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 04:36:22 UTC |
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Update Date | 2022-11-30 19:26:11 UTC |
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HMDB ID | HMDB0115400 |
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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)/24:1(15Z)) |
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Description | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(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(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)), in particular, consists of one chain of clupanodonic acid at the C-1 position and one chain of nervonic 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)CCCCCCCCCCCCC\C=C/CCCCCCCC InChI=1S/C49H85O8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-28-30-32-34-36-38-40-42-44-49(51)57-47(46-56-58(52,53)54)45-55-48(50)43-41-39-37-35-33-31-29-27-25-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,25,27,31,33,47H,3-5,7,9-11,13,15-16,21-24,26,28-30,32,34-46H2,1-2H3,(H2,52,53,54)/b8-6-,14-12-,19-17-,20-18-,27-25-,33-31-/t47-/m1/s1 |
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Synonyms | Value | Source |
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1-clupanodonoyl-2-nervonoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-clupanodonoyl-2-nervonoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:5/24:1) | SMPDB, HMDB | PA(22:5n3/24:1n9) | SMPDB, HMDB | PA(22:5w3/24:1w9) | SMPDB, HMDB | PA(46:6) | SMPDB, HMDB | Phosphatidic acid(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) | SMPDB, HMDB | Phosphatidic acid(22:5/24:1) | SMPDB, HMDB | Phosphatidic acid(22:5n3/24:1n9) | SMPDB, HMDB | Phosphatidic acid(22:5w3/24:1w9) | SMPDB, HMDB | Phosphatidic acid(46:6) | SMPDB, HMDB | Phosphatidate(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) | SMPDB, HMDB | Phosphatidate(22:5/24:1) | SMPDB, HMDB | Phosphatidate(22:5n3/24:1n9) | SMPDB, HMDB | Phosphatidate(22:5w3/24:1w9) | SMPDB, HMDB | Phosphatidate(46:6) | SMPDB, HMDB | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) | SMPDB | [(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoyloxy]-2-[(15Z)-tetracos-15-enoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C49H85O8P |
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Average Molecular Weight | 833.185 |
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Monoisotopic Molecular Weight | 832.598206695 |
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IUPAC Name | [(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-[(15Z)-tetracos-15-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-[(15Z)-tetracos-15-enoyloxy]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)CCCCCCCCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C49H85O8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-28-30-32-34-36-38-40-42-44-49(51)57-47(46-56-58(52,53)54)45-55-48(50)43-41-39-37-35-33-31-29-27-25-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,17-20,25,27,31,33,47H,3-5,7,9-11,13,15-16,21-24,26,28-30,32,34-46H2,1-2H3,(H2,52,53,54)/b8-6-,14-12-,19-17-,20-18-,27-25-,33-31-/t47-/m1/s1 |
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InChI Key | WQJDNLIVPDCSJJ-JZQNTXITSA-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)/24:1(15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0026107)
- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0026108)
- De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z)) (PathBank: SMP0068393)
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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)/24:1(15Z)) | [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)CCCCCCCCCCCCC\C=C/CCCCCCCC | 5723.6 | Standard polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) | [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)CCCCCCCCCCCCC\C=C/CCCCCCCC | 5260.5 | Standard non polar | 33892256 | PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) | [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)CCCCCCCCCCCCC\C=C/CCCCCCCC | 5926.3 | Semi standard non 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)/24:1(15Z)) 10V, Positive-QTOF | splash10-02u1-1009320140-8134c196a911cc88e99e | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 20V, Positive-QTOF | splash10-00kb-1119210100-507281358ff2883c1555 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 40V, Positive-QTOF | splash10-00ds-0029100100-eab659165787af6a2a73 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 10V, Negative-QTOF | splash10-02e9-3009200020-050d9fe9b1086d719d78 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 20V, Negative-QTOF | splash10-004i-9005000000-de6ae52e9497b72d4135 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 40V, Negative-QTOF | splash10-004i-9000000000-1b450e0be6fd0d9df2f7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 10V, Positive-QTOF | splash10-0a4i-0000000090-0e685013731ae519ef47 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 20V, Positive-QTOF | splash10-0a4i-0000000990-02e5861b4432d3acd50f | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 40V, Positive-QTOF | splash10-0a4i-0000390340-8a3192143b544ca83f9c | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 10V, Negative-QTOF | splash10-001i-0000000090-33920b3efdf52b79b888 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 20V, Negative-QTOF | splash10-0159-1109750060-de9bbf0f62da64a25d32 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 40V, Negative-QTOF | splash10-00or-0009110000-d681f754fdcf9a144a4d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 10V, Positive-QTOF | splash10-0159-0000000090-cccdc31eb4cfc6496ed4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 20V, Positive-QTOF | splash10-001r-0000000590-780111831a7faf01e180 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) 40V, Positive-QTOF | splash10-0fri-0000660930-2fbc6a43c1432244a32e | 2021-09-24 | Wishart Lab | View Spectrum |
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