Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 02:34:30 UTC |
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Update Date | 2022-03-07 02:56:49 UTC |
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HMDB ID | HMDB0040953 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tussilagone |
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Description | Tussilagone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Tussilagone. |
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Structure | CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C InChI=1S/C23H34O5/c1-8-13(4)9-21(26)28-20-11-17(12(2)3)23-18(14(20)5)10-19(25)22(23)15(6)27-16(7)24/h9,12,15,17-18,20,22-23H,5,8,10-11H2,1-4,6-7H3/b13-9+ |
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Synonyms | Value | Source |
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Farfaratin | HMDB | 1-[1-(Acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoic acid | Generator | (7R,14R)-14-Acetoxy-7-((2'e)-3'-methylpent-2'-enoyloxy)-oplopanone | MeSH | 14-Acetoxy-7-(3'-ethylcrotonoyloxy)-notonipetranone | MeSH | 14-Acetoxy-7b-(3'-ethylcrotonoyloxy)-notonipetranone | MeSH | Tussilagone | MeSH | 9a-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate | Generator | 9a-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acid | Generator | 9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acid | Generator | 9Α-(3-methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate | Generator | 9Α-(3-methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acid | Generator |
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Chemical Formula | C23H34O5 |
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Average Molecular Weight | 390.5131 |
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Monoisotopic Molecular Weight | 390.240624198 |
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IUPAC Name | 1-[1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate |
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Traditional Name | 1-[1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate |
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CAS Registry Number | 104012-37-5 |
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SMILES | CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C |
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InChI Identifier | InChI=1S/C23H34O5/c1-8-13(4)9-21(26)28-20-11-17(12(2)3)23-18(14(20)5)10-19(25)22(23)15(6)27-16(7)24/h9,12,15,17-18,20,22-23H,5,8,10-11H2,1-4,6-7H3/b13-9+ |
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InChI Key | CFUPNMDNSQIWBB-UKTHLTGXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Sesquiterpenoid
- Oplopane sesquiterpenoid
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Fatty acyl
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Cyclic ketone
- Ketone
- Carboxylic acid ester
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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 | |
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Role | |
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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 | 100 - 101 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.089 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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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Tussilagone,1TMS,isomer #1 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C)CC12 | 2582.8 | Semi standard non polar | 33892256 | Tussilagone,1TMS,isomer #1 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C)CC12 | 2622.0 | Standard non polar | 33892256 | Tussilagone,1TMS,isomer #2 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)OC(C)=O | 2532.6 | Semi standard non polar | 33892256 | Tussilagone,1TMS,isomer #2 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)OC(C)=O | 2596.1 | Standard non polar | 33892256 | Tussilagone,1TBDMS,isomer #1 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C(C)(C)C)CC12 | 2783.2 | Semi standard non polar | 33892256 | Tussilagone,1TBDMS,isomer #1 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C(C)(C)C)CC12 | 2831.4 | Standard non polar | 33892256 | Tussilagone,1TBDMS,isomer #2 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)OC(C)=O | 2737.0 | Semi standard non polar | 33892256 | Tussilagone,1TBDMS,isomer #2 | C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)OC(C)=O | 2764.0 | 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 - Tussilagone GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-7195000000-dafd6bcde25680a7933e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tussilagone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - Tussilagone 10V, Positive-QTOF | splash10-052e-8039000000-b36cbbf403995c06f288 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 20V, Positive-QTOF | splash10-0pb9-9021000000-244d8ac8eb2ebcd7accb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 40V, Positive-QTOF | splash10-0pbi-9020000000-fac7c6b5476c989c8559 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 10V, Negative-QTOF | splash10-000m-3029000000-cc27d7bfdedf1be0fd1c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 20V, Negative-QTOF | splash10-052g-7196000000-b72b479fc0e0efe7c218 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 40V, Negative-QTOF | splash10-052e-7090000000-f0c13261c10949ebf3ba | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 10V, Positive-QTOF | splash10-002r-0090000000-b075c0a89c9622fc55ec | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 20V, Positive-QTOF | splash10-0002-0391000000-de73ab31b89043a1fcb0 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 40V, Positive-QTOF | splash10-05no-9240000000-368855e350e7563e39ec | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 10V, Negative-QTOF | splash10-001r-1093000000-78557e1f844456105034 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 20V, Negative-QTOF | splash10-0btj-6392000000-8d5ae20280d274812a16 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tussilagone 40V, Negative-QTOF | splash10-0a4i-7191000000-5e1b8f0852d951b8061c | 2021-09-25 | Wishart Lab | View Spectrum |
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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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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