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 04:56:13 UTC |
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Update Date | 2022-11-30 19:26:14 UTC |
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HMDB ID | HMDB0115526 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) |
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Description | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 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(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of eicosadienoic 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)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C41H69O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,21,25,27,39H,3-5,7,9-10,15-16,20,22-24,26,28-38H2,1-2H3,(H2,44,45,46)/b8-6-,13-11-,14-12-,19-17-,21-18-,27-25-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-stearidonoyl-2-eicosadienoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-stearidonoyl-2-eicosadienoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:4/20:2) | SMPDB, HMDB | PA(18:4n3/20:2n6) | SMPDB, HMDB | PA(18:4w3/20:2w6) | SMPDB, HMDB | PA(38:6) | SMPDB, HMDB | Phosphatidic acid(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) | SMPDB, HMDB | Phosphatidic acid(18:4/20:2) | SMPDB, HMDB | Phosphatidic acid(18:4n3/20:2n6) | SMPDB, HMDB | Phosphatidic acid(18:4w3/20:2w6) | SMPDB, HMDB | Phosphatidic acid(38:6) | SMPDB, HMDB | Phosphatidate(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) | SMPDB, HMDB | Phosphatidate(18:4/20:2) | SMPDB, HMDB | Phosphatidate(18:4n3/20:2n6) | SMPDB, HMDB | Phosphatidate(18:4w3/20:2w6) | SMPDB, HMDB | Phosphatidate(38:6) | SMPDB, HMDB | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) | 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)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C41H69O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-19,21,25,27,39H,3-5,7,9-10,15-16,20,22-24,26,28-38H2,1-2H3,(H2,44,45,46)/b8-6-,13-11-,14-12-,19-17-,21-18-,27-25-/t39-/m1/s1 |
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InChI Key | UWYUAGTZXZYKAQ-NEQUQPNKSA-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(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0033391)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0033392)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0033393)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0033394)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0033395)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z)) (PathBank: SMP0067314)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0067315)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0067316)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0067317)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:0) (PathBank: SMP0067320)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z)) (PathBank: SMP0067321)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z)) (PathBank: SMP0067322)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0067323)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0067324)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:0) (PathBank: SMP0067327)
- De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z)) (PathBank: SMP0067328)
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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(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC | 5309.5 | Standard polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC | 4423.2 | Standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) | [H][C@@](COC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC | 5119.0 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 5148.5 | Semi standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 4540.0 | Standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 5364.0 | Standard polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 5126.7 | Semi standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 4506.8 | Standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),2TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 4684.1 | Standard polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 5363.9 | Semi standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 4654.0 | Standard non polar | 33892256 | PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC | 5366.9 | 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(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-074m-1192602400-e551f2a698eac34c1da3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-052e-2192201000-81bca7d8641452fb1723 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-00ls-1094002000-1eee3a812122a66784a5 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 10V, Negative-QTOF | splash10-056r-4092300200-7edaaaa762874667e7be | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 20V, Negative-QTOF | splash10-004i-9050000000-5f0345dcd75c83702e69 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9000000000-23c4569c13c5bc8bd49e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-0006-0000000900-70ab48513a971e9eb433 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-0008-0000009900-f1022aecfc549bf4876a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-00ku-0000902300-df73f1b040b90f9de53f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-0uk9-0000000900-a582fe7c9b18baf3a6f2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-00di-0000005900-af63e5be98da538ed84c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-022a-0000906200-ad837ec14178cc4b281d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 10V, Negative-QTOF | splash10-014i-0000000900-edfa899a8be3e750b15f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 20V, Negative-QTOF | splash10-092c-0033900400-2cc41f8c1b51507b747d | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)) 40V, Negative-QTOF | splash10-056r-1196600100-68c9923abc277dccc762 | 2021-09-25 | Wishart Lab | View Spectrum |
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Pathways | |
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