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Information on EC 1.14.99.4 - progesterone monooxygenase for references in articles please use BRENDA:EC1.14.99.4
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EC Tree
IUBMB Comments 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.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
17alpha-progesterone hydroxylase, 17beta-progesterone hydroxylase, CYP2G1, cytochrome P-450/monooxygenase, FMO, progesterone hydroxylase,
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17alpha-progesterone hydroxylase
17beta-progesterone hydroxylase
cytochrome P-450/monooxygenase
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17alpha-progesterone hydroxylase
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17alpha-progesterone hydroxylase
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17beta-progesterone hydroxylase
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17beta-progesterone hydroxylase
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CYP2G1
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progesterone hydroxylase
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progesterone hydroxylase
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progesterone hydroxylase
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progesterone + reduced acceptor + O2 = testosterone acetate + acceptor + H2O
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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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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16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
17alpha-hydroxypregn-4-ene-3,20-dione + NADPH + O2
androst-4-ene-3,17-dione + NADP+ + ?
17alpha-methylpregn-4-ene-3,20-dione + NADPH + O2
?
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about 4.3% the rate of the reaction with progesterone
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?
5alpha-dihydrotestosterone + NADPH + O2
?
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?
androstenedione + NADPH + O2
?
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?
deoxycorticosterone + NADPH + O2
testosterone + NADP+ + ?
estradiol + NADPH + O2
?
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?
pregna-4,16-diene-3,20-dione + NADPH + O2
androst-4-ene-3,17-dione
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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
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
testosterone + NADPH + O2
6beta-hydroxytestosterone + NADP+ + H2O
additional information
?
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16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
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degradation of pregnane side chains
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?
16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
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degradation of pregnane side chains
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?
17alpha-hydroxypregn-4-ene-3,20-dione + NADPH + O2
androst-4-ene-3,17-dione + NADP+ + ?
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degradation of pregnane side chains, about 210% the rate of the reaction with progesterone
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?
17alpha-hydroxypregn-4-ene-3,20-dione + NADPH + O2
androst-4-ene-3,17-dione + NADP+ + ?
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degradation of pregnane side chains, about 210% the rate of the reaction with progesterone
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?
deoxycorticosterone + NADPH + O2
testosterone + NADP+ + ?
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degradation of pregnane side chains, about 64% the rate of the reaction with progesterone
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?
deoxycorticosterone + NADPH + O2
testosterone + NADP+ + ?
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degradation of pregnane side chains, about 64% the rate of the reaction with progesterone
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
testosterone + NADPH + O2
6beta-hydroxytestosterone + NADP+ + H2O
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?
testosterone + NADPH + O2
6beta-hydroxytestosterone + NADP+ + H2O
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?
testosterone + NADPH + O2
6beta-hydroxytestosterone + NADP+ + H2O
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?
additional information
?
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cortisol, 20alpha-hydroxy-16alpha,17alpha-oxidopregn-4-ene-3,20-dione and 20beta-hydroxypregn-4-ene-3-one are no substrates
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additional information
?
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cortisol, 20alpha-hydroxy-16alpha,17alpha-oxidopregn-4-ene-3,20-dione and 20beta-hydroxypregn-4-ene-3-one are no substrates
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Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
Progesterone + NADPH + O2
Testosterone acetate + NADP+ + H2O
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?
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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
cytochrome P450
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p-hydroxymercuribenzoate
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phenazine methosulfate
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coumarin
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hydroxylase activity is amplifiable by coumarin, increases 50% above that found constitutively
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7.5
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progesterone, deoxycorticosterone, 17alpha-hydroxypregn-4-ene-3,20-dione as substrates
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brenda
african green monkey, COS1 cells, DSMZ NoACC63
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brenda
channel catfish
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brenda
ACC 11011
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brenda
ACC 11011
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brenda
mouse, strain C57BL/6
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brenda
rainbow trout
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brenda
rabbit
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brenda
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brenda
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brenda
induction of enzyme by progesterone, 21-hydroxy-progesterone, testosterone, and alpha-naphthoflavone
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brenda
ATCC 13400
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brenda
pig
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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17beta-progesterone hydroxylase
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brenda
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17beta-progesterone hydroxylase
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brenda
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additional information
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Lisosan G protects the testicular 17alpha-progesterone hydroxylase activity and increases the plasma testosterone level compared to animals treated only with cisplatin
additional information
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Lisosan G protects the testicular 17alpha-progesterone hydroxylase activity and increases the plasma testosterone level compared to animals treated only with cisplatin
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Q4WB19_ASPFU
Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSC A1100)
497
0
57129
TrEMBL
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65000
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PAGE, gel filtration
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5.4 - 9
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irreversible inactivated below
438216
7 - 8
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most stable
438216
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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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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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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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nutrition
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multiple drugs, pesticides and therapeutic agents are used in aquaculturing of channel catfish, flavin-containing monooxygenase enzymatic systems can metabolize these chemicals in the fish
nutrition
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enzyme plays a significant role in biotransformation of pesticides in rainbow trout
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Rahim, M.A.; Sih, C.J.
Mechanisms of steroid oxidation by microorganisms. XI. Enzymatic cleavage of the pregnane side chain
J. Biol. Chem.
241
3615-3623
1966
Amorphotheca resinae, Ilyonectria destructans, Ilyonectria destructans ACC 11011
brenda
Schlenk, D.; Ronis, M.J.J.; Miranda, C.L.; Buhler, D.R.
Channel catfish liver monooxygenases. Immunological characterization of constitutive cytochromes P450 and the absence of active flavin-containing monooxygenases
Biochem. Pharmacol.
45
217-221
1993
Ictalurus punctatus, Oncorhynchus mykiss, Oryctolagus cuniculus, Sus scrofa
brenda
Straub, P.; Johnson, E.F.; Kemper, B.
Hydrophobic side chain requirements for lauric acid and progesterone hydroxylation at amino acid 113 in cytochrome P450 2C2, a potential determinant of substrate specificity
Arch. Biochem. Biophys.
306
521-527
1993
Chlorocebus aethiops
brenda
Straub, P.; Lloyd, M.; Johnson, E.F.; Kemper, B.
Differential effects of mutations in substrate recognition site 1 of cytochrome P450 2C2 on lauric acid and progesterone hydroxylation
Biochemistry
33
8029-8034
1994
Chlorocebus aethiops
brenda
Berrie, J.R.; Williams, R.A.D.; Smith, K.E.
Purification and characterization of progesterone hydroxylase, cytochrome P-450 from Streptomyces roseochromogenes ATCC 13400
Biochem. Soc. Trans.
25
18S
1997
Streptomyces roseochromogenes
brenda
Hua, Z.; Zhang, Q.; Su, T.; Lipinskas, T.W.; Ding, X.
cDNA cloning, heterologous expression, and characterization of mouse CYP2G1, an olfactory-specific steroid hydroxylase
Arch. Biochem. Biophys.
340
208-214
1997
Mus musculus, Oryctolagus cuniculus, Rattus norvegicus
brenda
Lenasi, H.; Breskvar, K.
Specific interactions of steroids, arylhydrocarbons and flavonoids with progesterone receptors from the cytosol of the fungus Rhizopus nigricans
J. Steroid Biochem. Mol. Biol.
91
273-284
2004
Rhizopus stolonifer
brenda
Longo, V.; Gervasi, P.; Lubrano, V.
Cisplatin induced toxicity in rat tissues: the protective effect of Lisosan G
Food Chem. Toxicol.
49
233-237
2011
Rattus norvegicus, Rattus norvegicus Wistar
brenda
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1.14.99.4 progesterone monooxygenase
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