Record Information |
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Version | 2.0 |
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Created at | 2020-12-09 03:29:31 UTC |
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Updated at | 2021-07-15 16:54:56 UTC |
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NP-MRD ID | NP0006487 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Cyrneine A |
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Provided By | NPAtlas |
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Description | Cyrneine A is found in Sarcodon cyrneus. Cyrneine A was first documented in 2006 (PMID: 16881016). Based on a literature review a significant number of articles have been published on Cyrneine a (PMID: 17320402) (PMID: 30793912) (PMID: 29858575) (PMID: 22431475) (PMID: 17337280). |
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Structure | [H]O[C@]1([H])C([H])([H])C(=C2C3=C([H])C([H])=C(C([H])=O)C([H])([H])[C@]([H])(O[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H] InChI=1S/C20H28O3/c1-12(2)14-10-17(23)20(4)8-7-19(3)15(18(14)20)6-5-13(11-21)9-16(19)22/h5-6,11-12,16-17,22-23H,7-10H2,1-4H3/t16-,17+,19+,20-/m0/s1 |
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Synonyms | Value | Source |
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1,14-Dihydroxycyantha-3,5(10),11-triene-12-carbaldehyde | MeSH |
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Chemical Formula | C20H28O3 |
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Average Mass | 316.4410 Da |
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Monoisotopic Mass | 316.20384 Da |
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IUPAC Name | (3R,3aR,5aR,6S)-3,6-dihydroxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde |
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Traditional Name | cyrneine A |
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CAS Registry Number | Not Available |
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SMILES | CC(C)C1=C2C3=CC=C(C[C@H](O)[C@]3(C)CC[C@@]2(C)[C@H](O)C1)C=O |
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InChI Identifier | InChI=1S/C20H28O3/c1-12(2)14-10-17(23)20(4)8-7-19(3)15(18(14)20)6-5-13(11-21)9-16(19)22/h5-6,11-12,16-17,22-23H,7-10H2,1-4H3/t16-,17+,19+,20-/m0/s1 |
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InChI Key | IXBCZHOTZLYJDA-CUDHKJQZSA-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 | |
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Chemical Taxonomy |
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Classification | Not classified |
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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 | - Marcotullio MC, Pagiott R, Maltese F, Obara Y, Hoshino T, Nakahata N, Curini M: Neurite outgrowth activity of cyathane diterpenes from Sarcodon cyrneus, cyrneines A and B. Planta Med. 2006 Jul;72(9):819-23. doi: 10.1055/s-2006-946681. [PubMed:16881016 ]
- Marcotullio MC, Pagiotti R, Maltese F, Oball-Mond Mwankie GN, Hoshino T, Obara Y, Nakahata N: Cyathane diterpenes from Sarcodon cyrneus and evaluation of their activities of neuritegenesis and nerve growth factor production. Bioorg Med Chem. 2007 Apr 15;15(8):2878-82. doi: 10.1016/j.bmc.2007.02.019. Epub 2007 Feb 13. [PubMed:17320402 ]
- Wu GJ, Zhang YH, Tan DX, He L, Cao BC, He YP, Han FS: Synthetic Studies on Enantioselective Total Synthesis of Cyathane Diterpenoids: Cyrneines A and B, Glaucopine C, and (+)-Allocyathin B2. J Org Chem. 2019 Mar 15;84(6):3223-3238. doi: 10.1021/acs.joc.8b03138. Epub 2019 Mar 4. [PubMed:30793912 ]
- Wu GJ, Zhang YH, Tan DX, Han FS: Total synthesis of cyrneines A-B and glaucopine C. Nat Commun. 2018 Jun 1;9(1):2148. doi: 10.1038/s41467-018-04480-6. [PubMed:29858575 ]
- Elamparuthi E, Fellay C, Neuburger M, Gademann K: Total synthesis of cyrneine A. Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4071-3. doi: 10.1002/anie.201200515. Epub 2012 Mar 16. [PubMed:22431475 ]
- Obara Y, Hoshino T, Marcotullio MC, Pagiotti R, Nakahata N: A novel cyathane diterpene, cyrneine A, induces neurite outgrowth in a Rac1-dependent mechanism in PC12 cells. Life Sci. 2007 Apr 10;80(18):1669-77. doi: 10.1016/j.lfs.2007.01.057. Epub 2007 Feb 12. [PubMed:17337280 ]
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