| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 10:41:28 UTC |
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| Updated at | 2022-04-28 10:41:29 UTC |
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| NP-MRD ID | NP0066435 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Curvularin |
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| Description | Curvularin 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. Curvularin is found in Alternaria cinerariae, Cercospora spp., Curvularia spp., Drechslera rostrata IMI 356287, Drechslera sp., Neopetrosia chaliniformis, Penicillium citreo-viride B, Penicillium citreonigrum, Penicillium gilmanii, Penicillium sp. and Penicillium sumatrense. Curvularin was first documented in 2019 (PMID: 31406682). Based on a literature review a small amount of articles have been published on Curvularin (PMID: 34458061) (PMID: 32843724) (PMID: 32252191) (PMID: 31109256). |
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| Structure | C[C@H]1CCCCCC(=O)C2=C(CC(=O)O1)C=C(O)C=C2O InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1 |
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| Synonyms | | Value | Source |
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| 10,11-Dehydrocurvularin | MeSH |
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| Chemical Formula | C16H20O5 |
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| Average Mass | 292.3310 Da |
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| Monoisotopic Mass | 292.13107 Da |
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| IUPAC Name | (4S)-11,13-dihydroxy-4-methyl-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecine-2,10-dione |
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| Traditional Name | (4S)-11,13-dihydroxy-4-methyl-4,5,6,7,8,9-hexahydro-1H-3-benzoxacyclododecine-2,10-dione |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1CCCCCC(=O)C2=C(CC(=O)O1)C=C(O)C=C2O |
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| InChI Identifier | InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1 |
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| InChI Key | VDUIGYAPSXCJFC-JTQLQIEISA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 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
- Aryl ketone
- Aryl alkyl ketone
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Vinylogous acid
- Carboxylic acid ester
- Ketone
- Lactone
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic 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 | - Wang C, Zaman KHAU, Sarotti AM, Wu X, Zheng SL, Cao S: NF-kappaB inhibitory, antimicrobial and antiproliferative potentials of compounds from Hawaiian fungus Aspergillus polyporicola FS910. 3 Biotech. 2021 Aug;11(8):391. doi: 10.1007/s13205-021-02877-7. Epub 2021 Jul 30. [PubMed:34458061 ]
- Liu G, Niu S, Liu L: Alterchromanone A, one new chromanone derivative from the mangrove endophytic fungus Alternaria longipes. J Antibiot (Tokyo). 2021 Feb;74(2):152-155. doi: 10.1038/s41429-020-00364-4. Epub 2020 Aug 25. [PubMed:32843724 ]
- Banala RR, Vemuri SK, Ev S, Av GR, Gpv S: The Anti-Inflammatory and Cytoprotective Efficiency of Curvularin, a Fungal Macrolactone against Lipopolysaccharide-Induced Inflammatory Response in Nucleus Pulposus Cells: An In Vitro Study. Asian Spine J. 2021 Apr;15(2):143-154. doi: 10.31616/asj.2019.0285. Epub 2020 Apr 8. [PubMed:32252191 ]
- Meena M, Samal S: Alternaria host-specific (HSTs) toxins: An overview of chemical characterization, target sites, regulation and their toxic effects. Toxicol Rep. 2019 Jul 17;6:745-758. doi: 10.1016/j.toxrep.2019.06.021. eCollection 2019. [PubMed:31406682 ]
- Misihairabgwi JM, Ishola A, Sulyok M, Krska R: Mycotoxin and cyanogenic glycoside assessment of the traditional leafy vegetables mutete and omboga from Namibia. Food Addit Contam Part B Surveill. 2019 Dec;12(4):245-251. doi: 10.1080/19393210.2019.1616829. Epub 2019 May 20. [PubMed:31109256 ]
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