Information on EC 1.14.13.22 - cyclohexanone monooxygenase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.14.13.22
-
RECOMMENDED NAME
GeneOntology No.
cyclohexanone monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cyclohexanone + NADPH + H+ + O2 = hexano-6-lactone + NADP+ + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
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oxygen ring insertion reaction
redox reaction
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reduction
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cyclohexanol degradation
Caprolactam degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
cyclohexanone,NADPH:oxygen oxidoreductase (lactone-forming)
A flavoprotein (FAD). In the catalytic mechanism of this enzyme, the nucleophilic species that attacks the carbonyl group is a peroxyflavin intermediate that is generated by reaction of the enzyme-bound flavin cofactor with NAD(P)H and oxygen [2]. This enzyme is able to catalyse a wide range of oxidative reactions, including enantioselective Baeyer-Villiger reactions [3], sulfoxidations [4], amine oxidations [5] and epoxidations [6].
CAS REGISTRY NUMBER
COMMENTARY hide
52037-90-8
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59088-27-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
low activity
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-
Manually annotated by BRENDA team
gene chnB
UniProt
Manually annotated by BRENDA team
-
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Manually annotated by BRENDA team
; inducible by cyclohexanone
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
gene chnB
UniProt
Manually annotated by BRENDA team
-
A0A1L1QK39
UniProt
Manually annotated by BRENDA team
-
A0A1L1QK39
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
-
flavoprotein that carries out the archetypical Baeyer-Villiger oxidation of a variety of cyclic ketones into lactones, size and shape of substrate binding pocket are adjustable to accommodate a diverse range of substrates
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-camphor + NADPH + O2
?
show the reaction diagram
(+)-dihydrocarvone + NADPH + O2
?
show the reaction diagram
(1aS,4aS,8aS)-8a-methylhexahydronaphthalene-1,6-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + NADP+ + H2O
show the reaction diagram
(1R)-bicyclo[2.2.1]heptane-2,5-dione + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
74.4% of the activity with cyclohexanone
-
-
?
(2R)-2-ethylcyclohexanone + NADPH + H+ + O2
(7S)-7-ethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + H+ + O2
cis-3, 7-dimethyl-2-oxepanone + NADP+ + H2O
show the reaction diagram
-
-
-
?
(2R,6S)-2,6-dimethylcyclohexanone + NADPH + O2 + H+
(3R,7S)-3,7-dimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
(2S)-2-(prop-2-en-1-yl)cyclohexanone + NADPH + H+ + O2
(7R)-7-(prop-2-en-1-yl)oxepan-2-one + NADP+ + H2O
show the reaction diagram
(3R)-3-(1-methylethenyl)cyclohexanone + NADPH + O2 + H+
(6S)-6-(1-methylethenyl)oxepan-2-one + NADP+ + H2O
show the reaction diagram
(4aR,8aS)-8a-methylhexahydronaphthalene-1,6(2H,5H)-dione + NADPH + O2
(5aR,9aS)-9a-methylhexahydrobenzo[b]oxepine-2,7-dione + (4aS,6S,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1-one + NADP+ + H2O
show the reaction diagram
(S)-dithiane sulfoxide + NADPH + O2
?
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
1,2-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
1,3-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
1,3-dithiane + NADPH + O2
(R)-1,3-dithiane-1-oxide + NADP+ + H2O
show the reaction diagram
1,4-cyclohexandione + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
1,4-dioxaspiro[4.5]decan-8-one + NADPH + H+ + O2
1,4,8-trioxa-spiro[4,6]undecan-9-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
1,4-dioxaspiro[4.5]decan-8-one + NADPH + O2 + H+
1,4,8-trioxaspiro[4.6]undecan-9-one + NADP+ + H2O
show the reaction diagram
1-oxa-2-oxocycloheptane + NADPH + O2
?
show the reaction diagram
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oxidation
-
-
?
