Enzyme Details

EC Classification

1.14.14.1

Enzyme name
(recommended)

unspecific monooxygenase

Alternative names

substrate,reduced-flavoprotein:oxygen oxidoreductase (RH-hydroxylating or -epoxidizing)
microsomal monooxygenase
xenobiotic monooxygenase
aryl-4-monooxygenase
aryl hydrocarbon hydroxylase
microsomal P-450
flavoprotein-linked monooxygenase
flavoprotein monooxygenase

Classification

Oxidoreductases

Acting on paired donors with incorporation of molecular oxygen

With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen

Catalyses reactions

O2 + Reduced flavoprotein + Alkane <-> H2O + Oxidized flavoprotein + ROH

O2 + Reduced flavoprotein + Melatonin <-> H2O + Oxidized flavoprotein + 6-Hydroxymelatonin

O2 + Reduced flavoprotein + Fatty acid <-> H2O + Oxidized flavoprotein + alpha-Hydroxy fatty acid

H2O + Parathion <-> Hydrogen sulfide + Paraoxon

NADH + H+ + Cytochrome c <-> NAD+ + Reduced cytochrome c

H+ + NADPH + O2 + 7-Ethoxycoumarin <-> H2O + NADP+ + 3-Hydroxy-7-ethoxycoumarin

H+ + NADPH + O2 + 7-Ethoxycoumarin <-> H2O + NADP+ + Acetaldehyde + Umbelliferone

H+ + NADPH + O2 + 7-Methoxycoumarin <-> H2O + NADP+ + 3-Hydroxy-7-methoxycoumarin

H+ + NADPH + O2 + 7-Methoxycoumarin <-> H2O + NADP+ + Formaldehyde + Umbelliferone

H+ + NADPH + O2 + Coumarin <-> H2O + NADP+ + Umbelliferone

H+ + NADPH + O2 + Retinoate <-> H2O + NADP+ + 4-Hydroxyretinoic acid

H+ + NADPH + O2 + Progesterone <-> H2O + NADP+ + 11-Deoxycorticosterone

H+ + NADPH + O2 + 4-Methyl-N-methyl-N-(2-phenyl-2H-pyrazol-3-yl)-benzene sulfonamide <-> H2O + NADP+ + 4-Hydroxymethyl-N-methyl-N-(2-phenyl-2H-pyrazol-3-yl)-benzene sulfonamide

Methadone <-> Methanol + 2-Ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

H+ + NADPH + O2 + Benzo[a]pyrene-7,8-diol <-> H2O + NADP+ + Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide

H+ + NADPH + O2 + Testosterone <-> H2O + NADP+ + Formate + Estradiol-17beta

H+ + NADPH + O2 + Androst-4-ene-3,17-dione <-> H2O + NADP+ + Formate + Estrone

H+ + NADPH + Androst-4-ene-3,17-dione <-> H2O + NADP+ + Formate + Estrone

H+ + NADPH + O2 + (-)-Camphor <-> H2O + NADP+ + (-)-exo-5-Hydroxycamphor

O2 + Reduced flavoprotein + 5-Methoxy-N,N-diisopropyltryptamine <-> H2O + Methanol + Oxidized flavoprotein + 5-Hydroxy-N,N-diisopropyltryptamine

H+ + NADPH + O2 + 7-Ethoxy-4-trifluoromethylcoumarin <-> Ethanol + NADP+ + 4-(Trifluoromethyl)umbelliferone

O2 + Reduced flavoprotein + (+)-Bunitrolol <-> H2O + Oxidized flavoprotein + (+)-4-Hydroxybunitrolol

O2 + Reduced flavoprotein + Debrisoquin <-> H2O + Oxidized flavoprotein + 4-Hydroxydebrisoquin

O2 + Reduced flavoprotein + (-)-Bunitrolol <-> H2O + Oxidized flavoprotein + (-)-4-Hydroxybunitrolol

H+ + NADPH + O2 + 7-Ethoxyresorufin <-> Ethanol + NADP+ + Resorufin

O2 + Reduced flavoprotein + 5-Methoxy-N,N-diisopropyltryptamine <-> H2O + 2-Propanol + Oxidized flavoprotein + 5-Methoxy-N-isopropyltryptamine

