Trimethylamine N-Oxide (ECMDB04161) (M2MDB000643)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:06:52 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:54:48 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Trimethylamine N-Oxide | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Trimethylamine N-oxide (TMAO) is found at high concentrations in the tissues of fish, and the bacterial reduction of this compound to foul-smelling trimethylamine is a major process in the spoilage of fish. Trimethylamine N-oxide reductase (TOR or TMAO reductase, EC 1.7.2.3) is a microbial enzyme that can reduce TMAO into trimethylamine (TMA), as part of the electron transport chain. The enzyme has been purified from E. coli. It can accept electrons from cytochromes. (Wikipedia; PMID: 1337081; PMID: 11056172) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C3H9NO | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 75.1097 Monoisotopic: 75.068413915 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | UYPYRKYUKCHHIB-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 1184-78-7 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | N,N-dimethylmethanamine oxide | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | trimethylamine-n-oxide | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | C[N+](C)(C)[O-] | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as trialkyl amine oxides. These are hydrocarbyl derivatives of the aminoxide anion, with the general formula R3N+[O-] or R3N=O, where R is an alkyl group. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic nitrogen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Organonitrogen compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Aminoxides | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Trialkyl amine oxides | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 95-99 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Hydrogen ion + Menaquinol 8 + Trimethylamine N-Oxide > Water + Menaquinone 8 + Trimethylamine 2-Demethylmenaquinol 8 + Hydrogen ion + Trimethylamine N-Oxide > 2-Demethylmenaquinone 8 + Water + Trimethylamine a menaquinol + Hydrogen ion + Trimethylamine N-Oxide > a menaquinone + Water + Trimethylamine Trimethylamine N-Oxide + NADH + Hydrogen ion > Trimethylamine + NAD + Water Trimethylamine + 2 (ferricytochrome c)-subunit + Water > Trimethylamine N-Oxide +2 (ferrocytochrome c)-subunit +2 Hydrogen ion Trimethylamine N-Oxide + 3 Hydrogen ion + Menaquinol 8 + 2 Electron > Trimethylamine + Water +2 Hydrogen ion + menaquinone-8 Trimethylamine N-Oxide + NADH + 2 Hydrogen ion > Trimethylamine + NAD + Water | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Hazard, Rene; Cheymol, Jean; Chabrier, Pierre. Trimethylamine oxide. (1962), 1 p. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in electron carrier activity
- Specific function:
- Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- ynfG
- Uniprot ID:
- P0AAJ1
- Molecular weight:
- 22752
- General function:
- Involved in dimethyl sulfoxide reductase activity
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. Allows E.coli to grow anaerobically on Me(2)SO as respiratory oxidant
- Gene Name:
- dmsA
- Uniprot ID:
- P18775
- Molecular weight:
- 90398
Reactions
Dimethylsulfide + menaquinone + H(2)O = dimethylsulfoxide + menaquinol. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- dmsB
- Uniprot ID:
- P18776
- Molecular weight:
- 22869
- General function:
- Involved in dimethyl sulfoxide reductase activity
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- ynfE
- Uniprot ID:
- P77374
- Molecular weight:
- 89779
- General function:
- Involved in dimethyl sulfoxide reductase activity
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
- Gene Name:
- ynfF
- Uniprot ID:
- P77783
- Molecular weight:
- 89986
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions. Can also reduce other N- and S-oxide compounds such as 4-methylmorpholine-N-oxide and biotin sulfoxide (BSO), but with a lower catalytic efficiency
- Gene Name:
- torZ
- Uniprot ID:
- P46923
- Molecular weight:
- 88964
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+). |
- General function:
- Involved in iron ion binding
- Specific function:
- Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torZ. Required for electron transfer to the torZ terminal enzyme
- Gene Name:
- torY
- Uniprot ID:
- P52005
- Molecular weight:
- 40286
- General function:
- Involved in anaerobic electron transport chain
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. DmsC anchors the dmsAB dimer to the membrane and stabilizes it
- Gene Name:
- dmsC
- Uniprot ID:
- P18777
- Molecular weight:
- 30826
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions
- Gene Name:
- torA
- Uniprot ID:
- P33225
- Molecular weight:
- 94455
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+). |
- General function:
- Involved in iron ion binding
- Specific function:
- Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torA. Acts by transferring electrons from the membranous menaquinones to torA. This transfer probably involves an electron transfer pathway from menaquinones to the N-terminal domain of torC, then from the N-terminus to the C-terminus, and finally to torA. TorC apocytochrome negatively autoregulates the torCAD operon probably by inhibiting the torS kinase activity
- Gene Name:
- torC
- Uniprot ID:
- P33226
- Molecular weight:
- 43606
- General function:
- Involved in anaerobic electron transport chain
- Specific function:
- Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. The C subunit anchors the other two subunits to the membrane and stabilize the catalytic subunits
- Gene Name:
- ynfH
- Uniprot ID:
- P76173
- Molecular weight:
- 30523
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368