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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-12-03 00:06:32 UTC
HMDB IDHMDB0000925
Secondary Accession Numbers
  • HMDB00925
Metabolite Identification
Common NameTrimethylamine N-oxide
DescriptionTrimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. In particular, trimethylamine-N-oxide is biosynthesized endogenously from trimethylamine, which is derived from choline, which can be derived from dietary lecithin (phosphatidylcholines) or dietary carnitine. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood. TMAO is an osmolyte that the body will use to counteract the effects of increased concentrations of urea (due to kidney failure) and high levels can be used as a biomarker for kidney problems. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ). Fish odor syndrome or trimethylaminuria is a defect in the production of the enzyme flavin containing monooxygenase 3 (FMO3) causing incomplete breakdown of trimethylamine from choline-containing food into trimethylamine oxide. Trimethylamine then builds up and is released in the person's sweat, urine, and breath, giving off a strong fishy odor. The concentration of TMAO in the blood increases after consuming foods containing carnitine or lecithin (phosphatidylcholines), if the bacteria that convert those substances to TMAO are present in the gut (PMID:23614584 ). High concentrations of carnitine are found in red meat, some energy drinks, and certain dietary supplements; lecithin is found in eggs and is commonly used as an ingredient in processed food. High levels of TMAO are found in many seafoods. Some types of normal gut bacteria (e.g. species of Acinetobacter) in the human gut convert dietary carnitine and dietary lecithin to TMAO (PMID:21475195 ). TMAO alters cholesterol metabolism in the intestines, in the liver and in arterial wall. When TMAO is present, cholesterol metabolism is altered and there is an increased deposition of cholesterol within, and decreased removal of cholesterol from, peripheral cells such as those in the artery wall (PMID:23563705 ). Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish. Trimethylamine N-oxide is found to be associated with maple syrup urine disease and propionic acidemia, which are inborn errors of metabolism. TMAO can also be found in Bacteroidetes, Ruminococcus (PMID:26687352 ).
Structure
Data?1582752165
Synonyms
ValueSource
(CH3)3NOChEBI
Me3n(+)O(-)ChEBI
Me3n(O)ChEBI
N(CH3)3OChEBI
TMAOChEBI
Trimethylamine oxideChEBI
TrimethylaminoxidChEBI
TrimethyloxamineChEBI
N,N-Dimethylmethanamine N-oxideHMDB
TMA-oxideHMDB
Trimethylamine-N-oxideHMDB
TrioxHMDB
Trimethylammonium oxideHMDB
Chemical FormulaC3H9NO
Average Molecular Weight75.1097
Monoisotopic Molecular Weight75.068413915
IUPAC NameN,N-dimethylmethanamine oxide
Traditional Nametrimethylamine-n-oxide
CAS Registry Number1184-78-7
SMILES
C[N+](C)(C)[O-]
InChI Identifier
InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
InChI KeyUYPYRKYUKCHHIB-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAminoxides
Direct ParentTrialkyl amine oxides
Alternative Parents
Substituents
  • Trialkyl amine oxide
  • Trisubstituted n-oxide
  • N-oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point95 - 99 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility454 mg/mLNot Available
LogP-2.570The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility57.8 g/LALOGPS
logP-2ALOGPS
logP-0.93ChemAxon
logS-0.11ALOGPS
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.03 m³·mol⁻¹ChemAxon
Polarizability8.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.86431661259
DarkChem[M-H]-106.37231661259
AllCCS[M+H]+121.72332859911
AllCCS[M-H]-138.17132859911
DeepCCS[M+H]+116.43930932474
DeepCCS[M-H]-114.10430932474
DeepCCS[M-2H]-150.21730932474
DeepCCS[M+Na]+124.62230932474
AllCCS[M+H]+121.732859911
AllCCS[M+H-H2O]+117.532859911
AllCCS[M+NH4]+125.732859911
AllCCS[M+Na]+126.832859911
AllCCS[M-H]-138.232859911
AllCCS[M+Na-2H]-142.432859911
AllCCS[M+HCOO]-147.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Trimethylamine N-oxideC[N+](C)(C)[O-]874.1Standard polar33892256
Trimethylamine N-oxideC[N+](C)(C)[O-]420.5Standard non polar33892256
