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Showing NP-Card for 2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol (NP0220445)

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Record Information
Version2.0
Created at2022-09-05 21:45:23 UTC
Updated at2022-09-05 21:45:23 UTC
NP-MRD IDNP0220445
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
DescriptionN-Methyl-1-deoxynojirimycin, also known as N-methylmoranolin 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 very strong basic compound (based on its pKa). Outside of the human body, N-Methyl-1-deoxynojirimycin has been detected, but not quantified in, fruits. 2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol is found in Morus alba and Morus australis. This could make N-methyl-1-deoxynojirimycin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)


  Mrv0541 05061308242D          

 12 12  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
M  END
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3D MOL for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)

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3D SDF for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)

  Mrv0541 05061308242D          

 12 12  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220445

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC(O)C(O)C(O)C1CO

> <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

> <INCHI_KEY>
AAKDPDFZMNYDLR-UHFFFAOYSA-N

> <FORMULA>
C7H15NO4

> <MOLECULAR_WEIGHT>
177.1983

> <EXACT_MASS>
177.100107973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
17.82190332981238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol

> <ALOGPS_LOGP>
-1.95

> <JCHEM_LOGP>
-2.5026952456666667

> <ALOGPS_LOGS>
0.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.033236454649959

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.9024846956493

> <JCHEM_PKA_STRONGEST_BASIC>
7.782921312802211

> <JCHEM_POLAR_SURFACE_AREA>
84.16000000000001

> <JCHEM_REFRACTIVITY>
41.869099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)
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PDB for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    5    8                                                       
CONECT    3    4    9                                                       
CONECT    4    3    6    8                                                  
CONECT    5    2    7   10                                                  
CONECT    6    4    7   11                                                  
CONECT    7    5    6   12                                                  
CONECT    8    1    2    4                                                  
CONECT    9    3                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)
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SMILES for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)
CN1CC(O)C(O)C(O)C1CO
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INCHI for NP0220445 (2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol)
InChI=1S/C7H15NO4/c1-8-2-5(10)7(12)6(11)4(8)3-9/h4-7,9-12H,2-3H2,1H3
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Synonyms
ValueSource
1,5-Dideoxy-1,5-(methylimino)-D-glucitolHMDB
1,5-Dideoxy-1,5-(methylimino)-D-glucitol, 9ciHMDB
1,5-Dideoxy-1,5-imino-1-methyl-D-sorbitolHMDB
MednjHMDB
N-Methyl-DNJHMDB
N-MethyldeoxynojirimycinHMDB
N-MethyldesoxynojirimycinHMDB
N-MethylmoranolinHMDB
N-MethylmoranolineHMDB
NMDNJHMDB
N-Methyl-1-deoxynojirimycinMeSH
N-Methyldeoxy-nojirimycinMeSH
MOR-14MeSH
Chemical FormulaC7H15NO4
Average Mass177.1983 Da
Monoisotopic Mass177.10011 Da
IUPAC Name2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
Traditional Name2-(hydroxymethyl)-1-methylpiperidine-3,4,5-triol
CAS Registry NumberNot Available
SMILES
CN1CC(O)C(O)C(O)C1CO
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
InChI KeyAAKDPDFZMNYDLR-UHFFFAOYSA-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 australisLOTUS 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
Polarizability17.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035360  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014032  
KNApSAcK IDNot Available
Chemspider ID4228  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4381  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]