Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 05:05:35 UTC |
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Updated at | 2022-09-07 05:05:35 UTC |
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NP-MRD ID | NP0244322 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (3as,5ar,10ar)-8-formyl-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,7h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid |
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Description | Scabronine G belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (3as,5ar,10ar)-8-formyl-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,7h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid is found in Sarcodon scabrosus. It was first documented in 2005 (PMID: 16190712). Based on a literature review a small amount of articles have been published on Scabronine G (PMID: 18826220) (PMID: 33281604) (PMID: 23765646) (PMID: 21548644). |
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Structure | CC(C)C1=C2[C@H]3CC=C(CC(=O)[C@]3(C)CC[C@]2(CC1)C(O)=O)C=O InChI=1S/C20H26O4/c1-12(2)14-6-7-20(18(23)24)9-8-19(3)15(17(14)20)5-4-13(11-21)10-16(19)22/h4,11-12,15H,5-10H2,1-3H3,(H,23,24)/t15-,19-,20+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C20H26O4 |
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Average Mass | 330.4240 Da |
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Monoisotopic Mass | 330.18311 Da |
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IUPAC Name | (3aS,5aR,10aR)-8-formyl-5a-methyl-6-oxo-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,10H,10aH-cyclohepta[e]indene-3a-carboxylic acid |
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Traditional Name | (3aS,5aR,10aR)-8-formyl-1-isopropyl-5a-methyl-6-oxo-2H,3H,4H,5H,7H,10H,10aH-cyclohepta[e]indene-3a-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C1=C2[C@H]3CC=C(CC(=O)[C@]3(C)CC[C@]2(CC1)C(O)=O)C=O |
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InChI Identifier | InChI=1S/C20H26O4/c1-12(2)14-6-7-20(18(23)24)9-8-19(3)15(17(14)20)5-4-13(11-21)10-16(19)22/h4,11-12,15H,5-10H2,1-3H3,(H,23,24)/t15-,19-,20+/m1/s1 |
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InChI Key | PDFVQJPCHCWDIY-YSGRDPCXSA-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 diterpenoids. These are terpene compounds formed by four 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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic 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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General References | - Halim M, Yee DJ, Sames D: Imaging induction of cytoprotective enzymes in intact human cells: coumberone, a metabolic reporter for human AKR1C enzymes reveals activation by panaxytriol, an active component of red ginseng. J Am Chem Soc. 2008 Oct 29;130(43):14123-8. doi: 10.1021/ja801245y. Epub 2008 Oct 1. [PubMed:18826220 ]
- Nakagawasai O, Lin JR, Odaira T, Takahashi K, Nemoto W, Moriguchi S, Yabuki Y, Kobayakawa Y, Fukunaga K, Nakada M, Tan-No K: Scabronine G Methyl Ester Improves Memory-Related Behavior and Enhances Hippocampal Cell Proliferation and Long-Term Potentiation via the BDNF-CREB Pathway in Olfactory Bulbectomized Mice. Front Pharmacol. 2020 Nov 12;11:583291. doi: 10.3389/fphar.2020.583291. eCollection 2020. [PubMed:33281604 ]
- Kobayakawa Y, Nakada M: Total syntheses of (-)-scabronines G and A, and (-)-episcabronine A. Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7569-73. doi: 10.1002/anie.201303224. Epub 2013 Jun 13. [PubMed:23765646 ]
- Kanoh N, Sakanishi K, Iimori E, Nishimura K, Iwabuchi Y: Asymmetric total synthesis of (-)-scabronine G via intramolecular double Michael reaction and Prins cyclization. Org Lett. 2011 Jun 3;13(11):2864-7. doi: 10.1021/ol200873y. Epub 2011 May 6. [PubMed:21548644 ]
- Waters SP, Tian Y, Li YM, Danishefsky SJ: Total synthesis of (-)-scabronine G, an inducer of neurotrophic factor production. J Am Chem Soc. 2005 Oct 5;127(39):13514-5. doi: 10.1021/ja055220x. [PubMed:16190712 ]
- LOTUS database [Link]
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