Information on EC 1.14.14.55 - quinine 3-monooxygenase

Substrates: -
Products: -

quinine + NADPH + O2

3-hydroxyquinine + NADP+ + H2O

Substrates: -
Products: -

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

686501, 744608, 744609, 744611, 744743, 744769, 744838, 745448

Substrates: -
Products: -

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

703423, 706089

Substrates: -
Products: -

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

706089

Substrates: -
Products: -

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

Substrates: -
Products: -

show all columns Go to Natural Substrate Search

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

LITERATURE

COMMENTARY

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

quinine + NADPH + O2

3-hydroxyquinine + NADP+ + H2O

676312

Substrates: quinine is used for treatment of severe forms of Plasmodium falciparum malaria, phenotyping of two different populations, overview
Products: -

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

686501, 744608, 744609, 744611, 744743, 744769, 744838, 745448

Substrates: -
Products: -

quinine + [reduced NADPH-hemoprotein reductase] + O2

3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O

Substrates: -
Products: -

show all columns Go to Cofactor Search

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

NADPH

NADPH

NADPH

NADPH

show all columns Go to Inhibitor Search

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

2-naphthoflavone

alpha-naphthoflavone

anti-CYP2C antibodies

inhibition of 20%

anti-CYP3A4 antibodies

Chloroquin

cimetidine

diazepam

diltiazem

doxycyclin

doxycycline

erythromycin

etoposide

maximum inhibition of quinine 3-hydroxylation of 60% at 0.1 mM

grape seed extract

inhibition ranges from 6.4% to 26.8% dependent on the product

green tea extract

most pronounced inhibition of CYP3A4, which ranges from 5.6% to 89.9% dependent on the product

hydralazine

ketoconazole

ketoconazole 2R,4R enantiomer

ketoconazole 2R,4S enantiomer

ketoconazole 2S,4R enantiomer

ketoconazole 2S,4S enantiomer

midazolam

nifepidine

oleandomycin

Omeprazole

p-nitrophenol

primaquine

Quinine

maximum inhibition of etoposide 3'-demethylation of 52% at 0.1 mM

S-mephenytoin

3 entries

sulfaphenazole

inhibits more than 50% at 0.1 mM

tetracyclin

tetracycline

troleandomycin

verapamil

additional information

6 entries

2-naphthoflavone

0.05 mM 2-naphthoflavone is inhibitory (about 60%) in the presence of low substrate concentrations (0.1 mM)

2-naphthoflavone

about 20% inhibition at 0.05 mM

alpha-naphthoflavone

alpha-naphthoflavone

anti-CYP3A4 antibodies

inhibition of 92%

anti-CYP3A4 antibodies

inhibition of 72%

anti-CYP3A4 antibodies

anti-CYP3A4 antibodies

inhibition of 96%

anti-CYP3A4 antibodies

inhibition of 84%

Chloroquin

Chloroquin

diazepam

diazepam

doxycyclin

doxycyclin

doxycyclin

erythromycin

about 45% inhibition at 0.01 mM

erythromycin

ketoconazole

maximum inhibition of 88%

ketoconazole

maximum inhibition of 90% at 0.0005 mM

ketoconazole

maximum inhibition of 90% at 0.001 mM

ketoconazole

maximum inhibition of 90%

ketoconazole

i.e. KTZ, is a antifungal drug, known as an inhibitor of, especially, the CYP3A subfamily, KTZ racemate and four separate enantiomers are evaluated for their selectivity in inhibiting quinine metabolism

ketoconazole

ketoconazole

complete inhibition at 0.1 mM

744769

ketoconazole

maximum inhibition of 94%

ketoconazole

maximum inhibition of 91%

midazolam

specific inhibitor, about 25% inhibition at 0.01 mM

midazolam

about 75% inhibition at 0.05 mM

p-nitrophenol

inhibition observed but not quantified

p-nitrophenol

inhibits more than 75% at 10 mM

primaquine

primaquine

primaquine

S-mephenytoin

maximum inhibition of 74% at 0.12 mM

S-mephenytoin

S-mephenytoin

inhibits more than 70% at 0.5 mM

tetracyclin

tetracyclin

tetracyclin

troleandomycin

maximum inhibition of 93%

troleandomycin

maximum inhibition of 70% at 0.08 mM

troleandomycin

maximum inhibition of 80% at 0.1 mM

troleandomycin

maximum inhibition of 70%

troleandomycin

about 95% inhibition at 0.01 mM

troleandomycin

troleandomycin

complete inhibition at 0.08 mM

744769

troleandomycin

maximum inhibition of 85%

troleandomycin

about 10% inhibition at 0.05 mM

troleandomycin

maximum inhibition of 66%

additional information

ginseng products have little to no effect on the activity of CYP3A4

additional information

ginseng products have little to no effect on the activity of CYP3A4

additional information

not inhibited by lignocaine, pyrimethamine, dapsone, chloroquine, diazepam, norfloxacin, proguanil, cycloguanil, and 4-chlorophenylbiguanide

additional information

not inhibited by fluvoxamine

744743

additional information

not inhibited by fluvoxamine

744769

additional information

enzyme activity is not significantly altered following low or high dose of Nigeria honey

