Record Information |
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Version | 1.0 |
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Created at | 2022-09-09 22:46:00 UTC |
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Updated at | 2022-09-09 22:46:00 UTC |
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NP-MRD ID | NP0291608 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,7as)-hexahydro-1h-pyrrolizin-1-ylmethyl (2r)-2,3-dihydroxy-2-isopropylbutanoate |
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Description | Trachelanthamine belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. (1s,7as)-hexahydro-1h-pyrrolizin-1-ylmethyl (2r)-2,3-dihydroxy-2-isopropylbutanoate is found in Cynoglossum creticum, Eupatorium cannabinum, Gastrocotyle hispida, Praxelis clematidea and Trachelanthus korolkowii. It was first documented in 2004 (PMID: 15595537). Based on a literature review a small amount of articles have been published on Trachelanthamine (PMID: 31154085) (PMID: 17320124) (PMID: 15386579). |
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Structure | CC(C)[C@@](O)(C(C)O)C(=O)OC[C@H]1CCN2CCC[C@@H]12 InChI=1S/C15H27NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h10-13,17,19H,4-9H2,1-3H3/t11?,12-,13+,15-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C15H27NO4 |
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Average Mass | 285.3840 Da |
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Monoisotopic Mass | 285.19401 Da |
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IUPAC Name | [(1S,7aS)-hexahydro-1H-pyrrolizin-1-yl]methyl (2R)-2,3-dihydroxy-2-(propan-2-yl)butanoate |
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Traditional Name | (1S,7aS)-hexahydro-1H-pyrrolizin-1-ylmethyl (2R)-2,3-dihydroxy-2-isopropylbutanoate |
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CAS Registry Number | Not Available |
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SMILES | CC(C)[C@@](O)(C(C)O)C(=O)OC[C@H]1CCN2CCC[C@@H]12 |
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InChI Identifier | InChI=1S/C15H27NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h10-13,17,19H,4-9H2,1-3H3/t11?,12-,13+,15-/m1/s1 |
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InChI Key | BWQSLRZZOVFVHJ-VYHDIPPYSA-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 pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrrolizidines |
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Sub Class | Not Available |
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Direct Parent | Pyrrolizidines |
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Alternative Parents | |
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Substituents | - Pyrrolizidine
- Beta-hydroxy acid
- Fatty acid ester
- Hydroxy acid
- N-alkylpyrrolidine
- Fatty acyl
- Pyrrolidine
- Tertiary alcohol
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Amino acid or derivatives
- 1,2-diol
- Carboxylic acid ester
- Azacycle
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Amine
- Hydrocarbon derivative
- 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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General References | - Mroczek T, Ndjoko K, Glowniak K, Hostettmann K: On-line structure characterization of pyrrolizidine alkaloids in Onosma stellulatum and Emilia coccinea by liquid chromatography-ion-trap mass spectrometry. J Chromatogr A. 2004 Nov 12;1056(1-2):91-7. [PubMed:15595537 ]
- Louisse J, Rijkers D, Stoopen G, Holleboom WJ, Delagrange M, Molthof E, Mulder PPJ, Hoogenboom RLAP, Audebert M, Peijnenburg AACM: Determination of genotoxic potencies of pyrrolizidine alkaloids in HepaRG cells using the gammaH2AX assay. Food Chem Toxicol. 2019 Sep;131:110532. doi: 10.1016/j.fct.2019.05.040. Epub 2019 May 30. [PubMed:31154085 ]
- Frolich C, Ober D, Hartmann T: Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species. Phytochemistry. 2007 Apr;68(7):1026-37. doi: 10.1016/j.phytochem.2007.01.002. Epub 2007 Feb 22. [PubMed:17320124 ]
- Mroczek T, Baj S, Chrobok A, Glowniak K: Screening for pyrrolizidine alkaloids in plant materials by electron ionization RP-HPLC-MS with thermabeam interface. Biomed Chromatogr. 2004 Nov;18(9):745-51. doi: 10.1002/bmc.388. [PubMed:15386579 ]
- LOTUS database [Link]
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