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 03:11:49 UTC |
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Update Date | 2022-11-30 19:25:59 UTC |
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HMDB ID | HMDB0114958 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(18:2(9Z,12Z)/20:0) |
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Description | PA(18:2(9Z,12Z)/20:0) 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(18:2(9Z,12Z)/20:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of arachidic 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/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCC InChI=1S/C41H77O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h12,14,18,21,39H,3-11,13,15-17,19-20,22-38H2,1-2H3,(H2,44,45,46)/b14-12-,21-18-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-linoleoyl-2-arachidoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-linoleoyl-2-arachidoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:2/20:0) | SMPDB, HMDB | PA(18:2n6/20:0) | SMPDB, HMDB | PA(18:2w6/20:0) | SMPDB, HMDB | PA(38:2) | SMPDB, HMDB | Phosphatidic acid(18:2(9Z,12Z)/20:0) | SMPDB, HMDB | Phosphatidic acid(18:2/20:0) | SMPDB, HMDB | Phosphatidic acid(18:2n6/20:0) | SMPDB, HMDB | Phosphatidic acid(18:2w6/20:0) | SMPDB, HMDB | Phosphatidic acid(38:2) | SMPDB, HMDB | Phosphatidate(18:2(9Z,12Z)/20:0) | SMPDB, HMDB | Phosphatidate(18:2/20:0) | SMPDB, HMDB | Phosphatidate(18:2n6/20:0) | SMPDB, HMDB | Phosphatidate(18:2w6/20:0) | SMPDB, HMDB | Phosphatidate(38:2) | SMPDB, HMDB | PA(18:2(9Z,12Z)/20:0) | SMPDB |
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Chemical Formula | C41H77O8P |
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Average Molecular Weight | 729.033 |
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Monoisotopic Molecular Weight | 728.535606437 |
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IUPAC Name | [(2R)-2-(icosanoyloxy)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-(icosanoyloxy)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C41H77O8P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(43)49-39(38-48-50(44,45)46)37-47-40(42)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h12,14,18,21,39H,3-11,13,15-17,19-20,22-38H2,1-2H3,(H2,44,45,46)/b14-12-,21-18-/t39-/m1/s1 |
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InChI Key | RWRJNTNOUDDJGX-DAMGCGSSSA-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 | |
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Process | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:0) (PathBank: SMP0016012)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:1(11Z)) (PathBank: SMP0016013)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0016014)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/18:2(9Z,12Z)) (PathBank: SMP0024167)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0024168)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:2(13Z,16Z)) (PathBank: SMP0024169)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0024170)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0024171)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0024172)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024173)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024174)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0024175)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024176)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024177)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:2(11Z,14Z)) (PathBank: SMP0033241)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0033242)
- Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0) (PathBank: SMP0063863)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0066707)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:0) (PathBank: SMP0066712)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:1(13Z)) (PathBank: SMP0066713)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:0) (PathBank: SMP0066719)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:1(15Z)) (PathBank: SMP0066720)
- Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0) (PathBank: SMP0071765)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:0) (PathBank: SMP0081987)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:1(11Z)) (PathBank: SMP0081988)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:1(13Z)) (PathBank: SMP0081989)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/22:0) (PathBank: SMP0081990)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/22:1(13Z)) (PathBank: SMP0081991)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(11Z)/20:1(11Z)) (PathBank: SMP0081992)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(11Z)/20:1(13Z)) (PathBank: SMP0081993)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(11Z)/22:0) (PathBank: SMP0081994)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(11Z)/22:1(13Z)) (PathBank: SMP0081995)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(13Z)/20:1(13Z)) (PathBank: SMP0081996)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(13Z)/22:0) (PathBank: SMP0081997)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(13Z)/22:1(13Z)) (PathBank: SMP0081998)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/22:0/22:0) (PathBank: SMP0081999)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/22:0/22:1(13Z)) (PathBank: SMP0082000)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/22:1(13Z)/22:1(13Z)) (PathBank: SMP0082001)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:3(5Z,8Z,11Z)) (PathBank: SMP0085362)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0085363)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085364)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085365)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085366)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0085367)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085368)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085369)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085370)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085371)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0085372)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085373)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085374)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085375)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0085376)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085377)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085378)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0085379)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085380)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0085381)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0099786)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0099787)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)/22:0) (PathBank: SMP0099792)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z)) (PathBank: SMP0099793)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)/22:0) (PathBank: SMP0099795)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z)) (PathBank: SMP0099796)
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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(18:2(9Z,12Z)/20:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 5144.4 | Semi standard non polar | 33892256 | PA(18:2(9Z,12Z)/20:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 4564.0 | Standard non polar | 33892256 | PA(18:2(9Z,12Z)/20:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 5945.0 | Standard polar | 33892256 | PA(18:2(9Z,12Z)/20:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 5108.3 | Semi standard non polar | 33892256 | PA(18:2(9Z,12Z)/20:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 4536.9 | Standard non polar | 33892256 | PA(18:2(9Z,12Z)/20:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 5218.1 | Standard polar | 33892256 | PA(18:2(9Z,12Z)/20:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 5375.6 | Semi standard non polar | 33892256 | PA(18:2(9Z,12Z)/20:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 4650.5 | Standard non polar | 33892256 | PA(18:2(9Z,12Z)/20:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCC | 5929.8 | 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(18:2(9Z,12Z)/20:0) 10V, Positive-QTOF | splash10-01r2-1092602400-7f9b68f4fee7a571dd81 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 20V, Positive-QTOF | splash10-0002-2192202000-2c3fba969691a40ae7f6 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 40V, Positive-QTOF | splash10-0fya-1093003000-b4e0cffd8e361c34bbc5 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 10V, Negative-QTOF | splash10-01t9-4092300200-a8daeed48e329e9037cd | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 20V, Negative-QTOF | splash10-004i-9050000000-1645492456ff9c544147 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 40V, Negative-QTOF | splash10-004i-9000000000-275acfa8b4fc5a63e20e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 10V, Negative-QTOF | splash10-004i-0000000900-78de2b4b1a87619ed0a4 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 20V, Negative-QTOF | splash10-00or-0033900400-e25f583a6a9c58338c66 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 40V, Negative-QTOF | splash10-01t9-1196600100-aad181979cde4bfbd76f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 10V, Positive-QTOF | splash10-0udi-0000000900-f0b905cf11c47200d7a6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 20V, Positive-QTOF | splash10-0udi-0000009900-288397fd57e3bf8c6948 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 40V, Positive-QTOF | splash10-0uki-0000902300-5f77820dec98fd5d775d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 10V, Positive-QTOF | splash10-03fr-0000000900-d2b1917d92b4e8adf248 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 20V, Positive-QTOF | splash10-0059-0000005900-f502046e66db245b43b1 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/20:0) 40V, Positive-QTOF | splash10-00ls-0000906200-e3477624c8ec30bff3d4 | 2021-09-22 | Wishart Lab | View Spectrum |
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