Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 23:49:31 UTC |
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Update Date | 2020-06-04 20:44:42 UTC |
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MCDB ID | BMDB0008039 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(18:0/18:2(9Z,12Z)) |
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Description | PC(18:0/18:2(9Z,12Z)), also known as PC(18:0/18:2) or 18:0-18:2-PC, 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(18:0/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:2(9Z,12Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:0/18:2(9Z,12Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(18:0/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:0/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:0/18:2(9Z,12Z)) pathway. |
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Structure | |
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Synonyms | Value | Source |
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1-18:0-2-18:2-Phosphatidylcholine | ChEBI | 1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine | ChEBI | 1-Stearoyl-2-linoleoyl-GPC | ChEBI | 1-Stearoyl-2-linoleoyl-GPC (18:0/18:2) | ChEBI | 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine | ChEBI | 18:0-18:2-PC | ChEBI | GPC(18:0/18:2) | ChEBI | GPCho(18:0/18:2) | ChEBI | GPCho(18:0/18:2n6) | ChEBI | GPCho(18:0/18:2W6) | ChEBI | GPCho(36:2) | ChEBI | PC(18:0/18:2) | ChEBI | PC(18:0/18:2n6) | ChEBI | PC(18:0/18:2W6) | ChEBI | PC(36:2) | ChEBI | Phosphatidylcholine (1-18:0-2-18:2) | ChEBI | Phosphatidylcholine(18:0/18:2) | ChEBI | Phosphatidylcholine(18:0/18:2n6) | ChEBI | Phosphatidylcholine(36:2) | ChEBI | SLPC | MeSH | SLPTC | MeSH | 1-Stearoyl-(2-linoleoyl)-sn-glycero-3-phosphocholine | MeSH | 1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine | Lipid Annotator, HMDB | Lecithin | Lipid Annotator, HMDB | PC(18:0/18:2(9Z,12Z)) | Lipid Annotator | 1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine | Lipid Annotator, HMDB | 1-Stearoyl-2-linoleoylphosphatidylcholine | MeSH, HMDB | 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphorylcholine | HMDB | 1-Stearoyl-2-linoleoyl-sn-glycero-phosphatidylcholine | HMDB | 1-Stearoyl-2-linoleoyllecithin | HMDB | 1-Stearyl-2-linoleoyl-3-sn-glycerophosphatidylcholine | HMDB | GPC(18:0/18:2(9Z,12Z)) | HMDB | GPC(18:0/18:2n6) | HMDB | GPC(18:0/18:2w6) | HMDB | GPC(36:2) | HMDB | GPCho(18:0/18:2(9Z,12Z)) | HMDB | Phosphatidylcholine(18:0/18:2(9Z,12Z)) | HMDB | Phosphatidylcholine(18:0/18:2w6) | HMDB |
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Chemical Formula | C44H84NO8P |
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Average Molecular Weight | 786.1134 |
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Monoisotopic Molecular Weight | 785.593455181 |
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IUPAC Name | trimethyl(2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium |
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Traditional Name | lecithin |
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CAS Registry Number | 27098-24-4 |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(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/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,42H,6-14,16,18-20,22,24-41H2,1-5H3/b17-15-,23-21-/t42-/m1/s1 |
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InChI Key | FORFDCPQKJHEBF-VPUSDGANSA-N |
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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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Spectra |
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| Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000000900-36f689a3cf8b031c9ce5 | 2017-10-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0019-0600000900-4df68b8e85813f4b5ad8 | 2017-10-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f89-1900041300-c296264e85d13fe25ffe | 2017-10-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0000000900-64c382f846ba04194d31 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0000000900-6c06686879d9f7790e62 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a59-0200498400-bfcef54bcce75991df2a | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0000000090-53a8e01f33b2af13f226 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0000000190-64f46bdfe255d6a5b5e4 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002b-0900369110-8282d7071a7afc84c25d | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000000900-23df8d3c4971511f3b91 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090020800-f45908c59a59b3451739 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-2090100000-2201cb02c8a98610c1b9 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000000900-e54f4b7d729e27672b37 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0019-0600000900-3a2440aaca7e87ec13a5 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ff0-1900041300-d3ccf7461dac2d683004 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000000090-683d2aaf9f12a9d08614 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0030000090-ceb91fadb205f9c1b737 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ji-0090000040-f6fcdf71c4ae55cc490b | 2021-09-25 | View Spectrum |
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Concentrations |
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Detected and Quantified | 5.82 +/- 0.04 uM | | | details | Detected and Quantified | 7.0 +/- 0.2 uM | | | details | Detected and Quantified | 9.5 +/- 0.1 uM | | | details | Detected and Quantified | 5.48 +/- 0.03 uM | | | details |
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External Links |
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HMDB ID | HMDB0008039 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4945645 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-8279 |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 6441487 |
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PDB ID | Not Available |
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ChEBI ID | 84822 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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