Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 23:49:01 UTC |
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Update Date | 2020-06-04 19:46:14 UTC |
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MCDB ID | BMDB0008014 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(16:1(9Z)/20:3(8Z,11Z,14Z)) |
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Description | PC(16:1(9Z)/20:3(8Z,11Z,14Z)), also known as phosphatidylcholine(16:1/20:3) or lecithin, 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(16:1(9Z)/20:3(8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/20:3(8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/20:3(8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/20:3(8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/20:3(8Z,11Z,14Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/20:3(8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/20:3(8Z,11Z,14Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/20:3(8Z,11Z,14Z)) and L-serine can be converted into choline and PS(16:1(9Z)/20:3(8Z,11Z,14Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/20:3(8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:3(8Z,11Z,14Z)) pathway. |
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Structure | |
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Synonyms | Value | Source |
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Phosphatidylcholine(16:1/20:3) | HMDB | Phosphatidylcholine(36:4) | HMDB | Lecithin | HMDB | PC(36:4) | HMDB | GPCho(16:1/20:3) | HMDB | 1-Palmitoleoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphocholine | HMDB | PC(16:1/20:3) | HMDB | 1-(9Z-Hexadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholine | HMDB | GPCho(36:4) | HMDB | PC(16:1(9Z)/20:3(8Z,11Z,14Z)) | Lipid Annotator |
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Chemical Formula | C44H80NO8P |
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Average Molecular Weight | 782.0817 |
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Monoisotopic Molecular Weight | 781.562155053 |
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IUPAC Name | (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-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 | CCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h14,16-17,19-21,23,25,42H,6-13,15,18,22,24,26-41H2,1-5H3/b16-14-,19-17-,21-20-,25-23-/t42-/m1/s1 |
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InChI Key | SCFKGVINVZBYAF-MLQXCARSSA-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 GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-8191231300-b85c4a4342e09b2f631d | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-3291010000-12c3e7663f36e0b9b862 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-6192010100-2764455ea3a899ffe8cd | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ka9-0092000300-4af663749befe55111b6 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udr-0090001000-2547cb48df31406c3dd0 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pbi-4092000000-40c5a9f219b93187973c | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000000900-bc2a7ab6e102186d0c94 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0000000900-1f8c8c5ddd6d8082b38d | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pe9-0200669400-781deed501d289b640d2 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000000900-440a71e9c384cc6f77dd | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0600000900-9035a7e163ecdf01e45f | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-1900230300-b2188caf400b69e3dd96 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000000900-2534b1e8e0eb889fbec2 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001r-0053030900-8ba777eefc865845a1af | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0zfr-5492100000-05990d6899eeed0a99f3 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000000090-3c72155bce4155773a03 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0000000190-064c081755895a2e4178 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006t-0900449110-eec7281881c99dba6fbd | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000000090-08d6fcb41388b1c681f8 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0011000090-f723a38c0d491a12b21f | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-15mi-0099000090-7534dc92231fbbc26652 | 2021-09-25 | View Spectrum |
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Concentrations |
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Detected and Quantified | 1.20 +/- 0.02 uM | | | details | Detected and Quantified | 1.63 +/- 0.04 uM | | | details | Detected and Quantified | 1.86 +/- 0.03 uM | | | details | Detected and Quantified | 1.06 +/- 0.01 uM | | | details |
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External Links |
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HMDB ID | HMDB0008014 |
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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 | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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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 | 52922463 |
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PDB ID | Not Available |
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ChEBI ID | 89740 |
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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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