O2 + Reduced flavoprotein + 5-Methoxy-N,N-diisopropyltryptamine <-> H2O + Oxidized flavoprotein + 6-Hydroxy-5-methoxy-N,N-diisopropyltryptamine

2 O2 + 2 4-Chloroindole <-> 2 H2O + 4,4'-Dichloroindigo

2 O2 + 2 Indole <-> 2 H2O + Indigo Blue

2 O2 + 2 4-Benzyloxy-indole <-> 2 H2O + 4-Benzyloxy-2-(4'-benzyloxy-1',7'-dihydro-7'-oxo-6'H-indol-6'-ylidene)indolin-3-one

2 O2 + 2 5-Benzyloxy-indole <-> 2 H2O + 5,5'-Dibenzyloxy-indirubin

O2 + Reduced flavoprotein + 1-(3-Trifluoromethylphenyl)piperazine <-> H2O + Oxidized flavoprotein + Hydroxy-TFMPP

H+ + NADPH + 2alpha-Methyl-19-hydroxyandrost-4-ene-3,17-dione <-> NADP+ + 2alpha-Methyl-19-oxoandrost-4-ene-3,17-dione

H+ + NADPH + O2 + 2alpha-Methylandrost-4-ene-3,17-dione <-> H2O + NADP+ + 2alpha-Methyl-19-hydroxyandrost-4-ene-3,17-dione

H+ + NADPH + O2 + 2alpha-Methyl-19-oxoandrost-4-ene-3,17-dione <-> H2O + NADP+ + Formate + 2-Methylestrone

H+ + NADPH + Cytochrome c <-> NADP+ + Reduced cytochrome c

NADP+ + Bufuralol <-> H+ + NADPH + 1-Hydroxy bufuralol

H+ + NADPH + O2 + Dodecanoate <-> H2O + NADP+ + Hydroxylated dodecanoate

H+ + NADPH + O2 + Myristic acid <-> H2O + NADP+ + Hydroxylated tetradecanoate

H+ + NADPH + O2 + Palmitate <-> H2O + NADP+ + Hydroxylated hexadecanoate

H+ + NADPH + O2 + Palmitoleic acid <-> H2O + NADP+ + Hydroxylated palmitoleic acid

H+ + NADPH + O2 + Stearate <-> H2O + NADP+ + Hydroxylated stearic acid

H+ + NADPH + O2 + Linoleate <-> H2O + NADP+ + Hydroxylated linoleate

H+ + NADPH + O2 + 12-Methyl-tetradecanoic acid <-> H2O + NADP+ + Hydroxylated 12-methyl-tetradecanoic acid

H+ + NADPH + O2 + 13-Methyl-tetradecanoic acid <-> H2O + NADP+ + Hydroxylated 13-methyl-tetradecanoic acid

H+ + NADPH + O2 + Palmitate <-> H2O + NADP+ + Hydroxylated palmitic acid

H+ + NADPH + O2 + Phytanate <-> H2O + NADP+ + Hydroxylated phytanate

H+ + NADPH + O2 + 14-Methyl-pentadecanoic acid <-> H2O + NADP+ + Hydroxylated 14-methyl-pentadecanoic acid

H+ + NADPH + O2 + 15-Methyl-palmitic acid <-> H2O + NADP+ + Hydroxylated 15-methyl-palmitic acid

H+ + NADPH + O2 + Arachidonate <-> H2O + NADP+ + Hydroxylated arachidonic acid

H+ + NADPH + O2 + Deltamethrin <-> H2O + NADP+ + Hydroxydeltamethrin

H+ + NADPH + O2 + Esfenvalerate <-> H2O + NADP+ + Hydroxyesfenvalerate

H+ + NADPH + O2 + Phenacetin <-> H2O + Ethanol + NADP+ + Acetaminophen

H+ + NADPH + O2 + Estradiol-17beta <-> H2O + NADP+ + 2-Hydroxyestradiol-17beta

H+ + NADPH + O2 + Estradiol-17beta <-> H2O + NADP+ + 4-Hydroxyestradiol-17beta

H+ + NADPH + O2 + 9,11-Epoxymethano-prostaglandin H2 <-> H2O + NADP+ + 19-Hydroxy-(9,11-epoxymethano)-prostaglandin H2

