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 08:43:52 UTC |
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Update Date | 2022-11-30 19:26:41 UTC |
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HMDB ID | HMDB0116612 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) |
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Description | PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerol - a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of clupanodonic acid at the C-2 position. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant (up to 11% of the total). It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for cardiolipin synthesis. |
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Structure | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C48H77O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-48(52)58-46(44-57-59(53,54)56-42-45(50)41-49)43-55-47(51)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,22,24-25,27-28,30-31,33,45-46,49-50H,3-4,6,8-10,15-16,21,23,26,29,32,34-44H2,1-2H3,(H,53,54)/b7-5-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t45-,46+/m0/s1 |
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Synonyms | Value | Source |
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1-arachidonoyl-2-clupanodonoyl-sn-glycero-3-phospho-(1'-glycerol) | SMPDB, HMDB | 1-arachidonoyl-2-clupanodonoyl-sn-glycero-3-phosphoglycerol | SMPDB, HMDB | PG(20:4/22:5) | SMPDB, HMDB | PG(20:4n6/22:5n3) | SMPDB, HMDB | PG(20:4w6/22:5w3) | SMPDB, HMDB | PG(42:9) | SMPDB, HMDB | Phosphatidylglycerol(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB, HMDB | Phosphatidylglycerol(20:4/22:5) | SMPDB, HMDB | Phosphatidylglycerol(20:4n6/22:5n3) | SMPDB, HMDB | Phosphatidylglycerol(20:4w6/22:5w3) | SMPDB, HMDB | Phosphatidylglycerol(42:9) | SMPDB, HMDB | PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | SMPDB | 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phospho-(1'-glycerol) | Lipid Annotator, HMDB | GPG(42:9) | Lipid Annotator, HMDB | Phosphatidylglycerol(20:4/22:5) | Lipid Annotator | PG(20:4/22:5) | Lipid Annotator | PG(42:9) | Lipid Annotator | GPG(20:4/22:5) | Lipid Annotator, HMDB | 1-arachidonoyl-2-docosapentaenoyl-sn-glycero-3-phosphoglycerol | Lipid Annotator, HMDB | 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycero-3-phosphoglycerol | Lipid Annotator, HMDB | [(2S)-2,3-Dihydroxypropoxy][(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(5Z,8Z,11Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinate | Generator, HMDB |
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Chemical Formula | C48H77O10P |
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Average Molecular Weight | 845.108 |
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Monoisotopic Molecular Weight | 844.525435677 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy((2R)-2-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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InChI Identifier | InChI=1S/C48H77O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-48(52)58-46(44-57-59(53,54)56-42-45(50)41-49)43-55-47(51)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,22,24-25,27-28,30-31,33,45-46,49-50H,3-4,6,8-10,15-16,21,23,26,29,32,34-44H2,1-2H3,(H,53,54)/b7-5-,13-11-,14-12-,19-17-,20-18-,24-22-,27-25-,30-28-,33-31-/t45-,46+/m0/s1 |
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InChI Key | KCVMHPVLQZCJPS-BVOXZSGPSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. |
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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 | Glycerophosphoglycerols |
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Direct Parent | Phosphatidylglycerols |
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Alternative Parents | |
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Substituents | - 1,2-diacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- 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- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029766)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029767)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0029768)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (PathBank: SMP0029769)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0029770)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)) (PathBank: SMP0029771)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)) (PathBank: SMP0029772)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (PathBank: SMP0029773)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029774)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029775)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029776)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029777)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0029778)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0029779)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0029780)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0029781)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0029782)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0029783)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029784)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029785)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029786)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029787)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0029788)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0029789)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029790)
- Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0029791)
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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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 6131.1 | Standard polar | 33892256 | PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5027.1 | Standard non polar | 33892256 | PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) | [H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC | 5997.7 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-13 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Positive-QTOF | splash10-004j-4177072190-8b655bfc8a0f60625da8 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Positive-QTOF | splash10-01t9-5195032320-efeeb6b0c738653241e1 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Positive-QTOF | splash10-0bt9-9077101210-aa799ade843399027dd4 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-0ug0-1149030040-fa565fd593df79ed3bbf | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-0ufr-7359110100-133907fe4ee149e8e829 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-004i-9002000000-36c578045c0de3917ff6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 10V, Negative-QTOF | splash10-0006-0000000090-780d1b34c2a775a6836e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 20V, Negative-QTOF | splash10-0ufu-0009130040-901f87f33ff2ec1e040d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)) 40V, Negative-QTOF | splash10-0ufu-0109130040-f9e6b86a13af01291c1e | 2021-09-23 | Wishart Lab | View Spectrum |
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