Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 21:51:23 UTC |
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Update Date | 2022-03-07 02:55:01 UTC |
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HMDB ID | HMDB0036690 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Epinobilin |
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Description | 3-Epinobilin belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on 3-Epinobilin. |
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Structure | [H]\C(C)=C(/C)C(=O)OC1C\C(C)=C([H])\CC(O)\C(C)=C([H])\C2OC(=O)C(=C)C12 InChI=1S/C20H26O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,15-18,21H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10+ |
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Synonyms | Value | Source |
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9-Hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoic acid | HMDB |
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Chemical Formula | C20H26O5 |
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Average Molecular Weight | 346.423 |
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Monoisotopic Molecular Weight | 346.178023937 |
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IUPAC Name | 9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate |
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Traditional Name | 9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C\C=C(\C)C(=O)OC1C\C(C)=C\CC(O)\C(C)=C\C2OC(=O)C(=C)C12 |
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InChI Identifier | InChI=1S/C20H26O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,15-18,21H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10+ |
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InChI Key | QFINJHBXXJQKPB-QLDBJWRKSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. |
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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 | Terpene lactones |
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Direct Parent | Germacranolides and derivatives |
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Alternative Parents | |
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Substituents | - Germacranolide
- Germacrane sesquiterpenoid
- Sesquiterpenoid
- Fatty acid ester
- Dicarboxylic acid or derivatives
- Gamma butyrolactone
- Fatty acyl
- Alpha,beta-unsaturated carboxylic ester
- Tetrahydrofuran
- Enoate ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | 137 °C | 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 IndicesUnderivatizedDerivatized | Show more...
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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 - 3-Epinobilin GC-MS (Non-derivatized) - 70eV, Positive | splash10-053r-9022000000-40b15452d12f24aa44ab | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Epinobilin GC-MS (1 TMS) - 70eV, Positive | splash10-053r-9001000000-bd362f2d4d8527669e25 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Epinobilin 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 - 3-Epinobilin 10V, Positive-QTOF | splash10-002b-2049000000-4ada8c8f5b1aa75552bf | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Positive-QTOF | splash10-057j-9182000000-93f1c8852bfe5265a632 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Positive-QTOF | splash10-100r-9220000000-09cce363075ad08956ed | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 10V, Negative-QTOF | splash10-0002-0029000000-dc8b56399c4a82daee30 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Negative-QTOF | splash10-0002-5059000000-0ae00cdbb81c3908b3f6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Negative-QTOF | splash10-05mt-9640000000-7f88f9d74127f2a45e6e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 10V, Positive-QTOF | splash10-0002-0090000000-532ee58b0a32582e7047 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Positive-QTOF | splash10-004i-0090000000-196551c9eb839176ef5a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Positive-QTOF | splash10-0032-2090000000-07e2a081ad01a389a6bd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 10V, Negative-QTOF | splash10-0002-9076000000-1d4096873c48c96b380e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Negative-QTOF | splash10-0002-9050000000-4e8ea669f117f307e35a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Negative-QTOF | splash10-0pdj-9070000000-7966e503f790225b8675 | 2021-09-23 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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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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| Not Available |
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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 | FDB015621 |
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KNApSAcK ID | C00003339 |
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Chemspider ID | 35014202 |
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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 | 131752037 |
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PDB ID | Not Available |
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ChEBI ID | 175404 |
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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 ]
- (). 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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