Information on EC 1.14.14.55 - quinine 3-monooxygenase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.14.55
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RECOMMENDED NAME
GeneOntology No.
quinine 3-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
quinine + [reduced NADPH-hemoprotein reductase] + O2 = 3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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-
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reduction
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-
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SYSTEMATIC NAME
IUBMB Comments
quinine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY hide
205394-96-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
mouse
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
rat
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Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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differences in the activity of both CYP3A4 and CYP3A5 in Koreans, Swedes and Tanzanians. Both 4beta-hydroxycholesterol and quinine/3-hydroxyquinine metabolic ratio show a higher CYP3A activity in women than in men
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
etoposide + NADPH + O2
3'-demethyletoposide + NADP+ + H2O
show the reaction diagram
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
show the reaction diagram
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
quinine + [reduced NADPH—hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH—hemoprotein reductase] + H2O
show the reaction diagram
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-
?
tacrolismus + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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-
-
-
?
teniposide + NADPH + O2
teniposide catechol + NADP+ + H2O
show the reaction diagram
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-
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?
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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
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
show the reaction diagram
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quinine is used for treatment of severe forms of Plasmodium falciparum malaria, phenotyping of two different populations, overview
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-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
quinine + [reduced NADPH—hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH—hemoprotein reductase] + H2O
show the reaction diagram
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-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-naphthoflavone
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alpha-naphthoflavone
anti-CYP2C antibodies
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inhibition of 20%
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anti-CYP3A4 antibodies
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Chloroquin
cimetidine
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diazepam
diltiazem
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doxycyclin
doxycycline
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erythromycin
etoposide
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maximum inhibition of quinine 3-hydroxylation of 60% at 0.1 mM
grape seed extract
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inhibition ranges from 6.4% to 26.8% dependent on the product
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green tea extract
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most pronounced inhibition of CYP3A4, which ranges from 5.6% to 89.9% dependent on the product
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hydralazine
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ketoconazole
ketoconazole 2R,4R enantiomer
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ketoconazole 2R,4S enantiomer
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ketoconazole 2S,4R enantiomer
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ketoconazole 2S,4S enantiomer
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midazolam
nifepidine
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oleandomycin
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Omeprazole
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p-nitrophenol
primaquine
Quinine
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maximum inhibition of etoposide 3'-demethylation of 52% at 0.1 mM
S-mephenytoin
sulfaphenazole
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inhibits more than 50% at 0.1 mM
tetracyclin
tetracycline
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troleandomycin
verapamil
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additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-naphthoflavone
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0.05 mM 2-naphthoflavone activates the enzyme (about 40%) in the presence of high substrate concentrations (0.5 mM)
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alpha-naphthoflavone
diazepam
grape seed extract
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some brands cause minor activation of CYP3A4
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additional information
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not activated by 0.025 mM 2-naphthoflavone
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00083 - 0.138
Quinine
additional information
etoposide
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00327 - 0.125
Quinine
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.11
midazolam
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at pH 7.4 and 37°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.097
cimetidine
Homo sapiens
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at pH 7.4 and 37°C
0.127
diltiazem
Homo sapiens
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at pH 7.4 and 37°C
0.017
doxycycline
Homo sapiens
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at pH 7.4 and 37°C
0.061
erythromycin
Homo sapiens
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at pH 7.4 and 37°C
0.197
hydralazine
Homo sapiens
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at pH 7.4 and 37°C
0.000026
ketoconazole
Homo sapiens
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at pH 7.4 and 37°C
0.023
ketoconazole 2R,4R enantiomer
Homo sapiens
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pH 7.4, 37°C
0.014
ketoconazole 2R,4S enantiomer
Homo sapiens
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pH 7.4, 37°C
0.011
ketoconazole 2S,4R enantiomer
Homo sapiens
-
pH 7.4, 37°C
0.004
ketoconazole 2S,4S enantiomer
Homo sapiens
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pH 7.4, 37°C
0.01
ketoconazole racemate
Homo sapiens
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pH 7.4, 37°C
0.038
nifepidine
Homo sapiens
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at pH 7.4 and 37°C
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0.143
oleandomycin
Homo sapiens
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at pH 7.4 and 37°C
0.018
Omeprazole
Homo sapiens
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at pH 7.4 and 37°C
0.02
primaquine
Homo sapiens
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at pH 7.4 and 37°C
0.029
tetracycline
Homo sapiens
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at pH 7.4 and 37°C
0.0083
troleandomycin
Homo sapiens
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at pH 7.4 and 37°C
0.064
verapamil
Homo sapiens
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at pH 7.4 and 37°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
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assay at
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by microsome preparation
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression of CYP3A4 in human B lymphoblastoid cell line AHH-1
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genes CYP3A5 and CYP3A4, DNA sequence determination, genotyping of two different human populations revealing the CYP3A5 and the CYP3A4 genotypes
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A6986AG
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single nucleotide polymorphism responsible for different CYP3A genotypes, CYP3A5 allele and genotype frequency in the populations, overview
additional information
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the CYP3A5 genotype has significant effect on quinine 3-hydroxylation in black Tanzanians, who have lower total CYP3A activity compared to a population of Swedish caucasians, overview
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.14.55)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)