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 08:41:16 UTC |
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Update Date | 2022-11-30 19:26:41 UTC |
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HMDB ID | HMDB0116603 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) |
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Description | PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) is a phosphatidylglycerol - 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of dihomo-gamma-linolenic acid at the C-2 position. 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 (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 cardiolipin synthesis. |
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Structure | [H][C@](O)(CO)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)CCCCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C48H77O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-47(51)55-43-46(44-57-59(53,54)56-42-45(50)41-49)58-48(52)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,22,24,26-29,33,35,45-46,49-50H,3-4,6,8-10,15-16,21,23,25,30-32,34,36-44H2,1-2H3,(H,53,54)/b7-5-,13-11-,14-12-,19-17-,20-18-,24-22-,28-26-,29-27-,35-33-/t45-,46+/m0/s1 |
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Synonyms | Value | Source |
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1-Docosahexaenoyl-2-dihomo-gamma-linolenoyl-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-Docosahexaenoyl-2-dihomo-gamma-linolenoyl-sn-glycero-3-phosphoglycerol | HMDB | PG(22:6/20:3) | HMDB | PG(22:6N3/20:3N6) | HMDB | PG(22:6W3/20:3W6) | HMDB | PG(42:9) | HMDB | Phosphatidylglycerol(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) | HMDB | Phosphatidylglycerol(22:6/20:3) | HMDB | Phosphatidylglycerol(22:6n3/20:3n6) | HMDB | Phosphatidylglycerol(22:6W3/20:3W6) | HMDB | Phosphatidylglycerol(42:9) | HMDB | GPG(42:9) | HMDB | GPG(22:6/20:3) | HMDB | 1-Docosahexaenoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoglycerol | HMDB | 1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphoglycerol | HMDB | 1-docosahexaenoyl-2-dihomo-gamma-linolenoyl-sn-glycero-3-phospho-(1'-glycerol) | SMPDB, HMDB | 1-docosahexaenoyl-2-dihomo-gamma-linolenoyl-sn-glycero-3-phosphoglycerol | SMPDB, HMDB | PG(22:6/20:3) | SMPDB, HMDB | PG(22:6n3/20:3n6) | SMPDB, HMDB | PG(22:6w3/20:3w6) | SMPDB, HMDB | PG(42:9) | SMPDB, HMDB | Phosphatidylglycerol(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) | SMPDB, HMDB | Phosphatidylglycerol(22:6/20:3) | SMPDB, HMDB | Phosphatidylglycerol(22:6n3/20:3n6) | SMPDB, HMDB | Phosphatidylglycerol(22:6w3/20:3w6) | SMPDB, HMDB | PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) | SMPDB |
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Chemical Formula | C48H77O10P |
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Average Molecular Weight | 845.108 |
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Monoisotopic Molecular Weight | 844.525435677 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy((2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy)phosphinic 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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C48H77O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-47(51)55-43-46(44-57-59(53,54)56-42-45(50)41-49)58-48(52)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,22,24,26-29,33,35,45-46,49-50H,3-4,6,8-10,15-16,21,23,25,30-32,34,36-44H2,1-2H3,(H,53,54)/b7-5-,13-11-,14-12-,19-17-,20-18-,24-22-,28-26-,29-27-,35-33-/t45-,46+/m0/s1 |
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InChI Key | FQAGNBJSYCGJTJ-KKGNRJEUSA-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. |
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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 | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z)) (PathBank: SMP0080413)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0095687)
- Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z)) (PathBank: SMP0080412)
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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 | | 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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PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) | [H][C@](O)(CO)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)CCCCCC\C=C/C\C=C/C\C=C/CCCCC | 6126.0 | Standard polar | 33892256 | PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) | [H][C@](O)(CO)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)CCCCCC\C=C/C\C=C/C\C=C/CCCCC | 5023.0 | Standard non polar | 33892256 | PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) | [H][C@](O)(CO)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)CCCCCC\C=C/C\C=C/C\C=C/CCCCC | 6004.6 | Semi standard non 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 - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-004r-5077082290-730fb8b659377c548fe0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-004r-5194041320-9f81b7d9eddca34b4d9a | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0cg0-9078011210-b98fd6e2f20d0c192f8d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0a6r-0119020030-863bf18c3df9b422c1e7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-004i-6229110100-09127da84e8c02c8e021 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9002000000-36e7a5ac114ec1945558 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0006-0000000090-780d1b34c2a775a6836e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-0a6x-0009130040-ea32b225c03fef7b6a15 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-054o-0109130040-7e7202dc66d7d5a50646 | 2021-09-23 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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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 | 74878315 |
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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 | 52927103 |
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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 | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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