Trimethylamine N-oxideC[N+](C)(C)[O-]510.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trimethylamine N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-9000000000-426384c1c05ab5b584be2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethylamine N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-28a96c1111fa94368c762014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-056r-9000000000-9ba99fcfab36000c77572012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-77dcb5a2685e3154e9f62012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052f-9000000000-dabc3f786696374842042012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-004i-9000000000-0e637352d88abe7c2b0a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0a4i-9000000000-d155aab0cf63bd6365ca2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0a4i-9000000000-54c4798b9d38df37e8a22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0a4i-9000000000-7b4ea1bc9a14eef87f352012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-052f-9000000000-1e5a0675e8b58686f9752012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-056r-9000000000-aeb64eb28a53521764cf2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ , positive-QTOFsplash10-004i-9000000000-0e637352d88abe7c2b0a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ , positive-QTOFsplash10-0a4i-9000000000-d155aab0cf63bd6365ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ , positive-QTOFsplash10-0a4i-9000000000-54c4798b9d38df37e8a22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ , positive-QTOFsplash10-0a4i-9000000000-7b4ea1bc9a14eef87f352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QQ , positive-QTOFsplash10-052f-9000000000-7f27d29305df82f75dfe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide LC-ESI-QTOF , positive-QTOFsplash10-056r-9000000000-72bdd3a0798c280240382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide 40V, Positive-QTOFsplash10-052f-9000000000-920d8f0833b6b23281b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide 10V, Positive-QTOFsplash10-0a4i-9000000000-29079a6ae8a064f5386f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide 40V, Positive-QTOFsplash10-052f-9000000000-36986ad320354e7e83d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine N-oxide 20V, Positive-QTOFsplash10-0a4i-9000000000-8d763316b01d6d7682a22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine N-oxide 10V, Positive-QTOFsplash10-004i-9000000000-ff78646c3e3f75afce162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine N-oxide 20V, Positive-QTOFsplash10-004i-9000000000-ed1a5c9cf14802f3a1172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine N-oxide 40V, Positive-QTOFsplash10-056r-9000000000-388e7087787fdbab7a182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine N-oxide 10V, Negative-QTOFsplash10-00di-9000000000-6298f48fa1844aa5f4382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine N-oxide 20V, Negative-QTOFsplash10-00di-9000000000-9ca491949ce95689c50c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine N-oxide 40V, Negative-QTOFsplash10-00di-9000000000-89485046f830076c92342017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.81 +/- 1.60 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Male
Normal
details
BloodDetected and Quantified38.81 +/- 20.37 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified37.8 +/- 20.4 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.012 +/- 0.68 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified14645.246 (8920.286-20370.205) nmol/g wet fecesInfant (0-1 year old)Not Specified
Normal
details
FecesDetected and Quantified18417.506 (9541.599-27293.412) nmol/g wet fecesInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected and Quantified30000.564 (7677.659-52323.468) nmol/g wet fecesInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected and Quantified20-125 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified50-1000 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.30-43.08 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified11.40(1.32-30.76) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified8.32(0.08-45.23) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified33.70 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified74.4 +/- 76.6 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified67.1 +/- 45.8 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified69.88 +/- 55.003 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified91 (4.8-509) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified118.7 (35.5-202.1) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.99 +/- 2.93 uMAdult (>18 years old)BothParkinson’s disease details
BloodDetected and Quantified5.46 +/- 4.79 uMAdult (>18 years old)BothParkinson’s disease with motor fluctuation details
BloodDetected and Quantified3.70 +/- 0.95 uMAdult (>18 years old)BothParkinson’s disease without motor fluctuation details
BloodDetected and Quantified99.72 +/- 31.82 uMAdult (>18 years old)Bothuremia details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
BloodDetected and Quantified99.9 +/- 31.9 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Pancreatic cancer
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.44 +/- 0.99 uMAdult (>18 years old)BothParkinson’s disease details
Cerebrospinal Fluid (CSF)Detected and Quantified1.62 +/- 1.038 uMAdult (>18 years old)BothParkinson’s disease with motor fluctuation details
