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 04:22:17 UTC |
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Update Date | 2022-11-30 19:26:09 UTC |
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HMDB ID | HMDB0115325 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:4(7Z,10Z,13Z,16Z)/15:0) |
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Description | PA(22:4(7Z,10Z,13Z,16Z)/15:0) 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(22:4(7Z,10Z,13Z,16Z)/15:0), in particular, consists of one chain of adrenic acid at the C-1 position and one chain of pentadecanoic 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)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCC InChI=1S/C40H71O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-26-28-30-32-34-39(41)46-36-38(37-47-49(43,44)45)48-40(42)35-33-31-29-27-24-16-14-12-10-8-6-4-2/h11,13,17-18,20-21,23,25,38H,3-10,12,14-16,19,22,24,26-37H2,1-2H3,(H2,43,44,45)/b13-11-,18-17-,21-20-,25-23-/t38-/m1/s1 |
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Synonyms | Value | Source |
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1-adrenoyl-2-pentadecanoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-adrenoyl-2-pentadecanoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:4/15:0) | SMPDB, HMDB | PA(22:4n6/15:0) | SMPDB, HMDB | PA(22:4w6/15:0) | SMPDB, HMDB | PA(37:4) | SMPDB, HMDB | Phosphatidic acid(22:4(7Z,10Z,13Z,16Z)/15:0) | SMPDB, HMDB | Phosphatidic acid(22:4/15:0) | SMPDB, HMDB | Phosphatidic acid(22:4n6/15:0) | SMPDB, HMDB | Phosphatidic acid(22:4w6/15:0) | SMPDB, HMDB | Phosphatidic acid(37:4) | SMPDB, HMDB | Phosphatidate(22:4(7Z,10Z,13Z,16Z)/15:0) | SMPDB, HMDB | Phosphatidate(22:4/15:0) | SMPDB, HMDB | Phosphatidate(22:4n6/15:0) | SMPDB, HMDB | Phosphatidate(22:4w6/15:0) | SMPDB, HMDB | Phosphatidate(37:4) | SMPDB, HMDB | PA(22:4(7Z,10Z,13Z,16Z)/15:0) | SMPDB |
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Chemical Formula | C40H71O8P |
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Average Molecular Weight | 710.974 |
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Monoisotopic Molecular Weight | 710.488656244 |
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IUPAC Name | [(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-(pentadecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-(pentadecanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C40H71O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-26-28-30-32-34-39(41)46-36-38(37-47-49(43,44)45)48-40(42)35-33-31-29-27-24-16-14-12-10-8-6-4-2/h11,13,17-18,20-21,23,25,38H,3-10,12,14-16,19,22,24,26-37H2,1-2H3,(H2,43,44,45)/b13-11-,18-17-,21-20-,25-23-/t38-/m1/s1 |
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InChI Key | FZQMNEILCGEUNP-UXNHJCPVSA-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(22:4(7Z,10Z,13Z,16Z)/15:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0025227)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0025228)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0025229)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0025230)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0025231)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0025232)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025233)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025234)
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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(22:4(7Z,10Z,13Z,16Z)/15:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCC | 5033.3 | Semi standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCC | 4470.6 | Standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCC | 5699.5 | Standard polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCC | 4998.3 | Semi standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCC | 4441.2 | Standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCC | 4964.9 | Standard polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCC | 5252.0 | Semi standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCC | 4572.8 | Standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/15:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCC | 5678.2 | 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(22:4(7Z,10Z,13Z,16Z)/15:0) 10V, Positive-QTOF | splash10-02vl-1279405400-f594ccbc06f238c50d4b | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 20V, Positive-QTOF | splash10-01dj-3597204000-8dd77996b7291d99d975 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 40V, Positive-QTOF | splash10-0080-1779014000-016e3724975ad341c0c6 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 10V, Negative-QTOF | splash10-06uu-4039200200-357fbc00053538be26e0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 20V, Negative-QTOF | splash10-004i-9014000000-2ef418ce7dcb7fbb14a1 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 40V, Negative-QTOF | splash10-004i-9000000000-d898891388ac14dafbad | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 10V, Positive-QTOF | splash10-01ox-0000009500-93318bc8559f4b9c4d6f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 20V, Positive-QTOF | splash10-03di-0000007900-b4ff6062c027a4e9f1bc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 40V, Positive-QTOF | splash10-0400-0005509100-7439c00f4d2413bb6518 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 10V, Negative-QTOF | splash10-0a4i-0000000900-60b106d24c24e780625c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 20V, Negative-QTOF | splash10-0bc3-1139600500-f476aa21017b6795f6d9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 40V, Negative-QTOF | splash10-001l-1149200100-17600f112b7ce075872e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 10V, Positive-QTOF | splash10-001i-0000000900-ae020c345ffc6e39b78f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 20V, Positive-QTOF | splash10-0020-0000009900-2517f8efeacf0e61f13e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/15:0) 40V, Positive-QTOF | splash10-0kv3-0000922400-291af3e1b2c2aedd3e00 | 2021-09-24 | Wishart Lab | View Spectrum |
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Pathways | |
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