| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 04:11:18 UTC |
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| Updated at | 2022-04-28 04:11:18 UTC |
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| NP-MRD ID | NP0058868 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Caleurticolide angelate |
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| Description | (3AR,4S,5R,6R,10S,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-4-[(2-methylprop-2-enoyl)oxy]-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-5-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. Caleurticolide angelate is found in Calea urticifolia. Based on a literature review very few articles have been published on (3aR,4S,5R,6R,10S,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-4-[(2-methylprop-2-enoyl)oxy]-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-5-yl (2Z)-2-methylbut-2-enoate. |
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| Structure | C\C=C(\C)C(=O)O[C@@H]1[C@@H](OC(=O)C(C)=C)[C@H]2[C@@H](C[C@H](C)\C=C/C(=O)[C@]1(C)O)OC(=O)C2=C InChI=1S/C24H30O8/c1-8-14(5)22(27)32-20-19(31-21(26)12(2)3)18-15(6)23(28)30-16(18)11-13(4)9-10-17(25)24(20,7)29/h8-10,13,16,18-20,29H,2,6,11H2,1,3-5,7H3/b10-9-,14-8-/t13-,16-,18-,19+,20-,24+/m1/s1 |
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| Synonyms | | Value | Source |
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| (3AR,4S,5R,6R,10S,11ar)-6-hydroxy-6,10-dimethyl-3-methylidene-4-[(2-methylprop-2-enoyl)oxy]-2,7-dioxo-2H,3H,3ah,4H,5H,6H,7H,10H,11H,11ah-cyclodeca[b]furan-5-yl (2Z)-2-methylbut-2-enoic acid | Generator |
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| Chemical Formula | C24H30O8 |
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| Average Mass | 446.4960 Da |
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| Monoisotopic Mass | 446.19407 Da |
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| IUPAC Name | (3aR,4S,5R,6R,10S,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-4-[(2-methylprop-2-enoyl)oxy]-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,10H,11H,11aH-cyclodeca[b]furan-5-yl (2Z)-2-methylbut-2-enoate |
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| Traditional Name | (3aR,4S,5R,6R,10S,11aR)-6-hydroxy-6,10-dimethyl-3-methylidene-4-[(2-methylprop-2-enoyl)oxy]-2,7-dioxo-3aH,4H,5H,10H,11H,11aH-cyclodeca[b]furan-5-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](OC(=O)C(C)=C)[C@H]2[C@@H](C[C@H](C)\C=C/C(=O)[C@]1(C)O)OC(=O)C2=C |
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| InChI Identifier | InChI=1S/C24H30O8/c1-8-14(5)22(27)32-20-19(31-21(26)12(2)3)18-15(6)23(28)30-16(18)11-13(4)9-10-17(25)24(20,7)29/h8-10,13,16,18-20,29H,2,6,11H2,1,3-5,7H3/b10-9-,14-8-/t13-,16-,18-,19+,20-,24+/m1/s1 |
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| InChI Key | JZPQLIUKOAJRPF-KSJHYCLFSA-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 urticifolia | 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
- Sesquiterpenoid
- Germacrane sesquiterpenoid
- Tricarboxylic acid or derivatives
- Fatty acid ester
- Fatty acyl
- Gamma butyrolactone
- Acyloin
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Tertiary alcohol
- Cyclic ketone
- Lactone
- Ketone
- 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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