AFCDB: Trimethylamine oxide (FDB010413)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:07 UTC

Update date

2024-11-29 22:26:13 UTC

Primary ID

FDB010413

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Trimethylamine oxide

Description

Trimethylamine N-oxide (TMAO) is an oxidation product of trimethylamine and a common metabolite in animals and humans. 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 counter-act the effects of increased concentrations of urea (due to kidney failure) and 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.; Trimethylamine N-oxide, also known by several other names and acronyms, is the organic compound with the formula (CH3)3NO. This colorless solid is usually encountered as the dihydrate. It is an oxidation product of trimethylamine and a common metabolite in animals. It is an osmolyte found in saltwater fish, sharks and rays, molluscs, and crustaceans. Along with free amino acids, it reduces the 3% salinity of seawater to about 1% of dissolved solids inside cells. TMAO decomposes to trimethylamine (TMA), which is the main odorant that is characteristic of degrading seafood.; 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. Urinary TMAO is a biomarker for the consumption of fish, especially cold-water fish.

CAS Number

1184-78-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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

Chemical Formula

C3H9NO

IUPAC name

N,N-dimethylmethanamine oxide

InChI Identifier

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

InChI Key

UYPYRKYUKCHHIB-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

75.1097

Monoisotopic Molecular Weight

75.068413915

Classification

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

Ingestion

Source:

Endogenous

Biological:

Microbe:

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Food and nutrition

Biological role:

Foods

Meats:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	95-99 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	4.65
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-28a96c1111fa94368c76	2014-09-20	View Spectrum
Predicted GC-MS	Trimethylamine oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06vi-9000000000-426384c1c05ab5b584be	Spectrum
Predicted GC-MS	Trimethylamine oxide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-056r-9000000000-9ba99fcfab36000c7757	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-77dcb5a2685e3154e9f6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-dabc3f78669637484204	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-9000000000-0e637352d88abe7c2b0a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0a4i-9000000000-d155aab0cf63bd6365ca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9000000000-54c4798b9d38df37e8a2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-7b4ea1bc9a14eef87f35	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-052f-9000000000-1e5a0675e8b58686f975	2012-08-31	View Spectrum
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
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-0e637352d88abe7c2b0a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-d155aab0cf63bd6365ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-54c4798b9d38df37e8a2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-7b4ea1bc9a14eef87f35	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052f-9000000000-7f27d29305df82f75dfe	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-056r-9000000000-72bdd3a0798c28024038	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-920d8f0833b6b23281b1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-29079a6ae8a064f5386f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-36986ad320354e7e83d5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-8d763316b01d6d7682a2	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-ff78646c3e3f75afce16	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-ed1a5c9cf14802f3a117	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-388e7087787fdbab7a18	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-6298f48fa1844aa5f438	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-9ca491949ce95689c50c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-89485046f830076c9234	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

1113

ChEMBL ID

Not Available

KEGG Compound ID

C01104

Pubchem Compound ID

1145

Pubchem Substance ID

Not Available

ChEBI ID

15724

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00925

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

3738

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

TMO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1293651

SuperScent ID

Not Available

Wikipedia ID

Trimethylamine oxide

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of Trimethylamine N-oxide (TMAO)	SMP0123192	Not Available
Metabolism and Physiological Effects of Oxalic acid	SMP0124875	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Trimethylamine oxide (FDB010413)

Structure for FDB010413 (Trimethylamine oxide)