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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015461

Secondary Accession Numbers

HMDB15461

Metabolite Identification

Common Name

Glycodiazine

Description

Glycodiazine is used with diet to lower blood glucose by increasing the secretion of insulin from pancreas and increasing the sensitivity of peripheral tissues to insulin. The mechanism of action of glycodiazine in lowering blood glucose appears to be dependent on stimulating the release of insulin from functioning pancreatic beta cells, and increasing sensitivity of peripheral tissues to insulin. Glycodiazine likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin. It is used for the concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015461
     RDKit          3D
Glycodiazine
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.9527   -0.9131   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0569   -1.2360   -0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8477   -1.5781   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8620   -0.4392   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.8649    0.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664   -0.0020    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -0.4092    1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    0.4295    1.1247 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406    1.6730    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463    2.5497    0.6893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    2.0147    1.4224 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.9276    1.6208    2.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538    3.1907    1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    0.6504    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795    0.8653   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3385   -0.2359   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0796   -1.5165   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359   -1.7226    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6497   -0.6166    1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    2.0574    0.0574 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    1.2868   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9607   -0.6632   -2.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4070   -1.6387   -2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135    0.0792   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.8492    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -2.4830   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2614    0.4286    0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -0.1989   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -1.4087    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    3.4970    0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9890    1.8752   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0100   -0.1334   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -2.3877   -1.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -2.7027    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908   -0.8300    1.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    1.6112   -0.4911 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  2  0
 21  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END

1382
  Mrv0541 02231215242D          

 21 22  0  0  0  0            999 V2000
    3.7935    2.2688    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    1.5543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    2.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  0  0  0  0
  5 18  1  0  0  0  0
  5 21  1  0  0  0  0
  6 12  1  0  0  0  0
  7 12  1  0  0  0  0
  7 19  2  0  0  0  0
  8 12  2  0  0  0  0
  8 20  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 13 18  1  0  0  0  0
 14 17  2  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015461

> <DATABASE_NAME>
hmdb

> <SMILES>
COCCOC1=CN=C(NS(=O)(=O)C2=CC=CC=C2)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H15N3O4S/c1-19-7-8-20-11-9-14-13(15-10-11)16-21(17,18)12-5-3-2-4-6-12/h2-6,9-10H,7-8H2,1H3,(H,14,15,16)

> <INCHI_KEY>
QFWPJPIVLCBXFJ-UHFFFAOYSA-N

> <FORMULA>
C13H15N3O4S

> <MOLECULAR_WEIGHT>
309.341

> <EXACT_MASS>
309.078326673

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.293111988119396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[5-(2-methoxyethoxy)pyrimidin-2-yl]benzenesulfonamide

