MiMeDB: Showing metabocard for Trimethylamine N-oxide (MMDBc0000169)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:24 UTC

Update Date

2024-04-30 19:31:16 UTC

Metabolite ID

MMDBc0000169

Metabolite Identification

Common Name

Trimethylamine N-oxide

Description

Trimethylamine 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
(CH3)3NO	ChEBI
Me3n(+)O(-)	ChEBI
Me3n(O)	ChEBI
N(CH3)3O	ChEBI
TMAO	ChEBI
Trimethylamine oxide	ChEBI
Trimethylaminoxid	ChEBI
Trimethyloxamine	ChEBI
N,N-Dimethylmethanamine N-oxide	HMDB
TMA-oxide	HMDB
Trimethylamine-N-oxide	HMDB
Triox	HMDB
Trimethylammonium oxide	HMDB

Molecular Formula

C₃H₉NO

Average Mass

75.1097

Monoisotopic Mass

75.068413915

IUPAC Name

N,N-dimethylmethanamine oxide

Traditional Name

trimethylamine-n-oxide

CAS Registry Number

1184-78-7

SMILES

C[N+](C)(C)[O-]

InChI Identifier

InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3

InChI Key

UYPYRKYUKCHHIB-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Aminoxides

Direct Parent

Trialkyl 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 Framework

Aliphatic acyclic compounds

External Descriptors

N-oxide (CHEBI:15724 )
a small molecule (TRIMENTHLAMINE-N-O )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	57.8 g/L	ALOGPS
logP	-2	ALOGPS
logP	-0.93	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Basic)	4.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	22.03 m³·mol⁻¹	ChemAxon
Polarizability	8.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-9000000000-426384c1c05ab5b584be	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-056r-9000000000-9ba99fcfab36000c7757	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-77dcb5a2685e3154e9f6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-dabc3f78669637484204	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-9000000000-0e637352d88abe7c2b0a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a4i-9000000000-d155aab0cf63bd6365ca	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9000000000-54c4798b9d38df37e8a2	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-7b4ea1bc9a14eef87f35	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-1e5a0675e8b58686f975	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-056r-9000000000-aeb64eb28a53521764cf	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-0e637352d88abe7c2b0a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-d155aab0cf63bd6365ca	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-54c4798b9d38df37e8a2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-7b4ea1bc9a14eef87f35	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052f-9000000000-7f27d29305df82f75dfe	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-056r-9000000000-72bdd3a0798c28024038	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-920d8f0833b6b23281b1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-29079a6ae8a064f5386f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-36986ad320354e7e83d5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-8d763316b01d6d7682a2	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-ff78646c3e3f75afce16	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-ed1a5c9cf14802f3a117	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-388e7087787fdbab7a18	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-6298f48fa1844aa5f438	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-9ca491949ce95689c50c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-89485046f830076c9234	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-28a96c1111fa94368c76	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Kidney
Liver
Placenta
Saliva
Urine

