| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 23:59:05 UTC |
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| Updated at | 2022-09-02 23:59:05 UTC |
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| NP-MRD ID | NP0164987 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (r)-stylopine |
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| Description | L-Tetrahydrocoptisine, also known as stylopin, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. (r)-stylopine is found in Corydalis intermedia, Corydalis saxicola and Fumaria vaillantii. (r)-stylopine was first documented in 1989 (PMID: 2576175). Based on a literature review very few articles have been published on l-Tetrahydrocoptisine (PMID: 7515744). |
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| Structure | C1OC2=C(O1)C=C1[C@H]3CC4=C(CN3CCC1=C2)C1=C(OCO1)C=C4 InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m1/s1 |
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| Synonyms | | Value | Source |
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| (12BS)-6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine | MeSH | | 6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizine | MeSH | | Stylopin | MeSH | | Stylopine, (S)-isomer | MeSH | | (-)-Stylopine | MeSH | | Stylopine, 14C-labeled, (+,-)-isomer | MeSH | | (+-)-Tetrahydrocoptisine | MeSH | | (S)-Stylopine | MeSH | | (+-)Stylopine | MeSH | | (-)-Tetrahydrocoptisine | MeSH | | Stylopine | MeSH | | Tetrahydrocoptisine | MeSH |
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| Chemical Formula | C19H17NO4 |
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| Average Mass | 323.3480 Da |
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| Monoisotopic Mass | 323.11576 Da |
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| IUPAC Name | (1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{15,23}.0^{16,20}]tetracosa-2(10),3,8,15(23),16(20),21-hexaene |
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| Traditional Name | (1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{15,23}.0^{16,20}]tetracosa-2(10),3,8,15(23),16(20),21-hexaene |
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| CAS Registry Number | Not Available |
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| SMILES | C1OC2=C(O1)C=C1[C@H]3CC4=C(CN3CCC1=C2)C1=C(OCO1)C=C4 |
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| InChI Identifier | InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m1/s1 |
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| InChI Key | UXYJCYXWJGAKQY-OAHLLOKOSA-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, 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 protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Protoberberine alkaloids and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Protoberberine alkaloids and derivatives |
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| Alternative Parents | |
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| Substituents | - Protoberberine skeleton
- Tetrahydroprotoberberine skeleton
- Tetrahydroisoquinoline
- Benzodioxole
- Aralkylamine
- Benzenoid
- Tertiary amine
- Tertiary aliphatic amine
- Acetal
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Amine
- Organic nitrogen compound
- 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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