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 05:03:35 UTC |
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Update Date | 2022-11-30 19:26:15 UTC |
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HMDB ID | HMDB0115564 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:3(8Z,11Z,14Z)/16:0) |
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Description | PA(20:3(8Z,11Z,14Z)/16:0) 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(20:3(8Z,11Z,14Z)/16:0), in particular, consists of one chain of dihomo-gamma-linolenic acid at the C-1 position and one chain of palmitic 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)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C39H71O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,37H,3-10,12,14-16,19,21,23-36H2,1-2H3,(H2,42,43,44)/b13-11-,18-17-,22-20-/t37-/m1/s1 |
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Synonyms | Value | Source |
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1-dihomo-gamma-linolenoyl-2-palmitoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-dihomo-gamma-linolenoyl-2-palmitoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:3/16:0) | SMPDB, HMDB | PA(20:3n6/16:0) | SMPDB, HMDB | PA(20:3w6/16:0) | SMPDB, HMDB | PA(36:3) | SMPDB, HMDB | Phosphatidic acid(20:3(8Z,11Z,14Z)/16:0) | SMPDB, HMDB | Phosphatidic acid(20:3/16:0) | SMPDB, HMDB | Phosphatidic acid(20:3n6/16:0) | SMPDB, HMDB | Phosphatidic acid(20:3w6/16:0) | SMPDB, HMDB | Phosphatidic acid(36:3) | SMPDB, HMDB | Phosphatidate(20:3(8Z,11Z,14Z)/16:0) | SMPDB, HMDB | Phosphatidate(20:3/16:0) | SMPDB, HMDB | Phosphatidate(20:3n6/16:0) | SMPDB, HMDB | Phosphatidate(20:3w6/16:0) | SMPDB, HMDB | Phosphatidate(36:3) | SMPDB, HMDB | PA(20:3(8Z,11Z,14Z)/16:0) | SMPDB |
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Chemical Formula | C39H71O8P |
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Average Molecular Weight | 698.963 |
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Monoisotopic Molecular Weight | 698.488656244 |
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IUPAC Name | [(2R)-2-(hexadecanoyloxy)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-(hexadecanoyloxy)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C39H71O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-21-16-14-12-10-8-6-4-2/h11,13,17-18,20,22,37H,3-10,12,14-16,19,21,23-36H2,1-2H3,(H2,42,43,44)/b13-11-,18-17-,22-20-/t37-/m1/s1 |
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InChI Key | WKBCBYXYEJTYBY-QNKWBPIESA-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(20:3(8Z,11Z,14Z)/16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0034977)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0034978)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0034979)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0034980)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0034981)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0034982)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/22:2(13Z,16Z)) (PathBank: SMP0034983)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0034984)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0034985)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034986)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034987)
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(20:3(8Z,11Z,14Z)/16:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4929.5 | Semi standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4392.6 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5711.8 | Standard polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4899.1 | Semi standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4364.0 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4986.8 | Standard polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5155.7 | Semi standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 4488.6 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/16:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCC | 5689.1 | 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(20:3(8Z,11Z,14Z)/16:0) 10V, Positive-QTOF | splash10-000m-1193306000-4a6e5c9e7095fdbc8565 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 20V, Positive-QTOF | splash10-000b-2292102000-df7f95249c6e6ed24002 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 40V, Positive-QTOF | splash10-01ot-1495022000-b499ee8662ebbeaf6670 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 10V, Negative-QTOF | splash10-0a4r-5095303000-8a7a955c8425ee65e48e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 20V, Negative-QTOF | splash10-004i-9033000000-f87889b0045f21534e6e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 40V, Negative-QTOF | splash10-004i-9000000000-27bfd71ad63b6d44311d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 10V, Positive-QTOF | splash10-001j-0000009000-9f471deda5cfdf006143 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 20V, Positive-QTOF | splash10-0f6t-0000009000-be2ae51398b948063c28 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 40V, Positive-QTOF | splash10-0f6x-0004409000-8634fbb2f798acff2a25 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 10V, Negative-QTOF | splash10-0002-0000009000-05f0150958446fe6e469 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 20V, Negative-QTOF | splash10-0a4m-1149906000-a8ef8310cee6b4594eac | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 40V, Negative-QTOF | splash10-0a4i-1159301000-c03180613bbda5a26119 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 10V, Positive-QTOF | splash10-00di-0000000900-33eb9f3dea5e904ac027 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 20V, Positive-QTOF | splash10-00di-0000009900-0d1e697a527f0c6105be | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/16:0) 40V, Positive-QTOF | splash10-01c0-0000902300-2a78d51a0d4882943a64 | 2021-09-22 | Wishart Lab | View Spectrum |
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Pathways | |
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