Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 18:31:37 UTC |
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Updated at | 2022-09-06 18:31:37 UTC |
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NP-MRD ID | NP0235794 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (5s,6r)-5-hydroxy-6-methyl-5,6-dihydropyran-2-one |
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Description | Osmundalactone belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. (5s,6r)-5-hydroxy-6-methyl-5,6-dihydropyran-2-one is found in Angiopteris caudatiformis and Tapinella atrotomentosa. It was first documented in 2009 (PMID: 19371069). Based on a literature review a small amount of articles have been published on Osmundalactone (PMID: 32183470) (PMID: 29734648) (PMID: 22863714). |
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Structure | InChI=1S/C6H8O3/c1-4-5(7)2-3-6(8)9-4/h2-5,7H,1H3/t4-,5+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C6H8O3 |
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Average Mass | 128.1270 Da |
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Monoisotopic Mass | 128.04734 Da |
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IUPAC Name | (5S,6R)-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one |
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Traditional Name | (5S,6R)-5-hydroxy-6-methyl-5,6-dihydropyran-2-one |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1OC(=O)C=C[C@@H]1O |
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InChI Identifier | InChI=1S/C6H8O3/c1-4-5(7)2-3-6(8)9-4/h2-5,7H,1H3/t4-,5+/m1/s1 |
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InChI Key | TVDPVFPVOHCHQM-UHNVWZDZSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrans |
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Sub Class | Pyranones and derivatives |
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Direct Parent | Dihydropyranones |
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Alternative Parents | |
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Substituents | - Dihydropyranone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Lamichhane R, Pandeya PR, Lee KH, Kim SG, Devkota HP, Jung HJ: Anti-Adipogenic and Anti-Inflammatory Activities of (-)-epi-Osmundalactone and Angiopteroside from Angiopteris helferiana C.Presl. Molecules. 2020 Mar 15;25(6). pii: molecules25061337. doi: 10.3390/molecules25061337. [PubMed:32183470 ]
- Beni Z, Dekany M, Kovacs B, Csupor-Loffler B, Zomborszki ZP, Kerekes E, Szekeres A, Urban E, Hohmann J, Vanyolos A: Bioactivity-Guided Isolation of Antimicrobial and Antioxidant Metabolites from the Mushroom Tapinella atrotomentosa. Molecules. 2018 May 4;23(5). pii: molecules23051082. doi: 10.3390/molecules23051082. [PubMed:29734648 ]
- Ono M, Zhao XY, Kato K, Akita H: The asymmetric syntheses of methyl D-digitoxoside, L-oleandrose and L-cymarose from methyl sorbate, an achiral precursor. Chem Pharm Bull (Tokyo). 2012;60(8):1076-82. doi: 10.1248/cpb.c12-00308. [PubMed:22863714 ]
- Yu YM, Yang JS, Peng CZ, Caer V, Cong PZ, Zou ZM, Lu Y, Yang SY, Gu YC: Lactones from Angiopteris caudatiformis. J Nat Prod. 2009 May 22;72(5):921-4. doi: 10.1021/np900027m. [PubMed:19371069 ]
- LOTUS database [Link]
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