Tissue Locations

Epidermis
Kidney
Liver
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191814	Dimethylaniline monooxygenase [N-oxide-forming] 5	Unknown	P49326	Homo sapiens
MMDBp0191826	Dimethylaniline monooxygenase [N-oxide-forming] 2	Unknown	Q99518	Homo sapiens
MMDBp0191836	Dimethylaniline monooxygenase [N-oxide-forming] 4	Unknown	P31512	Homo sapiens
MMDBp0191842	Dimethylaniline monooxygenase [N-oxide-forming] 3	Unknown	P31513	Homo sapiens
MMDBp0191856	Dimethylaniline monooxygenase [N-oxide-forming] 1	Unknown	Q01740	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007976	Hydrogen Ion	Water	Not Available	Trimethylamine N-oxide reductase (menaquinol 8)	VMH	30371894
MMDBr0007977	Hydrogen Ion	Water	Not Available	Trimethylamine N-oxide reductase menaquinol 8 (extracellular)	VMH	30371894
MMDBr0007978	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Trimethylamine N-oxide reductase (demethylmenaquinol 8)	VMH	30371894
MMDBr0007979	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Trimethylamine N-oxide reductase demethylmenaquinol 8 (extracellular)	VMH	30371894
MMDBr0010690	Trimethylamine	Water	Flavin containing monooxygenase 1	Flavin-Containing Monooxygenase	VMH; KEGG	30371894
MMDBr0010993	2-Demethylmenaquinol 8	2-Demethylmenaquinone 8	Not Available	Trimethylamine-N-oxide reductase (2-demethylmenaquinone)	VMH	30371894
MMDBr0011005	Hydrogen Ion	Water	Not Available	Trimethylamine-N-oxide reductase (Menaquinol)	VMH	30371894
MMDBr0014428	Iron(3+)	Fe2+	Dimethyl sulfoxide/trimethylamine N-oxide reductase	Reduction	RHEA	34755880
MMDBr0014429	Fe2+	Iron(3+)	Trimethylamine-N-oxide reductase 2	Reduction	RHEA	34755880
MMDBr0019157	Trimethylamine N-oxide	Trimethylamine	Trimethylamine-N-oxide reductase 1	Reduction	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Argininosuccinic aciduria	Slight Decrease	Association	Human Urine	HMDB	19551947
Dimethylglycine dehydrogenase deficiency	Increased	Association	Human Urine	HMDB	10102904
Kidney disease	Increased	Association	Human Blood	HMDB	16401621
Lung cancer	Slight Decrease	Association	Human Urine	HMDB	22157537
Maple syrup urine disease	Decreased	Association	Human Urine	HMDB	19551947
Propionic acidemia		Association	Human Urine	HMDB	19551947
Rhabdomyolysis	Increased	Association	Human Urine	HMDB	12089184
Trimethylaminuria	Decreased	Association	Human Urine	HMDB	9246418
Trimethylaminuria		Association	Human Urine	HMDB	16601883
Tyrosinemia i	Decreased	Association	Human Urine	HMDB	19551947
Uremia	Increased	Association	Human Blood	HMDB	22626821
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	21	Human feces; Human stool; Human ; Human urine; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces; Human stool; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	107	Human ; Human mucosa; Human stool; Human supragingival plaque; Human feces; Human saliva; Human subgingival plaque; Pig ; Human feces; pleural fluid plaque; bal; Human sputum; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Chicken	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	15	Human feces; Human ; Human nasopharyngeal swab; Human supragingival plaque	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	118.7		35.5	202.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9246418
Human Urine	Detected and Quantified	15.7				umol/mmol creatinine	Adult (>18 years old)	Male	Trimethylaminuria	HMDB	9246418
Human Urine	Detected and Quantified	55				umol/mmol creatinine	Adult (>18 years old)	Male	Dimethylglycinuria	HMDB	10102904
Human Urine	Detected and Quantified			20	125	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	10102904
Human Urine	Detected and Quantified	143				umol/mmol creatinine	Adult (>18 years old)	Female	Rhabdomyolysis	HMDB	12089184
Human Saliva	Detected and Quantified	>10				uM	Adult (>18 years old)	Both	Normal	HMDB	12097436
Human Blood	Detected and Quantified	37.8	20.4			uM	Adult (>18 years old)	Both	Normal	HMDB	16401621
Human Blood	Detected and Quantified	99.9	31.9			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	16401621
Human Urine	Detected and Quantified			1	60	umol/mmol creatinine	Children (1-13 years old)	Both	Trimethylaminuria	HMDB	16601883
Human Urine	Detected and Quantified			50	1000	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	16601883
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	17022649
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	17022649
Human Blood	Detected but not Quantified						Children (1-13 years old)	Male	Normal	HMDB	17349089
Human Urine	Detected but not Quantified						Children (1-13 years old)	Male	Normal	HMDB	17349089
Human Urine	Detected and Quantified	74.4	76.6			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	17474139
Human Urine	Detected and Quantified	67.1	45.8			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	17474139
Human Urine	Detected and Quantified	66	1.3			umol/mmol creatinine	Adult (>18 years old)	Both	3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency	HMDB	19551947
Human Urine	Detected and Quantified	74	2.2			umol/mmol creatinine	Adult (>18 years old)	Both	3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency	HMDB	19551947
Human Urine	Detected and Quantified	2144.7	123.4			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	140.5	14.1			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	36.4	1.1			umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	HMDB	19551947
Human Urine	Detected and Quantified	16.1	1.5			umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	HMDB	19551947
Human Urine	Detected and Quantified	33.1	1.9			umol/mmol creatinine	Adult (>18 years old)	Both	Maple syrup urine disease	HMDB	19551947
Human Urine	Detected and Quantified	38.1	2.9			umol/mmol creatinine	Adult (>18 years old)	Both	Argininosuccinic aciduria (ASL)	HMDB	19551947
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21505807
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Pancreatic cancer	HMDB	21505807
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21736852
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Treated celiac disease	HMDB	21970810
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	celiac disease	HMDB	21970810
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	21970810
Human Urine	Detected and Quantified	78	71			umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	HMDB	22157537
Human Feces	Detected and Quantified	14645.246		8920.286	20370.205	nmol/g wet feces	Infant (0-1 year old)	Not Specified	Normal	HMDB	22435727
Human Feces	Detected and Quantified	30000.564		7677.659	52323.468	nmol/g wet feces	Infant (0-1 year old)	Not Specified	Normal	HMDB	22435727
Human Feces	Detected and Quantified	18417.506		9541.599	27293.412	nmol/g wet feces	Infant (0-1 year old)	Not Specified	Normal	HMDB	22435727
