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 03:22:39 UTC |
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Update Date | 2022-11-30 19:26:01 UTC |
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HMDB ID | HMDB0115025 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:3(9Z,12Z,15Z)/24:0) |
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Description | PA(18:3(9Z,12Z,15Z)/24:0) 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(18:3(9Z,12Z,15Z)/24:0), in particular, consists of one chain of alpha-linolenic acid at the C-1 position and one chain of lignoceric 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/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC InChI=1S/C45H83O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-26-28-30-32-34-36-38-40-45(47)53-43(42-52-54(48,49)50)41-51-44(46)39-37-35-33-31-29-27-25-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,25,43H,3-5,7,9-11,13,15-17,19-24,26-42H2,1-2H3,(H2,48,49,50)/b8-6-,14-12-,25-18-/t43-/m1/s1 |
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Synonyms | Value | Source |
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1-alpha-linolenoyl-2-lignoceroyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-alpha-linolenoyl-2-lignoceroyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:3/24:0) | SMPDB, HMDB | PA(18:3n3/24:0) | SMPDB, HMDB | PA(18:3w3/24:0) | SMPDB, HMDB | PA(42:3) | SMPDB, HMDB | Phosphatidic acid(18:3(9Z,12Z,15Z)/24:0) | SMPDB, HMDB | Phosphatidic acid(18:3/24:0) | SMPDB, HMDB | Phosphatidic acid(18:3n3/24:0) | SMPDB, HMDB | Phosphatidic acid(18:3w3/24:0) | SMPDB, HMDB | Phosphatidic acid(42:3) | SMPDB, HMDB | Phosphatidate(18:3(9Z,12Z,15Z)/24:0) | SMPDB, HMDB | Phosphatidate(18:3/24:0) | SMPDB, HMDB | Phosphatidate(18:3n3/24:0) | SMPDB, HMDB | Phosphatidate(18:3w3/24:0) | SMPDB, HMDB | Phosphatidate(42:3) | SMPDB, HMDB | PA(18:3(9Z,12Z,15Z)/24:0) | SMPDB | [(2R)-3-[(9Z,12Z,15Z)-Octadeca-9,12,15-trienoyloxy]-2-(tetracosanoyloxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C45H83O8P |
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Average Molecular Weight | 783.125 |
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Monoisotopic Molecular Weight | 782.582556631 |
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IUPAC Name | [(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-(tetracosanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-(tetracosanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C45H83O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-26-28-30-32-34-36-38-40-45(47)53-43(42-52-54(48,49)50)41-51-44(46)39-37-35-33-31-29-27-25-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,25,43H,3-5,7,9-11,13,15-17,19-24,26-42H2,1-2H3,(H2,48,49,50)/b8-6-,14-12-,25-18-/t43-/m1/s1 |
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InChI Key | FGWXOBIPJMJISC-NYAZRSJZSA-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 | Not Available |
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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(18:3(9Z,12Z,15Z)/24:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0025657)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0025658)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0025659)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0025660)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025661)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025662)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:0) (PathBank: SMP0067260)
- De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:1(15Z)) (PathBank: SMP0067261)
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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(18:3(9Z,12Z,15Z)/24:0),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5574.1 | Semi standard non polar | 33892256 | PA(18:3(9Z,12Z,15Z)/24:0),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4883.9 | Standard non polar | 33892256 | PA(18:3(9Z,12Z,15Z)/24:0),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 6266.4 | Standard polar | 33892256 | PA(18:3(9Z,12Z,15Z)/24:0),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 5790.3 | Semi standard non polar | 33892256 | PA(18:3(9Z,12Z,15Z)/24:0),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 4964.0 | Standard non polar | 33892256 | PA(18:3(9Z,12Z,15Z)/24:0),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCCCC | 6240.0 | 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(18:3(9Z,12Z,15Z)/24:0) 10V, Positive-QTOF | splash10-0i0r-1169532700-e03704372938c41e3c70 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 20V, Positive-QTOF | splash10-0n2a-2149211100-547c64fe51a91f964f1e | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 40V, Positive-QTOF | splash10-0n39-1049101100-d4e8fa5a58bcc137bac2 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 10V, Negative-QTOF | splash10-057i-4093300300-66dfac119e0583aa0db8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 20V, Negative-QTOF | splash10-004i-9051000000-662eb4902dc75d0eba19 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 40V, Negative-QTOF | splash10-004i-9000000000-b096bd3983d70354246b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 10V, Negative-QTOF | splash10-001i-0000000900-3cb8fce685f119c3a9c1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 20V, Negative-QTOF | splash10-0hji-1155960700-e58becd57878bdd9ee47 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 40V, Negative-QTOF | splash10-00or-1196330100-91ac78e3d8b18a1b14c3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 10V, Positive-QTOF | splash10-0a4i-0000000090-e636bd05e97a8e8a7139 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 20V, Positive-QTOF | splash10-0a4i-0000000990-3999ab60877472ab4e30 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 40V, Positive-QTOF | splash10-0a4i-0000990460-e773b5d7837e780a54e9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 10V, Positive-QTOF | splash10-0159-0000000900-4eea4050b5b696d7f9c3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 20V, Positive-QTOF | splash10-001r-0000005900-1916dfe5f2287fa587d1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:3(9Z,12Z,15Z)/24:0) 40V, Positive-QTOF | splash10-05n0-0000669300-c105ab41a34e3bb01999 | 2021-09-25 | Wishart Lab | View Spectrum |
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Pathways | |
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