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Showing metabocard for Betaine (BMDB0000043)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:18:53 UTC
Update Date2020-06-04 20:59:41 UTC
MCDB ID BMDB0000043
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
MOLSDFPDBSMILESInChI
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point293 - 301 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility611 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-96ab6e2136fe7e03b63a2016-09-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-feacc600820771d2a77b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-e5bbda9fb669945760622012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-c382759eab7d0a87ac272012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-a7beb42e6944181ae5d92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-1900000000-77fbc4a2b76030d536442012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-2941e4997f202293bf712012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-9b9e3cecb77ed4b40b7c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-27bbb5f9642306216a0b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-1900000000-82a41cbb0f697910b5772012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0aor-9500000000-9a0f1853188052d798c62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-066r-5900000000-a6291f86046f32ad3c812017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9200000000-709208d6782f1b5885012017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-a7beb42e6944181ae5d92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-77fbc4a2b76030d536442017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-2941e4997f202293bf712017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a2560fc2add75f79eadb2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-27bbb5f9642306216a0b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-b45353825d98488d752a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0aor-9500000000-3fdd9d17a169db5c58dd2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-493791dfdd428fc3bd6b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-b2afc99d27edd18d7f292017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-9500000000-5c3747866d41ab8df6182017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-5cf478650fcc3a71b7902017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-86832153dde465116f782017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9600000000-2e90f09f2c87dfc456402017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-f32989f795eeceb8b6922015-03-01View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified459 - 1410 uM details
Detected and Quantified73 +/- 5 uM details
Detected and Quantified81 +/- 4 uM details
Detected and Quantified79 +/- 4 uM details
Detected and Quantified71 +/- 5 uM details
Detected and Quantified72 +/- 16 uM details
Detected and Quantified64 +/- 31 uM details
Detected and Quantified90 +/- 25 uM details
HMDB IDHMDB0000043
DrugBank IDDB06756
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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.