Record Information |
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Version | 1.0 |
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Created at | 2022-04-28 08:03:54 UTC |
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Updated at | 2022-04-28 08:03:54 UTC |
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NP-MRD ID | NP0063700 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Apressin (sesquiterpene) |
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Description | (1R,2R,3R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]Pentadec-14-en-3-yl acetate belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Apressin (sesquiterpene) is found in Achillea depressa and Achillea pseudopectinata. Based on a literature review very few articles have been published on (1R,2R,3R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]Pentadec-14-en-3-yl acetate. |
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Structure | CC(=O)O[C@@H]1C[C@@H]2[C@H](OC(=O)C2=C)[C@H]2[C@@]3(C)OO[C@@]2(C=C3)[C@]1(C)O InChI=1S/C17H20O7/c1-8-10-7-11(21-9(2)18)16(4,20)17-6-5-15(3,23-24-17)13(17)12(10)22-14(8)19/h5-6,10-13,20H,1,7H2,2-4H3/t10-,11+,12-,13-,15-,16+,17+/m0/s1 |
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Synonyms | Value | Source |
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(1R,2R,3R,5S,9S,10S,11S)-2-Hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0,.0,]pentadec-14-en-3-yl acetic acid | Generator |
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Chemical Formula | C17H20O7 |
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Average Mass | 336.3400 Da |
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Monoisotopic Mass | 336.12090 Da |
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IUPAC Name | (1R,2R,3R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadec-14-en-3-yl acetate |
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Traditional Name | (1R,2R,3R,5S,9S,10S,11S)-2-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8,12,13-trioxatetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadec-14-en-3-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@@H]1C[C@@H]2[C@H](OC(=O)C2=C)[C@H]2[C@@]3(C)OO[C@@]2(C=C3)[C@]1(C)O |
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InChI Identifier | InChI=1S/C17H20O7/c1-8-10-7-11(21-9(2)18)16(4,20)17-6-5-15(3,23-24-17)13(17)12(10)22-14(8)19/h5-6,10-13,20H,1,7H2,2-4H3/t10-,11+,12-,13-,15-,16+,17+/m0/s1 |
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InChI Key | XOZFCTKEUWXPAF-RTXDRFAKSA-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 guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene lactones |
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Direct Parent | Guaianolides and derivatives |
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Alternative Parents | |
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Substituents | - Guaianolide-skeleton
- Sesquiterpenoid
- Gamma butyrolactone
- Dicarboxylic acid or derivatives
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Tertiary alcohol
- Cyclic alcohol
- Ortho-dioxolane
- Dialkyl peroxide
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic 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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