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 17:30:59 UTC |
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Update Date | 2022-03-07 02:52:11 UTC |
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HMDB ID | HMDB0029531 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (S)-4',7-Dihydroxy-3',8-diprenylflavanone |
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Description | (S)-4',7-Dihydroxy-3',8-diprenylflavanone, also known as glabrol, belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, (S)-4',7-dihydroxy-3',8-diprenylflavanone is considered to be a flavonoid. Based on a literature review very few articles have been published on (S)-4',7-Dihydroxy-3',8-diprenylflavanone. |
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Structure | CC(C)=CCC1=CC(=CC=C1O)C1CC(=O)C2=C(O1)C(CC=C(C)C)=C(O)C=C2 InChI=1S/C25H28O4/c1-15(2)5-7-17-13-18(8-11-21(17)26)24-14-23(28)20-10-12-22(27)19(25(20)29-24)9-6-16(3)4/h5-6,8,10-13,24,26-27H,7,9,14H2,1-4H3 |
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Synonyms | |
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Chemical Formula | C25H28O4 |
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Average Molecular Weight | 392.4874 |
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Monoisotopic Molecular Weight | 392.198759384 |
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IUPAC Name | 7-hydroxy-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one |
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Traditional Name | glabrol |
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CAS Registry Number | 59870-65-4 |
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SMILES | CC(C)=CCC1=CC(=CC=C1O)C1CC(=O)C2=C(O1)C(CC=C(C)C)=C(O)C=C2 |
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InChI Identifier | InChI=1S/C25H28O4/c1-15(2)5-7-17-13-18(8-11-21(17)26)24-14-23(28)20-10-12-22(27)19(25(20)29-24)9-6-16(3)4/h5-6,8,10-13,24,26-27H,7,9,14H2,1-4H3 |
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InChI Key | CUFAXDWQDQQKFF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavans |
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Direct Parent | 8-prenylated flavanones |
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Alternative Parents | |
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Substituents | - 3'-prenylated flavanone
- 8-prenylated flavanone
- 3'-prenylated flavan
- 4'-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavanone
- Hydroxyflavonoid
- Chromone
- Chromane
- Benzopyran
- 1-benzopyran
- Aryl alkyl ketone
- Aryl ketone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Ketone
- Organoheterocyclic compound
- Ether
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- 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 | Not Available |
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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 | 90 °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 | |
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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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(S)-4',7-Dihydroxy-3',8-diprenylflavanone,1TMS,isomer #1 | CC(C)=CCC1=CC(C2CC(=O)C3=CC=C(O)C(CC=C(C)C)=C3O2)=CC=C1O[Si](C)(C)C | 3393.1 | Semi standard non polar | 33892256 | (S)-4',7-Dihydroxy-3',8-diprenylflavanone,1TMS,isomer #2 | CC(C)=CCC1=CC(C2CC(=O)C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O2)=CC=C1O | 3383.9 | Semi standard non polar | 33892256 | (S)-4',7-Dihydroxy-3',8-diprenylflavanone,2TMS,isomer #1 | CC(C)=CCC1=CC(C2CC(=O)C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O2)=CC=C1O[Si](C)(C)C | 3310.0 | Semi standard non polar | 33892256 | (S)-4',7-Dihydroxy-3',8-diprenylflavanone,1TBDMS,isomer #1 | CC(C)=CCC1=CC(C2CC(=O)C3=CC=C(O)C(CC=C(C)C)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C | 3627.6 | Semi standard non polar | 33892256 | (S)-4',7-Dihydroxy-3',8-diprenylflavanone,1TBDMS,isomer #2 | CC(C)=CCC1=CC(C2CC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O2)=CC=C1O | 3605.8 | Semi standard non polar | 33892256 | (S)-4',7-Dihydroxy-3',8-diprenylflavanone,2TBDMS,isomer #1 | CC(C)=CCC1=CC(C2CC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C | 3696.6 | 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 - (S)-4',7-Dihydroxy-3',8-diprenylflavanone GC-MS (Non-derivatized) - 70eV, Positive | splash10-004u-2209000000-a1cfa36a9456be757361 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone GC-MS (2 TMS) - 70eV, Positive | splash10-00di-2010590000-21d3e00a7792a47594b3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 6V, Positive-QTOF | splash10-000f-0739000000-6d9c84b8cfb29b9146f9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 6V, Negative-QTOF | splash10-000f-0739000000-7c26752e08c5578b3bf3 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 10V, Positive-QTOF | splash10-0006-0219000000-1a450b93cdab835ce016 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 20V, Positive-QTOF | splash10-000i-2739000000-2f9893d6fb4bc2ae2fcd | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 40V, Positive-QTOF | splash10-014i-5910000000-eddd1957e1e0c9aaa290 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 10V, Negative-QTOF | splash10-0006-0009000000-d110834225487bd44c93 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 20V, Negative-QTOF | splash10-0006-0129000000-8f81c386e354c7ce082c | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 40V, Negative-QTOF | splash10-01ri-0912000000-1f8938bea8663af5448b | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 10V, Positive-QTOF | splash10-0006-0009000000-aafba7ce7fb7e4a34ccc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 20V, Positive-QTOF | splash10-0a4m-0496000000-44fb133aec0f1502978e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 40V, Positive-QTOF | splash10-0a4i-0390000000-0e32b414140d76805346 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 10V, Negative-QTOF | splash10-0006-0009000000-a64f64466282be014e43 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 20V, Negative-QTOF | splash10-0f6x-0079000000-b12efc0aa3392f976163 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (S)-4',7-Dihydroxy-3',8-diprenylflavanone 40V, Negative-QTOF | splash10-000i-0930000000-62093a9a302ea28ddb12 | 2021-09-24 | Wishart Lab | View Spectrum |
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