Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-09 08:29:32 UTC |
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Update Date | 2019-07-23 09:22:11 UTC |
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HMDB ID | HMDB0116560 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | PGP(i-13:0/i-18:0) |
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Description | PGP(i-13:0/i-18:0) 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(i-13:0/i-18:0), in particular, consists of one chain of isotridecanoic acid at the C-1 position and one chain of isooctadecanoic 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 | |
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Synonyms | Value | Source |
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1-isotridecanoyl-2-isooctadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) | SMPDB, HMDB | PGP(i-13:0/i-18:0) | SMPDB | PGP(31:0) | SMPDB, HMDB | 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid | Lipid Annotator, HMDB | [(2S)-2-Hydroxy-3-({hydroxy[(2R)-3-[(11-methyldodecanoyl)oxy]-2-[(16-methylheptadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonate | Generator, HMDB |
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Chemical Formula | C37H74O13P2 |
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Average Molecular Weight | 788.934 |
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Monoisotopic Molecular Weight | 788.460466439 |
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IUPAC Name | [(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(11-methyldodecanoyl)oxy]-2-[(16-methylheptadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid |
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Traditional Name | (2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(11-methyldodecanoyl)oxy]-2-[(16-methylheptadecanoyl)oxy]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)CCCCCCCCCC(C)C)OC(=O)CCCCCCCCCCCCCCC(C)C |
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InChI Identifier | InChI=1S/C37H74O13P2/c1-32(2)24-20-16-12-9-7-5-6-8-10-14-19-23-27-37(40)50-35(31-49-52(44,45)48-29-34(38)28-47-51(41,42)43)30-46-36(39)26-22-18-15-11-13-17-21-25-33(3)4/h32-35,38H,5-31H2,1-4H3,(H,44,45)(H2,41,42,43)/t34-,35+/m0/s1 |
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InChI Key | YWPAZYGQWCHVFN-OIDHKYIRSA-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 | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05ts-1680071900-478461b6f685c8c2fe36 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05tb-5981043300-5a1a4e579808b39a89ef | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9681141100-beccf4416bd7ae32da57 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01s2-4490031300-173d5b9eef5c393c9f5b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-9140000000-5702a0f4480a9cee5687 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9010000000-a84c292703f2853fde72 | Spectrum |
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Pathways | |
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General References | - Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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