| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-02 06:38:03 UTC |
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| Updated at | 2022-09-02 06:38:04 UTC |
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| NP-MRD ID | NP0150507 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | n-methyldeoxynojirimycin |
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| Description | N-methyl-1-deoxynojirimycin, also known as MOR-14 or mednj, belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. N-methyl-1-deoxynojirimycin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. n-methyldeoxynojirimycin is found in Morus alba and Morus bombycis. n-methyldeoxynojirimycin was first documented in 2001 (PMID: 11429386). Based on a literature review a small amount of articles have been published on N-methyl-1-deoxynojirimycin (PMID: 33626396) (PMID: 29179061) (PMID: 20565474) (PMID: 17080688). |
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| Structure | CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO InChI=1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3/t4-,5+,6-,7-/m1/s1 |
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| Synonyms | | Value | Source |
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| MeDNJ | ChEBI | | MOR-14 | ChEBI | | N-Methyl-DNJ | ChEBI | | N-Methyl-duvoglustat | ChEBI | | N-Methyldeoxynojirimycin | ChEBI | | N-Methyldesoxynojirimycin | ChEBI | | N-Methyldeoxy-nojirimycin | MeSH | | 1,5-Dideoxy-1,5-(methylimino)-D-glucitol | MeSH |
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| Chemical Formula | C7H15NO4 |
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| Average Mass | 177.2000 Da |
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| Monoisotopic Mass | 177.10011 Da |
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| IUPAC Name | (2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol |
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| Traditional Name | (2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol |
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| CAS Registry Number | Not Available |
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| SMILES | CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO |
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| InChI Identifier | InChI=1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3/t4-,5+,6-,7-/m1/s1 |
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| InChI Key | AAKDPDFZMNYDLR-XZBKPIIZSA-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 piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Piperidines |
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| Sub Class | Not Available |
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| Direct Parent | Piperidines |
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| Alternative Parents | |
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| Substituents | - Piperidine
- 1,2-aminoalcohol
- Secondary alcohol
- Tertiary aliphatic amine
- Tertiary amine
- Polyol
- Azacycle
- Organic nitrogen compound
- Hydrocarbon derivative
- Primary alcohol
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic 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 | - Olivero-Verbel J, De la Parra-Guerra A, Caballero-Gallardo K, Sierra-Marquez L, Fuentes-Lopez K, Franco-Marmolejo J, Jannasch AS, Sepulveda MS, Stashenko E: The aqueous extract of Fridericia chica grown in northern Colombia ameliorates toxicity induced by Tergitol on Caenorhabditis elegans. Comp Biochem Physiol C Toxicol Pharmacol. 2021 Jun;244:109026. doi: 10.1016/j.cbpc.2021.109026. Epub 2021 Feb 21. [PubMed:33626396 ]
- Liang T, Liu S, Wang F, Gu J, Lu Y, Chen W, Li C, Zheng Y, Peng G: A UPLC-MS/MS method for simultaneous determination of 1-deoxynojirimycin and N-methyl-1-deoxynojirimycin in rat plasma and its application in pharmacokinetic and absolute bioavailability studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jan 1;1072:205-210. doi: 10.1016/j.jchromb.2017.10.055. Epub 2017 Nov 4. [PubMed:29179061 ]
- Zhao Y, Zhou Y, O' Boyle KM, Murphy PV: Biological study of the angiogenesis inhibitor N-(8-(3-ethynylphenoxy)octyl-1-deoxynojirimycin. Chem Biol Drug Des. 2010 Jun;75(6):570-7. doi: 10.1111/j.1747-0285.2010.00968.x. [PubMed:20565474 ]
- Sakai R, Kamiya H: 1-Deoxynojirimycin derivatives from the marine sponge Lendenfeldia chondrodes. J Antibiot (Tokyo). 2006 Aug;59(8):507-11. doi: 10.1038/ja.2006.71. [PubMed:17080688 ]
- Arai M, Minatoguchi S, Kumada H, Uno Y, Nishida Y, Hashimoto K, Wang N, Takemura G, Fujiwara T, Higashioka M, Kuwano K, Fujiwara H: Role of protein kinase C in the reduction of infarct size by N-methyl-1-deoxynojirimycin, an alpha-1,6-glucosidase inhibitor. Br J Pharmacol. 2001 Jul;133(5):635-42. doi: 10.1038/sj.bjp.0704107. [PubMed:11429386 ]
- LOTUS database [Link]
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