Livestock Metabolome Database: Showing metabocard for Betaine (LMDB00015)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:30 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00015

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Betaine

Description

Betaine, (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

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

117.1463

Monoisotopic Molecular Weight

117.078978601

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

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9200000000-96ab6e2136fe7e03b63a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-feacc600820771d2a77b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-e5bbda9fb66994576062	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-c382759eab7d0a87ac27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-a7beb42e6944181ae5d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-1900000000-77fbc4a2b76030d53644	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9100000000-2941e4997f202293bf71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-9b9e3cecb77ed4b40b7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a4i-9000000000-27bbb5f9642306216a0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-1900000000-82a41cbb0f697910b577	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0aor-9500000000-9a0f1853188052d798c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-066r-5900000000-a6291f86046f32ad3c81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9200000000-709208d6782f1b588501	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-a7beb42e6944181ae5d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-77fbc4a2b76030d53644	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9100000000-2941e4997f202293bf71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-a2560fc2add75f79eadb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-27bbb5f9642306216a0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-b45353825d98488d752a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0aor-9500000000-3fdd9d17a169db5c58dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-493791dfdd428fc3bd6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3900000000-b2afc99d27edd18d7f29	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lk9-9500000000-5c3747866d41ab8df618	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5cf478650fcc3a71b790	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-86832153dde465116f78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-9600000000-2e90f09f2c87dfc45640	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9000000000-f32989f795eeceb8b692	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not 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

Biofluid	Status	Value	Condition	Species	Reference	Details
Bile acid	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Brain cortex	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Kidney	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Liver	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Lung	Detected but not Quantified	Not Applicable	Not Available	Porcine	23412987	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	25637742	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Porcine	24200563	details
Meat	Detected and Quantified	315.07 +/- 23.69 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	345.85 +/- 38.4 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	375.31 +/- 38.29 uM	Not Available	Bovine	20831251	details
Meat	Detected and Quantified	456.74 +/- 30.58 uM	Not Available	Bovine	20831251	details
Milk	Detected and Quantified	489-1263 uM	Not Available	Bovine	22098372	details
Milk	Detected and Quantified	459-1410 uM	Not Available	Bovine	20338431	details
Pancreas	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	24937646	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24477039	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	Trabi M, Keller M...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	19603403	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22673149	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Proximal colon	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Proximal colon	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Serum	Detected and Quantified	248.0184 +/- 79.9511 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	243.453 +/- 79.9188 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	253.299 +/- 85.4398 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	227.6428 +/- 67.6482 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	129.35 +/- 45.82 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	254.1759 +/- 97.9319 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	166.4172 +/- 42.0874 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	259.0429 +/- 93.1402 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	18989615	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Serum	Detected and Quantified	264.0873 +/- 86.7699 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	200.1745 +/- 74.5394 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	216.1433 +/- 68.8081 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	188.5828 +/- 43.5348 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	246.7355 +/- 84.2412 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	174.6864 +/- 45.3711 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	224.8171 +/- 53.8043 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	205.2348 +/- 68.453 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	315.5213 +/- 118.879 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	257.7187 +/- 70.2665 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	192.8701 +/- 55.0322 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	235.0852 +/- 68.5174 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	189.9565 +/- 56.6711 uM	Normal	Ovine	Goldansaz et al.,...	details
Synovial Fluid	Detected but not Quantified	Not Applicable	Not Available	Ovine	25283885	details
Urine	Detected and Quantified	116 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected and Quantified	705 umol/mmol creatinine	Not Available	Porcine	23741447	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Porcine	22661492	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Urine	Detected but not Quantified	Not Applicable	Not Available	Ovine	21142080	details
Vitreous Humour	Detected but not Quantified	Not Applicable	Not Available	Caprine	24845217	details

External Links

DrugBank ID

DB06756

HMDB ID

HMDB0000043

FooDB ID

FDB009020

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]

Showing metabocard for Betaine (LMDB00015)

Structure for LMDB00015 (Betaine)