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

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EC NUMBER
COMMENTARY hide
1.14.99.12
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RECOMMENDED NAME
GeneOntology No.
androst-4-ene-3,17-dione monooxygenase
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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.
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CAS REGISTRY NUMBER
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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
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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
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
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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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?
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COFACTOR
ORGANISM
UNIPROT
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LITERATURE
IMAGE
NADPH
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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
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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
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
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GeneOntology No.
LITERATURE
SOURCE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.99.12)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)