|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 220.127.116.11
Enzymes and Genes:
|Homo sapiens :||melatonin O-demethylase
In Pathway: melatonin degradation I
Supersedes EC number: 18.104.22.168
Note that this reaction equation differs from the official Enzyme Commission reaction equation for this EC number, which can be found here .
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, 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
Standard Gibbs Free Energy (ΔrG'° in kcal/mol): -40.466766 [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 22.214.171.124, NADPH-hemoprotein reductase, it forms a system in which two reducing equivalents are supplied by NADPH. Some of the reactions attributed to EC 126.96.36.199, alkane 1-monooxygenase, belong here.
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
Kobayashi00a: Kobayashi K, Yamamoto T, Taguchi M, Chiba K (2000). "High-performance liquid chromatography determination of N- and O-demethylase activities of chemicals in human liver microsomes: application of postcolumn fluorescence derivatization using Nash reagent." Anal Biochem 284(2);342-7. PMID: 10964418
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
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
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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