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Showing metabocard for Trimethylamine (HMDB0000906)

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enzymes (5) Show 5 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:17 UTC
HMDB IDHMDB0000906
Secondary Accession Numbers
  • HMDB00906
Metabolite Identification
Common NameTrimethylamine
DescriptionTrimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia like odor in higher concentrations. Trimethylamine has a boiling point of 2.9 degree centigrade and is a gas at room temperature. Trimethylamine usually comes in pressurized gas cylinders or as a 40% solution in water. Trimethylamine is a nitrogenous base and its positively charged cation is called trimethylammonium cation. A common salt of trimethylamine is trimethylammonium chloride, a hygroscopic colorless solid. Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the fishy odor often associated with fouling fish, bacterial vagina infections, and bad breath. It is also associated with taking large doses of choline. Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. Trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell. Trimethylamine in the urine is a biomarker for the consumption of legumes. It has also been found to be a product of various types of bacteria, such as Achromobacter, Acinetobacter, Actinobacteria, Aeromonas, Alcaligenes, Alteromonas, Anaerococcus, Bacillus, Bacteroides, Bacteroidetes, Burkholderia, Campylobacter, Citrobacter, Clostridium, Desulfitobacterium, Desulfovibrio, Desulfuromonas, Edwardsiella, Enterobacter, Enterococcus, Escherichia, Eubacterium, Firmicutes, Flavobacterium, Gammaproteobacteria, Haloanaerobacter, Klebsiella, Micrococcus, Mobiluncus, Olsenella, Photobacterium, Proteobacteria, Proteus, Providencia, Pseudomonas, Rhodopseudomonas, Ruminococcus, Salmonella, Sarcina, Serratia, Shewanella, Shigella, Sinorhizobium, Sporomusa, Staphylococcus, Stigmatella, Streptococcus, Vibrio and Yokenella (PMID:26687352 ; PMID:25108210 ; PMID:24909875 ; PMID:28506279 ; PMID:27190056 ). Trimethylamine is a marker for urinary tract infection brought on by E. coli. (PMID:25108210 ; PMID:24909875 ). It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ).
Structure
Data?1676999717
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000906 (Trimethylamine)

Trimethylamine Oxide.mol
  Mrv1652305271900312D          

  4  3  0  0  0  0            999 V2000
   -0.2062    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
M  END
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3D MOL for HMDB0000906 (Trimethylamine)

HMDB0000906
     RDKit          3D
Trimethylamine
 13 12  0  0  0  0  0  0  0  0999 V2000
   -0.8222   -1.0742    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463   -0.0736   -0.3039 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    1.2525   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -0.1719   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -0.7169    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -1.8062   -0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -1.7034    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1727    1.9418    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521    1.6221   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680    1.3368    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6490   -1.2160    0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    0.5078    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8513    0.1012   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  4 13  1  0
M  END
Download

3D SDF for HMDB0000906 (Trimethylamine)

Trimethylamine Oxide.mol
  Mrv1652305271900312D          

  4  3  0  0  0  0            999 V2000
   -0.2062    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6187    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000906

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C3H9N/c1-4(2)3/h1-3H3

> <INCHI_KEY>
GETQZCLCWQTVFV-UHFFFAOYSA-N

> <FORMULA>
C3H9N

> <MOLECULAR_WEIGHT>
59.1103

> <EXACT_MASS>
59.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
7.638513658561092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethylamine

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
0.19016946566666637

> <ALOGPS_LOGS>
1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.57376321286538

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
19.9881

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethylamine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0000906 (Trimethylamine)

HMDB0000906
     RDKit          3D
Trimethylamine
 13 12  0  0  0  0  0  0  0  0999 V2000
   -0.8222   -1.0742    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463   -0.0736   -0.3039 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5746    1.2525   -0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -0.1719   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7202   -0.7169    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -1.8062   -0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -1.7034    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1727    1.9418    0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521    1.6221   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680    1.3368    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6490   -1.2160    0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782    0.5078    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8513    0.1012   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  3  8  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  4 13  1  0
M  END
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PDB for HMDB0000906 (Trimethylamine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Trimethylamine Oxide.mol                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0      -0.385   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.155  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.155   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.155   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0000906 (Trimethylamine)

