Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-25 13:35:43 UTC |
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Update Date | 2022-03-07 02:51:02 UTC |
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HMDB ID | HMDB0010686 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) |
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Description | PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of adrenic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the adrenic acid moiety is derived from animal fats. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. 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. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. |
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Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C46H77O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,21-23,26,28,43-44,47-48H,3-5,7,9-10,15-16,20,24-25,27,29-42H2,1-2H3,(H,51,52)/b8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t43-,44+/m0/s1 |
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Synonyms | Value | Source |
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1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-a-Linolenoyl-2-adrenoyl-sn-glycero-3-phosphoglycerol | HMDB | 1-alpha-Linolenoyl-2-adrenoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(18:3/22:4) | HMDB | GPG(18:3N3/22:4N6) | HMDB | GPG(18:3W3/22:4W6) | HMDB | GPG(40:7) | HMDB | PG(18:3/22:4) | HMDB | PG(18:3N3/22:4N6) | HMDB | PG(18:3W3/22:4W6) | HMDB | PG(40:7) | HMDB | Phosphatidylglycerol(18:3/22:4) | HMDB | Phosphatidylglycerol(18:3n3/22:4n6) | HMDB | Phosphatidylglycerol(18:3W3/22:4W6) | HMDB | Phosphatidylglycerol(40:7) | HMDB | 1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoglycerol | HMDB | PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) | Lipid Annotator |
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Chemical Formula | C46H77O10P |
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Average Molecular Weight | 821.0713 |
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Monoisotopic Molecular Weight | 820.525435196 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy(2R)-2-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C46H77O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,21-23,26,28,43-44,47-48H,3-5,7,9-10,15-16,20,24-25,27,29-42H2,1-2H3,(H,51,52)/b8-6-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t43-,44+/m0/s1 |
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InChI Key | ZACXWNLBOWEKJK-YDYSYWMXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. |
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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 | Glycerophosphoglycerols |
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Direct Parent | Phosphatidylglycerols |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | 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 | Not Available |
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Predicted Molecular Properties | |
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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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PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5726.7 | Standard polar | 33892256 | PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4890.9 | Standard non polar | 33892256 | PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 5793.4 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-19 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 10V, Positive-QTOF | splash10-0i99-5086432190-978fdaed40693a1b9339 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 20V, Positive-QTOF | splash10-0mmi-6195221220-3d7a08eed4a97d28d51c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 40V, Positive-QTOF | splash10-0ap0-9087003200-56955c54488ce05d203f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 10V, Negative-QTOF | splash10-0arr-1193110130-b84d530a80257bb62f48 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 20V, Negative-QTOF | splash10-004i-5291100000-a2b3a583add2f21f3da7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 40V, Negative-QTOF | splash10-004i-9011000000-694a4ac1abfc5a469023 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 10V, Negative-QTOF | splash10-014i-0000000090-b6d6d99aea224a6eafb1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 20V, Negative-QTOF | splash10-017i-0199440090-01fae537269a3f7f839c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) 40V, Negative-QTOF | splash10-017i-0399440090-3dedc0b04d477eec7944 | 2021-09-23 | Wishart Lab | View Spectrum |
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