Record Information |
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Version | 5.0 |
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Status | Predicted |
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Creation Date | 2021-09-14 06:37:34 UTC |
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Update Date | 2022-11-30 20:05:12 UTC |
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HMDB ID | HMDB0285913 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) |
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Description | PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)), in particular, consists of one chain of one hexadecanoyl at the C-1 position and one chain of 12-Hydroxyeicosatetraenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396 ). |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCCC InChI=1S/C44H80NO9P/c1-6-8-10-12-14-15-16-17-18-19-23-27-31-35-43(47)51-39-42(40-53-55(49,50)52-38-37-45(3,4)5)54-44(48)36-32-28-24-21-20-22-26-30-34-41(46)33-29-25-13-11-9-7-2/h21-22,24-26,29-30,34,41-42,46H,6-20,23,27-28,31-33,35-40H2,1-5H3/b24-21-,26-22-,29-25-,34-30+/t41-,42+/m0/s1 |
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Synonyms | Value | Source |
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1-Hexadecanoyl-2-(12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine | ChEBI | 1-Palmitoyl-2-[(5Z,8Z,10E,12S,14Z)-12-hydroxyicosatetraenoyl]-sn-glycero-3-phosphocholine | ChEBI | 16:0/12-hete PC | ChEBI | PC(16:0/20:4(5Z,8Z,10E,14Z)(12oh[S])) | ChEBI |
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Chemical Formula | C44H80NO9P |
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Average Molecular Weight | 798.096 |
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Monoisotopic Molecular Weight | 797.557070158 |
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IUPAC Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-{[(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-{[(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C=C/[C@@H](O)C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C44H80NO9P/c1-6-8-10-12-14-15-16-17-18-19-23-27-31-35-43(47)51-39-42(40-53-55(49,50)52-38-37-45(3,4)5)54-44(48)36-32-28-24-21-20-22-26-30-34-41(46)33-29-25-13-11-9-7-2/h21-22,24-26,29-30,34,41-42,46H,6-20,23,27-28,31-33,35-40H2,1-5H3/b24-21-,26-22-,29-25-,34-30+/t41-,42+/m0/s1 |
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InChI Key | YQWFSBLEXGUMGO-GZXBEVTESA-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
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxide
- Organic oxygen compound
- Amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Organopnictogen compound
- Organic zwitterion
- Organic salt
- Carbonyl group
- 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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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Not Available |
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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 IndicesNot Available |
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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(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 10V, Negative-QTOF | splash10-001i-0000000090-b06d17f3021777013fad | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 20V, Negative-QTOF | splash10-001i-0011000090-16ca5903295115bf9920 | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 40V, Negative-QTOF | splash10-0bai-0099000090-5a299381dac786c6beef | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 10V, Positive-QTOF | splash10-0udi-0000000090-0b40c03a690e554b7052 | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 20V, Positive-QTOF | splash10-0udi-0000000190-487aafe9e884ea032c8e | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 40V, Positive-QTOF | splash10-0fl1-0200669220-7a51c55234063d54e647 | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 10V, Positive-QTOF | splash10-00di-0000000090-c01014df694b0f30ca78 | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 20V, Positive-QTOF | splash10-00di-0000000190-ec064be368a0baeaf474 | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 40V, Positive-QTOF | splash10-000k-0900179110-e4aefc7c888c39c31c39 | 2021-10-19 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 10V, Positive-QTOF | splash10-0002-0000000900-bbf1c79505370475e837 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 20V, Positive-QTOF | splash10-000t-0600000900-50e402b3750604f0efb6 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(16:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 40V, Positive-QTOF | splash10-001i-1900221300-c351515996ad6eeb5f9f | 2021-10-21 | Wishart Lab | View Spectrum |
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