| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-05 02:08:55 UTC |
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| Updated at | 2022-09-05 02:08:55 UTC |
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| NP-MRD ID | NP0206057 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | n-[(1r,3s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]ethanimidic acid |
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| Description | N-Acetylnorloline belongs to the class of organic compounds known as loline alkaloids and derivatives. These are alkaloids with a structure characterized by a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species. n-[(1r,3s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]ethanimidic acid is found in Epichloe uncinata. n-[(1r,3s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]ethanimidic acid was first documented in 2015 (PMID: 26550846). Based on a literature review a small amount of articles have been published on N-Acetylnorloline (PMID: 35482316) (PMID: 32455703) (PMID: 29537853) (PMID: 28723242). |
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| Structure | CC(O)=N[C@H]1[C@H]2CN3CC[C@H](O2)C13 InChI=1S/C9H14N2O2/c1-5(12)10-8-7-4-11-3-2-6(13-7)9(8)11/h6-9H,2-4H2,1H3,(H,10,12)/t6-,7+,8-,9?/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C9H14N2O2 |
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| Average Mass | 182.2230 Da |
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| Monoisotopic Mass | 182.10553 Da |
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| IUPAC Name | N-[(1R,3S)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]ethanimidic acid |
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| Traditional Name | N-[(1R,3S)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]ethanimidic acid |
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| CAS Registry Number | Not Available |
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| SMILES | CC(O)=N[C@H]1[C@H]2CN3CC[C@H](O2)C13 |
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| InChI Identifier | InChI=1S/C9H14N2O2/c1-5(12)10-8-7-4-11-3-2-6(13-7)9(8)11/h6-9H,2-4H2,1H3,(H,10,12)/t6-,7+,8-,9?/m0/s1 |
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| InChI Key | BWGXNGORZPWYGZ-KRBWIIOGSA-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 loline alkaloids and derivatives. These are alkaloids with a structure characterized by a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Loline alkaloids and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Loline alkaloids and derivatives |
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| Alternative Parents | |
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| Substituents | - Loline
- Pyrrolizidine
- Para-oxazepine
- Morpholine
- Oxazinane
- N-alkylpyrrolidine
- Acetamide
- Oxolane
- Pyrrolidine
- Amino acid or derivatives
- Carboxamide group
- Tertiary aliphatic amine
- Tertiary amine
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Dialkyl ether
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- 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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| General References | - Panth N, Wenger ES, Krebs C, Bollinger JM Jr, Grossman RB: Synthesis of 6,6- and 7,7-Difluoro-1-acetamidopyrrolizidines and Their Oxidation Catalyzed by the Nonheme Fe Oxygenase LolO. Chembiochem. 2022 Jul 5;23(13):e202200081. doi: 10.1002/cbic.202200081. Epub 2022 May 17. [PubMed:35482316 ]
- Cagnano G, Vazquez-de-Aldana BR, Asp T, Roulund N, Jensen CS, Soto-Barajas MC: Determination of Loline Alkaloids and Mycelial Biomass in Endophyte-Infected Schedonorus Pratensis by Near-Infrared Spectroscopy and Chemometrics. Microorganisms. 2020 May 21;8(5). pii: microorganisms8050776. doi: 10.3390/microorganisms8050776. [PubMed:32455703 ]
- Pan J, Bhardwaj M, Zhang B, Chang WC, Schardl CL, Krebs C, Grossman RB, Bollinger JM Jr: Installation of the Ether Bridge of Lolines by the Iron- and 2-Oxoglutarate-Dependent Oxygenase, LolO: Regio- and Stereochemistry of Sequential Hydroxylation and Oxacyclization Reactions. Biochemistry. 2018 Apr 10;57(14):2074-2083. doi: 10.1021/acs.biochem.8b00157. Epub 2018 Mar 29. [PubMed:29537853 ]
- Shymanovich T, Charlton ND, Musso AM, Scheerer J, Cech NB, Faeth SH, Young CA: Interspecific and intraspecific hybrid Epichloe species symbiotic with the North American native grass Poa alsodes. Mycologia. 2017 May-Jun;109(3):459-474. doi: 10.1080/00275514.2017.1340779. Epub 2017 Jun 26. [PubMed:28723242 ]
- Moore JR, Pratley JE, Mace WJ, Weston LA: Variation in Alkaloid Production from Genetically Diverse Lolium Accessions Infected with Epichloe Species. J Agric Food Chem. 2015 Dec 9;63(48):10355-65. doi: 10.1021/acs.jafc.5b03089. Epub 2015 Nov 23. [PubMed:26550846 ]
- LOTUS database [Link]
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