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.011539988

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.918319801689379

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3934878568972304

> <JCHEM_POLAR_SURFACE_AREA>
90.41000000000001

> <JCHEM_REFRACTIVITY>
77.00719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycodiazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015461
     RDKit          3D
Glycodiazine
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.9527   -0.9131   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0569   -1.2360   -0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8477   -1.5781   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8620   -0.4392   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.8649    0.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664   -0.0020    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -0.4092    1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    0.4295    1.1247 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406    1.6730    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463    2.5497    0.6893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    2.0147    1.4224 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.9276    1.6208    2.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538    3.1907    1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    0.6504    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795    0.8653   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3385   -0.2359   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0796   -1.5165   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359   -1.7226    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6497   -0.6166    1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    2.0574    0.0574 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    1.2868   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9607   -0.6632   -2.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4070   -1.6387   -2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135    0.0792   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.8492    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -2.4830   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2614    0.4286    0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -0.1989   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -1.4087    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    3.4970    0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9890    1.8752   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0100   -0.1334   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -2.3877   -1.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -2.7027    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908   -0.8300    1.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    1.6112   -0.4911 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  2  0
 21  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1382                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.081   4.235   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       5.748  -2.695   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.851   2.901   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.311   5.569   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.080  -5.775   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.748   3.465   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.081   1.155   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414   1.155   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.415   5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   6.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   4.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   7.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -1.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   6.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -0.385   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -7.315   0.000  0.00  0.00           C+0
CONECT    1    3    4    6    9                                             
CONECT    2   13   16                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   18   21                                                       
CONECT    6    1   12                                                       
CONECT    7   12   19                                                       
CONECT    8   12   20                                                       
CONECT    9    1   10   11                                                  
CONECT   10    9   14                                                       
CONECT   11    9   15                                                       
CONECT   12    6    7    8                                                  
CONECT   13    2   18                                                       
CONECT   14   10   17                                                       
CONECT   15   11   17                                                       
CONECT   16    2   19   20                                                  
CONECT   17   14   15                                                       
CONECT   18    5   13                                                       
CONECT   19    7   16                                                       
CONECT   20    8   16                                                       
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015461
HETATM    1  C1  UNL     1       5.953  -0.913  -1.966  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.057  -1.236  -0.640  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.848  -1.578  -0.079  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.862  -0.439  -0.168  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.642  -0.865   0.440  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.566  -0.002   0.491  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.388  -0.409   1.076  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.656   0.430   1.125  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.641   1.673   0.633  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.746   2.550   0.689  1.00  0.00           N  
HETATM   11  S1  UNL     1      -3.199   2.015   1.422  1.00  0.00           S  
HETATM   12  O3  UNL     1      -2.928   1.621   2.871  1.00  0.00           O  
HETATM   13  O4  UNL     1      -4.154   3.191   1.488  1.00  0.00           O  
HETATM   14  C7  UNL     1      -3.922   0.650   0.643  1.00  0.00           C  
HETATM   15  C8  UNL     1      -4.779   0.865  -0.436  1.00  0.00           C  
HETATM   16  C9  UNL     1      -5.338  -0.236  -1.024  1.00  0.00           C  
HETATM   17  C10 UNL     1      -5.080  -1.516  -0.585  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.236  -1.723   0.477  1.00  0.00           C  
HETATM   19  C12 UNL     1      -3.650  -0.617   1.099  1.00  0.00           C  
HETATM   20  N3  UNL     1       0.535   2.057   0.057  1.00  0.00           N  
HETATM   21  C13 UNL     1       1.613   1.287  -0.031  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.961  -0.663  -2.419  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.407  -1.639  -2.578  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.414   0.079  -2.078  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.020  -1.849   1.007  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.461  -2.483  -0.609  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.261   0.429   0.392  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.657  -0.199  -1.235  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.343  -1.409   1.483  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.669   3.497   0.291  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.989   1.875  -0.789  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.010  -0.133  -1.864  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.536  -2.388  -1.068  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.001  -2.703   0.859  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.991  -0.830   1.940  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.537   1.611  -0.491  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6
CONECT    6    7    7   21
CONECT    7    8   29
CONECT    8    9    9
CONECT    9   10   20
CONECT   10   11   30
CONECT   11   12   12   13   13
CONECT   11   14
CONECT   14   15   15   19
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   35
CONECT   20   21   21
CONECT   21   36
END

HMDB0015461
     RDKit          3D
Glycodiazine
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.9527   -0.9131   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0569   -1.2360   -0.6401 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8477   -1.5781   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8620   -0.4392   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.8649    0.4397 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5664   -0.0020    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -0.4092    1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555    0.4295    1.1247 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6406    1.6730    0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463    2.5497    0.6893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1991    2.0147    1.4224 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.9276    1.6208    2.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538    3.1907    1.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    0.6504    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795    0.8653   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3385   -0.2359   -1.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0796   -1.5165   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359   -1.7226    0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6497   -0.6166    1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    2.0574    0.0574 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    1.2868   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9607   -0.6632   -2.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4070   -1.6387   -2.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135    0.0792   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.8492    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4611   -2.4830   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2614    0.4286    0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569   -0.1989   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3433   -1.4087    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    3.4970    0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9890    1.8752   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0100   -0.1334   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -2.3877   -1.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -2.7027    0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9908   -0.8300    1.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    1.6112   -0.4911 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  2  0
 21  6  1  0
 19 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Benzenesulfonamido-5-(2-methoxyethoxy)pyrimidine	ChEBI
Glidiazine	ChEBI
Glymidinum	ChEBI
2-Benzenesulphonamido-5-(2-methoxyethoxy)pyrimidine	Generator
Glymidine	HMDB
N-[5-(2-Methoxyethoxy)pyrimidin-2-yl]benzenesulphonamide	HMDB
Glycodiazine	MeSH

