| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-09 12:07:55 UTC |
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| Updated at | 2024-09-03 04:16:52 UTC |
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| NP-MRD ID | NP0284435 |
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| Natural Product DOI | https://doi.org/10.57994/0837 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | cinchonine |
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| Description | 9-Epi-Cinchonidine, also known as cinchonine, belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. cinchonine is found in Cinchona pubescens. Based on a literature review very few articles have been published on 9-epi-Cinchonidine. |
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| Structure | O[C@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)C1=C2C=CC=CC2=NC=C1 InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19-/m0/s1 |
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| Synonyms | | Value | Source |
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| Cinchonine, monohydrochloride, (9S)-isomer | MeSH | | Cinchonine, hexaiodotl(-2) (1:1), (9S)-isomer | MeSH | | Cinchonine, hydrochloride, (9S)-isomer | MeSH | | Cinchonine | MeSH | | Cinchonine, sulfate (2:1), (9S)-isomer | MeSH |
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| Chemical Formula | C19H22N2O |
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| Average Mass | 294.3980 Da |
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| Monoisotopic Mass | 294.17321 Da |
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| IUPAC Name | (S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol |
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| Traditional Name | cinchonine |
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| CAS Registry Number | Not Available |
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| SMILES | O[C@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)C1=C2C=CC=CC2=NC=C1 |
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| InChI Identifier | InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19-/m0/s1 |
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| InChI Key | KMPWYEUPVWOPIM-LSOMNZGLSA-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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| TOCSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | HOMO2DJ NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCL3, experimental) | [email protected] | Not Available | Not Available | 2023-08-23 | View Spectrum |
| | 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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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 cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Cinchona alkaloids |
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| Sub Class | Not Available |
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| Direct Parent | Cinchona alkaloids |
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| Alternative Parents | |
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| Substituents | - Cinchonan-skeleton
- 4-quinolinemethanol
- Quinoline
- Quinuclidine
- Aralkylamine
- Piperidine
- Pyridine
- Benzenoid
- Heteroaromatic compound
- 1,2-aminoalcohol
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Amine
- Alcohol
- Aromatic 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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