Information on EC 1.14.14.1 - unspecific monooxygenase

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

EC NUMBER
COMMENTARY hide
1.14.14.1
-
RECOMMENDED NAME
GeneOntology No.
unspecific monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
RH + [reduced NADPH-hemoprotein reductase] + O2 = ROH + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Deamination
-
-
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desulfation
-
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epoxidation
hydroxylation
N-dealkylation
-
-
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N-oxidation
-
-
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O-dealkylation
-
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oxidation
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redox reaction
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reduction
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reduction of azo, nitro, N-oxide groups
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-
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S-dealkylation
-
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sulfoxidation
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
1,5-anhydrofructose degradation
-
-
acetone degradation I (to methylglyoxal)
-
-
acetone degradation III (to propane-1,2-diol)
-
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Aminobenzoate degradation
-
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arachidonic acid metabolism
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Arachidonic acid metabolism
-
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Biosynthesis of secondary metabolites
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bupropion degradation
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Caffeine metabolism
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Drug metabolism - cytochrome P450
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Fatty acid degradation
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Linoleic acid metabolism
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melatonin degradation I
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Metabolic pathways
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Metabolism of xenobiotics by cytochrome P450
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Microbial metabolism in diverse environments
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nicotine degradation IV
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nicotine degradation V
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Retinol metabolism
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Steroid hormone biosynthesis
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Tryptophan metabolism
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vanillin biosynthesis I
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SYSTEMATIC NAME
IUBMB Comments
substrate,NADPH-hemoprotein reductase:oxygen oxidoreductase (RH-hydroxylating or -epoxidizing)
A group of P-450 heme-thiolate proteins, acting on a wide range of substrates including many xenobiotics, steroids, fatty acids, vitamins and prostaglandins; reactions catalysed include hydroxylation, epoxidation, N-oxidation, sulfooxidation, N-, S- and O-dealkylations, desulfation, deamination, and reduction of azo, nitro and N-oxide groups. Together with EC 1.6.2.4, NADPH---hemoprotein reductase, it forms a system in which two reducing equivalents are supplied by NADPH. Some of the reactions attributed to EC 1.14.15.3, alkane 1-monooxygenase, belong here.
CAS REGISTRY NUMBER
COMMENTARY hide
62213-32-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
variant CIM-Arogya
UniProt
Manually annotated by BRENDA team
strain MTCC 6324
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-
Manually annotated by BRENDA team
strain MTCC 6324
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-
Manually annotated by BRENDA team
strain DSM13
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-
Manually annotated by BRENDA team
strain DSM13
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-
Manually annotated by BRENDA team
ATCC 20336, isozymes CYP52A13, CYP52A17
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-
Manually annotated by BRENDA team
strain P1, gene cloA
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Manually annotated by BRENDA team
strain P1, gene cloA
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
herbicide-resistant and herbicide-susceptible late watergrass populations
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Manually annotated by BRENDA team
B 276
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Manually annotated by BRENDA team
B 276
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Manually annotated by BRENDA team
corn earworm
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
sole protogynous freshwater fish found that exhibits an adult sex change from functional females to males
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Orobanche ramosa
broomrape, a root parasitic weed often in tobacco plants
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-
Manually annotated by BRENDA team
ssp. japonica, wild-type strain ZS97, gene eui or OSJNBa0095J22.13
SwissProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Sorghum sp.
-
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Manually annotated by BRENDA team
several strains, Ema genes
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Manually annotated by BRENDA team
strains R-922 and I-1529, ema genes, and genes cyp229 and cyp230
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Manually annotated by BRENDA team
strain ATCC 15439
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
synthetic construct
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
wild-type strains ATCC 24203, ATCC 96594, and ATCC 96815, and astaxanthin-overproducing recombinant strains VKPM and Y2410, gene crtS
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-camphor + O2 + H+ + NADPH
(+)-exo-5-hydroxycamphor + NADP+ + H2O
show the reaction diagram
synthetic construct
-
-
-
-
?
