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Information on EC 1.14.14.55 - quinine 3-monooxygenase
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1.14.14.55 quinine 3-monooxygenaseIUBMB Comments
A cytochrome P-450 (heme-thiolate) protein.
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- 1.14.14.55
- cyp2d6
- cyp1a2
-
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
CYP2C19, CYP3A, CYP3A4, CYPIIIA4, cytochrome P450 isoform, NF-25, Nifedipine oxidase, P450-PCN1, quinine 3-hydroxylase, Quinine 3-monooxygenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CYP2C19
-
-
-
-
CYP3A4
CYPIIIA4
-
-
-
-
cytochrome P450 isoform
-
-
-
-
NF-25
-
-
-
-
Nifedipine oxidase
-
-
-
-
P450-PCN1
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-
-
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quinine 3-hydroxylase
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-
-
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Quinine 3-monooxygenase
-
-
-
-
CYP3A4
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
quinine + [reduced NADPH-hemoprotein reductase] + O2 = 3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
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reduction
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
quinine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
A cytochrome P-450 (heme-thiolate) protein.
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CAS REGISTRY NUMBER
COMMENTARY
205394-96-3
-
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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
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
teniposide + [reduced NADPH-hemoprotein reductase] + O2
teniposide catechol + [oxidized NADPH-hemoprotein reductase] + ?
-
-
-
?
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
quinine is used for treatment of severe forms of Plasmodium falciparum malaria, phenotyping of two different populations, overview
-
-
?
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
-
-
-
?
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
-
-
-
-
?
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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
quinine + NADPH + O2
3-hydroxyquinine + NADP+ + H2O
-
quinine is used for treatment of severe forms of Plasmodium falciparum malaria, phenotyping of two different populations, overview
-
-
?
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
-
-
-
-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
grape seed extract
inhibition ranges from 6.4% to 26.8% dependent on the product
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green tea extract
most pronounced inhibition of CYP3A4, which ranges from 5.6% to 89.9% dependent on the product
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2-naphthoflavone
-
0.05 mM 2-naphthoflavone is inhibitory (about 60%) in the presence of low substrate concentrations (0.1 mM)
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
additional information
ginseng products have little to no effect on the activity of CYP3A4
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additional information
-
ginseng products have little to no effect on the activity of CYP3A4
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additional information
-
not inhibited by lignocaine, pyrimethamine, dapsone, chloroquine, diazepam, norfloxacin, proguanil, cycloguanil, and 4-chlorophenylbiguanide
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additional information
-
enzyme activity is not significantly altered following low or high dose of Nigeria honey
-
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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)
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
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
-
-
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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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
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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). CP3A4_HUMAN
503
2
57343
Swiss-Prot
Secretory Pathway (Reliability: 1)
B7P1N3_IXOSC
259
1
29542
TrEMBL
Secretory Pathway (Reliability: 1)
B7PSW1_IXOSC
280
1
31440
TrEMBL
Chloroplast (Reliability: 5)
B7P2B2_IXOSC
204
2
23463
TrEMBL
Secretory Pathway (Reliability: 1)
B7Q3W6_IXOSC
135
0
15185
TrEMBL
Chloroplast (Reliability: 3)
E0VSD4_PEDHC
529
0
61663
TrEMBL
other Location (Reliability: 2)
B7P0T0_IXOSC
202
1
23253
TrEMBL
other Location (Reliability: 2)
B7P474_IXOSC
185
0
21199
TrEMBL
other Location (Reliability: 2)
B7QD99_IXOSC
209
1
24137
TrEMBL
other Location (Reliability: 3)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A6986AG
-
single nucleotide polymorphism responsible for different CYP3A genotypes, CYP3A5 allele and genotype frequency in the populations, overview
additional information
-
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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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
genes CYP3A5 and CYP3A4, DNA sequence determination, genotyping of two different human populations revealing the CYP3A5 and the CYP3A4 genotypes
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
green tea extract use may cause significant interactions with drugs metabolized by CYP3A4. Effect on CYP3A4 varies among different brands of green tea extract, possibly due to variations in their content of the herbal product's active ingredients
medicine
plasma concentration of 4beta-hydroxycholesterol may be used as an endogenous marker of CYP3A activity
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zhao, X.J.; Yokoyama, H.; Chiba, K.; Wanwimolruk, S.; Ishizaki, T.
Identification of human cytochrome P450 isoforms involved in the hydroxylation of quinine by human liver microsomes and nine recombinant human cytochromes P450
J. Pharmacol. Exp. Ther.
279
1327-1334
1996
Homo sapiens
brenda
Zhao, X.J.; Kawashiro, T.; Ishizaki, T.
