Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2010-05-13 16:10:05 UTC |
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Update Date | 2022-11-30 19:04:13 UTC |
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HMDB ID | HMDB0013560 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) |
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Description | PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols 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. PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the docosapentaenoic acid moiety is derived from fish oils. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. |
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Structure | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C46H78O13P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(49)59-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)41-55-45(48)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,43-44,47H,3-4,6,8-10,15-16,20,24-25,27,29-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t43-,44+/m0/s1 |
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Synonyms | Value | Source |
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PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | Lipid Annotator | 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | Lipid Annotator, HMDB | 1-linoleoyl-2-docosapentaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | PGP(18:2/22:5) | Lipid Annotator, HMDB | 1-(9Z,12Z-octadecadienoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | PGP(40:7) | Lipid Annotator, HMDB | PGP(18:2n6/22:5n3) | HMDB | PGP(18:2W6/22:5W3) | HMDB |
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Chemical Formula | C46H78O13P2 |
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Average Molecular Weight | 901.0512 |
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Monoisotopic Molecular Weight | 900.491765606 |
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IUPAC Name | [(2S)-3-({[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid |
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Traditional Name | (2S)-3-{[(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@]([H])(COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C46H78O13P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(49)59-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)41-55-45(48)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,43-44,47H,3-4,6,8-10,15-16,20,24-25,27,29-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-/t43-,44+/m0/s1 |
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InChI Key | XEPYCCSZJZTWML-GQEJPCSQSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety 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 | Glycerophosphoglycerophosphates |
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Direct Parent | Phosphatidylglycerophosphates |
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Alternative Parents | |
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Substituents | - Diacylglycerophosphoglycerophosphate
- Sn-glycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- 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 | |
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Disposition | |
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Process | Naturally occurring processBiological processChemical reactionBiochemical pathway- Cardiolipin Biosynthesis (HMDB: HMDB0013560)
Metabolic pathway- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029509)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029510)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0029511)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029512)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029513)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029514)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0029515)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (PathBank: SMP0029516)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0029517)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0029518)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0029519)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0029520)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029521)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029522)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029523)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029524)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029525)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0029526)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0029527)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0029528)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0029529)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029530)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029531)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029532)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029533)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029534)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029535)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029536)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029537)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029538)
Biochemical processCellular process |
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Role | |
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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 IndicesNot Available |
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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 - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0irr-1396045163-a3262d2bede11288bcea | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-03di-3495023330-c7e62b38bfa6fef37ea1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0a4i-9377104410-e7bd560ca0e7e8552b7c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-004i-4092020120-0011c23414d520a92ad4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-004i-9050000000-e4d9a9cbc7a15033ce36 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-9000000000-141586024a72ed05961f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-0udj-3100009186-c7dcda7daff084f26245 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-0kbb-2200004930-3a8cf06eb7efc0ce204c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-00sr-1302951300-e5a11c8bce12204607fb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-0002-0000000090-fafeac6106db310d346a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-002b-9052014160-236aafc60930f0ac5025 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-8092000020-50349321ac4dcda5d4fd | 2021-09-22 | Wishart Lab | View Spectrum |
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Pathways | |
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