Information on EC 1.14.99.4 - progesterone monooxygenase

for references in articles please use BRENDA:EC1.14.99.4
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

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EC NUMBER
COMMENTARY hide
1.14.99.4
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RECOMMENDED NAME
GeneOntology No.
progesterone monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
progesterone + AH2 + O2 = testosterone acetate + A + H2O
show the reaction diagram
Has a wide specificity. A single enzyme from Cylindrocarpon radicicola (EC1.14.13.54 ketosteroid monooxygenase) catalyses both this reaction and that catalysed by EC1.14.99.12 4-androstene-3,17-dione monooxygenase
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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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SYSTEMATIC NAME
IUBMB Comments
progesterone,hydrogen-donor:oxygen oxidoreductase (hydroxylating)
Has a wide specificity. A single enzyme from ascomycete the Neonectria radicicola (EC 1.14.13.54 ketosteroid monooxygenase) catalyses both this reaction and that catalysed by EC 1.14.99.12 androst-4-ene-3,17-dione monooxygenase.
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CAS REGISTRY NUMBER
COMMENTARY hide
37256-85-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
african green monkey, COS1 cells, DSMZ NoACC63
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Manually annotated by BRENDA team
channel catfish
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Manually annotated by BRENDA team
ACC 11011
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Manually annotated by BRENDA team
mouse, strain C57BL/6
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Manually annotated by BRENDA team
rainbow trout
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Manually annotated by BRENDA team
induction of enzyme by progesterone, 21-hydroxy-progesterone, testosterone, and alpha-naphthoflavone
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Manually annotated by BRENDA team
ATCC 13400
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Manually annotated by BRENDA team
pig
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Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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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
16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
show the reaction diagram
17alpha-hydroxypregn-4-ene-3,20-dione + NADPH + O2
androst-4-ene-3,17-dione + NADP+ + ?
show the reaction diagram
17alpha-methylpregn-4-ene-3,20-dione + NADPH + O2
?
show the reaction diagram
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about 4.3% the rate of the reaction with progesterone
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?
5alpha-dihydrotestosterone + NADPH + O2
?
show the reaction diagram
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?
androstenedione + NADPH + O2
?
show the reaction diagram
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?
deoxycorticosterone + NADPH + O2
testosterone + NADP+ + ?
show the reaction diagram
estradiol + NADPH + O2
?
show the reaction diagram
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?
pregna-4,16-diene-3,20-dione + NADPH + O2
androst-4-ene-3,17-dione
show the reaction diagram
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degradation of pregnane side chains, about 104% the rate of the reaction with progesterone
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?
progesterone + NADPH + O2
16alpha-hydroxyprogesterone + 2beta,16alpha-dihydroxyprogesterone + NADP+ + H2O
show the reaction diagram
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
show the reaction diagram
testosterone + NADPH + O2
6beta-hydroxytestosterone + NADP+ + H2O
show the reaction diagram
additional information
?
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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
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
show the reaction diagram
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADPH
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absolute requirement, FMN, FAD, NADH or 2-amino-6,7-dimethyl-4-hydroxy-5,6,7,8-tetrahydropteridine cannot replace NADPH as hydrogen-donor
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
methylene blue
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p-hydroxymercuribenzoate
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phenazine methosulfate
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
coumarin
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hydroxylase activity is amplifiable by coumarin, increases 50% above that found constitutively
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0076
progesterone
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0.0051
testosterone
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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progesterone, deoxycorticosterone, 17alpha-hydroxypregn-4-ene-3,20-dione as substrates
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
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PAGE, gel filtration
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.4 - 9
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irreversible inactivated below
438216
7 - 8
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most stable
438216
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
1 mg/ml albumin stabilizes crude enzyme extract for 1 month when kept frozen
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10 h dialysis of purified enzyme against 0.01 M Tris buffer, pH 7.5, 0.005 M EDTA, leads to 50% loss of activity
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EDTA affords some protection, especially for crude extracts
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preparation is highly unstable
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-6°, 85% of the enzyme activity is lost in 24 h
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0°C, 80% enzyme activity is lost in 7 days, half-life of a highly purified preparation is 12 h
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cDNA obtained by PCR, cloning into a baculoviral expression vector pVL1392, production of the enzyme in culturd insect cells and heterologous expression of CYP2G1 in rabbits and rats
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.99.4)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)