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Information on EC 1.14.99.12 - androst-4-ene-3,17-dione monooxygenase
for references in articles please use BRENDA:EC1.14.99.12
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.99 Miscellaneous
1.14.99.12 androst-4-ene-3,17-dione monooxygenase
IUBMB Comments
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.
The enzyme appears in viruses and cellular organisms
- 1.14.99.12
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putida
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hydroxylases
- toluene
- catechol
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alpha-hydroxylase
showSynonyms
androstenedione monooxygenase, androst-4-ene-3,17-dione 17-oxidoreductase, androst-4-ene-3,17-dione hydroxylase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-androstene-3,17-dione monooxygenase
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androst-4-ene-3,17-dione 17-oxidoreductase
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androst-4-ene-3,17-dione hydroxylase
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androstene-3,17-dione hydroxylase
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androstenedione monooxygenase
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oxygenase, androstenedione mono-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
androstenedione + reduced acceptor + O2 = testololactone + acceptor + H2O
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
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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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
COMMENTARY
37256-74-9
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
androst-4-ene-3,17-dione + AH2 + O2
14alpha-hydroxyandrost-4-ene-3,17-dione + 14alpha,17beta-dihydroxyandrost-4-en-3-one + 7alpha,17beta-dihydroxyandrost-4-en-3-one + A + H2O
androst-4-ene-3,17-dione + AH2 + O2
14alpha-hydroxyandrost-4-ene-3,17-dione + 6beta-hydroxyandrost-4-ene-3,17-dione + A + H2O
androst-4-ene-3,17-dione + AH2 + O2
17beta-hydroxyandrost-4-en-3-one + 11beta-hydroxyandrost-4-ene-3,17-dione + 17alpha-oxa-D-homo-androst-4-ene-3,17-dione + A + H2O
androst-4-ene-3,17-dione + AH2 + O2
17beta-hydroxyandrost-4-en-3-one + 14alpha-hydroxyandrost-4-ene-3,17-dione + 11alpha-hydroxyandrost-4-ene-3,17-dione + 15beta,17beta-dihydroxyandrost-4-en-3-one + 11alpha,17beta-dihydroxyandrost-4-en-3-one + 15alpha,17beta-dihydroxyandrost-4-en-3-one + A + H2O
androst-4-ene-3,17-dione + AH2 + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + A + H2O
androst-4-ene-3,17-dione + NADPH + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + NADP+ + H2O
androst-4-ene-3,17-dione + AH2 + O2
14alpha-hydroxyandrost-4-ene-3,17-dione + 14alpha,17beta-dihydroxyandrost-4-en-3-one + 7alpha,17beta-dihydroxyandrost-4-en-3-one + A + H2O
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
14alpha-hydroxyandrost-4-ene-3,17-dione + 14alpha,17beta-dihydroxyandrost-4-en-3-one + 7alpha,17beta-dihydroxyandrost-4-en-3-one + A + H2O
Mucor hiemalis MRC 70325
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
14alpha-hydroxyandrost-4-ene-3,17-dione + 6beta-hydroxyandrost-4-ene-3,17-dione + A + H2O
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Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + AH2 + O2
14alpha-hydroxyandrost-4-ene-3,17-dione + 6beta-hydroxyandrost-4-ene-3,17-dione + A + H2O
Aspergillus wentii MRC 200316
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
17beta-hydroxyandrost-4-en-3-one + 11beta-hydroxyandrost-4-ene-3,17-dione + 17alpha-oxa-D-homo-androst-4-ene-3,17-dione + A + H2O
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Substrates: -
Products: -
Products: -
?
