Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-19 03:09:31 UTC |
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Update Date | 2016-10-28 10:02:07 UTC |
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Accession Number | CHEM009690 |
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Identification |
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Common Name | Ethanaminium, 2-hydroxy-N,N,N-trimethyl-, hydroxide |
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Class | Small Molecule |
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Description | A basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. |
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Contaminant Sources | - Cosmetic Chemicals
- FooDB Chemicals
- HMDB Contaminants - Feces
- HMDB Contaminants - Urine
- HPV EPA Chemicals
- ToxCast & Tox21 Chemicals
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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Bilineurine | ChEBI | CHOLINE ion | ChEBI | N,N,N-Trimethylethanol-ammonium | ChEBI | N-Trimethylethanolamine | ChEBI | Trimethylethanolamine | ChEBI | Choline cation | Kegg | (2-Hydroxyethyl)trimethyl ammonium | HMDB | (2-Hydroxyethyl)trimethylammonium | HMDB | (beta-Hydroxyethyl)trimethylammonium | HMDB | 2-Hydroxy-N,N,N-trimethyl-ethanaminium | HMDB | 2-Hydroxy-N,N,N-trimethylethanaminium | HMDB | Biocolina | HMDB | Biocoline | HMDB | Cholinum | HMDB | Hepacholine | HMDB | Hormocline | HMDB | Lipotril | HMDB | N,N,N-Trimethylethanolammonium | HMDB | Neocolina | HMDB | Paresan | HMDB | Choline O-sulfate | HMDB | Citrate, choline | HMDB | Fagine | HMDB | Hydroxide, choline | HMDB | Vidine | HMDB | Bursine | HMDB | Chloride, choline | HMDB | Choline chloride | HMDB | Choline citrate | HMDB | Bitartrate, choline | HMDB | Choline bitartrate | HMDB | Choline hydroxide | HMDB | Choline O sulfate | HMDB | O-Sulfate, choline | HMDB |
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Chemical Formula | C5H14NO |
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Average Molecular Mass | 104.171 g/mol |
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Monoisotopic Mass | 104.108 g/mol |
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CAS Registry Number | 123-41-1 |
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IUPAC Name | (2-hydroxyethyl)trimethylazanium |
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Traditional Name | choline |
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SMILES | C[N+](C)(C)CCO |
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InChI Identifier | InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 |
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InChI Key | OEYIOHPDSNJKLS-UHFFFAOYSA-N |
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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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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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 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-05g0-9300000000-ca1b0086d4882b00b395 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0a4i-0900000000-ea6f9c1150759c5be6c7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4i-1900000000-cadf16d18f093e9b19d6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0bt9-9100000000-a2c328b7da5435b8e467 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udi-0900000000-6a7b57dbdf4560721722 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-0udi-5900000000-87fdeef5275a74e78348 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0w29-5900000000-9b79cc5ff3b1ce17deb1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-9200000000-fe62d5a4fbf492493d60 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-0udi-3900000000-0b37e63e9c6b14a2e397 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-0900000000-6a7b57dbdf4560721722 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0udi-5900000000-87fdeef5275a74e78348 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0pb9-1900000000-391c1b7859a03e776123 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-2900000000-43b0f930ff04f7a48a59 