| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-07-13 19:53:20 UTC |
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| Update Date | 2021-04-30 20:57:44 UTC |
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| Lmdb | LMDB00595 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | PC(o-18:0/18:0) |
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| Description | PC(o-18:0/18:0) 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(o-18:0/18:0), in particular, consists of one chain of Stearyl alcohol at the C-1 position and one chain of stearic acid at the C-2 position. The Stearyl alcohol moiety is derived from beef fat, fish 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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| 1-Stearyl-2-stearoyl-sn-glycero-3-phosphocholine | ChEBI | | Gpcho(18:0/18:0) | HMDB | | Gpcho(36:0) | HMDB | | Lecithin | HMDB | | PC Ae C36:0 | HMDB | | PC(18:0/18:0) | HMDB | | PC(36:0) | HMDB | | PC(O-36:0) | HMDB | | Phosphatidylcholine(18:0/18:0) | HMDB | | Phosphatidylcholine(36:0) | HMDB | | 1-Octadecanyl-2-octadecanoyl-sn-glycero-3-phosphocholine | HMDB | | PC(o-18:0/18:0) | Lipid Annotator |
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| Chemical Formula | C44H90NO7P |
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| Average Molecular Weight | 776.1617 |
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| Monoisotopic Molecular Weight | 775.645490751 |
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| IUPAC Name | trimethyl(2-{[(2R)-2-(octadecanoyloxy)-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)azanium |
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| Traditional Name | trimethyl(2-{[(2R)-2-(octadecanoyloxy)-3-(octadecyloxy)propyl phosphonato]oxy}ethyl)azanium |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@](COCCCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC |
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| InChI Identifier | InChI=1S/C44H90NO7P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-39-49-41-43(42-51-53(47,48)50-40-38-45(3,4)5)52-44(46)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h43H,6-42H2,1-5H3/t43-/m1/s1 |
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| InChI Key | BKEDGKIMIUGHDV-VZUYHUTRSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position. |
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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 | 1-alkyl,2-acylglycero-3-phosphocholines |
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| Alternative Parents | |
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| Substituents | - 1-alkyl,2-acylglycero-3-phosphocholine
- Phosphocholine
- Fatty acid ester
- Dialkyl phosphate
- Glycerol ether
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Fatty acyl
- Alkyl phosphate
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Carboxylic acid ester
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- Organic nitrogen compound
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- 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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| Status | Detected and Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Not Available |
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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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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-9131231300-3269f93c01b50f55a593 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0w39-8495142200-62834169ff0cea12b50f | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002r-9065023100-39735f29541a51fd17db | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00e9-0070002900-ab24c938c11a317e5c49 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00yi-1090106300-1cab09bacff369aadba3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-017r-3090100000-121e010cf145f8c95c6a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000000090-fed651ecec1c0a5ae81c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0000000090-fed651ecec1c0a5ae81c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001k-0070301910-9b9daddaaddef406181c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0000000900-73e988477c4fb55209fa | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0000000900-73e988477c4fb55209fa | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-003r-1900160700-3c1c1d9979527c478cfb | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0000000900-005e67f1374cac2f3816 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0010010900-a5cd73889eecc93680c0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-3091201000-af22d94548317ee67aec | Spectrum |
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| Serum | Detected and Quantified | 2.3104 +/- 0.4036 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.4234 +/- 1.0084 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.4749 +/- 0.6412 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 1.77 +/- 0.82 uM | Not Available | Ovine | | details | | Serum | Detected and Quantified | 2.4625 +/- 0.5862 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.2617 +/- 0.6178 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.6223 +/- 0.653 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.7293 +/- 1.4068 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.5832 +/- 1.0201 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 0.41 uM | Not Available | Porcine | | details | | Serum | Detected and Quantified | 0.44 uM | Not Available | Porcine | | details | | Serum | Detected and Quantified | 0.33 uM | Not Available | Porcine | | details | | Serum | Detected and Quantified | 0.4 uM | Not Available | Porcine | | details | | Serum | Detected but not Quantified | Not Applicable | Not Available | Caprine | | details | | Serum | Detected and Quantified | 2.5233 +/- 0.9128 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.3519 +/- 0.6813 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.6126 +/- 0.648 uM | Normal | Ovine | | details | | Serum | Detected and Quantified | 2.2891 +/- 0.6298 uM | Normal | Ovine | | details |
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