Milk Composition Database: Showing metabocard for Trimethylamine N-oxide (BMDB0000925)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:41 UTC

Update Date

2020-06-04 20:13:10 UTC

MCDB ID

BMDB0000925

Secondary Accession Numbers

BMDB00925

Metabolite Identification

Common Name

Trimethylamine N-oxide

Description

Trimethylamine N-oxide, also known as (CH3)3no or tmao, 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. Trimethylamine N-oxide exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Trimethylamine N-oxide exists in all living organisms, ranging from bacteria to humans. Trimethylamine N-oxide is a potentially toxic compound.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	95 - 99 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	454 mg/mL	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	1	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)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	43 - 46 uM		PMID: 20338431	details

External Links

HMDB ID

HMDB0000925

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Hazard, Rene; Cheymol, Jean; Chabrier, Pierre. Trimethylamine oxide. (1962), 1 p.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]

Showing metabocard for Trimethylamine N-oxide (BMDB0000925)

Structure for BMDB0000925 (Trimethylamine N-oxide)