substrates Products on EC 1.14.14.16 - steroid 21-monooxygenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-benzphetamine + [reduced NADPH-cytochrome P-450 reductase] + O2
N-demethyl-benzphetamine + [oxidized NADPH-cytochrome P-450 reductase] + H2O
show the reaction diagram
-
-
-
?
11,17-dihydroxyprogesterone + NADH + O2
cortisol + NAD+ + H2O
show the reaction diagram
-
-
-
?
11beta-hydroxyprogesterone + NADH + O2
corticosterone + NAD+ + H2O
show the reaction diagram
-
-
-
?
16,17-dehydroprogesterone + NADPH + O2
16,17-dehydro-21-hydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
?
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
show the reaction diagram
-
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
show the reaction diagram
-
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
show the reaction diagram
-
-
-
-
?
17-hydroxy-progesterone + NADH + O2
17-hydroxy-11-deoxy-corticosterone + NAD+ + H2O
show the reaction diagram
17-hydroxyprogesterone + NADPH + H+ + O2
11-deoxycortisol + NADP+ + H2O
show the reaction diagram
17-hydroxyprogesterone + NADPH + O2
corticosteroids + NADP+ + H2O
show the reaction diagram
-
-
-
?
17-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
17alpha-hydroxy-progesterone + NADH + O2
17alpha-hydroxy-11-deoxy-corticosterone + NAD+ + H2O
show the reaction diagram
-
preferred substrate
-
-
?
17alpha-hydroxyprogesterone + AH2 + O2
11-deoxycortisol + A + H2O
show the reaction diagram
-
-
-
-
?
17alpha-hydroxyprogesterone + NADH + O2
17,21-dihydroxyprogesterone + NAD+ + H2O
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH + H+ + O2
11-deoxycortisol + NADP+ + H2O
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH + H+ + O2
17,21-dihydroxyprogesterone + NADP+ + H2O
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH + O2
11-deoxycortisol + NADP+ + H2O
show the reaction diagram
17alpha-hydroxyprogesterone + NADPH + O2
17,21-dihydroxyprogesterone + NADP+ + H2O
show the reaction diagram
-
-
-
?
17alpha-hydroxyprogesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycortisol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
17alpha-hydroxyprogesterone + [reduced NADPH-P450 reductase] + O2
11-deoxycortisol + [oxidized NADPH-P450 reductase] + H2O
show the reaction diagram
a steroid + electron donor + O2
a 21-hydroxysteroid + oxidized electron donor + H2O
show the reaction diagram
-
essential step in synthesis of steroid hormones by adrenal gland
-
?
allopregnanolone + NADH + O2
21-hydroxy-allopregnanolone + NAD+ + H2O
show the reaction diagram
-
isozyme CYP2D4, CYP2D6
-
-
?
DELTA5-pregnen-3beta,17alpha-diol-20-one + NADH + O2
? + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
DELTA5-pregnen-3beta-ol-20-one + NADH + O2
deoxycorticosterone + NAD+ + H2O
show the reaction diagram
progesterone + AH2 + O2
deoxycorticosterone + A + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADH + O2
11-deoxycorticosterone + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
progesterone + NADH + O2
deoxycorticosterone + NAD+ + H2O
show the reaction diagram
progesterone + NADPH + H+ + O2
11-deoxycorticosterone + NADP+ + H2O
show the reaction diagram
progesterone + NADPH + H+ + O2
deoxycorticosterone + NADP+ + H2O
show the reaction diagram
progesterone + NADPH + O2
deoxycorticosterone + NADP+ + H2O
show the reaction diagram
progesterone + [reduced NADPH-hemoprotein reductase] + O2
11-deoxycorticosterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
progesterone + [reduced NADPH-hemoprotein reductase] + O2
16alpha-hydroxy-progesterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
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
show the reaction diagram
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
show the reaction diagram
additional information
?
-