(-)-alpha-pinene + NADPH + O2
myrtenol + NADP+ + H2O
show the reaction diagram
(-)-alpha-pinene + NADPH + O2
pinene oxide + NADP+ + H2O
show the reaction diagram
(-)-alpha-pinene + NADPH + O2
verbenol + NADP+ + H2O
show the reaction diagram
(-)-beta-pinene + NADPH + O2
myrtanal + NADP+ + H2O
show the reaction diagram
(-)-beta-pinene + NADPH + O2
pino-carveol + NADP+ + H2O
show the reaction diagram
(R)-(+)-limonene + O2 + NADPH
(R)-cis-1,2-limonene epoxide + cis-carveol
show the reaction diagram
(S)-(-)-limonene + O2 + NADPH
(S)-trans-1,2 limonene epoxide
show the reaction diagram
(S)-nicotine + O2 + NADPH
?
show the reaction diagram
-
substrate of CYP3A4, the reaction involves electron transfer via FMN
-
-
?
10-p-nitrophenoxydecanoic acid + NADPH
?
show the reaction diagram
11-ketoprogesterone + O2 + NADPH
?
show the reaction diagram
-
-
-
?
12-methyl-myristic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
12-methyl-tetradecanoic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
13-methyl-myristic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
13-methyl-tetradecanoic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine + NADH + H+ + O2
?
show the reaction diagram
-
CYP1A2 catalyzes the first step of activation of the xenobiotic compound and its genotoxic effect, the second step is catalyzed by the sulfotransferase 1A1-1
-
-
?
2-amino-3-methylimidazo[4,5-f]quinoline + NADH + H+ + O2
?
show the reaction diagram
-
CYP1A2 catalyzes the first step of activation of the xenobiotic compound and its genotoxic effect, the second step is catalyzed by the N(O)-acetyltransferase.
-
-
?
2-hydroxy-1-(4-hydroxyphenyl)guanidine + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
3,5,4'-trimethoxy-trans-stilbene + reduced flavoprotein + O2
3-hydroxy-5,4'-dimethoxy-trans-stilbene + 3,5-dihydroxy-4'-methoxy-trans-stilbene + oxidized flavoprotein + H2O
show the reaction diagram
3,5-dimethoxy-trans-stilbene + reduced flavoprotein + O2
?
show the reaction diagram
3,7-dimethyl-1-octanol + O2 + NADPH
6-hydroxy-3,7-dimethyl-1-octanol + H2O
show the reaction diagram
-
-
-
-
?
3-cyano-7-ethoxycoumarin + O2 + NADPH
?
show the reaction diagram
3-methoxybenzoic acid + O2 + NADPH
3,4-dihydroxybenzoic acid + NADP+ + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 2, CYP53A15 converts 3-methoxybenzoic acid to 3,4-dihydroxybenzoic acid
-
-
?
3-methoxybenzoic acid + O2 + NADPH
3-hydroxybenzoic acid + NADP+ + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 1, CYP53A15 converts 3-methoxybenzoic acid to 3-hydroxybenzoic acid
-
-
?
3-[2-(N,N-diethyl-N-methylammonium)ethyl]-7-methoxy-4-methylcoumarin + O2 + NADPH
?
show the reaction diagram
-
-
-
?
4-(methylnitrosamino)-1-(3pyridyl)-1-butanone + O2 + reduced flavoprotein
?
show the reaction diagram
4-chlorostyrene + NADH + H+ + O2
4-chlorostyrene oxide + NAD+ + H2O
show the reaction diagram
4-chlorothioanisole + NADPH + H+ + O2
4-chlorothioanisole sulfoxide + NADP+ + H2O
show the reaction diagram
4-fluorothioanisole + NADPH + H+ + O2
4-fluorothioanisole sulfoxide + NADP+ + H2O
show the reaction diagram
4-methoxythioanisole + NADPH + H+ + O2
4-methoxythioanisole sulfoxide + NADP+ + H2O
show the reaction diagram
4-methylstyrene + NADH + H+ + O2
4-methylstyrene oxide + NAD+ + H2O
show the reaction diagram
-
catalyzed by StyA of Pseudomonas sp. VLB120 and electrochemical FAD reduction
-
-
?
4-tolylmethylsulfide + NADPH + H+ + O2
4-tolylmethylsulfoxide + NADP+ + H2O
show the reaction diagram
6beta-hydroxytestosterone + O2 + NADPH
?
show the reaction diagram
-
-
-
?
7-ethoxy-4-trifluoromethylcoumarin + NADPH + H+ + O2
7-hydroxy-4-trifluoromethylcoumarin + NADP+ + ?
show the reaction diagram
-
CYP1A2 cooperates with NADPH-cytochrome P450 reductase, which provides NADPH for the reaction. Interaction with their redox partner, NADPH-cytochrome P450 reductase, i.e. CPR, in a 1:1 molar ratio
-
-
?