Mutual inhibition between quinine and etoposide by human liver microsomes. Evidence for cytochrome P4503A4 involvement in their major metabolic pathways
Drug Metab. Dispos.
26
188-191
1997
Homo sapiens
brenda
Zhao, X.J.; Ishizaki, T.
The in vitro hepatic metabolism of quinine in mice, rats and dogs: comparison with human liver microsomes
J. Pharmacol. Exp. Ther.
283
1168-1176
1997
Canis lupus familiaris, Homo sapiens, Mus musculus, Rattus norvegicus
brenda
Relling, M.V.; Evans, R.; Dass, C.; Desiderio, D.M.; Nemec, J.
Human cytochrome P450 metabolism of teniposide and etoposide
J. Pharmacol. Exp. Ther.
261
491-496
1992
Homo sapiens
brenda
Mirghani, R.A.; Sayi, J.; Aklillu, E.; Allqvist, A.; Jande, M.; Wennerholm, A.; Eriksen, J.; Herben, V.M.; Jones, B.C.; Gustafsson, L.L.; Bertilsson, L.
CYP3A5 genotype has significant effect on quinine 3-hydroxylation in Tanzanians, who have lower total CYP3A activity than a Swedish population
Pharmacogenet. Genomics
16
637-645
2006
Homo sapiens
brenda
Allqvist, A.; Miura, J.; Bertilsson, L.; Mirghani, R.A.
Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers
Eur. J. Clin. Pharmacol.
63
173-179
2007
Homo sapiens
brenda
Wanwimolruk, S.; Wong, K.; Wanwimolruk, P.
Variable inhibitory effect of different brands of commercial herbal supplements on human cytochrome P-450 CYP3A4
Drug Metabol. Drug Interact.
24
17-35
2009
Homo sapiens (P08684), Homo sapiens
brenda
Diczfalusy, U.; Miura, J.; Roh, H.K.; Mirghani, R.A.; Sayi, J.; Larsson, H.; Bodin, K.G.; Allqvist, A.; Jande, M.; Kim, J.W.; Aklillu, E.; Gustafsson, L.L.; Bertilsson, L.
4Beta-hydroxycholesterol is a new endogenous CYP3A marker: relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians
Pharmacogenet. Genomics
18
201-208
2008
Homo sapiens (P08684), Homo sapiens
brenda
Zhang, H.; Coville, P.F.; Walker, R.J.; Miners, J.O.; Birkett, D.J.; Wanwimolruk, S.
Evidence for involvement of human CYP3A in the 3-hydroxylation of quinine
Br. J. Clin. Pharmacol.
43
245-252
1997
Homo sapiens
brenda
Zhao, X.J.; Ishizaki, T.
Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes
Br. J. Clin. Pharmacol.
44
505-511
1997
Homo sapiens
brenda
Wanwimolruk, S.; Paine, M.F.; Pusek, S.N.; Watkins, P.B.
Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?
Br. J. Clin. Pharmacol.
54
643-651
2002
Homo sapiens
brenda
Mirghani, R.A.; Hellgren, U.; Westerberg, P.A.; Ericsson, O.; Bertilsson, L.; Gustafsson, L.L.
The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo
Clin. Pharmacol. Ther.
66
454-460
1999
Homo sapiens
brenda
Numata, M.; Fawcett, J.P.; Rosengren, R.J.; Wanwimolruk, S.
Ontogeny of hepatic microsomal 3-hydroxylation of quinine in Adelie Penguins
Comp. Biochem. Physiol. C
138
53-58
2004
Pygoscelis adeliae
brenda
Mirghani, R.A.; Yasar, U.; Zheng, T.; Cook, J.M.; Gustafsson, L.L.; Tybring, G.; Ericsson, O.
Enzyme kinetics for the formation of 3-hydroxyquinine and three new metabolites of quinine in vitro; 3-hydroxylation by CYP3A4 is indeed the major metabolic pathway
Drug Metab. Dispos.
30
1368-1371
2002
Homo sapiens
brenda
Mirghani, R.A.; Ericsson, O.; Tybring, G.; Gustafsson, L.L.; Bertilsson, L.
Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man
Eur. J. Clin. Pharmacol.
59
23-28
2003
Homo sapiens
brenda
Igbinoba, S.I.; Akanmu, M.A.; Onyeji, C.O.; Soyinka, J.O.; Owolabi, A.R.; Nathaniel, T.I.; Pullela, S.V.; Cook, J.M.
Influence of a Nigerian honey on CYP3A4 biotransformation of quinine in healthy volunteers
J. Clin. Pharm. Ther.
40
545-549
2015
Homo sapiens
brenda
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