Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 16:52:03 UTC |
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Updated at | 2022-09-12 16:52:03 UTC |
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NP-MRD ID | NP0330983 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2-{[(2r)-3-(hexadecanoyloxy)-2-[(6z,9z,12z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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Description | PC(16:0/18:3(6Z,9Z,12Z)), also known as PC(16:0/18:3) Or PC(34:3), 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. Thus, PC(16:0/18:3(6Z,9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/18:3(6Z,9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:3(6Z,9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. Within humans, PC(16:0/18:3(6Z,9Z,12Z)) participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(16:0/18:3(6Z,9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:3(6Z,9Z,12Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(16:0/18:3(6Z,9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:0/18:3(6Z,9Z,12Z)/0:0) Through its interaction with the enzyme choline/ethanolaminephosphotransferase. A phosphatidylcholine 34:3 In which the acyl groups specified at positions 1 and 2 are palmitoyl and (6Z,9Z,12Z)-octadecatrienoyl (gamma-linolenoyl) respectively. (2-{[(2r)-3-(hexadecanoyloxy)-2-[(6z,9z,12z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium is found in Trypanosoma brucei. It was first documented in 2020 (PMID: 32033212). In humans, PC(16:0/18:3(6Z,9Z,12Z)) is involved in phosphatidylcholine biosynthesis. |
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Structure | CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,25,27,40H,6-13,15,17-19,22-24,26,28-39H2,1-5H3/b16-14-,21-20-,27-25-/t40-/m1/s1 |
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Synonyms | Value | Source |
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1-Hexadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine | ChEBI | 1-Palmitoyl-2-(gamma-linolenoyl)-sn-glycero-3-phosphocholine | ChEBI | PC(16:0/18:3) | ChEBI | 1-Palmitoyl-2-(g-linolenoyl)-sn-glycero-3-phosphocholine | Generator | 1-Palmitoyl-2-(γ-linolenoyl)-sn-glycero-3-phosphocholine | Generator | PC(34:3) | HMDB | Lecithin | HMDB | GPCho(16:0/18:3) | HMDB | Phosphatidylcholine(34:3) | HMDB | GPCho(34:3) | HMDB | Phosphatidylcholine(16:0/18:3) | HMDB | 1-Palmitoyl-2-g-linolenoyl-sn-glycero-3-phosphocholine | HMDB | 1-Palmitoyl-2-gamma-linolenoyl-GPC | HMDB | 1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholine | HMDB | 1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-phosphatidylcholine | HMDB | 1-Palmitoyl-2-linolenoyl-GPC | HMDB | GPC(16:0/18:3(6Z,9Z,12Z)) | HMDB | GPC(16:0/18:3) | HMDB | GPC(16:0/18:3n6) | HMDB | GPC(16:0/18:3W6) | HMDB | GPC(34:3) | HMDB | GPCho(16:0/18:3(6Z,9Z,12Z)) | HMDB | GPCho(16:0/18:3n6) | HMDB | GPCho(16:0/18:3W6) | HMDB | PC(16:0/18:3n6) | HMDB | PC(16:0/18:3W6) | HMDB | Phosphatidylcholine(16:0/18:3(6Z,9Z,12Z)) | HMDB | Phosphatidylcholine(16:0/18:3n6) | HMDB | Phosphatidylcholine(16:0/18:3W6) | HMDB | PC(16:0/18:3(6Z,9Z,12Z)) | Lipid Annotator |
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Chemical Formula | C42H78NO8P |
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Average Mass | 756.0444 Da |
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Monoisotopic Mass | 755.54650 Da |
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IUPAC Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional Name | lecithin |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,25,27,40H,6-13,15,17-19,22-24,26,28-39H2,1-5H3/b16-14-,21-20-,27-25-/t40-/m1/s1 |
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InChI Key | CNNSEHUKQJCGTE-UPPWDXJYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 | Not Available |
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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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