7-ethoxy-trifluoromethylcoumarin + O2 + NADPH
?
show the reaction diagram
-
O-deethylation
-
-
?
7-ethoxycoumarin + 3 NADH + 3 H+ + O2
7-hydroxycoumarin + 3 NAD+ + ?
show the reaction diagram
-
-
-
-
?
7-ethoxycoumarin + NADPH + O2 + FAD
7-hydroxycoumarin + NADP+ + FADH2 + ?
show the reaction diagram
7-ethoxycoumarin + NADPH + O2 + reduced flavin
?
show the reaction diagram
-
-
-
-
?
7-ethoxycoumarin + O2 + NAD(P)H + cytochrome c
7-hydroxycoumarin + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
O-dealkylation
-
-
?
7-ethoxycoumarin + O2 + NADPH
7-hydroxycoumarin + NADP+ + ?
show the reaction diagram
7-ethoxycoumarin + O2 + NADPH
?
show the reaction diagram
7-ethoxyresorufin + NADPH + H+ + O2
resorufin + NADP+ + ?
show the reaction diagram
-
-
-
-
?
7-ethoxyresorufin + O2 + NADPH
?
show the reaction diagram
7-ethoxyresorufin + O2 + reduced donor
?
show the reaction diagram
-
7-ethoxyresorufin O-deethylation
-
-
?
7-hydroxycoumarin + NADPH + O2 + reduced flavin
?
show the reaction diagram
-
-
-
-
?
7-methoxy-4-(trifluoromethyl)-coumarin + O2 + NADPH
?
show the reaction diagram
7-methoxycoumarin + 3 NADH + 3 H+ + O2
7-hydroxycoumarin + 3 NAD+ + ?
show the reaction diagram
-
-
-
-
?
7-methoxycoumarin + NADPH + O2 + reduced flavin
?
show the reaction diagram
-
-
-
-
?
7-methoxyresorufin + O2 + NADPH
?
show the reaction diagram
-
-
-
-
?
7-propoxycoumarin + NADPH + O2 + reduced flavin
?
show the reaction diagram
-
-
-
-
?
acenaphthene + O2 + NAD(P)H + cytochrome c
1-acenaphthenol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
-
-
-
?
adrenic acid + NADPH + H+ + O2
?
show the reaction diagram
aflatoxin B1 + O2 + NADPH
?
show the reaction diagram
alkene + O2 + reduced flavoprotein
epoxide + H2O + oxidized flavoprotein
show the reaction diagram
alpha-ionone + O2 + NADPH
?
show the reaction diagram
-
CYP102A7, high activity
-
-
?
aminopyrene + O2 + NADPH
? + formaldehyde + NADP+ + H2O
show the reaction diagram
aminopyrine + O2 + 2 H+
? + formaldehyde + H2O
show the reaction diagram
-
-
-
-
?
amiprofos-methyl + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
anisole + O2 + NADH
?
show the reaction diagram
-
-
-
-
?
anthraquinone-1,5-disulfonic acid + O2 + NADPH
?
show the reaction diagram
anthraquinone-1,8-disulfonic acid + O2 + NADPH
?
show the reaction diagram
anthraquinone-1-sulfonic acid + O2 + NADPH
?
show the reaction diagram
anthraquinone-2,6-disulfonic acid + O2 + NADPH
?
show the reaction diagram
anthraquinone-2-sulfonic acid + O2 + NADPH
?
show the reaction diagram
arachidonic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + 19-hydroxyeicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
-
-
ratio 12:1
-
?
arachidonic acid + NADPH + H+ + O2
?
show the reaction diagram
arachidonic acid + O2 + NADPH
20-hydroxyeicosatetraenoic acid + H2O + NADP+
show the reaction diagram
arachidonic acid + O2 + NADPH + H+
18-hydroxyarachidonic acid + 14,15-epoxyeicosa-5,8,11-trienoic acid + 11,12-epoxyeicosa-5,8,14-trienoic acid + H2O + NADP+
show the reaction diagram
arachidonic acid + O2 + NADPH + H+
18-hydroxyarachidonic acid + 14,15-epoxyeicosa-5,8,11-trienoic acid + H2O + NADP+
show the reaction diagram
aryl hydrocarbons + reduced flavoprotein + O2
?
