Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-09-08 16:35:15 UTC |
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Update Date | 2022-11-30 19:24:25 UTC |
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HMDB ID | HMDB0112177 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | FAHFA(18:0/6-O-18:0) |
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Description | Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are endogenous lipids found in adipose tissue and serum that correlate with insulin sensitivity and are reduced in insulin-resistant humans. Structurally, they are characterized by a branched ester linkage between a fatty acid and a hydroxy-fatty acid. Different positions of the branched ester on the hydroxy fatty acid results in different isomers. FAHFA(18:0/6-O-18:0), in particular, is formed from the condensation of the carboxy group of stearic acid with the hydroxy group of 6-hydroxyoctadecanoic acid. It is alternatively named 6-SAHSA since it is the 6-hydroxy isomer of the SAHSA (stearic acid-hydroxystearic acid) family. |
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Structure | CCCCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCC)CCCCC(O)=O InChI=1S/C36H70O4/c1-3-5-7-9-11-13-15-16-17-18-19-21-23-25-27-33-36(39)40-34(31-28-29-32-35(37)38)30-26-24-22-20-14-12-10-8-6-4-2/h34H,3-33H2,1-2H3,(H,37,38) |
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Synonyms | Value | Source |
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6-(Octadecanoyloxy)octadecanoate | Generator | 6-SAHSA | SMPDB, HMDB | 6-[(1-oxooctadecyl)oxy]-octadecanoic acid | SMPDB, HMDB | 6-(stearoyloxy)octadecanoic acid | SMPDB, HMDB | 6-(stearoyloxy)stearic acid | SMPDB, HMDB | stearic acid-6-hydroxystearic acid | SMPDB, HMDB | FAHFA(18:0/6-O-18:0) | SMPDB | 6-Stearoyloxystearate | Generator, HMDB |
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Chemical Formula | C36H70O4 |
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Average Molecular Weight | 566.952 |
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Monoisotopic Molecular Weight | 566.527410734 |
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IUPAC Name | 6-(octadecanoyloxy)octadecanoic acid |
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Traditional Name | 6-(octadecanoyloxy)octadecanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCC)CCCCC(O)=O |
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InChI Identifier | InChI=1S/C36H70O4/c1-3-5-7-9-11-13-15-16-17-18-19-21-23-25-27-33-36(39)40-34(31-28-29-32-35(37)38)30-26-24-22-20-14-12-10-8-6-4-2/h34H,3-33H2,1-2H3,(H,37,38) |
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InChI Key | FBBUCTRNJXSYIE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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 | Not Available |
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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 | Solid |
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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 IndicesUnderivatizedDerivatized |
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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 - FAHFA(18:0/6-O-18:0) GC-MS (1 TMS) - 70eV, Positive | splash10-00y0-9363373000-b74a4278b0b4ca280ce2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(18:0/6-O-18:0) GC-MS (Non-derivatized) - 70eV, Positive | splash10-00lf-8292830000-17e2402a877c3d3216b3 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(18:0/6-O-18:0) GC-MS ("FAHFA(18:0/6-O-18:0),1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(18:0/6-O-18:0) GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | 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 - FAHFA(18:0/6-O-18:0) 10V, Positive-QTOF | splash10-00l2-0050090000-1131f1ffd57490c384b6 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 20V, Positive-QTOF | splash10-015j-1190020000-6903c8ade7cbf7efd432 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 40V, Positive-QTOF | splash10-0076-3390100000-e494c45f47f15304cf4d | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 10V, Negative-QTOF | splash10-014i-0040090000-1e36f8cfe369b5ad3f36 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 20V, Negative-QTOF | splash10-00l2-0090040000-f5a922a184bb5611b244 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 40V, Negative-QTOF | splash10-0a5d-4290000000-6a92c83e1b20c0c9259c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 10V, Negative-QTOF | splash10-014i-0000090000-143671d6c91d192ee65d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 20V, Negative-QTOF | splash10-014i-0000090000-143671d6c91d192ee65d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:0/6-O-18:0) 40V, Negative-QTOF | splash10-01ak-0090030000-8fb495e5da53ceb2d73a | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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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 | 101527488 |
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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 | - Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
- Lopez-Bascon MA, Calderon-Santiago M, Priego-Capote F: Confirmatory and quantitative analysis of fatty acid esters of hydroxy fatty acids in serum by solid phase extraction coupled to liquid chromatography tandem mass spectrometry. Anal Chim Acta. 2016 Nov 2;943:82-88. doi: 10.1016/j.aca.2016.09.014. Epub 2016 Sep 20. [PubMed:27769381 ]
- 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 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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