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 06:17:53 UTC |
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Update Date | 2022-11-30 19:26:22 UTC |
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HMDB ID | HMDB0115867 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(i-21:0/18:0) |
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Description | PA(i-21:0/18:0) 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(i-21:0/18:0), in particular, consists of one chain of isoheneicosanoic acid at the C-1 position and one chain of stearic 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)CCCCCCCCCCCCCCCCCC(C)C)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC InChI=1S/C42H83O8P/c1-4-5-6-7-8-9-10-11-13-18-21-24-27-30-33-36-42(44)50-40(38-49-51(45,46)47)37-48-41(43)35-32-29-26-23-20-17-15-12-14-16-19-22-25-28-31-34-39(2)3/h39-40H,4-38H2,1-3H3,(H2,45,46,47)/t40-/m1/s1 |
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Synonyms | Value | Source |
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1-isoheneicosanoyl-2-stearoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-isoheneicosanoyl-2-stearoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(i-21:0/18:0) | SMPDB | PA(39:0) | SMPDB, HMDB | Phosphatidic acid(i-21:0/18:0) | SMPDB, HMDB | Phosphatidic acid(39:0) | SMPDB, HMDB | Phosphatidate(i-21:0/18:0) | SMPDB, HMDB | Phosphatidate(39:0) | SMPDB, HMDB | [(2R)-3-[(19-Methylicosanoyl)oxy]-2-(octadecanoyloxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C42H83O8P |
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Average Molecular Weight | 747.092 |
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Monoisotopic Molecular Weight | 746.582556631 |
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IUPAC Name | [(2R)-3-[(19-methylicosanoyl)oxy]-2-(octadecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(19-methylicosanoyl)oxy]-2-(octadecanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C42H83O8P/c1-4-5-6-7-8-9-10-11-13-18-21-24-27-30-33-36-42(44)50-40(38-49-51(45,46)47)37-48-41(43)35-32-29-26-23-20-17-15-12-14-16-19-22-25-28-31-34-39(2)3/h39-40H,4-38H2,1-3H3,(H2,45,46,47)/t40-/m1/s1 |
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InChI Key | HHJGPHZKKNBDPI-RRHRGVEJSA-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 | |
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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(i-21:0/18:0),1TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C | 5175.6 | Semi standard non polar | 33892256 | PA(i-21:0/18:0),1TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C | 4545.6 | Standard non polar | 33892256 | PA(i-21:0/18:0),1TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C | 6129.4 | Standard polar | 33892256 | PA(i-21:0/18:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5142.7 | Semi standard non polar | 33892256 | PA(i-21:0/18:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4569.9 | Standard non polar | 33892256 | PA(i-21:0/18:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5402.1 | Standard polar | 33892256 | PA(i-21:0/18:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5422.4 | Semi standard non polar | 33892256 | PA(i-21:0/18:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4659.4 | Standard non polar | 33892256 | PA(i-21:0/18:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCC(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 6082.0 | 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(i-21:0/18:0) 10V, Positive-QTOF | splash10-05mk-1196702700-71ab26884540d1bf231e | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 20V, Positive-QTOF | splash10-066s-3294201000-69a2ca7548f1a2908120 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 40V, Positive-QTOF | splash10-069r-2296012000-13c2c16678605d95bca2 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 10V, Negative-QTOF | splash10-004i-4039400300-a9d6516a64a19cbb02a0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 20V, Negative-QTOF | splash10-004i-9014000000-c43b6126fd2a48964b38 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 40V, Negative-QTOF | splash10-004i-9000000000-0ca54f840d9e96de564c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 10V, Positive-QTOF | splash10-014i-0000000900-1629fe939b0a7fbd4dd8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 20V, Positive-QTOF | splash10-01i0-0000009900-406333213a80d107ed79 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 40V, Positive-QTOF | splash10-0i73-0000922400-58f256c6caa2f55eb45f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 10V, Positive-QTOF | splash10-004j-0000000900-03b3a3dd5984a5ef11d8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 20V, Positive-QTOF | splash10-0002-0000005900-69c39371c25d2bc15151 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 40V, Positive-QTOF | splash10-01vk-0000906200-d40953509dd8fea4efb4 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 10V, Negative-QTOF | splash10-0002-0000000900-8363eccdcaf0a37b4af1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 20V, Negative-QTOF | splash10-02ea-0033900400-167ed4bdd845e04159ab | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(i-21:0/18:0) 40V, Negative-QTOF | splash10-0059-1169600100-3bd8f133a20e4500847f | 2021-09-24 | Wishart Lab | View Spectrum |
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