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 16:29:58 UTC |
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Update Date | 2022-11-30 19:24:24 UTC |
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HMDB ID | HMDB0112144 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | FAHFA(18:1(9Z)/11-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(18:1(9Z)/11-O-18:0), in particular, is formed from the condensation of the carboxy group of oleic acid with the hydroxy group of 11-hydroxyoctadecanoic acid. It is alternatively named 11-OAHSA since it is the 11-hydroxy isomer of the OAHSA (oleic acid-hydroxystearic acid) family. |
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Structure | [H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC(CCCCCCC)CCCCCCCCCC(O)=O InChI=1S/C36H68O4/c1-3-5-7-9-10-11-12-13-14-15-16-17-21-25-29-33-36(39)40-34(30-26-22-8-6-4-2)31-27-23-19-18-20-24-28-32-35(37)38/h13-14,34H,3-12,15-33H2,1-2H3,(H,37,38)/b14-13- |
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Synonyms | Value | Source |
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11-OAHSA | SMPDB, HMDB | 11-(oleoyloxy)octadecanoic acid | SMPDB, HMDB | 11-(oleoyloxy)stearic acid | SMPDB, HMDB | oleic acid-11-hydroxystearic acid | SMPDB, HMDB | FAHFA(18:1(9Z)/11-O-18:0) | SMPDB |
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Chemical Formula | C36H68O4 |
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Average Molecular Weight | 564.936 |
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Monoisotopic Molecular Weight | 564.51176067 |
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IUPAC Name | 11-[(9Z)-octadec-9-enoyloxy]octadecanoic acid |
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Traditional Name | 11-[(9Z)-octadec-9-enoyloxy]octadecanoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC(CCCCCCC)CCCCCCCCCC(O)=O |
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InChI Identifier | InChI=1S/C36H68O4/c1-3-5-7-9-10-11-12-13-14-15-16-17-21-25-29-33-36(39)40-34(30-26-22-8-6-4-2)31-27-23-19-18-20-24-28-32-35(37)38/h13-14,34H,3-12,15-33H2,1-2H3,(H,37,38)/b14-13- |
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InChI Key | KPPODOBNUWGHGC-YPKPFQOOSA-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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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) GC-MS (1 TMS) - 70eV, Positive | splash10-00ri-7294043000-8e39b9077807beb87a08 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) GC-MS ("FAHFA(18:1(9Z)/11-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(18:1(9Z)/11-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(18:1(9Z)/11-O-18:0) 10V, Positive-QTOF | splash10-014j-0050090000-d018350991f2e6a5c9bc | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 20V, Positive-QTOF | splash10-015i-1090020000-776f00e6c677bf600d97 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 40V, Positive-QTOF | splash10-0076-4390000000-6ff54bb9ce9536f8e122 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 10V, Negative-QTOF | splash10-03di-0040090000-87d07df429bbc40b3125 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 20V, Negative-QTOF | splash10-01pk-0090040000-615bc0590f2e567bf5df | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 40V, Negative-QTOF | splash10-0a5d-5190000000-9dd031595315b6864ff0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 10V, Negative-QTOF | splash10-03di-0000090000-d0c7b05779e130b6f9f3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 20V, Negative-QTOF | splash10-03di-0000090000-d0c7b05779e130b6f9f3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/11-O-18:0) 40V, Negative-QTOF | splash10-03sk-0090030000-de277e22ab717964c88b | 2021-09-23 | Wishart Lab | View Spectrum |
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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 ]
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