Reference on EC 1.14.13.148 - trimethylamine monooxygenase
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REF. 
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Guan, S.; Falick, A.M.; Williams, D.E.; Cashman, J.R.
Evidence for complex formation between rabbit lung flavin-containing monooxygenase and calreticulin
Biochemistry
30
9892-9900
1991
Oryctolagus cuniculus
Wu, R.F.; Ichikawa, Y.
An essential lysyl residue (Lys208) in the substrate-binding site of porcine FAD-containing monooxygenase
Eur. J. Biochem.
229
749-753
1995
Sus scrofa
Wu, R.F.; Ichikawa, Y.
Characteristic properties and kinetic analysis with neurotoxins of porcine FAD-containing monooxygenase
Biochim. Biophys. Acta
1208
204-210
1994
Sus scrofa, Electron
Adali, O.; Carver, G.C.; Philpot, R.M.
The effect of arginine-428 mutation on modulation of activity of human liver flavin monooxygenase 3 (FMO3) by imipramine and chlorpromazine
Exp. Toxicol. Pathol.
51
271-276
1999
Homo sapiens
Cashman, J.R.
Some distinctions between flavin-containing and cytochrome P450 monooxygenases
Biochem. Biophys. Res. Commun.
338
599-604
2005
Homo sapiens
Borbas, T.; Benko, B.; Dalmadi, B.; Szabo, I.; Tihanyi, K.
Insulin in flavin-containing monooxygenase regulation. Flavin-containing monooxygenase and cytochrome P450 activities in experimental diabetes
Eur. J. Pharm. Sci.
28
51-58
2006
Rattus, Metazoa
Klick, D.E.; Shadley, J.D.; Hines, R.N.
Differential regulation of human hepatic flavin containing monooxygenase 3 (FMO3) by CCAAT/enhancer-binding protein beta (C/EBPbeta) liver inhibitory and liver activating proteins
Biochem. Pharmacol.
76
268-278
2008
Homo sapiens
Lickteig, A.J.; Riley, R.; Melton, R.J.; Reitz, B.A.; Fischer, H.D.; Stevens, J.C.
Expression and characterization of functional dog flavin-containing monooxygenase 3
Drug Metab. Dispos.
37
1987-1990
2009
Canis lupus familiaris, Homo sapiens
Henderson, M.C.; Siddens, L.K.; Morre, J.T.; Krueger, S.K.; Williams, D.E.
Metabolism of the anti-tuberculosis drug ethionamide by mouse and human FMO1, FMO2 and FMO3 and mouse and human lung microsomes
Toxicol. Appl. Pharmacol.
233
420-427
2008
Homo sapiens (P31513), Mus musculus (P97501)
Liffourrena, A.S.; Salvano, M.A.; Lucchesi, G.I.
Pseudomonas putida A ATCC 12633 oxidizes trimethylamine aerobically via two different pathways
Arch. Microbiol.
192
471-476
2010
Pseudomonas putida A ATCC 12633
Large, P.; Boulton, C.; Crabbe, M.
The reduced nicotinamide-adenine dinucleotide phosphate- and oxygen-dependent N-oxygenation of trimethylamine by Pseudomonas aminovorans
Biochem. J.
128
137P-138P
1972
Aminobacter aminovorans
Lang, D.H.; Yeung, C.K.; Peter, R.M.; Ibarra, C.; Gasser, R.; Itagaki, K.; Philpot, R.M.; Rettie, A.E.
Isoform specificity of trimethylamine N-oxygenation by human flavin-containing monooxygenase (FMO) and P450 enzymes: selective catalysis by FMO3
Biochem. Pharmacol.
56
1005-1012
1998
Homo sapiens
Catucci, G.; Gilardi, G.; Jeuken, L.; Sadeghi, S.
In vitro drug metabolism by C-terminally truncated human flavin-containing monooxygenase 3
Biochem. Pharmacol.
83
551-558
2012
Homo sapiens
Strm, A.
