Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2008-09-12 01:46:41 UTC |
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Update Date | 2022-11-30 19:03:24 UTC |
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HMDB ID | HMDB0009011 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) |
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Description | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines 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. PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the docosapentaenoic acid moiety is derived from fish oils. 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. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C45H80NO8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-45(48)54-43(42-53-55(49,50)52-40-39-46)41-51-44(47)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,43H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-42,46H2,1-2H3,(H,49,50)/b7-5-,13-11-,19-17-,22-21-,28-26-/t43-/m1/s1 |
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Synonyms | Value | Source |
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PE(40:5) | HMDB | GPEtn(40:5) | HMDB | PE(18:0/22:5) | HMDB | 1-Stearoyl-2-docosapentaenoyl-sn-glycero-3-phosphoethanolamine | HMDB | Phophatidylethanolamine(40:5) | HMDB | Phophatidylethanolamine(18:0/22:5) | HMDB | 1-Octadecanoyl-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphoethanolamine | HMDB | GPEtn(18:0/22:5) | HMDB | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) | Lipid Annotator |
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Chemical Formula | C45H80NO8P |
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Average Molecular Weight | 794.0924 |
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Monoisotopic Molecular Weight | 793.562155053 |
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IUPAC Name | (2-aminoethoxy)[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(octadecanoyloxy)propoxy]phosphinic acid |
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Traditional Name | 2-aminoethoxy(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-(octadecanoyloxy)propoxyphosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C45H80NO8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-45(48)54-43(42-53-55(49,50)52-40-39-46)41-51-44(47)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,43H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-42,46H2,1-2H3,(H,49,50)/b7-5-,13-11-,19-17-,22-21-,28-26-/t43-/m1/s1 |
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InChI Key | KYERVKWKQQBRQB-LKDUQXRXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages. |
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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 | Glycerophosphoethanolamines |
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Direct Parent | Phosphatidylethanolamines |
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Alternative Parents | |
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Substituents | - Diacylglycero-3-phosphoethanolamine
- Phosphoethanolamine
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Amino acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Primary aliphatic amine
- Organic nitrogen compound
- Primary amine
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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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 | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5430.4 | Standard polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5091.5 | Standard non polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5620.0 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(OCCN)O[Si](C)(C)C | 5650.9 | Semi standard non polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(OCCN)O[Si](C)(C)C | 4755.1 | Standard non polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(OCCN)O[Si](C)(C)C | 6862.8 | Standard polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #2 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)OCCN[Si](C)(C)C | 5736.0 | Semi standard non polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #2 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)OCCN[Si](C)(C)C | 5063.7 | Standard non polar | 33892256 | PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)),1TMS,isomer #2 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)OCCN[Si](C)(C)C | 6698.7 | Standard polar | 33892256 |
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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 - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-0006-0011000900-3bddc2a079291fb113cf | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-0006-0011000900-3bddc2a079291fb113cf | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-0063-0399330600-e31184a86ca724adb818 | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0006-0000001900-be96a044a097c279617c | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0udl-0003339700-843cfc76a2d3649c14ac | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0udi-0003339300-e5466a5df03ac8788cd0 | 2017-10-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-0006-0011000900-8c9736c1b20dd0c8fc1d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-0006-0011000900-8c9736c1b20dd0c8fc1d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-0063-0399330600-249cb49241312f35b2f0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-014i-0000001090-55a6a361777a4e9b0bb1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-014i-0000002290-8061fa3df4f4297b8c87 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-00di-0100301910-2f50bd087caea814781e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0006-0000001900-86ca62939332397afd59 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0udl-0003339700-3bd7da243c0a0f5682ff | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0udi-0003339300-73880288d48571a96ac8 | 2021-09-24 | 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 | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details |
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Predicted Concentrations |
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Blood | 0.827 +/- 0.246 uM | Adult (>18 years old) | Both | Normal (Most Probable) | Calculated using MetaboAnalyst | Blood | 6.433 +/- 1.332 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 | None |
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Associated OMIM IDs | None |
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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 | 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 | 53479612 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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 | 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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