| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 20:19:40 UTC |
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| Updated at | 2022-09-04 20:19:40 UTC |
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| NP-MRD ID | NP0201306 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (3z,9z)-5,11-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione |
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| Description | Clonostachydiol belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (3z,9z)-5,11-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione was first documented in 2006 (PMID: 16643039). Based on a literature review a small amount of articles have been published on Clonostachydiol (PMID: 21226484) (PMID: 29348525) (PMID: 26728016) (PMID: 19382764). |
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| Structure | CC1CCC(O)\C=C/C(=O)OC(C)C(O)\C=C/C(=O)O1 InChI=1S/C14H20O6/c1-9-3-4-11(15)5-7-14(18)20-10(2)12(16)6-8-13(17)19-9/h5-12,15-16H,3-4H2,1-2H3/b7-5-,8-6- |
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| Synonyms | Not Available |
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| Chemical Formula | C14H20O6 |
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| Average Mass | 284.3080 Da |
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| Monoisotopic Mass | 284.12599 Da |
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| IUPAC Name | (3Z,9Z)-5,11-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione |
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| Traditional Name | (3Z,9Z)-5,11-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione |
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| CAS Registry Number | Not Available |
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| SMILES | CC1CCC(O)\C=C/C(=O)OC(C)C(O)\C=C/C(=O)O1 |
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| InChI Identifier | InChI=1S/C14H20O6/c1-9-3-4-11(15)5-7-14(18)20-10(2)12(16)6-8-13(17)19-9/h5-12,15-16H,3-4H2,1-2H3/b7-5-,8-6- |
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| InChI Key | SSVNIYICRYPPEB-SFECMWDFSA-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 | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Macrolides and analogues |
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| Sub Class | Not Available |
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| Direct Parent | Macrolides and analogues |
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| Alternative Parents | |
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| Substituents | - Macrolide
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- 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 | - Lang G, Mitova MI, Ellis G, van der Sar S, Phipps RK, Blunt JW, Cummings NJ, Cole AL, Munro MH: Bioactivity profiling using HPLC/microtiter-plate analysis: application to a New Zealand marine alga-derived fungus, Gliocladium sp. J Nat Prod. 2006 Apr;69(4):621-4. doi: 10.1021/np0504917. [PubMed:16643039 ]
- Isaka M, Yangchum A, Auncharoen P, Srichomthong K, Srikitikulchai P: Ring B aromatic norpimarane glucoside from a Xylaria sp. J Nat Prod. 2011 Feb 25;74(2):300-2. doi: 10.1021/np100873t. Epub 2011 Jan 12. [PubMed:21226484 ]
- Ojima KI, Yangchum A, Laksanacharoen P, Tasanathai K, Thanakitpipattana D, Tokuyama H, Isaka M: Cordybislactone, a stereoisomer of the 14-membered bislactone clonostachydiol, from the hopper pathogenic fungus Cordyceps sp. BCC 49294: revision of the absolute configuration of clonostachydiol. J Antibiot (Tokyo). 2018 Mar;71(3):351-358. doi: 10.1038/s41429-017-0008-9. Epub 2018 Jan 18. [PubMed:29348525 ]
- Degenkolb T, Vilcinskas A: Metabolites from nematophagous fungi and nematicidal natural products from fungi as alternatives for biological control. Part II: metabolites from nematophagous basidiomycetes and non-nematophagous fungi. Appl Microbiol Biotechnol. 2016 May;100(9):3813-24. doi: 10.1007/s00253-015-7234-5. Epub 2016 Jan 4. [PubMed:26728016 ]
- Han J, Su Y, Jiang T, Xu Y, Huo X, She X, Pan X: Asymmetric total synthesis and revision of the absolute configuration of 4-keto-clonostachydiol. J Org Chem. 2009 May 15;74(10):3930-2. doi: 10.1021/jo900370a. [PubMed:19382764 ]
- LOTUS database [Link]
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