Record Information |
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Version | 1.0 |
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Created at | 2022-04-29 04:04:06 UTC |
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Updated at | 2022-04-29 04:04:07 UTC |
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NP-MRD ID | NP0083010 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (+)-Argenteanone D |
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Description | (1S,3R,8S,11S,12S,15R,16R)-15-[(2S,3S,4S,5S)-2-ethoxy-4-hydroxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-one 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. (+)-Argenteanone D is found in Aglaia argentea . It was first documented in 2022 (PMID: 35490355). Based on a literature review a significant number of articles have been published on (1S,3R,8S,11S,12S,15R,16R)-15-[(2S,3S,4S,5S)-2-ethoxy-4-hydroxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-one (PMID: 35490354) (PMID: 35490353) (PMID: 35490352) (PMID: 35490351). |
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Structure | CCO[C@H]1O[C@@H](C=C(C)C)[C@@H](O)[C@@H]1[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C InChI=1S/C32H50O4/c1-8-35-27-25(26(34)21(36-27)17-19(2)3)20-11-13-30(7)23-10-9-22-28(4,5)24(33)12-14-31(22)18-32(23,31)16-15-29(20,30)6/h17,20-23,25-27,34H,8-16,18H2,1-7H3/t20-,21+,22-,23+,25+,26-,27+,29-,30+,31-,32+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C32H50O4 |
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Average Mass | 498.7480 Da |
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Monoisotopic Mass | 498.37091 Da |
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IUPAC Name | (1S,3R,8S,11S,12S,15R,16R)-15-[(2S,3S,4S,5S)-2-ethoxy-4-hydroxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-one |
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Traditional Name | (1S,3R,8S,11S,12S,15R,16R)-15-[(2S,3S,4S,5S)-2-ethoxy-4-hydroxy-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-one |
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CAS Registry Number | Not Available |
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SMILES | CCO[C@H]1O[C@@H](C=C(C)C)[C@@H](O)[C@@H]1[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C |
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InChI Identifier | InChI=1S/C32H50O4/c1-8-35-27-25(26(34)21(36-27)17-19(2)3)20-11-13-30(7)23-10-9-22-28(4,5)24(33)12-14-31(22)18-32(23,31)16-15-29(20,30)6/h17,20-23,25-27,34H,8-16,18H2,1-7H3/t20-,21+,22-,23+,25+,26-,27+,29-,30+,31-,32+/m1/s1 |
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InChI Key | LLPHQTBJAXCIQA-JERFHGEDSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | 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
- Cycloartanol-skeleton
- Cycloartane-skeleton
- 9b,19-cyclo-lanostane-skeleton
- 22-hydroxysteroid
- 3-oxo-5-beta-steroid
- Oxosteroid
- Hydroxysteroid
- 3-oxosteroid
- Steroid
- Monosaccharide
- Tetrahydrofuran
- Cyclic ketone
- Secondary alcohol
- Ketone
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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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