androst-4-ene-3,17-dione + AH2 + O2
17beta-hydroxyandrost-4-en-3-one + 11beta-hydroxyandrost-4-ene-3,17-dione + 17alpha-oxa-D-homo-androst-4-ene-3,17-dione + A + H2O
Aspergillus tamarii MRC 72400
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
17beta-hydroxyandrost-4-en-3-one + 14alpha-hydroxyandrost-4-ene-3,17-dione + 11alpha-hydroxyandrost-4-ene-3,17-dione + 15beta,17beta-dihydroxyandrost-4-en-3-one + 11alpha,17beta-dihydroxyandrost-4-en-3-one + 15alpha,17beta-dihydroxyandrost-4-en-3-one + A + H2O
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
17beta-hydroxyandrost-4-en-3-one + 14alpha-hydroxyandrost-4-ene-3,17-dione + 11alpha-hydroxyandrost-4-ene-3,17-dione + 15beta,17beta-dihydroxyandrost-4-en-3-one + 11alpha,17beta-dihydroxyandrost-4-en-3-one + 15alpha,17beta-dihydroxyandrost-4-en-3-one + A + H2O
Aspergillus candidus MRC 200634
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + A + H2O
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Substrates: enzyme levels increase after exposure of rats to di-n-butyl phthalate
Products: -
Products: -
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androst-4-ene-3,17-dione + AH2 + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + A + H2O
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Substrates: -
Products: -
Products: -
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androst-4-ene-3,17-dione + NADPH + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + NADP+ + H2O
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Substrates: -
Products: testololactone
Products: testololactone
?
androst-4-ene-3,17-dione + NADPH + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + NADP+ + H2O
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Substrates: -
Products: testololactone
Products: testololactone
?
androst-4-ene-3,17-dione + NADPH + O2
3-oxo-13,17-secoandrost-4-ene-17,13alpha-lactone + NADP+ + H2O
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Substrates: -
Products: testololactone
Products: testololactone
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
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
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Substrates: enzyme levels increase after exposure of rats to di-n-butyl phthalate
Products: -
Products: -
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
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
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
0.084
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
0.026
5alpha-androstane-17beta-ol
Rattus norvegicus
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IC50 of 0.026 mM against androstendione 16alpha-hydroxylase activity
0.046
5alpha-androstane-17beta-ol
Rattus norvegicus
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exhibits an IC50 of 0.046 mM against androstendione 6beta-hydroxylase activity
0.047
5alpha-androstane-17beta-ol
Rattus norvegicus
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IC50 of 0.047 mM against androstendione 16beta-hydroxylase activity
0.12
5alpha-androstane-3beta-ol-17-one
Rattus norvegicus
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exhibits an IC50 of 0.12 mM against androstendione 6beta-hydroxylase activity
0.14
5alpha-androstane-3beta-ol-17-one
Rattus norvegicus
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IC50 of 0.14 mM against androstendione 16beta-hydroxylase activity
0.065
5beta-androstane-17beta-ol
Rattus norvegicus
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IC50 of 0.065 mM against androstendione 16alpha-hydroxylase activity
0.11
5beta-androstane-17beta-ol
Rattus norvegicus
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exhibits an IC50 of 0.11 mM against androstendione 6beta-hydroxylase activity
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
the steroid monooxygenase also has androstenedione monooxygenase activity
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brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Itagaki, E.
Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Oxygenative lactonization of androstenedione to testololactone
J. Biochem.
99
825-832
1986
Ilyonectria destructans
brenda
Prairie, R.L.; Talalay, P.
Enzymatic formation of testololactone
Biochemistry
2
203-208
1963
Purpureocillium lilacinum
brenda
Murray, M.; Mehta, I.
Structure-activity relationships in the in vitro modulation of rat hepatic microsomal androst-4-ene-3,17,dione hydroxylase activities by derivatives of 5alpha- and 5beta-androstane
J. Steroid Biochem.
35
465-471
1999
Rattus norvegicus
brenda
Fan, L.Q.; You, L.; Brown-Borg, H.; Brown, S.; Edwards, R.J.; Corton, J.C.
Regulation of phase I and phase II steroid metabolism enzymes by PPARa activators
Toxicology
204
109-121
2004
Rattus norvegicus
brenda
Yildirim, K.; Kuru, A.; Keskin, E.; Salihoglu, A.; Bukum, N.
Biotransformation of androst-4-ene-3,17-dione by some fungi
J. Chem. Res.
41
594-597
2017
Aspergillus candidus, Aspergillus candidus MRC 200634, Aspergillus tamarii, Aspergillus tamarii MRC 72400, Aspergillus wentii, Aspergillus wentii MRC 200316, Mucor hiemalis, Mucor hiemalis MRC 70325
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brenda
EXTERNAL LINKS (specific for EC-Number 1.14.99.12)
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