Human Blood	Detected and Quantified	99.72	31.82			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	38.81	20.37			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Schizophrenia	HMDB	22800120
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22800120
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected and Quantified	91		4.8	509	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25105552
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25105552
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	celiac disease	HMDB	27452636
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Normal	HMDB	27452636
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Inflammatory bowel disease	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28842642
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Crohn disease	HMDB	28842642
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ulcerative colitis	HMDB	28842642
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected and Quantified	5.46	4.79			uM	Adult (>18 years old)	Both	Parkinson's disease with motor fluctuation	HMDB	31726035
Human Blood	Detected and Quantified	1.81	1.6			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	3.7	0.95			uM	Adult (>18 years old)	Both	Parkinson's disease without motor fluctuation	HMDB	31726035
Human Blood	Detected and Quantified	3.99	2.93			uM	Adult (>18 years old)	Both	Parkinson's disease	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.62	1.038			uM	Adult (>18 years old)	Both	Parkinson's disease with motor fluctuation	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.012	0.68			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.81	0.44			uM	Adult (>18 years old)	Both	Parkinson's disease without motor fluctuation	HMDB	31726035
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.44	0.99			uM	Adult (>18 years old)	Both	Parkinson's disease	HMDB	31726035
Human Urine	Detected and Quantified			0.3	43.08	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Urine	Detected and Quantified	11.4		1.32	30.76	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	8.32		0.08	45.23	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected and Quantified	54.493	50.173			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	69.88	55.003			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	33.7				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	Maj-Britt Schmidt Andersen et al. Discovery of exposure markers in urine for Brassica-containing meals served with different protein sources by UPLC-qTOF-MS untargeted metabolomics. Metabolomics (2013) 9:984-997
Human Urine	Detected and Quantified	38.1	2.9			umol/mmol creatinine	Adult (>18 years old)	Both	Argininosuccinic aciduria (ASL)	HMDB	19551947
Human Urine	Detected and Quantified	55				umol/mmol creatinine	Adult (>18 years old)	Male	Dimethylglycinuria	HMDB	10102904
Human Blood	Detected and Quantified	99.9	31.9			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	16401621
Human Urine	Detected and Quantified	78	71			umol/mmol creatinine	Adult (>18 years old)	Both	Lung cancer	HMDB	22157537
Human Urine	Detected and Quantified	33.1	1.9			umol/mmol creatinine	Adult (>18 years old)	Both	Maple syrup urine disease	HMDB	19551947
Human Urine	Detected and Quantified	140.5	14.1			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	2144.7	123.4			umol/mmol creatinine	Adult (>18 years old)	Both	Propionic acidemia	HMDB	19551947
Human Urine	Detected and Quantified	143				umol/mmol creatinine	Adult (>18 years old)	Female	Rhabdomyolysis	HMDB	12089184
Human Urine	Detected and Quantified	15.7				umol/mmol creatinine	Adult (>18 years old)	Male	Trimethylaminuria	HMDB	9246418
Human Urine	Detected and Quantified			1	60	umol/mmol creatinine	Children (1-13 years old)	Both	Trimethylaminuria	HMDB	16601883
Human Urine	Detected and Quantified	16.1	1.5			umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	HMDB	19551947
Human Urine	Detected and Quantified	36.4	1.1			umol/mmol creatinine	Adult (>18 years old)	Both	Tyrosinemia I	HMDB	19551947
Human Blood	Detected and Quantified	99.72	31.82			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Saliva	Detected and Quantified	>10				uM	Adult (>18 years old)	Both	Normal	HMDB	12097436
Human Urine	Detected and Quantified			0.30	43.08	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Cerebrospinal fluid (csf)	Detected and Quantified	1.012	0.68			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Blood	Detected and Quantified	1.81	1.60			uM	Adult (>18 years old)	Both	Normal	HMDB	31726035
Human Urine	Detected and Quantified	11.40		1.32	30.76	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	118.7		35.5	202.1	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9246418
Human Feces	Detected and Quantified	14645.246		8920.286	20370.205	nmol/g wet feces	Infant (0-1 year old)	Not Specified	Normal	HMDB	22435727
Human Feces	Detected and Quantified	18417.506		9541.599	27293.412	nmol/g wet feces	Infant (0-1 year old)	Not Specified	Normal	HMDB	22435727
Human Urine	Detected and Quantified			20	125	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	10102904
Human Feces	Detected and Quantified	30000.564		7677.659	52323.468	nmol/g wet feces	Infant (0-1 year old)	Not Specified	Normal	HMDB	22435727
Human Blood	Detected and Quantified	37.8	20.4			uM	Adult (>18 years old)	Both	Normal	HMDB	16401621
Human Blood	Detected and Quantified	38.81	20.37			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Urine	Detected and Quantified			50	1000	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	16601883
Human Urine	Detected and Quantified	67.1	45.8			umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	17474139
Human Urine	Detected and Quantified	74.4	76.6			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	17474139
Human Urine	Detected and Quantified	8.32		0.08	45.23	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	91		4.8	509	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	54.493	50.173			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	69.88	55.003			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	33.7				umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21389975
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21505807
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22800120
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	21970810
Human Feces	Detected but not Quantified						Children (1-13 years old)	Not Specified	Normal	HMDB	27452636
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	17022649
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	17022649
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21736852
Human Blood	Detected but not Quantified						Children (1-13 years old)	Male	Normal	HMDB	17349089
Human Urine	Detected but not Quantified						Children (1-13 years old)	Male	Normal	HMDB	17349089
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28842642
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000925

