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 03:30:42 UTC |
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Update Date | 2022-11-30 19:26:02 UTC |
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HMDB ID | HMDB0115068 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:0/18:1(11Z)) |
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Description | PA(20:0/18:1(11Z)) 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(20:0/18:1(11Z)), in particular, consists of one chain of arachidic acid at the C-1 position and one chain of cis-vaccenic 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)CCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC InChI=1S/C41H79O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h14,16,39H,3-13,15,17-38H2,1-2H3,(H2,44,45,46)/b16-14-/t39-/m1/s1 |
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Synonyms | Value | Source |
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1-arachidoyl-2-cis-vaccenoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-arachidoyl-2-cis-vaccenoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:0/18:1) | SMPDB, HMDB | PA(20:0/18:1n7) | SMPDB, HMDB | PA(20:0/18:1w7) | SMPDB, HMDB | PA(38:1) | SMPDB, HMDB | Phosphatidic acid(20:0/18:1(11Z)) | SMPDB, HMDB | Phosphatidic acid(20:0/18:1) | SMPDB, HMDB | Phosphatidic acid(20:0/18:1n7) | SMPDB, HMDB | Phosphatidic acid(20:0/18:1w7) | SMPDB, HMDB | Phosphatidic acid(38:1) | SMPDB, HMDB | Phosphatidate(20:0/18:1(11Z)) | SMPDB, HMDB | Phosphatidate(20:0/18:1) | SMPDB, HMDB | Phosphatidate(20:0/18:1n7) | SMPDB, HMDB | Phosphatidate(20:0/18:1w7) | SMPDB, HMDB | Phosphatidate(38:1) | SMPDB, HMDB | PA(20:0/18:1(11Z)) | SMPDB | [(2R)-3-(Icosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C41H79O8P |
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Average Molecular Weight | 731.049 |
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Monoisotopic Molecular Weight | 730.551256502 |
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IUPAC Name | [(2R)-3-(icosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-(icosanoyloxy)-2-[(11Z)-octadec-11-enoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC |
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InChI Identifier | InChI=1S/C41H79O8P/c1-3-5-7-9-11-13-15-17-19-20-22-23-25-27-29-31-33-35-40(42)47-37-39(38-48-50(44,45)46)49-41(43)36-34-32-30-28-26-24-21-18-16-14-12-10-8-6-4-2/h14,16,39H,3-13,15,17-38H2,1-2H3,(H2,44,45,46)/b16-14-/t39-/m1/s1 |
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InChI Key | ZTPMITUCMUDDPK-QRMPNUHKSA-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 | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:0) (PathBank: SMP0019067)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:0) (PathBank: SMP0019068)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/24:0) (PathBank: SMP0019069)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/14:1(9Z)) (PathBank: SMP0019070)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/16:1(9Z)) (PathBank: SMP0019071)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/18:1(11Z)) (PathBank: SMP0019072)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0019073)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:1(11Z)) (PathBank: SMP0019074)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0019075)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:1(13Z)) (PathBank: SMP0019076)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/24:1(15Z)) (PathBank: SMP0019077)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/18:2(9Z,12Z)) (PathBank: SMP0019078)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0019079)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0019080)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:2(13Z,16Z)) (PathBank: SMP0019081)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0019082)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0019083)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0019084)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0019085)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0019086)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0019087)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0019088)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0019089)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:2(11Z,14Z)) (PathBank: SMP0033748)
- De Novo Triacylglycerol Biosynthesis TG(20:0/18:1(11Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0033749)
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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(20:0/18:1(11Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5154.1 | Semi standard non polar | 33892256 | PA(20:0/18:1(11Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4565.7 | Standard non polar | 33892256 | PA(20:0/18:1(11Z)),1TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 6013.7 | Standard polar | 33892256 | PA(20:0/18:1(11Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5110.9 | Semi standard non polar | 33892256 | PA(20:0/18:1(11Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 4549.9 | Standard non polar | 33892256 | PA(20:0/18:1(11Z)),2TMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 5252.3 | Standard polar | 33892256 | PA(20:0/18:1(11Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5399.9 | Semi standard non polar | 33892256 | PA(20:0/18:1(11Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4662.4 | Standard non polar | 33892256 | PA(20:0/18:1(11Z)),1TBDMS,isomer #1 | CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5986.7 | 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(20:0/18:1(11Z)) 10V, Positive-QTOF | splash10-00ls-1092602400-7f1ca55cc71754675951 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 20V, Positive-QTOF | splash10-00kb-2192302100-52bef6dbc0ac77cc8344 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 40V, Positive-QTOF | splash10-0gba-1196004000-c6cfbaf86ae3e9bb4654 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 10V, Negative-QTOF | splash10-01tc-5095400300-58cc20c5628d454df795 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 20V, Negative-QTOF | splash10-004i-9032000000-8013cfb8e017f7ccf7ff | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 40V, Negative-QTOF | splash10-004i-9000000000-187b0a291b6cef7c021c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 10V, Negative-QTOF | splash10-004i-0000000900-a283756924b3a3ee4e13 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 20V, Negative-QTOF | splash10-02ea-0033900400-9ab8a072015668904dd5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 40V, Negative-QTOF | splash10-03e9-1169600100-88b5881a3cf9c749d150 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 10V, Positive-QTOF | splash10-03e9-0000000900-52482a39f0230a2d657d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 20V, Positive-QTOF | splash10-001i-0000005900-b9e0ac6bd66a7d765bee | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 40V, Positive-QTOF | splash10-00ls-0000906200-ead9d9c000e2d36ee344 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 10V, Positive-QTOF | splash10-0udi-0000000900-36a995545a31ada060af | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 20V, Positive-QTOF | splash10-14i0-0000009900-1f526111a91637e4f379 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:0/18:1(11Z)) 40V, Positive-QTOF | splash10-0pic-0000902300-4ea5020856add1ced69b | 2021-09-23 | Wishart Lab | View Spectrum |
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