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 05:09:04 UTC |
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Update Date | 2022-11-30 19:26:16 UTC |
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HMDB ID | HMDB0115589 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PA(22:0/20:2(11Z,14Z)) |
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Description | PA(22:0/20:2(11Z,14Z)) 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(22:0/20:2(11Z,14Z)), in particular, consists of one chain of behenic acid at the C-1 position and one chain of eicosadienoic 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)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C45H85O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-44(46)51-41-43(42-52-54(48,49)50)53-45(47)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,43H,3-11,13,15-17,19,21-42H2,1-2H3,(H2,48,49,50)/b14-12-,20-18-/t43-/m1/s1 |
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Synonyms | Value | Source |
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1-behenoyl-2-eicosadienoyl-sn-glycero-3-phosphate | SMPDB, HMDB | 1-behenoyl-2-eicosadienoyl-sn-phosphatidic acid | SMPDB, HMDB | PA(22:0/20:2) | SMPDB, HMDB | PA(22:0/20:2n6) | SMPDB, HMDB | PA(22:0/20:2w6) | SMPDB, HMDB | PA(42:2) | SMPDB, HMDB | Phosphatidic acid(22:0/20:2(11Z,14Z)) | SMPDB, HMDB | Phosphatidic acid(22:0/20:2) | SMPDB, HMDB | Phosphatidic acid(22:0/20:2n6) | SMPDB, HMDB | Phosphatidic acid(22:0/20:2w6) | SMPDB, HMDB | Phosphatidic acid(42:2) | SMPDB, HMDB | Phosphatidate(22:0/20:2(11Z,14Z)) | SMPDB, HMDB | Phosphatidate(22:0/20:2) | SMPDB, HMDB | Phosphatidate(22:0/20:2n6) | SMPDB, HMDB | Phosphatidate(22:0/20:2w6) | SMPDB, HMDB | Phosphatidate(42:2) | SMPDB, HMDB | PA(22:0/20:2(11Z,14Z)) | SMPDB |
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Chemical Formula | C45H85O8P |
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Average Molecular Weight | 785.141 |
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Monoisotopic Molecular Weight | 784.598206695 |
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IUPAC Name | [(2R)-3-(docosanoyloxy)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxy]phosphonic acid |
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Traditional Name | (2R)-3-(docosanoyloxy)-2-[(11Z,14Z)-icosa-11,14-dienoyloxy]propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C45H85O8P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-44(46)51-41-43(42-52-54(48,49)50)53-45(47)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,43H,3-11,13,15-17,19,21-42H2,1-2H3,(H2,48,49,50)/b14-12-,20-18-/t43-/m1/s1 |
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InChI Key | KTDMYJDOWSUGOT-RNLCRUPCSA-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(22:0/20:2(11Z,14Z)/14:1(9Z)) (PathBank: SMP0036209)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/16:1(9Z)) (PathBank: SMP0036210)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/18:1(11Z)) (PathBank: SMP0036211)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/18:1(9Z)) (PathBank: SMP0036212)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/18:2(9Z,12Z)) (PathBank: SMP0036213)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/18:3(6Z,9Z,12Z)) (PathBank: SMP0036214)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/18:3(9Z,12Z,15Z)) (PathBank: SMP0036215)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/18:4(6Z,9Z,12Z,15Z)) (PathBank: SMP0036216)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:1(11Z)) (PathBank: SMP0036217)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:2(11Z,14Z)) (PathBank: SMP0036218)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) (PathBank: SMP0036219)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z)) (PathBank: SMP0036220)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0036221)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)) (PathBank: SMP0036222)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (PathBank: SMP0036223)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:0) (PathBank: SMP0036224)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:1(13Z)) (PathBank: SMP0036225)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:2(13Z,16Z)) (PathBank: SMP0036226)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) (PathBank: SMP0036227)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0036228)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0036229)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0036230)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/24:0) (PathBank: SMP0036231)
- De Novo Triacylglycerol Biosynthesis TG(22:0/20:2(11Z,14Z)/24:1(15Z)) (PathBank: SMP0036232)
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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(22:0/20:2(11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 5585.5 | Semi standard non polar | 33892256 | PA(22:0/20:2(11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 4896.5 | Standard non polar | 33892256 | PA(22:0/20:2(11Z,14Z)),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C | 6298.2 | Standard polar | 33892256 | PA(22:0/20:2(11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 5810.9 | Semi standard non polar | 33892256 | PA(22:0/20:2(11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 4972.1 | Standard non polar | 33892256 | PA(22:0/20:2(11Z,14Z)),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 6274.6 | 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(22:0/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-007d-1159802700-48cda1a20965bf2bccc7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-007n-3279402200-7222e23db77e1264a7e7 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-000t-1189002100-d10c5ca216a492fa3c26 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 10V, Negative-QTOF | splash10-00a9-3019300200-41c534ee316878921a75 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 20V, Negative-QTOF | splash10-004i-9014000000-363eb3afd88f905ed195 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9000000000-cb7ff3847f6c854ab42b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-0a4i-0000000090-2905b791fe7035e82c84 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-0a4i-0000000990-aa0e9993ac69b7c8d8d2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-0ap1-0000920230-10d1541e32ce24e7d5c3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 10V, Negative-QTOF | splash10-001i-0000000900-bba71d4ef7dbb1d8999e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 20V, Negative-QTOF | splash10-057u-0006900400-ca69e47f8610ae6d7caa | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 40V, Negative-QTOF | splash10-052r-0009300000-2a450499582baa551c4f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 10V, Positive-QTOF | splash10-014r-0000000900-467aa2bab35433af3626 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 20V, Positive-QTOF | splash10-000i-0000005900-133fda139cc6cf424097 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PA(22:0/20:2(11Z,14Z)) 40V, Positive-QTOF | splash10-002s-0000906200-699fad60ea9eab269eb8 | 2021-09-24 | Wishart Lab | View Spectrum |
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