COMPND    HMDB0000906
HETATM    1  C1  UNL     1      -0.822  -1.074   0.341  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.046  -0.074  -0.304  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.575   1.252  -0.236  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.366  -0.172  -0.114  1.00  0.00           C  
HETATM    5  H1  UNL     1      -1.720  -0.717   0.864  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.191  -1.806  -0.429  1.00  0.00           H  
HETATM    7  H3  UNL     1      -0.242  -1.703   1.069  1.00  0.00           H  
HETATM    8  H4  UNL     1       0.173   1.942   0.237  1.00  0.00           H  
HETATM    9  H5  UNL     1      -0.652   1.622  -1.299  1.00  0.00           H  
HETATM   10  H6  UNL     1      -1.568   1.337   0.221  1.00  0.00           H  
HETATM   11  H7  UNL     1       1.649  -1.216   0.087  1.00  0.00           H  
HETATM   12  H8  UNL     1       1.778   0.508   0.652  1.00  0.00           H  
HETATM   13  H9  UNL     1       1.851   0.101  -1.087  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    4
CONECT    3    8    9   10
CONECT    4   11   12   13
END
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SMILES for HMDB0000906 (Trimethylamine)

CN(C)C
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INCHI for HMDB0000906 (Trimethylamine)

InChI=1S/C3H9N/c1-4(2)3/h1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(CH3)3NChEBI
N(CH3)3ChEBI
N,N,N-TrimethylamineChEBI
N,N-DimethylmethanamineChEBI
NMe3ChEBI
TMAChEBI
TridimethylaminomethaneChEBI
TrimethylaminChEBI
DimethylmethaneamineHMDB
N,N-Dimethyl-methanamineHMDB
N-TrimethylamineHMDB
Trimethylamine anhydrousHMDB
Trimethylamine aqueous solutionHMDB
HI OF trimethylamineHMDB
HCL OF TrimethylamineHMDB
HBR OF TrimethylamineHMDB
Chemical FormulaC3H9N
Average Molecular Weight59.1103
Monoisotopic Molecular Weight59.073499293
IUPAC Nametrimethylamine
Traditional Nametrimethylamine
CAS Registry Number75-50-3
SMILES
CN(C)C
InChI Identifier
InChI=1S/C3H9N/c1-4(2)3/h1-3H3
InChI KeyGETQZCLCWQTVFV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentTrialkylamines
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationEnvironmental roleBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-117.1 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility890 mg/mLNot Available
LogP0.16HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility654 g/LALOGPS
logP-0.14ALOGPS
logP0.19ChemAxon
logS1.04ALOGPS
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.99 m³·mol⁻¹ChemAxon
Polarizability7.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+119.82730932474
DeepCCS[M-H]-117.93130932474
DeepCCS[M-2H]-153.42730932474
DeepCCS[M+Na]+127.89830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimethylamineCN(C)C600.1Standard polar33892256
TrimethylamineCN(C)C447.1Standard non polar33892256
TrimethylamineCN(C)C409.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Trimethylamine EI-B (Non-derivatized)splash10-0a4i-9000000000-55145d7583823742b4d02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Trimethylamine EI-B (Non-derivatized)splash10-0a4i-9000000000-55145d7583823742b4d02018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9000000000-6aa19094223b203c2a432017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-909841d5aea15e0624702014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-83029e23f5cbd6a607652012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-9000000000-ed35409515031a3b1b982012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-902429fa0e6ccf9ef7252012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0a4i-9000000000-55145d7583823742b4d02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine 40V, Positive-QTOFsplash10-0006-9000000000-642dcafdbfe03e03d6d72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine 10V, Positive-QTOFsplash10-03di-9000000000-72c88f801535e64a9a232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trimethylamine 20V, Positive-QTOFsplash10-0006-9000000000-af4658f148c840dcb7672021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 10V, Positive-QTOFsplash10-03di-9000000000-d06cd0ed0adb68499d852017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 20V, Positive-QTOFsplash10-03di-9000000000-89bf02c9ad080630c9672017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 40V, Positive-QTOFsplash10-03di-9000000000-d9300b7bd734e223bf4d2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 10V, Negative-QTOFsplash10-0a4i-9000000000-89bb141981944dac6e562017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 20V, Negative-QTOFsplash10-0a4i-9000000000-89bb141981944dac6e562017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 40V, Negative-QTOFsplash10-0a4i-9000000000-e49050d0297528d1845c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 