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Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-03-07 02:49:04 UTC |
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HMDB ID | HMDB0000593 |
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Secondary Accession Numbers | - HMDB0008104
- HMDB00593
- HMDB0062690
- HMDB08104
- HMDB62690
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Metabolite Identification |
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Common Name | PC(18:1(9Z)/18:1(9Z)) |
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Description | PC(18:1(9Z)/18:1(9Z)) 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(18:1(9Z)/18:1(9Z)), in particular, consists of two chains of oleic acid at the C-1 and C-2 positions. The oleic acid moieties are derived from vegetable oils, especially olive and canola 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. Dioleoylphosphatidylcholine is found in human platelets and red blood cells, in mitochondria from skeletal muscle, lung, umbilical artery and vein endothelial cells (PMID: 15351277 , 7138900 , 2351875 , 4046747 , 2755318 ).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 | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC 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/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1 |
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Synonyms | Value | Source |
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(R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide | ChEBI | 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine | ChEBI | 1,2-Dioleoyl-L-alpha-lecithin | ChEBI | 1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine | ChEBI | 1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholine | ChEBI | Dioleoyl lecithin | ChEBI | Dioleoyl phosphatidylcholine | ChEBI | PC 18:1 | ChEBI | PC(18:1(9Z)/18:1(9Z)) | ChEBI | PC(18:1/18:1) | ChEBI | Phosphatidylcholine 18:1 | ChEBI | 1,2-Dioleoyl-L-a-lecithin | Generator | 1,2-Dioleoyl-L-α-lecithin | Generator | 1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine | HMDB | 1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholine | MeSH | Dioleylphosphatidylcholine | MeSH | 1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer | MeSH | Dielaidoylphosphatidylcholine | MeSH | Dioleoylphosphatidylcholine | MeSH | 1,2-Dioleoylglycerophosphocholine | MeSH | 1,2-Oleoyl-sn-glycero-3-phosphocholine | MeSH | DOPC | MeSH | Dielaidinoyl lecithin | MeSH | 1,2-DOCPC | MeSH | 1,2-Dioleoyl glycerophosphocholine | MeSH | 1,2-Dioleoyl-sn-glycero-3-phosphocholine | MeSH | 1,2-Oleoylphosphatidylcholine | MeSH | 1,2-Dioleoyl-GPC | HMDB | 1,2-Dioleoyl-sn-glycero-phosphatidylcholine | HMDB | GPC(18:1(9Z)/18:1(9Z)) | HMDB | GPC(18:1/18:1) | HMDB | GPC(18:1n9/18:1n9) | HMDB | GPC(18:1w9/18:1w9) | HMDB | GPC(36:2) | HMDB | GPCho(18:1(9Z)/18:1(9Z)) | HMDB | GPCho(18:1/18:1) | HMDB | GPCho(18:1n9/18:1n9) | HMDB | GPCho(18:1w9/18:1w9) | HMDB | GPCho(36:2) | HMDB | PC(18:1n9/18:1n9) | HMDB | PC(18:1w9/18:1w9) | HMDB | PC(36:2) | HMDB | Phosphatidylcholine(18:1(9Z)/18:1(9Z)) | HMDB | Phosphatidylcholine(18:1/18:1) | HMDB | Phosphatidylcholine(18:1n9/18:1n9) | HMDB | Phosphatidylcholine(18:1w9/18:1w9) | HMDB | Phosphatidylcholine(36:2) | HMDB | 1,2-Dioleoyl-3-sn-phosphatidylcholine | HMDB | 1,2-Dioleoyl-sn-glycero-3-phosphochline | HMDB | 1,2-Dioleoyl-sn-glycero-3-phosphorylcholine | HMDB | 1,2-Dioleoyl-sn-phosphatidylcholine | HMDB | 1,2-Dioleoylphosphatidylcholine | HMDB | 1,2-Dioleyl-L-lecithin | HMDB | Dioleoyl L-alpha-lecithin | HMDB | Dioleoyl L-α-lecithin | HMDB | Dioleoyl-3-sn-phosphatidylcholine | HMDB | Dioleoyl-L-alpha-glycerophosphocholine | HMDB | Dioleoyl-L-alpha-glycerophosphorylcholine | HMDB | Dioleoyl-L-alpha-phosphatidylcholine | HMDB | Dioleoyl-L-α-glycerophosphocholine | HMDB | Dioleoyl-L-α-glycerophosphorylcholine | HMDB | Dioleoyl-L-α-phosphatidylcholine | HMDB | Dioleoyllecithin | HMDB | L-Dioleoyl lecithin | HMDB | L-Dioleoylphosphatidylcholine | HMDB | L-alpha-Di(cis-9-octadecanoyl) lecithin | HMDB | L-alpha-Dioleoyl phosphatidylcholine | HMDB | L-alpha-Dioleoyllecithin | HMDB | L-alpha-Dioleylphosphatidylcholine | HMDB | L-α-Di(cis-9-octadecanoyl) lecithin | HMDB | L-α-Dioleoyl phosphatidylcholine | HMDB | L-α-Dioleoyllecithin | HMDB | L-α-Dioleylphosphatidylcholine | HMDB | sn-3-Dioleoyllecithin | HMDB | 1,2-Dioleoylglycerol-3-phosphorylcholine | HMDB | 1,2-Dioleoylglyceryl-3-phosphorylcholine | HMDB | 1,2-Dioleoyllecithin | HMDB | Dioleoylglycerophosphocholine | HMDB | Dioleoylglycerophosphorylcholine | HMDB | Dioleoylglycerylphosphorylcholine | HMDB | Dioleyl lecithin | HMDB | Dioleyl phosphatidylcholine | 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 | (2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium |
