Entry |
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Name |
unspecific monooxygenase;
microsomal monooxygenase;
xenobiotic monooxygenase;
aryl-4-monooxygenase;
aryl hydrocarbon hydroxylase;
microsomal P-450;
flavoprotein-linked monooxygenase;
flavoprotein monooxygenase;
substrate,reduced-flavoprotein:oxygen oxidoreductase (RH-hydroxylating or -epoxidizing)
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Class |
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
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Sysname |
substrate,NADPH---hemoprotein reductase:oxygen oxidoreductase (RH-hydroxylating or -epoxidizing)
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Reaction(IUBMB) |
RH + [reduced NADPH---hemoprotein reductase] + O2 = ROH + [oxidized NADPH---hemoprotein reductase] + H2O [RN: R04122]
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Reaction(KEGG) |
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Substrate |
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Product |
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Comment |
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.
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History |
EC 1.14.14.1 created 1961 as EC 1.99.1.1, transferred 1965 to EC 1.14.1.1, transferred 1972 to EC 1.14.14.1 (EC 1.14.14.2 created 1972, incorporated 1976, EC 1.14.99.8 created 1972, incorporated 1984), modified 2015
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Pathway |
ec00140 | Steroid hormone biosynthesis |
ec00590 | Arachidonic acid metabolism |
ec00980 | Metabolism of xenobiotics by cytochrome P450 |
ec00982 | Drug metabolism - cytochrome P450 |
ec01110 | Biosynthesis of secondary metabolites |
ec01120 | Microbial metabolism in diverse environments |
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Orthology |
K00490 | cytochrome P450 family 4 subfamily F |
K07408 | cytochrome P450 family 1 subfamily A1 |
K07409 | cytochrome P450 family 1 subfamily A2 |
K07410 | cytochrome P450 family 1 subfamily B1 |
K07411 | cytochrome P450 family 2 subfamily A |
K07412 | cytochrome P450 family 2 subfamily B |
K07413 | cytochrome P450 family 2 subfamily C |
K07414 | cytochrome P450 family 2 subfamily D |
K07416 | cytochrome P450 family 2 subfamily F |
K07418 | cytochrome P450 family 2 subfamily J |
K07420 | cytochrome P450 family 2 subfamily S1 |
K07424 | cytochrome P450 family 3 subfamily A |
K07426 | cytochrome P450 family 4 subfamily B1 |
K07428 | cytochrome P450 family 4 subfamily X |
K07429 | cytochrome P450 family 4 subfamily Z |
K14338 | cytochrome P450 / NADPH-cytochrome P450 reductase |
K17685 | cytochrome P450 family 2 subfamily A13 |
K17687 | cytochrome P450 family 4 subfamily A11 |
K17690 | cytochrome P450 family 3 subfamily A5 |
K17691 | cytochrome P450 family 3 subfamily A7 |
K17692 | cytochrome P450 family 3 subfamily A43 |
K17712 | cytochrome P450 family 2 subfamily D6 |
K17718 | cytochrome P450 family 2 subfamily C8 |
K17720 | cytochrome P450 family 2 subfamily C18 |
K17728 | cytochrome P450 family 4 subfamily F8 |
K17729 | cytochrome P450 family 4 subfamily F11 |
K17730 | cytochrome P450 family 4 subfamily F12 |
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Genes |
» show all
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Reference |
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Authors |
BOOTH J, BOYLAND E. |
Title |
The biochemistry of aromatic amines. III. Enzymic hydroxylation by rat-liver microsomes. |
Journal |
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Reference |
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Authors |
Fujita T, Mannering GJ. |
Title |
Differences in soluble P-450 hemoproteins from livers of rats treated with phenobarbital and 3-methylcholanthrene. |
Journal |
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Reference |
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Authors |
Haugen DA, Coon MJ. |
Title |
Properties of electrophoretically homogeneous phenobarbital-inducible and beta-naphthoflavone-inducible forms of liver microsomal cytochrome P-450. |
Journal |
J Biol Chem 251:7929-39 (1976) |
Reference |
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Authors |
Imaoka S, Inoue K, Funae Y. |
Title |