10V, Negative-QTOFsplash10-0a4i-9000000000-d9608e4725a25c2900a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 20V, Negative-QTOFsplash10-0a4i-9000000000-d9608e4725a25c2900a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 40V, Negative-QTOFsplash10-0a4i-9000000000-166727f86b2d8ddfffc82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 10V, Positive-QTOFsplash10-03di-9000000000-12b588010b7079d36b5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 20V, Positive-QTOFsplash10-03di-9000000000-12b588010b7079d36b5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethylamine 40V, Positive-QTOFsplash10-03di-9000000000-668f5a2f2030e01e42df2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.42 +/- 0.12 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified26.55(7.07) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0679 (0.0492-0.0866) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified20.72 +/- 17.19 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified159 (9.00-309) uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified2-6 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified<2 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.24-2.33 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • Lee SK, Kim D-H, ...
 details
UrineDetected and Quantified<10 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified40 (20-60) umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.366 +/- 1.991 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified2.5 (0.3-19.4) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified7.7+/- 7.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.38 +/- 0.48 uMAdult (>18 years old)Bothuremia details
BloodDetected and Quantified13.3 (2.0) uMAdult (>18 years old)FemaleEarly preeclampsia details
BloodDetected and Quantified11.2 (3.1) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified1.5 +/- 0.5 uMAdult (>18 years old)Both
Kidney disease		 details
BloodDetected and Quantified32.36(6.19) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified34.06(8.59) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified6.03 (2.0) uMAdult (>18 years old)FemaleLate-onset preeclampsia details
BloodDetected and Quantified7.6 (3.3) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedasymptomatic diverticulosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn’s Disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohn's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPeriodontal diseases details
UrineDetected and Quantified<2 umol/mmol creatinineAdult (>18 years old)MaleDimethylglycinuria details
UrineDetected and Quantified5-160 umol/mmol creatinineChildren (1-13 years old)BothTrimethylaminuria details
UrineDetected and Quantified87.2-322.7 umol/mmol creatinineAdult (>18 years old)Both
Trimethylaminuria		 details
UrineDetected and Quantified3.659 +/- 2.462 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified22.2 umol/mmol creatinineAdult (>18 years old)BothTrimethylaminuria details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Bain MA, Faull R, Milne RW, Evans AM: Oral L-carnitine: metabolite formation and hemodialysis. Curr Drug Metab. 2006 Oct;7(7):811-6. [PubMed:17073580 ]
Uremia
  1. 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 ]
Early preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
  2. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Late-onset preeclampsia
  1. Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Crohn's disease
  1. Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
Ulcerative colitis
  1. Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Trimethylaminuria
  1. 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. [PubMed:9246418 ]
  2. Chalmers RA, Bain MD, Michelakakis H, Zschocke J, Iles RA: Diagnosis and management of trimethylaminuria (FMO3 deficiency) in children. J Inherit Metab Dis. 2006 Feb;29(1):162-72. [PubMed:16601883 ]
  3. Treacy E, Johnson D, Pitt JJ, Danks DM: Trimethylaminuria, fish odour syndrome: a new method of detection and response to treatment with metronidazole. J Inherit Metab Dis. 1995;18(3):306-12. [PubMed:7474897 ]
  4. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Dimethylglycine Dehydrogenase Deficiency
  1. Moolenaar SH, Poggi-Bach J, Engelke UF, Corstiaensen JM, Heerschap A, de Jong JG, Binzak BA, Vockley J, Wevers RA: Defect in dimethylglycine dehydrogenase, a new inborn error of metabolism: NMR spectroscopy study. Clin Chem. 1999 Apr;45(4):459-64. [PubMed:10102904 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011944
KNApSAcK IDC00001433
Chemspider ID1114
KEGG Compound IDC00565
BioCyc IDTRIMETHYLAMINE
BiGG IDNot Available
Wikipedia LinkTrimethylamine
METLIN ID3772
PubChem Compound1146
PDB IDNot Available
ChEBI ID18139
Food Biomarker OntologyNot Available
