Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:57:44 UTC |
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Update date | 2020-04-06 23:42:07 UTC |
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Primary ID | FDB029569 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | PGP(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) |
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Description | PGP(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. 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. PGP(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. 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 at 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 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. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. [HMDB] |
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CAS Number | Not Available |
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Structure | |
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Synonyms | Synonym | Source |
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3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | Lipid Annotator, HMDB | PGP(36:6) | Lipid Annotator, HMDB | PGP(18:3/18:3) | Lipid Annotator, HMDB | 1-g-linolenoyl-2-a-linolenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | 1-(6Z,9Z,12Z-octadecatrienoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | PGP(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) | Lipid Annotator | 1-gamma-Linolenoyl-2-alpha-linolenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | HMDB | PGP(18:3n6/18:3n3) | HMDB | PGP(18:3W6/18:3W3) | HMDB | 1-g-Linolenoyl-2-a-linolenoyl-sn-glycero-3-O-(1'-sn-glycerol-3'-ate) | HMDB | 1-gamma-Linolenoyl-2-alpha-linolenoyl-sn-glycero-3-O-(1'-sn-glycerol-3'-ate) | HMDB | 1-gamma-linolenoyl-2-alpha-linolenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | hmdb | PGP(18:3w6/18:3w3) | hmdb |
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Predicted Properties | |
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Chemical Formula | C42H72O13P2 |
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IUPAC name | [(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid |
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InChI Identifier | InChI=1S/C42H72O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(44)51-37-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)55-42(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,23,25,39-40,43H,3-5,7,9-10,15-16,21-22,24,26-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b8-6-,13-11-,14-12-,19-17-,20-18-,25-23-/t39-,40+/m0/s1 |
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InChI Key | ZJHYYYMMMZELQG-RYYNODHJSA-N |
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Isomeric SMILES | CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@]([H])(COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC |
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Average Molecular Weight | 846.9608 |
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Monoisotopic Molecular Weight | 846.444815414 |
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Classification |
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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 | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-02vj-1361191260-9650504037adb1b05236 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-07y1-4494173220-3097f273f83ab00f654f | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9346252400-a4f1e6e635df4ba24df5 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-4090020020-309065d445cf2a245145 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9050000000-832a3aec3d2eb70cb5cd | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-df6dabb5bc477029b12c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-3210090870-9cf99b4f014ce94c9bfc | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052b-1200036900-d1817ace5165c3e6102d | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0200940000-72771ffdbeaabfd7604c | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000000090-2d8b053a27884e47dd40 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002b-9060053060-8ef1557d2cc317e15b3d | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-6090000010-423076f8e84633f303ca | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 53481887 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB13569 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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