Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:15:25 UTC |
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NP-MRD ID | NP0000429 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | PC(16:0/16:0) |
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Description | PC(16:0/16:0) 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(16:0/16:0), In particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. 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 | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C40H80NO8P/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/h38H,6-37H2,1-5H3/t38-/m1/s1 |
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Synonyms | Value | Source |
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1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine | ChEBI | 1,2-Dipalmitoyl-L-lecithin | ChEBI | 1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine | ChEBI | 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine | ChEBI | 1,2-Dipalmitoylphosphatidylcholine | ChEBI | 1-16:0-2-16:0-Phosphatidylcholine | ChEBI | 16:0-16:0-PC | ChEBI | Colfosceril palmitate | ChEBI | Colfoscerili palmitas | ChEBI | Dipalmitoyl phosphatidylcholine | ChEBI | Dipalmitoyl-GPC | ChEBI | Dipalmitoylphosphatidylcholine | ChEBI | GPC(16:0/16:0) | ChEBI | GPCho 16:0/16:0 | ChEBI | GPCho(16:0/16:0) | ChEBI | Palmitate de colfosceril | ChEBI | Palmitato de colfoscerilo | ChEBI | PC 16:0/16:0 | ChEBI | PC(32:0) | ChEBI | Phosphatidylcholine 16:0/16:0 | ChEBI | Phosphatidylcholine(16:0/16:0) | ChEBI | Phosphatidylcholine(32:0) | ChEBI | Colfosceril palmitic acid | Generator | Palmitic acid de colfosceril | Generator | 1,2-Dipalmitoyl-rac-glycero-3-phosphocholine | HMDB | Lecithin | HMDB | 1,2-Dihexadecanoyl-rac-glycero-3-phosphocholine | HMDB | GPCho(32:0) | HMDB | (R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt | HMDB | (R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt | HMDB | 1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine | HMDB | 1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine | HMDB | 1,2-Dipalmitoyl-3-sn-phosphatidylcholine | HMDB | 1,2-Dipalmitoyl-L-3-phosphatidylcholine | HMDB | 1,2-Dipalmitoyl-L-a-lecithin | HMDB | 1,2-Dipalmitoyl-L-a-phosphatidylcholine | HMDB | 1,2-Dipalmitoyl-L-alpha-lecithin | HMDB | 1,2-Dipalmitoyl-L-alpha-phosphatidylcholine | HMDB | 1,2-Dipalmitoyl-L-phosphatidylcholine | HMDB | 1,2-Dipalmitoyl-sn-3-glycerophosphocholine | HMDB | 1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine | HMDB | 1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine | HMDB | 1,2-Dipalmitoyl-sn-glycerophosphocholine | HMDB | 1,2-Dipalmitoyl-sn-glycerophosphorylcholine | HMDB | 1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine | HMDB | 1,2-Dipalmitoyl-sn-phosphatidylcholine | HMDB | 1,2-Dipalmitoylglycero-3-phosphocholine | HMDB | 1,2-L-a-Dipalmitoylphosphatidylcholine | HMDB | 1,2-L-alpha-Dipalmitoylphosphatidylcholine | HMDB | b,g-Dipalmitoyl L-a-phosphatidylcholine | HMDB | b,g-Dipalmitoyl L-alpha-phosphatidylcholine | HMDB | b,g-Dipalmitoyl-L-(a)-lecithin | HMDB | b,g-Dipalmitoyl-L-phosphatidylcholine | HMDB | Dihexadecanoyl-sn-glycero-3-phosphocholine | HMDB | Dipalmitoyl L-a-phosphatidylcholine | HMDB | Dipalmitoyl L-alpha-phosphatidylcholine | HMDB | Dipalmitoyl-L-3-glycerylphosphorylcholine | HMDB | Dipalmitoyl-L-a-lecithin | HMDB | Dipalmitoyl-L-a-phosphatidylcholine | HMDB | Dipalmitoyl-L-alpha-lecithin | HMDB | Dipalmitoyl-L-alpha-phosphatidylcholine | HMDB | Dipalmitoyl-sn-3-phosphatidylcholine | HMDB | DPPC | HMDB | L-1,2-Dipalmitoyl-a-lecithin | HMDB | L-1,2-Dipalmitoyl-alpha-lecithin | HMDB | L-1,2-Dipalmitoylphosphatidylcholine | HMDB | L-a-1,2-Dipalmitoyl lecithin | HMDB | L-a-Dipalmitoylecithin | HMDB | L-a-Dipalmitoyllecithin | HMDB | L-a-Dipalmitoylphosphatidylcholine | HMDB | L-a-DPPC | HMDB | L-alpha-1,2-Dipalmitoyl lecithin | HMDB | L-alpha-Dipalmitoylecithin | HMDB | L-alpha-Dipalmitoyllecithin | HMDB | L-alpha-Dipalmitoylphosphatidylcholine | HMDB | L-alpha-DPPC | HMDB | L-b,g-Dipalmitoyl-a-lecithin | HMDB | L-b,g-Dipalmitoyl-a-phosphatidylcholine | HMDB | L-b,g-Dipalmitoyl-alpha-lecithin | HMDB | L-b,g-Dipalmitoyl-alpha-phosphatidylcholine | HMDB | L-b,g-Dipalmitoylphosphatidylcholine | HMDB | L-Dipalmitoyl lecithin | HMDB | L-DPPC | HMDB | PC Aa C32:0 | HMDB | sn-3-Dipalmitoyllecithin | HMDB | 1,2-Dipalmitoyl-GPC | HMDB | PC(16:0/16:0) | Lipid Annotator |
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Chemical Formula | C40H80NO8P |
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Average Mass | 734.0389 Da |
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Monoisotopic Mass | 733.56216 Da |
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IUPAC Name | (2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium |
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CAS Registry Number | 63-89-8 |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C40H80NO8P/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/h38H,6-37H2,1-5H3/t38-/m1/s1 |
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InChI Key | KILNVBDSWZSGLL-KXQOOQHDSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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
- 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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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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