1-phenyl-2-propanone + NADPH + O2
?
show the reaction diagram
2 thioanisole + NADPH + H+ + O2
(R)-thioanisole sulfoxide + (S)-thioanisole sulfoxide + 2 NADP+ + 2 H2O
show the reaction diagram
2,2,6-trimethylcyclohexanone + NADPH + H+ + O2
3,7,7-trimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
2,2,6-trimethylcyclohexanone + NADPH + O2 + H+
3,7,7-trimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
2-butanone + NADPH + H+ + O2
ethyl acetate + NADP+ + H2O
show the reaction diagram
2-butanone + NADPH + H+ + O2
methyl propanoate + NADP+ + H2O
show the reaction diagram
2-hexyl-cyclopentanone + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
2-hexylcyclopentanone + NADPH + H+ + O2
6-hexyl-tetrahydro-pyran-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
2-hexylcyclopentanone + NADPH + O2 + H+
6-hexyltetrahydro-2H-pyran-2-one + NADP+ + H2O
show the reaction diagram
-
-
82% conversion at 20 h
-
?
2-hydroxycyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-3-hydroxycyclopentane + NADP+ + H2O
show the reaction diagram
67.3% of the activity with cyclohexanone
-
-
?
2-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-3-hydroxycycloheptane + NADP+ + H2O
show the reaction diagram
2-hydroxyethyl methyl sulfide + NADPH + O2
2-hydroxyethyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methyl-cycloheptane + NADP+ + H2O
show the reaction diagram
2-methyl-cyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
show the reaction diagram
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methyl-cyclohexane + NADP+ + H2O
show the reaction diagram
2-methyl-cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-3-methylcyclohexane + NADP+ + H2O
show the reaction diagram
2-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-methylcycloheptane + NADP+ + H2O
show the reaction diagram
2-methylcyclohexanone + NADPH + O2 + H+
7-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-methylcyclohexyl boronic acid + NADPH + O2
2-methylcyclohexanol + BO3- + NADP+ + H2O
show the reaction diagram
-
racemic substrate
-
?
2-norbornanone + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
2-phenyl-1-ethanal + NADPH + O2
?
show the reaction diagram
2-phenylcyclohexanone + NADPH + H+ + O2
1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O
show the reaction diagram
11% of the activity with cyclohexanone
-
-
?
2-phenylcyclohexanone + NADPH + H+ + O2
3-phenyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
2-phenylcyclohexanone + NADPH + O2
1-oxa-2-oxo-3-phenylcycloheptane + NADP+ + H2O
show the reaction diagram
-
slight
-
-
?
2-phenylcyclohexanone + NADPH + O2 + H+
7-phenyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
51% conversion at 20 h
-
?
2-phenylethyl methyl sulfide + NADPH + O2
2-phenylethyl methyl sulfoxide
show the reaction diagram
-
-
-
?
2-phenylpropyl methyl sulfide + NADPH + O2
2-phenylpropyl methyl sulfoxide
show the reaction diagram
-
-
-
?
2-propylcyclohexanone + NADPH + O2 + H+
(7S)-7-propyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-thiacyclohexanone + NADPH + O2
1-oxa-2-oxo-3-thiacycloheptane + NADP+ + H2O
show the reaction diagram
-
substrate inactivates enzyme after a few turnovers
-
-
?
3,3,5-trimethylcyclohexanone + NADPH + H+ + O2
4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
3,3,5-trimethylcyclohexanone + NADPH + O2 + H+
4,6,6-trimethyloxepan-2-one + 4,4,6-trimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
91% conversion at 20 h, 1/1 isomer with 98% enantiomeric excess
-
?
3,4-dihydronaphthalen-2(1H)-one + NADPH + H+ + O2
8,9-dihydro-5H-7-oxa-benzocyclo-hepten-6-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
3,4-dihydronaphthalen-2(1H)-one + NADPH + O2 + H+
4,5-dihydro-3-benzoxepin-2(1H)-one + NADP+ + H2O
show the reaction diagram
-
-
more than 95% conversion one isomer
-
?
