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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014356

Secondary Accession Numbers

HMDB14356

Metabolite Identification

Common Name

Midodrine

Description

Midodrine is only found in individuals that have used or taken this drug. It is an ethanolamine derivative that is an adrenergic alpha agonist. It is used as a vasoconstrictor agent in the treatment of hypotension. [PubChem]Midodrine forms an active metabolite, desglymidodrine, that is an alpha₁-agonist, and exerts its actions via activation of the alpha-adrenergic receptors of the arteriolar and venous vasculature, producing an increase in vascular tone and elevation of blood pressure. Desglymidodrine does not stimulate cardiac beta-adrenergic receptors.

Structure

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

HMDB0014356
     RDKit          3D
Midodrine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.4415   -3.3164    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -2.1657    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.9043    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6349    0.1099    1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338    1.3797    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    1.6527    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223    2.9088    0.2059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224    4.0592    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117    0.6380   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1531    0.9349   -1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    1.6381   -2.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -0.3186   -2.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -1.1002   -1.1415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -0.5431   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122    0.6422   -0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -1.3319    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -0.5911    1.1019 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -0.6201   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -3.3749   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -3.4496    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7780   -4.1939    0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -0.0701    2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    2.1781    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368    4.9922    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0448    4.0289    1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771    4.1534    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561    1.5691   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    1.0125   -3.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343   -0.8968   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -0.0311   -2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -2.0789   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7787   -2.2545    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.6301    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3145   -0.7685    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6146   -0.8225    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0043   -1.4353   -0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  9 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END

211
  Mrv0541 02231214312D          

 18 18  0  0  1  0            999 V2000
    3.0791    0.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.8381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 10  1  0  0  0  0
  2 17  1  0  0  0  0
  3 12  1  0  0  0  0
  3 18  1  0  0  0  0
  4 15  2  0  0  0  0
  5  9  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  2  0  0  0  0
 12 14  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014356

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)

> <INCHI_KEY>
PTKSEFOSCHHMPD-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O4

> <MOLECULAR_WEIGHT>
254.2823

> <EXACT_MASS>
254.126657074

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.649608228886468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

> <ALOGPS_LOGP>
-0.49

> <JCHEM_LOGP>
-0.9519464609999999

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.25703281593573

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.765053491042249

> <JCHEM_PKA_STRONGEST_BASIC>
8.139313298334233

> <JCHEM_POLAR_SURFACE_AREA>
93.80999999999999

> <JCHEM_REFRACTIVITY>
66.22380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
midodrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014356
     RDKit          3D
Midodrine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.4415   -3.3164    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -2.1657    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.9043    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6349    0.1099    1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338    1.3797    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    1.6527    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223    2.9088    0.2059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224    4.0592    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117    0.6380   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1531    0.9349   -1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    1.6381   -2.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -0.3186   -2.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -1.1002   -1.1415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -0.5431   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122    0.6422   -0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -1.3319    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -0.5911    1.1019 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -0.6201   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -3.3749   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -3.4496    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7780   -4.1939    0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -0.0701    2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    2.1781    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368    4.9922    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0448    4.0289    1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771    4.1534    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561    1.5691   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    1.0125   -3.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343   -0.8968   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -0.0311   -2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -2.0789   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7787   -2.2545    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.6301    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3145   -0.7685    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6146   -0.8225    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0043   -1.4353   -0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  9 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 211                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   0.678   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414  -1.632   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748  -4.713   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   2.218   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.415   2.218   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      11.082   5.298   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081  -0.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -1.632   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -2.402   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -2.402   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -3.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -3.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -4.713   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748   2.988   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   4.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -2.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -6.253   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   10   17                                                       
CONECT    3   12   18                                                       
CONECT    4   15                                                            
CONECT    5    9   15                                                       
CONECT    6   16                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    5    7                                                       
CONECT   10    2    8   13                                                  
CONECT   11    8   12                                                       
CONECT   12    3   11   14                                                  
CONECT   13   10   14                                                       
CONECT   14   12   13                                                       
CONECT   15    4    5   16                                                  
CONECT   16    6   15                                                       
CONECT   17    2                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0014356
HETATM    1  C1  UNL     1      -2.442  -3.316   0.291  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.741  -2.166   1.030  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.220  -0.904   0.802  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.635   0.110   1.636  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.134   1.380   1.435  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.236   1.653   0.428  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.722   2.909   0.206  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.022   4.059   0.945  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.812   0.638  -0.418  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.153   0.935  -1.530  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.513   1.638  -2.548  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.748  -0.319  -2.122  1.00  0.00           C  
HETATM   13  N1  UNL     1       1.489  -1.100  -1.142  1.00  0.00           N  
HETATM   14  C10 UNL     1       2.614  -0.543  -0.461  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.012   0.642  -0.685  1.00  0.00           O  
HETATM   16  C11 UNL     1       3.358  -1.332   0.532  1.00  0.00           C  
HETATM   17  N2  UNL     1       4.456  -0.591   1.102  1.00  0.00           N  
HETATM   18  C12 UNL     1      -1.319  -0.620  -0.206  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.007  -3.375  -0.664  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.362  -3.450   0.078  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.778  -4.194   0.910  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.349  -0.070   2.451  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.476   2.178   2.111  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.937   4.992   0.347  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.045   4.029   1.341  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.277   4.153   1.786  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.956   1.569  -1.159  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.784   1.013  -3.267  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.034  -0.897  -2.611  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.479  -0.031  -2.916  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.236  -2.079  -0.907  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.779  -2.255   0.081  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.641  -1.630   1.346  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.315  -0.769   0.552  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.615  -0.823   2.099  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.004  -1.435  -0.870  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7    9
CONECT    7    8
CONECT    8   24   25   26
CONECT    9   10   18   18
CONECT   10   11   12   27
CONECT   11   28
CONECT   12   13   29   30
CONECT   13   14   31
CONECT   14   15   15   16
CONECT   16   17   32   33
CONECT   17   34   35
CONECT   18   36
END

