Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2010-03-18 16:07:50 UTC |
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Update Date | 2022-03-07 02:51:30 UTC |
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HMDB ID | HMDB0013452 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(O-22:1(13Z)/22:2(13Z,16Z)) |
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Description | PC(O-22:1(13Z)/22:2(13Z,16Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(O-22:1(13Z)/22:2(13Z,16Z)), in particular, consists of one chain of Erucyl alcohol at the C-1 position and one chain of docosadienoic acid at the C-2 position. The Erucyl alcohol moiety is derived from Rapeseed oil, while the docosadienoic acid moiety is derived from animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. |
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Structure | CCCCCCCC\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C52H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,20-23,51H,6-14,16,18-19,24-50H2,1-5H3/b17-15-,22-20-,23-21-/t51-/m1/s1 |
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Synonyms | Value | Source |
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1-Erucyl-2-docosadienoyl-sn-glycero-3-phosphocholine | HMDB | Gpcho(22:1/22:2) | HMDB | Gpcho(22:1n9/22:2n6) | HMDB | Gpcho(22:1W9/22:2W6) | HMDB | Gpcho(44:3) | HMDB | Lecithin | HMDB | PC Ae C44:3 | HMDB | PC(22:1/22:2) | HMDB | PC(22:1n9/22:2n6) | HMDB | PC(22:1W9/22:2W6) | HMDB | PC(44:3) | HMDB | PC(O-44:3) | HMDB | Phosphatidylcholine(22:1/22:2) | HMDB | Phosphatidylcholine(22:1n9/22:2n6) | HMDB | Phosphatidylcholine(22:1W9/22:2W6) | HMDB | Phosphatidylcholine(44:3) | HMDB | 1-(13Z-Docosenyl)-2-(13Z,16Z-docosadienoyl)-sn-glycero-3-phosphocholine | HMDB | PC(o-22:1(13Z)/22:2(13Z,16Z)) | Lipid Annotator |
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Chemical Formula | C52H100NO7P |
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Average Molecular Weight | 882.3267 |
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Monoisotopic Molecular Weight | 881.723741071 |
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IUPAC Name | (2-{[(2R)-3-[(13Z)-docos-13-en-1-yloxy]-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-3-[(13Z)-docos-13-en-1-yloxy]-2-[(13Z,16Z)-docosa-13,16-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCC\C=C/CCCCCCCCCCCCOC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C52H100NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-47-57-49-51(50-59-61(55,56)58-48-46-53(3,4)5)60-52(54)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,20-23,51H,6-14,16,18-19,24-50H2,1-5H3/b17-15-,22-20-,23-21-/t51-/m1/s1 |
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InChI Key | VCODWVLGDPOACA-DRGSQYEJSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphocholines |
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Direct Parent | 1-alkyl,2-acylglycero-3-phosphocholines |
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Alternative Parents | |
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Substituents | - 1-alkyl,2-acylglycero-3-phosphocholine
- Phosphocholine
- Fatty acid ester
- Dialkyl phosphate
- Glycerol ether
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Fatty acyl
- Alkyl phosphate
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- Organic nitrogen compound
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- 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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Physiological effect | |
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Disposition | Biological locationRoute of exposureSourceEndogenousExogenousFood- Food (HMDB: HMDB0013452)
Animal originMilk and milk productUnfermented milk- Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
- Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
- Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
- Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 10V, Positive-QTOF | splash10-0019-9105031230-8ac1e5f24a5c527f32e3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 20V, Positive-QTOF | splash10-0cei-5309021210-42e5c8d6c14d4675f85e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 40V, Positive-QTOF | splash10-05nr-9018003110-46c70a6ed4470cd911fb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 10V, Negative-QTOF | splash10-001r-0007000290-3f3a5f0be83f7ebcdf88 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 20V, Negative-QTOF | splash10-00bi-2019200630-ae7ecbfd4f323ccdc68a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 40V, Negative-QTOF | splash10-05p9-4019200000-aa4951f16661fed11de0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 10V, Positive-QTOF | splash10-001i-0000000090-96e9e570336d9ee74713 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 20V, Positive-QTOF | splash10-001i-0000000090-96e9e570336d9ee74713 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 40V, Positive-QTOF | splash10-001i-1900061070-5d86dc6afcf6786a42aa | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 10V, Negative-QTOF | splash10-014i-0000000009-ca3f7b3580cfc8035037 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 20V, Negative-QTOF | splash10-014i-0000000009-ca3f7b3580cfc8035037 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 40V, Negative-QTOF | splash10-0a4r-0007120191-89d350907d4d2fe5cbf7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 10V, Negative-QTOF | splash10-001i-0000000090-bd09935a9e14a7e78d8f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 20V, Negative-QTOF | splash10-00lr-0005001090-79db4730e166c2c0d5bd | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(O-22:1(13Z)/22:2(13Z,16Z)) 40V, Negative-QTOF | splash10-002r-4009400000-55c8e25f625487b4c186 | 2021-09-25 | Wishart Lab | View Spectrum |
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Disease References | Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Obesity |
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- Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
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