| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 17:33:28 UTC |
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| Updated at | 2022-09-04 17:33:28 UTC |
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| NP-MRD ID | NP0198998 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (11r)-9-hydroxy-11-(4-hydroxy-3,5-dimethoxyphenyl)-8,16-diazatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(10),2,4,6,8-pentaen-17-one |
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| Description | Isaindigotidione belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. (11r)-9-hydroxy-11-(4-hydroxy-3,5-dimethoxyphenyl)-8,16-diazatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(10),2,4,6,8-pentaen-17-one is found in Isatis tinctoria. (11r)-9-hydroxy-11-(4-hydroxy-3,5-dimethoxyphenyl)-8,16-diazatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1(10),2,4,6,8-pentaen-17-one was first documented in 2010 (PMID: 20845915). Based on a literature review very few articles have been published on Isaindigotidione (PMID: 35754682). |
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| Structure | COC1=CC(=CC(OC)=C1O)[C@H]1C2CCCN2C(=O)C2=C3C=CC=CC3=NC(O)=C12 InChI=1S/C23H22N2O5/c1-29-16-10-12(11-17(30-2)21(16)26)18-15-8-5-9-25(15)23(28)19-13-6-3-4-7-14(13)24-22(27)20(18)19/h3-4,6-7,10-11,15,18,26H,5,8-9H2,1-2H3,(H,24,27)/t15?,18-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C23H22N2O5 |
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| Average Mass | 406.4380 Da |
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| Monoisotopic Mass | 406.15287 Da |
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| IUPAC Name | (11R)-9-hydroxy-11-(4-hydroxy-3,5-dimethoxyphenyl)-8,16-diazatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1,3,5,7,9-pentaen-17-one |
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| Traditional Name | (11R)-9-hydroxy-11-(4-hydroxy-3,5-dimethoxyphenyl)-8,16-diazatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1,3,5,7,9-pentaen-17-one |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC(=CC(OC)=C1O)[C@H]1C2CCCN2C(=O)C2=C3C=CC=CC3=NC(O)=C12 |
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| InChI Identifier | InChI=1S/C23H22N2O5/c1-29-16-10-12(11-17(30-2)21(16)26)18-15-8-5-9-25(15)23(28)19-13-6-3-4-7-14(13)24-22(27)20(18)19/h3-4,6-7,10-11,15,18,26H,5,8-9H2,1-2H3,(H,24,27)/t15?,18-/m0/s1 |
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| InChI Key | IWGANRXBUPWVLV-PKHIMPSTSA-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 hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Quinolines and derivatives |
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| Sub Class | Quinolones and derivatives |
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| Direct Parent | Hydroquinolones |
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| Alternative Parents | |
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| Substituents | - Dihydroquinolone
- Dihydroquinoline
- Methoxyphenol
- Naphthyridine
- Dimethoxybenzene
- M-dimethoxybenzene
- Pyridine carboxylic acid or derivatives
- Methoxybenzene
- Anisole
- Phenol ether
- Phenoxy compound
- Pyridinone
- Alkyl aryl ether
- Phenol
- Benzenoid
- Pyridine
- Monocyclic benzene moiety
- Heteroaromatic compound
- Tertiary carboxylic acid amide
- Pyrrolidine
- Carboxamide group
- Lactam
- Azacycle
- Carboxylic acid derivative
- Ether
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic nitrogen compound
- Organic oxide
- Organic oxygen compound
- 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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