| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-05 17:21:09 UTC |
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| Updated at | 2022-09-05 17:21:09 UTC |
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| NP-MRD ID | NP0217118 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 1,7-dihydroxy-3-methyl-5-(λ⁵-diazynylidene)benzo[a]fluorene-6,11-dione |
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| Description | Isoprekinamycin belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. 1,7-dihydroxy-3-methyl-5-(λ⁵-diazynylidene)benzo[a]fluorene-6,11-dione is found in Streptomyces murayamaensis. 1,7-dihydroxy-3-methyl-5-(λ⁵-diazynylidene)benzo[a]fluorene-6,11-dione was first documented in 2007 (PMID: 17585773). Based on a literature review a small amount of articles have been published on Isoprekinamycin (PMID: 30656941) (PMID: 30465587) (PMID: 28044443) (PMID: 21048414). |
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| Structure | CC1=CC(O)=C2C3=C(C4=C(O)C=CC=C4C3=O)C(=O)C(=[N+]=[N-])C2=C1 InChI=1S/C18H10N2O4/c1-7-5-9-13(11(22)6-7)14-15(18(24)16(9)20-19)12-8(17(14)23)3-2-4-10(12)21/h2-6,21-22H,1H3 |
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| Synonyms | Not Available |
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| Chemical Formula | C18H10N2O4 |
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| Average Mass | 318.2880 Da |
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| Monoisotopic Mass | 318.06406 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | Not Available |
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| SMILES | CC1=CC(O)=C2C3=C(C4=C(O)C=CC=C4C3=O)C(=O)C(=[N+]=[N-])C2=C1 |
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| InChI Identifier | InChI=1S/C18H10N2O4/c1-7-5-9-13(11(22)6-7)14-15(18(24)16(9)20-19)12-8(17(14)23)3-2-4-10(12)21/h2-6,21-22H,1H3 |
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| InChI Key | OWPHUUBRUYFHMJ-UHFFFAOYSA-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 fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Fluorenes |
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| Sub Class | Not Available |
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| Direct Parent | Fluorenes |
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| Alternative Parents | |
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| Substituents | - Fluorene
- 1-naphthol
- Naphthalene
- Aryl ketone
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Diazo compound
- Organic diazonium salt
- Ketone
- Organic oxide
- Hydrocarbon derivative
- Organic salt
- Organic zwitterion
- Organooxygen compound
- Organic nitrogen compound
- Organic oxygen compound
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic 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 | - Tang SQ, Bricard J, Schmitt M, Bihel F: Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP. Org Lett. 2019 Feb 1;21(3):844-848. doi: 10.1021/acs.orglett.9b00031. Epub 2019 Jan 18. [PubMed:30656941 ]
- Guo J, Peng X, Wang X, Xie F, Zhang X, Liang G, Sun Z, Liu Y, Cheng M, Liu Y: A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes. Org Biomol Chem. 2018 Dec 5;16(47):9147-9151. doi: 10.1039/c8ob02582g. [PubMed:30465587 ]
- Kawamura M, Kamo S, Azuma S, Kubo K, Sasamori T, Tokitoh N, Kuramochi K, Tsubaki K: Skeletal Rearrangements of Polycyclic alpha-Ketols. Org Lett. 2017 Jan 20;19(2):301-303. doi: 10.1021/acs.orglett.6b03541. Epub 2017 Jan 3. [PubMed:28044443 ]
- Kumamoto T: [Synthetic studies on kinamycin antibiotics]. Yakugaku Zasshi. 2010 Nov;130(11):1535-41. doi: 10.1248/yakushi.130.1535. [PubMed:21048414 ]
- Liu W, Buck M, Chen N, Shang M, Taylor NJ, Asoud J, Wu X, Hasinoff BB, Dmitrienko GI: Total synthesis of isoprekinamycin: structural evidence for enhanced diazonium ion character and growth inhibitory activity toward cancer cells. Org Lett. 2007 Jul 19;9(15):2915-8. doi: 10.1021/ol0712374. Epub 2007 Jun 22. [PubMed:17585773 ]
- LOTUS database [Link]
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