H+ + NADPH + O2 + 2-Amino-2,4-dimethylimidazo[4,5-f]quinoline <-> H2O + NADP+ + 2-Hydroxyamino-2,4-dimethylimidazo[4,5-f]quinoline

H+ + NADPH + O2 + 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline <-> H2O + NADP+ + 2-Hydroxyamino-3,8-dimethylimidazo[4,5-f]quinoxaline

H+ + NADPH + O2 + 2-Amino-3-methylimidazo[4,5-f]quinoline <-> H2O + NADP+ + 2-Hydroxyamino-3-methylimidazo[4,5-f]quinoline

H+ + NADPH + O2 + 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine <-> H2O + NADP+ + 2-Hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine

H+ + NADPH + O2 + 2-Amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole <-> H2O + NADP+ + 2-Hydroxyamino-6-methyldipyrido[1,2-a:3',2'-d]imidazole

Skatole <-> Hydrogen + 3-Methyleneindolenine

H+ + NADPH + O2 + Testosterone <-> H2O + NADP+ + 6beta-Hydroxytestosterone

H+ + NADPH + O2 + Progesterone <-> H2O + NADP+ + 6beta-Hydroxyprogesterone

H+ + NADPH + O2 + Progesterone <-> H2O + NADP+ + 16alpha-Hydroxyprogesterone

H+ + NADPH + O2 + 7-Methoxyresorufin <-> Methanol + NADP+ + Resorufin

H+ + NADPH + O2 + Aflatoxin B1 <-> H2O + NADP+ + exo-Aflatoxin B1-8,9-epoxide

H+ + NADPH + O2 + Aflatoxin B1 <-> H2O + NADP+ + Aflatoxin Q1

H+ + NADPH + O2 + Nifedipine <-> H2O + NADP+ + Oxidized nifedipine

H+ + NADPH + O2 + Bufuralol <-> H2O + NADP+ + 1-Hydroxy bufuralol

H+ + NADPH + O2 + Tolbutamide <-> H2O + NADP+ + Hydroxytolbutamide

H+ + NADPH + O2 + 7-Benzyloxyresorufin <-> NADP+ + Benzaldehyde + Resorufin

O2 + Bisdesoxyolaquindox <-> H2O + Bisdesoxyolaquindox-2'-carboxyl acid

O2 + Bisdesoxyolaquindox <-> H2O + Glycolaldehyde + 3-Methylquinoxaline 2-carboxamide

H+ + NADPH + O2 + Fenthion <-> H2O + NADP+ + Fenthion-sulfoxide

H+ + NADPH + O2 + Fenthion <-> H2O + NADP+ + Sulfur + Fenthion-oxon

H+ + NADPH + O2 + Fenthion-sulfoxide <-> H2O + NADP+ + Fenthion-sulfone

O2 + Scoparone <-> Unknown + 3-[4-Methoxy-p-(3,6)-benzoquinone]-2-propenoate

H+ + NADPH + O2 + Nicotine <-> 2 H+ + H2O + NADP+ + Cotinine

H+ + NADPH + O2 + Aflatoxin B1 <-> H2O + NADP+ + Aflatoxin M1

H+ + NADPH + O2 + Aflatoxin B1 <-> H2O + NADP+ + Aflatoxin B1-8,9-epoxide

H+ + NADPH + O2 + Aminopyrine <-> H2O + NADP+ + Formaldehyde + Noramidopyrine

H+ + NADPH + O2 + Aniline <-> H2O + NADP+ + 4-Hydroxyaniline

H+ + NADPH + O2 + Retinol <-> H2O + NADP+ + all-trans-Retinal

H+ + NADPH + O2 + all-trans-Retinal <-> H2O + NADP+ + Retinoate

H+ + NADPH + O2 + 7,12-Dimethylbenzo[a]anthracene <-> Unknown + H2O + NADP+

H+ + NADPH + O2 + Cyclophosphamide <-> H2O + NADP+ + 4-Hydroxycyclophosphamide

H+ + NADPH + O2 + 7-Benzyloxy-4-trifluoromethylcoumarin <-> NADP+ + Benzaldehyde + 4-(Trifluoromethyl)umbelliferone

