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Record Information
Version1.0
Creation Date2016-07-13 19:40:30 UTC
Update Date2016-07-20 20:48:38 UTC
LmdbLMDB00015
Secondary Accession NumbersNone
Metabolite Identification
Common NameBetaine
DescriptionBetaine, (or N,N,N-trimethylglycine) was named after its discovery in sugar beet (Beta vulgaris) in the 19th century. It is a small N-trimethylated amino acid, existing in zwitterionic form at neutral pH. It is now often called glycine betaine to distinguish it from other betaines that are widely distributed in microorganisms, plants and animals. Many naturally occurring betaines serve as organic osmolytes, substances synthesized or taken up from the environment by cells for protection against osmotic stress, drought, high salinity or high temperature. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration (Wikipedia). Betaine functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. In particular it methylates homocysteine to methionine, also producing N,N-dimethylglycine. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine comes from either the diet or by the oxidation of choline. Betaine insufficiency is associated with the metabolic syndrome, lipid disorders and diabetes, and may have a role in vascular and other diseases (PMID: 20346934 ). Betaine is important in development, from the pre-implantation embryo to infancy. Betaine is also widely regarded as an anti-oxidant. Betaine has been shown to have an inhibitory effect on NO release in activated microglial cells and may be an effective therapeutic component to control neurological disorders (PMID: 22801281 ). As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th Ed, p1341).
Structure
Thumb
Synonyms
ValueSource
(Trimethylammoniumyl)acetateChEBI
1-Carboxy-N,N,N-trimethylmethanaminium inner saltChEBI
2-N,N,N-trimethylammonio AcetateChEBI
AbromineChEBI
AcidolChEBI
BetChEBI
N,N,N-TrimethylammonioacetateChEBI
N,N,N-TrimethylglycineChEBI
TrimethylaminoacetateChEBI
TrimethylammonioacetateChEBI
TrimethylglycineChEBI
TrimethylglycocollChEBI
(Trimethylammoniumyl)acetic acidGenerator
2-N,N,N-trimethylammonio Acetic acidGenerator
N,N,N-Trimethylammonioacetic acidGenerator
Trimethylaminoacetic acidGenerator
Trimethylammonioacetic acidGenerator
(Carboxymethyl)trimethylammonium hydroxide inner saltHMDB
(trimethylammonio)AcetateHMDB
1-Carboxy-N,N,N-trimethyl-methanaminiumHMDB
1-Carboxy-N,N,N-trimethyl-methanaminium hydroxideHMDB
a-EarleineHMDB
alpha-EarleineHMDB
AminocoatHMDB
BetafinHMDB
Betafin BCRHMDB
Betafin BPHMDB
CystadaneHMDB
Ektasolve eeHMDB
FinnStimHMDB
Glycine betaineHMDB
Glycocoll betaineHMDB
GlycylbetaineHMDB
GreenstimHMDB
Loramine amb 13HMDB
Loramine amb-13HMDB
LycineHMDB
OxyneurineHMDB
Rubrine CHMDB
Trimethylbetaine glycineHMDB
Acidin pepsinMeSH
Beaufour brand OF betaine citrateMeSH
Byk brand OF betaine phosphateMeSH
Fournier brand OF betaine ascorbate and hydrateMeSH
Hydrochloride, betaineMeSH
Logeais brand OF betaine cyclobutyrateMeSH
NovobetaineMeSH
Betaine hydrochlorideMeSH
Betaine orphan brandMeSH
Boizot brand OF betaine aspartateMeSH
C.B.B.MeSH
Citrate de bétaïne upsaMeSH
scorbo-BétaïneMeSH
Stea-16MeSH
Stea16MeSH
Acidin-pepsinMeSH
Citrate de bétaïne beaufourMeSH
Orphan brand OF betaineMeSH
scorbo BétaïneMeSH
AcidinPepsinMeSH
Betaine, glycineMeSH
HepastylMeSH
ScorbobétaïneMeSH
UPSA brand OF betaine citrateMeSH
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name2-(trimethylazaniumyl)acetate
Traditional NameBet
CAS Registry Number107-43-7
SMILES
C[N+](C)(C)CC([O-])=O
InChI Identifier
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
InChI KeyKWIUHFFTVRNATP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-4.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.82 m3·mol-1ChemAxon
Polarizability12.11 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-feacc600820771d2a77bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-e5bbda9fb66994576062View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-c382759eab7d0a87ac27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-a7beb42e6944181ae5d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-1900000000-77fbc4a2b76030d53644View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-2941e4997f202293bf71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-9b9e3cecb77ed4b40b7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-27bbb5f9642306216a0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-1900000000-82a41cbb0f697910b577View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0aor-9500000000-9a0f1853188052d798c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-066r-5900000000-a6291f86046f32ad3c81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-9200000000-709208d6782f1b588501View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a2560fc2add75f79eadbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-b45353825d98488d752aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0aor-9500000000-3fdd9d17a169db5c58ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-fe34051d8d2d4fed6de5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-f32989f795eeceb8b692View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Bile acid
  • Brain cortex
  • Colostrum
  • Jejunum
  • Kidney
  • Liver
  • Lung
  • Meat
  • Milk
  • Pancreas
  • Plasma
  • Proximal colon
  • Serum
  • Synovial Fluid
  • Urine
  • Vitreous Humour
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Bile acidDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Brain cortexDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
JejunumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
KidneyDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LiverDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
LungDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected and Quantified315.07 +/- 23.69 uMNot AvailableBovine details
MeatDetected and Quantified345.85 +/- 38.4 uMNot AvailableBovine details
MeatDetected and Quantified375.31 +/- 38.29 uMNot AvailableBovine details
MeatDetected and Quantified456.74 +/- 30.58 uMNot AvailableBovine details
MilkDetected and Quantified489-1263 uMNot AvailableBovine details
MilkDetected and Quantified459-1410 uMNot AvailableBovine details
PancreasDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Trabi M, Keller M...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Proximal colonDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Proximal colonDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Synovial FluidDetected but not QuantifiedNot ApplicableNot AvailableOvine details
UrineDetected and Quantified116 umol/mmol creatinineNot AvailablePorcine details
UrineDetected and Quantified705 umol/mmol creatinineNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Vitreous HumourDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDDB06756
HMDB IDHMDB00043
FooDB IDFDB009020
Phenol Explorer IDNot Available
KNApSAcK IDC00007291
BiGG ID35786
BioCyc IDBETAINE
METLIN ID287
PDB IDNot Available
Wikipedia LinkTrimethylglycine
Chemspider ID242
ChEBI ID17750
PubChem Compound ID247
Kegg Compound IDC00719
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lever M, Slow S: The clinical significance of betaine, an osmolyte with a key role in methyl group metabolism. Clin Biochem. 2010 Jun;43(9):732-44. doi: 10.1016/j.clinbiochem.2010.03.009. Epub 2010 Mar 25. [20346934 ]
  2. Amiraslani B, Sabouni F, Abbasi S, Nazem H, Sabet M: Recognition of betaine as an inhibitor of lipopolysaccharide-induced nitric oxide production in activated microglial cells. Iran Biomed J. 2012;16(2):84-9. [22801281 ]