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CAS Registry Number | 4235-95-4 |
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SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC |
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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/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1 |
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InChI Key | SNKAWJBJQDLSFF-NVKMUCNASA-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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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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Spectra |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 10V, Positive-QTOF | splash10-000i-0000000900-36f689a3cf8b031c9ce5 | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-0019-0600000900-4df68b8e85813f4b5ad8 | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-0f89-1900021300-f15a88b3adc3a38193cb | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 10V, Positive-QTOF | splash10-0a4i-0000000090-53a8e01f33b2af13f226 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-0a4i-0000000190-64f46bdfe255d6a5b5e4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-004k-0900139110-7365097ffb2d5d55b434 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 10V, Positive-QTOF | splash10-0006-0000000900-64c382f846ba04194d31 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-0006-0000000900-6c06686879d9f7790e62 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-0a59-0200249400-1ae2411ef15a63cb3b2d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 10V, Positive-QTOF | splash10-000i-0000000900-e54f4b7d729e27672b37 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 20V, Positive-QTOF | splash10-0019-0600000900-3a2440aaca7e87ec13a5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 40V, Positive-QTOF | splash10-0f89-1900021300-24d60344b49a468b0469 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 10V, Negative-QTOF | splash10-001i-0000000900-23df8d3c4971511f3b91 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 20V, Negative-QTOF | splash10-001i-0050030900-b121f3ff4b078b5df33e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 40V, Negative-QTOF | splash10-001i-1090200000-673c166236d767f9289e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 10V, Negative-QTOF | splash10-00di-0000000090-683d2aaf9f12a9d08614 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 20V, Negative-QTOF | splash10-00di-0010000090-37042360a3899f1fdc23 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PC(18:1(9Z)/18:1(9Z)) 40V, Negative-QTOF | splash10-00f0-0090000090-06eeedb644af6eeff7ec | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 44.5 (37.6-53.3) uM | Newborn (0-30 days old) | Not Available | Normal | | details | Blood | Detected and Quantified | 212 (183-244) uM | Infant (0-1 year old) | Not Available | Normal | | details | Blood | Detected and Quantified | 250.7 +/- 47.2 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 267.03(66.1) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 100.0-425.0 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.84 +/- 2 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 1.46 +/- 2.13 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 0.200 +/- 0.031 uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.016 (0.0021-0.045) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0833 +/- 0.2914 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 155.673 (140.706) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 279.018 (74.520) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 192.7 +/- 50.0 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 233.6 +/- 68.4 uM | Children (1-13 years old) | Both | Obesity | | details | Blood | Detected and Quantified | 220.75(59.14) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Urine | Detected and Quantified | 0.0127 +/- 0.0342 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 0.0219 +/- 0.0716 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
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Predicted Concentrations |
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Blood | 242.910 +/- 55.844 uM | Adult (>18 years old) | Both | Normal (Upper Limit) | NULL | Blood | 29.090 +/- 7.790 uM | Adult (>18 years old) | Both | Normal (Most Probable) | NULL |
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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.
