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 04:22:41 UTC |
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Update Date | 2022-11-30 19:26:09 UTC |
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HMDB ID | HMDB0115326 |
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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)/16:0) |
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Description | PA(22:4(7Z,10Z,13Z,16Z)/16:0) 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)/16:0), in particular, consists of one chain of adrenic acid at the C-1 position and one chain of palmitic 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)CCCCCCCCCCCCCCC InChI=1S/C41H73O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h11,13,17-18,20-21,24-25,39H,3-10,12,14-16,19,22-23,26-38H2,1-2H3,(H2,44,45,46)/b13-11-,18-17-,21-20-,25-24-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-adrenoyl-2-palmitoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-adrenoyl-2-palmitoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:4/16:0) | SMPDB, HMDB | PA(22:4n6/16:0) | SMPDB, HMDB | PA(22:4w6/16:0) | SMPDB, HMDB | PA(38:4) | SMPDB, HMDB | Phosphatidic acid(22:4(7Z,10Z,13Z,16Z)/16:0) | SMPDB, HMDB | Phosphatidic acid(22:4/16:0) | SMPDB, HMDB | Phosphatidic acid(22:4n6/16:0) | SMPDB, HMDB | Phosphatidic acid(22:4w6/16:0) | SMPDB, HMDB | Phosphatidic acid(38:4) | SMPDB, HMDB | Phosphatidate(22:4(7Z,10Z,13Z,16Z)/16:0) | SMPDB, HMDB | Phosphatidate(22:4/16:0) | SMPDB, HMDB | Phosphatidate(22:4n6/16:0) | SMPDB, HMDB | Phosphatidate(22:4w6/16:0) | SMPDB, HMDB | Phosphatidate(38:4) | SMPDB, HMDB | PA(22:4(7Z,10Z,13Z,16Z)/16:0) | SMPDB |
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Chemical Formula | C41H73O8P |
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Average Molecular Weight | 725.001 |
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Monoisotopic Molecular Weight | 724.504306309 |
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IUPAC Name | [(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-(hexadecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-(hexadecanoyloxy)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)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C41H73O8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h11,13,17-18,20-21,24-25,39H,3-10,12,14-16,19,22-23,26-38H2,1-2H3,(H2,44,45,46)/b13-11-,18-17-,21-20-,25-24-/t39-/m1/s1 |
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InChI Key | LDYXBNUGLKWLSN-FUGBMDIYSA-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)/16:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0025235)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0025236)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0025237)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0025238)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0025239)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0025240)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025241)
- De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025242)
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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)/16:0),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)CCCCCCCCCCCCCCC | 5135.2 | Semi standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 4552.7 | Standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 5785.6 | Standard polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 5099.3 | Semi standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 4522.0 | Standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 5048.8 | Standard polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 5354.3 | Semi standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 4651.9 | Standard non polar | 33892256 | PA(22:4(7Z,10Z,13Z,16Z)/16:0),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)CCCCCCCCCCCCCCC | 5762.9 | 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(22:4(7Z,10Z,13Z,16Z)/16:0) 10V, Positive-QTOF | splash10-0699-1289403600-6ceb5aa40d750ba9a3dc | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 20V, Positive-QTOF | splash10-01bj-2296202000-f0f28d4f90e8175e014a | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 40V, Positive-QTOF | splash10-007a-1497004000-ed3666fb05fb689b6968 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 10V, Negative-QTOF | splash10-071i-4039300300-31f065e08fb2700fb1d9 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 20V, Negative-QTOF | splash10-004i-9014000000-4d5fc12dc242ac9e0b8b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 40V, Negative-QTOF | splash10-004i-9000000000-83fe3e27af4eb4351e87 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 10V, Positive-QTOF | splash10-0002-0000000900-c7217cc8b4fecc83cb81 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 20V, Positive-QTOF | splash10-0002-0000009900-9aeab714e87e1529316e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 40V, Positive-QTOF | splash10-00ke-0000922400-762311ec1fe61807d5b1 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 10V, Negative-QTOF | splash10-00di-0000000900-503da6078c6f482f0a70 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 20V, Negative-QTOF | splash10-06l3-1149900600-b804f67a8895fd287351 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 40V, Negative-QTOF | splash10-053r-1159300100-3468b7563bb5789d6099 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 10V, Positive-QTOF | splash10-0a6r-0000000900-f25618a4673f1c76e672 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 20V, Positive-QTOF | splash10-004i-0000005900-4871ac345f15ca0d32cd | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:4(7Z,10Z,13Z,16Z)/16:0) 40V, Positive-QTOF | splash10-00ou-0006609300-1540632c113ec6bcef87 | 2021-09-24 | Wishart Lab | View Spectrum |
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Pathways | |
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