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 04:31:04 UTC |
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Update Date | 2022-11-30 19:26:10 UTC |
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HMDB ID | HMDB0115368 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) |
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Description | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 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(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)), in particular, consists of one chain of osbond acid at the C-1 position and one chain of erucic 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)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC InChI=1S/C47H81O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(48)53-43-45(44-54-56(50,51)52)55-47(49)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,23,25,29,31,35,37,45H,3-10,12,14-16,21-22,24,26-28,30,32-34,36,38-44H2,1-2H3,(H2,50,51,52)/b13-11-,19-17-,20-18-,25-23-,31-29-,37-35-/t45-/m1/s1 |
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Synonyms | Value | Source |
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1-osbondoyl-2-erucoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-osbondoyl-2-erucoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:5/22:1) | SMPDB, HMDB | PA(22:5n6/22:1n9) | SMPDB, HMDB | PA(22:5w6/22:1w9) | SMPDB, HMDB | PA(44:6) | SMPDB, HMDB | Phosphatidic acid(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) | SMPDB, HMDB | Phosphatidic acid(22:5/22:1) | SMPDB, HMDB | Phosphatidic acid(22:5n6/22:1n9) | SMPDB, HMDB | Phosphatidic acid(22:5w6/22:1w9) | SMPDB, HMDB | Phosphatidic acid(44:6) | SMPDB, HMDB | Phosphatidate(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) | SMPDB, HMDB | Phosphatidate(22:5/22:1) | SMPDB, HMDB | Phosphatidate(22:5n6/22:1n9) | SMPDB, HMDB | Phosphatidate(22:5w6/22:1w9) | SMPDB, HMDB | Phosphatidate(44:6) | SMPDB, HMDB | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) | SMPDB | [(2R)-2-[(13Z)-Docos-13-enoyloxy]-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C47H81O8P |
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Average Molecular Weight | 805.131 |
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Monoisotopic Molecular Weight | 804.566906566 |
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IUPAC Name | [(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC |
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InChI Identifier | InChI=1S/C47H81O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-46(48)53-43-45(44-54-56(50,51)52)55-47(49)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,23,25,29,31,35,37,45H,3-10,12,14-16,21-22,24,26-28,30,32-34,36,38-44H2,1-2H3,(H2,50,51,52)/b13-11-,19-17-,20-18-,25-23-,31-29-,37-35-/t45-/m1/s1 |
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InChI Key | OGBVNEMIJXSQKJ-CNWUXYNKSA-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(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0025527)
- De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0025528)
- De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0025529)
- De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0025530)
- De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0025531)
- De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025532)
- De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0025533)
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) | [H][C@@](COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC | 5595.7 | Standard polar | 33892256 | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) | [H][C@@](COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC | 5008.7 | Standard non polar | 33892256 | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) | [H][C@@](COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC | 5721.8 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCC/C=C\CCCCCCCC | 5755.7 | Semi standard non polar | 33892256 | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCC/C=C\CCCCCCCC | 5022.0 | Standard non polar | 33892256 | PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCC/C=C\CCCCCCCC | 5840.5 | 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(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 10V, Positive-QTOF | splash10-0cdr-1119800540-b32f9a1d1f5e1d244bff | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 20V, Positive-QTOF | splash10-044j-3249401400-62d3d5609ff2823c15a9 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 40V, Positive-QTOF | splash10-00dr-1149002200-0c25354243a501aa3f79 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 10V, Negative-QTOF | splash10-01t9-3009300020-8f6afa493fe5354b4c78 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 20V, Negative-QTOF | splash10-004i-9005000000-ebbc47c89bd26d3375ea | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 40V, Negative-QTOF | splash10-004i-9000000000-90627c2d4cc653180abd | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 10V, Positive-QTOF | splash10-052r-0000000950-d4ba03b39ce640d97e39 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 20V, Positive-QTOF | splash10-0a4i-0000000790-c4f48869bed3af8d5d23 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 40V, Positive-QTOF | splash10-0ar0-0000900710-583c48ce2f5832f267b0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 10V, Positive-QTOF | splash10-004i-0000000090-a3eceee2b127662d7e34 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 20V, Positive-QTOF | splash10-004i-0000000990-bfc2305264a1beb9b139 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 40V, Positive-QTOF | splash10-0571-0000960350-e9a3b0f17781abf302a8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 10V, Negative-QTOF | splash10-0udi-0000000090-adfb84f3359d1bb0bfe2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 20V, Negative-QTOF | splash10-0v70-0006900040-8ca7c02620e968196b70 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:5(4Z,7Z,10Z,13Z,16Z)/22:1(13Z)) 40V, Negative-QTOF | splash10-004r-0009300000-c964ff31b6839c9a58c8 | 2021-09-24 | Wishart Lab | View Spectrum |
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Pathways | |
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