| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-08 23:10:03 UTC |
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| Updated at | 2022-09-08 23:10:03 UTC |
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| NP-MRD ID | NP0275427 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1s,2r,5s,6r)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol |
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| Description | Asperpentyn belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). (1s,2r,5s,6r)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol is found in Aspergillus duricaulis and Rhizophora apiculata. (1s,2r,5s,6r)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol was first documented in 2009 (PMID: 19115846). Based on a literature review a small amount of articles have been published on Asperpentyn (PMID: 35628710) (PMID: 32343875) (PMID: 32174195) (PMID: 26270650). |
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| Structure | CC(=C)C#CC1=C[C@H](O)[C@H]2O[C@H]2[C@@H]1O InChI=1S/C11H12O3/c1-6(2)3-4-7-5-8(12)10-11(14-10)9(7)13/h5,8-13H,1H2,2H3/t8-,9+,10+,11-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C11H12O3 |
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| Average Mass | 192.2140 Da |
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| Monoisotopic Mass | 192.07864 Da |
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| IUPAC Name | (1S,2R,5S,6R)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol |
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| Traditional Name | (1S,2R,5S,6R)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol |
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| CAS Registry Number | Not Available |
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| SMILES | CC(=C)C#CC1=C[C@H](O)[C@H]2O[C@H]2[C@@H]1O |
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| InChI Identifier | InChI=1S/C11H12O3/c1-6(2)3-4-7-5-8(12)10-11(14-10)9(7)13/h5,8-13H,1H2,2H3/t8-,9+,10+,11-/m0/s1 |
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| InChI Key | KPEYCTJGQFOOBS-ZDCRXTMVSA-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 secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Alcohols and polyols |
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| Direct Parent | Secondary alcohols |
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| Alternative Parents | |
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| Substituents | - Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic 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 | - Li J, Park S, Miller RL, Lee D: Tandem enyne metathesis-metallotropic [1,3]-shift for a concise total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A. Org Lett. 2009 Feb 5;11(3):571-4. doi: 10.1021/ol802675j. [PubMed:19115846 ]
- Zhuravleva OI, Oleinikova GK, Antonov AS, Kirichuk NN, Pelageev DN, Rasin AB, Menshov AS, Popov RS, Kim NY, Chingizova EA, Chingizov AR, Volchkova OO, von Amsberg G, Dyshlovoy SA, Yurchenko EA, Guzhova IV, Yurchenko AN: New Antibacterial Chloro-Containing Polyketides from the Alga-Derived Fungus Asteromyces cruciatus KMM 4696. J Fungi (Basel). 2022 Apr 27;8(5):454. doi: 10.3390/jof8050454. [PubMed:35628710 ]
- Chen YR, Naresh A, Liang SY, Lin CH, Chein RJ, Lin HC: Discovery of a Dual Function Cytochrome P450 that Catalyzes Enyne Formation in Cyclohexanoid Terpenoid Biosynthesis. Angew Chem Int Ed Engl. 2020 Aug 3;59(32):13537-13541. doi: 10.1002/anie.202004435. Epub 2020 Jun 2. [PubMed:32343875 ]
- Polli AD, Ribeiro MADS, Garcia A, Polonio JC, Santos CM, Silva AA, Orlandelli RC, Castro JC, Abreu-Filho BA, Cabral MRP, Sarragiotto MH, Pamphile JA, Azevedo JL: Secondary metabolites of Curvularia sp. G6-32, an endophyte of Sapindus saponaria, with antioxidant and anticholinesterasic properties. Nat Prod Res. 2021 Nov;35(21):4148-4153. doi: 10.1080/14786419.2020.1739681. Epub 2020 Mar 16. [PubMed:32174195 ]
- Lan P, White LE, Taher ES, Guest PE, Banwell MG, Willis AC: Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A. J Nat Prod. 2015 Aug 28;78(8):1963-8. doi: 10.1021/acs.jnatprod.5b00304. Epub 2015 Aug 13. [PubMed:26270650 ]
- LOTUS database [Link]
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