3,5-dimethylcyclohexanone + NADPH + H+ + O2
4,6-dimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
3-(1,3-benzodioxol-5-yl)cyclobutanone + NADPH + H+ + O2
4-(1,3-benzodioxol-5-yl)dihydrofuran-2(3H)-one + NADP+ + H2O
show the reaction diagram
3-(3,4,5-trimethoxyphenyl)cyclobutanone + NADPH + H+ + O2
4-(3,4,5-trimethoxyphenyl)dihydrofuran-2(3H)-one + NADP+ + H2O
show the reaction diagram
less than 50% conversion, 96% enantiomeric excess, (-)-product
-
-
?
3-methylcyclohexanone + NADPH + O2 + H+
(4S)-4-methyloxepan-2-one + (6R)-6-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4,4-dimethylcyclohexanone + NADPH + H+ + O2
5,5-dimethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
50-90% conversion
-
-
?
4-allyl-cyclohexanone + NADPH + O2
4-allyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-bromocyclohexanone + NADPH + O2
4-bromo-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-chlorocyclohexanone + NADPH + O2
4-chloro-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-ethoxy-cyclohexanone + NADPH + O2
4-ethoxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-ethyl-cyclohexanone + NADPH + O2
4-ethyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-ethylcyclohexanone + NADPH + O2 + H+
(5S)-5-ethyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
98% enantiomeric excess
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
4-hydroxycyclohexanone + NADPH + O2
1-oxa-2-oxo-5-hydroxycycloheptane + NADP+ + H2O
show the reaction diagram
4-iodocyclohexanone + NADPH + O2
4-iodo-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-methoxy-cyclohexanone + NADPH + O2
4-methoxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-methyl-cyclohexanone + NADPH + O2
4-methyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-methylcyclohexanone + NADPH + H+ + O2
?
show the reaction diagram
-
-
-
-
?
4-methylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-methylcycloheptane + NADP+ + H2O
show the reaction diagram
4-methylcyclohexanone + NADPH + O2 + H+
(5S)-5-methyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
98% enantiomeric excess
-
?
4-n-propyl-cyclohexanone + NADPH + O2
4-n-propyl-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
4-phenylcyclohexanone + NADPH + H+ + O2
5-phenyloxepan-2-one + NADP+ + H2O
show the reaction diagram
less than 50% conversion, 97% enantiomeric excess, (-)-product
-
-
?
4-tert-butylcyclohexanone + NADPH + H+ + O2
5-t-butyl-2-oxepanone + NADP+ + H2O
show the reaction diagram
-
-
-
?
4-tert-butylcyclohexanone + NADPH + O2
1-oxa-2-oxo-5-tert-butylcycloheptane + NADP+ + H2O
show the reaction diagram
-
slight
-
-
?
4-tert-butylcyclohexanone + NADPH + O2 + H+
(5S)-5-tert-butyloxepan-2-one + NADP+ + H2O
show the reaction diagram
-
-
88% conversion at 20 h, 99% enantiomeric excess
-
?
4a-methyltetrahydro-1aH-naphtho[1,8a-b]oxirene-2,5(3H,6H)-dione + NADPH + O2
(1R,3S,7S)-7-methyl-2,8-dioxatricyclo[5.5.0.01,3]dodecane-4,9-dione + NADP+ + H2O
show the reaction diagram
acetophenone + NADPH + H+ + O2
?
show the reaction diagram
allyl methyl sulfide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + H+ + O2
?
show the reaction diagram
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
(1R,5S)-3-oxabicyclo-[3.3.0]oct-6-en-3-one + (1S,5R)-2-oxabicyclo-[3.3.0]oct-6-en-3-one + NADP+ + H2O
show the reaction diagram
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one + NADP+ + H2O
show the reaction diagram
63% of the activity with cyclohexanone
-
-
?
