Record Information
Version1.0
Created at2020-04-17 18:36:50 UTC
Updated at2020-12-07 19:10:56 UTC
CannabisDB IDCDB004788
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBetaine
DescriptionBetaine, also known as Bet or trimethylglycine, 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 is a moderately acidic compound (based on its pKa). Betaine exists in all eukaryotes, ranging from yeast to humans. In humans, betaine is involved in betaine metabolism. Betaine is a bland tasting compound. Outside of the human body, Betaine is found, on average, in the highest concentration within a few different foods, such as swamp cabbages, quinoa, and lambsquarters and in a lower concentration in common buckwheats, burdocks, and yellow zucchinis. Betaine has also been detected, but not quantified in, several different foods, such as lemon verbena, wasabis, endives, chickpea, and pomegranates. This could make betaine a potential biomarker for the consumption of these foods. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration (Wikipedia ). Betaine comes from either the diet or by the oxidation of choline. Betaine, with regard to humans, has been found to be associated with several diseases such as chronic renal failure, colorectal cancer, and alzheimer's disease; betaine has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and propionic acidemia. In an acute toxicology study in rats, death frequently occurred at doses equal to or greater than 10,000 mg/kg. 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 ). Betaine insufficiency is associated with metabolic syndrome, lipid disorders, and diabetes, and may have a role in vascular and other diseases (PMID: 20346934 ). Many reports have shown that betaine's therapeutic effectiveness is limited, and does not lower tHcy levels or prevent clinical symptoms . Betaine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight117.15
Monoisotopic Molecular Weight117.079
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-f32989f795eeceb8b692Spectrum
Predicted GC-MSBetaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fu-9200000000-96ab6e2136fe7e03b63aSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-feacc600820771d2a77bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-e5bbda9fb66994576062Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-c382759eab7d0a87ac27Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-a7beb42e6944181ae5d9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-1900000000-77fbc4a2b76030d53644Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9100000000-2941e4997f202293bf71Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-9b9e3cecb77ed4b40b7cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-27bbb5f9642306216a0bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-1900000000-82a41cbb0f697910b577Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0aor-9500000000-9a0f1853188052d798c6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-066r-5900000000-a6291f86046f32ad3c81Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9200000000-709208d6782f1b588501Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-a7beb42e6944181ae5d9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-77fbc4a2b76030d53644Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9100000000-2941e4997f202293bf71Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-a2560fc2add75f79eadbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-27bbb5f9642306216a0bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-b45353825d98488d752aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0aor-9500000000-3fdd9d17a169db5c58ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-493791dfdd428fc3bd6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-b2afc99d27edd18d7f29Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-9500000000-5c3747866d41ab8df618Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-5cf478650fcc3a71b790Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-86832153dde465116f78Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9600000000-2e90f09f2c87dfc45640Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Choline dehydrogenase, mitochondrialCHDH3p21.1Q8NE62 details
Alpha-aminoadipic semialdehyde dehydrogenaseALDH7A15q31P49419 details
Betaine--homocysteine S-methyltransferase 1BHMT5q14.1Q93088 details
S-methylmethionine--homocysteine S-methyltransferase BHMT2BHMT25q13Q9H2M3 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Sodium- and chloride-dependent betaine transporterSLC6A1212p13P48065 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Betaine--homocysteine S-methyltransferase 1BHMT5q14.1Q93088 details
S-methylmethionine--homocysteine S-methyltransferase BHMT2BHMT25q13Q9H2M3 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.143 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GabriolaDetected and Quantified0.0636 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Island HoneyDetected and Quantified0.141 mg/g dry wt
    • Jiamin Zheng, Yil...
details
QuadraDetected and Quantified0.0771 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi StarDetected and Quantified0.0811 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified0.089 mg/g dry wt
    • Jiamin Zheng, Yil...
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
General References
  1. 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. doi: 10.6091/ibj.1012.2012. [PubMed:22801281 ]
  2. 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. [PubMed:20346934 ]

Enzymes

General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
Not Available
Gene Name:
CHDH
Uniprot ID:
Q8NE62
Molecular weight:
65358.005
General function:
Involved in oxidoreductase activity
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.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
General function:
Involved in zinc ion binding
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.
Gene Name:
BHMT
Uniprot ID:
Q93088
Molecular weight:
44998.205
General function:
Involved in zinc ion binding
Specific function:
Involved in the regulation of homocysteine metabolism. Converts homocysteine to methionine using S-methylmethionine (SMM) as a methyl donor.
Gene Name:
BHMT2
Uniprot ID:
Q9H2M3
Molecular weight:
33166.69

Transporters

General function:
Involved in gamma-aminobutyric acid:sodium symporter ac
Specific function:
Transports betaine and GABA. May have a role in regulation of GABAergic transmission in the brain through the reuptake of GABA into presynaptic terminals, as well as in osmotic regulation.
Gene Name:
SLC6A12
Uniprot ID:
P48065
Molecular weight:
69367.655