show the reaction diagram
avermectin + O2 + reduced ferredoxin
4''-oxo-avermectin + H2O + ferredoxin
show the reaction diagram
bentazon + NADPH + O2 + FAD
?
show the reaction diagram
-
ring-hydroxylation
-
-
?
benzo(a)pyrene + reduced flavoprotein + O2
?
show the reaction diagram
-
-
-
-
?
benzo(ghi)perylene + reduced flavoprotein + O2
?
show the reaction diagram
-
-
-
-
?
benzo-pyrene + NADPH + O2 + FAD
?
show the reaction diagram
-
recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
benzoic acid + O2 + NADPH
3,4-dihydroxybenzoic acid + NADP+ + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 2, CYP53A15 converts benzoic acid to 3,4-dihydroxybenzoic acid
-
-
?
benzoic acid + O2 + NADPH
4-hydroxybenzoic acid + NADP+ + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 1, CYP53A15 converts benzoic acid to 4-hydroxybenzoic acid
-
-
?
benzyl methyl sulfide + O2 + NADH
benzyl methyl sulfoxide + benzyl methyl sulfone + NAD+ + H2O
show the reaction diagram
-
50% conversion
product ratio of 78:22
-
?
bergapten + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
beta-ionone + O2 + NAD(P)H
4-hydroxy-beta-ionone + H2O + NAD(P)+
show the reaction diagram
-
-
-
-
?
beta-ionone + O2 + NADPH
4-hydroxy-beta-ionone + H2O + NADP+
show the reaction diagram
-
CYP102A7, high activity
-
-
?
beta-ionone + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q
-
-
?
bispyribac-sodium + O2 + reduced flavoprotein
?
show the reaction diagram
-
-
-
-
?
capric acid + O2 + NADPH
?
show the reaction diagram
-
-
-
?
capric acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
about 10% of the activity with palmitic acid, wild-type
-
-
?
caprylic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q
-
-
?
chlormadinone acetate + O2 + NADPH
?
show the reaction diagram
-
-
-
?
chlorotoluron + NADPH + O2 + FAD
?
show the reaction diagram
chlorotoluron + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
chlortetracycline + reduced flavoprotein + O2
11a-hydroxy-chlortetracycline + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
chlorzoxazone + O2 + NADPH
?
show the reaction diagram
-
-
-
-
?
cinnamic acid + O2 + NADPH
?
show the reaction diagram
-
-
-
?
compactin + O2 + NADPH
?
show the reaction diagram
-
-
-
?
coumarin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
cytochrome c + O2 + NADPH
?
show the reaction diagram
decanoic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
demeclocycline + reduced flavoprotein + O2
11a-hydroxy-demeclocycline + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
dibenzylfluorescein + O2 + NADPH
?
show the reaction diagram
diclofop + NADPH + O2 + FAD
?
show the reaction diagram
-
ring-hydroxylation
-
-
?
dihydronaphthalene + NADH + H+ + O2
dihydronaphthalene oxide + NAD+ + H2O
show the reaction diagram
-
catalyzed by StyA of Pseudomonas sp. VLB120 and electrochemical FAD reduction
-
-
?
dimethoxybenzene + O2 + NADH
?
show the reaction diagram
-
-
-
-
?
dimethylaniline + O2 + NADPH
?
show the reaction diagram
-
substrate of CYP3A4
-
-
?
docosahexaenoic acid + NADPH + H+ + O2
22-hydroxydocosahexaenoic acid + NADP+ + H2O
show the reaction diagram
dodecanoic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
dodecanoic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
isozyme CYP52A17, good substrate
-
-
?
doxycycline + reduced flavoprotein + O2
11a-hydroxy-doxycycline + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
eicosapentaenoic acid + NADPH + H+ + O2
20-hydroxyeicosapentaenoic acid + 19-hydroxyeicosapentaenoic acid + NADP+ + H2O
show the reaction diagram
-
-
ratio 4:3
-
?
eicosapentaenoic acid + NADPH + H+ + O2
20-hydroxyeicosapentaenoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
eicosapentaenoic acid + NADPH + H+ + O2
20-hydroxyeicosatetraenoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
eicosenoic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
elymoclavine + O2 + NADPH
paspalic acid + H2O + NADP+
show the reaction diagram
erythromycin + O2 + 2 H+
? + formaldehyde + H2O
show the reaction diagram
-
-
-
-
?
