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 08:19:10 UTC |
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Update Date | 2022-11-30 19:26:38 UTC |
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HMDB ID | HMDB0116496 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) |
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Description | PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 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(22:5(7Z,10Z,13Z,16Z,19Z)/16:0), in particular, consists of one chain of clupanodonic acid at the C-1 position and one chain of palmitic 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)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC InChI=1S/C44H78O13P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-43(46)53-39-42(40-56-59(51,52)55-38-41(45)37-54-58(48,49)50)57-44(47)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24-25,41-42,45H,3-4,6,8-10,12,14-16,19,22-23,26-40H2,1-2H3,(H,51,52)(H2,48,49,50)/b7-5-,13-11-,18-17-,21-20-,25-24-/t41-,42+/m0/s1 |
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Synonyms | Value | Source |
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1-clupanodonoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | SMPDB, HMDB | PGP(22:5/16:0) | SMPDB, HMDB | PGP(22:5n3/16:0) | SMPDB, HMDB | PGP(22:5w3/16:0) | SMPDB, HMDB | PGP(38:5) | SMPDB, HMDB | PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) | SMPDB | 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | Lipid Annotator, HMDB | 1-docosapentaenoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | PGP(22:5/16:0) | Lipid Annotator | 1-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | Lipid Annotator, HMDB | [(2S)-3-({[(2R)-3-[(7Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C44H78O13P2 |
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Average Molecular Weight | 877.043 |
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Monoisotopic Molecular Weight | 876.491766568 |
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IUPAC Name | [(2S)-3-({[(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid |
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Traditional Name | (2S)-3-{[(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]-2-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic 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)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C44H78O13P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-25-27-29-31-33-35-43(46)53-39-42(40-56-59(51,52)55-38-41(45)37-54-58(48,49)50)57-44(47)36-34-32-30-28-26-23-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,20-21,24-25,41-42,45H,3-4,6,8-10,12,14-16,19,22-23,26-40H2,1-2H3,(H,51,52)(H2,48,49,50)/b7-5-,13-11-,18-17-,21-20-,25-24-/t41-,42+/m0/s1 |
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InChI Key | GPIVLWADDPQZCN-RUVFBLPJSA-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 | Naturally occurring processBiological processBiochemical pathwayMetabolic pathway- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0095509)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) (PathBank: SMP0095510)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0095511)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)) (PathBank: SMP0095512)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)) (PathBank: SMP0095513)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) (PathBank: SMP0030045)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0030046)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0030047)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030048)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030049)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0030050)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0030051)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030052)
- Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0030053)
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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(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC | 5775.2 | Standard polar | 33892256 | PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC | 4928.4 | Standard non polar | 33892256 | PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCCCCCCCCCC | 6035.5 | 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(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 10V, Positive-QTOF | splash10-0a6r-1495036480-b534b20aaa6766a12289 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 20V, Positive-QTOF | splash10-0a4i-3494012320-fa88d1d8f6bf72950b98 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 40V, Positive-QTOF | splash10-0a4i-9676013500-f3ec5d3efd3084b2147b | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 10V, Negative-QTOF | splash10-004i-5059002130-f4dedd0ac67748efc497 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 20V, Negative-QTOF | splash10-004i-9023000000-1e45f75f7436937b901d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 40V, Negative-QTOF | splash10-004i-9000000000-8e8c8e0c237b32ea5065 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 10V, Positive-QTOF | splash10-004i-3110005970-201dd1632ca49aed2c00 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 20V, Positive-QTOF | splash10-056r-3411019800-25acf752f015bd3fd277 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 40V, Positive-QTOF | splash10-0udj-2198310000-08d8cdf278a96cfd918a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 10V, Negative-QTOF | splash10-004i-0010000090-41d62234e0f7e055249a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 20V, Negative-QTOF | splash10-0fba-3093033040-5e8b482cf845a5152d80 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - PGP(22:5(7Z,10Z,13Z,16Z,19Z)/16:0) 40V, Negative-QTOF | splash10-0udj-3092215000-da3bbf829bbaef3d16ff | 2021-09-22 | Wishart Lab | View Spectrum |
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Pathways | |
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