| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 15:00:00 UTC |
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| Updated at | 2022-09-04 15:00:01 UTC |
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| NP-MRD ID | NP0196847 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1s,2r,5r,9s,10s)-5-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one |
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| Description | 3Alpha-hydroxylupanine 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. (1s,2r,5r,9s,10s)-5-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecan-6-one is found in Ammopiptanthus mongolicus and Leontice leontopetalum. Based on a literature review very few articles have been published on 3alpha-hydroxylupanine. |
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| Structure | O[C@@H]1CC[C@@H]2[C@H]3C[C@@H](CN2C1=O)[C@@H]1CCCCN1C3 InChI=1S/C15H24N2O2/c18-14-5-4-13-10-7-11(9-17(13)15(14)19)12-3-1-2-6-16(12)8-10/h10-14,18H,1-9H2/t10-,11-,12-,13+,14+/m0/s1 |
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| Synonyms | | Value | Source |
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| 3a-Hydroxylupanine | Generator | | 3Α-hydroxylupanine | Generator |
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| Chemical Formula | C15H24N2O2 |
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| Average Mass | 264.3690 Da |
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| Monoisotopic Mass | 264.18378 Da |
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| IUPAC Name | (1S,2R,5R,9S,10S)-5-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one |
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| Traditional Name | (1S,2R,5R,9S,10S)-5-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-6-one |
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| CAS Registry Number | Not Available |
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| SMILES | O[C@@H]1CC[C@@H]2[C@H]3C[C@@H](CN2C1=O)[C@@H]1CCCCN1C3 |
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| InChI Identifier | InChI=1S/C15H24N2O2/c18-14-5-4-13-10-7-11(9-17(13)15(14)19)12-3-1-2-6-16(12)8-10/h10-14,18H,1-9H2/t10-,11-,12-,13+,14+/m0/s1 |
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| InChI Key | FROKOSJUHZENQC-QSLWVIQJSA-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 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
- Amino acid or derivatives
- Carboxamide group
- Lactam
- Secondary alcohol
- Tertiary amine
- Tertiary aliphatic amine
- Carboxylic acid derivative
- Azacycle
- Organoheterocyclic compound
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- 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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