Information on EC 1.14.99.12 - androst-4-ene-3,17-dione monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.99.12
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RECOMMENDED NAME
GeneOntology No.
androst-4-ene-3,17-dione monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
androstenedione + AH2 + O2 = testololactone + A + H2O
show the reaction diagram
FNR is able to transfer electrons between one-electron carriers, ferredoxin or flavodoxin, and two-electron carriers, NADP+ and NADPH, involving its redox cofactor FAD, involvement of Glu312 in the FNR catalytic mechanism not only as a proton donor but also as a key residue for stabilizing and destabilizing reaction intermediates, reaction mechanism and catalytic cycle, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Steroid hormone biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
androst-4-ene-3,17-dione-hydrogen-donor:oxygen oxidoreductase (13-hydroxylating, lactonizing)
Has a wide specificity. A single enzyme from the ascomycete Neonectria radicicola (EC 1.14.13.54, ketosteroid monooxygenase) catalyses both this reaction and that catalysed by EC 1.14.99.4, progesterone monooxygenase.
CAS REGISTRY NUMBER
COMMENTARY hide
37256-74-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
the steroid monooxygenase also has androstenedione monooxygenase activity
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3,17-dione + AH2 + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + A + H2O
show the reaction diagram
androst-4-ene-3,17-dione + NADPH + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + NADP+ + H2O
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3,17-dione + AH2 + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + A + H2O
show the reaction diagram
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enzyme levels increase after exposure of rats to di-n-butyl phthalate
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5-Pregnene-3beta,20alpha-diol
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5alpha-androstane-17beta-ol
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exhibits an IC50 of 0.046 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.026 against androstendione 16alpha-hydroxylase activity and an IC50 of 0.047 against androstendione 16beta-hydroxylase activity
5alpha-androstane-3beta-ol
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exhibits an IC50 of 0.11 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.071 mM against androstendione 16alpha-hydroxylase activity
5alpha-androstane-3beta-ol-17-one
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exhibits an IC50 of 0.12 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.14 against androstendione 16beta-hydroxylase activity
5beta-androstane-17beta-ol
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exhibits an IC50 of 0.11 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.065 against androstendione 16alpha-hydroxylase activity
5beta-androstane-3-one-17-one
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exhibits an IC50 of 0.084 mM against androstendione 7alpha-hydroxylase activity
5beta-androstane-3beta-ol
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exhibits an IC50 of 0.027 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.007 mM against androstendione 16alpha-hydroxylase activity
5beta-androstane-3beta-ol-17-one
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exhibits an IC50 of 0.047 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.06 mM against androstendione 7alpha-hydroxylase activity and an IC50 of 0.051 against androstendione 16alpha-hydroxylase activity and an IC50 of 0.087 against androstendione 16beta-hydroxylase activity; exhibits an IC50 of 0.095 against androstendione 16alpha-hydroxylase activity
dehydroepiandrosterone
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p-Mercuriphenylsulfonate
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in presence of NADPH
pregnenolone
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progesterone
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testosterone
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Testosterone acetate
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additional information
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5beta-reduced steroids are more potent inhibitors than 5alpha-reduced epimers
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04
androst-4-ene-3,17-dione
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0.002
NADPH
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.45
testololactone
Ilyonectria destructans
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formed
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.026 - 0.047
5alpha-androstane-17beta-ol
0.071
5alpha-androstane-3beta-ol
Rattus norvegicus
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exhibits an IC50 of 0.11 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.071 mM against androstendione 16alpha-hydroxylase activity
0.12 - 0.14
5alpha-androstane-3beta-ol-17-one
0.065 - 0.11
5beta-androstane-17beta-ol
0.084
5beta-androstane-3-one-17-one
Rattus norvegicus
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exhibits an IC50 of 0.084 mM against androstendione 7alpha-hydroxylase activity
0.007
5beta-androstane-3beta-ol
Rattus norvegicus
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exhibits an IC50 of 0.027 mM against androstendione 6beta-hydroxylase activity and an IC50 of 0.007 mM against androstendione 16alpha-hydroxylase activity
0.095
5beta-androstane-3beta-ol-17-one
Rattus norvegicus
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exhibits an IC50 of 0.095 mM against androstendione 16alpha-hydroxylase activity
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7 - 7.8
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about 50% of activity maximum at pH 5.7 and 7.8
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE