Livestock Metabolome Database: Showing metabocard for Trimethylamine N-oxide (LMDB00278)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:17 UTC

Update Date

2021-04-30 20:57:45 UTC

Lmdb

LMDB00278

Secondary Accession Numbers

None

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 animals. 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. 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 animal 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 ).

Structure

MOL SDF 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

Chemical Formula

C₃H₉NO

Average Molecular Weight

75.1097

Monoisotopic Molecular Weight

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-9000000000-426384c1c05ab5b584be	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-056r-9000000000-9ba99fcfab36000c7757	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-77dcb5a2685e3154e9f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-dabc3f78669637484204	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-9000000000-0e637352d88abe7c2b0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a4i-9000000000-d155aab0cf63bd6365ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9000000000-54c4798b9d38df37e8a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-7b4ea1bc9a14eef87f35	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-1e5a0675e8b58686f975	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-056r-9000000000-aeb64eb28a53521764cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-0e637352d88abe7c2b0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-d155aab0cf63bd6365ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-54c4798b9d38df37e8a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-7b4ea1bc9a14eef87f35	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052f-9000000000-7f27d29305df82f75dfe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-056r-9000000000-72bdd3a0798c28024038	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-920d8f0833b6b23281b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-29079a6ae8a064f5386f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-36986ad320354e7e83d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-8d763316b01d6d7682a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-ff78646c3e3f75afce16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-ed1a5c9cf14802f3a117	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-388e7087787fdbab7a18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-6298f48fa1844aa5f438	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-9ca491949ce95689c50c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-89485046f830076c9234	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-28a96c1111fa94368c76	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Jejunum
Kidney
Lung
Milk
Plasma
Serum
Urine

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Lung	Detected but not Quantified	Not Applicable	Not Available	Porcine	23412987	details
Milk	Detected and Quantified	43-46 uM	Not Available	Bovine	20338431	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	Trabi M, Keller M...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	24937646	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	25502722	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Serum	Detected and Quantified	73.5444 +/- 46.0125 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.2658 +/- 11.6812 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.3931 +/- 17.8669 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	79.0288 +/- 65.6846 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.6152 +/- 10.5082 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.158 +/- 17.2043 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.43 +/- 19.44 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	84.5992 +/- 65.9525 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	8.3854 +/- 10.7044 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	21.4212 +/- 16.113 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	6.8002 +/- 5.4965 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	82.1162 +/- 54.7624 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21942754	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	26020888	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21584308	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	23394630	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	44.695 +/- 41.3002 uM	Normal	Ovine	Goldansaz et al.,...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Bovine	22059599	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000925

FooDB ID

FDB010413

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

TRIMENTHLAMINE-N-O

METLIN ID

5876

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB04161

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [23614584 ]
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. [21475195 ]
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. [23563705 ]

Showing metabocard for Trimethylamine N-oxide (LMDB00278)

Structure for LMDB00278 (Trimethylamine N-oxide)