Record Information |
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Version | 1.0 |
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Created at | 2021-01-06 07:11:31 UTC |
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Updated at | 2021-07-15 17:37:44 UTC |
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NP-MRD ID | NP0021950 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Aspulvinone H |
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Provided By | NPAtlas![NPAtlas Logo](/attributions/npatlas_logo_square_small.png) |
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Description | Aspulvinone H is found in Aspergillus flavipes and Aspergillus terreus. It was first documented in 1978 (PMID: 678538). Based on a literature review a small amount of articles have been published on aspulvinone H (PMID: 32565683) (PMID: 33636575) (PMID: 30109333) (PMID: 22380482). |
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Structure | [H]OC1=C(C(=O)O\C1=C(\[H])C1=C([H])C([H])=C(O[H])C(=C1[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C(O[H])C(=C1[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] InChI=1S/C27H28O5/c1-16(2)5-8-19-13-18(7-11-22(19)28)14-24-26(30)25(27(31)32-24)21-10-12-23(29)20(15-21)9-6-17(3)4/h5-7,10-15,28-30H,8-9H2,1-4H3/b24-14- |
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Synonyms | Not Available |
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Chemical Formula | C27H28O5 |
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Average Mass | 432.5160 Da |
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Monoisotopic Mass | 432.19367 Da |
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IUPAC Name | (5Z)-4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methylidene}-2,5-dihydrofuran-2-one |
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Traditional Name | aspulvinone H |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC1=C(O)C=CC(\C=C2/OC(=O)C(=C2O)C2=CC(CC=C(C)C)=C(O)C=C2)=C1 |
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InChI Identifier | InChI=1S/C27H28O5/c1-16(2)5-8-19-13-18(7-11-22(19)28)14-24-26(30)25(27(31)32-24)21-10-12-23(29)20(15-21)9-6-17(3)4/h5-7,10-15,28-30H,8-9H2,1-4H3/b24-14- |
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InChI Key | LFDYHAWYVIBCDT-OYKKKHCWSA-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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Description | This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | 1-hydroxy-2-unsubstituted benzenoids |
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Direct Parent | 1-hydroxy-2-unsubstituted benzenoids |
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Alternative Parents | |
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Substituents | - 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- 2-furanone
- Dihydrofuran
- Enol ester
- Vinylogous acid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Enol
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Organooxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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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 | - Takahashi I, Ojima N, Ogura K, Seto S: Purification and characterization of dimethylallyl pyrophosphate: aspulvinone dimethylallyltransferase from Aspergillus terreus. Biochemistry. 1978 Jun 27;17(13):2696-702. doi: 10.1021/bi00606a037. [PubMed:678538 ]
- Ezekiel CN, Kraak B, Sandoval-Denis M, Sulyok M, Oyedele OA, Ayeni KI, Makinde OM, Akinyemi OM, Krska R, Crous PW, Houbraken J: Diversity and toxigenicity of fungi and description of Fusarium madaense sp. nov. from cereals, legumes and soils in north-central Nigeria. MycoKeys. 2020 Jun 8;67:95-124. doi: 10.3897/mycokeys.67.52716. eCollection 2020. [PubMed:32565683 ]
- Machado FP, Kumla D, Pereira JA, Sousa E, Dethoup T, Freitas-Silva J, Costa PM, Mistry S, Silva AMS, Kijjoa A: Prenylated phenylbutyrolactones from cultures of a marine sponge-associated fungus Aspergillus flavipes KUFA1152. Phytochemistry. 2021 May;185:112709. doi: 10.1016/j.phytochem.2021.112709. Epub 2021 Feb 23. [PubMed:33636575 ]
- Manchoju A, Annadate RA, Desquien L, Pansare SV: Functionalization of diazotetronic acid and application in a stereoselective modular synthesis of pulvinone, aspulvinones A-E, G, Q and their analogues. Org Biomol Chem. 2018 Aug 29;16(34):6224-6238. doi: 10.1039/c8ob01511b. [PubMed:30109333 ]
- Nagia MM, El-Metwally MM, Shaaban M, El-Zalabani SM, Hanna AG: Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Org Med Chem Lett. 2012 Mar 1;2(1):9. doi: 10.1186/2191-2858-2-9. [PubMed:22380482 ]
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