Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2014-04-16 20:45:58 UTC |
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Update Date | 2021-09-14 15:42:31 UTC |
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HMDB ID | HMDB0061697 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1-Stearoylglycerophosphoglycerol |
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Description | 1-Stearoylglycerophosphoglycerol is a phosphatidylglycerol. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PG(18:0/0:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes. |
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Structure | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCC(O)CO InChI=1S/C24H49O9P/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/h22-23,25-27H,2-21H2,1H3,(H,29,30) |
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Synonyms | Not Available |
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Chemical Formula | C24H49O9P |
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Average Molecular Weight | 512.6142 |
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Monoisotopic Molecular Weight | 512.311419678 |
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IUPAC Name | (2,3-dihydroxypropoxy)[2-hydroxy-3-(octadecanoyloxy)propoxy]phosphinic acid |
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Traditional Name | 2,3-dihydroxypropoxy(2-hydroxy-3-(octadecanoyloxy)propoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCC(O)CO |
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InChI Identifier | InChI=1S/C24H49O9P/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/h22-23,25-27H,2-21H2,1H3,(H,29,30) |
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InChI Key | HFJVKBVEKQHVTO-UHFFFAOYSA-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 | Not Available |
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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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1-Stearoylglycerophosphoglycerol,1TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO)O[Si](C)(C)C | 3854.7 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO)O[Si](C)(C)C | 3821.3 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(O)CO[Si](C)(C)C | 3837.4 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO)O[Si](C)(C)C | 3824.7 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C | 3780.5 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C | 3785.6 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO)O[Si](C)(C)C)O[Si](C)(C)C | 3801.4 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C | 3788.8 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TMS,isomer #5 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C | 3788.2 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TMS,isomer #6 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C | 3800.9 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3772.1 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3773.7 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3772.3 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3777.1 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,4TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3760.1 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,4TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3473.6 | Standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,4TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3946.3 | Standard polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO)O[Si](C)(C)C(C)(C)C | 4102.5 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C | 4064.2 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C | 4083.6 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C | 4050.2 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4294.1 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4289.9 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4283.6 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4295.9 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #5 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4250.5 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #6 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4244.0 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4518.7 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(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 | 4471.6 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(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 | 4462.0 | Semi standard non polar | 33892256 | 1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4466.8 | Semi standard non polar | 33892256 |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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