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
show the reaction diagram
butanal + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
cis-hex-2-enyl phenyl selenide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
cuprizone + NADPH + O2
?
show the reaction diagram
cyclobutanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
show the reaction diagram
cyclobutanone + NADPH + H+ + O2
?
show the reaction diagram
cyclobutanone + NADPH + H+ + O2
dihydrofuran-2(3H)-one + NADP+ + H2O
show the reaction diagram
65% of the activity with cyclohexanone
-
-
?
cyclobutanone + NADPH + O2
1-oxa-2-oxo-cyclopentane + NADP+ + H2O
show the reaction diagram
cyclobutyl methyl ketone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
17.5% of the activity with cyclohexanone
-
-
?
cyclodecanone + NADPH + H+ + O2
1-oxa-2-oxo-cycloundecane + NADP+ + H2O
show the reaction diagram
cyclodecanone + NADPH + O2
1-oxa-2-oxocycloendecane + NADP+ + H2O
show the reaction diagram
-
low activity
-
-
?
cycloheptanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
show the reaction diagram
cycloheptanone + NADPH + O2
1-oxa-2-oxo-cyclooctane + NADP+ + H2O
show the reaction diagram
cyclohexan-1,2-dione + NADPH + O2
1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O
show the reaction diagram
cyclohexan-1,4-dione + NADPH + O2
1-oxa-2,5-dioxo-cycloheptane + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
6-hexanolide + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
epsilon-caprolactone + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
show the reaction diagram
cyclohexyl methyl ketone + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
15.7% of the activity with cyclohexanone
-
-
?
cyclohexyl methyl sulfide + NADPH + O2
cyclohexyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
cyclooctanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
show the reaction diagram
cyclooctanone + NADPH + O2
1-oxa-2-oxo-cyclononane + NADP+ + H2O
show the reaction diagram
cyclopentanone + NADPH + H+ + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
show the reaction diagram
cyclopentanone + NADPH + H+ + O2
?
show the reaction diagram
cyclopentanone + NADPH + O2
1-oxa-2-oxo-cyclohexane + NADP+ + H2O
show the reaction diagram
cyclopentyl methyl sulfide + NADPH + O2
cyclopentyl methyl sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
?
D-fenchone + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
delta-thiovalerolactone + NADPH + O2
?
show the reaction diagram
-
substrate inactivates enzyme after a few turnovers
-
-
ir
dihydrocarvone + NADPH + O2
?
show the reaction diagram
dithiane + NADPH + H+ + O2
(R)-dithiane sulfoxide + NADP+ + H2O
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
?
epsilon-thiocaprolactone + NADPH + O2
?
show the reaction diagram
-
substrate inactivates enzyme after a few turnovers
-
-
ir
ethyl 4-oxocyclohexanecarboxylate + NADPH + H+ + O2
ethyl 7-oxooxepane-4-carboxylate + NADP+ + H2O
show the reaction diagram
less than 50% conversion, 98% enantiomeric excess, (-)-product
-
-
?
ethyl p-tolyl sulfide + NADPH + O2
(S)-ethyl p-tolyl sulfoxide + NADP+ + H2O
show the reaction diagram
ethylene monothiocarbonate + NADPH + O2
?
show the reaction diagram
-
substrate inactivates enzyme after a few turnovers
-
-
?, ir
gamma-thiobutyrolactone + NADPH + O2
?
show the reaction diagram
-
substrate inactivates enzyme after a few turnovers
-
-
ir
iodide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
isopropyl methyl sulfide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
show the reaction diagram
n-butyl methyl sulfide + NADPH + O2
?
