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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:47:44 UTC |
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Update Date | 2020-06-04 20:32:23 UTC |
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BMDB ID | BMDB0001565 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Phosphorylcholine |
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Description | Phosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Phosphorylcholine is possibly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphorylcholine exists in all living species, ranging from bacteria to humans. Phosphorylcholine participates in a number of enzymatic reactions, within cattle. In particular, Cytidine triphosphate and phosphorylcholine can be converted into CDP-choline; which is catalyzed by the enzyme choline-phosphate cytidylyltransferase. In addition, Phosphorylcholine can be biosynthesized from choline; which is mediated by the enzyme choline/ethanolamine kinase. In cattle, phosphorylcholine is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/16:0) pathway. |
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Structure | |
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Synonyms | Value | Source |
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Choline phosphate | ChEBI | CHOP | ChEBI | N-Trimethyl-2-aminoethylphosphonate | ChEBI | O-Phosphocholine | ChEBI | Phosphoryl-choline | ChEBI | Trimethyl(2-(phosphonooxy)ethyl)ammonium | ChEBI | Phosphocholine | Kegg | Choline phosphoric acid | Generator | N-Trimethyl-2-aminoethylphosphonic acid | Generator | Chloride, phosphorylcholine | HMDB | Phosphate, choline | HMDB | Phosphorylcholine chloride | HMDB | Phosphate chloride, choline | HMDB | Chloride, choline phosphate | HMDB | Choline chloride dihydrogen phosphate | HMDB | Choline phosphate chloride | HMDB |
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Chemical Formula | C5H15NO4P |
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Average Molecular Weight | 184.1507 |
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Monoisotopic Molecular Weight | 184.073869485 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 3616-04-4 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1 |
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InChI Key | YHHSONZFOIEMCP-UHFFFAOYSA-O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. |
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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 | Phosphocholines |
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Alternative Parents | |
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Substituents | - Phosphocholine
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Tetraalkylammonium salt
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Amine
- Organic cation
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Brain
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Milk
- Placenta
- Platelet
- Testis
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Pathways | |
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Normal Concentrations |
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Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 1658 +/- 593 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 72.12 +/- 59.74 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 143 - 1355 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 183 - 941 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30.83 +/- 34.97 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 44.14 +/- 32.01 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 122 +/- 8 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 123 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 116 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 120 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 1058 +/- 234 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0001565 |
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DrugBank ID | DB03945 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031111 |
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KNApSAcK ID | C00007299 |
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Chemspider ID | 989 |
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KEGG Compound ID | C00588 |
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BioCyc ID | PHOSPHORYL-CHOLINE |
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BiGG ID | 48308 |
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Wikipedia Link | Phosphorylcholine |
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METLIN ID | 6326 |
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PubChem Compound | 1014 |
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PDB ID | Not Available |
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ChEBI ID | 18132 |
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References |
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Synthesis Reference | Vijeeta, T.; Reddy, J. R. C.; Rao, B. V. S. K.; Karuna, M. S. L.; Prasad, R. B. N. Phospholipase-mediated preparation of 1-ricinoleoyl-2-acyl-sn- glycero-3-phosphocholine from soya and egg phosphatidylcholine. Biotechnology Letters (2004), 26(13), 1077-10 |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
- 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. [PubMed:22098372 ]
- Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
- 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. [PubMed:25087032 ]
- 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. [PubMed:23738862 ]
- 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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