Biosynthesis of trimethylamine oxide in Calanus finmarchicus. Properties of a soluble trimethylamine monooxygenase
Comp. Biochem. Physiol. B
65
243-249
1980
Calanus finmarchicus
-
Haining, R.; Hunter, A.; Sadeque, A.; Philpot, R.; Rettie, A.
Baculovirus-mediated expression and purification of human FMO3: Catalytic, immunochemical, and structural characterization
Drug Metab. Dispos.
25
790-797
1997
Homo sapiens
Gut, I.; Conney, A.H.
The FAD-containing monooxygenase-catalyzed N-oxidation and demethylation of trimethylamine in rat liver microsomes
Drug Metabol. Drug Interact.
9
201-208
1991
Rattus norvegicus
Dolphin, C.; Riley, J.; Smith L, R.; Shephard, E.; Phillips, I.
Structural organization of the human flavin-containing monooxygenase 3 gene (FMO3), the favored candidate for fish-odor syndrome, determined directly from genomic DNA
Genomics
46
260-267
1997
Homo sapiens (P31513)
Treacy, E.; Akerman, B.; Chow, L.; Youil, R.; Bibeau, C.; Lin, J.; Bruce, A.; Knight, M.; Danks, D.; Cashman, J.; Forrest, S.
Mutations of the flavin-containing monooxygenase gene (FMO3) cause trimethylaminuria, a defect in detoxication
Hum. Mol. Genet.
7
839-845
1998
Homo sapiens
Burnettt, V.; Lawton, M.; Philpot, R.
Cloning and sequencing of flavin-containing monooxygenases FMO3 and FMO4 from rabbit and characterization of FMO3
J. Biol. Chem.
269
14314-14322
1994
Oryctolagus cuniculus (P32417), Oryctolagus cuniculus (P36367)
Koukouritaki, S.; Poch, M.; Cabacungan, E.; McCarver, D.; Hines, R.
Discovery of novel flavin-containing monooxygenase 3 (FMO3) single nucleotide polymorphisms and functional analysis of upstream haplotype variants
Mol. Pharmacol.
68
383-392
2005
Homo sapiens (P31513)
Chen, Y.; Patel, N.A.; Crombie, A.; Scrivens, J.H.; Murrell, J.C.
Bacterial flavin-containing monooxygenase is trimethylamine monooxygenase
Proc. Natl. Acad. Sci. USA
108
17791-17796
2011
Ruegeria pomeroyi, Roseovarius sp., Candidatus Pelagibacter ubique, no activity in Oceanicola batsensis, no activity in Roseobacter sp., no activity in Sagittula stellata, Methylocella silvestris, no activity in Dinoroseobacter shibae, Candidatus Pelagibacter ubique HTCC7211, no activity in Roseobacter sp. SK209-2-6, Candidatus Pelagibacter ubique HTCC1002, Roseovarius sp. 217
Mitchell, S.; Smith, R.
A physiological role for flavin-containing monooxygenase (FMO3) in humans
Xenobiotica
40
301-305
2010
Homo sapiens
Fedejko-Kap, B.; Niemira, M.; Radominska-Pandya, A.; Mazerska, Z.
Flavin monooxygenases, FMO1 and FMO3, not cytochrome P450 isoenzymes, contribute to metabolism of anti-tumour triazoloacridinone, C-1305, in liver microsomes and HepG2 cells
Xenobiotica
41
1044-1055
2011
Rattus norvegicus, Homo sapiens (P31513)
Goris, M.; Puntervoll, P.; Rojo, D.; Claussen, J.; Larsen, .; Garcia-Moyano, A.; Almendral, D.; Barbas, C.; Ferrer, M.; Bjerga, G.
Use of flavin-containing monooxygenases for conversion of trimethylamine in salmon protein hydrolysates
Appl. Environ. Microbiol.
86
e02105-20
2020
Methylophaga aminisulfidivorans, Nocardiopsis alba, Micrococcus terreus (A0A1I7MIR7), Methylophaga aminisulfidivorans SK1
Wang, X.; Zhang, N.; Teng, Z.; Wang, P.; Zhang, W.; Chen, X.; Zhang, Y.; Chen, Y.; Fu, H.; Li, C.