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
n-butylboronic acid + NADPH + O2
n-butanol + BO3- + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
N-methylbenzylamine + NADPH + O2
N-benzyl-N-methylhydroxylamine + NADP+ + H2O
show the reaction diagram
n-octylboronic acid + NADPH + O2
n-octanol + BO3- + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
norcamphor + NADPH + O2
?
show the reaction diagram
norcamphor + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
74.8% of the activity with cyclohexanone
-
-
?
octahydronaphthalen-1(2H)-one + NADPH + H+ + O2
octahydro-benzo[b]oxepin-2-one + octahydro-benzo[c]oxepin-1-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
octahydronaphthalen-1(2H)-one + NADPH + O2 + H+
octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one + NADP+ + H2O
show the reaction diagram
-
-
100% conversion two isomers octahydro-1-benzoxepin-2(3H)-one + octahydro-2-benzoxepin-1(3H)-one with ratio 2/1
-
?
octahydronaphthalen-2(1H)-one + NADPH + H+ + O2
cis-octahydro-benzo[c]oxepin-3-one + trans-octahydro-benzo[c]oxepin-3-one + cis-octahydro-7-oxa-benzocyclohepten-6-one + NADP+ + H2O
show the reaction diagram
-
-
-
?
octahydronaphthalen-2(1H)-one + NADPH + O2 + H+
octahydro-3-benzoxepin-2(1H)-one + octahydro-2-benzoxepin-3(1H)-one + NADP+ + H2O
show the reaction diagram
-
-
66% conversion at 20 h, octahydro-2-benzoxepin-3(1H)-one is the major product
-
?
octyl methyl sulfide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
phenyl allyl selenide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
phenyl allyl sulfide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
phenyl methyl selenide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
phenyl propargyl selenide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
phenylacetone + NADPH + H+ + O2
?
show the reaction diagram
phenylboronic acid + NADPH + O2
phenol + BO3- + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
S-gamma-thiobutyrolactone + NADPH + O2
?
show the reaction diagram
-
substrate irreversibly inactivates enzyme after a few turnovers
-
-
?
syn-7-benzyloxymethyl-2-norbonen-5-one + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
tert-butyl ethyl sulfide + NADPH + O2
?
show the reaction diagram
-
low activity
-
-
?
tert-butyl methyl sulfide + NADPH + O2
?
show the reaction diagram
tert-butyl vinyl sulfide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
thiane + NADPH + O2
?
show the reaction diagram
thiane sulfoxide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
thioanisole + NADPH + H+ + O2
?
show the reaction diagram
trans-hex-2-enyl phenyl selenide + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
triethylphosphite + NADPH + O2
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
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
(S)-dithiane sulfoxide + NADPH + O2
?
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
1-oxa-2-oxocycloheptane + NADPH + O2
?
show the reaction diagram
-
oxidation
-
-
?
4-hydroxy-cyclohexanone + NADPH + O2
4-hydroxy-hexano-6-lactone + NADP+ + H2O
show the reaction diagram
bicyclo[3.2.0]hept-2-en-6-one + NADPH + O2
?
show the reaction diagram
cyclohexan-1,2-dione + NADPH + O2
1-oxa-2,3-dioxo-cycloheptane + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
cyclohexan-1,4-dione + NADPH + O2
1-oxa-2,5-dioxo-cycloheptane + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
cyclohexanone + NADPH + H+ + O2
epsilon-caprolactone + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + H+ + O2
hexano-6-lactone + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
1-oxa-2-oxocycloheptane + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
epsilon-caprolactone + NADP+ + H2O
show the reaction diagram
cyclohexanone + NADPH + O2
hexano-6-lactone + NADP+ + H2O
show the reaction diagram
dithiane + NADPH + H+ + O2
(R)-dithiane sulfoxide + NADP+ + H2O
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
?
methyl phenyl sulfide + NADPH + H+ + O2
(R)-methyl phenyl sulfoxide + NADP+ + H2O
show the reaction diagram
n-butyl methyl sulfide + NADPH + O2
?
