Record Information |
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Version | 2.0 |
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Created at | 2020-12-09 00:32:17 UTC |
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Updated at | 2021-07-15 16:45:53 UTC |
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NP-MRD ID | NP0003244 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Oxosorbicillinol |
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Provided By | NPAtlas |
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Description | Oxosorbicillinol is found in Penicillium and Penicillium chrysogenum. Oxosorbicillinol was first documented in 2000 (PMID: 10803967). Based on a literature review very few articles have been published on (2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione (PMID: 15974609) (PMID: 32789380) (PMID: 31943627) (PMID: 29790637) (PMID: 29104566) (PMID: 28618182). |
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Structure | [H]O\C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])[H])=C1/C(O[H])=C(C(=O)[C@@](O[H])(C1=O)C([H])([H])[H])C([H])([H])[H] InChI=1S/C14H16O5/c1-4-5-6-7-9(15)10-11(16)8(2)12(17)14(3,19)13(10)18/h4-7,15-16,19H,1-3H3/b5-4+,7-6+,10-9+/t14-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C14H16O5 |
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Average Mass | 264.2770 Da |
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Monoisotopic Mass | 264.09977 Da |
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IUPAC Name | (2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione |
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Traditional Name | (2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione |
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CAS Registry Number | Not Available |
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SMILES | C\C=C\C=C\C(\O)=C1\C(O)=C(C)C(=O)[C@@](C)(O)C1=O |
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InChI Identifier | InChI=1S/C14H16O5/c1-4-5-6-7-9(15)10-11(16)8(2)12(17)14(3,19)13(10)18/h4-7,15-16,19H,1-3H3/b5-4+,7-6+,10-9+/t14-/m1/s1 |
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InChI Key | JSSFRHLBNRCOAQ-KGAWMYLDSA-N |
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Experimental Spectra |
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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 |
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Chemical Shift Submissions |
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| Not Available |
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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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External Links |
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NPAtlas ID | NPA001693 |
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HMDB ID | Not Available |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8191223 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 10015650 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Good Scents ID | Not Available |
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References |
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General References | - Abe N, Yamamoto K, Hirota A: Novel fungal metabolites, demethylsorbicillin and oxosorbicillinol, isolated from Trichoderma sp. USF-2690. Biosci Biotechnol Biochem. 2000 Mar;64(3):620-2. doi: 10.1271/bbb.64.620. [PubMed:10803967 ]
- Maskey RP, Grun-Wollny I, Laatsch H: Sorbicillin analogues and related dimeric compounds from Penicillium notatum. J Nat Prod. 2005 Jun;68(6):865-70. doi: 10.1021/np040137t. [PubMed:15974609 ]
- Kahlert L, Cox RJ, Skellam E: The same but different: multiple functions of the fungal flavin dependent monooxygenase SorD from Penicillium chrysogenum. Chem Commun (Camb). 2020 Sep 21;56(74):10934-10937. doi: 10.1039/d0cc03203d. Epub 2020 Aug 13. [PubMed:32789380 ]
- Kahlert L, Bassiony EF, Cox RJ, Skellam EJ: Diels-Alder Reactions During the Biosynthesis of Sorbicillinoids. Angew Chem Int Ed Engl. 2020 Mar 27;59(14):5816-5822. doi: 10.1002/anie.201915486. Epub 2020 Feb 4. [PubMed:31943627 ]
- Sib A, Gulder TAM: Chemo-enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)-Epoxysorbicillinol. Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14650-14653. doi: 10.1002/anie.201802176. Epub 2018 Jun 25. [PubMed:29790637 ]
- Derntl C, Guzman-Chavez F, Mello-de-Sousa TM, Busse HJ, Driessen AJM, Mach RL, Mach-Aigner AR: In Vivo Study of the Sorbicillinoid Gene Cluster in Trichoderma reesei. Front Microbiol. 2017 Oct 20;8:2037. doi: 10.3389/fmicb.2017.02037. eCollection 2017. [PubMed:29104566 ]
- Guzman-Chavez F, Salo O, Nygard Y, Lankhorst PP, Bovenberg RAL, Driessen AJM: Mechanism and regulation of sorbicillin biosynthesis by Penicillium chrysogenum. Microb Biotechnol. 2017 Jul;10(4):958-968. doi: 10.1111/1751-7915.12736. Epub 2017 Jun 15. [PubMed:28618182 ]
- Komoda T, Nishikawa M: 6'-Hydroxyoxosorbicillinol, a new lipoxygenase inhibitor and PGD2/LTB4 release suppressor from Penicillium sp. Biosci Biotechnol Biochem. 2012;76(7):1404-6. doi: 10.1271/bbb.120115. Epub 2012 Jul 7. [PubMed:22785490 ]
- Abe N, Arakawa T, Hirota A: The biosynthesis of bisvertinolone: evidence for oxosorbicillinol as a direct precursor. Chem Commun (Camb). 2002 Feb 7;(3):204-5. doi: 10.1039/b109505f. [PubMed:12120368 ]
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