Showing metabocard for Trimethylamine N-oxide (BMDB0000925)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:38:41 UTC
Update Date2020-06-04 20:13:10 UTC
BMDB IDBMDB0000925
Secondary Accession Numbers
  • BMDB00925
Metabolite Identification
Common NameTrimethylamine N-oxide
DescriptionTrimethylamine 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(CH3)3NOChEBI
Me3n(+)O(-)ChEBI
Me3n(O)ChEBI
N(CH3)3OChEBI
TMAOChEBI
Trimethylamine oxideChEBI
TrimethylaminoxidChEBI
TrimethyloxamineChEBI
N,N-Dimethylmethanamine N-oxideHMDB
TMA-oxideHMDB
Trimethylamine-N-oxideHMDB
TrioxHMDB
Trimethylammonium oxideHMDB
Chemical FormulaC3H9NO
Average Molecular Weight75.1097
Monoisotopic Molecular Weight75.068413915
IUPAC NameN,N-dimethylmethanamine oxide
Traditional Nametrimethylamine-n-oxide
CAS Registry Number1184-78-7
SMILES
C[N+](C)(C)[O-]
InChI Identifier
InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3
InChI KeyUYPYRKYUKCHHIB-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAminoxides
Direct ParentTrialkyl 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point95 - 99 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility454 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-0.93ChemAxon
logS-0.11ALOGPS
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.06 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.03 m³·mol⁻¹ChemAxon
Polarizability8.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Epidermis
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Semimembranosus Muscle
  • Testis
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified6 +/- 3 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Trabi M, Keller M...
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Longissimus Thoracis MuscleDetected and Quantified14 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected and Quantified43 - 46 uMNot SpecifiedNot SpecifiedNormal details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Semimembranosus MuscleDetected and Quantified14 +/- 4 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified11 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected		 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected		 details
HMDB IDHMDB0000925
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010413
KNApSAcK IDNot Available
Chemspider ID1113
KEGG Compound IDC01104
BioCyc IDTRIMENTHLAMINE-N-O
BiGG IDNot Available
Wikipedia LinkTrimethylamine_oxide
METLIN ID5876
PubChem Compound1145
PDB IDNot Available
ChEBI ID15724
References
Synthesis ReferenceHazard, Rene; Cheymol, Jean; Chabrier, Pierre. Trimethylamine oxide. (1962), 1 p.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]