Record Information |
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Version | 2.0 |
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Created at | 2022-04-29 04:46:02 UTC |
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Updated at | 2022-04-29 04:46:02 UTC |
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NP-MRD ID | NP0083853 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Acetosellin |
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Description | Acetosellin belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Acetosellin is found in Cercosporella acetosella Ell. It was first documented in 2017 (PMID: 28081580). Based on a literature review a significant number of articles have been published on Acetosellin (PMID: 35501128) (PMID: 35501127) (PMID: 35501126) (PMID: 35501125). |
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Structure | C\C=C\C=C\C=C\C1=CC(O)=C2C(=O)O[C@@]3(C)C2=C1C1=C(CO[C@H](CO)C1)C3=O InChI=1S/C23H22O6/c1-3-4-5-6-7-8-13-9-17(25)19-20-18(13)15-10-14(11-24)28-12-16(15)21(26)23(20,2)29-22(19)27/h3-9,14,24-25H,10-12H2,1-2H3/b4-3+,6-5+,8-7+/t14-,23-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C23H22O6 |
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Average Mass | 394.4230 Da |
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Monoisotopic Mass | 394.14164 Da |
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IUPAC Name | (4S,9S)-15-[(1E,3E,5E)-hepta-1,3,5-trien-1-yl]-13-hydroxy-4-(hydroxymethyl)-9-methyl-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2(7),12,14-tetraene-8,11-dione |
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Traditional Name | (4S,9S)-15-[(1E,3E,5E)-hepta-1,3,5-trien-1-yl]-13-hydroxy-4-(hydroxymethyl)-9-methyl-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2(7),12,14-tetraene-8,11-dione |
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CAS Registry Number | Not Available |
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SMILES | C\C=C\C=C\C=C\C1=CC(O)=C2C(=O)O[C@@]3(C)C2=C1C1=C(CO[C@H](CO)C1)C3=O |
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InChI Identifier | InChI=1S/C23H22O6/c1-3-4-5-6-7-8-13-9-17(25)19-20-18(13)15-10-14(11-24)28-12-16(15)21(26)23(20,2)29-22(19)27/h3-9,14,24-25H,10-12H2,1-2H3/b4-3+,6-5+,8-7+/t14-,23-/m0/s1 |
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InChI Key | ORBXWZSWCVYENA-FKWVPTGZSA-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 | Species Name | Source | Reference |
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Cercosporella acetosella Ell | - | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthopyrans |
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Sub Class | Not Available |
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Direct Parent | Naphthopyrans |
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Alternative Parents | |
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Substituents | - Naphthopyran
- Benzofuranone
- Naphthalene
- Isobenzofuranone
- Phthalide
- Isocoumaran
- Styrene
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Pyran
- Vinylogous acid
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Primary alcohol
- 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 | - Booke F, Fauser D, Reims N, Bethge M: Unemployment due to the SARS-CoV-2-pandemic among people with and without severe disabilities: a difference-in-differences analysis. Occup Environ Med. 2022 May 2. pii: oemed-2021-108125. doi: 10.1136/oemed-2021-108125. [PubMed:35501128 ]
- Ritonja JA, Aronson KJ, Leung M, Flaten L, Topouza DG, Duan QL, Durocher F, Tranmer JE, Bhatti P: Investigating the relationship between melatonin patterns and methylation in circadian genes among day shift and night shift workers. Occup Environ Med. 2022 May 2. pii: oemed-2021-108111. doi: 10.1136/oemed-2021-108111. [PubMed:35501127 ]
- Kelly-Reif K, Bertke SJ, Samet J, Sood A, Schubauer-Berigan MK: Health burdens of uranium miners will extend beyond the radiation exposure compensation act deadline. Occup Environ Med. 2022 May 2. pii: oemed-2022-108311. doi: 10.1136/oemed-2022-108311. [PubMed:35501126 ]
- Guseva Canu I, Gaillen-Guedy A, Antilla A, Charles S, Fraize-Frontier S, Luce D, McElvenny DM, Merletti F, Michel C, Pukkala E, Schubauer-Berigan MK, Straif K, Wild P, Richardson DB: Lung cancer mortality in the European cohort of titanium dioxide workers: a reanalysis of the exposure-response relationship. Occup Environ Med. 2022 May 2. pii: oemed-2021-108030. doi: 10.1136/oemed-2021-108030. [PubMed:35501125 ]
- Hufendiek P, Stolben SSM, Kehraus S, Merten N, Harms H, Crusemann M, Arslan I, Gutschow M, Schneider T, Konig GM: Biosynthetic Studies on Acetosellin and Structure Elucidation of a New Acetosellin Derivative. Planta Med. 2017 Aug;83(12-13):1044-1052. doi: 10.1055/s-0042-124493. Epub 2017 Jan 12. [PubMed:28081580 ]
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