VMH IDM03053
MarkerDB IDMDB00000280
Good Scents IDNot Available
References
Synthesis ReferenceHirohata, Saneo; Tanba, Kiyonobu; Inoue, Kenichi. Preparation of trimethylamine by zeolite-catalyzed reaction of methanol and ammonia. Jpn. Kokai Tokkyo Koho (2006), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:7762816 ]
  2. 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. [PubMed:8257730 ]
  3. 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. [PubMed:12097436 ]
  4. 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. [PubMed:9246418 ]
  5. Hillier SL: Diagnostic microbiology of bacterial vaginosis. Am J Obstet Gynecol. 1993 Aug;169(2 Pt 2):455-9. [PubMed:8357044 ]
  6. Chao CK, Zeisel SH: Formation of trimethylamine from dietary choline by Streptococcus sanguis I, which colonizes the mouth. J Nutr Biochem. 1990 Feb;1(2):89-97. [PubMed:15539190 ]
  7. Dzik-Jurasz AS, Prescot AP, Leach MO, Collins DJ: Non-invasive study of human gall bladder bile in vivo using (1)H-MR spectroscopy. Br J Radiol. 2003 Jul;76(907):483-6. [PubMed:12857709 ]
  8. Leys D, Basran J, Talfournier F, Chohan KK, Munro AW, Sutcliffe MJ, Scrutton NS: Flavin radicals, conformational sampling and robust design principles in interprotein electron transfer: the trimethylamine dehydrogenase-electron-transferring flavoprotein complex. Biochem Soc Symp. 2004;(71):1-14. [PubMed:15777008 ]
  9. Zeisel SH, daCosta KA, LaMont JT: Mono-, di- and trimethylamine in human gastric fluid: potential substrates for nitrosodimethylamine formation. Carcinogenesis. 1988 Jan;9(1):179-81. [PubMed:3335043 ]
  10. Mitchell SC, Zhang AQ, Barrett T, Ayesh R, Smith RL: Studies on the discontinuous N-oxidation of trimethylamine among Jordanian, Ecuadorian and New Guinean populations. Pharmacogenetics. 1997 Feb;7(1):45-50. [PubMed:9110361 ]
  11. Al-Waiz M, Ayesh R, Mitchell SC, Idle JR, Smith RL: A genetic polymorphism of the N-oxidation of trimethylamine in humans. Clin Pharmacol Ther. 1987 Nov;42(5):588-94. [PubMed:3677545 ]
  12. 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. [PubMed:15304308 ]
  13. Thithapandha A: A pharmacogenetic study of trimethylaminuria in Orientals. Pharmacogenetics. 1997 Dec;7(6):497-501. [PubMed:9429235 ]
  14. 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 ]
  15. Lam CW, Law CY, To KK, Cheung SK, Lee KC, Sze KH, Leung KF, Yuen KY: NMR-based metabolomic urinalysis: a rapid screening test for urinary tract infection. Clin Chim Acta. 2014 Sep 25;436:217-23. doi: 10.1016/j.cca.2014.05.014. Epub 2014 Jun 6. [PubMed:24909875 ]
  16. 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 ]
  17. Lam CW, Law CY, Sze KH, To KK: Quantitative metabolomics of urine for rapid etiological diagnosis of urinary tract infection: evaluation of a microbial-mammalian co-metabolite as a diagnostic biomarker. Clin Chim Acta. 2015 Jan 1;438:24-8. doi: 10.1016/j.cca.2014.07.038. Epub 2014 Aug 6. [PubMed:25108210 ]
  18. Rath S, Heidrich B, Pieper DH, Vital M: Uncovering the trimethylamine-producing bacteria of the human gut microbiota. Microbiome. 2017 May 15;5(1):54. doi: 10.1186/s40168-017-0271-9. [PubMed:28506279 ]
  19. Fennema D, Phillips IR, Shephard EA: Trimethylamine and Trimethylamine N-Oxide, a Flavin-Containing Monooxygenase 3 (FMO3)-Mediated Host-Microbiome Metabolic Axis Implicated in Health and Disease. Drug Metab Dispos. 2016 Nov;44(11):1839-1850. doi: 10.1124/dmd.116.070615. Epub 2016 May 17. [PubMed:27190056 ]

Enzymes

Enzyme Details
1. Dimethylaniline monooxygenase [N-oxide-forming] 5
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
In contrast with other forms of FMO it does not seem to be a drug-metabolizing enzyme.
Gene Name:
FMO5
Uniprot ID:
P49326
Molecular weight:
32480.04
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Enzyme Details
2. Dimethylaniline monooxygenase [N-oxide-forming] 2
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:
FMO2
Uniprot ID:
Q99518
Molecular weight:
53643.29
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Enzyme Details
3. Dimethylaniline monooxygenase [N-oxide-forming] 4
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides.
Gene Name:
FMO4
Uniprot ID:
P31512
Molecular weight:
63342.055
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Enzyme Details
4. Dimethylaniline monooxygenase [N-oxide-forming] 3
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular weight:
60032.975
Reactions
Trimethylamine + NADPH + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails
Enzyme Details
5. Dimethylaniline monooxygenase [N-oxide-forming] 1
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name:
FMO1
Uniprot ID:
Q01740
Molecular weight:
60310.285
Reactions
Trimethylamine + NADPH + Hydrogen Ion + Oxygen → Trimethylamine N-oxide + NADP + Waterdetails