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| Identification |
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| YMDB ID | YMDB01185 |
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| Name | PC(16:1(9Z)/16:1(9Z)) |
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| Species | Saccharomyces cerevisiae |
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| Strain | Brewer's yeast |
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| Description | PC(16:1(9Z)/16:1(9Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate. |
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| Structure | |
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| Synonyms | - 1,2-Diacyl-sn-glycero-3-phosphocholine
- 1,2-dipalmitoleoyl-rac-glycero-3-phosphocholine
- 3-O-sn-Phosphatidyl-L-serine
- 3-sn-Phosphatidylcholine
- Choline phosphatide
- GPCho(16:1/16:1)
- GPCho(16:1n7/16:1n7)
- GPCho(16:1w7/16:1w7)
- GPCho(32:2)
- Lecithin
- Lecithins
- O3-Phosphatidyl-L-serine
- PC(16:1/16:1)
- PC(16:1n7/16:1n7)
- PC(16:1w7/16:1w7)
- PC(32:2)
- Phosphatidyl-L-serine
- phosphatidyl-L-serines
- Phosphatidyl-N-trimethylethanolamine
- Phosphatidylcholine
- Phosphatidylcholine(16:1/16:1)
- Phosphatidylcholine(16:1n7/16:1n7)
- Phosphatidylcholine(16:1w7/16:1w7)
- Phosphatidylcholine(32:2)
- 1,2-Di-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine
- 1,2-Dipalmitoleoyl-sn-glycero-3-phosphorylcholine
- Dipalmitoleoyl-L-alpha-glycerophosphorylcholine
- L-Dipalmitoleoyllecithin
- PC 16:1(9Z)/16:1(9Z)
- Dipalmitoleoyl-L-a-glycerophosphorylcholine
- Dipalmitoleoyl-L-α-glycerophosphorylcholine
- PC Aa C32:2
- PC(16:1(9Z)/16:1(9Z))
- 1,2-di(9Z-hexadecenoyl)-rac-glycero-3-phosphocholine
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| CAS number | 8002-43-5 |
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| Weight | Average: 730.0071
Monoisotopic: 729.530854925 |
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| InChI Key | GPWHCUUIQMGELX-VHQDNGOZSA-N |
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| InChI | InChI=1S/C40H76NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h16-19,38H,6-15,20-37H2,1-5H3/b18-16-,19-17-/t38-/m1/s1 |
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| IUPAC Name | (2-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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| Traditional IUPAC Name | L-dipalmitoleoyllecithin |
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| Chemical Formula | C40H76NO8P |
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| SMILES | CCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC |
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| Chemical Taxonomy |
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| Description | This compound 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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| 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 | | Glycerophospholipid metabolism | PW002493 |    | | Lysolipid incorporation into ER PC(16:1(9Z)/16:1(9Z)) | PW002785 |    | | Lysolipid incorporation into Mitochondria PC(16:1(9Z)/16:1(9Z)) | PW002793 |    | | Phosphatidylcholine biosynthesis PC(16:1(9Z)/16:1(9Z)) | PW002868 |    |
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| KEGG Pathways | | Arachidonic acid metabolism | ec00590 |  | | Glycerophospholipid metabolism | ec00564 |  | | Linoleic acid metabolism | ec00591 |  | | alpha-Linolenic acid metabolism | ec00592 |  |
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| SMPDB Reactions | |
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| KEGG Reactions | Not Available |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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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: | - Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
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| Synthesis Reference: | Not Available |
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| External Links: | |
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