| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-09 15:06:05 UTC |
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| Updated at | 2025-02-11 15:48:43 UTC |
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| NP-MRD ID | NP0286499 |
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| Natural Product DOI | https://doi.org/10.57994/2863 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (-)-methyl jasmonate |
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| Description | Methyl jasmonate, also known as fema 3410, belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. A jasmonate ester that is the methyl ester of jasmonic acid. Methyl jasmonate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methyl jasmonate is a floral, fresh, and jasmine tasting compound. Outside of the human body, Methyl jasmonate is found, on average, in the highest concentration within peppermints. Methyl jasmonate has also been detected, but not quantified in, several different foods, such as onion-family vegetables, lima beans, sweet rowanberries, alaska wild rhubarbs, and brassicas. (-)-methyl jasmonate is found in Arabidopsis thaliana, Artemisia absinthium and Citrus limon. (-)-methyl jasmonate was first documented in 2006 (PMID: 17043086). This could make methyl jasmonate a potential biomarker for the consumption of these foods (PMID: 24497113) (PMID: 18038760) (PMID: 21387099) (PMID: 18847436). |
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| Structure | CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1 |
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| Synonyms | | Value | Source |
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| 3-oxo-2-(2-Pentenyl)cyclopentaneacetic acid methyl ester | ChEBI | | Methyl (-)-jasmonate | ChEBI | | (-)-Methyl jasmonate | Kegg | | 3-oxo-2-(2-Pentenyl)cyclopentaneacetate methyl ester | Generator | | Methyl (-)-jasmonic acid | Generator | | (-)-Methyl jasmonic acid | Generator | | Methyl jasmonic acid | Generator | | (-)-Jasmonic acid methyl ester | HMDB | | (3R,7R)-Methyl jasmonate | HMDB | | FEMA 3410 | HMDB | | Jasmonic acid methyl ester | HMDB | | Methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetate | HMDB | | Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate | HMDB | | Methyl cis-jasmonate | HMDB | | Z-Methyl jasmonoate | HMDB | | Methyl epijasmonate | HMDB |
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| Chemical Formula | C13H20O3 |
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| Average Mass | 224.2961 Da |
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| Monoisotopic Mass | 224.14124 Da |
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| IUPAC Name | methyl 2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetate |
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| Traditional Name | (-)-methyl jasmonate |
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| CAS Registry Number | Not Available |
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| SMILES | CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O |
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| InChI Identifier | InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1 |
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| InChI Key | GEWDNTWNSAZUDX-WQMVXFAESA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum |
| | 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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600, CDCl3, simulated) | bgnzk@missouri.edu | Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2024-06-18 | View Spectrum |
| | 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 jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Lineolic acids and derivatives |
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| Direct Parent | Jasmonic acids |
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| Alternative Parents | |
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| Substituents | - Jasmonic acid
- Methyl ester
- Cyclic ketone
- Ketone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic 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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