ethyl benzene + O2 + NAD(P)H + cytochrome c
1-phenylethyl alcohol + 2-phenylethyl alcohol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
recombinant enzyme
-
-
?
ethyl phenyl sulfide + O2 + NADH
ethyl phenyl sulfoxide + ethyl phenyl sulfone + NAD+ + H2O
show the reaction diagram
-
70% conversion
product ratio of 52:18
-
?
ethylbenzene + O2 + NADH
(R)-1-phenylethanol + 1-phenylethanone + NAD+ + H2O
show the reaction diagram
-
-
product ratio of 88:12
-
?
ethylmethylsulfide + NADPH + H+ + O2
ethylmethylsulfoxide + NADP+ + H2O
show the reaction diagram
farnesol + O2 + NADPH
?
show the reaction diagram
-
CYP102A1 oxidizes farnesol to three products (2,3-epoxyfarnesol, 10,11-epoxyfarnesol, and 9-hydroxyfarnesol), whereas CYP4C7 produces 12-hydroxyfarnesol as the major product. Chimeric proteins C(78-82,F87L) and C(78-82,F87L,328-330) show the most complete change in substrate selectivity from fatty acids to farnesol, and both retain superior enzyme activity with respect to CYP102A1 approximately 5times and approximately 2times greater, respectively. C(78-82,F87L,328-330) produces 12-hydroxyfarnesol as the major metabolite, as does CYP4C7
-
-
?
fenoxaprop-ethyl + O2 + reduced flavoprotein
?
show the reaction diagram
-
-
-
-
?
fenthion + O2 + NADPH
?
show the reaction diagram
fenthion-sulfoxide and fenthion-oxon, are formed by some CYPs although at very different levels, depending on the relative CYP hepatic content. Fenthion-oxon formation is favored and at low fenthion concentrations CYP2B6 and CYP1A2 are mainly involved in its formation. At higher levels, a more widespread CYP involvement is evident, as in the case of fenthion-sulfoxide
-
-
?
fenthion-sulfoxide + O2 + NADPH
fenthion-sulfone
show the reaction diagram
fluoranthene + reduced flavoprotein + O2
?
show the reaction diagram
-
-
-
-
?
fluorene + O2 + NAD(P)H + cytochrome c
9-fluorenol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
-
-
-
?
fluoxetine + O2 + 2 H+
? + formaldehyde + H2O
show the reaction diagram
-
-
-
-
?
geraniol + O2 + NADPH
8-hydroxygeraniol + 10-hydroxygeraniol + H2O
show the reaction diagram
-
-
-
-
?
geranylacetone + O2 + NADPH
9,10-epoxygeranylacetone + 11-hydroxygeranylacetone + 5,6-epoxygeranylacetone
show the reaction diagram
-
CYP102A7, high activity
-
-
?
giberellic acid GA12 + NADPH + O2
16alpha,17-epoxy GA12 + NADP+ + H2O
show the reaction diagram
-
product identification by GC-MS, the epoxid is transformed into 16,17-dihydro-16alpha,17-dihydroxy-GA4 under acidic conditions with acidic acid
-
?
giberellic acid GA4 + NADPH + H+ + O2
16alpha,17-epoxy GA4 + NADP+ + H2O
show the reaction diagram
-
the product is transformed further to 16,17-dihydro-16alpha,17-dihydroxy-GA4 in the plant, product identification by GC-MS, the epoxid is transformed into 16,17-dihydro-16alpha,17-dihydroxy-GA4 under acidic conditions with acidic acid
-
?
giberellic acid GA9 + NADPH + O2
16alpha,17-epoxy GA9 + NADP+ + H2O
show the reaction diagram
-
product identification by GC-MS, the epoxid is transformed into 16,17-dihydro-16alpha,17-dihydroxy-GA4 under acidic conditions with acidic acid
-
?
hexadecanoic acid + NADPH
?
show the reaction diagram
-
CYP102A7, highest binding affinity
-
-
?
indene + O2 + NAD(P)H + cytochrome c
indenol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
-
-
-
?
indole + O2 + NADH
(2Z)-2-(3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + (3Z)-3-(3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
isopimpinellin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
lauric acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
lauric acid + O2 + NADPH
?
