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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:22:31 UTC

Update Date

2020-02-26 21:37:18 UTC

HMDB ID

HMDB0012296

Secondary Accession Numbers

HMDB12296

Metabolite Identification

Common Name

Trimethylaminoacetone

Description

Trimethylaminoacetone belongs to the class of organic compounds known as alpha-amino ketones. These are ketones containing a carboxylic acid, and an amine group attached to the alpha carbon atom relative to C=O group. Trimethylaminoacetone has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make trimethylaminoacetone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Trimethylaminoacetone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-Oxopropyl)trimethylammonium	HMDB, MeSH
Acetonyltrimethylammonium	HMDB
N,N,N-Trimethyl-2-oxo-1-propanaminium	HMDB
Acetonyltrimethylammonium hydroxide	MeSH, HMDB

Chemical Formula

C₆H₁₄NO

Average Molecular Weight

116.1815

Monoisotopic Molecular Weight

116.107539075

IUPAC Name

trimethyl(2-oxopropyl)azanium

Traditional Name

trimethyl(2-oxopropyl)azanium

CAS Registry Number

13429-97-5

SMILES

CC(=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C6H14NO/c1-6(8)5-7(2,3)4/h5H2,1-4H3/q+1

InChI Key

LFWNPKYGVKNNAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-amino ketones. These are ketones containing a carboxylic acid, and an amine group attached to the alpha carbon atom relative to C=O group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-amino ketones

Alternative Parents

Substituents

Tetraalkylammonium salt
Quaternary ammonium salt
Alpha-aminoketone
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organonitrogen compound
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a small molecule (CPD-5621 )

Ontology

Not Available

Endogenous (HMDB: HMDB0012296)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.65 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-4.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17.77	ChemAxon
pKa (Strongest Basic)	-8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.54 m³·mol⁻¹	ChemAxon
Polarizability	13.57 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	128.092	30932474
DeepCCS	[M-H]-	125.339	30932474
DeepCCS	[M-2H]-	161.617	30932474
DeepCCS	[M+Na]+	136.305	30932474
AllCCS	[M+H]+	122.8	32859911
AllCCS	[M+H-H2O]+	118.8	32859911
AllCCS	[M+NH4]+	126.5	32859911
AllCCS	[M+Na]+	127.6	32859911
AllCCS	[M-H]-	137.8	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	143.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.11 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8229 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.97 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	264.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	677.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	97.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	48.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	248.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	260.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	642.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	783.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1055.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	555.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	409.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	57.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimethylaminoacetone	CC(=O)C[N+](C)(C)C	1182.4	Standard polar	33892256
Trimethylaminoacetone	CC(=O)C[N+](C)(C)C	661.2	Standard non polar	33892256
Trimethylaminoacetone	CC(=O)C[N+](C)(C)C	843.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trimethylaminoacetone,1TMS,isomer #1	CC(=C[N+](C)(C)C)O[Si](C)(C)C	1060.5	Semi standard non polar	33892256
Trimethylaminoacetone,1TMS,isomer #1	CC(=C[N+](C)(C)C)O[Si](C)(C)C	998.2	Standard non polar	33892256
Trimethylaminoacetone,1TMS,isomer #1	CC(=C[N+](C)(C)C)O[Si](C)(C)C	1047.1	Standard polar	33892256
Trimethylaminoacetone,1TMS,isomer #2	C=C(C[N+](C)(C)C)O[Si](C)(C)C	1041.5	Semi standard non polar	33892256
Trimethylaminoacetone,1TMS,isomer #2	C=C(C[N+](C)(C)C)O[Si](C)(C)C	1021.3	Standard non polar	33892256
Trimethylaminoacetone,1TMS,isomer #2	C=C(C[N+](C)(C)C)O[Si](C)(C)C	1120.8	Standard polar	33892256
Trimethylaminoacetone,1TBDMS,isomer #1	CC(=C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1253.1	Semi standard non polar	33892256
Trimethylaminoacetone,1TBDMS,isomer #1	CC(=C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1225.9	Standard non polar	33892256
Trimethylaminoacetone,1TBDMS,isomer #1	CC(=C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1219.5	Standard polar	33892256
Trimethylaminoacetone,1TBDMS,isomer #2	C=C(C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1241.7	Semi standard non polar	33892256
Trimethylaminoacetone,1TBDMS,isomer #2	C=C(C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1230.3	Standard non polar	33892256
Trimethylaminoacetone,1TBDMS,isomer #2	C=C(C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C	1280.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylaminoacetone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kfx-9300000000-e22d0b09ad5c3d0fd7e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethylaminoacetone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethylaminoacetone 10V, Positive-QTOF	splash10-014i-3900000000-4c23cb2191e128176186	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethylaminoacetone 20V, Positive-QTOF	splash10-0002-9300000000-f844d594d5ed468ae12c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethylaminoacetone 40V, Positive-QTOF	splash10-006y-9000000000-5f636c3cf02527432113	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethylaminoacetone 10V, Positive-QTOF	splash10-014i-4900000000-7268294b32e366098fa2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethylaminoacetone 20V, Positive-QTOF	splash10-05mk-9200000000-8d9d01206ee4fb17404f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethylaminoacetone 40V, Positive-QTOF	splash10-0a4i-9000000000-0ce7f0962083e9d70d52	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028921

KNApSAcK ID

Not Available

Chemspider ID

133796

KEGG Compound ID

Not Available

BioCyc ID

CPD-5621

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151806

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bremer J: Carnitine--metabolism and functions. Physiol Rev. 1983 Oct;63(4):1420-80. [PubMed:6361812 ]

Showing metabocard for Trimethylaminoacetone (HMDB0012296)

MOL for HMDB0012296 (Trimethylaminoacetone)

3D MOL for HMDB0012296 (Trimethylaminoacetone)

3D SDF for HMDB0012296 (Trimethylaminoacetone)

3D-SDF for HMDB0012296 (Trimethylaminoacetone)

PDB for HMDB0012296 (Trimethylaminoacetone)

3D PDB for HMDB0012296 (Trimethylaminoacetone)

SMILES for HMDB0012296 (Trimethylaminoacetone)

INCHI for HMDB0012296 (Trimethylaminoacetone)

Structure for HMDB0012296 (Trimethylaminoacetone)

3D Structure for HMDB0012296 (Trimethylaminoacetone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra