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 17:35:01 UTC |
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Update Date | 2022-03-07 02:52:26 UTC |
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HMDB ID | HMDB0030138 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Adhumulone |
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Description | Adhumulone belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. Adhumulone is a bitter tasting compound. Adhumulone has been detected, but not quantified in, several different foods, such as alcoholic beverages, red tea, green tea, teas (Camellia sinensis), and herbal tea. This could make adhumulone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Adhumulone. |
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Structure | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O InChI=1S/C21H30O5/c1-7-14(6)17(22)16-18(23)15(9-8-12(2)3)19(24)21(26,20(16)25)11-10-13(4)5/h8,10,14-15,23,26H,7,9,11H2,1-6H3 |
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Synonyms | Not Available |
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Chemical Formula | C21H30O5 |
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Average Molecular Weight | 362.4599 |
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Monoisotopic Molecular Weight | 362.20932407 |
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IUPAC Name | 2,5-dihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione |
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Traditional Name | 2,5-dihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione |
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CAS Registry Number | 28374-89-2 |
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SMILES | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O |
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InChI Identifier | InChI=1S/C21H30O5/c1-7-14(6)17(22)16-18(23)15(9-8-12(2)3)19(24)21(26,20(16)25)11-10-13(4)5/h8,10,14-15,23,26H,7,9,11H2,1-6H3 |
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InChI Key | VISQWZWNDCYFMY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | M-benzoquinones |
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Alternative Parents | |
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Substituents | - M-benzoquinone
- Cyclohexenone
- Acyloin
- Vinylogous acid
- Tertiary alcohol
- Enol
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | |
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Disposition | |
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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 | |
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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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Adhumulone,1TMS,isomer #1 | CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O | 2482.1 | Semi standard non polar | 33892256 | Adhumulone,1TMS,isomer #2 | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2458.2 | Semi standard non polar | 33892256 | Adhumulone,1TMS,isomer #3 | CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O | 2538.8 | Semi standard non polar | 33892256 | Adhumulone,1TMS,isomer #4 | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O | 2443.9 | Semi standard non polar | 33892256 | Adhumulone,2TMS,isomer #1 | CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2556.1 | Semi standard non polar | 33892256 | Adhumulone,2TMS,isomer #2 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O | 2593.4 | Semi standard non polar | 33892256 | Adhumulone,2TMS,isomer #3 | CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O | 2501.4 | Semi standard non polar | 33892256 | Adhumulone,2TMS,isomer #4 | CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2576.5 | Semi standard non polar | 33892256 | Adhumulone,2TMS,isomer #5 | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2518.8 | Semi standard non polar | 33892256 | Adhumulone,2TMS,isomer #6 | CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O | 2549.8 | Semi standard non polar | 33892256 | Adhumulone,3TMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2642.6 | Semi standard non polar | 33892256 | Adhumulone,3TMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2600.3 | Standard non polar | 33892256 | Adhumulone,3TMS,isomer #2 | CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2536.7 | Semi standard non polar | 33892256 | Adhumulone,3TMS,isomer #2 | CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2531.8 | Standard non polar | 33892256 | Adhumulone,3TMS,isomer #3 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O | 2582.3 | Semi standard non polar | 33892256 | Adhumulone,3TMS,isomer #3 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O | 2525.1 | Standard non polar | 33892256 | Adhumulone,3TMS,isomer #4 | CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2612.8 | Semi standard non polar | 33892256 | Adhumulone,3TMS,isomer #4 | CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2597.6 | Standard non polar | 33892256 | Adhumulone,4TMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2617.8 | Semi standard non polar | 33892256 | Adhumulone,4TMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O | 2636.8 | Standard non polar | 33892256 | Adhumulone,1TBDMS,isomer #1 | CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O | 2728.2 | Semi standard non polar | 33892256 | Adhumulone,1TBDMS,isomer #2 | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 2706.7 | Semi standard non polar | 33892256 | Adhumulone,1TBDMS,isomer #3 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O | 2781.7 | Semi standard non polar | 33892256 | Adhumulone,1TBDMS,isomer #4 | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O | 2707.9 | Semi standard non polar | 33892256 | Adhumulone,2TBDMS,isomer #1 | CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 2994.9 | Semi standard non polar | 33892256 | Adhumulone,2TBDMS,isomer #2 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O | 3051.1 | Semi standard non polar | 33892256 | Adhumulone,2TBDMS,isomer #3 | CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O | 2974.0 | Semi standard non polar | 33892256 | Adhumulone,2TBDMS,isomer #4 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3030.0 | Semi standard non polar | 33892256 | Adhumulone,2TBDMS,isomer #5 | CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 2984.8 | Semi standard non polar | 33892256 | Adhumulone,2TBDMS,isomer #6 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O | 3020.2 | Semi standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3292.6 | Semi standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3138.1 | Standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #2 | CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3204.7 | Semi standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #2 | CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3052.7 | Standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #3 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O | 3245.7 | Semi standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #3 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O | 3035.6 | Standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #4 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3258.9 | Semi standard non polar | 33892256 | Adhumulone,3TBDMS,isomer #4 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3132.7 | Standard non polar | 33892256 | Adhumulone,4TBDMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3441.1 | Semi standard non polar | 33892256 | Adhumulone,4TBDMS,isomer #1 | CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O | 3268.9 | 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 - Adhumulone GC-MS (Non-derivatized) - 70eV, Positive | splash10-052n-5597000000-982154af1d40cda1c66a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Adhumulone GC-MS (2 TMS) - 70eV, Positive | splash10-0006-5221900000-8d7c8a85db2f88cd5ff2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Adhumulone 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 - Adhumulone 10V, Positive-QTOF | splash10-03di-2019000000-2aa507d821fc7ffbdf04 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 20V, Positive-QTOF | splash10-0ap1-8059000000-a61f9ba0afd3d2edc74e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 40V, Positive-QTOF | splash10-05o0-9010000000-8427a5e736604f3ed46a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 10V, Negative-QTOF | splash10-03di-0169000000-0a24450480607a9bb301 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 20V, Negative-QTOF | splash10-004i-4293000000-1934c0234b620a011f0c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 40V, Negative-QTOF | splash10-0092-9662000000-78a90e3f9bbd37286eb7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 10V, Negative-QTOF | splash10-03di-0019000000-e97810a92d4148f645b8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 20V, Negative-QTOF | splash10-03di-0359000000-a53af1b57ba359cce8a2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 40V, Negative-QTOF | splash10-004i-7932000000-cb58dcffcbfa7664f791 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 10V, Positive-QTOF | splash10-03di-0009000000-7680edf2c7b3883c08d3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 20V, Positive-QTOF | splash10-03di-2669000000-888dea72aeb40f693d80 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Adhumulone 40V, Positive-QTOF | splash10-053r-9341000000-08c28f74f14d434ada9b | 2021-09-25 | Wishart Lab | View Spectrum |
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