| Record Information |
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| Version | 2.0 |
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| Created at | 2024-07-10 10:33:58 UTC |
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| Updated at | 2026-02-17 11:07:46 UTC |
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| NP-MRD ID | NP0333590 |
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| Natural Product DOI | https://doi.org/10.57994/3065 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Undobolin G |
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| Description | Undobolin G 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 G was first documented in 2024 (PMID: 39051441). Based on a literature review very few articles have been published on Undobolin G. |
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| Structure | [H][C@]1(OC1(C)C)\C=C/[C@H](C)[C@@]1([H])CC[C@]2(C)C[C@]3([H])C(C)=CC(=O)[C@@]3([H])\C(CO)=C/C[C@@]12[H] InChI=1S/C25H36O3/c1-15(6-9-22-24(3,4)28-22)18-10-11-25(5)13-19-16(2)12-21(27)23(19)17(14-26)7-8-20(18)25/h6-7,9,12,15,18-20,22-23,26H,8,10-11,13-14H2,1-5H3/b9-6-,17-7-/t15-,18+,19+,20-,22-,23-,25+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H36O3 |
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| Average Mass | 384.5600 Da |
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| Monoisotopic Mass | 384.26645 Da |
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| IUPAC Name | (1R,3S,7R,8E,11S,12R)-12-[(2S,3Z)-4-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl]-8-(hydroxymethyl)-1,4-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-4,8-dien-6-one |
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| Traditional Name | (1R,3S,7R,8E,11S,12R)-12-[(2S,3Z)-4-[(2S)-3,3-dimethyloxiran-2-yl]but-3-en-2-yl]-8-(hydroxymethyl)-1,4-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-4,8-dien-6-one |
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| CAS Registry Number | Not Available |
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| SMILES | [H][C@]1(OC1(C)C)\C=C/[C@H](C)[C@@]1([H])CC[C@]2(C)C[C@]3([H])C(C)=CC(=O)[C@@]3([H])\C(CO)=C/C[C@@]12[H] |
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| InChI Identifier | InChI=1S/C25H36O3/c1-15(6-9-22-24(3,4)28-22)18-10-11-25(5)13-19-16(2)12-21(27)23(19)17(14-26)7-8-20(18)25/h6-7,9,12,15,18-20,22-23,26H,8,10-11,13-14H2,1-5H3/b9-6-,17-7-/t15-,18+,19+,20-,22-,23-,25+/m0/s1 |
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| InChI Key | JEXJZGKULYVFDN-WBBAMFPJSA-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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| 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 | | 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 | | 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 |
| | 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 | 2026-02-17 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100.0, Chloroform-d, simulated) | [email protected] | Not Available | Not Available | 2026-02-17 | 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
- Alpha,beta-unsaturated ketone
- Enone
- Acryloyl-group
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- 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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