Record Information |
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Version | 1.0 |
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Created at | 2022-09-10 21:01:25 UTC |
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Updated at | 2022-09-10 21:01:25 UTC |
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NP-MRD ID | NP0305302 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid |
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Description | PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as GPG(18:2/22:6) Or GPG(40:8), 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. Thus, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphoglycerol lipid molecule. PG also serves as a precursor for the synthesis of cardiolipin. 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. 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). PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions. In particular, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PGP(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1. In addition, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and CDP-DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and cytidine monophosphate; which is catalyzed by the enzyme cardiolipin synthase. In humans, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in cardiolipin biosynthesis. The linoleic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. 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. 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. (2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid is found in Trypanosoma brucei. It was first documented in 1995 (PMID: 7834746). PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position (PMID: 11413487) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
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Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C46H75O10P/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/h5,7,11-14,17-19,21-23,26,28,32,34,43-44,47-48H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1 |
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Synonyms | Value | Source |
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1-(9Z,12Z-Octadecadienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-glycerol) | HMDB | 1-Linoleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(18:2/22:6) | HMDB | GPG(18:2N6/22:6N3) | HMDB | GPG(18:2W6/22:6W3) | HMDB | GPG(40:8) | HMDB | PG(18:2/22:6) | HMDB | PG(18:2N6/22:6N3) | HMDB | PG(18:2W6/22:6W3) | HMDB | PG(40:8) | HMDB | Phosphatidylglycerol(18:2/22:6) | HMDB | Phosphatidylglycerol(18:2n6/22:6n3) | HMDB | Phosphatidylglycerol(18:2W6/22:6W3) | HMDB | Phosphatidylglycerol(40:8) | HMDB | 1-(9Z,12Z-Octadecadienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoglycerol | HMDB | PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | Lipid Annotator |
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Chemical Formula | C46H75O10P |
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Average Mass | 819.0555 Da |
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Monoisotopic Mass | 818.50979 Da |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C46H75O10P/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/h5,7,11-14,17-19,21-23,26,28,32,34,43-44,47-48H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1 |
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InChI Key | GMXYXYLCBAOPHA-KNVYJNGISA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
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| Not Available | Species |
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Species of Origin | |
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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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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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