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Record Information
Version2.0
Created at2022-09-02 06:38:03 UTC
Updated at2022-09-02 06:38:04 UTC
NP-MRD IDNP0150507
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-methyldeoxynojirimycin
DescriptionN-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).
Structure
Thumb
Synonyms
ValueSource
MeDNJChEBI
MOR-14ChEBI
N-Methyl-DNJChEBI
N-Methyl-duvoglustatChEBI
N-MethyldeoxynojirimycinChEBI
N-MethyldesoxynojirimycinChEBI
N-Methyldeoxy-nojirimycinMeSH
1,5-Dideoxy-1,5-(methylimino)-D-glucitolMeSH
Chemical FormulaC7H15NO4
Average Mass177.2000 Da
Monoisotopic Mass177.10011 Da
IUPAC Name(2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
Traditional Name(2R,3R,4R,5S)-2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
CAS Registry NumberNot Available
SMILES
CN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO
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
InChI KeyAAKDPDFZMNYDLR-XZBKPIIZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Morus albaLOTUS Database
Morus bombycisLOTUS Database
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.5ChemAxon
logS0.77ALOGPS
pKa (Strongest Acidic)12.9ChemAxon
pKa (Strongest Basic)7.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area84.16 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.87 m³·mol⁻¹ChemAxon
Polarizability17.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00051703
Chemspider ID83403
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92381
PDB IDNot Available
ChEBI ID166564
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. LOTUS database [Link]