Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 08:21:38 UTC |
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Update Date | 2022-11-30 19:26:38 UTC |
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HMDB ID | HMDB0116511 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) |
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Description | PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerophosphate (PGP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant (up to 11% of the total). It is well established that the concentration of phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for cardiolipin synthesis. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of clupanodonic acid at the C-2 position. They are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to phosphatidylglycerols (PGs). 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. |
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Structure | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C50H78O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-49(52)59-45-48(46-62-65(57,58)61-44-47(51)43-60-64(54,55)56)63-50(53)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29-32,35,37,47-48,51H,3-4,9-10,15-16,21-22,27-28,33-34,36,38-46H2,1-2H3,(H,57,58)(H2,54,55,56)/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-/t47-,48+/m0/s1 |
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Synonyms | Value | Source |
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1-docosahexaenoyl-2-clupanodonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | SMPDB, HMDB | PGP(22:6/22:5) | SMPDB, HMDB | PGP(22:6n3/22:5n3) | SMPDB, HMDB | PGP(22:6w3/22:5w3) | SMPDB, HMDB | PGP(44:11) | SMPDB, HMDB | PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB | 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | Lipid Annotator, HMDB | PGP(22:6/22:5) | Lipid Annotator | 1-docosahexaenoyl-2-docosapentaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | [(2S)-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C50H78O13P2 |
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Average Molecular Weight | 949.109 |
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Monoisotopic Molecular Weight | 948.491766568 |
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IUPAC Name | [(2S)-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid |
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Traditional Name | (2S)-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)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/C50H78O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-49(52)59-45-48(46-62-65(57,58)61-44-47(51)43-60-64(54,55)56)63-50(53)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29-32,35,37,47-48,51H,3-4,9-10,15-16,21-22,27-28,33-34,36,38-46H2,1-2H3,(H,57,58)(H2,54,55,56)/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,37-35-/t47-,48+/m0/s1 |
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InChI Key | SNFTWDOGXXEYHM-VHDGMZLBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-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 | Glycerophosphoglycerophosphates |
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Direct Parent | Phosphatidylglycerophosphates |
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Alternative Parents | |
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Substituents | - Diacylglycerophosphoglycerophosphate
- Sn-glycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- 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 | Not Available |
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Disposition | Not Available |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030230)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030231)
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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 IndicesNot Available |
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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 - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-03ea-1229008026-108983db781597626719 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-03yi-3259015213-260f5ced4f780eedfeb8 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0a4r-8339015031-353500e5056d7ac373eb | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-004i-4029003003-9ce944c8de24f45ac139 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-004i-9013000000-d54c7f0f93e9e8aee9d4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-9001000000-cbc0d7841bc90ad1be97 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-0002-0010000009-07edb8633432ecd95ab9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-0fr2-3042009002-b0bd990edc467636dd3a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-0udi-3092105000-d27a584c45d05462c736 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0f6t-1000002193-24e0918c5dde2762d909 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0kbb-1200002960-4fd9b79caaf70bf290ad | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0v00-0096010110-70a7bdac7d5754656918 | 2021-09-24 | Wishart Lab | View Spectrum |
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