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 20:09:21 UTC |
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Update Date | 2022-03-07 02:54:24 UTC |
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HMDB ID | HMDB0035206 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Bakkenolide B |
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Description | Bakkenolide B, also known as fukinolide or petasilide, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Bakkenolide B. |
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Structure | [H][C@@]12[C@@H](OC(C)=O)[C@@]3(C[C@]1(C)[C@@H](C)CC[C@@H]2OC(=O)C(\C)=C\C)C(=C)COC3=O InChI=1S/C22H30O6/c1-7-12(2)19(24)28-16-9-8-13(3)21(6)11-22(14(4)10-26-20(22)25)18(17(16)21)27-15(5)23/h7,13,16-18H,4,8-11H2,1-3,5-6H3/b12-7+/t13-,16-,17+,18+,21+,22+/m0/s1 |
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Synonyms | Value | Source |
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Fukinolide | HMDB | Petasilide | HMDB | (2R,3R,3AR,4S,7S,7ar)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl (2E)-2-methylbut-2-enoic acid | HMDB | Bakkenolide-b | HMDB |
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Chemical Formula | C22H30O6 |
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Average Molecular Weight | 390.47 |
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Monoisotopic Molecular Weight | 390.204238692 |
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IUPAC Name | (1R,2R,3aR,4S,7S,7aR)-1-(acetyloxy)-3a,4-dimethyl-4'-methylidene-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-7-yl (2E)-2-methylbut-2-enoate |
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Traditional Name | (2R,3R,3aR,4S,7S,7aR)-3-(acetyloxy)-7,7a-dimethyl-4'-methylidene-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl (2E)-2-methylbut-2-enoate |
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CAS Registry Number | 18455-98-6 |
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SMILES | [H][C@@]12[C@@H](OC(C)=O)[C@@]3(C[C@]1(C)[C@@H](C)CC[C@@H]2OC(=O)C(\C)=C\C)C(=C)COC3=O |
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InChI Identifier | InChI=1S/C22H30O6/c1-7-12(2)19(24)28-16-9-8-13(3)21(6)11-22(14(4)10-26-20(22)25)18(17(16)21)27-15(5)23/h7,13,16-18H,4,8-11H2,1-3,5-6H3/b12-7+/t13-,16-,17+,18+,21+,22+/m0/s1 |
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InChI Key | AVAGQVZSHJYDED-NWAIQIOLSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone 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 | Terpene lactones |
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Alternative Parents | |
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Substituents | - Terpene lactone
- Sesquiterpenoid
- Tricarboxylic acid or derivatives
- Fatty acid ester
- Gamma butyrolactone
- Fatty acyl
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Lactone
- Carboxylic acid ester
- Oxacycle
- Carboxylic acid derivative
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- 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 | 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 | 101 - 102 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.71 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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 IndicesUnderivatized |
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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 - Bakkenolide B GC-MS (Non-derivatized) - 70eV, Positive | splash10-057i-8095000000-771595dfb645a7bc49bb | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Bakkenolide B GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Bakkenolide B 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 - Bakkenolide B 10V, Positive-QTOF | splash10-000x-2029000000-b946949ebaa41fcb4430 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 20V, Positive-QTOF | splash10-001l-9054000000-e54f23ffb0dd52d51985 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 40V, Positive-QTOF | splash10-001i-9010000000-0a0736f26fda60c1efae | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 10V, Negative-QTOF | splash10-000j-1009000000-1096244ad87ddf1b063e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 20V, Negative-QTOF | splash10-052b-6029000000-b518066daffc7894734d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 40V, Negative-QTOF | splash10-052e-9074000000-faf9b679f7fd4608bb8d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 10V, Positive-QTOF | splash10-0006-0039000000-65cceab66715a09603d2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 20V, Positive-QTOF | splash10-00rx-0291000000-0b32115941b61fa362ad | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 40V, Positive-QTOF | splash10-0a4i-9220000000-ce528b7a4bc4ec8b75c9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 10V, Negative-QTOF | splash10-0a4r-9004000000-df21f6d4146839581506 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 20V, Negative-QTOF | splash10-0a4i-9052000000-d0695c967ff9ee9474a7 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Bakkenolide B 40V, Negative-QTOF | splash10-0a4i-9000000000-e8ed178dee360c30d806 | 2021-09-22 | Wishart Lab | View Spectrum |
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