| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 04:11:01 UTC |
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| Updated at | 2022-04-28 04:11:01 UTC |
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| NP-MRD ID | NP0058861 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Calein A |
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| Description | (3AR,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Calein A is found in Calea ternifolia, Calea zacatechichi and Calea zactechichi. Based on a literature review very few articles have been published on (3aR,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate. |
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| Structure | C\C=C(\C)C(=O)O[C@H]1[C@H]2[C@@H](C[C@@H](C)\C=C/C(=O)[C@](C)(O)[C@@H]1OC(C)=O)OC(=O)C2=C InChI=1S/C22H28O8/c1-7-12(3)20(25)30-18-17-13(4)21(26)29-15(17)10-11(2)8-9-16(24)22(6,27)19(18)28-14(5)23/h7-9,11,15,17-19,27H,4,10H2,1-3,5-6H3/b9-8-,12-7-/t11-,15+,17+,18-,19+,22-/m0/s1 |
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| Synonyms | | Value | Source |
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| (3AR,4S,5R,6R,10R,11ar)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2H,3H,3ah,4H,5H,6H,7H,10H,11H,11ah-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoic acid | Generator |
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| Chemical Formula | C22H28O8 |
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| Average Mass | 420.4580 Da |
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| Monoisotopic Mass | 420.17842 Da |
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| IUPAC Name | (3aR,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate |
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| Traditional Name | (3aR,4S,5R,6R,10R,11aR)-5-(acetyloxy)-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3aH,4H,5H,10H,11H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate |
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| CAS Registry Number | Not Available |
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| SMILES | C\C=C(\C)C(=O)O[C@H]1[C@H]2[C@@H](C[C@@H](C)\C=C/C(=O)[C@](C)(O)[C@@H]1OC(C)=O)OC(=O)C2=C |
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| InChI Identifier | InChI=1S/C22H28O8/c1-7-12(3)20(25)30-18-17-13(4)21(26)29-15(17)10-11(2)8-9-16(24)22(6,27)19(18)28-14(5)23/h7-9,11,15,17-19,27H,4,10H2,1-3,5-6H3/b9-8-,12-7-/t11-,15+,17+,18-,19+,22-/m0/s1 |
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| InChI Key | DXPFQBFCOCKNEU-CWOPDIFVSA-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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| Calea ternifolia | LOTUS Database | | | Calea zacatechichi | Plant | | | Calea zactechichi | Plant | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. |
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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 | Germacranolides and derivatives |
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| Alternative Parents | |
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| Substituents | - Germacranolide
- Germacrane sesquiterpenoid
- Sesquiterpenoid
- Tricarboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- Acyloin
- Gamma butyrolactone
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Cyclic ketone
- Ketone
- Lactone
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- 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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