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 20:46:15 UTC |
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Update Date | 2021-09-14 15:42:20 UTC |
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HMDB ID | HMDB0061703 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Stearoylglycerophosphoglycerol |
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Description | 2-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(0:0/18:0), 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)OC(CO)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)33-23(19-26)21-32-34(29,30)31-20-22(27)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)[3-hydroxy-2-(octadecanoyloxy)propoxy]phosphinic acid |
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Traditional Name | 2,3-dihydroxypropoxy(3-hydroxy-2-(octadecanoyloxy)propoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)OC(CO)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)33-23(19-26)21-32-34(29,30)31-20-22(27)18-25/h22-23,25-27H,2-21H2,1H3,(H,29,30) |
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InChI Key | ZYKIFISVQNGKFE-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 | | 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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2-Stearoylglycerophosphoglycerol,1TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)OCC(O)CO | 3789.7 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)OCC(CO)O[Si](C)(C)C | 3764.7 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)OCC(O)CO[Si](C)(C)C | 3772.5 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(O)CO)O[Si](C)(C)C | 3780.4 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)OCC(CO)O[Si](C)(C)C | 3731.8 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)OCC(O)CO[Si](C)(C)C | 3741.2 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(OCC(O)CO)O[Si](C)(C)C | 3735.0 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C | 3742.9 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TMS,isomer #5 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C | 3743.0 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TMS,isomer #6 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C | 3759.1 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C | 3718.6 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C | 3728.1 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C | 3732.4 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3738.6 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,4TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3725.4 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,4TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3431.4 | Standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,4TMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3916.8 | Standard polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)OCC(O)CO | 4049.8 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C | 4020.9 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TBDMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C | 4035.3 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,1TBDMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C | 4001.4 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C | 4241.7 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C | 4234.9 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TBDMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C | 4229.8 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TBDMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4245.9 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TBDMS,isomer #5 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4201.1 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,2TBDMS,isomer #6 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4194.0 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4460.1 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4412.4 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TBDMS,isomer #3 | CCCCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4409.2 | Semi standard non polar | 33892256 | 2-Stearoylglycerophosphoglycerol,3TBDMS,isomer #4 | CCCCCCCCCCCCCCCCCC(=O)OC(CO)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 | 4413.4 | 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 - 2-Stearoylglycerophosphoglycerol GC-MS (Non-derivatized) - 70eV, Positive | splash10-03dj-9840500000-775e29d5cae160619b89 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Stearoylglycerophosphoglycerol GC-MS (2 TMS) - 70eV, Positive | splash10-000g-9471026000-c9a013781b21aa6484b7 | 2017-10-06 | 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 - 2-Stearoylglycerophosphoglycerol 10V, Negative-QTOF | splash10-03gi-1290340000-139e7e6908381e87de98 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 20V, Negative-QTOF | splash10-004i-9540300000-8798b839cc182ef392de | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 40V, Negative-QTOF | splash10-004i-9110000000-4494c525f19b78d9e99a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 10V, Negative-QTOF | splash10-03di-0000090000-54364fa26fbff155b339 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 20V, Negative-QTOF | splash10-0hjj-2590020000-c5fb09dbe5a8fab4f3d9 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 40V, Negative-QTOF | splash10-004i-9420000000-b762e5e60e66876d781f | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 10V, Positive-QTOF | splash10-02dj-5191430000-11cf03585bf065954666 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 20V, Positive-QTOF | splash10-056r-8292200000-d0f21461efdfa3dd6de0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 40V, Positive-QTOF | splash10-056r-9130000000-a6838a4b74881068e5bc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 10V, Positive-QTOF | splash10-0006-0039410000-08111000dcda7729dc1e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 20V, Positive-QTOF | splash10-0006-0109100000-55247dc4e88ddfcdbaf0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Stearoylglycerophosphoglycerol 40V, Positive-QTOF | splash10-0a4j-9412000000-25c905110d8e21f9a928 | 2021-09-23 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- 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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Associated OMIM IDs | |
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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 | Not Available |
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Chemspider ID | Not Available |
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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 | 45479454 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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 | - 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 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- 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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