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 04:53:58 UTC |
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Update Date | 2022-11-30 19:26:14 UTC |
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HMDB ID | HMDB0115512 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(16:1(9Z)/20:2(11Z,14Z)) |
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Description | PA(16:1(9Z)/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(16:1(9Z)/20:2(11Z,14Z)), in particular, consists of one chain of palmitoleic 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)CCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C39H71O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(41)47-37(36-46-48(42,43)44)35-45-38(40)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,37H,3-10,12,15,19-36H2,1-2H3,(H2,42,43,44)/b13-11-,16-14-,18-17-/t37-/m1/s1 |
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Synonyms | Value | Source |
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1-palmitoleoyl-2-eicosadienoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-palmitoleoyl-2-eicosadienoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(16:1/20:2) | SMPDB, HMDB | PA(16:1n7/20:2n6) | SMPDB, HMDB | PA(16:1w7/20:2w6) | SMPDB, HMDB | PA(36:3) | SMPDB, HMDB | Phosphatidic acid(16:1(9Z)/20:2(11Z,14Z)) | SMPDB, HMDB | Phosphatidic acid(16:1/20:2) | SMPDB, HMDB | Phosphatidic acid(16:1n7/20:2n6) | SMPDB, HMDB | Phosphatidic acid(16:1w7/20:2w6) | SMPDB, HMDB | Phosphatidic acid(36:3) | SMPDB, HMDB | Phosphatidate(16:1(9Z)/20:2(11Z,14Z)) | SMPDB, HMDB | Phosphatidate(16:1/20:2) | SMPDB, HMDB | Phosphatidate(16:1n7/20:2n6) | SMPDB, HMDB | Phosphatidate(16:1w7/20:2w6) | SMPDB, HMDB | Phosphatidate(36:3) | SMPDB, HMDB | PA(16:1(9Z)/20:2(11Z,14Z)) | 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)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C39H71O8P/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(41)47-37(36-46-48(42,43)44)35-45-38(40)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,37H,3-10,12,15,19-36H2,1-2H3,(H2,42,43,44)/b13-11-,16-14-,18-17-/t37-/m1/s1 |
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InChI Key | PZDXLPCRKVXCRO-DFCPKGTFSA-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(16:1(9Z)/20:2(11Z,14Z)/16:1(9Z)) (PathBank: SMP0032865)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/18:1(11Z)) (PathBank: SMP0032866)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/18:1(9Z)) (PathBank: SMP0032867)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0032868)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0032869)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0032870)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0032871)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:1(11Z)) (PathBank: SMP0032872)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z)) (PathBank: SMP0032873)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0032874)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0032875)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0032876)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0032877)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0032878)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:1(13Z)) (PathBank: SMP0032879)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z)) (PathBank: SMP0032880)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0032881)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0032882)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0032883)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0032884)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:1(15Z)) (PathBank: SMP0032885)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0) (PathBank: SMP0065683)
- De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:0) (PathBank: SMP0065690)
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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(16:1(9Z)/20:2(11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C | 4937.7 | Semi standard non polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C | 4355.6 | Standard non polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C | 5586.1 | Standard polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4895.6 | Semi standard non polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4321.9 | Standard non polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4828.5 | Standard polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5168.0 | Semi standard non polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4452.0 | Standard non polar | 33892256 | PA(16:1(9Z)/20:2(11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCC/C=C\CCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5570.1 | 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(16:1(9Z)/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-0005-1194206000-d57672ea5620555a999f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-0005-2292112000-106f007a1a0fbe03cda3 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-01ot-1293021000-9f452d9778f25610ec77 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 10V, Negative-QTOF | splash10-0k9j-4093202000-bb5ae8713f6ead99200b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 20V, Negative-QTOF | splash10-004i-9050000000-ac0aef609b91080f20fb | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9000000000-da3488d48ebe5a7e4a99 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-00di-0000000900-33eb9f3dea5e904ac027 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-00di-0000009900-0d1e697a527f0c6105be | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-02mi-0000902300-782a3ff1ffd344be16a6 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-001j-0000009000-9f471deda5cfdf006143 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-0f6t-0000009000-be2ae51398b948063c28 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-0udm-0004409000-2a256af5021e2d53115b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 10V, Negative-QTOF | splash10-0002-0000009000-05f0150958446fe6e469 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 20V, Negative-QTOF | splash10-0k9n-0039505000-36d79dc50d13ffac9cd5 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:1(9Z)/20:2(11Z,14Z)) 40V, Negative-QTOF | splash10-0zfr-1197401000-8d436f3185dcda4198aa | 2021-09-23 | Wishart Lab | View Spectrum |
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