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 15:59:51 UTC |
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Update Date | 2022-11-30 19:53:42 UTC |
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HMDB ID | HMDB0240600 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | LysoPG(18:2(9Z,12Z)/0:0) |
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Description | LysoPG(18:2(9Z,12Z)/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(18:2(9Z,12Z)/0:0), in particular, consists of one chain of linoleic acid at the C-1 position. |
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Structure | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@@H](O)CO InChI=1S/C24H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24(28)31-19-23(27)21-33-34(29,30)32-20-22(26)18-25/h6-7,9-10,22-23,25-27H,2-5,8,11-21H2,1H3,(H,29,30)/b7-6-,10-9-/t22-,23+/m0/s1 |
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Synonyms | Value | Source |
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1-Linoleoyl-GPG | HMDB | 1-Linoleoyl-lysophosphatidylglycerol | HMDB | 1-Linoleoyl-sn-glycero-3-phospho-(1'-sn-glycerol) | HMDB | 1-Linoleoyl-sn-glycero-3-phospho-(1’-sn-glycerol) | HMDB | 1-Linoleoyl-sn-glycero-3-phosphoglycerol | HMDB | GPG(18:2(9Z,12Z)) | HMDB | GPG(18:2(9Z,12Z)/0:0) | HMDB | GPG(18:2) | HMDB | GPG(18:2N6) | HMDB | GPG(18:2N6/0:0) | HMDB | GPG(18:2W6) | HMDB | GPG(18:2W6/0:0) | HMDB | LPG(18:2(9Z,12Z)) | HMDB | LPG(18:2(9Z,12Z)/0:0) | HMDB | LPG(18:2) | HMDB | LPG(18:2n6) | HMDB | LPG(18:2n6/0:0) | HMDB | LPG(18:2W6) | HMDB | LPG(18:2W6/0:0) | HMDB | LysoPG(18:2(9Z,12Z)) | HMDB | LysoPG(18:2) | HMDB | LysoPG(18:2n6) | HMDB | LysoPG(18:2n6/0:0) | HMDB | LysoPG(18:2W6) | HMDB | LysoPG(18:2W6/0:0) | HMDB | Lysophosphatidylglycerol(18:2(9Z,12Z)) | HMDB | Lysophosphatidylglycerol(18:2(9Z,12Z)/0:0) | HMDB | Lysophosphatidylglycerol(18:2) | HMDB | Lysophosphatidylglycerol(18:2n6) | HMDB | Lysophosphatidylglycerol(18:2n6/0:0) | HMDB | Lysophosphatidylglycerol(18:2W6) | HMDB | Lysophosphatidylglycerol(18:2W6/0:0) | HMDB | LysoPG(18:2(9Z,12Z)/0:0) | HMDB |
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Chemical Formula | C24H45O9P |
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Average Molecular Weight | 508.589 |
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Monoisotopic Molecular Weight | 508.280120027 |
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IUPAC Name | [(2S)-2,3-dihydroxypropoxy][(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid |
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Traditional Name | (2S)-2,3-dihydroxypropoxy((2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid |
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CAS Registry Number | 2093174-30-0 |
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SMILES | CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@@H](O)CO |
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InChI Identifier | InChI=1S/C24H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24(28)31-19-23(27)21-33-34(29,30)32-20-22(26)18-25/h6-7,9-10,22-23,25-27H,2-5,8,11-21H2,1H3,(H,29,30)/b7-6-,10-9-/t22-,23+/m0/s1 |
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InChI Key | VEEHTGYBVMTAAF-RFFZIGDUSA-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 | |
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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(18:2(9Z,12Z)/0:0),1TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO)O[Si](C)(C)C | 3741.4 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C | 3758.1 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TMS,isomer #3 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C | 3748.8 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TMS,isomer #4 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C | 3720.0 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C | 3710.2 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C | 3713.2 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TMS,isomer #3 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C)O[Si](C)(C)C | 3697.4 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TMS,isomer #4 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C | 3706.8 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TMS,isomer #5 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@H](CO)O[Si](C)(C)C)O[Si](C)(C)C | 3710.3 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TMS,isomer #6 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO[Si](C)(C)C)O[Si](C)(C)C | 3709.2 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3649.7 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3659.3 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TMS,isomer #3 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3643.7 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TMS,isomer #4 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3646.4 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),4TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3648.2 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),4TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3339.1 | Standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),4TMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 3834.2 | Standard polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO)O[Si](C)(C)C(C)(C)C | 3958.0 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@H](CO)O[Si](C)(C)C(C)(C)C | 3977.3 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TBDMS,isomer #3 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC[C@@H](O)CO[Si](C)(C)C(C)(C)C | 3971.6 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),1TBDMS,isomer #4 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)COP(=O)(OC[C@@H](O)CO)O[Si](C)(C)C(C)(C)C | 3929.7 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4162.6 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4157.3 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TBDMS,isomer #3 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4147.6 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TBDMS,isomer #4 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4162.5 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TBDMS,isomer #5 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4150.7 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),2TBDMS,isomer #6 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4147.5 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TBDMS,isomer #1 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4355.4 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TBDMS,isomer #2 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4337.6 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TBDMS,isomer #3 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4339.0 | Semi standard non polar | 33892256 | LysoPG(18:2(9Z,12Z)/0:0),3TBDMS,isomer #4 | CCCCC/C=C\C/C=C\CCCCCCCC(=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 | 4343.1 | Semi standard non polar | 33892256 |
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