| Record Information |
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| Version | 2.0 |
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| Created at | 2024-07-10 10:01:29 UTC |
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| Updated at | 2026-02-20 18:07:07 UTC |
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| NP-MRD ID | NP0333586 |
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| Natural Product DOI | https://doi.org/10.57994/3061 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Undobolin C |
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| Description | Undobolin C 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 C was first documented in 2024 (PMID: 39051441). Based on a literature review very few articles have been published on Undobolin C. |
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| Structure | [H][C@@]1(CC[C@]2(C)C[C@@]3(O)[C@H](C)C[C@@H](O)[C@]3([H])\C(CO)=C/C[C@@]12[H])[C@@H](C)\C=C\C=C(C)C InChI=1S/C25H40O3/c1-16(2)7-6-8-17(3)20-11-12-24(5)15-25(28)18(4)13-22(27)23(25)19(14-26)9-10-21(20)24/h6-9,17-18,20-23,26-28H,10-15H2,1-5H3/b8-6+,19-9-/t17-,18+,20+,21-,22+,23-,24+,25+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H40O3 |
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| Average Mass | 388.5920 Da |
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| Monoisotopic Mass | 388.29775 Da |
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| IUPAC Name | (1R,3R,6R,7S,9E,11S,12R,14R)-10-(hydroxymethyl)-3,14-dimethyl-6-[(2S,3E)-6-methylhepta-3,5-dien-2-yl]tricyclo[9.3.0.0^{3,7}]tetradec-9-ene-1,12-diol |
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| Traditional Name | (1R,3R,6R,7S,9E,11S,12R,14R)-10-(hydroxymethyl)-3,14-dimethyl-6-[(2S,3E)-6-methylhepta-3,5-dien-2-yl]tricyclo[9.3.0.0^{3,7}]tetradec-9-ene-1,12-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(O)[C@H](C)C[C@@H](O)[C@]3([H])\C(CO)=C/C[C@@]12[H])[C@@H](C)\C=C\C=C(C)C |
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| InChI Identifier | InChI=1S/C25H40O3/c1-16(2)7-6-8-17(3)20-11-12-24(5)15-25(28)18(4)13-22(27)23(25)19(14-26)9-10-21(20)24/h6-9,17-18,20-23,26-28H,10-15H2,1-5H3/b8-6+,19-9-/t17-,18+,20+,21-,22+,23-,24+,25+/m0/s1 |
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| InChI Key | AYXSBUZARWHXSN-OUXMSWFVSA-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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| ROESY NMR | [1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental) | [email protected] | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental) | [email protected] | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental) | [email protected] | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental) | [email protected] | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D_DEPT NMR | 13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental) | [email protected] | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, CDCl3, experimental) | [email protected] | Huazhong University if Science and technology | Yuyi Zheng | 2024-07-10 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | [email protected] | 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, 400.0, Chloroform-d, simulated) | [email protected] | Not Available | Not Available | 2026-02-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100.0, Chloroform-d, simulated) | [email protected] | Not Available | Not Available | 2026-02-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400.132470967, CDCl3, simulated) | [email protected] | 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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