745448

show all columns Go to Activating Compound Search

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ACTIVATING COMPOUND

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

2-naphthoflavone

0.05 mM 2-naphthoflavone activates the enzyme (about 40%) in the presence of high substrate concentrations (0.5 mM)

alpha-naphthoflavone

diazepam

grape seed extract

some brands cause minor activation of CYP3A4

additional information

not activated by 0.025 mM 2-naphthoflavone

alpha-naphthoflavone

alpha-naphthoflavone

diazepam

Show Disease (2289 entries)

diazepam

show all columns Go to KM Value Search

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.00083 - 0.138

Quinine

8 entries

additional information

etoposide

3 entries

0.00083

Quinine

at pH 7.4 and 37°C

0.0227

Quinine

0.0297

Quinine

0.046

Quinine

recombinant CYP2C19

0.105

Quinine

0.106

Quinine

between 0.08 mM and 0.145 mM in 10 different human livers

0.114

Quinine

recombinant CYP3A4

0.138

Quinine

additional information

etoposide

between 0.0421 mM and 0.1151 mM

285330

additional information

kinetics

additional information

tenoposide

between 0.0197 mM and 0.0435 mM

285330

show all columns Go to Turnover Number Search

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TURNOVER NUMBER [1/s]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.00327 - 0.125

Quinine

0.00327

Quinine

recombinant CYP2C19

0.125

Quinine

recombinant CYP3A4

show all columns Go to Ki Value Search

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Ki VALUE [mM]

INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.11

midazolam

at pH 7.4 and 37°C

show all columns Go to IC50 Value Search

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IC50 VALUE [mM]

INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.097

cimetidine

Homo sapiens

at pH 7.4 and 37°C

0.127

diltiazem

Homo sapiens

at pH 7.4 and 37°C

0.017

doxycycline

Homo sapiens

at pH 7.4 and 37°C

0.061

erythromycin

Homo sapiens

at pH 7.4 and 37°C

0.197

hydralazine

Homo sapiens

at pH 7.4 and 37°C

0.000026

ketoconazole

Homo sapiens

at pH 7.4 and 37°C

0.023

ketoconazole 2R,4R enantiomer

Homo sapiens

pH 7.4, 37°C

0.014

ketoconazole 2R,4S enantiomer

Homo sapiens

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

pH 7.4, 37°C

0.01

ketoconazole racemate

Homo sapiens

pH 7.4, 37°C

0.038

nifepidine

Homo sapiens

at pH 7.4 and 37°C

0.143

oleandomycin

Homo sapiens

at pH 7.4 and 37°C

0.018

Omeprazole

Homo sapiens

at pH 7.4 and 37°C

0.02

primaquine

Homo sapiens

at pH 7.4 and 37°C

0.029

tetracycline

Homo sapiens

at pH 7.4 and 37°C

0.0083

troleandomycin

Homo sapiens

at pH 7.4 and 37°C

0.064

verapamil

Homo sapiens

at pH 7.4 and 37°C

show all columns Go to pH Optimum Search

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.4

assay at

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay at

show all columns Go to Organism Search

only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks include all textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks + FRENDAco-occurrence of enzyme names and organism names (less precise)

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

dog

brenda

mouse

brenda

brenda

rat

brenda

brenda

UniProt

brenda

744608, 744609, 744611, 744743, 744769, 744838, 745448

brenda

human

285327, 285328, 285329, 285330

brenda

show all columns Go to Source Tissue Search

only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

brenda

brenda

brenda

liver

show all columns Go to Localization Search

285327, 285328, 285329, 285330, 686501, 744608, 744609, 744611, 744769, 744838

brenda

brenda

brenda

brenda

brenda

only manually annotated data include textmining data from AMENDAenzyme occurrence in organism, localization and source tissue with reliability ranks

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

microsome

6 entries

microsome

brenda

microsome

285327, 285328, 285329, 285330, 686501, 744608, 744609, 744769

brenda

brenda

brenda

brenda

brenda

Highest Expressing Human Cell Lines

Filter by:

Cell Line Links

Gene Links

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GENERAL INFORMATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

physiological function

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

706089