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010413

KNApSAcK ID

Not Available

Chemspider ID

1113

KEGG Compound ID

C01104

BioCyc ID

TRIMENTHLAMINE-N-O

BiGG ID

Not Available

Wikipedia Link

Trimethylamine_oxide

METLIN ID

5876

PubChem Compound

1145

PDB ID

Not Available

ChEBI ID

15724

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

On SL, Holmes B: Effect of inoculum size on the phenotypic characterization of Campylobacter species. J Clin Microbiol. 1991 May;29(5):923-6. doi: 10.1128/jcm.29.5.923-926.1991. [PubMed:2056060 ]
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. doi: 10.1021/ac00101a004. [PubMed:7762816 ]
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. doi: 10.1016/0731-7085(93)80171-v. [PubMed:8257730 ]
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. doi: 10.1016/s0009-8981(97)00060-0. [PubMed:9246418 ]
Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. doi: 10.1097/00008571-199712000-00008. [PubMed:9429235 ]
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 ]
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. doi: 10.1177/154405910208100613. [PubMed:12097436 ]
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. doi: 10.1016/j.fct.2004.05.007. [PubMed:15304308 ]
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. doi: 10.1016/j.cccn.2004.09.006. [PubMed:15563884 ]
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. doi: 10.1021/bi0487701. [PubMed:15641800 ]
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. doi: 10.1242/jcs.02294. Epub 2005 Mar 22. [PubMed:15784681 ]
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. doi: 10.1002/art.21331. [PubMed:16082628 ]
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. doi: 10.1111/j.1600-0463.2005.apm_175.x. [PubMed:16086821 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Trimethylamine N-oxide (MMDBc0000169)

MOL for #<Metabolite:0x0000564af38b2650>

3D MOL for #<Metabolite:0x0000564af38b2650>

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3D-SDF for #<Metabolite:0x0000564af38b2650>

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Structure for #<Metabolite:0x0000564af38b2650>

3D Structure for #<Metabolite:0x0000564af38b2650>