Cannabis Compound Database: Showing Compound Card for Betaine (CDB004788)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (4)transporters (1) Show 7 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:36:50 UTC

Updated at

2022-12-13 23:36:26 UTC

CannabisDB ID

CDB004788

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Betaine

Description

Betaine, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Trimethylammoniumyl)acetate	ChEBI
1-Carboxy-N,N,N-trimethylmethanaminium inner salt	ChEBI
2-N,N,N-Trimethylammonio acetate	ChEBI
Abromine	ChEBI
Acidol	ChEBI
Bet	ChEBI
N,N,N-Trimethylammonioacetate	ChEBI
N,N,N-Trimethylglycine	ChEBI
Trimethylaminoacetate	ChEBI
Trimethylammonioacetate	ChEBI
Trimethylglycine	ChEBI
Trimethylglycocoll	ChEBI
Glycine betaine	Kegg
Cystadane	Kegg
(Trimethylammoniumyl)acetic acid	Generator
2-N,N,N-Trimethylammonio acetic acid	Generator
N,N,N-Trimethylammonioacetic acid	Generator
Trimethylaminoacetic acid	Generator
Trimethylammonioacetic acid	Generator
(Carboxymethyl)trimethylammonium hydroxide inner salt	HMDB
(Trimethylammonio)acetate	HMDB
1-Carboxy-N,N,N-trimethyl-methanaminium	HMDB
1-Carboxy-N,N,N-trimethyl-methanaminium hydroxide	HMDB
a-Earleine	HMDB
alpha-Earleine	HMDB
Aminocoat	HMDB
Betafin	HMDB
Betafin BCR	HMDB
Betafin BP	HMDB
Ektasolve ee	HMDB
FinnStim	HMDB
Glycocoll betaine	HMDB
Glycylbetaine	HMDB
Greenstim	HMDB
Loramine amb 13	HMDB
Loramine amb-13	HMDB
Lycine	HMDB
Oxyneurine	HMDB
Rubrine C	HMDB
Trimethylbetaine glycine	HMDB
Acidin pepsin	HMDB
Beaufour brand OF betaine citrate	HMDB
Byk brand OF betaine phosphate	HMDB
Fournier brand OF betaine ascorbate and hydrate	HMDB
Hydrochloride, betaine	HMDB
Logeais brand OF betaine cyclobutyrate	HMDB
Novobetaine	HMDB
Betaine hydrochloride	HMDB
Betaine orphan brand	HMDB
Boizot brand OF betaine aspartate	HMDB
C.B.B.	HMDB
Citrate de bétaïne upsa	HMDB
Scorbo-bétaïne	HMDB
Stea-16	HMDB
Stea16	HMDB
Acidin-pepsin	HMDB
Citrate de bétaïne beaufour	HMDB
Orphan brand OF betaine	HMDB
Scorbo bétaïne	HMDB
AcidinPepsin	HMDB
Betaine, glycine	HMDB
Hepastyl	HMDB
Scorbobétaïne	HMDB
UPSA brand OF betaine citrate	HMDB
Stea 16	HMDB
Betaine	ChEBI

Chemical Formula

C₅H₁₁NO₂

Average Molecular Weight

117.15

Monoisotopic Molecular Weight

117.079

IUPAC Name

2-(trimethylazaniumyl)acetate

Traditional Name

(trimethylammonio)acetate

CAS Registry Number

107-43-7

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 Key

KWIUHFFTVRNATP-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:17750 )
amino-acid betaine (CHEBI:17750 )
a methylated methyl acceptor (BETAINE )

Ontology

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Osmolyte

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	293 - 301 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	611 mg/mL at 19 °C	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.7	ALOGPS
logP	-4.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.82 m³·mol⁻¹	ChemAxon
Polarizability	12.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9000000000-f32989f795eeceb8b692	2015-03-01	View Spectrum
Predicted GC-MS	Betaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fu-9200000000-96ab6e2136fe7e03b63a	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-feacc600820771d2a77b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-e5bbda9fb66994576062	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-c382759eab7d0a87ac27	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-a7beb42e6944181ae5d9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-1900000000-77fbc4a2b76030d53644	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9100000000-2941e4997f202293bf71	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-9b9e3cecb77ed4b40b7c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a4i-9000000000-27bbb5f9642306216a0b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-1900000000-82a41cbb0f697910b577	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0aor-9500000000-9a0f1853188052d798c6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-066r-5900000000-a6291f86046f32ad3c81	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9200000000-709208d6782f1b588501	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-a7beb42e6944181ae5d9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-77fbc4a2b76030d53644	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9100000000-2941e4997f202293bf71	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-a2560fc2add75f79eadb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-27bbb5f9642306216a0b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-b45353825d98488d752a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0aor-9500000000-3fdd9d17a169db5c58dd	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-493791dfdd428fc3bd6b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3900000000-b2afc99d27edd18d7f29	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lk9-9500000000-5c3747866d41ab8df618	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5cf478650fcc3a71b790	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-86832153dde465116f78	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-9600000000-2e90f09f2c87dfc45640	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycine and Serine Metabolism
Betaine Metabolism
Methionine Metabolism
Cystathionine Beta-Synthase Deficiency		Not Available
Hypermethioninemia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Choline dehydrogenase, mitochondrial	CHDH	3p21.1	Q8NE62	details
Alpha-aminoadipic semialdehyde dehydrogenase	ALDH7A1	5q31	P49419	details
Betaine--homocysteine S-methyltransferase 1	BHMT	5q14.1	Q93088	details
S-methylmethionine--homocysteine S-methyltransferase BHMT2	BHMT2	5q13	Q9H2M3	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sodium- and chloride-dependent betaine transporter	SLC6A12	12p13	P48065	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Betaine--homocysteine S-methyltransferase 1	BHMT	5q14.1	Q93088	details
S-methylmethionine--homocysteine S-methyltransferase BHMT2	BHMT2	5q13	Q9H2M3	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0168 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00745 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.0165 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.00903 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00950 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0104 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0000043

DrugBank ID

DB06756

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17750

References

General References

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 ]
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

Enzyme Details

1. Choline dehydrogenase, mitochondrial

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

Enzyme Details

2. Alpha-aminoadipic semialdehyde dehydrogenase

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

Enzyme Details

3. Betaine--homocysteine S-methyltransferase 1

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

Enzyme Details

4. S-methylmethionine--homocysteine S-methyltransferase BHMT2

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

Enzyme Details

1. Sodium- and chloride-dependent betaine transporter

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

Showing Compound Card for Betaine (CDB004788)

Structure for CDB004788 (Betaine)

Enzymes

Transporters