Information on EC 1.14.99.24 - steroid 9alpha-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.99.24
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RECOMMENDED NAME
GeneOntology No.
steroid 9alpha-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
pregna-4,9(11)-diene-3,20-dione + AH2 + O2 = 9,11alpha-epoxypregn-4-ene-3,20-dione + A + H2O
show the reaction diagram
A flavoprotein; An enzyme system involving a flavoprotein (FMN) and two iron-sulfur proteins
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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
steroid,hydrogen-donor:oxygen oxidoreductase (9-epoxidizing)
An enzyme system involving a flavoprotein (FMN) and two iron-sulfur proteins.
CAS REGISTRY NUMBER
COMMENTARY hide
82869-33-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
KCTC 1122, ATCC 6842
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Manually annotated by BRENDA team
genes kshA or Rv3526, and kshB or Rv3571
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Manually annotated by BRENDA team
genes kshA or Rv3526, and kshB or Rv3571
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Manually annotated by BRENDA team
strain M117
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Manually annotated by BRENDA team
strain KCTC 1062, synonym Nocardia erythropolis ATCC 25544
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Manually annotated by BRENDA team
strain KCTC 1062, synonym Nocardia erythropolis ATCC 25544
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Manually annotated by BRENDA team
strain KCTC 1061, synonym Nocardia erythropolis ATCC 17895
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Manually annotated by BRENDA team
strain KCTC 1061, synonym Nocardia erythropolis ATCC 17895
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Manually annotated by BRENDA team
strain IOC-77
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
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
1,4-androstadiene-3,17-dione + 2 O2 + 2 H+
9-hydroxy-1,4-androstadiene-3,17-dione + H2O2
show the reaction diagram
4,9(11)-pregnadiene-3,20-dione + NADH + O2
9,11alpha-epoxypregn-4-ene-3,20-dione + NAD+ + H2O
show the reaction diagram
4-androsten-3,17-dione + AH2 + O2
?
show the reaction diagram
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?
4-androstene-3,17-dione + NADH + O2
9alpha-hydroxy-4-androstene-3,17-dione + NAD+ + H2O
show the reaction diagram
9(11)-dehydro-17alpha-methyl-testosterone + NADH + O2
9alpha,11alpha-oxido-17beta-hydroxy-17alpha-methyl-4-androstene-3-one + 9alpha,11alpha-oxido-17beta-hydroxy-17alpha-methyl-1,4-androstadiene-3-one + NAD+ + H2O
show the reaction diagram
progesterone + AH2 + O2
9alpha-hydroxyprogesterone + A + 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
1,4-androstadiene-3,17-dione + 2 O2 + 2 H+
9-hydroxy-1,4-androstadiene-3,17-dione + H2O2
show the reaction diagram
4,9(11)-pregnadiene-3,20-dione + NADH + O2
9,11alpha-epoxypregn-4-ene-3,20-dione + NAD+ + H2O
show the reaction diagram
progesterone + AH2 + O2
9alpha-hydroxyprogesterone + A + H2O
show the reaction diagram
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reaction with whole cells in a bioreactor
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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higher hydroxylation obtained by increasing magnesium ion concentration with a maximum of stimulation at 20 mM or more
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,2'-bipyridine
8-hydroxyquinoline
Cd(CH3COO)2
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80% inhibition
CuSO4
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100% inhibition
Hg(CH3COO)2
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33% inhibition
Metyrapone
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o-phenanthroline
potassium cyanide
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60% inhibition
Sodium azide
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100% inhibition
Sodium cyanide
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
dimethyl sulfoxide
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reaction rate 111%
ethanol
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presence of ethanol enhances the hydroxylation by resting non-induced cells
methanol
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reaction rate 111%
N,N-Dimethylformamide
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reaction rate 111%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.18
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NADH reductase component
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8
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entrapped cells
9
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free cells
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10
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6 - 9.5
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entrapped cells
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20 - 30
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entrapped cells
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.46
sequence calculation
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
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NADH reductase component, SDS-PAGE
120000
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hydroxylase system composed of 3 proteins, protein III, comparative gel filtration
214000
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hydroxylase system composed of 3 proteins, protein II, comparative gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
protein II and protein III are oxygen-labile
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438294
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-100°C, enzyme activity in clear supernatant frozen in liquid nitrogen is stable for more than 1 year
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-20°C, free cells retain the original hydroxylation activity for at least 1 month
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NADH reductase component
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partially
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recombinant enzyme from Escherichia coli by immobilized metal affinity and ion exchange chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequenc determination, expression in Escherichia coli strain BL21
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DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree
genes kshA or Rv3526, and kshB or Rv3571
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
synthesis
additional information