MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical ReactionsProtein-Modification Reactions
Reactions Classified By SubstrateMacromolecule ReactionsProtein-ReactionsProtein-Modification Reactions

EC Number:

Enzymes and Genes:

Bacillus megaterium: bifunctional P-450/NADPH-P450 reductaseInferred from experiment: CYP102A1
Homo sapiens: cytochrome P450 2A6Inferred from experiment: CYP2A6
cytochrome P450 2B6Inferred from experiment: CYP2B6

Supersedes EC number:

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the direction in which it was curated.

Mass balance status: Balanced.

Enzyme Commission Primary Name: unspecific monooxygenase

Enzyme Commission Synonyms: microsomal monooxygenase, xenobiotic monooxygenase, aryl-4-monooxygenase, aryl hydrocarbon hydroxylase, microsomal P-450, flavoprotein-linked monooxygenase, flavoprotein monooxygenase

Taxonomic Range: Fungi, Viridiplantae, Metazoa, Bacteria

Standard Gibbs Free Energy (ΔrG in kcal/mol): -36.116753Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
A group of heme-thiolate proteins (P-450), 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, NADPH-hemoprotein reductase, it forms a system in which two reducing equivalents are supplied by NADPH. Some of the reactions attributed to EC, alkane 1-monooxygenase, belong here.

Citations: [Booth57, Fujita71, Haugen76, Imaoka88, Johnson79, Kupfer79, Lang81, Lang81a, Leo89, Lu72, Mitoma56 , Napoli81, Nebert68, Suhara88, Theoharides81, Thomas76]

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: KEGG:R04122

Relationship Links: BRENDA:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:, UniProt:RELATED-TO:O04892, UniProt:RELATED-TO:O08336, UniProt:RELATED-TO:P00176, UniProt:RELATED-TO:P00185, UniProt:RELATED-TO:P04800, UniProt:RELATED-TO:P10632, UniProt:RELATED-TO:P14779, UniProt:RELATED-TO:P43083, UniProt:RELATED-TO:P49602, UniProt:RELATED-TO:Q7M0C2, UniProt:RELATED-TO:Q06884, UniProt:RELATED-TO:Q12573

Revised 01-Sep-2011 by Caspi R, SRI International


Booth57: Booth J, Boyland E (1957). "The biochemistry of aromatic amines. III. Enzymic hydroxylation by rat-liver microsomes." Biochem J 66(1);73-8. PMID: 13426111

Fujita71: Fujita T, Mannering GJ (1971). "Differences in soluble P-450 hemoproteins from livers of rats treated with phenobarbital and 3-methylcholanthrene." Chem Biol Interact 3(4);264-5. PMID: 5132997

Haugen76: Haugen DA, Coon MJ (1976). "Properties of electrophoretically homogeneous phenobarbital-inducible and beta-naphthoflavone-inducible forms of liver microsomal cytochrome P-450." J Biol Chem 251(24);7929-39. PMID: 187601

Imaoka88: Imaoka S, Inoue K, Funae Y (1988). "Aminopyrine metabolism by multiple forms of cytochrome P-450 from rat liver microsomes: simultaneous quantitation of four aminopyrine metabolites by high-performance liquid chromatography." Arch Biochem Biophys 265(1);159-70. PMID: 3415241

Johnson79: Johnson EF, Zounes MC, Muller-Eberhard U (1979). "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." Arch Biochem Biophys 192(1);282-9. PMID: 434823

Kupfer79: Kupfer D, Miranda GK, Navarro J, Piccolo DE, Theoharides AD (1979). "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." J Biol Chem 254(20);10405-14. PMID: 489601

Lang81: Lang MA, Gielen JE, Nebert DW (1981). "Genetic evidence for many unique liver microsomal P-450-mediated monooxygenase activities in heterogeneic stock mice." J Biol Chem 256(23);12068-75. PMID: 7298645

Lang81a: Lang MA, Nebert DW (1981). "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." J Biol Chem 256(23);12058-67. PMID: 7298644

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Leo89: Leo MA, Lasker JM, Raucy JL, Kim CI, Black M, Lieber CS (1989). "Metabolism of retinol and retinoic acid by human liver cytochrome P450IIC8." Arch Biochem Biophys 269(1);305-12. PMID: 2916844

Lu72: Lu AY, Kuntzman R, West S, Jacobson M, Conney AH (1972). "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." J Biol Chem 247(6);1727-34. PMID: 4401153

Mitoma56: Mitoma C, Posner HS, Reitz HC, Udenfriend S (1956). "Enzymatic hydroxylation of aromatic compounds." Arch Biochem Biophys 61(2);431-41. PMID: 13314626

Napoli81: Napoli JL, Okita RT, Masters BS, Horst RL (1981). "Identification of 25,26-dihydroxyvitamin D3 as a rat renal 25-hydroxyvitamin D3 metabolite." Biochemistry 20(20);5865-71. PMID: 7295706

Nebert68: Nebert DW, Gelboin HV (1968). "Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme." J Biol Chem 243(23);6242-9. PMID: 4387094

Suhara88: Suhara K, Ohashi K, Takahashi K, Katagiri M (1988). "Aromatase and nonaromatizing 10-demethylase activity of adrenal cortex mitochondrial P-450(11)beta." Arch Biochem Biophys 267(1);31-7. PMID: 3264134

Theoharides81: Theoharides AD, Kupfer D (1981). "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." J Biol Chem 256(5);2168-75. PMID: 7462235

Thomas76: Thomas PE, Lu AY, Ryan D, West SB, Kawalek J, Levin W (1976). "Immunochemical evidence for six forms of rat liver cytochrome P450 obtained using antibodies against purified rat liver cytochromes P450 and P448." Mol Pharmacol 12(5);746-58. PMID: 825720

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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