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Information on EC 1.14.15.3 - alkane 1-monooxygenase
for references in articles please use BRENDA:EC1.14.15.3
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EC Tree 1 Oxidoreductases
1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
1.14.15 With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
1.14.15.3 alkane 1-monooxygenase
IUBMB Comments
Some enzymes in this group are heme-thiolate proteins (P-450). Also hydroxylates fatty acids in the ω-position.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
- 1.14.15.3
-
arachidonic
- 20-hete
- peroxisome
- methanotrophs
-
20-hydroxyeicosatetraenoic
- n-alkanes
-
omega-hydroxylation
- hydroxylases
- clofibrate
- trichosporium
- methylosinus
-
eicosanoids
-
epoxyeicosatrienoic
-
petroleum
- pparalpha
-
25-hydroxyvitamin
- cyp4f2
- epoxygenase
- methylococcus
- proliferators
- capsulatus
-
cyp2b10
- ch4
-
24-hydroxylase
- cyp2c8
- laurate
-
17-octadecynoic
- cyp3a11
-
omega-oxidation
- oleovorans
-
methane-oxidizing
-
hydrocarbon-degrading
- n-hexadecane
- 1-aminobenzotriazole
- rubredoxins
-
biosurfactant
-
androstane
- methylomonas
-
oil-contaminated
-
diferrous
- methylocystis
-
alkanols
- gordonia
- omega-1
-
di-iron
-
antiferromagnetically
-
dihydroxyeicosatrienoic
- suberin
- chlorzoxazone
-
cometabolic
- environmental protection
- synthesis
- drug development
- analysis
- degradation
Reaction Schemes
show+
reduced rubredoxin
+
+
2
=
+
oxidized rubredoxin
+
Synonyms
cyp4a, cyp4a11, methane monooxygenase, alkane hydroxylase, omega-hydroxylase, 1-hydroxylase, cyp4a14, cyp4a10, alkane monooxygenase, cyp153, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1-hydroxylase
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-
-
-
alkane 1-hydrolase
-
-
-
-
alkane hydroxylase
alkane mono-oxygenase
alkane monooxygenase
alkane-1-monooxygenase 1
alkane-1-monooxygenase 2
AlkB
AlkB1
AlkB2
AlkW1
AlmA
AlmA-like alkane hydroxylase
BMO
CYP153 homologue
CYP153A
CYP4 P450
CYP4A
CYP4AII
-
-
-
-
CYPIVA1
-
-
-
-
CYPIVA11
-
-
-
-
CYPIVA2
-
-
-
-
CYPIVA3
-
-
-
-
CYPIVA5
-
-
-
-
CYPIVA6
-
-
-
-
CYPIVA7
-
-
-
-
cytochrome P-450 omega-hydroxylase
cytochrome P450 alkane hydroxylase
cytochrome P450 omega hydroxylase
diiron omega-hydroxylase
fatty acid omega-hydrolase
-
-
-
-
Fatty acid omega-hydroxylase
Gpo1
hexane hydroxylase
Lauric acid omega-hydroxylase
-
-
-
-
medium-chain alkane hydroxylase
methane monooxygenase
omega hydroxylase
omega-hydrolase
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-
-
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P-450 HK omega
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-
-
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P450-HL-omega
-
-
-
-
P452
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-
-
-
Prm1ABCD
-
additional information
alkane hydroxylase
-
-
-
-
alkane monooxygenase
-
-
-
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Fatty acid omega-hydroxylase
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-
-
-
additional information
-
part of the alkane hydroxylase system containing of the membrane bound alkane 1-monooxygenase, and the soluble rubredoxin and rubredoxin reductase
additional information
-
part of the alkane hydroxylase system containing of the membrane bound alkane 1-monooxygenase, and the soluble rubredoxin and rubredoxin reductase
-
additional information
-
two genetic homologs, alkB1 and alkB2, genes are expressed at different growth phases, alkB2 expressed in early exponential phase, alkB1 expressed in late exponential phase
additional information
-
part of the alkane hydroxylase system containing of the membrane bound alkane 1-monooxygenase, and the soluble rubredoxin and rubredoxin reductase
additional information
Pseudomonas putida GPo1 / ATCC29347
-
part of the alkane hydroxylase system containing of the membrane bound alkane 1-monooxygenase, and the soluble rubredoxin and rubredoxin reductase
-
additional information
three component alkane hydroxylase complex consisting of a particulate nonheme integral membrane alkane monooxygenase (AlkB), soluble rubredoxin (AlkG), and soluble rubredoxin reductase (AlkT), at least four alkane monooxygenase gene homologs alkB1-alkB4
additional information
three component alkane hydroxylase complex consisting of a particulate nonheme integral membrane alkane monooxygenase (AlkB), soluble rubredoxin (AlkG), and soluble rubredoxin reductase (AlkT), at least four alkane monooxygenase gene homologs alkB1-alkB4
additional information
three component alkane hydroxylase complex consisting of a particulate nonheme integral membrane alkane monooxygenase (AlkB), soluble rubredoxin (AlkG), and soluble rubredoxin reductase (AlkT), at least four alkane monooxygenase gene homologs alkB1-alkB4
additional information
three component alkane hydroxylase complex consisting of a particulate nonheme integral membrane alkane monooxygenase (AlkB), soluble rubredoxin (AlkG), and soluble rubredoxin reductase (AlkT), at least four alkane monooxygenase gene homologs alkB1-alkB4
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
octane + reduced rubredoxin + O2 + 2 H+ = 1-octanol + oxidized rubredoxin + H2O
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydroxylation
-
-
-
-
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
octane oxidation
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SYSTEMATIC NAME
IUBMB Comments
alkane,reduced-rubredoxin:oxygen 1-oxidoreductase
Some enzymes in this group are heme-thiolate proteins (P-450). Also hydroxylates fatty acids in the omega-position.
