Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 19:23:30 UTC |
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Updated at | 2022-06-29 19:23:30 UTC |
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NP-MRD ID | NP0138925 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Soybean phospholipid |
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Description | PC(16:0/18:2(9Z,12Z)), also known as GPC(16:0/18:2) Or PC(34:2), 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(16:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. A phosphatidylcholine 34:2 In which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl) and 9Z,12Z-octadecadienoyl (linoleoyl) respectively. PC(16:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. Within humans, PC(16:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:0/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(16:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(16:0/18:2(9Z,12Z)/0:0) Through the action of the enzyme choline/ethanolaminephosphotransferase. In humans, PC(16:0/18:2(9Z,12Z)) is involved in phosphatidylcholine biosynthesis. Outside of the human body, PC(16:0/18:2(9Z,12Z)) is found, on average, in the highest concentration within milk (cow). PC(16:0/18:2(9Z,12Z)) has also been detected, but not quantified in, several different foods, such as european chestnuts, peppers, cumins, hickory nuts, and malus (crab apple). Soybean phospholipid is found in Lycoris radiata. It was first documented in 2002 (PMID: 11779181). This could make PC(16:0/18:2(9Z,12Z)) a potential biomarker for the consumption of these foods (PMID: 32033212). |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C42H80NO8P/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/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1 |
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Synonyms | Value | Source |
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1-Palmitoyl-2-linoleoyl-GPC | ChEBI | 1-Palmitoyl-2-linoleoyl-GPC (16:0/18:2) | ChEBI | 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine | ChEBI | 1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholine | ChEBI | 1-Palmitoyl-2-linoleoyl-sn-glycerophosphatidylcholine | ChEBI | 1-Palmitoyl-2-linoleoylphosphatidylcholine | ChEBI | GPC(16:0/18:2) | ChEBI | GPCho 16:0/18:2(9Z,12Z) | ChEBI | GPCho(16:0/18:2(9Z,12Z)) | ChEBI | GPCho(16:0/18:2) | ChEBI | GPCho(16:0/18:2omega6) | ChEBI | Lecithin | ChEBI | PC 16:0/18:2(9Z,12Z) | ChEBI | PC(16:0/18:2) | ChEBI | PC(16:0/18:2omega6) | ChEBI | PC(34:2) | ChEBI | Phosphatidylcholine 16:0/18:2(9Z,12Z) | ChEBI | Phosphatidylcholine(16:0/18:2(9Z,12Z)) | ChEBI | Phosphatidylcholine(16:0/18:2) | ChEBI | Phosphatidylcholine(16:0/18:2omega6) | ChEBI | Gpcho(34:2) | HMDB | Phosphatidylcholine(34:2) | HMDB | 2-Linoleoyl-1-palmitoyl-sn-phosphatidylcholine | HMDB | Palmitoyl-linoleoatephosphatidylcholine | HMDB | PLPC | HMDB | 1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine | HMDB | 1-Palmitoyl-2-linoleoyl-3-phosphatidylcholine | HMDB | 1-Palmitoyl-2-linoleoyl-3-sn-glycerophosphatidylcholine | HMDB | 1-Palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine | HMDB | 1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine | HMDB | 1-Palmitoyl-2-linoleoyllecithin | HMDB | GPC(16:0/18:2(9Z,12Z)) | HMDB | GPC(16:0/18:2n6) | HMDB | GPC(16:0/18:2W6) | HMDB | GPC(34:2) | HMDB | GPCho(16:0/18:2n6) | HMDB | GPCho(16:0/18:2W6) | HMDB | L-alpha-1-Palmitoyl-2-linoleoylphosphatidylcholine | HMDB | L-Α-1-palmitoyl-2-linoleoylphosphatidylcholine | HMDB | PC(16:0/18:2n6) | HMDB | PC(16:0/18:2W6) | HMDB | Phosphatidylcholine(16:0/18:2n6) | HMDB | Phosphatidylcholine(16:0/18:2W6) | HMDB | PC(16:0/18:2(9Z,12Z)) | Lipid Annotator, ChEBI |
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Chemical Formula | C42H80NO8P |
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Average Mass | 758.0603 Da |
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Monoisotopic Mass | 757.56216 Da |
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IUPAC Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium |
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CAS Registry Number | 8002-43-5 |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C42H80NO8P/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/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1 |
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InChI Key | JLPULHDHAOZNQI-ZTIMHPMXSA-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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