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Record Information
Version1.0
Creation Date2016-09-30 22:18:53 UTC
Update Date2020-05-21 16:29:03 UTC
BMDB IDBMDB0000043
Secondary Accession Numbers
  • BMDB00043
Metabolite Identification
Common NameBetaine
DescriptionBetaine, also known as Bet or acidin pepsin, 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). Betaine exists as a solid, possibly soluble (in water), and a moderately acidic compound (based on its pKa) molecule. Betaine exists in all eukaryotes, ranging from yeast to humans. Betaine participates in a number of enzymatic reactions, within cattle. In particular, Betaine can be biosynthesized from betaine aldehyde; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, Betaine and homocysteine can be converted into dimethylglycine and L-methionine; which is catalyzed by the enzyme betaine--homocysteine S-methyltransferase 1. In cattle, betaine is involved in the metabolic pathway called the betaine metabolism pathway.
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
Glycine betaineKegg
CystadaneKegg
(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
Ektasolve eeHMDB
FinnStimHMDB
Glycocoll betaineHMDB
GlycylbetaineHMDB
GreenstimHMDB
Loramine amb 13HMDB
Loramine amb-13HMDB
LycineHMDB
OxyneurineHMDB
Rubrine CHMDB
Trimethylbetaine glycineHMDB
Acidin pepsinHMDB
Beaufour brand OF betaine citrateHMDB
Byk brand OF betaine phosphateHMDB
Fournier brand OF betaine ascorbate and hydrateHMDB
Hydrochloride, betaineHMDB
Logeais brand OF betaine cyclobutyrateHMDB
NovobetaineHMDB
Betaine hydrochlorideHMDB
Betaine orphan brandHMDB
Boizot brand OF betaine aspartateHMDB
C.B.B.HMDB
Citrate de bétaïne upsaHMDB
Scorbo-bétaïneHMDB
Stea-16HMDB
Stea16HMDB
Acidin-pepsinHMDB
Citrate de bétaïne beaufourHMDB
Orphan brand OF betaineHMDB
Scorbo bétaïneHMDB
AcidinPepsinHMDB
Betaine, glycineHMDB
HepastylHMDB
ScorbobétaïneHMDB
UPSA brand OF betaine citrateHMDB
Stea 16HMDB
BetaineChEBI
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name2-(trimethylazaniumyl)acetate
Traditional Name(trimethylammonio)acetate
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
Description 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
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point293 - 301 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility611.0 mg/mL at 19 °CNot 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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.82 m³·mol⁻¹ChemAxon
Polarizability12.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-96ab6e2136fe7e03b63aView in MoNA
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-QQ , positivesplash10-066r-5900000000-a6291f86046f32ad3c81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9200000000-709208d6782f1b588501View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-a7beb42e6944181ae5d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-77fbc4a2b76030d53644View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-2941e4997f202293bf71View 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-QQ , positivesplash10-0a4i-9000000000-27bbb5f9642306216a0bView 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-IT , positivesplash10-0aor-9500000000-3fdd9d17a169db5c58ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-493791dfdd428fc3bd6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-b2afc99d27edd18d7f29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-9500000000-5c3747866d41ab8df618View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-5cf478650fcc3a71b790View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-86832153dde465116f78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9600000000-2e90f09f2c87dfc45640View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-f32989f795eeceb8b692View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Blood
  • Colostrum
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Muscle
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Prostate Tissue
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal CortexExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified13.7-25.5 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified169+/-31 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • Trabi M, Keller M...
details
ColostrumDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
EpidermisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected and Quantified358+/-93 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified1321+/-351 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
MilkDetected and Quantified459 - 1410 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified73 +/- 5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified81 +/- 4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified79 +/- 4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified71 +/- 5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified72.22 +/- 16.17 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified64.41 +/- 31.44 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified90.15 +/- 25.33 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified1477-1826 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified315.07 +/- 23.69 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified345.85 +/- 38.4 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified375.31 +/- 38.29 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified292-487 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified456.74 +/- 30.58 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified590 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified67-111 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
OvaryExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified2-17 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified15+/-40 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Semimembranosus MuscleDetected and Quantified1139+/-246 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
SpleenExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified564+/-134 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
HMDB IDHMDB0000043
DrugBank IDDB06756
Phenol Explorer Compound IDNot Available
FooDB IDFDB009020
KNApSAcK IDC00007291
Chemspider ID242
KEGG Compound IDC00719
BioCyc IDBETAINE
BiGG ID35786
Wikipedia LinkTrimethylglycine
METLIN ID287
PubChem Compound247
PDB IDNot Available
ChEBI ID17750
References
Synthesis ReferenceMu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49.
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 ]
  2. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  3. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Energy production and conversion
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism (By similarity).
Gene Name:
ALDH7A1
Uniprot ID:
Q2KJC9
Molecular weight:
58582.0
Reactions
Betaine aldehyde + NAD + Water → Betaine + NADHdetails
General function:
Amino acid transport and metabolism
Specific function:
Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline (By similarity).
Gene Name:
BHMT
Uniprot ID:
Q5I597
Molecular weight:
44878.0
Reactions
Betaine + Homocysteine → Dimethylglycine + L-Methioninedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
E1BES2
Molecular weight:
65518.0
Reactions
Choline + Acceptor → Betaine + Reduced acceptordetails