show the reaction diagram
lauric acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
linoleic acid + NADPH
?
show the reaction diagram
-
CYP102A1, CYP102A2, CYP102A3 and CYP102A7. CYP102A7 with high binding affinity
-
-
?
linoleic acid + NADPH + H+ + O2
(9Z,12Z)-18-hydroxyoctadeca-9,12-dienoic acid + NADP+ + H2O
show the reaction diagram
linoleic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
isozyme CYP52A17, good substrate, isozyme CYP52A13, good substrate
-
-
?
m-xylene + O2 + NAD(P)H + cytochrome c
3-methylbenzyl alcohol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
recombinant enzyme
-
-
?
macrolide YC-17 + reduced ferredoxin + O2
methymycin + ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
macrolide YC-17 + reduced ferredoxin + O2
neomethymycin + ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
macrolide YC-17 + reduced ferredoxin + O2
novamethymycin + ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
medroxyprogesterone acetate + O2 + NADPH
?
show the reaction diagram
-
-
-
?
mefenacet + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
methanol + NADPH + O2 + FAD
formaldehyde + NADP+ + H2O + FADH2
show the reaction diagram
-
the oxidation by oxygen molar ratio of NADPH oxidized/Oz consumed, measured polarographically, is 2.0, H2O2 is produced during reoxidation of the flavoprotein by oxygen
-
-
?
methyl 10,11-epoxyfarnesoate + O2 + NADPH
?
show the reaction diagram
-
the major product of C(78-82,F87L,328-330) during 10,11-epoxymethylfarnesoate oxidation is determined to be the 12-hydroxy isomer
-
-
?
methyl 4-methylphenyl sulfide + O2 + NADH
methyl 4-methylphenyl sulfoxide + methyl 4-methylphenyl sulfone + NAD+ + H2O
show the reaction diagram
-
41% conversion
product ratio of 95:5
-
?
methyl farnesoate + O2 + NADPH
?
show the reaction diagram
-
the major product of C(78-82,F87L,328-330) during methylfarnesoate oxidation is determined to be the 12-hydroxy isomer
-
-
?
methyl phenyl sulfide + O2 + NADH
methyl phenyl sulfoxide + methyl phenyl sulfone + NAD+ + H2O
show the reaction diagram
-
55% conversion
product ratio of 77:23
-
?
methylphenylsulfide + NADH + H+ + O2
methylphenylsulfoxide + NAD+ + H2O
show the reaction diagram
-
catalyzed by StyA of Pseudomonas sp. VLB120 and electrochemical FAD reduction
-
-
?
methyltestosterone + O2 + NADPH
?
show the reaction diagram
-
-
-
?
metolachlor + NADPH + O2 + FAD
?
show the reaction diagram
Sorghum sp.
-
de-ethylation
-
-
?
minocycline + reduced flavoprotein + O2
11a-hydroxy-minocycline + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
myristic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
myristic acid + reduced flavoprotein + O2
omega-hydroxy-myristic acid + oxidized flavoprotein + H2O
show the reaction diagram
-
isozyme CYP52A17, best substrate
isoform CYP52A17, additional fornmation of about 15% dicarbonic acid
-
?
N'-nitrosonornicotine + O2 + reduced flavoprotein
?
show the reaction diagram
N-acetylindole + O2 + NADH
1-acetyl-1,2-dihydro-3H-indol-3-one + 1-acetyl-1,3-dihydro-2H-indol-2-one + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
naphthalene + O2 + NAD(P)H + cytochrome c
1-naphthol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
regioselective oxidation
-
-
?
naphthalene + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q
-
-
?
narbomycin + reduced ferredoxin + O2
pikromycin + ferredoxin + H2O
show the reaction diagram
nerylacetone + O2 + NADPH
9,10-epoxynerylacetone + 5,6-epoxynerylacetone
show the reaction diagram
-
CYP102A7, high activity
-
-
?
nonylphenol + O2 + NADPH
?
show the reaction diagram
norflurazon + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
octane + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q and for mutant A74G/S189Q
-
-
?
oleandomycin + reduced ferredoxin + O2
4-hydroxy-oleandomycin + ferredoxin + H2O
show the reaction diagram
-
-
-
-
?
oleic acid + NADPH
?
show the reaction diagram
-
CYP102A1, CYP102A2, CYP102A3 and CYP102A7
-
-
?
