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 04:35:01 UTC |
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Update Date | 2022-11-30 19:26:10 UTC |
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HMDB ID | HMDB0115391 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) |
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Description | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 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(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of clupanodonic acid at the C-1 position and one chain of eicosapentaenoic 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)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C45H69O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-44(46)51-41-43(42-52-54(48,49)50)53-45(47)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,22,24,26-29,32,34,43H,3-4,9-10,15-16,21,23,25,30-31,33,35-42H2,1-2H3,(H2,48,49,50)/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,28-26-,29-27-,34-32-/t43-/m1/s1 |
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Synonyms | Value | Source |
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1-clupanodonoyl-2-eicosapentaenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-clupanodonoyl-2-eicosapentaenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:5/20:5) | SMPDB, HMDB | PA(22:5n3/20:5n3) | SMPDB, HMDB | PA(22:5w3/20:5w3) | SMPDB, HMDB | PA(42:10) | SMPDB, HMDB | Phosphatidic acid(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | SMPDB, HMDB | Phosphatidic acid(22:5/20:5) | SMPDB, HMDB | Phosphatidic acid(22:5n3/20:5n3) | SMPDB, HMDB | Phosphatidic acid(22:5w3/20:5w3) | SMPDB, HMDB | Phosphatidic acid(42:10) | SMPDB, HMDB | Phosphatidate(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | SMPDB, HMDB | Phosphatidate(22:5/20:5) | SMPDB, HMDB | Phosphatidate(22:5n3/20:5n3) | SMPDB, HMDB | Phosphatidate(22:5w3/20:5w3) | SMPDB, HMDB | Phosphatidate(42:10) | SMPDB, HMDB | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | SMPDB | [(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoyloxy]-2-[(5Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C45H69O8P |
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Average Molecular Weight | 769.013 |
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Monoisotopic Molecular Weight | 768.47300618 |
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IUPAC Name | [(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C45H69O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-44(46)51-41-43(42-52-54(48,49)50)53-45(47)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,22,24,26-29,32,34,43H,3-4,9-10,15-16,21,23,25,30-31,33,35-42H2,1-2H3,(H2,48,49,50)/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,24-22-,28-26-,29-27-,34-32-/t43-/m1/s1 |
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InChI Key | YOYYKWRNAISHRM-WADDUGSZSA-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 | Not Available |
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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(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0016165)
- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0016166)
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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(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 6178.7 | Standard polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 4815.9 | Standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5520.6 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC | 5612.8 | Semi standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC | 4918.5 | Standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC | 5019.6 | Standard polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC | 5826.1 | Semi standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC | 5042.2 | Standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC | 5066.4 | 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(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-0fri-1169803700-00c5a5c116c7750dd08e | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-029j-3298415200-5b277c7b9e7c9eaf328d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-0079-1169023000-568b2f8db543ab284c24 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Negative-QTOF | splash10-02di-3019300200-656f5929cebbdc31a58a | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Negative-QTOF | splash10-004i-9015000000-cef819a3ca8f603fe6be | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Negative-QTOF | splash10-004i-9000000000-f19992d5dc418e18671d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Negative-QTOF | splash10-014i-0000000900-eb1bbeaefd7ffeeeb67f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Negative-QTOF | splash10-014i-0006900400-a29e38d30429891472a4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Negative-QTOF | splash10-0fb9-0009300000-786636673d37045bc3a4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-0006-0000000900-5cb5bcf9f6e2469b48d1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-0006-0000009900-a6528423afd1982872fe | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-01p6-0000922400-a9bc26c81db5e36fdcbc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 10V, Positive-QTOF | splash10-0uxr-0000000900-d3101109335d3b77e242 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 20V, Positive-QTOF | splash10-01b9-0000005900-ef986f3fd893380b38fd | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) 40V, Positive-QTOF | splash10-00y0-0000906200-86ed52a3f1b4336609b8 | 2021-09-25 | Wishart Lab | View Spectrum |
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