| Identification |
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| YMDB ID | YMDB02218 |
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| Name | PC(22:1(13Z)/18:1(11Z)) |
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| Species | Saccharomyces cerevisiae |
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| Strain | Brewer's yeast |
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| Description | PC(22:1(13Z)/18:1(11Z)) 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(22:1(13Z)/18:1(11Z)), in particular, consists of one chain of erucic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The erucic acid moiety is derived from seed oils and avocados, while the vaccenic acid moiety is derived from butter fat and animal fat. 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-erucoyl-2-vaccenoyl-sn-glycero-3-phosphocholine
- GPCho(22:1/18:1)
- GPCho(22:1n9/18:1n7)
- GPCho(22:1w9/18:1w7)
- GPCho(40:2)
- Lecithin
- PC(22:1/18:1)
- PC(22:1n9/18:1n7)
- PC(40:2)
- Phosphatidylcholine(22:1/18:1)
- Phosphatidylcholine(22:1n9/18:1n7)
- Phosphatidylcholine(22:1w9/18:1w7)
- Phosphatidylcholine(40:2)
- PC(22:1w9/18:1w7)
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| CAS number | Not Available |
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| Weight | Average: 842.2197
Monoisotopic: 841.656055437 |
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| InChI Key | VMYYPARBVHMEFG-UHFFFAOYSA-N |
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| InChI | InChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-26-21-19-17-15-13-11-9-7-2/h17,19-20,22,46H,6-16,18,21,23-45H2,1-5H3 |
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| IUPAC Name | (2-{[3-(docos-13-enoyloxy)-2-(octadec-11-enoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium |
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| Traditional IUPAC Name | (2-{[3-(docos-13-enoyloxy)-2-(octadec-11-enoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium |
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| Chemical Formula | C48H92NO8P |
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| SMILES | CCCCCCCCC=CCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCC=CCCCCCC |
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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
- Dialkyl phosphate
- Fatty acid ester
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Dicarboxylic acid or derivatives
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Amine
- 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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| 0.043 ± 0.00215 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 | Not Available |
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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 | HMDB11202 | | Pubchem Compound ID | 76043076 | | Kegg ID | Not Available | | ChemSpider ID | 24767224 | | FOODB ID | Not Available | | Wikipedia ID | Not Available | | BioCyc ID | Not Available |
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