oleic acid + O2 + NADPH + H+
?
show the reaction diagram
oleic acid + reduced flavoprotein + O2
omega-hydroxy oleic acid + n-decan-dicarboxylic acid + oxidized flavoprotein + H2O
show the reaction diagram
-
isozyme CYP52A13, best substrate,isozyme CYP52A17, good substrate
isozyme CYP52A13, products in ratio 1:1, CYP52A17, ratio 3:7 of hydroxy- and dicarboxy-product
-
?
omega-(p-nitrophenyl)decanoic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
omega-(p-nitrophenyl)dodecanoic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
omega-(p-nitrophenyl)octanoic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
oxytetracycline + reduced flavoprotein + NADPH + O2
11a-hydroxy-oxytetracycline + oxidized flavoprotein + H2O + NADP+
show the reaction diagram
-
-
-
-
?
p-chlorothioanisole + O2 + NADPH
?
show the reaction diagram
p-fluorothioanisole + O2 + NADPH
?
show the reaction diagram
p-methoxythioanisole + O2 + NADPH
?
show the reaction diagram
p-nitrophenol + O2 + NADPH
?
show the reaction diagram
p-tolyl methyl sulfide + O2 + NADPH
?
show the reaction diagram
-
-
-
-
?
palmitic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
palmitic acid + O2 + NADPH
?
show the reaction diagram
-
products of hydroxylation by wild-type CYP102A1 are 15-OH, 14-OH, 13-OH, 12-OH, 11-OH, and 10-OH, corresponding to omega-1 to omega-6 hydroxylation, with omega-1 to omega-3 being the major products in both cases
-
-
?
palmitic acid + O2 + NADPH + H+
?
show the reaction diagram
palmitic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
palmitoleic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
pendimethalin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
phenantrene + O2 + NADPH
?
show the reaction diagram
-
-
-
-
?
phenyl ethyl sulfide + O2 + NADPH
?
show the reaction diagram
-
-
-
-
?
phenylmethylsulfide + NADPH + H+ + O2
phenylmethylsulfoxide + NADP+ + H2O
show the reaction diagram
-
enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
-
-
?
pilocarpine + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
progesterone + O2 + NADPH
?
show the reaction diagram
-
-
-
?
propylbenzene + O2 + NADH
(R)-1-phenyl-1-propanol + (R)-1-phenyl-1-propanol + 1-phenylpropan-1-one + NAD+ + H2O
show the reaction diagram
-
-
product ratio of 79:7:14
-
?
prostaglandin + NADPH + O2
20-hydroxy-prostaglandin + NADP+ + H2O
show the reaction diagram
-
physiological functions are the metabolic inactivation of prostaglandins and the production of 20-hydroxyeicosatetraenoic acid, CYP4A4
-
-
?
prostaglandin A1 + NADPH + O2
20-hydroxy-prostaglandin A1 + NADP+ + H2O
show the reaction diagram
prostaglandin A2 + NADPH + O2
20-hydroxy-prostaglandin A2 + NADP+ + H2O
show the reaction diagram
prostaglandin D2 + NADPH + O2
20-hydroxy-prostaglandin D2 + NADP+ + H2O
show the reaction diagram
-
CYP4A4
-
-
?
prostaglandin E1 + NADPH + O2
20-hydroxy-prostaglandin E1 + NADP+ + H2O
show the reaction diagram
-
CYP4A4
-
-
?
prostaglandin E2 + NADPH + O2
20-hydroxy-prostaglandin E2 + NADP+ + H2O
show the reaction diagram
-
CYP4A4
-
-
?
prostaglandin F2alpha + NADPH + O2
20-hydroxy-prostaglandin F2alpha + NADP+ + H2O
show the reaction diagram
-
CYP4A4
-
-
?
psoralen + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
pyrene + O2 + NADPH
?
show the reaction diagram
-
-
-
-
?
pyrene + reduced flavoprotein + O2
?
show the reaction diagram
-
-
-
-
?
pyributicarb + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
quinine + NADPH + H+ + O2
3-hydroxyquinine + NADP+ + H2O
show the reaction diagram
RH + reduced flavoprotein + O2
ROH + oxidized flavoprotein + H2O
show the reaction diagram
S-mephenytoin + O2 + 2 H+
?
show the reaction diagram
-
-
-
-
?