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udr-9400000000-ab7cc75a8e0d3cc49449 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-9000000000-0b94edfd44e38b20b8d3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-9100000000-a738404b52e2f1f6fec1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9000000000-c596e40769889223b3dd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-c6fab16d1790976560b5 | 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 | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C 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 |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00122 |
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HMDB ID | HMDB0000097 |
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FooDB ID | FDB000710 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00007298 |
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BiGG ID | 33910 |
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BioCyc ID | CHOLINE |
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METLIN ID | 56 |
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PDB ID | Not Available |
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Wikipedia Link | Choline |
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Chemspider ID | 299 |
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ChEBI ID | 15354 |
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PubChem Compound ID | 305 |
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Kegg Compound ID | C00114 |
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YMDB ID | YMDB00227 |
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ECMDB ID | ECMDB00097 |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. 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. | 2. Zeisel SH, Char D, Sheard NF: Choline, phosphatidylcholine and sphingomyelin in human and bovine milk and infant formulas. J Nutr. 1986 Jan;116(1):50-8. doi: 10.1093/jn/116.1.50. | 3. 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. | 4. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. | 5. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. | 6. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. | 7. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. | 8. 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. | 9. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 | 10. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) | 11. 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. | 12. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. | 13. Kohlmeier M, da Costa KA, Fischer LM, Zeisel SH: Genetic variation of folate-mediated one-carbon transfer pathway predicts susceptibility to choline deficiency in humans. Proc Natl Acad Sci U S A. 2005 Nov 1;102(44):16025-30. Epub 2005 Oct 18. | 14. Babb SM, Ke Y, Lange N, Kaufman MJ, Renshaw PF, Cohen BM: Oral choline increases choline metabolites in human brain. Psychiatry Res. 2004 Jan 15;130(1):1-9. | 15. Pal K, Sharma U, Gupta DK, Pratap A, Jagannathan NR: Metabolite profile of cerebrospinal fluid in patients with spina bifida: a proton magnetic resonance spectroscopy study. Spine (Phila Pa 1976). 2005 Feb 1;30(3):E68-72. | 16. Farsad M, Schiavina R, Castellucci P, Nanni C, Corti B, Martorana G, Canini R, Grigioni W, Boschi S, Marengo M, Pettinato C, Salizzoni E, Monetti N, Franchi R, Fanti S: Detection and localization of prostate cancer: correlation of (11)C-choline PET/CT with histopathologic step-section analysis. J Nucl Med. 2005 Oct;46(10):1642-9. | 17. Yanagawa T, Watanabe H, Inoue T, Ahmed AR, Tomiyoshi K, Shinozaki T, Oriuchi N, Endo K, Takagishi K: Carbon-11 choline positron emission tomography in musculoskeletal tumors: comparison with fluorine-18 fluorodeoxyglucose positron emission tomography. J Comput Assist Tomogr. 2003 Mar-Apr;27(2):175-82. | 18. Zeisel SH: Nutritional importance of choline for brain development. J Am Coll Nutr. 2004 Dec;23(6 Suppl):621S-626S. | 19. Walter A, Korth U, Hilgert M, Hartmann J, Weichel O, Hilgert M, Fassbender K, Schmitt A, Klein J: Glycerophosphocholine is elevated in cerebrospinal fluid of Alzheimer patients. Neurobiol Aging. 