Chemical Formula

C₁₃H₁₅N₃O₄S

Average Molecular Weight

309.341

Monoisotopic Molecular Weight

309.078326673

IUPAC Name

N-[5-(2-methoxyethoxy)pyrimidin-2-yl]benzenesulfonamide

Traditional Name

glycodiazine

CAS Registry Number

339-44-6

SMILES

COCCOC1=CN=C(NS(=O)(=O)C2=CC=CC=C2)N=C1

InChI Identifier

InChI=1S/C13H15N3O4S/c1-19-7-8-20-11-9-14-13(15-10-11)16-21(17,18)12-5-3-2-4-6-12/h2-6,9-10H,7-8H2,1H3,(H,14,15,16)

InChI Key

QFWPJPIVLCBXFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Alkyl aryl ether
Pyrimidine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Dialkyl ether
Organoheterocyclic compound
Azacycle
Ether
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015461)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.12 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.01	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	90.41 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.01 m³·mol⁻¹	ChemAxon
Polarizability	31.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.088	31661259
DarkChem	[M-H]-	170.866	31661259
DeepCCS	[M+H]+	171.095	30932474
DeepCCS	[M-H]-	168.736	30932474
DeepCCS	[M-2H]-	201.623	30932474
DeepCCS	[M+Na]+	177.188	30932474
AllCCS	[M+H]+	170.3	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycodiazine	COCCOC1=CN=C(NS(=O)(=O)C2=CC=CC=C2)N=C1	3651.7	Standard polar	33892256
Glycodiazine	COCCOC1=CN=C(NS(=O)(=O)C2=CC=CC=C2)N=C1	2558.8	Standard non polar	33892256
Glycodiazine	COCCOC1=CN=C(NS(=O)(=O)C2=CC=CC=C2)N=C1	2548.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycodiazine,1TMS,isomer #1	COCCOC1=CN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2)N=C1	2520.7	Semi standard non polar	33892256
Glycodiazine,1TMS,isomer #1	COCCOC1=CN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2)N=C1	2390.8	Standard non polar	33892256
Glycodiazine,1TMS,isomer #1	COCCOC1=CN=C(N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2)N=C1	3696.0	Standard polar	33892256
Glycodiazine,1TBDMS,isomer #1	COCCOC1=CN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2)N=C1	2781.6	Semi standard non polar	33892256
Glycodiazine,1TBDMS,isomer #1	COCCOC1=CN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2)N=C1	2597.4	Standard non polar	33892256
Glycodiazine,1TBDMS,isomer #1	COCCOC1=CN=C(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2)N=C1	3700.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glycodiazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-9770000000-ea6c0b6ca2cdf199cf0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycodiazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycodiazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 10V, Positive-QTOF	splash10-03di-1539000000-cad8a53e4094d40387f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 20V, Positive-QTOF	splash10-0k96-6922000000-cf7c45f02c1c50bf26e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 40V, Positive-QTOF	splash10-02vi-9310000000-6463cc4b55dbc70dc51e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 10V, Negative-QTOF	splash10-0a4i-0149000000-b06862f8e17b75fb66e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 20V, Negative-QTOF	splash10-0kai-1961000000-9d7ab1d9bbe75471d3f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 40V, Negative-QTOF	splash10-003u-4910000000-0bafe7ba5932a7189116	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 10V, Positive-QTOF	splash10-03di-0009000000-454a20f41f470b743b2d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 20V, Positive-QTOF	splash10-03di-0319000000-dd30359a3347b4f1d3e1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 40V, Positive-QTOF	splash10-06vm-4921000000-ec2a33f6dbe52eca5bea	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 10V, Negative-QTOF	splash10-0a4i-0029000000-cf79580c51558359ef5d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 20V, Negative-QTOF	splash10-0zfr-0890000000-1c58185ace70bb715004	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycodiazine 40V, Negative-QTOF	splash10-0bu0-0900000000-dd2cbfd0834f41e05057	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01382	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01382	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01382

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glymidine sodium

METLIN ID

Not Available

PubChem Compound

9565

PDB ID

Not Available

ChEBI ID

1178587

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. ATP-sensitive inward rectifier potassium channel 1