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
tert-butyl methyl sulfide + NADPH + O2
?
show the reaction diagram
-
recombinant enzyme in E. coli or Saccharomyces cerevisiae
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-deaza-FAD
-
reactivates apoenzyme
6-Methyl-FAD
-
reactivates apoenzyme
9-Aza-FAD
-
reactivates apoenzyme
flavin
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
-
iron-hem dependent enzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,3-dithiane
-
substrate inhibition
2-Thiacyclohexanone
-
substrate inactivates enzyme after a few turnovers
2-Thiocyclohexanone
-
-
5,5'-dithiobis(2-nitrobenzoate)
5-deaza-FAD
-
competitive
arsenate
-
-
Bathocuproine
Cu2+
-
completely
cyclohexanone
-
substrate inhibition
delta-thiovalerolactone
-
substrate inactivates enzyme after a few turnovers
diethyl dicarbonate
-
complete inhibition
ethylene monothiocarbonate
-
substrate inactivates enzyme after a few turnovers
iodoacetamide
NADP+
p-hydroxymercuribenzoate
Quinacrine
-
-
S-gamma-Thiobutyrolactone
-
substrate inactivates enzyme after a few turnovers
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7-Chloro-8-demethyl-FAD
-
reactivates apoenzyme
additional information
-
the enzyme is inducible by cyclohexanone
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
(+)-Camphor
-
-
0.045
1,3-dithiane
-
pH 8.6, 25C
0.33
1-Phenyl-2-propanone
-
-
0.5
2-butanone
-
pH 7.0, 25C
0.12
2-hydroxycyclobutanone
pH 8.0, 25C
0.0093 - 0.0112
2-Hydroxycyclohexanone
0.012
2-methylcyclohexanone
-
-
0.07
2-methylcyclohexyl boronic acid
-
-
0.35
2-Phenyl-1-ethanal
-
-
0.33
2-phenylcyclohexanone
pH 8.0, 25C
0.01
3-thiacyclohexanone
-
substrate inactivates enzyme after a few turnovers
0.39
4-Hydroxycyclohexanone
-
-
0.009 - 0.016
4-methylcyclohexanone
0.021
4-thiacyclohexanone
-
-
5 - 13
acetophenone
0.0007 - 0.0014
Bicyclo[3.2.0]hept-2-en-6-one
0.025
Butanal
-
-
0.0096
cis-hex-2-enyl phenyl selenide
-
-
0.0035
Cuprizone
-
-
0.007
Cyclobutanone
pH 8.0, 25C
0.2 - 0.88
Cycloheptanone
0.143 - 0.17
Cyclohexan-1,2-dione
0.19
Cyclohexan-1,4-dione
-
-
0.00048 - 0.04
cyclohexanone
1.03 - 1.8
Cyclooctanone
0.02 - 4.66
Cyclopentanone
0.64
dihydrocarvone
-
-
0.22
ethyl p-tolyl sulfide
-
-
2.5
Iodide
-
-
0.009
n-Butylboronic acid
-
-
0.0025
n-Octylboronic acid
-
-
0.006 - 0.02
NADPH
0.14
Norcamphor
-
-
0.1
O2
-
below
0.03
Phenyl allyl selenide
-
-
0.11
Phenyl allyl sulfide
-
-
0.044
Phenyl methyl selenide
-
-
0.128
phenyl propargyl selenide
-
-
0.2 - 3
phenylacetone
0.043
phenylboronic acid
-
-
0.024
Thiane
0.178
Thiane sulfoxide
-
-
1
thioanisole
-
pH 7.0, 25C
0.0068
trans-hex-2-enyl phenyl selenide
-
-
0.36
triethyl phosphite
-
-
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.16 - 0.47
2-butanone
4.5
2-hydroxycyclobutanone
pH 8.0, 25C
8.4
2-methylcyclohexyl boronic acid
-
-
0.73
2-phenylcyclohexanone
pH 8.0, 25C
0.1 - 0.4
acetophenone
2 - 13.4
Bicyclo[3.2.0]hept-2-en-6-one
0.683
cis-hex-2-enyl phenyl selenide
-
-
2 - 6.8
Cyclobutanone
4.3
Cycloheptanone
pH 8.0, 25C
2 - 57.4
cyclohexanone
0.68
Cyclooctanone
pH 8.0, 25C
1 - 5.9
Cyclopentanone
0.24
delta-thiovalerolactone
-
substrate inactivates enzyme after a few turnovers
0.227
epsilon-thiocaprolactone