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CAS REGISTRY NUMBER
COMMENTARY
9059-16-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,7-octadiene + NADH + H+ + O2
1,2-epoxy-7-octene + NAD+ + H2O
-
Substrates: epoxidation of simple, aliphatic terminal olefins
Products: -
Products: -
?
1-hexadecene + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
1-octadecene + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
2 1-octyne + 2 NADH + 2 H+ + 2 O2
1-octanoic acid + 7-octynoic acid + 2 NAD+ + 2 H2O
-
Substrates: -
Products: -
Products: -
?
2,5-dimethylhexane + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
5,8,11-eicosatrienoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
arachidonic acid + NAD(P)H + H+ + O2
20-hydroxyicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
bicyclohexane + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
-
Substrates: i.e. bicyclo[3.1.0]hexane, no distinction between the 2- and 3-positions, reaction via formation of a substrate radical that persists in the active site
Products: -
Products: -
?
cyclohexane + NADH + H+ + O2
cyclohexanol + NAD+ + H2O
-
Substrates: -
Products: -
Products: -
?
cyclopentane + NAD(P)H + H+ + O2
cyclopentanol + NAD(P)+ + H2O
-
Substrates: very poor substrate
Products: -
Products: -
?
decane + reduced rubredoxin + O2
1-decanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
decane + reduced rubredoxin + O2 + H+
1-decanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
r
dicyclopropylketone + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
Substrates: -
Products: -
Products: -
?
docosahexaenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
dodecane + reduced rubredoxin + O2
1-dodecanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
eicosapentaenoic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
-
Substrates: is less omega-hydroxylated than 5,8,11-eicosatrienoic acid and arachidonic acid
Products: -
Products: -
?
ethyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + acetaldehyde
heptadecane + reduced rubredoxin + O2
1-heptadecanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
heptanoate + NADPH + H+ + O2
?
-
Substrates: 59% activity compared to octane
Products: -
Products: -
r
hexadecane + reduced rubredoxin + O2
1-hexadecanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
hexane + reduced rubredoxin + O2
1-hexanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
hexane + reduced rubredoxin + O2 + H+
1-hexanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
r
hexanoate + NADPH + H+ + O2
?
-
Substrates: 25% activity compared to octane
Products: -
Products: -
r
lauric acid + [reduced NADPH-hemoprotein reductase] + O2
12-hydroxydodecanoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
Substrates: -
Products: -
Products: -
?
methane sulfonic acid + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
methyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + formaldehyde
methyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + methanol
Substrates: -
Products: -
Products: -
?
methylcyclohexane + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
methylphenylcyclopropane + reduced rubredoxin + O2
1-phenylbut-3-en-1-ol + oxidized rubredoxin + H2O
-
Substrates: reaction via formation of a substrate radical that persists in the active site
Products: -
Products: -
?
monoolein + NADH + H+ + O2
18-hydroxyoctadec-9-enoic acid 2,3-dihydroxypropyl ester + NAD+ + H2O
-
Substrates: -
Products: -
Products: -
?
nitromethane + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
nonanoate + NADPH + H+ + O2
?
