Record Information |
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Version | 2.0 |
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Created at | 2024-02-15 20:01:39 UTC |
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Updated at | 2024-09-03 04:19:26 UTC |
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NP-MRD ID | NP0332505 |
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Natural Product DOI | https://doi.org/10.57994/1758 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Rubescin K |
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Description | Rubescin K belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review very few articles have been published on Rubescin K. |
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Structure | [H][C@]12[C@H]3OC[C@]1(C)[C@@H](O)[C@H](Cl)C(=O)[C@]2(C)[C@]12O[C@H]1C[C@@]1(C)[C@@H](C[C@H]4O[C@@]14[C@]2(C)[C@@H]3OC(=O)C1=CC=CC=C1)C1=COC=C1 InChI=1S/C33H35ClO8/c1-28-15-39-22-23(28)30(3,25(36)21(34)24(28)35)33-20(42-33)13-29(2)18(17-10-11-38-14-17)12-19-32(29,41-19)31(33,4)26(22)40-27(37)16-8-6-5-7-9-16/h5-11,14,18-24,26,35H,12-13,15H2,1-4H3/t18-,19+,20-,21-,22+,23-,24-,26+,28-,29-,30+,31-,32+,33+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C33H35ClO8 |
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Average Mass | 595.0900 Da |
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Monoisotopic Mass | 594.20205 Da |
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IUPAC Name | (1S,2S,4S,6S,7S,9R,11R,12S,13S,14R,17R,18R,19S,21S)-19-chloro-7-(furan-3-yl)-18-hydroxy-1,6,12,17-tetramethyl-20-oxo-3,10,15-trioxaheptacyclo[12.6.1.0^{2,4}.0^{2,12}.0^{6,11}.0^{9,11}.0^{17,21}]henicosan-13-yl benzoate |
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Traditional Name | (1S,2S,4S,6S,7S,9R,11R,12S,13S,14R,17R,18R,19S,21S)-19-chloro-7-(furan-3-yl)-18-hydroxy-1,6,12,17-tetramethyl-20-oxo-3,10,15-trioxaheptacyclo[12.6.1.0^{2,4}.0^{2,12}.0^{6,11}.0^{9,11}.0^{17,21}]henicosan-13-yl benzoate |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]12[C@H]3OC[C@]1(C)[C@@H](O)[C@H](Cl)C(=O)[C@]2(C)[C@]12O[C@H]1C[C@@]1(C)[C@@H](C[C@H]4O[C@@]14[C@]2(C)[C@@H]3OC(=O)C1=CC=CC=C1)C1=COC=C1 |
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InChI Identifier | InChI=1S/C33H35ClO8/c1-28-15-39-22-23(28)30(3,25(36)21(34)24(28)35)33-20(42-33)13-29(2)18(17-10-11-38-14-17)12-19-32(29,41-19)31(33,4)26(22)40-27(37)16-8-6-5-7-9-16/h5-11,14,18-24,26,35H,12-13,15H2,1-4H3/t18-,19+,20-,21-,22+,23-,24-,26+,28-,29-,30+,31-,32+,33+/m0/s1 |
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InChI Key | RQAWJLDAJCGNHS-SEOIWVRASA-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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HMQC NMR | [Proton, Carbon13] NMR Spectrum (2D, 600 MHz, CDCL3, experimental) | kngoto@p.kanazawa-u.ac.jp | Not Available | Not Available | 2024-02-15 | View Spectrum | NOESY NMR | [Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental) | kngoto@p.kanazawa-u.ac.jp | Not Available | Not Available | 2024-02-15 | View Spectrum | 1D NMR | Carbon13 NMR Spectrum (1D, 151 MHz, CDCL3, experimental) | kngoto@p.kanazawa-u.ac.jp | Not Available | Not Available | 2024-02-15 | View Spectrum | HMBC NMR | [Proton, Carbon13] NMR Spectrum (2D, 600 MHz, CDCL3, experimental) | kngoto@p.kanazawa-u.ac.jp | Not Available | Not Available | 2024-02-15 | View Spectrum | 1D NMR | Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental) | kngoto@p.kanazawa-u.ac.jp | Not Available | Not Available | 2024-02-15 | View Spectrum | COSY NMR | [Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental) | kngoto@p.kanazawa-u.ac.jp | Not Available | Not Available | 2024-02-15 | 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 | Not Available |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. |
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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 | Triterpenoids |
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Direct Parent | Limonoids |
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Alternative Parents | |
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Substituents | - Limonoid skeleton
- Thromboxane
- Steroid ester
- Eicosanoid
- Steroid
- Naphthopyran
- Naphthofuran
- Naphthalene
- Benzoate ester
- Benzoic acid or derivatives
- Benzoyl
- Oxepane
- Fatty acid ester
- Fatty acyl
- Benzenoid
- Pyran
- Oxane
- Beta-hydroxy ketone
- Monocyclic benzene moiety
- Alpha-haloketone
- Alpha-chloroketone
- Heteroaromatic compound
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tetrahydrofuran
- Furan
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Halohydrin
- Chlorohydrin
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Ether
- Oxirane
- Dialkyl ether
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organochloride
- Organohalogen compound
- Alkyl halide
- Alkyl chloride
- Alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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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