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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-12 01:33:03 UTC |
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Update Date | 2019-01-11 19:22:29 UTC |
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HMDB ID | HMDB0008201 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PC(18:3(9Z,12Z,15Z)/18:0) |
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Description | PC(18:3(9Z,12Z,15Z)/18:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:3(9Z,12Z,15Z)/18:0), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of stearic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the stearic acid moiety is derived from animal fats, coco butter and sesame oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. |
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Structure | |
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Synonyms | Value | Source |
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PC(18:3(9Z,12Z,15Z)/18:0) | Lipid Annotator | 1-a-linolenoyl-2-stearoyl-sn-glycero-3-phosphocholine | Lipid Annotator | GPCho(36:3) | Lipid Annotator | PC(36:3) | Lipid Annotator | Phosphatidylcholine(18:3/18:0) | Lipid Annotator | PC(18:3/18:0) | Lipid Annotator | Phosphatidylcholine(36:3) | Lipid Annotator | Lecithin | Lipid Annotator | 1-(9Z,12Z,15Z-octadeatrienoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine | Lipid Annotator | GPCho(18:3/18:0) | Lipid Annotator |
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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)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-(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)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)C |
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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/h8,10,14,16,20,22,42H,6-7,9,11-13,15,17-19,21,23-41H2,1-5H3/b10-8-,16-14-,22-20-/t42-/m1/s1 |
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InChI Key | QAVRIJZWHPNXBW-BHLPDSGJSA-N |
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Chemical Taxonomy |
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Classification | Not classified |
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Ontology |
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Physiological effect | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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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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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 165.5(44.39) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 63.7 (53.6-73.5) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected and Quantified | 129.9 +/- 26.4 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 106 (89.5-120) uM | Infant (0-1 year old) | Not Available | Normal | | details | Feces | Detected and Quantified | 1.67 +/- 5.26 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 1.07 +/- 1.25 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.082 +/- 0.033 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0024 (0.0005-0.024) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 108.5 +/- 32.8 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 132.1 +/- 39.6 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 138.91(39.01) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Blood | Detected and Quantified | 106.650 (95.964) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 188.801 (66.714) uM | Adult (>18 years old) | Female | Pregnancy | | details | Feces | Detected but not Quantified | | Newborn (0-30 days old) | Not Specified | Premature neonates | | details |
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Predicted Concentrations |
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Blood | 1.016 +/- 0.373 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 12.500 +/- 4.814 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | Calculated using MetaboAnalyst |
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Associated Disorders and Diseases |
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Disease References | Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Obesity |
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- Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
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Associated OMIM IDs | |
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External Links |
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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 | 52922843 |
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PDB ID | Not Available |
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ChEBI ID | 89438 |
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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 | Not Available |
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