| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-27 22:38:50 UTC |
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| Updated at | 2022-04-27 22:38:50 UTC |
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| NP-MRD ID | NP0051263 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Aphylline |
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| Description | 17-Oxosparteine belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. Aphylline is found in Acosmium panamense, Anabasis aphylla, Apis cerana, Argyrolobium frutescens, Argyrolobium lanceolatum, Argyrolobium lunare, Argyrolobium rupestre, Argyrolobium sankeyi, Argyrolobium speciosum, Argyrolobium tomentosum, Argyrolobium velutinum, Cytisus monspessulanus L., Lupinus latifolius, Lupinus hartwegii, Sophora davidii, Sophora griffithii, Virgilia divaricata and Virgilia oroboides. Aphylline was first documented in 2011 (PMID: 22000488). Based on a literature review very few articles have been published on 17-Oxosparteine (PMID: 21760788). |
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| Structure | O=C1[C@H]2C[C@@H](CN3CCCC[C@@H]23)[C@H]2CCCCN12 InChI=1S/C15H24N2O/c18-15-12-9-11(13-5-2-4-8-17(13)15)10-16-7-3-1-6-14(12)16/h11-14H,1-10H2/t11-,12-,13+,14-/m0/s1 |
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| Synonyms | | Value | Source |
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| 17-Oxosparteine monohydrochloride, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomer | MeSH | | 17-Oxosparteine, (7R-(7alpha,7abeta,14alpha,14aalpha))-isomer | MeSH | | 17-Oxosparteine, 7S-(7alpha,7aalpha,14alpha,14abeta)-isomer | MeSH | | 17-Oxosparteine, 7S-(7alpha,7beta,14alpha,14abeta)-isomer | MeSH |
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| Chemical Formula | C15H24N2O |
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| Average Mass | 248.3700 Da |
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| Monoisotopic Mass | 248.18886 Da |
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| IUPAC Name | (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-8-one |
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| Traditional Name | (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-8-one |
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| CAS Registry Number | Not Available |
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| SMILES | O=C1[C@H]2C[C@@H](CN3CCCC[C@@H]23)[C@H]2CCCCN12 |
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| InChI Identifier | InChI=1S/C15H24N2O/c18-15-12-9-11(13-5-2-4-8-17(13)15)10-16-7-3-1-6-14(12)16/h11-14H,1-10H2/t11-,12-,13+,14-/m0/s1 |
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| InChI Key | YQMWQSMYVPLYDI-FQUUOJAGSA-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 sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Lupin alkaloids |
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| Sub Class | Sparteine, lupanine, and related alkaloids |
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| Direct Parent | Sparteine, lupanine, and related alkaloids |
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| Alternative Parents | |
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| Substituents | - Sparteine-lupanine skeleton
- Quinolizidinone
- Quinolizidine
- Delta-lactam
- Piperidinone
- Piperidine
- Tertiary carboxylic acid amide
- Tertiary aliphatic amine
- Tertiary amine
- Amino acid or derivatives
- Carboxamide group
- Lactam
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Amine
- Organic nitrogen compound
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- 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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