Record Information |
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Version | 1.0 |
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Created at | 2022-09-11 17:32:25 UTC |
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Updated at | 2022-09-11 17:32:25 UTC |
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NP-MRD ID | NP0317573 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 3-[(13r)-2,13-dihydroxy-13-[(5r,5'r)-5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one |
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Description | Asimicin, also known as bullatacin or rolliniastatin-2, belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 3-[(13r)-2,13-dihydroxy-13-[(5r,5'r)-5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one is found in Annona atemoya, Annona cherimola, Annona glabra, Annona squamosa, Artemisia apiacea, Asimina longifolia, Asimina parviflora, Asimina triloba, Eurytides marcellus, Annona mucosa and Xylopia aromatica. It was first documented in 2018 (PMID: 30353923). Based on a literature review a significant number of articles have been published on Asimicin (PMID: 33586822) (PMID: 33406830) (PMID: 32298749) (PMID: 31250675). |
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Structure | CCCCCCCCCCC(O)[C@H]1CCC(O1)C1CC[C@@H](O1)[C@H](O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28?,30?,31?,32-,33-,34-,35?,36?/m1/s1 |
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Synonyms | Value | Source |
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Bullatacin | MeSH | Rolliniastatin-2 | MeSH | Rolliniastatin-1 | MeSH |
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Chemical Formula | C37H66O7 |
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Average Mass | 622.9280 Da |
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Monoisotopic Mass | 622.48085 Da |
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IUPAC Name | 3-[(13R)-2,13-dihydroxy-13-[(5R,5'R)-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyl-2,5-dihydrofuran-2-one |
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Traditional Name | 3-[(13R)-2,13-dihydroxy-13-[(5R,5'R)-5'-(1-hydroxyundecyl)-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyl-5H-furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCCCCCC(O)[C@H]1CCC(O1)C1CC[C@@H](O1)[C@H](O)CCCCCCCCCCC(O)CC1=CC(C)OC1=O |
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InChI Identifier | InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28?,30?,31?,32-,33-,34-,35?,36?/m1/s1 |
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InChI Key | MBABCNBNDNGODA-XRLPKKPGSA-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 annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. |
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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 alcohols |
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Direct Parent | Annonaceous acetogenins |
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Alternative Parents | |
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Substituents | - Annonaceae acetogenin skeleton
- Long chain fatty alcohol
- 2-furanone
- Dihydrofuran
- Oxolane
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic 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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