Cerebrospinal Fluid (CSF)Detected and Quantified0.81 +/- 0.44 uMAdult (>18 years old)BothParkinson’s disease without motor fluctuation details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothceliac disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedInflammatory bowel disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn disease
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specifiedceliac disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease
details
UrineDetected and Quantified55 umol/mmol creatinineAdult (>18 years old)MaleDimethylglycinuria details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
UrineDetected and Quantified1-60 umol/mmol creatinineChildren (1-13 years old)BothTrimethylaminuria details
UrineDetected and Quantified54.493 +/- 50.173 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified143 umol/mmol creatinineAdult (>18 years old)FemaleRhabdomyolysis details
UrineDetected and Quantified78 +/- 71 umol/mmol creatinineAdult (>18 years old)BothLung cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
UrineDetected and Quantified15.7 umol/mmol creatinineAdult (>18 years old)MaleTrimethylaminuria details
UrineDetected and Quantified66 +/- 1.3 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency details
UrineDetected and Quantified74 +/- 2.2 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency details
UrineDetected and Quantified38.1 +/- 2.9 umol/mmol creatinineAdult (>18 years old)BothArgininosuccinic aciduria (ASL) details
UrineDetected and Quantified2144.7 +/- 123.4 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
UrineDetected and Quantified140.5 +/- 14.1 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
UrineDetected and Quantified36.4 +/- 1.1 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I details
UrineDetected and Quantified16.1 +/- 1.5 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I details
UrineDetected and Quantified33.1 +/- 1.9 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Bain MA, Faull R, Fornasini G, Milne RW, Evans AM: Accumulation of trimethylamine and trimethylamine-N-oxide in end-stage renal disease patients undergoing haemodialysis. Nephrol Dial Transplant. 2006 May;21(5):1300-4. Epub 2006 Jan 9. [PubMed:16401621 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Pancreatic cancer
  1. OuYang D, Xu J, Huang H, Chen Z: Metabolomic profiling of serum from human pancreatic cancer patients using 1H NMR spectroscopy and principal component analysis. Appl Biochem Biotechnol. 2011 Sep;165(1):148-54. doi: 10.1007/s12010-011-9240-0. Epub 2011 Apr 20. [PubMed:21505807 ]
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
  2. De Angelis M, Vannini L, Di Cagno R, Cavallo N, Minervini F, Francavilla R, Ercolini D, Gobbetti M: Salivary and fecal microbiota and metabolome of celiac children under gluten-free diet. Int J Food Microbiol. 2016 Dec 19;239:125-132. doi: 10.1016/j.ijfoodmicro.2016.07.025. Epub 2016 Jul 19. [PubMed:27452636 ]
Inflammatory bowel disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Crohn's disease
  1. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Trimethylaminuria
  1. Maschke S, Wahl A, Azaroual N, Boulet O, Crunelle V, Imbenotte M, Foulard M, Vermeersch G, Lhermitte M: 1H-NMR analysis of trimethylamine in urine for the diagnosis of fish-odour syndrome. Clin Chim Acta. 1997 Jul 25;263(2):139-46. [PubMed:9246418 ]
  2. Chalmers RA, Bain MD, Michelakakis H, Zschocke J, Iles RA: Diagnosis and management of trimethylaminuria (FMO3 deficiency) in children. J Inherit Metab Dis. 2006 Feb;29(1):162-72. [PubMed:16601883 ]
Lung Cancer
  1. Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
Rhabdomyolysis
  1. Bairaktari E, Seferiadis K, Liamis G, Psihogios N, Tsolas O, Elisaf M: Rhabdomyolysis-related renal tubular damage studied by proton nuclear magnetic resonance spectroscopy of urine. Clin Chem. 2002 Jul;48(7):1106-9. [PubMed:12089184 ]
Argininosuccinic aciduria
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Propionic acidemia
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Tyrosinemia I
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Maple syrup urine disease
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Schizophrenia
  1. Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
Dimethylglycine Dehydrogenase Deficiency
  1. Moolenaar SH, Poggi-Bach J, Engelke UF, Corstiaensen JM, Heerschap A, de Jong JG, Binzak BA, Vockley J, Wevers RA: Defect in dimethylglycine dehydrogenase, a new inborn error of metabolism: NMR spectroscopy study. Clin Chem. 1999 Apr;45(4):459-64. [PubMed:10102904 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010413
KNApSAcK IDNot Available
Chemspider ID1113
KEGG Compound IDC01104
BioCyc IDTRIMENTHLAMINE-N-O
