Information on EC 1.14.13.157 - 1,8-cineole 2-exo-monooxygenase

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The expected taxonomic range for this enzyme is: Euarchontoglires

EC NUMBER
COMMENTARY
1.14.13.157
-
RECOMMENDED NAME
GeneOntology No.
1,8-cineole 2-exo-monooxygenase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
1,8-cineole + NADPH + H+ + O2 = 2-exo-hydroxy-1,8-cineole + NADP+ + H2O
show the reaction diagram
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
1,8-cineole,NADPH:oxygen oxidoreductase (2-exo-hydroxylating)
A heme-thiolate protein (P-450). The mammalian enzyme, expressed in liver microsomes, performs a variety of oxidation reactions of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. cf. EC 1.14.13.97 (taurochenodeoxycholate 6-hydroxylase), EC 1.14.13.67 (quinine 3-monooxygenase) and EC 1.14.13.32 (albendazole monooxygenase).
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
CYP3A4
-
-
-
-
CYP3A5
-
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
physiological function
-
CYP3A4 is a major enzyme involved in the oxidation of 1,8-cineole by human liver microsomes, as there is a good correlation between CYP3A4 contents and 1,8-cineole 2-hydroxylation activities in liver microsomes of eighteen human samples and of various recombinant human P450 enzymes examined, CYP3A4 has the highest activities for 1,8-cineole 2-hydroxylation
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,4-cineole + NADPH + H+ + O2
2-exo-hydroxy-1,4-cineole + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
1,8-cineole + NADPH + H+ + O2
2-exo-hydroxy-1,8-cineole + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
1,8-cineole + NADPH + H+ + O2
2-exo-hydroxy-1,8-cineole + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
1,8-cineole + NADPH + H+ + O2
2alpha-hydroxy-1,8-cineole + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
1,8-cineole + NADPH + H+ + O2
3alpha-hydroxy-1,8-cineole + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Ketoconazole
-
significant inhibition
Ketoconazole
-
significant inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
dexamethasone
-
induces activity
Phenobarbital
-
induces activity
pregenolone-16alpha-carbonitrile
-
induces activity
pregnenolone 16alpha-carbonitrile
-
induces activity
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.45
-
1,4-cineole
-
pH 7.4, 37C
-
1.033
-
1,4-cineole
-
pH 7.4, 37C, animals treated with pregnenolone 16alpha-carbonitrile
-
1.123
-
1,4-cineole
-
pH 7.4, 37C, animals treated with dexamethasone
-
0.012
-
1,8-cineole
-
pH 7.4, 37C, formation of 2-hydroxy-1,8-cineole by isoform CYP3A4
0.019
-
1,8-cineole
-
pH 7.4, 37C, formation of 3-hydroxy-1,8-cineole by isoform CYP3A4
0.02
-
1,8-cineole
-
pH 7.4, 37C, after treatment of animals with pregenolone-16alpha-carbonitrile
0.05
-
1,8-cineole
-
pH 7.4, 37C
0.141
-
1,8-cineole
-
pH 7.4, 37C, formation of 3-hydroxy-1,8-cineole by isoform CYP3A5
0.599
-
1,8-cineole
-
pH 7.4, 37C, formation of 2-hydroxy-1,8-cineole by isoform CYP3A5
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.056
-
1,8-cineole
-
pH 7.4, 37C, formation of 3-hydroxy-1,8-cineole by isoform CYP3A4
270173
0.08
-
1,8-cineole
-
pH 7.4, 37C, formation of 2-hydroxy-1,8-cineole by isoform CYP3A4
270173
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli
-
expression in insect cells
-
expression in insect cells
-