Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 23:49:33 UTC |
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Update Date | 2020-06-04 20:43:57 UTC |
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MCDB ID | BMDB0008040 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(18:0/18:3(6Z,9Z,12Z)) |
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Description | PC(18:0/18:3(6Z,9Z,12Z)), also known as gpcho(18:0/18:3) or gpcho(36:3), 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(18:0/18:3(6Z,9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:3(6Z,9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:3(6Z,9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:3(6Z,9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:3(6Z,9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:3(6Z,9Z,12Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/18:3(6Z,9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:0/18:3(6Z,9Z,12Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/18:3(6Z,9Z,12Z)) and L-serine can be converted into choline and PS(18:0/18:3(6Z,9Z,12Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(18:0/18:3(6Z,9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/18:3(6Z,9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:0/18:3(6Z,9Z,12Z)) pathway. |
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Structure | |
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Synonyms | Value | Source |
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1-Stearoyl-2-g-linolenoyl-sn-glycero-3-phosphocholine | ChEBI | 1-Stearoyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholine | ChEBI | GPCho(18:0/18:3) | ChEBI | GPCho(18:0/18:3n6) | ChEBI | GPCho(18:0/18:3W6) | ChEBI | PC(18:0/18:3) | ChEBI | PC(18:0/18:3n6) | ChEBI | PC(18:0/18:3W6) | ChEBI | Phosphatidylcholine(18:0/18:3) | ChEBI | Phosphatidylcholine(18:0/18:3n6) | ChEBI | Phosphatidylcholine(18:0/18:3W6) | ChEBI | 1-Stearoyl-2-γ-linolenoyl-sn-glycero-3-phosphocholine | Generator | GPCho(36:3) | Lipid Annotator, HMDB | PC(36:3) | Lipid Annotator, HMDB | Lecithin | Lipid Annotator, HMDB | Phosphatidylcholine(36:3) | Lipid Annotator, HMDB | PC(18:0/18:3(6Z,9Z,12Z)) | Lipid Annotator | 1-octadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine | Lipid Annotator, HMDB |
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Chemical Formula | C44H82NO8P |
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Average Molecular Weight | 784.0975 |
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Monoisotopic Molecular Weight | 783.577805117 |
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IUPAC Name | trimethyl(2-{[(2R)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-3-(octadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium |
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Traditional Name | lecithin |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCC(=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/C44H82NO8P/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/h15,17,21,23,27,29,42H,6-14,16,18-20,22,24-26,28,30-41H2,1-5H3/b17-15-,23-21-,29-27-/t42-/m1/s1 |
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InChI Key | KJVJKBRMUDGTKA-NZXQIXPOSA-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 | splash10-00li-9081052400-cbc1cf6b4a37d1de9214 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02u9-4292021100-7ad04a2c895103b74843 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-8095020100-960b863245c4e225be89 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0090000300-1a468679a6149dbc6b3e | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00lr-0090001000-5393c0a85c1250350a89 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00pr-3090100000-426f104bf5b1d72503ec | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0000000900-f44acebd42271f9d37fe | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0000000900-d39b20e156e47b15fe77 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a59-0200498400-f75dff37980d754872c2 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000000090-02472e506be910245a7b | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0030000090-4a8a30d711ba5dbcbc6d | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01ai-0090000040-d4a837443937b0025dde | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0000000900-016fbc06bd6c36a12e4f | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0600000900-7ba4362bb833d26b28b0 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f89-1900041300-914319d13a6e3e697365 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000000900-f313232611c4c0c71d38 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0090020700-793d4965b69e11e425b5 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-4190000000-1f42c3349b3c512805ae | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0000000090-1db30625399fdea6b457 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-0000000190-671ed31d83ec847480a0 | 2021-09-25 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006t-0900369110-2786bfbce693bc75f64f | 2021-09-25 | View Spectrum |
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Concentrations |
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Detected and Quantified | 3.24 +/- 0.04 uM | | | details | Detected and Quantified | 4.0 +/- 0.1 uM | | | details | Detected and Quantified | 5.3 +/- 0.1 uM | | | details |
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External Links |
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HMDB ID | HMDB0008040 |
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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 | 24766705 |
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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 | 52922655 |
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PDB ID | Not Available |
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ChEBI ID | 86117 |
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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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