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 03:43:48 UTC |
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Update Date | 2022-11-30 19:26:04 UTC |
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HMDB ID | HMDB0115144 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(20:4(5Z,8Z,11Z,14Z)/14:0) |
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Description | PA(20:4(5Z,8Z,11Z,14Z)/14:0) 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(20:4(5Z,8Z,11Z,14Z)/14:0), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of myristic 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)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC InChI=1S/C37H65O8P/c1-3-5-7-9-11-13-15-16-17-18-19-20-22-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-21-14-12-10-8-6-4-2/h11,13,16-17,19-20,23,25,35H,3-10,12,14-15,18,21-22,24,26-34H2,1-2H3,(H2,40,41,42)/b13-11-,17-16-,20-19-,25-23-/t35-/m1/s1 |
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Synonyms | Value | Source |
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1-arachidonoyl-2-myristoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-arachidonoyl-2-myristoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(20:4/14:0) | SMPDB, HMDB | PA(20:4n6/14:0) | SMPDB, HMDB | PA(20:4w6/14:0) | SMPDB, HMDB | PA(34:4) | SMPDB, HMDB | Phosphatidic acid(20:4(5Z,8Z,11Z,14Z)/14:0) | SMPDB, HMDB | Phosphatidic acid(20:4/14:0) | SMPDB, HMDB | Phosphatidic acid(20:4n6/14:0) | SMPDB, HMDB | Phosphatidic acid(20:4w6/14:0) | SMPDB, HMDB | Phosphatidic acid(34:4) | SMPDB, HMDB | Phosphatidate(20:4(5Z,8Z,11Z,14Z)/14:0) | SMPDB, HMDB | Phosphatidate(20:4/14:0) | SMPDB, HMDB | Phosphatidate(20:4n6/14:0) | SMPDB, HMDB | Phosphatidate(20:4w6/14:0) | SMPDB, HMDB | Phosphatidate(34:4) | SMPDB, HMDB | PA(20:4(5Z,8Z,11Z,14Z)/14:0) | SMPDB |
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Chemical Formula | C37H65O8P |
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Average Molecular Weight | 668.893 |
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Monoisotopic Molecular Weight | 668.441706051 |
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IUPAC Name | [(2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-(tetradecanoyloxy)propoxy]phosphonic acid |
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Traditional Name | (2R)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-2-(tetradecanoyloxy)propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C37H65O8P/c1-3-5-7-9-11-13-15-16-17-18-19-20-22-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-21-14-12-10-8-6-4-2/h11,13,16-17,19-20,23,25,35H,3-10,12,14-15,18,21-22,24,26-34H2,1-2H3,(H2,40,41,42)/b13-11-,17-16-,20-19-,25-23-/t35-/m1/s1 |
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InChI Key | XGGYURPUARRBSA-QFQPQIPXSA-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 | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/18:3(9Z,12Z,15Z)) (PathBank: SMP0016130)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0016131)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/22:2(13Z,16Z)) (PathBank: SMP0024721)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0024722)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0024723)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0024724)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0024725)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0024726)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024727)
- De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0024728)
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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(20:4(5Z,8Z,11Z,14Z)/14:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC | 4734.5 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC | 4220.5 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC | 5438.4 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC | 4702.4 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC | 4201.6 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC | 4711.0 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC | 4950.0 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC | 4334.5 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC | 5422.2 | Standard polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC | 5144.9 | Semi standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC | 4381.7 | Standard non polar | 33892256 | PA(20:4(5Z,8Z,11Z,14Z)/14:0),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC | 4773.9 | 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(20:4(5Z,8Z,11Z,14Z)/14:0) 10V, Positive-QTOF | splash10-02ti-1294325000-be4638cb8f5eb2c66794 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 20V, Positive-QTOF | splash10-01p2-2493121000-4c794301637278a3dd03 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 40V, Positive-QTOF | splash10-0292-1596041000-2b95927a6102d842e1c0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 10V, Negative-QTOF | splash10-0fvr-5096303000-98f5c1af8f37c8221f31 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 20V, Negative-QTOF | splash10-004i-9033000000-b3adf2f2925842eae47c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 40V, Negative-QTOF | splash10-004i-9000000000-a7314c60e63e4fb00fe7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 10V, Positive-QTOF | splash10-0uxr-0000009000-bc4118d373f2ace63551 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 20V, Positive-QTOF | splash10-01b9-0000059000-4bcb690eb848e4967651 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 40V, Positive-QTOF | splash10-00xu-0006693000-19567edd5e7ceac95d69 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 10V, Negative-QTOF | splash10-014i-0000009000-97bc48d486ef223a1313 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 20V, Negative-QTOF | splash10-0i2r-1139605000-d1dedfd0a91e6f079905 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 40V, Negative-QTOF | splash10-0ufr-1149201000-62f6f595143977f9c6c0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 10V, Positive-QTOF | splash10-0006-0000009000-6c13c0d0af92448808fc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 20V, Positive-QTOF | splash10-0006-0000099000-e1245ac0e399fb7fc244 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(20:4(5Z,8Z,11Z,14Z)/14:0) 40V, Positive-QTOF | splash10-01p6-0003934000-7d48bf473106bfec424e | 2021-09-23 | Wishart Lab | View Spectrum |
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