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 08:14:33 UTC |
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Update Date | 2022-11-30 19:26:37 UTC |
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HMDB ID | HMDB0116471 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) |
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Description | PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylglycerophosphate (PGP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. Phosphatidylglycerolphosphate 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 phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for cardiolipin synthesis. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of eicosatetraenoic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. They are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to phosphatidylglycerols (PGs). While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. |
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Structure | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C46H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-45(48)55-41-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)59-46(49)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,23-26,30,32,43-44,47H,3-4,6,8-10,15-16,21-22,27-29,31,33-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b7-5-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,32-30-/t43-,44+/m0/s1 |
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Synonyms | Value | Source |
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1-eicosatetraenoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | SMPDB, HMDB | PGP(20:4/20:4) | SMPDB, HMDB | PGP(20:4n3/20:4n6) | SMPDB, HMDB | PGP(20:4w3/20:4w6) | SMPDB, HMDB | PGP(40:8) | SMPDB, HMDB | PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) | SMPDB | PGP(20:4/20:4) | Lipid Annotator | 1-eicsoatetraenoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | Lipid Annotator, HMDB | 1-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | [(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C46H76O13P2 |
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Average Molecular Weight | 899.049 |
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Monoisotopic Molecular Weight | 898.476116503 |
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IUPAC Name | [(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid |
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Traditional Name | (2S)-2-hydroxy-3-{[hydroxy((2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C46H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-45(48)55-41-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)59-46(49)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,23-26,30,32,43-44,47H,3-4,6,8-10,15-16,21-22,27-29,31,33-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b7-5-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,32-30-/t43-,44+/m0/s1 |
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InChI Key | TWBQBGSJYVEAOM-KMXSEVSUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety 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 | Glycerophosphoglycerophosphates |
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Direct Parent | Phosphatidylglycerophosphates |
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Alternative Parents | |
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Substituents | - Diacylglycerophosphoglycerophosphate
- Sn-glycerol-3-phosphate
- Fatty acid ester
- Monoalkyl phosphate
- Dialkyl phosphate
- Dicarboxylic acid or derivatives
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- 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 | |
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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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PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 6307.2 | Standard polar | 33892256 | PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 4921.8 | Standard non polar | 33892256 | PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC | 6191.0 | Semi standard non 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 - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-0002-1362253290-796b2fdf9a8a3bd3a810 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-053b-4594133430-8e1c5b28f0613dca62ba | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0a4j-9346124500-aa91d8e4563e55acd9ca | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0ug1-7097022150-d3c1940cfbb3609078e6 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-0fb9-9032000000-06aad147a315cc70c888 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-004i-9000000000-8259c4cf6207672a3483 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF | splash10-0002-1000002490-f5930fbfe633229f3c6f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF | splash10-0kbb-1200003920-0ebeddb27efed06ac673 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF | splash10-0udi-0091011000-854faf2cdfa0869093de | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF | splash10-0002-0010000090-03a190e1dcdd52224b21 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF | splash10-0f6t-3093182030-b8ba6739dcbcd0242879 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF | splash10-0fba-2091140000-ddb76b363df3ef01b4ca | 2021-09-24 | Wishart Lab | View Spectrum |
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