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 16:34:04 UTC |
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Update Date | 2022-11-30 19:24:25 UTC |
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HMDB ID | HMDB0112169 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) |
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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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)), in particular, is formed from the condensation of the carboxy group of docosahexaenoic acid (DHA) with the hydroxy group of 9-hydroxyoctadecadienoic acid. It is alternatively named 9-DHAHLA since it is the 9-hydroxy isomer of the DHAHLA (docosahexaenoic acid-hydroxylinoleic acid) family. |
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Structure | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCC(=O)OC(CCCCCCCC(O)=O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCC InChI=1S/C40H62O4/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-20-21-22-24-29-33-37-40(43)44-38(34-30-26-23-10-8-6-4-2)35-31-27-25-28-32-36-39(41)42/h5,7,11-12,14-15,17-18,20-21,23-24,26,29-30,34,38H,3-4,6,8-10,13,16,19,22,25,27-28,31-33,35-37H2,1-2H3,(H,41,42)/b7-5-,12-11-,15-14-,18-17-,21-20-,26-23-,29-24-,34-30+ |
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Synonyms | Value | Source |
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(10E,12Z)-9-[(7Z,10Z,13Z,16Z,19Z)-Docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-10,12-dienoate | Generator | FAHFA(22:6/9-O-18:2) | SMPDB, HMDB | 9-DHAHLA | SMPDB, HMDB | 9-(docosahexaenoyloxy)octadecadienoic acid | SMPDB, HMDB | docosahexaenoic acid-9-hydroxylinoleic acid | SMPDB, HMDB | FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) | SMPDB |
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Chemical Formula | C40H62O4 |
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Average Molecular Weight | 606.932 |
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Monoisotopic Molecular Weight | 606.464810476 |
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IUPAC Name | (10E,12Z)-9-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-10,12-dienoic acid |
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Traditional Name | (10E,12Z)-9-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]octadeca-10,12-dienoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCC(=O)OC(CCCCCCCC(O)=O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCC |
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InChI Identifier | InChI=1S/C40H62O4/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-20-21-22-24-29-33-37-40(43)44-38(34-30-26-23-10-8-6-4-2)35-31-27-25-28-32-36-39(41)42/h5,7,11-12,14-15,17-18,20-21,23-24,26,29-30,34,38H,3-4,6,8-10,13,16,19,22,25,27-28,31-33,35-37H2,1-2H3,(H,41,42)/b7-5-,12-11-,15-14-,18-17-,21-20-,26-23-,29-24-,34-30+ |
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InChI Key | SIGOREIAIFQGQJ-HCMNWMSLSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. |
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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 | Lineolic acids and derivatives |
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Direct Parent | Lineolic acids and derivatives |
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Alternative Parents | |
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Substituents | - Octadecanoid
- Long-chain fatty acid
- Fatty acid ester
- Unsaturated fatty acid
- 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 | 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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCC(=O)OC(CCCCCCCC(O)=O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCC | 6763.5 | Standard polar | 33892256 | FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCC(=O)OC(CCCCCCCC(O)=O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCC | 4143.4 | Standard non polar | 33892256 | FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) | [H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCC(=O)OC(CCCCCCCC(O)=O)C(\[H])=C(/[H])\C(\[H])=C(\[H])CCCCC | 4517.6 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)),1TMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC=CCCC(=O)OC(/C=C/C=C\CCCCC)CCCCCCCC(=O)O[Si](C)(C)C | 4541.0 | Semi standard non polar | 33892256 | FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)),1TBDMS,isomer #1 | CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC=CCCC(=O)OC(/C=C/C=C\CCCCC)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C | 4778.1 | Semi standard non polar | 33892256 |
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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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) GC-MS (1 TMS) - 70eV, Positive | splash10-0ik9-6469205000-f2e70cf6b352920f6ae8 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) GC-MS ("FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)),1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-20 | 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 10V, Positive-QTOF | splash10-01p9-0052092000-58b144672debbf24b6d8 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 20V, Positive-QTOF | splash10-03fr-0192130000-565d3d7b1d37c92e5b14 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 40V, Positive-QTOF | splash10-00lu-3191020000-daabe2b4fa8b66ace9fc | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 10V, Negative-QTOF | splash10-0a4i-0042039000-2e7cdba0cedbaf0568f3 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 20V, Negative-QTOF | splash10-0a6s-0094022000-2aec1ae5200d44d9d5ce | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 40V, Negative-QTOF | splash10-0a6v-5292000000-d60f9a55da223ac015d0 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 10V, Negative-QTOF | splash10-0a4i-0000009000-cb60f89fb1c53ba97586 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 20V, Negative-QTOF | splash10-0a4i-0000009000-cb60f89fb1c53ba97586 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/9-O-18:2(10E,12Z)) 40V, Negative-QTOF | splash10-0bdk-0094004000-82b577cb2bcb62c380e5 | 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 ]
- Kuda O, Brezinova M, Rombaldova M, Slavikova B, Posta M, Beier P, Janovska P, Veleba J, Kopecky J Jr, Kudova E, Pelikanova T, Kopecky J: Docosahexaenoic Acid-Derived Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) With Anti-inflammatory Properties. Diabetes. 2016 Sep;65(9):2580-90. doi: 10.2337/db16-0385. Epub 2016 Jun 16. [PubMed:27313314 ]
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