Structural and mechanistic insights into dimethylsulfoxide formation through dimethylsulfide oxidation
Front. Microbiol.
12
735793
2021
Candidatus Pelagibacter sp. HTCC7211 (B6BT33)
Wu, RF; Miura, S; Ichikawa, Y
Neurotoxins: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, 1,2,3,4-tetrahydroisoquinoline and 1-methyl-6,7-dihydroxy-tetrahydroisoquinoline as substrates for FAD-containing monooxygenase of porcine liver microsomes.
Biochem Pharmacol
44
2079-81
1992
Sus scrofa, Electron
Lomri, N; Gu, Q; Cashman, JR
Molecular cloning of the flavin-containing monooxygenase (form II) cDNA from adult human liver.
Proc Natl Acad Sci U S A
89
1685-9
1992
Homo sapiens, Sus scrofa, Oryctolagus cuniculus
Venkatesh, K; Levi, PE; Hodgson, E
The flavin-containing monooxygenase of mouse kidney. A comparison with the liver enzyme.
Biochem Pharmacol
42
1411-20
1991
Mus musculus, Sus scrofa, Oryctolagus cuniculus
Kurelec, B
Exclusive activation of aromatic amines in the marine mussel Mytilus edulis by FAD-containing monooxygenase.
Biochem Biophys Res Commun
127
773-8
1985
Sus scrofa, Mytilus edulis
Sum, CY; Kasper, CB
Mixed-function amine oxidase of the rat hepatocyte nuclear envelope. Demonstration and effects of phenobarbital and 3-methylcholanthrene.
Biochem Pharmacol
31
69-73
1982
Rattus
Lee, MY; Smiley, S; Kadkhodayan, S; Hines, RN; Williams, DE
Developmental regulation of flavin-containing monooxygenase (FMO) isoforms 1 and 2 in pregnant rabbit.
Chem Biol Interact
96
75-85
1995
Oryctolagus cuniculus
Wu, RF; Ichikawa, Y
Inhibition of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine metabolic activity of porcine FAD-containing monooxygenase by selective monoamine oxidase-B inhibitors.
FEBS Lett
358
145-8
1995
Sus scrofa
Blake, BL; Philpot, RM; Levi, PE; Hodgson, E
Xenobiotic biotransforming enzymes in the central nervous system: an isoform of flavin-containing monooxygenase (FMO4) is expressed in rabbit brain.
Chem Biol Interact
99
253-61
1996
Oryctolagus cuniculus
Brunelle, A; Bi, YA; Lin, J; Russell, B; Luy, L; Berkman, C; Cashman, J
Characterization of two human flavin-containing monooxygenase (form 3) enzymes expressed in Escherichia coli as maltose binding protein fusions.
Drug Metab Dispos
25
1001-7
1997
Escherichia coli, Homo sapiens
Coecke, S; Debast, G; Phillips, IR; Vercruysse, A; Shephard, EA; Rogiers, V
Hormonal regulation of microsomal flavin-containing monooxygenase activity by sex steroids and growth hormone in co-cultured adult male rat hepatocytes.
Biochem Pharmacol
56
1047-51
1998
Rattus, Homo sapiens
Motika, MS; Zhang, J; Zheng, X; Riedler, K; Cashman, JR
Novel variants of the human flavin-containing monooxygenase 3 (FMO3) gene associated with trimethylaminuria.
Mol Genet Metab
97
128-35
2009
Homo sapiens
Yamazaki, H; Shimizu, M
Survey of variants of human flavin-containing monooxygenase 3 (FMO3) and their drug oxidation activities.
Biochem Pharmacol
85
1588-93
2013
Homo sapiens, Chondrichthyes
Nyagode, BA; Watkins, WJ; Kinloch, RD; Morgan, ET
Selective Modulation of Hepatic Cytochrome P450 and Flavin Monooxygenase 3 Expression during Citrobacter rodentium Infection in Severe Combined Immune-Deficient Mice.
