| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-10 23:48:32 UTC |
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| Updated at | 2022-09-10 23:48:32 UTC |
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| NP-MRD ID | NP0306987 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 7-epi-zingiberene |
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| Description | 7-Epi-zingiberene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 7-epi-zingiberene is found in Pimpinella anisum, Pimpinella isaurica, Senecio squalidus, Solanum habrochaites and Zingiber officinale. 7-epi-zingiberene was first documented in 2011 (PMID: 21074818). Based on a literature review a small amount of articles have been published on 7-epi-zingiberene (PMID: 33617106) (PMID: 32153603) (PMID: 22563774) (PMID: 23169639). |
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| Structure | C[C@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1 InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15-/m1/s1 |
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| Synonyms | | Value | Source |
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| (-)-(4S,7R)-7-Epi-zingiberene | ChEBI | | (-)-(4S,7R)-7-Epizingiberene | ChEBI | | 7-Epizingiberene | ChEBI | | (5R)-2-Methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene | Kegg |
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| Chemical Formula | C15H24 |
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| Average Mass | 204.3570 Da |
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| Monoisotopic Mass | 204.18780 Da |
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| IUPAC Name | (5R)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene |
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| Traditional Name | (5R)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H](CCC=C(C)C)[C@H]1CC=C(C)C=C1 |
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| InChI Identifier | InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-10,14-15H,5,7,11H2,1-4H3/t14-,15-/m1/s1 |
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| InChI Key | KKOXKGNSUHTUBV-HUUCEWRRSA-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, 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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| 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 sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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| Direct Parent | Sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Bisabolane sesquiterpenoid
- Sesquiterpenoid
- Branched unsaturated hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- 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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| General References | - Bleeker PM, Diergaarde PJ, Ament K, Schutz S, Johne B, Dijkink J, Hiemstra H, de Gelder R, de Both MT, Sabelis MW, Haring MA, Schuurink RC: Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies. Phytochemistry. 2011 Jan;72(1):68-73. doi: 10.1016/j.phytochem.2010.10.014. Epub 2010 Nov 11. [PubMed:21074818 ]
- Zabel S, Brandt W, Porzel A, Athmer B, Bennewitz S, Schafer P, Kortbeek R, Bleeker P, Tissier A: A single cytochrome P450 oxidase from Solanum habrochaites sequentially oxidizes 7-epi-zingiberene to derivatives toxic to whiteflies and various microorganisms. Plant J. 2021 Mar;105(5):1309-1325. doi: 10.1111/tpj.15113. Epub 2021 Jan 4. [PubMed:33617106 ]
- Dawood MH, Snyder JC: The Alcohol and Epoxy Alcohol of Zingiberene, Produced in Trichomes of Wild Tomato, Are More Repellent to Spider Mites Than Zingiberene. Front Plant Sci. 2020 Feb 21;11:35. doi: 10.3389/fpls.2020.00035. eCollection 2020. [PubMed:32153603 ]
- Gonzales-Vigil E, Hufnagel DE, Kim J, Last RL, Barry CS: Evolution of TPS20-related terpene synthases influences chemical diversity in the glandular trichomes of the wild tomato relative Solanum habrochaites. Plant J. 2012 Sep;71(6):921-35. doi: 10.1111/j.1365-313X.2012.05040.x. Epub 2012 Jun 22. [PubMed:22563774 ]
- Bleeker PM, Mirabella R, Diergaarde PJ, VanDoorn A, Tissier A, Kant MR, Prins M, de Vos M, Haring MA, Schuurink RC: Improved herbivore resistance in cultivated tomato with the sesquiterpene biosynthetic pathway from a wild relative. Proc Natl Acad Sci U S A. 2012 Dec 4;109(49):20124-9. doi: 10.1073/pnas.1208756109. Epub 2012 Nov 19. [PubMed:23169639 ]
- LOTUS database [Link]
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