Betaine (YMDB01516)

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Identification

YMDB ID

YMDB01516

Name

Betaine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Betaine (glycine betaine or trimethylglycine) is a methylated derivative of glycine synthetized from choline. It is a very efficient osmolyte found in a wide range of bacteria and plants, where it is accumulated at high cytoplasmic concentrations in response to osmotic stress, to act as an osmoprotectant. Many organisms, including fungi, are also able to catabolize glycine betaine, using it as a sole source for both carbon and nitrogen. [Biocyc PWY-3721 and PWY-3661]

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

107-43-7

Weight

Average: 117.1463
Monoisotopic: 117.078978601

InChI Key

KWIUHFFTVRNATP-UHFFFAOYSA-N

InChI

InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3

IUPAC Name

2-(trimethylazaniumyl)acetate

Traditional IUPAC Name

(trimethylammonio)acetate

Chemical Formula

C₅H₁₁NO₂

SMILES

C[N+](C)(C)CC([O-])=O

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

Charge

Melting point

293 °C

Experimental Properties

Property	Value	Reference
Water Solubility	611 mg/mL at 19 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	1.86 g/L	ALOGPS
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Bland	FDB009020

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
26 ± 0 µM	grape juice	anaerobic	Brewer's yeast	Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here

Spectra

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

References

References:

Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page

Synthesis Reference:

Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49.

External Links:

Resource	Link
CHEBI ID	17750
HMDB ID	HMDB00043
Pubchem Compound ID	247
Kegg ID	C00719
ChemSpider ID	242
FOODB ID	FDB009020
Wikipedia ID	Trimethylglycine
BioCyc ID	BETAINE

Structure for #<Compound:0xaec98b60>