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Information on EC 1.14.99.4 - progesterone monooxygenase
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1.14.99.4 progesterone monooxygenaseIUBMB 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.
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Word Map
The enzyme appears in viruses and cellular organisms
Synonyms
cyp2g1, progesterone hydroxylase, progesterone monooxygenase, 17alpha-progesterone hydroxylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
17alpha-progesterone hydroxylase
17beta-progesterone hydroxylase
CYP2G1
progesterone hydroxylase
progesterone hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
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
37256-85-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
17alpha-methylpregn-4-ene-3,20-dione + NADPH + O2
?
-
about 4.3% the rate of the reaction with progesterone
-
-
?
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
-
?
progesterone + NADPH + H+ + O2
16alpha-hydroxyprogesterone + 2beta,16alpha-dihydroxyprogesterone + NADP+ + H2O
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-
-
?
testosterone + reduced acceptor + O2
15alpha-hydroxytestosterone + 15beta-hydroxytestosterone + 2beta-hydroxytestosterone + acceptor + H2O
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-
-
-
r
16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
-
degradation of pregnane side chains
-
?
16alpha,17alpha-oxidopregn-4-ene-3,20-dione + NADPH + O2
16alpha-hydroxyandrost-4-ene-3,17-dione
-
degradation of pregnane side chains
-
?
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+ + ?
-
degradation of pregnane side chains, about 210% the rate of the reaction with progesterone
-
?
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
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
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-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
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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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
progesterone + NADPH + H+ + O2
Testosterone acetate + NADP+ + H2O
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
-
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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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
coumarin
-
hydroxylase activity is amplifiable by coumarin, increases 50% above that found constitutively
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Urinary Bladder Neoplasms
Genomic Landscape of Experimental Bladder Cancer in Rodents and Its Application to Human Bladder Cancer: Gene Amplification and Potential Overexpression of Cyp2a5/CYP2A6 Are Associated with the Invasive Phenotype.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
-
progesterone, deoxycorticosterone, 17alpha-hydroxypregn-4-ene-3,20-dione as substrates
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
induction of enzyme by progesterone, 21-hydroxy-progesterone, testosterone, and alpha-naphthoflavone
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
Lisosan G protects the testicular 17alpha-progesterone hydroxylase activity and increases the plasma testosterone level compared to animals treated only with cisplatin
additional information
-
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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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Q4WB19_ASPFU
Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSC A1100)
497
0
57129
TrEMBL
Secretory Pathway (Reliability: 1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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
LITERATURE
nutrition
nutrition
-
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
-
enzyme plays a significant role in biotransformation of pesticides in rainbow trout
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Oryctolagus cuniculus, Ictalurus punctatus, Oncorhynchus mykiss, 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 roseochromogenus
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
Oryctolagus cuniculus, Mus musculus, 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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