Information on EC 1.14.99.4 - progesterone monooxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.99.4
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RECOMMENDED NAME
GeneOntology No.
progesterone monooxygenase
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.
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
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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
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
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
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
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
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
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
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PAGE, gel filtration
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
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
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