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 19:50:43 UTC |
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Update Date | 2022-03-07 02:54:16 UTC |
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HMDB ID | HMDB0034917 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Xanthohumol E |
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Description | Xanthohumol E belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, xanthohumol e is considered to be a flavonoid. Xanthohumol E has been detected, but not quantified in, alcoholic beverages. This could make xanthohumol e a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthohumol E. |
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Structure | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O InChI=1S/C25H26O5/c1-15(2)5-11-18-22(28)19-13-14-25(3,4)30-24(19)21(23(18)29)20(27)12-8-16-6-9-17(26)10-7-16/h5-10,12-14,26,28-29H,11H2,1-4H3/b12-8+ |
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Synonyms | Not Available |
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Chemical Formula | C25H26O5 |
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Average Molecular Weight | 406.4709 |
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Monoisotopic Molecular Weight | 406.178023942 |
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IUPAC Name | (2E)-1-[5,7-dihydroxy-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-2H-chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one |
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Traditional Name | xanthohumol E |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)\C=C\C2=CC=C(O)C=C2)=C1O |
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InChI Identifier | InChI=1S/C25H26O5/c1-15(2)5-11-18-22(28)19-13-14-25(3,4)30-24(19)21(23(18)29)20(27)12-8-16-6-9-17(26)10-7-16/h5-10,12-14,26,28-29H,11H2,1-4H3/b12-8+ |
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InChI Key | KRZGSPKDWYNTHE-XYOKQWHBSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Linear 1,3-diarylpropanoids |
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Sub Class | Chalcones and dihydrochalcones |
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Direct Parent | 3-prenylated chalcones |
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Alternative Parents | |
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Substituents | - 3-prenylated chalcone
- 2'-hydroxychalcone
- Hydroxycinnamic acid or derivatives
- 2,2-dimethyl-1-benzopyran
- Benzopyran
- 1-benzopyran
- Styrene
- Aryl ketone
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Acryloyl-group
- Enone
- Vinylogous acid
- Alpha,beta-unsaturated ketone
- Ketone
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Xanthohumol E,1TMS,isomer #1 | CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C | 3394.0 | Semi standard non polar | 33892256 | Xanthohumol E,1TMS,isomer #2 | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O | 3399.4 | Semi standard non polar | 33892256 | Xanthohumol E,1TMS,isomer #3 | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C | 3452.5 | Semi standard non polar | 33892256 | Xanthohumol E,2TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C | 3379.8 | Semi standard non polar | 33892256 | Xanthohumol E,2TMS,isomer #2 | CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C | 3349.0 | Semi standard non polar | 33892256 | Xanthohumol E,2TMS,isomer #3 | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C | 3362.5 | Semi standard non polar | 33892256 | Xanthohumol E,3TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2)=C1O[Si](C)(C)C | 3386.9 | Semi standard non polar | 33892256 | Xanthohumol E,1TBDMS,isomer #1 | CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C(C)(C)C | 3640.4 | Semi standard non polar | 33892256 | Xanthohumol E,1TBDMS,isomer #2 | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O | 3646.1 | Semi standard non polar | 33892256 | Xanthohumol E,1TBDMS,isomer #3 | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C | 3706.6 | Semi standard non polar | 33892256 | Xanthohumol E,2TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O[Si](C)(C)C(C)(C)C | 3881.4 | Semi standard non polar | 33892256 | Xanthohumol E,2TBDMS,isomer #2 | CC(C)=CCC1=C(O)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C2OC(C)(C)C=CC2=C1O[Si](C)(C)C(C)(C)C | 3892.1 | Semi standard non polar | 33892256 | Xanthohumol E,2TBDMS,isomer #3 | CC(C)=CCC1=C(O)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C | 3876.8 | Semi standard non polar | 33892256 | Xanthohumol E,3TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C2=C(OC(C)(C)C=C2)C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)=C1O[Si](C)(C)C(C)(C)C | 4084.7 | 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 - Xanthohumol E GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-3419000000-6b57ba67f36b750282ff | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Xanthohumol E GC-MS (3 TMS) - 70eV, Positive | splash10-0a4i-2100039000-e2df2595710013827aed | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Xanthohumol E 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 - Xanthohumol E 10V, Positive-QTOF | splash10-0a4i-1228900000-be84c08d3627bfb84386 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Positive-QTOF | splash10-05mt-3449100000-1308efc4968142069b76 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Positive-QTOF | splash10-066r-7693000000-f36e5b6f6382d4fc2afb | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 10V, Negative-QTOF | splash10-0a4i-0131900000-510a93d327c759852a6d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Negative-QTOF | splash10-0a4i-0692300000-e75638ba22e4a154b3cc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Negative-QTOF | splash10-00bd-0952000000-b5d65dccff1b1660516f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 10V, Positive-QTOF | splash10-0udi-0009300000-8744eba2a46dd5076742 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Positive-QTOF | splash10-001i-0094200000-e4eac9c491fed44bc73d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Positive-QTOF | splash10-00ls-0189000000-3dce236f23c346862e80 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 10V, Negative-QTOF | splash10-0a4i-0000900000-7b5974fd53d3ffdb29ad | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 20V, Negative-QTOF | splash10-0a4i-0163900000-1b15da60ece2daff6787 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Xanthohumol E 40V, Negative-QTOF | splash10-014i-5973000000-d1f27b7331f17adc1166 | 2021-09-25 | Wishart Lab | View Spectrum |
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