2004 Nov-Dec;25(10):1299-303. | 20. Garner SC, Chou SC, Mar MH, Coleman RA, Zeisel SH: Characterization of choline metabolism and secretion by human placental trophoblasts in culture. Biochim Biophys Acta. 1993 Jul 1;1168(3):358-64. | 21. Rumpel H, Ho GL, Chan LL, Lim WE, Chong VF: Concomitant diminishing magnetization-transfer effect and increasing choline level in radiation-induced temporal-lobe changes. Australas Radiol. 2002 Sep;46(3):340-4. | 22. Zeisel SH: Choline: critical role during fetal development and dietary requirements in adults. Annu Rev Nutr. 2006;26:229-50. | 23. Ozarda Ilcol Y, Ozyurt G, Kilicturgay S, Uncu G, Ulus IH: The decline in serum choline concentration in humans during and after surgery is associated with the elevation of cortisol, adrenocorticotropic hormone, prolactin and beta-endorphin concentrations. Neurosci Lett. 2002 May 10;324(1):41-4. | 24. Van Hove JL, Lazeyras F, Zeisel SH, Bottiglieri T, Hyland K, Charles HC, Gray L, Jaeken J, Kahler SG: One-methyl group metabolism in non-ketotic hyperglycinaemia: mildly elevated cerebrospinal fluid homocysteine levels. J Inherit Metab Dis. 1998 Dec;21(8):799-811. | 25. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. | 26. Chen CY, Li CW, Kuo YT, Jaw TS, Wu DK, Jao JC, Hsu JS, Liu GC: Early response of hepatocellular carcinoma to transcatheter arterial chemoembolization: choline levels and MR diffusion constants--initial experience. Radiology. 2006 May;239(2):448-56. Epub 2006 Mar 28. | 27. Buchman AL, Ament ME, Sohel M, Dubin M, Jenden DJ, Roch M, Pownall H, Farley W, Awal M, Ahn C: Choline deficiency causes reversible hepatic abnormalities in patients receiving parenteral nutrition: proof of a human choline requirement: a placebo-controlled trial. JPEN J Parenter Enteral Nutr. 2001 Sep-Oct;25(5):260-8. | 28. da Costa KA, Badea M, Fischer LM, Zeisel SH: Elevated serum creatine phosphokinase in choline-deficient humans: mechanistic studies in C2C12 mouse myoblasts. Am J Clin Nutr. 2004 Jul;80(1):163-70. | 29. Katz-Brull R, Margalit R, Degani H: Differential routing of choline in implanted breast cancer and normal organs. Magn Reson Med. 2001 Jul;46(1):31-8. | 30. Ilcol YO, Donmez O, Yavuz M, Dilek K, Yurtkuran M, Ulus IH: Free choline and phospholipid-bound choline concentrations in serum and dialysate during peritoneal dialysis in children and adults. Clin Biochem. 2002 Jun;35(4):307-13. | 31. Jacob RA, Jenden DJ, Allman-Farinelli MA, Swendseid ME: Folate nutriture alters choline status of women and men fed low choline diets. J Nutr. 1999 Mar;129(3):712-7. | 32. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. | 33. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630 | 34. https://www.ncbi.nlm.nih.gov/pubmed/?term=12826235 | 35. https://www.ncbi.nlm.nih.gov/pubmed/?term=12946691 | 36. https://www.ncbi.nlm.nih.gov/pubmed/?term=14972364 | 37. https://www.ncbi.nlm.nih.gov/pubmed/?term=16210714 | 38. https://www.ncbi.nlm.nih.gov/pubmed/?term=17087106 | 39. https://www.ncbi.nlm.nih.gov/pubmed/?term=17283071 | 40. https://www.ncbi.nlm.nih.gov/pubmed/?term=17344490 | 41. https://www.ncbi.nlm.nih.gov/pubmed/?term=18204095 | 42. https://www.ncbi.nlm.nih.gov/pubmed/?term=18230680 | 43. https://www.ncbi.nlm.nih.gov/pubmed/?term=18786517 | 44. https://www.ncbi.nlm.nih.gov/pubmed/?term=18786520 | 45. https://www.ncbi.nlm.nih.gov/pubmed/?term=19246089 | 46. https://www.ncbi.nlm.nih.gov/pubmed/?term=20038853 | 47. https://www.ncbi.nlm.nih.gov/pubmed/?term=20446114 | 48. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225 | 49. https://www.ncbi.nlm.nih.gov/pubmed/?term=22961562 | 50. https://www.ncbi.nlm.nih.gov/pubmed/?term=23095202 | 51. https://www.ncbi.nlm.nih.gov/pubmed/?term=23616508 | 52. https://www.ncbi.nlm.nih.gov/pubmed/?term=23637565 | 53. https://www.ncbi.nlm.nih.gov/pubmed/?term=23733158 | 54. https://www.ncbi.nlm.nih.gov/pubmed/?term=6420466 | 55. https://www.ncbi.nlm.nih.gov/pubmed/?term=7590654 | 56. https://www.ncbi.nlm.nih.gov/pubmed/?term=9517478 |
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