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 04:57:37 UTC |
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Update Date | 2022-11-30 19:26:14 UTC |
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HMDB ID | HMDB0115533 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:2(11Z,14Z)/14:1(9Z)) |
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Description | PA(20:2(11Z,14Z)/14:1(9Z)) 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(20:2(11Z,14Z)/14:1(9Z)), in particular, consists of one chain of eicosadienoic acid at the C-1 position and one chain of myristoleic 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)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCC InChI=1S/C37H67O8P/c1-3-5-7-9-11-13-15-16-17-18-19-20-22-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-21-14-12-10-8-6-4-2/h10-13,16-17,35H,3-9,14-15,18-34H2,1-2H3,(H2,40,41,42)/b12-10-,13-11-,17-16-/t35-/m1/s1 |
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Synonyms | Value | Source |
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1-eicosadienoyl-2-myristoleoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-eicosadienoyl-2-myristoleoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:2/14:1) | SMPDB, HMDB | PA(20:2n6/14:1n5) | SMPDB, HMDB | PA(20:2w6/14:1w5) | SMPDB, HMDB | PA(34:3) | SMPDB, HMDB | Phosphatidic acid(20:2(11Z,14Z)/14:1(9Z)) | SMPDB, HMDB | Phosphatidic acid(20:2/14:1) | SMPDB, HMDB | Phosphatidic acid(20:2n6/14:1n5) | SMPDB, HMDB | Phosphatidic acid(20:2w6/14:1w5) | SMPDB, HMDB | Phosphatidic acid(34:3) | SMPDB, HMDB | Phosphatidate(20:2(11Z,14Z)/14:1(9Z)) | SMPDB, HMDB | Phosphatidate(20:2/14:1) | SMPDB, HMDB | Phosphatidate(20:2n6/14:1n5) | SMPDB, HMDB | Phosphatidate(20:2w6/14:1w5) | SMPDB, HMDB | Phosphatidate(34:3) | SMPDB, HMDB | PA(20:2(11Z,14Z)/14:1(9Z)) | SMPDB |
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Chemical Formula | C37H67O8P |
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Average Molecular Weight | 670.909 |
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Monoisotopic Molecular Weight | 670.457356115 |
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IUPAC Name | [(2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCC |
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InChI Identifier | InChI=1S/C37H67O8P/c1-3-5-7-9-11-13-15-16-17-18-19-20-22-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-21-14-12-10-8-6-4-2/h10-13,16-17,35H,3-9,14-15,18-34H2,1-2H3,(H2,40,41,42)/b12-10-,13-11-,17-16-/t35-/m1/s1 |
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InChI Key | WDBNVOFFDMJPRH-CTBOXKONSA-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(20:2(11Z,14Z)/14:1(9Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0034520)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0034521)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/20:2(11Z,14Z)) (PathBank: SMP0034522)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0034523)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0034524)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0034525)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0034526)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/22:2(13Z,16Z)) (PathBank: SMP0034527)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0034528)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0034529)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034530)
- De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0034531)
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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(20:2(11Z,14Z)/14:1(9Z)),1TMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 4728.7 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),1TMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 4191.0 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),1TMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C | 5414.5 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),2TMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4685.1 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),2TMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4160.9 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),2TMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4658.1 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),1TBDMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4954.2 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),1TBDMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4292.7 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),1TBDMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5399.3 | Standard polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),2TBDMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 5134.6 | Semi standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),2TBDMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4328.2 | Standard non polar | 33892256 | PA(20:2(11Z,14Z)/14:1(9Z)),2TBDMS,isomer #1 | CCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCC/C=C\C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4756.5 | 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(20:2(11Z,14Z)/14:1(9Z)) 10V, Positive-QTOF | splash10-074m-1294325000-1ceb9546c6187ce54622 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 20V, Positive-QTOF | splash10-0002-2493231000-c68fffcf5b658ddc146d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 40V, Positive-QTOF | splash10-014j-1596051000-70dcfe770a30b3c9e028 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 10V, Negative-QTOF | splash10-0570-5096303000-03974fe16c2d949653bb | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 20V, Negative-QTOF | splash10-004i-9033000000-2b966bc226c5ea3556d4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 40V, Negative-QTOF | splash10-004i-9000000000-4a1d887a0c9988dbdad3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 10V, Negative-QTOF | splash10-014i-0000009000-8465477f36ce6d978aa8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 20V, Negative-QTOF | splash10-07fu-1139605000-ac600105d49870537a17 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 40V, Negative-QTOF | splash10-056r-1149201000-938aab63e8be3494847d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 10V, Positive-QTOF | splash10-0006-0000009000-680ea39749ce57da07e7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 20V, Positive-QTOF | splash10-0008-0000099000-24d12db87a2f5ea02832 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 40V, Positive-QTOF | splash10-00ku-0003934000-3b5ed24465410a36194a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 10V, Positive-QTOF | splash10-0uk9-0000009000-4b00c8059dd5f287deb6 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 20V, Positive-QTOF | splash10-00di-0000059000-000f7a098a0436ba96d3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:2(11Z,14Z)/14:1(9Z)) 40V, Positive-QTOF | splash10-022a-0006693000-3016f840a1fe7cfdf14d | 2021-09-23 | Wishart Lab | View Spectrum |
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