Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:18:53 UTC |
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Update Date | 2020-06-04 20:59:41 UTC |
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MCDB ID | BMDB0000043 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Betaine |
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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. |
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Structure | |
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Synonyms | Value | Source |
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(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 |
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Chemical Formula | C5H11NO2 |
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Average Molecular Weight | 117.1463 |
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Monoisotopic Molecular Weight | 117.078978601 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 107-43-7 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 |
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InChI Key | KWIUHFFTVRNATP-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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 |
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Predicted Properties | Not Available |
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Spectra |
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Concentrations |
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Detected and Quantified | 459 - 1410 uM | | | details | Detected and Quantified | 73 +/- 5 uM | | | details | Detected and Quantified | 81 +/- 4 uM | | | details | Detected and Quantified | 79 +/- 4 uM | | | details | Detected and Quantified | 71 +/- 5 uM | | | details | Detected and Quantified | 72 +/- 16 uM | | | details | Detected and Quantified | 64 +/- 31 uM | | | details | Detected and Quantified | 90 +/- 25 uM | | | details |
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External Links |
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HMDB ID | HMDB0000043 |
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DrugBank ID | DB06756 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB009020 |
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KNApSAcK ID | C00007291 |
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Chemspider ID | 242 |
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KEGG Compound ID | C00719 |
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BioCyc ID | BETAINE |
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BiGG ID | 35786 |
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Wikipedia Link | Trimethylglycine |
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METLIN ID | 287 |
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PubChem Compound | 247 |
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PDB ID | Not Available |
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ChEBI ID | 17750 |
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References |
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Synthesis Reference | Mu, Yun; Guo, Xiao-hui. Improved process for preparation of betaine. Huaxue Yu Shengwu Gongcheng (2005), 22(7), 48-49. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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.
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