-
substrate inactivates enzyme after a few turnovers
2.38
ethylene monothiocarbonate
-
substrate inactivates enzyme after a few turnovers
0.683
gamma-thiobutyrolactone
-
substrate inactivates enzyme after a few turnovers
9.75
phenyl propargyl selenide
-
-
1
phenylacetone
2 - 3
thioanisole
0.917
trans-hex-2-enyl phenyl selenide
-
-
additional information
additional information
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
2-butanone
-
pH 7.0, 25C
38
2-hydroxycyclobutanone
pH 8.0, 25C
2.3
2-phenylcyclohexanone
pH 8.0, 25C
0.02 - 0.03
acetophenone
920
Cyclobutanone
pH 8.0, 25C
4.9
Cycloheptanone
pH 8.0, 25C
238 - 667
cyclohexanone
0.7
Cyclooctanone
pH 8.0, 25C
1.3 - 100
Cyclopentanone
0.3 - 5
phenylacetone
3
thioanisole
-
pH 7.0, 25C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
15
1,3-dithiane
-
pH 8.6, 25C
2
2-Thiocyclohexanone
-
-
0.062
5-deaza-FAD
-
-
2.9
delta-thiovalerolactone
-
-
2
ethylene monothiocarbonate
-
-
0.038 - 0.39
NADP+
2
S-gamma-Thiobutyrolactone
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.4
-
substrate cyclohexanone, induced (1.0 mM isopropylthiogalactoside) cell culture extracts, modified Riesenberg medium, 30C
0.5
-
substrate cyclohexanone, induced (1.0 mM isopropylthiogalactoside) cell culture extracts, BHI medium, 30C
0.85
-
mutant W492A, cyclohexanone, 50 mM Tris-HCl buffer (pH 9.0), 0.1 mM NADPH, 25C
1.4
-
H163Q mutant enzyme
3.57
with cyclohexanone as substrate, pH 7.5
3.68
-
with cyclohexanone as substrate, pH 7.5
3.75
with cyclohexanone as substrate, pH 7.5
5.4
-
H96Q mutant enzyme
6
-
wild type enzyme, cyclohexanone, 50 mM Tris-HCl buffer (pH 9.0), 0.1 mM NADPH, 25C
6.8
substrate cyclohexanone, pH 8.0, 25C
8 - 10
-
partially purified enzyme, substrate 4-methylcyclohexanone
9.1
-
purified recombinant enzyme, substrate bicyclo[3.2.0]hept-2-en-6-one
9.2
-
purified native enzyme, substrate bicyclo[3.2.0]hept-2-en-6-one
9.9
-
purified enzyme
14
-
purified recombinant His-tagged enzyme expressed in yeast
15
-
purified native enzyme
15.9
-
wild type enzyme
19.9
-
purified recombinant His-tagged enzyme expressed in E. coli
21
-
purified enzyme
24.75
purified His-tagged recombinant enzyme
678
-
purified enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 10.1
-
broad, isozyme type 2
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10.5
-
no activity below pH 5.5 and above pH 10.5 at 30C
6 - 10.5
-
pH 6.0: about 40% of activity maximum with isozymes type 1 and type 2, pH 10.5: about 10% of activity maximum with isozyme type 1, about 60% of activity maximum with isozyme type 2
6 - 11
-
at pH 6.0 and 11.0: about 10% of activity maximum
7 - 8.5
70% of maximal activity at pH 7.0 within this range, His-tagged recombinant enzyme
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50000
-
gel filtration
51000
-
1 * 51000, SDS-PAGE
53000
-
low speed sedimentation without reaching equilibrium
54000
1 * 61900, calculated, 1 * 54000, SDS-PAGE
56000
-
native PAGE
59000
-
low speed sedimentation without reaching equilibrium
60800
-
wild-type, electrospray mass spectrometry
61600
-
mass spectrometry
61620
-
recombinant His-tagged enzyme expressed in E. coli
61670
-
recombinant His-tagged enzym