| Record Information |
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| Version | 2.0 |
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| Created at | 2024-07-10 11:13:38 UTC |
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| Updated at | 2026-02-05 21:07:12 UTC |
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| NP-MRD ID | NP0333595 |
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| Natural Product DOI | https://doi.org/10.57994/3070 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Undobolin L |
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| Description | Undobolin L belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. Undobolin L was first documented in 2024 (PMID: 39051441). Based on a literature review very few articles have been published on Undobolin L. |
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| Structure | [H][C@@]1(CC[C@]2(C)C[C@@]3([H])[C@]([H])(CC[C@@]3(C)O)C(=C)[C@@H](O)C[C@@]12[H])[C@@H](C)CC\C=C(/C)CO InChI=1S/C25H42O3/c1-16(15-26)7-6-8-17(2)19-9-11-24(4)14-22-20(10-12-25(22,5)28)18(3)23(27)13-21(19)24/h7,17,19-23,26-28H,3,6,8-15H2,1-2,4-5H3/b16-7+/t17-,19+,20+,21-,22-,23-,24+,25+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H42O3 |
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| Average Mass | 390.6080 Da |
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| Monoisotopic Mass | 390.31340 Da |
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| IUPAC Name | (1R,3S,4R,7S,9S,11S,12R)-12-[(2S,5E)-7-hydroxy-6-methylhept-5-en-2-yl]-1,4-dimethyl-8-methylidenetricyclo[9.3.0.0^{3,7}]tetradecane-4,9-diol |
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| Traditional Name | (1R,3S,4R,7S,9S,11S,12R)-12-[(2S,5E)-7-hydroxy-6-methylhept-5-en-2-yl]-1,4-dimethyl-8-methylidenetricyclo[9.3.0.0^{3,7}]tetradecane-4,9-diol |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@@]1(CC[C@]2(C)C[C@@]3([H])[C@]([H])(CC[C@@]3(C)O)C(=C)[C@@H](O)C[C@@]12[H])[C@@H](C)CC\C=C(/C)CO |
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| InChI Identifier | InChI=1S/C25H42O3/c1-16(15-26)7-6-8-17(2)19-9-11-24(4)14-22-20(10-12-25(22,5)28)18(3)23(27)13-21(19)24/h7,17,19-23,26-28H,3,6,8-15H2,1-2,4-5H3/b16-7+/t17-,19+,20+,21-,22-,23-,24+,25+/m0/s1 |
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| InChI Key | JQMYMLHCBLYMIH-CZPUOXQQSA-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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| NOESY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600.0, Chloroform-d, simulated) | epoynton@sfu.ca | Not Available | Not Available | 2026-02-05 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 150.0, Chloroform-d, simulated) | epoynton@sfu.ca | Not Available | Not Available | 2026-02-05 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600.203706235, CDCl3, simulated) | 1210751893@qq.com | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum |
| | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Aspergillus undulatus | | | | Aspergillus undulatus | | |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Sesterterpenoids |
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| Direct Parent | Ophiobolane sesterterpenoids |
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| Alternative Parents | |
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| Substituents | - Ophiobolane sesterterpenoid
- Long chain fatty alcohol
- Fatty alcohol
- Fatty acyl
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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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