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 02:50:43 UTC |
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Update Date | 2022-11-30 19:25:56 UTC |
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HMDB ID | HMDB0114836 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(16:0/18:3(6Z,9Z,12Z)) |
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Description | PA(16:0/18:3(6Z,9Z,12Z)) 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(16:0/18:3(6Z,9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of gamma-linolenic 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)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C37H67O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,22,24,35H,3-10,12,14-16,19-21,23,25-34H2,1-2H3,(H2,40,41,42)/b13-11-,18-17-,24-22-/t35-/m1/s1 |
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Synonyms | Value | Source |
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1-Palmitoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate | HMDB | 1-Palmitoyl-2-gamma-linolenoyl-sn-phosphatidic acid | HMDB | PA(16:0/18:3) | HMDB | PA(16:0/18:3N6) | HMDB | PA(16:0/18:3W6) | HMDB | PA(34:3) | HMDB | Phosphatidic acid(16:0/18:3(6Z,9Z,12Z)) | HMDB | Phosphatidic acid(16:0/18:3) | HMDB | Phosphatidic acid(16:0/18:3n6) | HMDB | Phosphatidic acid(16:0/18:3W6) | HMDB | Phosphatidic acid(34:3) | HMDB | Phosphatidate(16:0/18:3(6Z,9Z,12Z)) | HMDB | Phosphatidate(16:0/18:3) | HMDB | Phosphatidate(16:0/18:3N6) | HMDB | Phosphatidate(16:0/18:3W6) | HMDB | Phosphatidate(34:3) | HMDB | 1-palmitoyl-2-gamma-linolenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-palmitoyl-2-gamma-linolenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(16:0/18:3) | SMPDB, HMDB | PA(16:0/18:3n6) | SMPDB, HMDB | PA(16:0/18:3w6) | SMPDB, HMDB | PA(34:3) | SMPDB, HMDB | Phosphatidic acid(16:0/18:3(6Z,9Z,12Z)) | SMPDB, HMDB | Phosphatidic acid(16:0/18:3) | SMPDB, HMDB | Phosphatidic acid(16:0/18:3n6) | SMPDB, HMDB | Phosphatidic acid(16:0/18:3w6) | SMPDB, HMDB | Phosphatidic acid(34:3) | SMPDB, HMDB | Phosphatidate(16:0/18:3(6Z,9Z,12Z)) | SMPDB, HMDB | Phosphatidate(16:0/18:3) | SMPDB, HMDB | Phosphatidate(16:0/18:3n6) | SMPDB, HMDB | Phosphatidate(16:0/18:3w6) | SMPDB, HMDB | PA(16:0/18:3(6Z,9Z,12Z)) | SMPDB |
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Chemical Formula | C37H67O8P |
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Average Molecular Weight | 670.909 |
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Monoisotopic Molecular Weight | 670.457356115 |
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IUPAC Name | [(2R)-3-(hexadecanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-(hexadecanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C37H67O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,22,24,35H,3-10,12,14-16,19-21,23,25-34H2,1-2H3,(H2,40,41,42)/b13-11-,18-17-,24-22-/t35-/m1/s1 |
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InChI Key | MIXAOIFLPJPSKQ-YUUQBSMXSA-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 | Not Available |
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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 | | Show more...
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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(16:0/18:3(6Z,9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4725.2 | Semi standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4225.6 | Standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5534.8 | Standard polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4697.0 | Semi standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4200.6 | Standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4817.0 | Standard polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4947.4 | Semi standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4327.9 | Standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5515.2 | Standard polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 5148.9 | Semi standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4377.3 | Standard non polar | 33892256 | PA(16:0/18:3(6Z,9Z,12Z)),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4874.1 | Standard polar | 33892256 |
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Spectra |
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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(16:0/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF | splash10-022i-1192213000-34ca8490b0d4fca25985 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF | splash10-01p2-1292111000-f88f846eaef5459f3ba0 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF | splash10-03dj-1292020000-654b3e4ad2ba33b4209e | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 10V, Negative-QTOF | splash10-0a70-3091102000-539c74f4659c6c4a005b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 20V, Negative-QTOF | splash10-004i-9060000000-4f259776fa2c7b37e4e8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 40V, Negative-QTOF | splash10-004i-9000000000-58d8bbba306b03d9fe21 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF | splash10-0006-0000009000-680ea39749ce57da07e7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF | splash10-0008-0000099000-24d12db87a2f5ea02832 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF | splash10-05np-0000923000-5244466f683cc623cfec | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 10V, Negative-QTOF | splash10-014i-0000009000-8465477f36ce6d978aa8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 20V, Negative-QTOF | splash10-07xx-1196606000-2fb7b57502ea5ed83a69 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 40V, Negative-QTOF | splash10-0a6r-0090200000-f94932aa09d9ffb76057 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 10V, Positive-QTOF | splash10-0uk9-0000009000-4b00c8059dd5f287deb6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 20V, Positive-QTOF | splash10-00di-0000059000-000f7a098a0436ba96d3 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(16:0/18:3(6Z,9Z,12Z)) 40V, Positive-QTOF | splash10-00xu-0006693000-c74d65f2727b49984707 | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB095434 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 74876602 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 52929497 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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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