sertraline + O2 + 2 H+
demethylsertraline + formaldehyde + H2O
show the reaction diagram
simvastatin + O2 + reduced flavoprotein
6-beta-hydroxy-methyl-simvastatin + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
-
stearic acid + NADPH
?
show the reaction diagram
-
CYP102A7
-
-
?
stearic acid + O2 + NADPH + H+
?
show the reaction diagram
-
-
-
-
?
stearic acid + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
styrene + NADH + H+ + O2
styrene oxide + NAD+ + H2O
show the reaction diagram
styrene + O2 + H2O2
(R)-styrene oxide + (S)-styrene oxide + H2O
show the reaction diagram
-
engineered CYP102A1 heme domain which utilizes H2O2 as electron donor instead of NADPH
-
-
?
styrene + O2 + NAD(P)H
(R)-styrene oxide + (S)-styrene oxide + H2O + NAD(P)+
show the reaction diagram
-
-
enantioselective styrene oxidation with different CYP102A1 mutants, 25% S-isomer for the wild-type enzyme, 58% S-isomer for mutant A74E/F87V/P386S, 49% R-isomer for mutant F87A, 65% R-isomer for mutant A74G/F87V/L188Q, and 92% R-isomer for mutant F87G
-
?
styrene + O2 + NADH
(S)-styrene oxide + 2-phenylethanol + NAD+ + H2O
show the reaction diagram
-
-
product ratio of 81:19
-
?
testosterone + O2 + NADPH
?
show the reaction diagram
testosterone + O2 + NADPH + H+
6beta-hydroxytestosterone + NADP+ + H2O
show the reaction diagram
CYP3A4
-
-
?
testosterone enanthate + O2 + NADPH
?
show the reaction diagram
CYP107
-
-
?
tetracycline + reduced flavoprotein + O2
11a-hydroxy-tetracycline + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
tetradecanoic acid + NADPH
?
show the reaction diagram
-
CYP102A7, highest activity
-
-
?
thiobencarb + O2 + reduced flavoprotein
?
show the reaction diagram
-
-
-
-
?
tolbutamide + O2 + NADPH
?
show the reaction diagram
toluene + O2 + NAD(P)H + cytochrome c
benzyl alcohol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
-
-
-
?
toluene + O2 + NADH
?
show the reaction diagram
-
-
-
-
?
trifluralin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
-
-
-
-
?
xanthotoxin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
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
4-(methylnitrosamino)-1-(3pyridyl)-1-butanone + O2 + reduced flavoprotein
?
show the reaction diagram
-
nicotine oxidase activity of CYP2A6, activates the tobacco-derived carcinogens to mutagenic products
-
-
?
7-ethoxycoumarin + 3 NADH + 3 H+ + O2
7-hydroxycoumarin + 3 NAD+ + ?
show the reaction diagram
-
-
-
-
?
7-ethoxycoumarin + NADPH + O2 + FAD
7-hydroxycoumarin + NADP+ + FADH2 + ?
show the reaction diagram
7-ethoxycoumarin + O2 + NADPH
?
show the reaction diagram
7-ethoxyresorufin + O2 + NADPH
?
show the reaction diagram
7-methoxycoumarin + 3 NADH + 3 H+ + O2
7-hydroxycoumarin + 3 NAD+ + ?
show the reaction diagram
-
-
-
-
?
aflatoxin B1 + O2 + NADPH
?
show the reaction diagram
-
i.e. AFB1, bioactivation of the carcinogenic mycotoxin to a toxic compound, although not acutely toxic at low concentrations, AFB1 had significant chronic effects, including protracted development, increased mortality, decreased pupation rate, and reduced pupal weight, sensitivity varies with developmental stage, whereas intermediate concentrations causes complete mortality in first instars, this same concentration has no detectable adverse effects on larvae encountering AFB1 in fifth instar. These compounds owe their toxicity to their ability to form irreversible adducts to nucleic acids with the concomitant inhibition of DNA replication and DNA-dependent transcription, mortality, overview
-
-
?
aminopyrene + O2 + NADPH
? + formaldehyde + NADP+ + H2O
show the reaction diagram
arachidonic acid + O2 + NADPH
20-hydroxyeicosatetraenoic acid + H2O + NADP+
show the reaction diagram
avermectin + O2 + reduced ferredoxin
4''-oxo-avermectin + H2O + ferredoxin
show the reaction diagram