Record Information |
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Version | 1.0 |
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Created at | 2022-09-08 08:00:12 UTC |
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Updated at | 2022-09-08 08:00:12 UTC |
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NP-MRD ID | NP0264470 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3ar,4r,6r,6as,7s,9ar,9bs)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-4-hydroxy-2-methylbut-2-enoate |
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Description | (3AR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3ar,4r,6r,6as,7s,9ar,9bs)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3ah,4h,5h,6ah,7h,9ah,9bh-azuleno[4,5-b]furan-4-yl (2z)-4-hydroxy-2-methylbut-2-enoate is found in Eupatorium lindleyanum. It was first documented in 2022 (PMID: 36104165). Based on a literature review a significant number of articles have been published on (3aR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate (PMID: 36104164) (PMID: 36104163) (PMID: 36104162) (PMID: 36104161) (PMID: 36104160) (PMID: 36104159). |
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Structure | C\C(=C\CO)C(=O)O[C@@H]1C[C@](O)(CO)[C@@H]2[C@@H](O)C=C(C)[C@@H]2[C@@H]2OC(=O)C(=C)[C@H]12 InChI=1S/C20H26O8/c1-9(4-5-21)18(24)27-13-7-20(26,8-22)16-12(23)6-10(2)14(16)17-15(13)11(3)19(25)28-17/h4,6,12-17,21-23,26H,3,5,7-8H2,1-2H3/b9-4-/t12-,13+,14-,15+,16+,17-,20-/m0/s1 |
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Synonyms | Value | Source |
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(3AR,4R,6R,6as,7S,9ar,9BS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoic acid | Generator |
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Chemical Formula | C20H26O8 |
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Average Mass | 394.4200 Da |
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Monoisotopic Mass | 394.16277 Da |
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IUPAC Name | (3aR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate |
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Traditional Name | (3aR,4R,6R,6aS,7S,9aR,9bS)-6,7-dihydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl (2Z)-4-hydroxy-2-methylbut-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C\C(=C\CO)C(=O)O[C@@H]1C[C@](O)(CO)[C@@H]2[C@@H](O)C=C(C)[C@@H]2[C@@H]2OC(=O)C(=C)[C@H]12 |
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InChI Identifier | InChI=1S/C20H26O8/c1-9(4-5-21)18(24)27-13-7-20(26,8-22)16-12(23)6-10(2)14(16)17-15(13)11(3)19(25)28-17/h4,6,12-17,21-23,26H,3,5,7-8H2,1-2H3/b9-4-/t12-,13+,14-,15+,16+,17-,20-/m0/s1 |
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InChI Key | BWFIEPPPOFKOKO-PIWZHLCHSA-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 guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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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 | Guaianolides and derivatives |
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Alternative Parents | |
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Substituents | - Guaianolide-skeleton
- Sesquiterpenoid
- Guaiane sesquiterpenoid
- Fatty acid ester
- Fatty acyl
- Gamma butyrolactone
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | - Bamat NA, Orians CM, Abbasi S, Morley CJ, Ross Russell R, Panitch HB, Handley SC, Foglia EE, Posencheg MA, Kirpalani H: Use of ventilation/perfusion mismatch to guide individualised CPAP level selection in preterm infants: a feasibility trial. Arch Dis Child Fetal Neonatal Ed. 2022 Sep 14. pii: archdischild-2022-324474. doi: 10.1136/archdischild-2022-324474. [PubMed:36104165 ]
- Kopel D, Gottschalk CH: The Epidemiology of Primary Headache Disorders. Semin Neurol. 2022 Sep 14. doi: 10.1055/a-1942-6823. [PubMed:36104164 ]
- Cleary NM, O'Gorman A: Hyaluronidase for localised infusion site reaction during continuous subcutaneous infusion. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003909. doi: 10.1136/spcare-2022-003909. [PubMed:36104163 ]
- Hayes J, Waldron D, Levins KJ, Gaffney L, Azhar M, Beatty S, Mannion E: Methadone prescribed as an analgesic by a specialist palliative medicine team in an acute hospital inpatient setting: retrospective study. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003586. doi: 10.1136/spcare-2022-003586. [PubMed:36104162 ]
- Peiro I, Milla J, Arribas L, Hurtos L, Gonzalez-Tampan AR, Bellver M, Fort E, Molina-Mata K, Joudanin JR, Valcarcel J, Gonzalez-Barboteo J: Venting percutaneous radiologic gastrostomy in malignant bowel obstruction: safety and effectiveness in a comprehensive cancer centre. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003895. doi: 10.1136/spcare-2022-003895. [PubMed:36104161 ]
- Cheng J, Yu Q, Tu K, Wang J, Zhang L, Cheng Z: Hierarchical Self-Assembly of Triphilic Main-Chain-Type Semifluorinated Alternating Graft Copolymers in Aqueous Solution. Macromol Rapid Commun. 2022 Sep 14:e2200570. doi: 10.1002/marc.202200570. [PubMed:36104160 ]
- Khasawneh A, Kratzke I, Adapa K, Marks L, Mazur L: Effect of Notes' Access and Complexity on OpenNotes' Utility. Appl Clin Inform. 2022 Oct;13(5):1015-1023. doi: 10.1055/a-1942-6889. Epub 2022 Sep 14. [PubMed:36104159 ]
- Schiel R, Block M, Stein G, Steveling A, Lucking S, Scherberich J: Serum uromodulin in children and adolescents with type 1 diabetes mellitus and controls: Its potential role in kidney health. Exp Clin Endocrinol Diabetes. 2022 Sep 14. doi: 10.1055/a-1944-2686. [PubMed:36104158 ]
- Ury E: Mental health conditions of pandemic healthcare workers: findings from a systematic review and meta-analysis. Evid Based Nurs. 2022 Sep 14. pii: ebnurs-2022-103552. doi: 10.1136/ebnurs-2022-103552. [PubMed:36104157 ]
- Abdollahi S, Ardekanizadeh NH, Poorhosseini SM, Gholamalizadeh M, Roumi Z, Goodarzi MO, Doaei S: Unravelling the Complex Interactions Between the FTO Gene, Lifestyle, and Cancer. Adv Nutr. 2022 Sep 14. pii: 6698714. doi: 10.1093/advances/nmac101. [PubMed:36104156 ]
- Reid BN, Pinsky ML: Simulation-Based Evaluation of Methods, Data Types, and Temporal Sampling Schemes for Detecting Recent Population Declines. Integr Comp Biol. 2022 Dec 30;62(6):1849-1863. doi: 10.1093/icb/icac144. [PubMed:36104155 ]
- Ebbers T, Kool RB, Smeele LE, Takes RP, van den Broek GB, Dirven R: Quantifying the Electronic Health Record Burden in Head and Neck Cancer Care. Appl Clin Inform. 2022 Aug;13(4):857-864. doi: 10.1055/s-0042-1756422. Epub 2022 Sep 14. [PubMed:36104154 ]
- Snead AA, Alda F: Time-Series Sequences for Evolutionary Inferences. Integr Comp Biol. 2022 Dec 30;62(6):1771-1783. doi: 10.1093/icb/icac146. [PubMed:36104153 ]
- Creydt M, Fischer M: Food metabolomics: Latest hardware-developments for nontargeted food authenticity and food safety testing. Electrophoresis. 2022 Dec;43(23-24):2334-2350. doi: 10.1002/elps.202200126. Epub 2022 Oct 6. [PubMed:36104152 ]
- LOTUS database [Link]
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