Drug Metab Dispos
40
1894-9
2012
Mus sp., Citrobacter rodentium
Hvattum, E; Bergseth, S; Pedersen, CN; Bremer, J; Aarsland, A; Berge, RK
Microsomal oxidation of dodecylthioacetic acid (a 3-thia fatty acid) in rat liver.
Biochem Pharmacol
41
945-53
0
Rattus
Yamazaki, M; Shimizu, M; Uno, Y; Yamazaki, H
Drug oxygenation activities mediated by liver microsomal flavin-containing monooxygenases 1 and 3 in humans, monkeys, rats, and minipigs.
Biochem Pharmacol
90
159-65
2014
Homo sapiens, Rattus, Macaca fascicularis, Platyrrhini, Metazoa
Hisamuddin, IM; Wehbi, MA; Chao, A; Wyre, HW; Hylind, LM; Giardiello, FM; Yang, VW
Genetic polymorphisms of human flavin monooxygenase 3 in sulindac-mediated primary chemoprevention of familial adenomatous polyposis.
Clin Cancer Res
10
8357-62
2004
Homo sapiens
Chen, Y
Comparative genomics of methylated amine utilization by marine Roseobacter clade bacteria and development of functional gene markers (tmm, gmaS).
Environ Microbiol
14
2308-22
2012
Roseobacter
De Boer, L; Brouwer, JW; Van Hassel, CW; Levering, PR; Dijkhuizen, L
Nitrogen metabolism in the facultative methylotroph Arthrobacter P1 grown with various amines or ammonia as nitrogen sources.
Antonie Van Leeuwenhoek
56
221-32
1989
Arthrobacter sp. P1
Waxman, DJ; Light, DR; Walsh, C
Chiral sulfoxidations catalyzed by rat liver cytochromes P-450.
Biochemistry
21
2499-507
1982
Rattus, Lethrinidae
Zijlstra, JA; Vogel, EW
Influence of metabolic factors on the mutagenic effectiveness of cyclophosphamide in Drosophila melanogaster.
Mutat Res
210
79-92
1989
Drosophila melanogaster, Drosophila
Hajjar, NP; Hodgson, E
Sulfoxidation of thioether-containing pesticides by the flavin-adenine dinucleotide- dependent monooxygenase of pig liver microsomes.
Biochem Pharmacol
31
745-52
1982
Rattus, Sus scrofa
Cashman, JR; Zhang, J
Human flavin-containing monooxygenases.
Annu Rev Pharmacol Toxicol
46
65-100
2006
Homo sapiens
Treberg, JR; Driedzic, WR
Maintenance and accumulation of trimethylamine oxide by winter skate (Leucoraja ocellata): reliance on low whole animal losses rather than synthesis.
Am J Physiol Regul Integr Comp Physiol
291
R1790-8
2006
Mammalia, Leucoraja ocellata, animal, Elasmobranchii
Lin, TH; Tsai, TL
Constructing a linear QSAR for some metabolizable drugs by human or pig flavin-containing monooxygenases using some molecular features selected by a genetic algorithm trained SVM.
J Theor Biol
356
85-97
2014
Homo sapiens, Sus scrofa
Chalmers, RA; Bain, MD; Michelakakis, H; Zschocke, J; Iles, RA
Diagnosis and management of trimethylaminuria (FMO3 deficiency) in children.
J Inherit Metab Dis
29
162-172
2006
Homo sapiens
Collins, HL; Drazul-Schrader, D; Sulpizio, AC; Koster, PD; Williamson, Y; Adelman, SJ; Owen, K; Sanli, T; Bellamine, A
L-Carnitine intake and high trimethylamine N-oxide plasma levels correlate with low aortic lesions in ApoE(-)(/-) transgenic mice expressing CETP.
Atherosclerosis
244
29-37
2016
Homo sapiens, Mus sp.