| Eosinophilic esophagitis |
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- Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
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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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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8525772 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-2181 |
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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 | 10350317 |
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PDB ID | Not Available |
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ChEBI ID | 74669 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Tokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu. Preparation of phosphatidylcholines. Jpn. Kokai Tokkyo Koho (1989), 6 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Myher JJ, Kuksis A, Pind S: Molecular species of glycerophospholipids and sphingomyelins of human plasma: comparison to red blood cells. Lipids. 1989 May;24(5):408-18. [PubMed:2755318 ]
- Smith RE, Daleke DL: Phosphatidylserine transport in Rhnull erythrocytes. Blood. 1990 Sep 1;76(5):1021-7. [PubMed:2118395 ]
- Pigault C, Follenius-Wund A, Schmutz M, Freyssinet JM, Brisson A: Formation of two-dimensional arrays of annexin V on phosphatidylserine-containing liposomes. J Mol Biol. 1994 Feb 11;236(1):199-208. [PubMed:8107105 ]
- Knight JD, Miranker AD: Phospholipid catalysis of diabetic amyloid assembly. J Mol Biol. 2004 Aug 27;341(5):1175-87. [PubMed:15321714 ]
- Grasso P, Dattatreyamurty B, Reichert LE Jr: Reconstitution of hormone-responsive detergent-solubilized follicle stimulating hormone receptors into liposomes. Mol Endocrinol. 1988 May;2(5):420-30. [PubMed:3138532 ]
- Finean JB, Hutchinson AL: X-ray diffraction studies of lipid phase transitions in cholesterol-rich membranes at sub-zero temperatures. Chem Phys Lipids. 1988 Jan;46(1):63-71. [PubMed:3338100 ]
- Pinnaduwage P, Huang L: The role of protein-linked oligosaccharide in the bilayer stabilization activity of glycophorin A for dioleoylphosphatidylethanolamine liposomes. Biochim Biophys Acta. 1989 Nov 17;986(1):106-14. [PubMed:2819088 ]
- Seppen J, Jansen PL, Oude Elferink RP: Immunoaffinity purification and reconstitution of the human bilirubin/phenol UDP-glucuronosyltransferase family. Protein Expr Purif. 1995 Apr;6(2):149-54. [PubMed:7606162 ]
- Larsen CE, Alford DR, Young LJ, McGraw TP, Duzgunes N: Fusion of simian immunodeficiency virus with liposomes and erythrocyte ghost membranes: effects of lipid composition, pH and calcium. J Gen Virol. 1990 Sep;71 ( Pt 9):1947-55. [PubMed:2120385 ]
- Anderluh G, Gutierrez-Aguirre I, Rabzelj S, Ceru S, Kopitar-Jerala N, Macek P, Turk V, Zerovnik E: Interaction of human stefin B in the prefibrillar oligomeric form with membranes. Correlation with cellular toxicity. FEBS J. 2005 Jun;272(12):3042-51. [PubMed:15955063 ]
- Billy D, Speijer H, Lindhout T, Hemker HC, Willems GM: Inhibition of prothrombinase at macroscopic lipid membranes: competition between antithrombin and prothrombin. Biochemistry. 1995 Oct 17;34(41):13699-704. [PubMed:7577961 ]
- Versluis AJ, Rensen PC, Kuipers ME, Love WG, Taylor PW: Interaction between zinc(II)-phthalocyanine-containing liposomes and human low density lipoprotein. J Photochem Photobiol B. 1994 May;23(2-3):141-8. [PubMed:8040754 ]
- Mahadevappa VG, Holub BJ: The molecular species composition of individual diacyl phospholipids in human platelets. Biochim Biophys Acta. 1982 Oct 14;713(1):73-9. [PubMed:7138900 ]
- Ritov VB, Menshikova EV, Kelley DE: High-performance liquid chromatography-based methods of enzymatic analysis: electron transport chain activity in mitochondria from human skeletal muscle. Anal Biochem. 2004 Oct 1;333(1):27-38. [PubMed:15351277 ]
- Takamura H, Kasai H, Arita H, Kito M: Phospholipid molecular species in human umbilical artery and vein endothelial cells. J Lipid Res. 1990 Apr;31(4):709-17. [PubMed:2351875 ]
- Itoh K, Suzuki A, Kuroki Y, Akino T: High performance liquid chromatographic separation of diacylglycerol acetates to quantitate disaturated species of lung phosphatidylcholine. Lipids. 1985 Sep;20(9):611-6. [PubMed:4046747 ]
- Wang Z, Klipfell E, Bennett BJ, Koeth R, Levison BS, Dugar B, Feldstein AE, Britt EB, Fu X, Chung YM, Wu Y, Schauer P, Smith JD, Allayee H, Tang WH, DiDonato JA, Lusis AJ, Hazen SL: Gut flora metabolism of phosphatidylcholine promotes cardiovascular disease. Nature. 2011 Apr 7;472(7341):57-63. doi: 10.1038/nature09922. [PubMed:21475195 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Furse S, de Kroon AI: Phosphatidylcholine's functions beyond that of a membrane brick. Mol Membr Biol. 2015;32(4):117-9. doi: 10.3109/09687688.2015.1066894. Epub 2015 Aug 25. [PubMed:26306852 ]
- Exton JH: Signaling through phosphatidylcholine breakdown. J Biol Chem. 1990 Jan 5;265(1):1-4. [PubMed:2104616 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
- Li, Zhaoyu, and Dennis E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylcholine and choline homeostasis. Journal of Lipid Research.
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