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 04:44:58 UTC |
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Update Date | 2022-11-30 19:26:12 UTC |
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HMDB ID | HMDB0115452 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) |
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Description | PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of lignoceric acid at the C-1 position and one chain of docosahexaenoic 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)CCCCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C49H85O8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-27-29-31-33-35-37-39-41-43-48(50)55-45-47(46-56-58(52,53)54)57-49(51)44-42-40-38-36-34-32-30-28-25-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,25,28,32,34,38,40,47H,3-5,7,9-11,13,15-17,19,21-24,26-27,29-31,33,35-37,39,41-46H2,1-2H3,(H2,52,53,54)/b8-6-,14-12-,20-18-,28-25-,34-32-,40-38-/t47-/m1/s1 |
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Synonyms | Value | Source |
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1-lignoceroyl-2-docosahexaenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-lignoceroyl-2-docosahexaenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(24:0/22:6) | SMPDB, HMDB | PA(24:0/22:6n3) | SMPDB, HMDB | PA(24:0/22:6w3) | SMPDB, HMDB | PA(46:6) | SMPDB, HMDB | Phosphatidic acid(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidic acid(24:0/22:6) | SMPDB, HMDB | Phosphatidic acid(24:0/22:6n3) | SMPDB, HMDB | Phosphatidic acid(24:0/22:6w3) | SMPDB, HMDB | Phosphatidic acid(46:6) | SMPDB, HMDB | Phosphatidate(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidate(24:0/22:6) | SMPDB, HMDB | Phosphatidate(24:0/22:6n3) | SMPDB, HMDB | Phosphatidate(24:0/22:6w3) | SMPDB, HMDB | Phosphatidate(46:6) | SMPDB, HMDB | PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | SMPDB | [(2R)-2-[(4Z,7Z,10Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(tetracosanoyloxy)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)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(tetracosanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(tetracosanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)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/C49H85O8P/c1-3-5-7-9-11-13-15-17-19-21-23-24-26-27-29-31-33-35-37-39-41-43-48(50)55-45-47(46-56-58(52,53)54)57-49(51)44-42-40-38-36-34-32-30-28-25-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,25,28,32,34,38,40,47H,3-5,7,9-11,13,15-17,19,21-24,26-27,29-31,33,35-37,39,41-46H2,1-2H3,(H2,52,53,54)/b8-6-,14-12-,20-18-,28-25-,34-32-,40-38-/t47-/m1/s1 |
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InChI Key | FZMZTVPEWKDTDS-XMUBYKPVSA-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(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0) (PathBank: SMP0020618)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:1(9Z)) (PathBank: SMP0020619)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0020620)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0020621)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0020622)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:1(11Z)) (PathBank: SMP0020623)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0020624)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:1(13Z)) (PathBank: SMP0020625)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)) (PathBank: SMP0020626)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0020627)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0020628)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0020629)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:2(13Z,16Z)) (PathBank: SMP0020630)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0020631)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0020632)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0020633)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0020634)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0020635)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0020636)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0020637)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0020638)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)) (PathBank: SMP0037061)
- De Novo Triacylglycerol Biosynthesis TG(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0037062)
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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(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5770.2 | Standard polar | 33892256 | PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5285.7 | Standard non polar | 33892256 | PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5935.9 | 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(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0n30-1009330240-dff12bc261bd76009479 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0n2a-2129410110-c42ad415945305446ce0 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0r29-1149600200-21abd10d40ec9cd56839 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-00pj-3009020020-248ea36fff479bf80973 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-004j-9006000000-862fad66566edd9ae7a4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-9000000000-790f8a4ee1e43758339d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0a4i-0000000090-0e685013731ae519ef47 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0a4i-0000000990-02e5861b4432d3acd50f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0a4i-0000390340-8ec20a9098f5a28b9880 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0159-0000000090-cccdc31eb4cfc6496ed4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-001r-0000000590-780111831a7faf01e180 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-05n0-0000660930-501952541bb1e15c7bec | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-001i-0000000090-33920b3efdf52b79b888 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-0wq9-1109570060-c2a5c48b1fd96e1d25c7 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-016r-0009110000-4f6b27f6738c11aaae5b | 2021-09-24 | Wishart Lab | View Spectrum |
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