Record Information |
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Version | 1.0 |
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Created at | 2024-03-29 14:21:35 UTC |
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Updated at | 2024-04-09 04:23:34 UTC |
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NP-MRD ID | NP0332748 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Isoinuviscolide |
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Description | (3AR,4aR,5S,7aR,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-3aH,4H,4aH,6H,7H,7aH,9aH-azuleno[6,5-b]furan-2-one 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. It was first documented in 2024 (PMID: 38551122). Based on a literature review a significant number of articles have been published on (3aR,4aR,5S,7aR,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-3aH,4H,4aH,6H,7H,7aH,9aH-azuleno[6,5-b]furan-2-one (PMID: 38551120) (PMID: 38551119) (PMID: 38551118) (PMID: 38551117). |
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Structure | [H][C@@]12CC[C@@](C)(O)[C@]1([H])C[C@]1([H])C(=C)C(=O)O[C@@]1([H])C=C2C InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h6,10-13,17H,2,4-5,7H2,1,3H3/t10-,11+,12+,13-,15+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C15H20O3 |
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Average Mass | 248.3220 Da |
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Monoisotopic Mass | 248.14124 Da |
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IUPAC Name | (3aR,4aR,5R,7aR,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,7H,7aH,9aH-azuleno[6,5-b]furan-2-one |
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Traditional Name | (3aR,4aR,5R,7aR,9aS)-5-hydroxy-5,8-dimethyl-3-methylidene-3aH,4H,4aH,6H,7H,7aH,9aH-azuleno[6,5-b]furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@]12CC[C@@](C)(O)[C@]1([H])C[C@]1([H])C(=C)C(=O)O[C@@]1([H])C=C2C |
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InChI Identifier | InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h6,10-13,17H,2,4-5,7H2,1,3H3/t10-,11+,12+,13-,15+/m0/s1 |
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InChI Key | APMKESKZWHNIDJ-IHWVXMPCSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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NOESY NMR | [1H, 1H] NMR Spectrum (2D, 601 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 601 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 601 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 601 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | 1D_DEPT NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | kibrom.gebrehiwot@aau.edu.et | Addis Ababa University | Kibrom Bedane | 2024-03-29 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600.2230011 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150.942795469 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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
- Guaiane sesquiterpenoid
- Sesquiterpenoid
- Gamma butyrolactone
- Cyclic alcohol
- Tertiary alcohol
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Lactone
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- 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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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 | - Lima RC, de Lima SR, Rocha MS, Dos Anjos HDB, Dantas YCA, Benites IDN, Queiroz CDCS, Fraga EDC, Batista JDS: Identification of fish specimens of the Tocantins River, Brazil, using DNA barcoding. J Fish Biol. 2024 Mar 29. doi: 10.1111/jfb.15721. [PubMed:38551122 ]
- Authors unspecified: Corrigendum: The empty pelvis syndrome: a core data set from the PelvEx collaborative. Br J Surg. 2024 Mar 2;111(3):znae095. doi: 10.1093/bjs/znae095. [PubMed:38551120 ]
- Cohen RV, Salminen P, Schauer PR, Rubino F: Back to the future: malabsorption is the Achilles' heel of hypoabsorptive metabolic/bariatric procedures. Br J Surg. 2024 Mar 2;111(3):znae073. doi: 10.1093/bjs/znae073. [PubMed:38551119 ]
- Papadia FS, Adami G, Razzetta A, Florenzano A, Longo G, Rubartelli A, Carlini F, De Cian O, Camerini G: Biliopancreatic diversion for severe obesity: long-term weight maintenance and occurrence of nutritional complications are two facets of the same coin. Br J Surg. 2024 Mar 2;111(3):znae058. doi: 10.1093/bjs/znae058. [PubMed:38551118 ]
- Trew S, Russell DH: A Rapid Evidence Assessment on The Effectiveness of Interventions for Autistic Adolescents with Harmful Sexual Behaviors. Trauma Violence Abuse. 2024 Mar 29:15248380241241024. doi: 10.1177/15248380241241024. [PubMed:38551117 ]
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