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 04:18:56 UTC |
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Update Date | 2022-11-30 19:26:08 UTC |
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HMDB ID | HMDB0115307 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) |
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Description | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids 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. PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)), in particular, consists of one chain of docosadienoic acid at the C-1 position and one chain of stearidonic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. |
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Structure | [H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C43H73O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,23,28,30,41H,3-5,7,9-10,15-16,20-22,24-27,29,31-40H2,1-2H3,(H2,46,47,48)/b8-6-,13-11-,14-12-,19-17-,23-18-,30-28-/t41-/m1/s1 |
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Synonyms | Value | Source |
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1-docosadienoyl-2-stearidonoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-docosadienoyl-2-stearidonoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:2/18:4) | SMPDB, HMDB | PA(22:2n6/18:4n3) | SMPDB, HMDB | PA(22:2w6/18:4w3) | SMPDB, HMDB | PA(40:6) | SMPDB, HMDB | Phosphatidic acid(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) | SMPDB, HMDB | Phosphatidic acid(22:2/18:4) | SMPDB, HMDB | Phosphatidic acid(22:2n6/18:4n3) | SMPDB, HMDB | Phosphatidic acid(22:2w6/18:4w3) | SMPDB, HMDB | Phosphatidic acid(40:6) | SMPDB, HMDB | Phosphatidate(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) | SMPDB, HMDB | Phosphatidate(22:2/18:4) | SMPDB, HMDB | Phosphatidate(22:2n6/18:4n3) | SMPDB, HMDB | Phosphatidate(22:2w6/18:4w3) | SMPDB, HMDB | Phosphatidate(40:6) | SMPDB, HMDB | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) | SMPDB |
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Chemical Formula | C43H73O8P |
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Average Molecular Weight | 749.023 |
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Monoisotopic Molecular Weight | 748.504306309 |
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IUPAC Name | [(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C43H73O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-25-27-29-31-33-35-37-42(44)49-39-41(40-50-52(46,47)48)51-43(45)38-36-34-32-30-28-26-23-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,23,28,30,41H,3-5,7,9-10,15-16,20-22,24-27,29,31-40H2,1-2H3,(H2,46,47,48)/b8-6-,13-11-,14-12-,19-17-,23-18-,30-28-/t41-/m1/s1 |
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InChI Key | OMWHOEUMTCNMLI-GWCDUGDCSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains 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 | Glycerophosphates |
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Direct Parent | 1,2-diacylglycerol-3-phosphates |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dicarboxylic acid or derivatives
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- 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 | Not Available |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)) (PathBank: SMP0025174)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0025175)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0025176)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0025177)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0025178)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0025179)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0025180)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025181)
- De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025182)
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) | [H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC | 5415.7 | Standard polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) | [H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC | 4615.7 | Standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) | [H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC | 5318.3 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 5344.7 | Semi standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 4705.0 | Standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 5528.9 | Standard polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5323.4 | Semi standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4666.8 | Standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4852.1 | Standard polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5562.8 | Semi standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4811.1 | Standard non polar | 33892256 | PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5530.8 | Standard polar | 33892256 |
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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 - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 10V, Positive-QTOF | splash10-07l2-1188903700-ae5b1f30ac05890541a4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 20V, Positive-QTOF | splash10-0aos-3289403100-ce28ce7e33b7baf8cc6f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 40V, Positive-QTOF | splash10-00mo-1189003000-e9b67ab3c83ed2bf4c1e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 10V, Negative-QTOF | splash10-00p1-4049400300-8a34f2a486908bfa53a2 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 20V, Negative-QTOF | splash10-004i-9014000000-a5ca567a2a5b5d126bc8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 40V, Negative-QTOF | splash10-004i-9000000000-9c8fff7ec01877ef8ea9 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 10V, Positive-QTOF | splash10-001j-0000000900-ae7430b3d3c19c2ff546 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 20V, Positive-QTOF | splash10-0f6t-0000005900-47901d33f4a90360f76b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 40V, Positive-QTOF | splash10-0w90-0000906200-7959f4764cadb71675a2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 10V, Positive-QTOF | splash10-00di-0000000900-8a9781fb0eb02f3c5f74 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 20V, Positive-QTOF | splash10-00di-0000009900-1b29abe610d539f1fcb5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 40V, Positive-QTOF | splash10-0fkj-0000922400-8b636c6328474c02e517 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 10V, Negative-QTOF | splash10-0002-0000000900-21194b677cfc246e25b0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 20V, Negative-QTOF | splash10-020a-0033900400-0844355d73a43b010cdb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:2(13Z,16Z)/18:4(6Z,9Z,12Z,15Z)) 40V, Negative-QTOF | splash10-002r-1169600100-fea905ceacebfc070a5c | 2021-09-24 | Wishart Lab | View Spectrum |
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Pathways | |
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