Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 21:12:12 UTC |
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Updated at | 2024-09-11 21:12:12 UTC |
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NP-MRD ID | NP0339331 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | PGP(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) |
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Description | PGP(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)), also known as PGP(18:2/20:4) Or PGP(38:6), 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. It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. PGP(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). 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 at up to 11% of the total. Finally, phosphatidylglycerol is formed by the action of specific phosphatases. Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). |
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Structure | [H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C44H76O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(47)57-42(40-56-59(51,52)55-38-41(45)37-54-58(48,49)50)39-53-43(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,28,30,41-42,45H,3-10,15-16,20,23,25-27,29,31-40H2,1-2H3,(H,51,52)(H2,48,49,50)/b13-11-,14-12-,19-17-,21-18-,24-22-,30-28-/t41-,42+/m0/s1 |
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Synonyms | Value | Source |
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1-Linoleoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | HMDB | 3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | HMDB | PGP(18:2/20:4) | HMDB | PGP(18:2n6/20:4n6) | HMDB | PGP(18:2W6/20:4W6) | HMDB | PGP(38:6) | HMDB | 1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | HMDB | PGP(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) | Lipid Annotator |
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Chemical Formula | C44H76O13P2 |
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Average Mass | 875.0140 Da |
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Monoisotopic Mass | 874.47612 Da |
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IUPAC Name | [(2S)-2-hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C44H76O13P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-44(47)57-42(40-56-59(51,52)55-38-41(45)37-54-58(48,49)50)39-53-43(46)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11-14,17-19,21-22,24,28,30,41-42,45H,3-10,15-16,20,23,25-27,29,31-40H2,1-2H3,(H,51,52)(H2,48,49,50)/b13-11-,14-12-,19-17-,21-18-,24-22-,30-28-/t41-,42+/m0/s1 |
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InChI Key | YKNSEHJIUGCGGV-KJNUSYEHSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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Species of Origin | Not Available |
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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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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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