Record Information |
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Version | 5.0 |
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Status | Predicted |
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Creation Date | 2021-09-12 12:28:17 UTC |
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Update Date | 2022-11-30 19:56:39 UTC |
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HMDB ID | HMDB0267191 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) |
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Description | PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)), in particular, consists of one chain of one 18-methyleicosanoyl at the C-1 position and one chain of Protectin DX at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396 ). |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C/C=C/[C@@H](O)C\C=C/CC InChI=1S/C46H79O10P/c1-4-6-25-33-42(47)35-28-23-24-29-36-43(48)34-27-20-17-18-22-31-38-46(50)56-44(40-55-57(51,52)53)39-54-45(49)37-30-21-16-14-12-10-8-7-9-11-13-15-19-26-32-41(3)5-2/h6,18,20,22-25,27-29,35-36,41-44,47-48H,4-5,7-17,19,21,26,30-34,37-40H2,1-3H3,(H2,51,52,53)/b22-18-,24-23-,25-6-,27-20-,35-28+,36-29+/t41?,42-,43+,44+/m0/s1 |
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Synonyms | Value | Source |
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[(2R)-2-{[(4Z,7Z,10R,11E,13Z,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy]phosphonate | Generator |
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Chemical Formula | C46H79O10P |
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Average Molecular Weight | 823.102 |
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Monoisotopic Molecular Weight | 822.541085742 |
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IUPAC Name | [(2R)-2-{[(4Z,7Z,10R,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-{[(4Z,7Z,10R,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoyl]oxy}-3-[(18-methylicosanoyl)oxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C/C=C/[C@@H](O)C\C=C/CC |
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InChI Identifier | InChI=1S/C46H79O10P/c1-4-6-25-33-42(47)35-28-23-24-29-36-43(48)34-27-20-17-18-22-31-38-46(50)56-44(40-55-57(51,52)53)39-54-45(49)37-30-21-16-14-12-10-8-7-9-11-13-15-19-26-32-41(3)5-2/h6,18,20,22-25,27-29,35-36,41-44,47-48H,4-5,7-17,19,21,26,30-34,37-40H2,1-3H3,(H2,51,52,53)/b22-18-,24-23-,25-6-,27-20-,35-28+,36-29+/t41?,42-,43+,44+/m0/s1 |
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InChI Key | LGRSBRWKEOPOQO-YXEJNTIBSA-N |
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Chemical Taxonomy |
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Classification | Not classified |
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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 | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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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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PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C/C=C/[C@@H](O)C\C=C/CC | 5983.8 | Standard polar | 33892256 | PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C/C=C/[C@@H](O)C\C=C/CC | 4884.5 | Standard non polar | 33892256 | PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C/C=C/[C@@H](O)C\C=C/CC | 6044.0 | 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 - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | 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 - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 10V, Positive-QTOF | splash10-0002-0000000090-9d79ff5ef27775b8f95c | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 20V, Positive-QTOF | splash10-0002-0000000990-d6a916df20a23f271c23 | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 40V, Positive-QTOF | splash10-00kk-0000390340-b811986ae01cf012a8e7 | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 10V, Negative-QTOF | splash10-00di-0000000090-694489f29c2fd98dc15d | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 20V, Negative-QTOF | splash10-08os-0006900040-bdb5c5f995114672ff57 | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 40V, Negative-QTOF | splash10-056r-0009200000-7f0775ecd68f7baf9aa6 | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 10V, Positive-QTOF | splash10-0ab9-0000000090-709b004595278659b69c | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 20V, Positive-QTOF | splash10-00fr-0000000590-0aea4b98de89a747c683 | 2021-09-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(a-21:0/22:6(4Z,7Z,11E,13Z,15E,19Z)-2OH(10S,17)) 40V, Positive-QTOF | splash10-01ta-0000900620-7e1abd9a79366e47e2cd | 2021-09-28 | Wishart Lab | View Spectrum |
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