| Record Information |
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| Version | 2.0 |
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| Created at | 2021-01-05 23:32:48 UTC |
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| Updated at | 2024-09-03 04:15:14 UTC |
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| NP-MRD ID | NP0014354 |
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| Natural Product DOI | https://doi.org/10.57994/0191 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Pyridoxatin |
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| Provided By | NPAtlas |
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| Description | Pyridoxatin is found in Acremonium sp. BX86 and Tolypocladium sp. CMB-MF028. Pyridoxatin was first documented in 2015 (PMID: 26107107). Based on a literature review a small amount of articles have been published on Pyridoxatin (PMID: 28383912) (PMID: 34379730) (PMID: 31152280) (PMID: 28704971). |
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| Structure | [H]ON1C([H])=C([H])C(O[H])=C(C1=O)[C@@]1([H])[C@]([H])(C([H])=C([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@]1([H])C([H])([H])[H] InChI=1S/C15H21NO3/c1-4-11-8-9(2)7-10(3)13(11)14-12(17)5-6-16(19)15(14)18/h4-6,9-11,13,17,19H,1,7-8H2,2-3H3/t9-,10+,11-,13-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C15H21NO3 |
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| Average Mass | 263.3370 Da |
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| Monoisotopic Mass | 263.15214 Da |
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| IUPAC Name | 3-[(1R,2S,4R,6S)-2-ethenyl-4,6-dimethylcyclohexyl]-1,4-dihydroxy-1,2-dihydropyridin-2-one |
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| Traditional Name | 3-[(1R,2S,4R,6S)-2-ethenyl-4,6-dimethylcyclohexyl]-1,4-dihydroxypyridin-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@@H]1C[C@H](C)[C@H]([C@@H](C1)C=C)C1=C(O)C=CN(O)C1=O |
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| InChI Identifier | InChI=1S/C15H21NO3/c1-4-11-8-9(2)7-10(3)13(11)14-12(17)5-6-16(19)15(14)18/h4-6,9-11,13,17,19H,1,7-8H2,2-3H3/t9-,10+,11-,13-/m1/s1 |
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| InChI Key | OQJADHLOEAOIGC-LSCVPOLPSA-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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| ROESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | r.capon@imb.uq.edu.au | Not Available | Not Available | 2022-12-22 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | r.capon@imb.uq.edu.au | Not Available | Not Available | 2022-12-22 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | r.capon@imb.uq.edu.au | Not Available | Not Available | 2022-12-22 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental) | r.capon@imb.uq.edu.au | Not Available | Not Available | 2022-12-22 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental) | r.capon@imb.uq.edu.au | Not Available | Not Available | 2022-12-22 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental) | r.capon@imb.uq.edu.au | Not Available | Not Available | 2022-12-22 | 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, 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 | - Shang Z, Li L, Esposito BP, Salim AA, Khalil ZG, Quezada M, Bernhardt PV, Capon RJ: New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp. Org Biomol Chem. 2015 Jul 28;13(28):7795-802. doi: 10.1039/c5ob01058f. [PubMed:26107107 ]
- Shang Z, Salim AA, Capon RJ: Chaunopyran A: Co-Cultivation of Marine Mollusk-Derived Fungi Activates a Rare Class of 2-Alkenyl-Tetrahydropyran. J Nat Prod. 2017 Apr 28;80(4):1167-1172. doi: 10.1021/acs.jnatprod.7b00144. Epub 2017 Apr 6. [PubMed:28383912 ]
- Motoyama T, Ishii T, Kamakura T, Osada H: Screening of tenuazonic acid production-inducing compounds and identification of NPD938 as a regulator of fungal secondary metabolism. Biosci Biotechnol Biochem. 2021 Sep 22;85(10):2200-2208. doi: 10.1093/bbb/zbab143. [PubMed:34379730 ]
- da Silva GS, Shang Z, Kalansuriya P, Capon RJ, Esposito BP: Antioxidant activity and cellular uptake of the hydroxamate-based fungal iron chelators pyridoxatin, desferriastechrome and desferricoprogen. Biometals. 2019 Aug;32(4):707-715. doi: 10.1007/s10534-019-00202-7. Epub 2019 Jun 1. [PubMed:31152280 ]
- Lin J, Niu S, Ding Z, Wang R, Dai Q, Wei W, Luo R, Liu L: Isolation and Characterization of Aphidicolin Derivatives from Tolypocladium inflatum. Molecules. 2017 Jul 12;22(7). pii: molecules22071168. doi: 10.3390/molecules22071168. [PubMed:28704971 ]
- DOI: 10.1039/c5ob01058f
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