| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2008-09-12 01:30:02 UTC |
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| Update Date | 2018-05-20 10:15:50 UTC |
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| HMDB ID | HMDB0008022 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) |
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| Description | PC(16:1(9Z)/22:5(4Z,7Z,10Z,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(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the docosapentaenoic acid moiety is derived from animal fats and brain. 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 | |
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| Synonyms | | Value | Source |
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| GPCho(38:6) | Lipid Annotator | | PC(16:1/22:5) | Lipid Annotator | | Phosphatidylcholine(16:1/22:5) | Lipid Annotator | | Phosphatidylcholine(38:6) | Lipid Annotator | | Lecithin | Lipid Annotator | | GPCho(16:1/22:5) | Lipid Annotator | | PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) | Lipid Annotator | | 1-palmitoleoyl-2-osbondoyl-sn-glycero-3-phosphocholine | Lipid Annotator | | 1-(9Z-hexadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3-phosphocholine | Lipid Annotator | | PC(38:6) | Lipid Annotator |
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| Chemical Formula | C46H80NO8P |
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| Average Molecular Weight | 806.1031 |
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| Monoisotopic Molecular Weight | 805.562155053 |
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| IUPAC Name | (2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-3-[(9Z)-hexadec-9-enoyloxy]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 | CCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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| InChI Identifier | InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16-17,19-21,23-24,27,29,33,35,44H,6-13,15,18,22,25-26,28,30-32,34,36-43H2,1-5H3/b16-14-,19-17-,21-20-,24-23-,29-27-,35-33-/t44-/m1/s1 |
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| InChI Key | WCODZEYPAWOVBI-UMQSOSPQSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Physiological effect | Organoleptic effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: Biological role: |
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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 | |
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| Spectra |
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| Spectra | |
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| Pathways | |
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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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- Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
- 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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