Wilson, A; McLean, C; Kim, RB
Trimethylamine-N-oxide: a link between the gut microbiome, bile acid metabolism, and atherosclerosis.
Curr Opin Lipidol
27
148-54
2016
gut metagenome
Lidbury, I; Krber, E; Zhang, Z; Zhu, Y; Murrell, JC; Chen, Y; Schfer, H
A mechanism for bacterial transformation of dimethylsulfide to dimethylsulfoxide: a missing link in the marine organic sulfur cycle.
Environ Microbiol
18
2754-66
2016
Ruegeria pomeroyi, heterotrophic bacterium
Bekhit, AEA; Giteru, SG; Holman, BWB; Hopkins, DL
Total volatile basic nitrogen and trimethylamine in muscle foods: Potential formation pathways and effects on human health.
Compr Rev Food Sci Food Saf
20
3620-3666
2021
Microbiota
Hodgson, E; Levi, PE
The role of the flavin-containing monooxygenase (EC 1.14.13.8) in the metabolism and mode of action of agricultural chemicals.
Xenobiotica
22
1175-83
0
Oryctolagus cuniculus
Lemoine, A; Williams, DE; Cresteil, T; Leroux, JP
Hormonal regulation of microsomal flavin-containing monooxygenase: tissue-dependent expression and substrate specificity.
Mol Pharmacol
40
211-7
1991
Rattus
Oae, S; Mikami, A; Matsuura, T; Ogawa-Asada, K; Watanabe, Y; Fujimori, K; Iyanagi, T
Comparison of sulfide oxygenation mechanism for liver microsomal FAD-containing monooxygenase with that for cytochrome P-450.
Biochem Biophys Res Commun
131
567-73
1985
Sus scrofa, Electron
Warrier, M; Shih, DM; Burrows, AC; Ferguson, D; Gromovsky, AD; Brown, AL; Marshall, S; McDaniel, A; Schugar, RC; Wang, Z; Sacks, J; Rong, X; Vallim, TA; Chou, J; Ivanova, PT; Myers, DS; Brown, HA; Lee, RG; Crooke, RM; Graham, MJ; Liu, X; Parini, P; Tontonoz, P; Lusis, AJ; Hazen, SL; Temel, RE; Brown, JM
The TMAO-Generating Enzyme Flavin Monooxygenase 3 Is a Central Regulator of Cholesterol Balance.
Cell Rep
2015
Mus musculus
Ziegler, DM; Duffel, MW; Poulsen, LL
Studies on the nature and regulation of the cellular thio:disulphide potential.
Ciba Found Symp
191-204
1979
Cricetinae, Mus sp.
Cashman, JR; Traiger, GJ; Hanzlik, RP
Pneumotoxic effects of thiobenzamide derivatives.
Toxicology
23
85-93
1982
Mus musculus, Mus sp., Rattus
Li, CY; Chen, XL; Zhang, D; Wang, P; Sheng, Q; Peng, M; Xie, BB; Qin, QL; Li, PY; Zhang, XY; Su, HN; Song, XY; Shi, M; Zhou, BC; Xun, LY; Chen, Y; Zhang, YZ
Structural mechanism for bacterial oxidation of oceanic trimethylamine into trimethylamine N-oxide.
Mol Microbiol
103
992-1003
2017
Bacteria
Sun, Q; Zhu, R; Foss, FW; Macdonald, TL
In vitro metabolism of a model cyclopropylamine to reactive intermediate: insights into trovafloxacin-induced hepatotoxicity.
Chem Res Toxicol
21
711-9
2008
Armoracia rusticana
Qin, QL; Wang, ZB; Su, HN; Chen, XL; Miao, J; Wang, XJ; Li, CY; Zhang, XY; Li, PY; Wang, M; Fang, J; Lidbury, I; Zhang, W; Zhang, XH; Yang, GP; Chen, Y; Zhang, YZ
Oxidation of trimethylamine to trimethylamine N-oxide facilitates high hydrostatic pressure tolerance in a generalist bacterial lineage.
Sci Adv
7
2021
Myroides profundi
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