Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 17:38:03 UTC |
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Updated at | 2021-06-29 23:50:33 UTC |
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NP-MRD ID | NP0025535 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 25-hydroxy-13(24),17-cheilanthadien-16,19-olide |
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Provided By | JEOL Database |
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Description | 25-Hydroxy-13(24),17-cheilanthadien-16,19-olide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 25-hydroxy-13(24),17-cheilanthadien-16,19-olide is found in Ircinia and Ircinia sp.. It was first documented in 2001 (PMID: 11277743). Based on a literature review very few articles have been published on 25-hydroxy-13(24),17-cheilanthadien-16,19-olide. |
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Structure | [H]OC([H])([H])C1=C([H])C(=O)O[C@]1([H])C([H])([H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H] InChI=1S/C25H38O3/c1-16-7-8-21-24(4,18(16)14-19-17(15-26)13-22(27)28-19)12-9-20-23(2,3)10-6-11-25(20,21)5/h13,18-21,26H,1,6-12,14-15H2,2-5H3/t18-,19-,20+,21+,24+,25+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C25H38O3 |
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Average Mass | 386.5760 Da |
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Monoisotopic Mass | 386.28210 Da |
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IUPAC Name | (5R)-5-{[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-tetradecahydrophenanthren-1-yl]methyl}-4-(hydroxymethyl)-2,5-dihydrofuran-2-one |
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Traditional Name | (5R)-5-{[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-decahydrophenanthren-1-yl]methyl}-4-(hydroxymethyl)-5H-furan-2-one |
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CAS Registry Number | Not Available |
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SMILES | [H]OC([H])([H])C1=C([H])C(=O)O[C@]1([H])C([H])([H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H] |
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InChI Identifier | InChI=1S/C25H38O3/c1-16-7-8-21-24(4,18(16)14-19-17(15-26)13-22(27)28-19)12-9-20-23(2,3)10-6-11-25(20,21)5/h13,18-21,26H,1,6-12,14-15H2,2-5H3/t18-,19-,20+,21+,24+,25+/m1/s1 |
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InChI Key | IDZSBARYKPRHAX-BXWWMEFGSA-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, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, 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 | Species Name | Source | Reference |
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Ircinia | JEOL database | - Buchanan, M. S., et al, J. Nat. Prod. 64, 300 (2001)
| Ircinia sp. | Animalia | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. |
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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 | Terpene lactones |
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Direct Parent | Diterpene lactones |
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Alternative Parents | |
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Substituents | - Diterpene lactone
- Diterpenoid
- Cleistanthane diterpenoid
- Hydrophenanthrene
- Phenanthrene
- 2-furanone
- Dihydrofuran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Primary alcohol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organooxygen 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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