| 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 |
| K00493 | unspecific monooxygenase |
| K07408 | cytochrome P450 family 1 subfamily A polypeptide 1 |
| K07409 | cytochrome P450 family 1 subfamily A polypeptide 2 |
| K07410 | cytochrome P450 family 1 subfamily B polypeptide 1 |
| 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 S polypeptide 1 |
| K07424 | cytochrome P450 family 3 subfamily A |
| K07426 | cytochrome P450 family 4 subfamily B polypeptide 1 |
| K07428 | cytochrome P450 family 4 subfamily X |
| K07429 | cytochrome P450 family 4 subfamily Z |
| K14338 | cytochrome P450 / NADPH-cytochrome P450 reductase |
| K17684 | cytochrome P450 family 2 subfamily A polypeptide 7 |
| K17685 | cytochrome P450 family 2 subfamily A polypeptide 13 |
| K17690 | cytochrome P450 family 3 subfamily A polypeptide 5 |
| K17691 | cytochrome P450 family 3 subfamily A polypeptide 7 |
| K17692 | cytochrome P450 family 3 subfamily A polypeptide 43 |
| K17712 | cytochrome P450 family 2 subfamily D polypeptide 6 |
| K17718 | cytochrome P450 family 2 subfamily C polypeptide 8 |
| K17720 | cytochrome P450 family 2 subfamily C polypeptide 18 |
| K17728 | cytochrome P450 family 4 subfamily F polypeptide 8 |
| K17729 | cytochrome P450 family 4 subfamily F polypeptide 11 |
| K17730 | cytochrome P450 family 4 subfamily F polypeptide 12 |
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| Genes |
» show all
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| Reference |
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| Authors |
BOOTH J, BOYLAND E. |
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| Title |
The biochemistry of aromatic amines. III. Enzymic hydroxylation by rat-liver microsomes. |
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| Journal |
Biochem J 66:73-8 (1957) |
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| Reference |
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| Authors |
Fujita T, Mannering GJ. |
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| Title |
Differences in soluble P-450 hemoproteins from livers of rats treated with phenobarbital and 3-methylcholanthrene. |
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| Journal |
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| Reference |
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| Authors |
Haugen DA, Coon MJ. |
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| Title |
Properties of electrophoretically homogeneous phenobarbital-inducible and beta-naphthoflavone-inducible forms of liver microsomal cytochrome P-450. |
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| Journal |
J Biol Chem 251:7929-39 (1976) |
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| Reference |
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| Authors |
Imaoka S, Inoue K, Funae Y. |
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| 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. |
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| Journal |
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| Reference |
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| Authors |
Johnson EF, Zounes MC, Muller-Eberhard U. |
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| 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. |
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| Journal |
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| Reference |
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| Authors |
Kupfer D, Miranda GK, Navarro J, Piccolo DE, Theoharides AD. |
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| 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. |
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| Journal |
J Biol Chem 254:10405-14 (1979) |
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| Reference |
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| Authors |
Lang MA, Gielen JE, Nebert DW. |
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| Title |
Genetic evidence for many unique liver microsomal P-450-mediated monooxygenase activities in heterogeneic stock mice. |
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| Journal |
J Biol Chem 256:12068-75 (1981) |
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| Reference |
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| Authors |
Lang MA, Nebert DW. |
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| 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. |
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| Journal |
J Biol Chem 256:12058-67 (1981) |
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| Reference |
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| Authors |
Leo MA, Lasker JM, Raucy JL, Kim CI, Black M, Lieber CS. |
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| Title |
Metabolism of retinol and retinoic acid by human liver cytochrome P450IIC8. |
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| Journal |
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| Reference |
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| Authors |
Lu AY, Kuntzman R, West S, Jacobson M, Conney AH. |
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| 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. |
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| Journal |
J Biol Chem 247:1727-34 (1972) |
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| Reference |
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| Authors |
MITOMA C, POSNER HS, REITZ HC, UDENFRIEND S. |
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| Title |
Enzymatic hydroxylation of aromatic compounds. |
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| Journal |
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| Reference |
12 |
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| Authors |
Mitoma, C. and Udenfriend, S. |
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| Title |
Aryl-4-hydroxylase. |
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| Journal |
Methods Enzymol 5:816-819 (1962) |
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| Reference |
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| Authors |
Napoli JL, Okita RT, Masters BS, Horst RL. |
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| Title |
Identification of 25,26-dihydroxyvitamin D3 as a rat renal 25-hydroxyvitamin D3 metabolite. |
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| Journal |
Biochemistry 20:5865-71 (1981) |
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| Reference |
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| Authors |
Nebert DW, Gelboin HV. |
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| Title |
Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme. |
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| Journal |
J Biol Chem 243:6242-9 (1968) |
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| Reference |
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| Authors |
Suhara K, Ohashi K, Takahashi K, Katagiri M. |
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| Title |
Aromatase and nonaromatizing 10-demethylase activity of adrenal cortex mitochondrial P-450(11)beta. |
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| Journal |
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| Reference |
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| Authors |
Theoharides AD, Kupfer D. |
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| 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. |
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| Journal |
J Biol Chem 256:2168-75 (1981) |
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| Reference |
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| Authors |
Thomas PE, Lu AY, Ryan D, West SB, Kawalek J, Levin W. |
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| Title |
Immunochemical evidence for six forms of rat liver cytochrome P450 obtained using antibodies against purified rat liver cytochromes P450 and P448. |
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| Journal |
Mol Pharmacol 12:746-58 (1976) |
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| 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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