BiGG IDNot Available
Wikipedia LinkTrimethylamine_oxide
METLIN ID5876
PubChem Compound1145
PDB IDNot Available
ChEBI ID15724
Food Biomarker OntologyNot Available
VMH IDM03054
MarkerDB IDMDB00000283
Good Scents IDrw1293651
References
Synthesis ReferenceHazard, Rene; Cheymol, Jean; Chabrier, Pierre. Trimethylamine oxide. (1962), 1 p.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. [PubMed:8257730 ]
  3. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  4. Chung YL, Rider LG, Bell JD, Summers RM, Zemel LS, Rennebohm RM, Passo MH, Hicks J, Miller FW, Scott DL: Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies. Arthritis Rheum. 2005 Aug 15;53(4):565-70. [PubMed:16082628 ]
  5. Messana I, Forni F, Ferrari F, Rossi C, Giardina B, Zuppi C: Proton nuclear magnetic resonance spectral profiles of urine in type II diabetic patients. Clin Chem. 1998 Jul;44(7):1529-34. [PubMed:9665433 ]
  6. Maschke S, Wahl A, Azaroual N, Boulet O, Crunelle V, Imbenotte M, Foulard M, Vermeersch G, Lhermitte M: 1H-NMR analysis of trimethylamine in urine for the diagnosis of fish-odour syndrome. Clin Chim Acta. 1997 Jul 25;263(2):139-46. [PubMed:9246418 ]
  7. Kenyon S, Carmichael PL, Khalaque S, Panchal S, Waring R, Harris R, Smith RL, Mitchell SC: The passage of trimethylamine across rat and human skin. Food Chem Toxicol. 2004 Oct;42(10):1619-28. [PubMed:15304308 ]
  8. Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. [PubMed:9429235 ]
  9. On SL, Holmes B: Effect of inoculum size on the phenotypic characterization of Campylobacter species. J Clin Microbiol. 1991 May;29(5):923-6. [PubMed:2056060 ]
  10. Shepshelovich J, Goldstein-Magal L, Globerson A, Yen PM, Rotman-Pikielny P, Hirschberg K: Protein synthesis inhibitors and the chemical chaperone TMAO reverse endoplasmic reticulum perturbation induced by overexpression of the iodide transporter pendrin. J Cell Sci. 2005 Apr 15;118(Pt 8):1577-86. Epub 2005 Mar 22. [PubMed:15784681 ]
  11. Podadera P, Sipahi AM, Areas JA, Lanfer-Marquez UM: Diagnosis of suspected trimethylaminuria by NMR spectroscopy. Clin Chim Acta. 2005 Jan;351(1-2):149-54. [PubMed:15563884 ]
  12. Wolrath H, Stahlbom B, Hallen A, Forsum U: Trimethylamine and trimethylamine oxide levels in normal women and women with bacterial vaginosis reflect a local metabolism in vaginal secretion as compared to urine. APMIS. 2005 Jul-Aug;113(7-8):513-6. [PubMed:16086821 ]
  13. Watt K, Jess TJ, Kelly SM, Price NC, McEwan IJ: Induced alpha-helix structure in the aryl hydrocarbon receptor transactivation domain modulates protein-protein interactions. Biochemistry. 2005 Jan 18;44(2):734-43. [PubMed:15641800 ]
  14. Tang WH, Wang Z, Levison BS, Koeth RA, Britt EB, Fu X, Wu Y, Hazen SL: Intestinal microbial metabolism of phosphatidylcholine and cardiovascular risk. N Engl J Med. 2013 Apr 25;368(17):1575-84. doi: 10.1056/NEJMoa1109400. [PubMed:23614584 ]
  15. Wang Z, Klipfell E, Bennett BJ, Koeth R, Levison BS, Dugar B, Feldstein AE, Britt EB, Fu X, Chung YM, Wu Y, Schauer P, Smith JD, Allayee H, Tang WH, DiDonato JA, Lusis AJ, Hazen SL: Gut flora metabolism of phosphatidylcholine promotes cardiovascular disease. Nature. 2011 Apr 7;472(7341):57-63. doi: 10.1038/nature09922. [PubMed:21475195 ]
  16. Koeth RA, Wang Z, Levison BS, Buffa JA, Org E, Sheehy BT, Britt EB, Fu X, Wu Y, Li L, Smith JD, DiDonato JA, Chen J, Li H, Wu GD, Lewis JD, Warrier M, Brown JM, Krauss RM, Tang WH, Bushman FD, Lusis AJ, Hazen SL: Intestinal microbiota metabolism of L-carnitine, a nutrient in red meat, promotes atherosclerosis. Nat Med. 2013 May;19(5):576-85. doi: 10.1038/nm.3145. Epub 2013 Apr 7. [PubMed:23563705 ]
  17. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  18. Wang Z, Roberts AB, Buffa JA, Levison BS, Zhu W, Org E, Gu X, Huang Y, Zamanian-Daryoush M, Culley MK, DiDonato AJ, Fu X, Hazen JE, Krajcik D, DiDonato JA, Lusis AJ, Hazen SL: Non-lethal Inhibition of Gut Microbial Trimethylamine Production for the Treatment of Atherosclerosis. Cell. 2015 Dec 17;163(7):1585-95. doi: 10.1016/j.cell.2015.11.055. [PubMed:26687352 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in flavin-containing monooxygenase activity
Specific function:
In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
Gene Name:
FMO5
Uniprot ID:
P49326
Molecular weight:
32480.04
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:
FMO2
Uniprot ID:
Q99518
Molecular weight:
53643.29
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides.
Gene Name:
FMO4
Uniprot ID:
P31512
Molecular weight:
63342.055
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular weight:
60032.975
Reactions
Trimethylamine + NADPH + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:
FMO1
Uniprot ID:
Q01740
Molecular weight:
60310.285
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails