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 03:12:42 UTC |
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Update Date | 2022-11-30 19:25:59 UTC |
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HMDB ID | HMDB0114964 |
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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)/22:0) |
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Description | PA(18:2(9Z,12Z)/22:0) 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)/22:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of behenic 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)CCCCCCCCCCCCCCCCCCCCC InChI=1S/C43H81O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h12,14,18,23,41H,3-11,13,15-17,19-22,24-40H2,1-2H3,(H2,46,47,48)/b14-12-,23-18-/t41-/m1/s1 |
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Synonyms | Value | Source |
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1-linoleoyl-2-behenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-linoleoyl-2-behenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(18:2/22:0) | SMPDB, HMDB | PA(18:2n6/22:0) | SMPDB, HMDB | PA(18:2w6/22:0) | SMPDB, HMDB | PA(40:2) | SMPDB, HMDB | Phosphatidic acid(18:2(9Z,12Z)/22:0) | SMPDB, HMDB | Phosphatidic acid(18:2/22:0) | SMPDB, HMDB | Phosphatidic acid(18:2n6/22:0) | SMPDB, HMDB | Phosphatidic acid(18:2w6/22:0) | SMPDB, HMDB | Phosphatidic acid(40:2) | SMPDB, HMDB | Phosphatidate(18:2(9Z,12Z)/22:0) | SMPDB, HMDB | Phosphatidate(18:2/22:0) | SMPDB, HMDB | Phosphatidate(18:2n6/22:0) | SMPDB, HMDB | Phosphatidate(18:2w6/22:0) | SMPDB, HMDB | Phosphatidate(40:2) | SMPDB, HMDB | PA(18:2(9Z,12Z)/22:0) | SMPDB |
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Chemical Formula | C43H81O8P |
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Average Molecular Weight | 757.087 |
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Monoisotopic Molecular Weight | 756.566906566 |
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IUPAC Name | [(2R)-2-(docosanoyloxy)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-2-(docosanoyloxy)-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)CCCCCCCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C43H81O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h12,14,18,23,41H,3-11,13,15-17,19-22,24-40H2,1-2H3,(H2,46,47,48)/b14-12-,23-18-/t41-/m1/s1 |
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InChI Key | HMFSRCBVVSBNOC-DEPOTCCGSA-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)/22:0/22:0) (PathBank: SMP0066812)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:1(13Z)) (PathBank: SMP0066813)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/18:2(9Z,12Z)) (PathBank: SMP0024178)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/18:3(6Z,9Z,12Z)) (PathBank: SMP0024179)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0024180)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:2(13Z,16Z)) (PathBank: SMP0024181)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0024182)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0024183)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0024184)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024185)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024186)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0024187)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024188)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024189)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/20:2(11Z,14Z)) (PathBank: SMP0033281)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/20:3(8Z,11Z,14Z)) (PathBank: SMP0033282)
- Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0) (PathBank: SMP0063866)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:0) (PathBank: SMP0066819)
- De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:1(15Z)) (PathBank: SMP0066820)
- Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0) (PathBank: SMP0071768)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:0/22:0/22:0) (PathBank: SMP0082018)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:0/22:0/22:1(13Z)) (PathBank: SMP0082019)
- Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:0/22:1(13Z)/22:1(13Z)) (PathBank: SMP0082020)
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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)/22:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCC | 5363.1 | Semi standard non polar | 33892256 | PA(18:2(9Z,12Z)/22:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCC | 4730.2 | Standard non polar | 33892256 | PA(18:2(9Z,12Z)/22:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCCCCCC | 6121.7 | Standard polar | 33892256 | PA(18:2(9Z,12Z)/22:0),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)CCCCCCCCCCCCCCCCCCCCC | 5591.1 | Semi standard non polar | 33892256 | PA(18:2(9Z,12Z)/22:0),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)CCCCCCCCCCCCCCCCCCCCC | 4811.5 | Standard non polar | 33892256 | PA(18:2(9Z,12Z)/22:0),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)CCCCCCCCCCCCCCCCCCCCC | 6102.7 | 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)/22:0) 10V, Negative-QTOF | splash10-01t9-4093300300-278214b4fed4ad157665 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 20V, Negative-QTOF | splash10-004i-9050000000-309d784936d6d11953fb | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 40V, Negative-QTOF | splash10-004i-9000000000-d9693c44ccbc9bb8e031 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 10V, Negative-QTOF | splash10-0a4i-0000000900-f9b07091afdd70451bc6 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 20V, Negative-QTOF | splash10-05r0-0033900400-59231673057825f4c8b8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 40V, Negative-QTOF | splash10-004r-1196600100-c5b194d1f5beecfdf739 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 10V, Positive-QTOF | splash10-0c09-1179803700-bf3c2f2ff98c9e279c48 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 20V, Positive-QTOF | splash10-022a-3289303100-19272c1f4fb692721a5f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 40V, Positive-QTOF | splash10-00ej-1197003000-8f285878a931bcd56da4 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 10V, Positive-QTOF | splash10-004i-0000000900-2d64aac188790b8ef3cf | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 20V, Positive-QTOF | splash10-0060-0000009900-e8b951109f52d672624e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 40V, Positive-QTOF | splash10-05s1-0000922400-5ee8b6527a16eb1b21c5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 10V, Positive-QTOF | splash10-052r-0000000900-c57c572740dbfcb2dcda | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 20V, Positive-QTOF | splash10-0a4i-0000005900-d2a4285bb0dca97c8913 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(18:2(9Z,12Z)/22:0) 40V, Positive-QTOF | splash10-0ar0-0000906200-bd4c4fb67d2afc795bf8 | 2021-09-25 | Wishart Lab | View Spectrum |
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General References | - Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
- Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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