H+ + NADPH + O2 + 7-Benzyloxyquinoline <-> H2O + NADP+ + Benzaldehyde + 7-Hydroxyquinoline

NADPH + O2 + Paclitaxel <-> H2O + NADP+ + 6-alpha-Hydroxypaclitaxel

NADPH + O2 + Amodiaquine <-> H2O + NADP+ + N-desethyl Amodiaquine

NADPH + 2 Hexacyanoferrate(III) <-> H+ + NADP+ + 2 Hexacyanoferrate(II)

NADPH + O2 + Fimasartan <-> H2O + NADP+ + Fimasartan S-oxide

NADPH + O2 + Fimasartan <-> H2O + NADP+ + 1-Hydroxybutyl fimasartan

NADPH + O2 + Fimasartan <-> H2O + NADP+ + Hydroxybutyl fimasartan

NADPH + O2 + Fimasartan <-> H2O + NADP+ + 4-Hydroxybutyl fimasartan

NADPH + O2 + Fimasartan <-> H2O + NADP+ + BR-A-557

NADPH + O2 + Fimasartan <-> H2O + NADP+ + BR-A-535

H+ + NADPH + O2 + Diclofenac <-> H2O + NADP+ + 4'-Hydroxydiclofenac

H+ + NADPH + O2 + Losartan <-> H2O + NADP+ + Losartan carboxylic acid

O2 + [reduced NADPH-hemoprotein reductase] + 1,4-Cineole <-> H2O + [oxidized NADPH-hemoprotein reductase] + 2-exo-Hydroxy-1,4-cineole

O2 + Glimepiride + [reduced NADPH-hemoprotein reductase] <-> H2O + [oxidized NADPH-hemoprotein reductase] + Hydroxyglimepiride

O2 + Gliclazide + [reduced NADPH-hemoprotein reductase] <-> H2O + [oxidized NADPH-hemoprotein reductase] + Methylhydroxygliclazide

Coumarin + CYP2A6 <-> Enzyme-Coumarin complex

Xanthotoxin + CYP2A6 <-> Enzyme-Methoxsalen complex

Dodecanoate + CYP102A5 <-> Enzyme-ligand complex

Palmitate + CYP102A5 <-> Enzyme-ligand complex

Palmitoleic acid + CYP102A5 <-> Enzyme-ligand complex

Linoleate + CYP102A5 <-> Enzyme-ligand complex

CYP102A5 + N-Lauroylglycine <-> Enzyme-ligand complex

CYP102A5 + N-Myristoylglycine <-> Enzyme-ligand complex

CYP102A5 + N-Palmitoylglycine <-> Enzyme-ligand complex

H+ + NADPH + O2 + Retinoate <-> H2O + NADP+ + 4-Oxoretinoic acid

H+ + NADPH + O2 + Retinoate <-> H2O + NADP+ + 18-Hydroxyretinoic acid

H+ + NADPH + O2 + Retinoate <-> H2O + NADP+ + 5,6-Epoxyretinoic acid

H+ + NADPH + O2 + beta-Eudesmol <-> H2O + NADP+ + oxidized beta-Eudesmol

H+ + NADPH + O2 + Estradiol-17beta <-> H2O + NADP+ + Estriol

H+ + NADPH + O2 + Estrone <-> H2O + NADP+ + 2-Hydroxyestrone

H+ + NADPH + O2 + Estrone <-> H2O + NADP+ + 4-Hydroxyestrone

H+ + NADPH + O2 + Estrone <-> H2O + NADP+ + 16alpha-Hydroxyestrone

External links

Expasy
KEGG
BRENDA
IntEnz (EBI)
IUBMB
Reactome
MetaCrop

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