-
Substrates: 25% activity compared to octane
Products: -
Products: -
r
norcarane + reduced rubredoxin + O2
? + oxidized rubredoxin + H2O
-
Substrates: i.e. bicyclo[4.1.0]heptane, oxidation preferentially occurs at the less sterically hindered 3-position, reaction via formation of a substrate radical that persists in the active site
Products: -
Products: -
?
octadecane + reduced rubredoxin + O2
1-octadecanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
pentadecane + reduced rubredoxin + O2
1-pentadecanol + oxidized rubredoxin + H2O
-
Substrates: best substrate
Products: -
Products: -
?
pentane + reduced rubredoxin + O2
1-pentanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
phosphatidylethanolamine + NADH + H+ + O2
?
-
Substrates: -
Products: -
Products: -
?
propane + NADPH + H+ + O2
propan-1-ol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
stearic acid + NAD(P)H + H+ + O2
? + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
suberin + NADPH + H+ + O2
? + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
tert-amyl methyl ether + NAD(P)H + H+ + O2
tert-amyl-alcohol + NAD(P)+ + H2O + formaldehyde
tetracosane + reduced rubredoxin + O2
1-tetracosanol + oxidized rubredoxin + H2O
-
Substrates: -
Products: -
Products: -
?
(n-1)-alkanoate + NADPH + H+ + O2
(omega-1)-hydroxy-n-alkanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(n-1)-alkanoate + NADPH + H+ + O2
(omega-1)-hydroxy-n-alkanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(n-1)-alkanoate + NADPH + H+ + O2
(omega-1)-hydroxy-n-alkanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(n-1)-alkanoate + NADPH + H+ + O2
(omega-1)-hydroxy-n-alkanoate + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
(n-1)-alkanoate + NADPH + H+ + O2
(omega-1)-hydroxy-n-alkanoate + NADP+ + H2O
-
Substrates: chain length C10-C16
Products: -
Products: -
?
1,1-diethylcyclopropane + NADPH + H+ + O2
?
Pseudomonas putida GPo1 / ATCC29347
-
Substrates: -
Products: -
Products: -
?
1-octene + reduced rubredoxin + O2
1,2-epoxyoctane + oxidized rubredoxin + H2O
Substrates: epoxidation reaction catalysed by AlkB
Products: -
Products: -
?
1-octene + reduced rubredoxin + O2
1,2-epoxyoctane + oxidized rubredoxin + H2O
Pseudomonas putida GPo1 / ATCC29347
Substrates: epoxidation reaction catalysed by AlkB
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: product formation relaxes distal human pulmonary arteries
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: the rate of metabolism by CYPA11 P450 is 10-100fold less as compared to lauric acid
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
(5Z,8Z,11Z,14Z)-20-hydroxyeicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
20-hydroxyicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
20-hydroxyicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NAD(P)H + H+ + O2
20-hydroxyicosa-5,8,11,14-tetraenoic acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
butane + NADPH + H+ + O2
1-butanol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
butane + NADPH + H+ + O2
1-butanol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
cycloheptane + NAD(P)H + H+ + O2
cycloheptanol + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
cycloheptane + NAD(P)H + H+ + O2
cycloheptanol + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
cyclohexane + NAD(P)H + H+ + O2
cyclohexanol + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
cyclohexane + NAD(P)H + H+ + O2
cyclohexanol + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
cyclooctane + NAD(P)H + H+ + O2
cyclooctanol + NAD(P)+ + H2O
-
Substrates: poor substrate
Products: -
Products: -
?
cyclooctane + NAD(P)H + H+ + O2
cyclooctanol + NAD(P)+ + H2O
-
Substrates: poor substrate
Products: -
Products: -
?
ethyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + acetaldehyde
-
Substrates: -
Products: -
Products: -
?
ethyl tert-butyl ether + NAD(P)H + H+ + O2
tert-butyl-alcohol + NAD(P)+ + H2O + acetaldehyde
Pseudomonas putida GPo1 / ATCC29347
-
Substrates: -
Products: -
Products: -
?
fatty acid + NAD(P)H + H+ + O2
omega-hydroxy fatty acid + NAD(P)+ + H2O
-
Substrates: -
Products: -
Products: -
?
fatty acid + NAD(P)H + H+ + O2
omega-hydroxy fatty acid + NAD(P)+ + H2O
-
Substrates: protein from CYP52A3 has a higher affinity for fatty acids than for alkanes
Products: -
Products: -
?
fatty acid + NAD(P)H + H+ + O2
omega-hydroxy fatty acid + NAD(P)+ + H2O
-
Substrates: high affinity for short chain fatty acids
Products: -
Products: -
?
fatty acid + NAD(P)H + H+ + O2
omega-hydroxy fatty acid + NAD(P)+ + H2O
-
Substrates: protein from CYP52A3 has a higher affinity for fatty acids than for alkanes
Products: -
Products: -
?
fatty acid + NAD(P)H + H+ + O2
omega-hydroxy fatty acid + NAD(P)+ + H2O