Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2019-12-02 16:13:24 UTC |
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Update Date | 2022-11-30 19:53:42 UTC |
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HMDB ID | HMDB0240601 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | LysoPG(16:0/0:0) |
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Description | LysoPG(16:0/0:0) is a lysophosphatidylglycerol. It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic. However, it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylglycerols can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPG(16:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position. |
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Structure | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@@H](O)CO InChI=1S/C22H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(26)29-17-21(25)19-31-32(27,28)30-18-20(24)16-23/h20-21,23-25H,2-19H2,1H3,(H,27,28)/t20-,21+/m0/s1 |
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Synonyms | Value | Source |
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1-Palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol) | ChEBI | LPG(16:0/0:0) | ChEBI | PG(16:0/0:0) | ChEBI | 1-Palmitoyl-GPG | HMDB | 1-Palmitoyl-lysophosphatidylglycerol | HMDB | 1-Palmitoyl-sn-glycero-3-phospho-(1’-sn-glycerol) | HMDB | 1-Palmitoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(16:0) | HMDB | GPG(16:0/0:0) | HMDB | LPG(16:0) | HMDB | LysoPG(16:0) | HMDB | Lysophosphatidylglycerol(16:0) | HMDB | Lysophosphatidylglycerol(16:0/0:0) | HMDB | LysoPG(16:0/0:0) | HMDB |
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Chemical Formula | C22H45O9P |
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Average Molecular Weight | 484.567 |
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Monoisotopic Molecular Weight | 484.280120027 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy)phosphinic acid |
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CAS Registry Number | 116870-26-9 |
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SMILES | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@@H](O)CO |
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InChI Identifier | InChI=1S/C22H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(26)29-17-21(25)19-31-32(27,28)30-18-20(24)16-23/h20-21,23-25H,2-19H2,1H3,(H,27,28)/t20-,21+/m0/s1 |
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InChI Key | BVJSKAUUFXBDOB-LEWJYISDSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lysophosphatidylglycerols. These are glycerophosphoglycerols (molecules containing a glycerol moiety attached to the phosphate group linked to a glycerol) in which only one fatty acid is bonded to the 1-glycerol moiety (through an ester linkage). |
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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 | Lysophosphatidylglycerols |
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Alternative Parents | |
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Substituents | - Monoacylglycerophosphoglycerol
- Fatty acid ester
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Carboxylic acid ester
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Primary alcohol
- 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 | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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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 | | Show more...
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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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LysoPG(16:0/0:0),1TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO)O[Si](C)(C)C | 3575.1 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),1TMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C | 3546.5 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),1TMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C | 3512.4 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),1TMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C | 3570.9 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C | 3556.1 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C | 3537.2 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C)O[Si](C)(C)C | 3569.3 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C | 3537.7 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TMS,isomer #5 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C | 3579.7 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TMS,isomer #6 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C | 3555.6 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3530.6 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3556.3 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3558.8 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3562.3 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),4TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3539.4 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),4TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3264.6 | Standard non polar | 33892256 | LysoPG(16:0/0:0),4TMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3777.4 | Standard polar | 33892256 | LysoPG(16:0/0:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO)O[Si](C)(C)C(C)(C)C | 3812.7 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),1TBDMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C(C)(C)C | 3801.4 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),1TBDMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C(C)(C)C | 3789.6 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),1TBDMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C(C)(C)C | 3798.1 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TBDMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4035.1 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TBDMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4028.0 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TBDMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4043.0 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TBDMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4028.2 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TBDMS,isomer #5 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4031.2 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),2TBDMS,isomer #6 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4021.5 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TBDMS,isomer #1 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4257.0 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TBDMS,isomer #2 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4248.7 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TBDMS,isomer #3 | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4251.2 | Semi standard non polar | 33892256 | LysoPG(16:0/0:0),3TBDMS,isomer #4 | CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4249.3 | Semi standard non polar | 33892256 |
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Spectra |
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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 - LysoPG(16:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - LysoPG(16:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - LysoPG(16:0/0:0) 10V, Negative-QTOF | splash10-001i-0000900000-6601011f138ae3d70cc1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPG(16:0/0:0) 20V, Negative-QTOF | splash10-001i-0000900000-6601011f138ae3d70cc1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPG(16:0/0:0) 40V, Negative-QTOF | splash10-0a59-0191700000-7ec41cf244350dc72884 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | C00059317 |
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Chemspider ID | 24823104 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 42607483 |
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PDB ID | Not Available |
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ChEBI ID | 75376 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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