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Showing NP-Card for (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal (NP0189428)

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Record Information
Version2.0
Created at2022-09-04 05:54:26 UTC
Updated at2022-09-04 05:54:27 UTC
NP-MRD IDNP0189428
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal
DescriptionN-Methylglucosamine, also known as photodithazine, belongs to the class of organic compounds known as aminosaccharides. These are saccharides containing a sugar unit that bears an amino group. (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal is found in Streptomyces griseus. (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal was first documented in 1987 (PMID: 3812740). Based on a literature review a small amount of articles have been published on N-Methylglucosamine (PMID: 8431459) (PMID: 8297833).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)


  Mrv1652309042207542D          

 13 12  0  0  1  0            999 V2000
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)

     RDKit          3D

 28 27  0  0  0  0  0  0  0  0999 V2000
   -3.3501    0.1330    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    0.1037   -0.1526 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -0.7762    0.7381 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7477   -2.1495    0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6800   -2.3956   -0.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -0.7130    0.3331 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2979   -1.1393   -0.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    0.6559    0.5882 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1153    1.6424   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2511    0.7635    0.3330 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6157    2.0599    0.7547 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5304    0.7131   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8882    0.9731   -1.3938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4718   -0.4141    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9541   -0.4243   -0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279    1.1832    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9029   -0.2247   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3032   -0.3728    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395   -2.9407    1.2406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7546   -1.4328    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886   -1.8047   -1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593    0.8731    1.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0859    1.3384   -1.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    0.0008    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392    2.6768    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -0.3270   -1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665    1.4602   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482    0.5375   -2.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  3  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  1
  4 19  1  0
  6 20  1  1
  7 21  1  0
  8 22  1  1
  9 23  1  0
 10 24  1  1
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
M  END
Download

3D SDF for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)


  Mrv1652309042207542D          

 13 12  0  0  1  0            999 V2000
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C7H15NO5/c1-8-4(2-9)6(12)7(13)5(11)3-10/h2,4-8,10-13H,3H2,1H3/t4-,5+,6+,7+/m0/s1

> <INCHI_KEY>
LDDMACCNBZAMSG-BDVNFPICSA-N

> <FORMULA>
C7H15NO5

> <MOLECULAR_WEIGHT>
193.199

> <EXACT_MASS>
193.095022587

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
18.689163221988537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal

> <JCHEM_LOGP>
-3.2426619659999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.776633867509439

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.770711996366746

> <JCHEM_PKA_STRONGEST_BASIC>
7.300605340633182

> <JCHEM_POLAR_SURFACE_AREA>
110.02000000000001

> <JCHEM_REFRACTIVITY>
43.7777

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)

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PDB for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.286   3.437   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   1.127   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.286   0.357   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)
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SMILES for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)
CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
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INCHI for NP0189428 ((2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal)
InChI=1S/C7H15NO5/c1-8-4(2-9)6(12)7(13)5(11)3-10/h2,4-8,10-13H,3H2,1H3/t4-,5+,6+,7+/m0/s1
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View in JSmol
Synonyms
ValueSource
N-Methyl glucosamine chlorine e6 saltMeSH
N-Methylglucosamine, (L)-isomerMeSH
PhotodithazineMeSH
Chemical FormulaC7H15NO5
Average Mass193.1990 Da
Monoisotopic Mass193.09502 Da
IUPAC Name(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal
Traditional Name(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal
CAS Registry NumberNot Available
SMILES
CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C7H15NO5/c1-8-4(2-9)6(12)7(13)5(11)3-10/h2,4-8,10-13H,3H2,1H3/t4-,5+,6+,7+/m0/s1
InChI KeyLDDMACCNBZAMSG-BDVNFPICSA-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
Streptomyces griseusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminosaccharides. These are saccharides containing a sugar unit that bears an amino group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentAminosaccharides  
Alternative Parents
Substituents
  • Amino saccharide
    • 

  • Beta-hydroxy aldehyde
    • 

  • Monosaccharide
    • 

  • 1,3-aminoalcohol
    • 

  • Secondary alcohol
    • 

  • Secondary aliphatic amine
    • 

  • Secondary amine
    • 

  • Polyol
    • 

  • Organic nitrogen compound
    • 

  • Primary alcohol
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Aldehyde
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-3.2ChemAxon
pKa (Strongest Acidic)12.77ChemAxon
pKa (Strongest Basic)7.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.02 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.78 m³·mol⁻¹ChemAxon
Polarizability18.69 ųChemAxon
Number of Rings0ChemAxon
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 IDNot Available
Chemspider ID133174  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151093  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Haworth RS, Cragoe EJ Jr, Fliegel L: Amiloride and 5-(N-ethyl-N-isopropyl) amiloride inhibit medium acidification and glucose metabolism by the fission yeast Schizosaccharomyces pombe. Biochim Biophys Acta. 1993 Feb 9;1145(2):266-72. doi:  10.1016/0005-2736(93)90298-e. [PubMed:8431459  ] 
  2. Roder B, Zuhlke A, Widdecke H, Klein J: Synthesis and application of new microcarriers for animal cell culture. Part II: Application of polystyrene microcarriers. J Biomater Sci Polym Ed. 1993;5(1-2):79-88. doi: 10.1163/156856294x00662. [PubMed:8297833  ] 
  3. Humes HD, Hunt DA, White MD: Direct toxic effect of the radiocontrast agent diatrizoate on renal proximal tubule cells. Am J Physiol. 1987 Feb;252(2 Pt 2):F246-55. doi:  10.1152/ajprenal.1987.252.2.F246. [PubMed:3812740  ] 
  4. LOTUS database [Link]