Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-08-13 19:32:00 UTC |
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Update Date | 2023-02-21 17:17:02 UTC |
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HMDB ID | HMDB0004476 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Anatabine |
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Description | Anatabine is one of the minor alkaloids found in plants in the family Solanaceae, which includes the tobacco plant and tomato. Commercial tobacco plants typically produce alkaloids at levels between 2% and 4% of total dry weight, with nicotine accounting for about 90% of the total alkaloid content, and the related compounds anabatine, nornicotine, and anabasine making up nearly all the rest. These compounds are thought to be biologically active, and part of plants' natural defense system against insects. It belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Anatabine is tobacco alkaloid in urine of smokers and smokeless tobacco users (PMID: 8245163 ). This Nicotine-related alkaloid is an inhibitor of human cytochrome P-450 2A6 (PMID:14757175 ). |
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Structure | C1N[C@@H](CC=C1)C1=CN=CC=C1 InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1 |
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Synonyms | Value | Source |
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(-)-Anatabine | Kegg |
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Chemical Formula | C10H12N2 |
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Average Molecular Weight | 160.2157 |
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Monoisotopic Molecular Weight | 160.100048394 |
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IUPAC Name | (2S)-1,2,3,6-tetrahydro-2,3'-bipyridine |
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Traditional Name | anatabine |
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CAS Registry Number | 581-49-7 |
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SMILES | C1N[C@@H](CC=C1)C1=CN=CC=C1 |
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InChI Identifier | InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1 |
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InChI Key | SOPPBXUYQGUQHE-JTQLQIEISA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Amines |
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Direct Parent | Aralkylamines |
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Alternative Parents | |
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Substituents | - Aralkylamine
- Pyridine
- Hydropyridine
- Heteroaromatic compound
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Secondary aliphatic amine
- Organopnictogen compound
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | 145.5 °C | Not Available | Water Solubility | 1000 mg/mL | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Anatabine,1TMS,isomer #1 | C[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C1 | 1594.2 | Semi standard non polar | 33892256 | Anatabine,1TMS,isomer #1 | C[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C1 | 1575.2 | Standard non polar | 33892256 | Anatabine,1TMS,isomer #1 | C[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C1 | 2044.3 | Standard polar | 33892256 | Anatabine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C1 | 1767.9 | Semi standard non polar | 33892256 | Anatabine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C1 | 1790.3 | Standard non polar | 33892256 | Anatabine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CC=CC[C@H]1C1=CC=CN=C1 | 2231.0 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Anatabine GC-MS (Non-derivatized) - 70eV, Positive | splash10-07cu-1900000000-83089eec362cad1f93f6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Anatabine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Anatabine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 10V, Positive-QTOF | splash10-03di-0900000000-972f6de458718e02613b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 20V, Positive-QTOF | splash10-03e9-1900000000-7baac9dff046273f5a28 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 40V, Positive-QTOF | splash10-0udl-9200000000-f060db2ea029ecd78a78 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 10V, Negative-QTOF | splash10-0a4i-0900000000-32258a0e4b3989d0533f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 20V, Negative-QTOF | splash10-0a4i-0900000000-ffc8f788de9331662424 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 40V, Negative-QTOF | splash10-004i-7900000000-cac0a5ea86d517e75411 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 10V, Negative-QTOF | splash10-056r-9700000000-4ed7ee7465de65e91100 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 20V, Negative-QTOF | splash10-056r-9400000000-c2cb4e83d6aa78ce7b11 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 40V, Negative-QTOF | splash10-004i-9200000000-0e0e70179caacf58851b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 10V, Positive-QTOF | splash10-03di-0900000000-ec9dd3a4861a20c6f98c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 20V, Positive-QTOF | splash10-03di-0900000000-d43f6eaf3f1dd72eec34 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Anatabine 40V, Positive-QTOF | splash10-053r-5900000000-19a118d5150f72469050 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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