| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-27 22:15:25 UTC |
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| Updated at | 2022-04-27 22:15:25 UTC |
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| NP-MRD ID | NP0050847 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Canthin-6-one |
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| Description | Canthin-6-one belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. Canthin-6-one is a strong basic compound (based on its pKa). Canthin-6-one is found in Ailanthus altissima, Ailanthus altissima , Ailanthus malabarica , Ailanthus triphysa, Allium neapolitanum , Brucea antidysenterica, Brucea javanica, Brucea mollis, Eurycoma longifolia , Eurycoma longifolida, Fagaropsis angolensis, Hannoa chlorantha, Hibiscus syriacus, Pentaceras australis, Phellodendron amurense , Phellodendron chinense , Picrasma crenata, Picrasma excelsa, Picrasma quassioides , Pierreodendron africanum, Pulveroboletus curtisii, Quassia africana, Simaba orinocensis, Simaba polyphylla, Simarouba glauca, Zanthoxylum belizense, Zanthoxylum chiloperone var. angustifolium, Zanthoxylum dipetalum, Zanthoxylum ekmanii, Zanthoxylum elephantiasis, Zanthoxylum integrifoliolum, Zanthoxylum mayu, Zanthoxylum ovalifolium, Zanthoxylum piasezkii, Zanthoxylum suberosum, Zanthoxylum viride and Zanthoxylum zanthoxyloides. Canthin-6-one was first documented in 2009 (PMID: 19325221). An indole alkaloid that is 6H-indolonaphthyridine substituted by an oxo group at position 6 (PMID: 21134431) (PMID: 21236329). |
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| Structure | O=C1C=CC2=NC=CC3=C2N1C1=C3C=CC=C1 InChI=1S/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H |
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| Synonyms | | Value | Source |
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| 6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one | ChEBI |
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| Chemical Formula | C14H8N2O |
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| Average Mass | 220.2310 Da |
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| Monoisotopic Mass | 220.06366 Da |
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| IUPAC Name | 1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one |
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| Traditional Name | canthin-6-one |
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| CAS Registry Number | Not Available |
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| SMILES | O=C1C=CC2=NC=CC3=C2N1C1=C3C=CC=C1 |
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| InChI Identifier | InChI=1S/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H |
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| InChI Key | ZERVJPYNQLONEK-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, 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 indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Indolonaphthyridine alkaloids |
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| Sub Class | Not Available |
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| Direct Parent | Indolonaphthyridine alkaloids |
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| Alternative Parents | |
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| Substituents | - Indolo[3,2-1de][1,5]naphthyridine
- Beta-carboline
- Pyridoindole
- Diazanaphthalene
- Naphthyridine
- Indole
- Indole or derivatives
- Indolizine
- Pyrrolopyridine
- Pyridinone
- Pyridine
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Lactam
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | - Tada A, Sugimoto N, Sato K, Akiyama T, Asanoma M, Yun YS, Yamazaki T, Tanamoto K: [Examination of original plant of Jamaica quassia extract, a natural bittering agent, based on composition of the constituents]. Shokuhin Eiseigaku Zasshi. 2009 Feb;50(1):16-21. doi: 10.3358/shokueishi.50.16. [PubMed:19325221 ]
- Ferreira ME, Cebrian-Torrejon G, Corrales AS, Vera de Bilbao N, Rolon M, Gomez CV, Leblanc K, Yaluf G, Schinini A, Torres S, Serna E, Rojas de Arias A, Poupon E, Fournet A: Zanthoxylum chiloperone leaves extract: first sustainable Chagas disease treatment. J Ethnopharmacol. 2011 Feb 16;133(3):986-93. doi: 10.1016/j.jep.2010.11.032. Epub 2010 Dec 4. [PubMed:21134431 ]
- de Souza Almeida ES, Filho VC, Niero R, Clasen BK, Balogun SO, de Oliveira Martins DT: Pharmacological mechanisms underlying the anti-ulcer activity of methanol extract and canthin-6-one of Simaba ferruginea A. St-Hil. in animal models. J Ethnopharmacol. 2011 Apr 12;134(3):630-6. doi: 10.1016/j.jep.2011.01.009. Epub 2011 Jan 12. [PubMed:21236329 ]
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