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| Identification |
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| YMDB ID | YMDB00227 |
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| Name | Choline |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Choline, also known as bilineurine or choline ion, belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. Choline is an extremely weak basic (essentially neutral) compound (based on its pKa). Choline exists in all living species, ranging from bacteria to humans. Within yeast, choline participates in a number of enzymatic reactions. In particular, glycerol 3-phosphate and choline can be biosynthesized from glycerophosphocholine through its interaction with the enzyme glycerophosphodiester phosphodiesterase GDE1. In addition, choline can be converted into phosphorylcholine through the action of the enzyme choline kinase. In yeast, choline is involved in the metabolic pathway called the lysolipid incorporation into er pc(18:1(9z)/18:1(9z)) pathway. |
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| Structure | |
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| Synonyms | - (2-Hydroxyethyl)trimethyl ammonium
- (2-Hydroxyethyl)trimethylammonium
- (beta-hydroxyethyl)trimethylammonium
- 2-hydroxy-N,N,N-trimethyl-ethanaminium
- 2-hydroxy-N,N,N-trimethylethanaminium
- Bilineurine
- Biocolina
- Biocoline
- Choline
- Choline cation
- Choline ion
- Cholinum
- Hepacholine
- Hormocline
- Lipotril
- N,N,N-trimethylethanol-ammonium
- N,N,N-trimethylethanolammonium
- Neocolina
- Paresan
- N-Trimethylethanolamine
- Trimethylethanolamine
- Choline O-sulfate
- Citrate, choline
- Fagine
- Hydroxide, choline
- Vidine
- Bursine
- Chloride, choline
- Choline chloride
- Choline citrate
- Bitartrate, choline
- Choline bitartrate
- Choline hydroxide
- Choline O sulfate
- O-Sulfate, choline
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| CAS number | 62-49-7 |
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| Weight | Average: 104.1708
Monoisotopic: 104.107539075 |
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| InChI Key | OEYIOHPDSNJKLS-UHFFFAOYSA-N |
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| InChI | InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 |
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| IUPAC Name | (2-hydroxyethyl)trimethylazanium |
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| Traditional IUPAC Name | choline |
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| Chemical Formula | C5H14NO |
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| SMILES | [H]OC([H])([H])C([H])([H])[N+](C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. |
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| Kingdom | Organic compounds |
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| Super Class | Organic nitrogen compounds |
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| Class | Organonitrogen compounds |
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| Sub Class | Quaternary ammonium salts |
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| Direct Parent | Cholines |
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| Alternative Parents | |
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| Substituents | - Choline
- Tetraalkylammonium salt
- 1,2-aminoalcohol
- Alkanolamine
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organic salt
- Primary alcohol
- Organooxygen compound
- Amine
- Alcohol
- Organic cation
- 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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| Charge | 1 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | - extracellular
- cell envelope
- cytoplasm
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | | Choline metabolism | PW002494 |    | | Glycerophospholipid metabolism | PW002493 |    | | Lysolipid incorporation into ER | PW002532 |    | | Lysolipid incorporation into ER PC(10:0/10:0) | PW002780 |    | | Lysolipid incorporation into ER PC(14:0/14:0) | PW002783 |    |
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| KEGG Pathways | | Glycerophospholipid metabolism | ec00564 |  | | Glycine, serine and threonine metabolism | ec00260 |  |
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| SMPDB Reactions | |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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| 970 ± 0 µM | hops, malted barley | anaerobic | Baker's yeast | Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page | | 547 ± 0 µM | grape juice | anaerobic | Baker'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 |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05fr-9100000000-69389426dd865af031f9 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-05g0-9300000000-ca1b0086d4882b00b395 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-0900000000-ea6f9c1150759c5be6c7 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-1900000000-cadf16d18f093e9b19d6 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0bt9-9100000000-a2c328b7da5435b8e467 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0900000000-6a7b57dbdf4560721722 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-0udi-5900000000-87fdeef5275a74e78348 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0w29-5900000000-9b79cc5ff3b1ce17deb1 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-9200000000-fe62d5a4fbf492493d60 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-0udi-3900000000-0b37e63e9c6b14a2e397 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0900000000-6a7b57dbdf4560721722 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-5900000000-87fdeef5275a74e78348 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0pb9-1900000000-391c1b7859a03e776123 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-2900000000-43b0f930ff04f7a48a59 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udr-9400000000-ab7cc75a8e0d3cc49449 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-9000000000-0b94edfd44e38b20b8d3 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-9100000000-a738404b52e2f1f6fec1 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9000000000-c596e40769889223b3dd | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-c6fab16d1790976560b5 | JSpectraViewer | | 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 | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C 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 |
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| References |
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| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- McMaster, C. R., Bell, R. M. (1994). "Phosphatidylcholine biosynthesis in Saccharomyces cerevisiae. Regulatory insights from studies employing null and chimeric sn-1,2-diacylglycerol choline- and ethanolaminephosphotransferases." J Biol Chem 269:28010-28016.7961735
- Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
- 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
- Rose, K., Rudge, S. A., Frohman, M. A., Morris, A. J., Engebrecht, J. (1995). "Phospholipase D signaling is essential for meiosis." Proc Natl Acad Sci U S A 92:12151-12155.8618862
- Fisher, E., Almaguer, C., Holic, R., Griac, P., Patton-Vogt, J. (2005). "Glycerophosphocholine-dependent growth requires Gde1p (YPL110c) and Git1p in Saccharomyces cerevisiae." J Biol Chem 280:36110-36117.16141200
- Kim, K., Kim, K. H., Storey, M. K., Voelker, D. R., Carman, G. M. (1999). "Isolation and characterization of the Saccharomyces cerevisiae EKI1 gene encoding ethanolamine kinase." J Biol Chem 274:14857-14866.10329685
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| Synthesis Reference: | Hasegawa, Yoichi; Hyoda, Shunji; Sawada, Hirotoshi; Baba, Masakatsu. Preparation of high-purity organic carboxylic acid choline salts and choline. Jpn. Kokai Tokkyo Koho (1999), 9 pp. |
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| External Links: | |
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