Identification |
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YMDB ID | YMDB02263 |
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Name | PC(o-16:1(9Z)/18:0) |
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Species | Saccharomyces cerevisiae |
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Strain | Brewer's yeast |
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Description | PC(o-16:1(9Z)/18:0) 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-16:1(9Z)/18:0), in particular, consists of one chain of Palmitoleyl alcohol at the C-1 position and one chain of stearic acid at the C-2 position. The Palmitoleyl alcohol moiety is derived from whale oil, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. 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 | - 1-Palmitoleyl-2-stearoyl-sn-glycero-3-phosphocholine
- GPCho(16:1/18:0)
- GPCho(16:1n7/18:0)
- GPCho(16:1w7/18:0)
- GPCho(34:1)
- Lecithin
- PC(16:1n7/18:0)
- PC(16:1w7/18:0)
- PC(34:1)
- Phosphatidylcholine(16:1/18:0)
- Phosphatidylcholine(16:1n7/18:0)
- Phosphatidylcholine(16:1w7/18:0)
- Phosphatidylcholine(34:1)
- PC(16:1/18:0)
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CAS number | Not Available |
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Weight | Average: 746.0926 Monoisotopic: 745.598540559 |
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InChI Key | SVSLBZPEDBYFGG-UHFFFAOYSA-N |
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InChI | InChI=1S/C42H84NO7P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-42(44)50-41(40-49-51(45,46)48-38-36-43(3,4)5)39-47-37-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h17,19,41H,6-16,18,20-40H2,1-5H3 |
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IUPAC Name | (2-{[3-(hexadec-9-en-1-yloxy)-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional IUPAC Name | (2-{[3-(hexadec-9-en-1-yloxy)-2-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium |
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Chemical Formula | C42H84NO7P |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)OC(COCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C |
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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 | Not Available |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | Not Available |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Not Available |
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KEGG Pathways | Not Available |
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SMPDB Reactions | Not Available |
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KEGG Reactions | Not Available |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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0.038 ± 0.0019 µM | YEB media with 0.5 mM glucose | aerobic | Brewer's yeast | Experimentally Determined Not Available | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | |
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References |
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References: | Not Available |
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Synthesis Reference: | Not Available |
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External Links: | Resource | Link |
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CHEBI ID | Not Available | HMDB ID | HMDB13412 | Pubchem Compound ID | 76043901 | Kegg ID | Not Available | ChemSpider ID | 24822856 | FOODB ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
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