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 22:28:35 UTC |
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Update Date | 2022-03-07 02:55:14 UTC |
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HMDB ID | HMDB0037235 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Quassinol |
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Description | Quassinol, also known as bisnorquassin, belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Quassinol is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC1CC(=O)C2(O)OC3C4C2(C)C1CC1OC(=O)C=C(C(C)=C3O)C41C InChI=1S/C20H24O6/c1-8-5-12(21)20(24)19(4)10(8)6-13-18(3)11(7-14(22)25-13)9(2)15(23)16(26-20)17(18)19/h7-8,10,13,16-17,23-24H,5-6H2,1-4H3 |
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Synonyms | Value | Source |
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Bisnorquassin | HMDB |
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Chemical Formula | C20H24O6 |
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Average Molecular Weight | 360.401 |
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Monoisotopic Molecular Weight | 360.1572885 |
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IUPAC Name | 5,8-dihydroxy-2,9,15,17-tetramethyl-6,13-dioxapentacyclo[12.3.1.0⁵,¹⁷.0⁷,¹⁶.0¹⁰,¹⁵]octadeca-8,10-diene-4,12-dione |
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Traditional Name | 5,8-dihydroxy-2,9,15,17-tetramethyl-6,13-dioxapentacyclo[12.3.1.0⁵,¹⁷.0⁷,¹⁶.0¹⁰,¹⁵]octadeca-8,10-diene-4,12-dione |
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CAS Registry Number | 21018-87-1 |
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SMILES | CC1CC(=O)C2(O)OC3C4C2(C)C1CC1OC(=O)C=C(C(C)=C3O)C41C |
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InChI Identifier | InChI=1S/C20H24O6/c1-8-5-12(21)20(24)19(4)10(8)6-13-18(3)11(7-14(22)25-13)9(2)15(23)16(26-20)17(18)19/h7-8,10,13,16-17,23-24H,5-6H2,1-4H3 |
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InChI Key | WKNPIBKVHHVICI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. |
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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 | Quassinoids |
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Alternative Parents | |
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Substituents | - C-20 quassinoid skeleton
- Quassinoid
- Naphthopyran
- Naphthalene
- Dihydropyranone
- Pyran
- Cyclic alcohol
- Alpha,beta-unsaturated carboxylic ester
- Tetrahydrofuran
- Enoate ester
- Lactone
- Ketone
- Hemiacetal
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Enol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- 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 | 258 - 260 °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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Quassinol,1TMS,isomer #1 | CC1=C(O)C2OC3(O[Si](C)(C)C)C(=O)CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2916.8 | Semi standard non polar | 33892256 | Quassinol,1TMS,isomer #2 | CC1=C(O[Si](C)(C)C)C2OC3(O)C(=O)CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2954.7 | Semi standard non polar | 33892256 | Quassinol,1TMS,isomer #3 | CC1=C(O)C2OC3(O)C(O[Si](C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2882.4 | Semi standard non polar | 33892256 | Quassinol,2TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C2OC3(O[Si](C)(C)C)C(=O)CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2962.2 | Semi standard non polar | 33892256 | Quassinol,2TMS,isomer #2 | CC1=C(O)C2OC3(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2857.8 | Semi standard non polar | 33892256 | Quassinol,2TMS,isomer #3 | CC1=C(O[Si](C)(C)C)C2OC3(O)C(O[Si](C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2901.8 | Semi standard non polar | 33892256 | Quassinol,3TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C2OC3(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2893.6 | Semi standard non polar | 33892256 | Quassinol,3TMS,isomer #1 | CC1=C(O[Si](C)(C)C)C2OC3(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 2861.1 | Standard non polar | 33892256 | Quassinol,1TBDMS,isomer #1 | CC1=C(O)C2OC3(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3168.8 | Semi standard non polar | 33892256 | Quassinol,1TBDMS,isomer #2 | CC1=C(O[Si](C)(C)C(C)(C)C)C2OC3(O)C(=O)CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3207.9 | Semi standard non polar | 33892256 | Quassinol,1TBDMS,isomer #3 | CC1=C(O)C2OC3(O)C(O[Si](C)(C)C(C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3135.2 | Semi standard non polar | 33892256 | Quassinol,2TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C2OC3(O[Si](C)(C)C(C)(C)C)C(=O)CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3462.5 | Semi standard non polar | 33892256 | Quassinol,2TBDMS,isomer #2 | CC1=C(O)C2OC3(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3360.9 | Semi standard non polar | 33892256 | Quassinol,2TBDMS,isomer #3 | CC1=C(O[Si](C)(C)C(C)(C)C)C2OC3(O)C(O[Si](C)(C)C(C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3406.6 | Semi standard non polar | 33892256 | Quassinol,3TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C2OC3(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3607.5 | Semi standard non polar | 33892256 | Quassinol,3TBDMS,isomer #1 | CC1=C(O[Si](C)(C)C(C)(C)C)C2OC3(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC(C)C4CC5OC(=O)C=C1C5(C)C2C43C | 3429.6 | 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 - Quassinol GC-MS (Non-derivatized) - 70eV, Positive | splash10-00kf-9005000000-acaa165a121140aa7d49 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Quassinol GC-MS (2 TMS) - 70eV, Positive | splash10-010c-9000700000-0042a653c5daba1bbfae | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Quassinol 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 - Quassinol 10V, Positive-QTOF | splash10-0ik9-0009000000-18a56bd4b5f912a7ebe9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 20V, Positive-QTOF | splash10-0wmi-0019000000-6ff9522e692eb16b60e1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 40V, Positive-QTOF | splash10-0006-9023000000-d5fcc0c203860d251663 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 10V, Negative-QTOF | splash10-0aor-0009000000-cc9cc9fe9fc7faa50f83 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 20V, Negative-QTOF | splash10-0aor-0009000000-5e6b0fe8b634b0fad5fb | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 40V, Negative-QTOF | splash10-066v-6094000000-925320bfb648d5fe4d68 | 2016-08-04 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 10V, Negative-QTOF | splash10-0a4i-0009000000-d6fe99be8012d24cd96c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 20V, Negative-QTOF | splash10-0a4i-0009000000-02d8dcc6f2e6225173f2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 40V, Negative-QTOF | splash10-0a4i-0009000000-2bf57022a871e5d8c38f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 10V, Positive-QTOF | splash10-03di-0009000000-6072fd31342288e0ad83 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 20V, Positive-QTOF | splash10-03dl-0019000000-e7b1c2ea89e1171d2075 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Quassinol 40V, Positive-QTOF | splash10-03di-0019000000-32977a6392faca67f3c7 | 2021-09-23 | Wishart Lab | View Spectrum |
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