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Information on EC 1.14.99.38 - cholesterol 25-monooxygenase
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1.14.99.38 cholesterol 25-monooxygenaseIUBMB Comments
Unlike most other sterol hydroxylases, this enzyme is not a cytochrome P-450. Instead, it uses diiron cofactors to catalyse the hydroxylation of hydrophobic substrates . The diiron cofactor can be either Fe-O-Fe or Fe-OH-Fe and is bound to the enzyme through interactions with clustered histidine or glutamate residues [4,5]. In cell cultures, this enzyme down-regulates cholesterol synthesis and the processing of sterol regulatory element binding proteins (SREBPs). cf. EC 1.17.99.10, cholesterol C-25 hydroxylase.
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Word Map
- 1.14.99.38
-
pregnane
-
cyp2b10
- 25-hydroxycholesterol
-
androstane
- oxysterols
-
drug-metabolizing
- phenobarbital
-
cyp2c29
- ugt1a1
-
interferon-stimulated
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cyp3a13
-
apap-induced
-
lithocholic
-
acetaminophen-induced
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pxr-mediated
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cyp2a4
-
pxr-null
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tcpobop
- medicine
The enzyme appears in viruses and cellular organisms
Synonyms
cyp3a11, ch25h, cholesterol-25-hydroxylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CH25H
cholesterol 25-hydroxylase
cholesterol 25-monooxygenase
cholesterol-25-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cholesterol + reduced acceptor + O2 = 25-hydroxycholesterol + acceptor + H2O
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
reduction
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
cholesterol,hydrogen-donor:oxygen oxidoreductase (25-hydroxylating)
Unlike most other sterol hydroxylases, this enzyme is not a cytochrome P-450. Instead, it uses diiron cofactors to catalyse the hydroxylation of hydrophobic substrates [1]. The diiron cofactor can be either Fe-O-Fe or Fe-OH-Fe and is bound to the enzyme through interactions with clustered histidine or glutamate residues [4,5]. In cell cultures, this enzyme down-regulates cholesterol synthesis and the processing of sterol regulatory element binding proteins (SREBPs). cf. EC 1.17.99.10, cholesterol C-25 hydroxylase.
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CAS REGISTRY NUMBER
COMMENTARY
60202-07-5
-
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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
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
cholesterol 25-hydroxylase has the capacity to play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein processing and ultimately leads to inhibition of gene transcription
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
genetic variability in the set of cholesterol metabolism genes: cholesterol 25-hydroxylase, cholesterol 24-hydroxylase and ATP-binding cassette transporter A1 does not influence the development of Alzheimers disease
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-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the enzyme has the capacity to synthesize an active and potent regulator of the sterol response element binding protein pathway within the cell
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
lower 25-hydroxylation enzyme activity by CYP1A2 compared to marker enzyme CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
lower 25-hydroxylation enzyme activity by CYP2C9 compared to marker enzyme CYP3A4
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-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
lower 25-hydroxylation enzyme activity by CYP2D6 compared to marker enzyme CYP3A4
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-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
production of 25-hydroxycholesterol by intact CYP3A4, most significant activity is 25-hydroxylation, which is higher than that of 4beta-hydroxylation, a marker activity of CYP3A4
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-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the reaction might be catalyzed by CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
cholesterol 25-hydroxylase has the capacity to play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein processing and ultimately leads to inhibition of gene transcription
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the enzyme has the capacity to synthesize an active and potent regulator of the sterol response element binding protein pathway within the cell
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the reaction might be catalyzed by CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
testicular macrophagers play an important role in the differentiation of Leydig cells through the secretion of 25-hydroxycholesterol
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
expression of 25-hydroxylase mRNA and production of 25-hydroxycholesterol by cultured testicular macrophages is significantly inhibited by testosterone at 0.01 mg/ml
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-
?
additional information
?
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25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
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-
?
additional information
?
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
-
-
?
additional information
?
-
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
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-
?
additional information
?
-
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
-
-
?
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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
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
cholesterol 25-hydroxylase has the capacity to play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein processing and ultimately leads to inhibition of gene transcription
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
genetic variability in the set of cholesterol metabolism genes: cholesterol 25-hydroxylase, cholesterol 24-hydroxylase and ATP-binding cassette transporter A1 does not influence the development of Alzheimers disease
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the enzyme has the capacity to synthesize an active and potent regulator of the sterol response element binding protein pathway within the cell
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
lower 25-hydroxylation enzyme activity by CYP1A2 compared to marker enzyme CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
lower 25-hydroxylation enzyme activity by CYP2C9 compared to marker enzyme CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
lower 25-hydroxylation enzyme activity by CYP2D6 compared to marker enzyme CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
production of 25-hydroxycholesterol by intact CYP3A4, most significant activity is 25-hydroxylation, which is higher than that of 4beta-hydroxylation, a marker activity of CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the reaction might be catalyzed by CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
cholesterol 25-hydroxylase has the capacity to play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein processing and ultimately leads to inhibition of gene transcription
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the enzyme has the capacity to synthesize an active and potent regulator of the sterol response element binding protein pathway within the cell
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
the reaction might be catalyzed by CYP3A4
-
-
?
cholesterol + AH2 + O2
25-hydroxycholesterol + A + H2O
-
testicular macrophagers play an important role in the differentiation of Leydig cells through the secretion of 25-hydroxycholesterol
-
-
?
additional information
?
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
-
-
?
additional information
?
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
-
-
?
additional information
?
-
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
-
-
?
additional information
?
-
-
25-hydroxycholesterol is a secondary autoxidation product derived from 3beta-hydroxy-cholest-5-ene-25-hydroperoxide, a hydroperoxide identified in air-aged cholesterol. Thermal decomposition of 3beta-hydroxy-cholest-5-ene-25-hydroperoxide gives rise to 25-hydroxycholesterol
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe
Fe2+
Fe
diiron-containing enzyme. The iron is present as Fe-O-Fe or Fe-OH-Fe and is coordinated with clusters of conserved histidine residues
Fe
diiron-containing enzyme. The iron is present as Fe-O-Fe or Fe-OH-Fe and is coordinated with clusters of conserved histidine residues
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
desmosterol
a potent inhibitor of CH25H; a potent inhibitor of CH25H; a potent inhibitor of CH25H
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
incubation with LPS derived from Escherichia coli or Salmonella enterica induces CH25H mRNA
-
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
patients with chronic obstructive pulmonary disease have increased expression of cholesterol 25-hydroxylase in the lung
brenda
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testicular, 10-day-old animals have the highest steady-state levels of message
brenda
additional information
25-hydroxycholesterol concentrations in normal human sera correlates positively with the levels of 4beta-hydroxycholesterol, but does not significantly correlate with the levels of 27-hydroxycholesterol or (24S)-hydroxycholesterol
brenda
additional information
25-hydroxycholesterol concentrations in normal human sera correlates positively with the levels of 4beta-hydroxycholesterol, but does not significantly correlate with the levels of 27-hydroxycholesterol or (24S)-hydroxycholesterol
brenda
additional information
25-hydroxycholesterol concentrations in normal human sera correlates positively with the levels of 4beta-hydroxycholesterol, but does not significantly correlate with the levels of 27-hydroxycholesterol or (24S)-hydroxycholesterol
brenda
additional information
25-hydroxycholesterol concentrations in normal human sera correlates positively with the levels of 4beta-hydroxycholesterol, but does not significantly correlate with the levels of 27-hydroxycholesterol or (24S)-hydroxycholesterol
brenda
additional information
-
quantitative enzyme expression analysis in macrophages and dendritic cells, overview
brenda