General function:: Involved in inward rectifier potassium channel activity
Specific function:: In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:: KCNJ1
Uniprot ID:: P48048
Molecular weight:: 44794.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Guirgis FK, Ghanem MH, Abdel-Hay MM: Comparative study of the hypoglycaemic and antilipolytic effects of four antidiabetic agents administered i.v. Arzneimittelforschung. 1976;26(3):435-7. [PubMed:134717 ]
Greeley SA, Tucker SE, Naylor RN, Bell GI, Philipson LH: Neonatal diabetes mellitus: a model for personalized medicine. Trends Endocrinol Metab. 2010 Aug;21(8):464-72. doi: 10.1016/j.tem.2010.03.004. Epub 2010 Apr 29. [PubMed:20434356 ]
Pondugula SR, Raveendran NN, Ergonul Z, Deng Y, Chen J, Sanneman JD, Palmer LG, Marcus DC: Glucocorticoid regulation of genes in the amiloride-sensitive sodium transport pathway by semicircular canal duct epithelium of neonatal rat. Physiol Genomics. 2006 Jan 12;24(2):114-23. Epub 2005 Nov 1. [PubMed:16263802 ]
Lu M, Leng Q, Egan ME, Caplan MJ, Boulpaep EL, Giebisch GH, Hebert SC: CFTR is required for PKA-regulated ATP sensitivity of Kir1.1 potassium channels in mouse kidney. J Clin Invest. 2006 Mar;116(3):797-807. Epub 2006 Feb 9. [PubMed:16470247 ]
Serrano-Martin X, Payares G, Mendoza-Leon A: Glibenclamide, a blocker of K+(ATP) channels, shows antileishmanial activity in experimental murine cutaneous leishmaniasis. Antimicrob Agents Chemother. 2006 Dec;50(12):4214-6. Epub 2006 Oct 2. [PubMed:17015627 ]

Enzyme Details

2. ATP-binding cassette sub-family C member 8

General function:: Involved in ATP binding
Specific function:: Putative subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release
Gene Name:: ABCC8
Uniprot ID:: Q09428
Molecular weight:: 177006.4

References

Dabrowski M, Ashcroft FM, Ashfield R, Lebrun P, Pirotte B, Egebjerg J, Bondo Hansen J, Wahl P: The novel diazoxide analog 3-isopropylamino-7-methoxy-4H-1,2,4-benzothiadiazine 1,1-dioxide is a selective Kir6.2/SUR1 channel opener. Diabetes. 2002 Jun;51(6):1896-906. [PubMed:12031979 ]
Hambrock A, Preisig-Muller R, Russ U, Piehl A, Hanley PJ, Ray J, Daut J, Quast U, Derst C: Four novel splice variants of sulfonylurea receptor 1. Am J Physiol Cell Physiol. 2002 Aug;283(2):C587-98. [PubMed:12107069 ]
Hambrock A, Loffler-Walz C, Quast U: Glibenclamide binding to sulphonylurea receptor subtypes: dependence on adenine nucleotides. Br J Pharmacol. 2002 Aug;136(7):995-1004. [PubMed:12145099 ]
Nielsen FE, Bodvarsdottir TB, Worsaae A, MacKay P, Stidsen CE, Boonen HC, Pridal L, Arkhammar PO, Wahl P, Ynddal L, Junager F, Dragsted N, Tagmose TM, Mogensen JP, Koch A, Treppendahl SP, Hansen JB: 6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives potently and selectively activate ATP sensitive potassium channels of pancreatic beta-cells. J Med Chem. 2002 Sep 12;45(19):4171-87. [PubMed:12213059 ]
Babenko AP, Bryan J: SUR-dependent modulation of KATP channels by an N-terminal KIR6.2 peptide. Defining intersubunit gating interactions. J Biol Chem. 2002 Nov 15;277(46):43997-4004. Epub 2002 Sep 3. [PubMed:12213829 ]
Ueda K, Komine J, Matsuo M, Seino S, Amachi T: Cooperative binding of ATP and MgADP in the sulfonylurea receptor is modulated by glibenclamide. Proc Natl Acad Sci U S A. 1999 Feb 16;96(4):1268-72. [PubMed:9990013 ]

Showing metabocard for Glycodiazine (HMDB0015461)

MOL for HMDB0015461 (Glycodiazine)

3D MOL for HMDB0015461 (Glycodiazine)

3D SDF for HMDB0015461 (Glycodiazine)

3D-SDF for HMDB0015461 (Glycodiazine)

PDB for HMDB0015461 (Glycodiazine)

3D PDB for HMDB0015461 (Glycodiazine)

SMILES for HMDB0015461 (Glycodiazine)

INCHI for HMDB0015461 (Glycodiazine)

Structure for HMDB0015461 (Glycodiazine)

3D Structure for HMDB0015461 (Glycodiazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References