Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-12 01:27:50 UTC |
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Update Date | 2022-03-07 02:49:57 UTC |
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HMDB ID | HMDB0007891 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) |
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Description | PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 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(14:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of myristic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the docosapentaenoic acid moiety is derived from fish oils. 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 | CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-17-15-13-11-9-7-2/h8,10,14,16,19-20,22-23,25,27,42H,6-7,9,11-13,15,17-18,21,24,26,28-41H2,1-5H3/b10-8-,16-14-,20-19-,23-22-,27-25-/t42-/m1/s1 |
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Synonyms | Value | Source |
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GPCho(36:5) | HMDB | PC(14:0/22:5) | HMDB | Phosphatidylcholine(36:5) | HMDB | 1-Myristoyl-2-docosapentaenoyl-sn-glycero-3-phosphocholine | HMDB | Lecithin | HMDB | Phosphatidylcholine(14:0/22:5) | HMDB | PC(36:5) | HMDB | 1-Tetradecanoyl-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphocholine | HMDB | GPCho(14:0/22:5) | HMDB | PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) | Lipid Annotator |
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Chemical Formula | C44H78NO8P |
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Average Molecular Weight | 780.0658 |
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Monoisotopic Molecular Weight | 779.546504989 |
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IUPAC Name | (2-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional Name | lecithin |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-22-23-24-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-17-15-13-11-9-7-2/h8,10,14,16,19-20,22-23,25,27,42H,6-7,9,11-13,15,17-18,21,24,26,28-41H2,1-5H3/b10-8-,16-14-,20-19-,23-22-,27-25-/t42-/m1/s1 |
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InChI Key | SFEMWZZGMMRGCX-DYPKKMQZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. |
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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 | Phosphatidylcholines |
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Alternative Parents | |
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Substituents | - Diacylglycero-3-phosphocholine
- Phosphocholine
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Quaternary ammonium salt
- Tetraalkylammonium salt
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Amine
- Organic salt
- Hydrocarbon derivative
- 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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Not Available | Not Available |
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) | CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5504.9 | Standard polar | 33892256 | PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) | CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 4500.5 | Standard non polar | 33892256 | PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) | CCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5078.9 | Semi standard non polar | 33892256 |
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Spectra |
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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(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-03ei-9154331300-fe605cf40fb850b6d995 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-03di-5594120100-2f7e5385ef75b4615f03 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0019-8292010100-383c0eac4377a6827439 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-004i-0093000300-6bf32e98a7c91ea9768d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-004i-0192001000-85d51b96d6c99e5af921 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-8297000000-885ee44241ad5d9fbc22 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-000i-0000000900-82395bc23558c5e73383 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-000i-0000000900-d73ebce581a3424e67e3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0zi1-0202649400-7477ed35d87f5516786a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-001i-0000000900-11abb7219d74a5a60a04 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-001i-0600000900-8b887b2cddb30aa5f84a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0ff0-1900230300-06c6720b1d231f99f823 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-004i-0000000900-6ac0ce44c5d362b404ab | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-004i-0034030900-4b305705c88ee66bc52c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-4392000000-bcc7cf735079651ade12 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-03di-0000000090-d1fecbe733b4fab2e6fb | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-03di-0011000090-63cbf52d035bcf4b7043 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-01t9-0099000090-e7a83072a8b00fcc7e8c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0udi-0000000090-be732a4aa7f691f68131 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0udi-0000000190-37d5d9b145362a874a18 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-014j-0900449110-a86a54619f09a4ddbc6e | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 8.39 (6.57-11.5) uM | Infant (0-1 year old) | Not Available | Normal | | details | Blood | Detected and Quantified | 5.2 (4.18-6.71) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected and Quantified | 29.3 +/- 15.5 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 46.61(21.41) uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.06 +/- 0.07 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.26 +/- 0.5 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.011 +/- 0.001 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 20.626 (20.914) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 42.042 (23.098) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 13.5 +/- 6.1 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 17.9 +/- 7.9 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 34.81(10.82) uM | Adult (>18 years old) | Both | Heart failure with reduced ejection fraction | | details |
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Predicted Concentrations |
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Blood | 0.107 +/- 0.010 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 16.900 +/- 3.727 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | Calculated using MetaboAnalyst |
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Associated Disorders and Diseases |
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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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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 53478613 |
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PDB ID | Not Available |
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ChEBI ID | 89584 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000503 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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