Milk Composition Database: Showing metabocard for Betaine (BMDB0000043)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:53 UTC

Update Date

2020-06-04 20:59:41 UTC

MCDB ID

BMDB0000043

Secondary Accession Numbers

BMDB00043

Metabolite Identification

Common Name

Betaine

Description

Betaine, 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

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 )

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9200000000-96ab6e2136fe7e03b63a	2016-09-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-feacc600820771d2a77b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-e5bbda9fb66994576062	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9000000000-c382759eab7d0a87ac27	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-a7beb42e6944181ae5d9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-1900000000-77fbc4a2b76030d53644	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-9100000000-2941e4997f202293bf71	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-9000000000-9b9e3cecb77ed4b40b7c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a4i-9000000000-27bbb5f9642306216a0b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-014i-1900000000-82a41cbb0f697910b577	2012-08-31	View Spectrum
LC-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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-066r-5900000000-a6291f86046f32ad3c81	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9200000000-709208d6782f1b588501	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-a7beb42e6944181ae5d9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-77fbc4a2b76030d53644	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9100000000-2941e4997f202293bf71	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-a2560fc2add75f79eadb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-27bbb5f9642306216a0b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-b45353825d98488d752a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0aor-9500000000-3fdd9d17a169db5c58dd	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-493791dfdd428fc3bd6b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3900000000-b2afc99d27edd18d7f29	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lk9-9500000000-5c3747866d41ab8df618	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5cf478650fcc3a71b790	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-86832153dde465116f78	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-9600000000-2e90f09f2c87dfc45640	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9000000000-f32989f795eeceb8b692	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	459 - 1410 uM	PMID: 20338431	details
Detected and Quantified	73 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	81 +/- 4 uM	PMID: 30994344	details
Detected and Quantified	79 +/- 4 uM	PMID: 30994344	details
Detected and Quantified	71 +/- 5 uM	PMID: 30994344	details
Detected and Quantified	72 +/- 16 uM	PMID: 29642378	details
Detected and Quantified	64 +/- 31 uM	PMID: 29642378	details
Detected and Quantified	90 +/- 25 uM	PMID: 29642378	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

Synthesis Reference

Mu, 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

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 ]
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 ]
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.

Showing metabocard for Betaine (BMDB0000043)

Structure for BMDB0000043 (Betaine)