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 05:05:15 UTC |
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Update Date | 2022-11-30 19:26:15 UTC |
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HMDB ID | HMDB0115569 |
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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)/18:3(6Z,9Z,12Z)) |
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Description | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 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)/18:3(6Z,9Z,12Z)), in particular, consists of one chain of dihomo-gamma-linolenic acid at the C-1 position and one chain of gamma-linolenic 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)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C41H69O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,26,28,39H,3-10,15-16,20,24-25,27,29-38H2,1-2H3,(H2,44,45,46)/b13-11-,14-12-,19-17-,21-18-,23-22-,28-26-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-dihomo-gamma-linolenoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-dihomo-gamma-linolenoyl-2-gamma-linolenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:3/18:3) | SMPDB, HMDB | PA(20:3n6/18:3n6) | SMPDB, HMDB | PA(20:3w6/18:3w6) | SMPDB, HMDB | PA(38:6) | SMPDB, HMDB | Phosphatidic acid(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) | SMPDB, HMDB | Phosphatidic acid(20:3/18:3) | SMPDB, HMDB | Phosphatidic acid(20:3n6/18:3n6) | SMPDB, HMDB | Phosphatidic acid(20:3w6/18:3w6) | SMPDB, HMDB | Phosphatidic acid(38:6) | SMPDB, HMDB | Phosphatidate(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) | SMPDB, HMDB | Phosphatidate(20:3/18:3) | SMPDB, HMDB | Phosphatidate(20:3n6/18:3n6) | SMPDB, HMDB | Phosphatidate(20:3w6/18:3w6) | SMPDB, HMDB | Phosphatidate(38:6) | SMPDB, HMDB | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) | SMPDB |
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Chemical Formula | C41H69O8P |
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Average Molecular Weight | 720.969 |
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Monoisotopic Molecular Weight | 720.47300618 |
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IUPAC Name | [(2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]-2-[(6Z,9Z,12Z)-octadeca-6,9,12-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)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C41H69O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-23,26,28,39H,3-10,15-16,20,24-25,27,29-38H2,1-2H3,(H2,44,45,46)/b13-11-,14-12-,19-17-,21-18-,23-22-,28-26-/t39-/m1/s1 |
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InChI Key | DIYSKRVLPLFAQN-SIXIQDSKSA-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)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0035043)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0035044)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0035045)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0035046)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0035047)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0035048)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z)) (PathBank: SMP0035049)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0035050)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0035051)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0035052)
- De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0035053)
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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(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) | [H][C@@](COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC | 5287.7 | Standard polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) | [H][C@@](COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC | 4402.7 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) | [H][C@@](COC(=O)CCCCCC\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC | 5116.8 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 5131.1 | Semi standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 4538.7 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 5323.5 | Standard polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 5111.5 | Semi standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 4505.4 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 4651.4 | Standard polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 5346.4 | Semi standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 4653.0 | Standard non polar | 33892256 | PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)),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)CCCC/C=C\C/C=C\C/C=C\CCCCC | 5329.0 | 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)/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF | splash10-022l-1192502400-a557c5cd7e7eca3a80a7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF | splash10-01p5-2192221100-6b81e9b4681a3db7dfa1 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF | splash10-03dj-1197034000-ccaad2f21c5ee6ea2e8d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 10V, Negative-QTOF | splash10-0a70-4094400300-95dd22798c04771497ef | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 20V, Negative-QTOF | splash10-004i-9032000000-c6f2c4033aff2b14aac4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 40V, Negative-QTOF | splash10-004i-9000000000-5caaf530c962b4721665 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF | splash10-0uk9-0000000900-a582fe7c9b18baf3a6f2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF | splash10-00di-0000005900-af63e5be98da538ed84c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF | splash10-00xu-0000906200-713397151d2ec962bb16 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 10V, Negative-QTOF | splash10-014i-0000000900-edfa899a8be3e750b15f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 20V, Negative-QTOF | splash10-07xx-0033900400-c0ff39b7852f01e83e78 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 40V, Negative-QTOF | splash10-0a6r-1169600100-62dfaa6eeaf81bd78e86 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF | splash10-0006-0000000900-70ab48513a971e9eb433 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF | splash10-0008-0000009900-f1022aecfc549bf4876a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:3(8Z,11Z,14Z)/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF | splash10-05np-0000902300-a20f5cfb3df60ed5679e | 2021-09-24 | Wishart Lab | View Spectrum |
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Pathways | |
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