Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 17:41:50 UTC |
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Updated at | 2021-06-29 23:50:40 UTC |
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NP-MRD ID | NP0025615 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Fumagillin |
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Provided By | JEOL Database |
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Description | Fumagillin is also known as fumidil b. Fumagillin is found in Aspergillus fumigatus and Penicillium janczewskii. It was first documented in 2021 (PMID: 33932203). Based on a literature review a significant number of articles have been published on fumagillin (PMID: 33924845) (PMID: 33903300) (PMID: 33846894) (PMID: 33806001). |
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Structure | [H]OC(=O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(OC2([H])[H])[C@]([H])([C@]1([H])OC([H])([H])[H])[C@]1(O[C@@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20+,23-,24-,25+,26+/m1/s1 |
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Synonyms | |
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Chemical Formula | C26H34O7 |
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Average Mass | 458.5510 Da |
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Monoisotopic Mass | 458.23045 Da |
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IUPAC Name | (2E,4E,6E,8E)-10-{[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid |
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Traditional Name | (2E,4E,6E,8E)-10-{[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(OC2([H])[H])[C@]([H])([C@]1([H])OC([H])([H])[H])[C@]1(O[C@@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20+,23-,24-,25+,26+/m1/s1 |
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InChI Key | NGGMYCMLYOUNGM-AFISTTPQSA-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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1D NMR | 13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Branched fatty acid
- Epoxy fatty acid
- Fatty acid ester
- Heterocyclic fatty acid
- Dicarboxylic acid or derivatives
- Unsaturated fatty acid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Organoheterocyclic compound
- Oxacycle
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- 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 | - Ben Abdelkader F, Cakmak I, Cakmak SS, Nur Z, Incebiyik E, Aktar A, Erdost H: Toxicity assessment of chronic exposure to common insecticides and bee medications on colony development and drones sperm parameters. Ecotoxicology. 2021 Jul;30(5):806-817. doi: 10.1007/s10646-021-02416-3. Epub 2021 May 1. [PubMed:33932203 ]
- Nanetti A, Ugolini L, Cilia G, Pagnotta E, Malaguti L, Cardaio I, Matteo R, Lazzeri L: Seed Meals from Brassica nigra and Eruca sativa Control Artificial Nosema ceranae Infections in Apis mellifera. Microorganisms. 2021 Apr 28;9(5). pii: microorganisms9050949. doi: 10.3390/microorganisms9050949. [PubMed:33924845 ]
- Mohamed Yusoff PS, Osman E, Raja Sabudin RZA: Disseminated microsporidiosis: An underdiagnosed and emerging opportunistic disease. Malays J Pathol. 2021 Apr;43(1):9-18. [PubMed:33903300 ]
- Albayati S, Uba AI, Yelekci K: Potential inhibitors of methionine aminopeptidase type II identified via structure-based pharmacophore modeling. Mol Divers. 2021 Apr 13. pii: 10.1007/s11030-021-10221-7. doi: 10.1007/s11030-021-10221-7. [PubMed:33846894 ]
- Glavinic U, Stevanovic J, Ristanic M, Rajkovic M, Davitkov D, Lakic N, Stanimirovic Z: Potential of Fumagillin and Agaricus blazei Mushroom Extract to Reduce Nosema ceranae in Honey Bees. Insects. 2021 Mar 25;12(4). pii: insects12040282. doi: 10.3390/insects12040282. [PubMed:33806001 ]
- Chu, M., et al. (2001). Chu, M., et al, J. Antibiotics 54, 1096 (2001). J. Antibiotics.
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