Aminopyrine metabolism by multiple forms of cytochrome P-450 from rat liver microsomes: simultaneous quantitation of four aminopyrine metabolites by high-performance liquid chromatography. |
Journal |
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Reference |
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Authors |
Johnson EF, Zounes MC, Muller-Eberhard U. |
Title |
Characterization of three forms of rabbit microsomal cytochrome P-450 by peptide mapping utilizing limited proteolysis in sodium dodecyl sulfate and analysis by gel electrophoresis. |
Journal |
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Reference |
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Authors |
Kupfer D, Miranda GK, Navarro J, Piccolo DE, Theoharides AD. |
Title |
Effect of inducers and inhibitors of monooxygenase on the hydroxylation of prostaglandins in the guinea pig. Evidence for several monooxygenases catalyzing omega- and omega-1-hydroxylation. |
Journal |
J Biol Chem 254:10405-14 (1979) |
Reference |
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Authors |
Lang MA, Gielen JE, Nebert DW. |
Title |
Genetic evidence for many unique liver microsomal P-450-mediated monooxygenase activities in heterogeneic stock mice. |
Journal |
J Biol Chem 256:12068-75 (1981) |
Reference |
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Authors |
Lang MA, Nebert DW. |
Title |
Structural gene products of the Ah locus. Evidence for many unique P-450-mediated monooxygenase activities reconstituted from 3-methylcholanthrene-treated C57BL/6N mouse liver microsomes. |
Journal |
J Biol Chem 256:12058-67 (1981) |
Reference |
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Authors |
Leo MA, Lasker JM, Raucy JL, Kim CI, Black M, Lieber CS |
Title |
Metabolism of retinol and retinoic acid by human liver cytochrome P450IIC8. |
Journal |
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Reference |
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Authors |
Lu AY, Kuntzman R, West S, Jacobson M, Conney AH. |
Title |
Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds, and endogenous substrates. II. Role of the cytochrome P-450 and P-448 fractions in drug and steroid hydroxylations. |
Journal |
J Biol Chem 247:1727-34 (1972) |
Reference |
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Authors |
MITOMA C, POSNER HS, REITZ HC, UDENFRIEND S. |
Title |
Enzymatic hydroxylation of aromatic compounds. |
Journal |
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Reference |
12 |
Authors |
Mitoma, C. and Udenfriend, S. |
Title |
Aryl-4-hydroxylase. |
Journal |
Methods Enzymol 5:816-819 (1962) |
Reference |
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Authors |
Napoli JL, Okita RT, Masters BS, Horst RL. |
Title |
Identification of 25,26-dihydroxyvitamin D3 as a rat renal 25-hydroxyvitamin D3 metabolite. |
Journal |
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Reference |
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Authors |
Nebert DW, Gelboin HV. |
Title |
Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme. |
Journal |
J Biol Chem 243:6242-9 (1968) |
Reference |
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Authors |
Suhara K, Ohashi K, Takahashi K, Katagiri M. |
Title |
Aromatase and nonaromatizing 10-demethylase activity of adrenal cortex mitochondrial P-450(11)beta. |
Journal |
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Reference |
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Authors |
Theoharides AD, Kupfer D. |
Title |
Evidence for different hepatic microsomal monooxygenases catalyzing omega- and (omega-1)-hydroxylations of prostaglandins E1 and E2. Effects of inducers of monooxygenase on the kinetic constants of prostaglandin hydroxylation. |
Journal |
J Biol Chem 256:2168-75 (1981) |
Reference |
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Authors |
Thomas PE, Lu AY, Ryan D, West SB, Kawalek J, Levin W. |
Title |
Immunochemical evidence for six forms of rat liver cytochrome P450 obtained using antibodies against purified rat liver cytochromes P450 and P448. |
Journal |
Mol Pharmacol 12:746-58 (1976) |
Other DBs |
ExPASy - ENZYME nomenclature database: | 1.14.14.1 |
UM-BBD (Biocatalysis/Biodegradation Database): | 1.14.14.1 |
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LinkDB |
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