HMDB0014356
     RDKit          3D
Midodrine
 36 36  0  0  0  0  0  0  0  0999 V2000
   -2.4415   -3.3164    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -2.1657    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.9043    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6349    0.1099    1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338    1.3797    1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    1.6527    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7223    2.9088    0.2059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0224    4.0592    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117    0.6380   -0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1531    0.9349   -1.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128    1.6381   -2.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -0.3186   -2.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -1.1002   -1.1415 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6142   -0.5431   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122    0.6422   -0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -1.3319    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558   -0.5911    1.1019 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3193   -0.6201   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -3.3749   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -3.4496    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7780   -4.1939    0.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -0.0701    2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4764    2.1781    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9368    4.9922    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0448    4.0289    1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771    4.1534    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561    1.5691   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843    1.0125   -3.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0343   -0.8968   -2.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -0.0311   -2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -2.0789   -0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7787   -2.2545    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.6301    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3145   -0.7685    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6146   -0.8225    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0043   -1.4353   -0.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  9 18  2  0
 18  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-2-Amino-N-(beta-hydroxy-2,5-dimethoxyphenethyl)acetamide	ChEBI
1-(2',5'-Dimethoxyphenyl)-2-glycinamidoethanol	ChEBI
2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamide	ChEBI
DL-N1-(beta-Hydroxy-2,5-dimethoxyphenethyl)glycinamid	ChEBI
Midodrina	ChEBI
Midodrinum	ChEBI
(+-)-2-Amino-N-(b-hydroxy-2,5-dimethoxyphenethyl)acetamide	Generator
(+-)-2-Amino-N-(β-hydroxy-2,5-dimethoxyphenethyl)acetamide	Generator
2-Amino-N-(2,5-dimethoxy-b-hydroxyphenethyl)acetamide	Generator
2-Amino-N-(2,5-dimethoxy-β-hydroxyphenethyl)acetamide	Generator
DL-N1-(b-Hydroxy-2,5-dimethoxyphenethyl)glycinamid	Generator
DL-N1-(Β-hydroxy-2,5-dimethoxyphenethyl)glycinamid	Generator
Midodrin	HMDB
Midodrine HCL	HMDB
Midodrine hydrochloride	HMDB
Amatine	HMDB
Cahill may roberts brand OF midodrine monohydrochloride	HMDB
Nycomed brand OF midodrine monohydrochloride	HMDB
Christiaens brand OF midodrine monohydrochloride	HMDB
Monohydrochloride, midodrine	HMDB
ProAmatine	HMDB
Shire brand OF midodrine monohydrochloride	HMDB
Midodrine monohydrochloride	HMDB
Gutron	HMDB
Midon	HMDB

Chemical Formula

C₁₂H₁₈N₂O₄

Average Molecular Weight

254.2823

Monoisotopic Molecular Weight

254.126657074

IUPAC Name

2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide

Traditional Name

midodrine

CAS Registry Number

133163-28-7

SMILES

COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1

InChI Identifier

InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)

InChI Key

PTKSEFOSCHHMPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

P-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Ether
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Organic nitrogen compound
Alcohol
Primary amine
Hydrocarbon derivative
Aromatic alcohol
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:6933 )
amino acid amide (CHEBI:6933 )
secondary alcohol (CHEBI:6933 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014356)

Source

Exogenous

Exogenous (HMDB: HMDB0014356)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.45 g/L	Not Available
LogP	-0.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.45 g/L	ALOGPS
logP	-0.49	ALOGPS
logP	-0.95	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	8.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	66.22 m³·mol⁻¹	ChemAxon
Polarizability	26.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	159.24	31661259
DarkChem	[M-H]-	159.671	31661259
DeepCCS	[M+H]+	160.098	30932474
DeepCCS	[M-H]-	157.74	30932474
DeepCCS	[M-2H]-	190.626	30932474
DeepCCS	[M+Na]+	166.191	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.7	32859911
AllCCS	[M+NH4]+	162.6	32859911
AllCCS	[M+Na]+	163.5	32859911
AllCCS	[M-H]-	159.8	32859911
AllCCS	[M+Na-2H]-	160.2	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.12 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7738 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.6 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	106.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	921.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	228.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	121.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	259.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	324.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	637.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	684.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	237.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	877.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	455.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	363.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	59.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Midodrine	COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1	3313.4	Standard polar	33892256
Midodrine	COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1	2217.6	Standard non polar	33892256
Midodrine	COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1	2373.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Midodrine,1TMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN)O[Si](C)(C)C)=C1	2320.3	Semi standard non polar	33892256
Midodrine,1TMS,isomer #2	COC1=CC=C(OC)C(C(O)CNC(=O)CN[Si](C)(C)C)=C1	2402.0	Semi standard non polar	33892256
Midodrine,1TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN)[Si](C)(C)C)=C1	2282.2	Semi standard non polar	33892256
Midodrine,2TMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN[Si](C)(C)C)O[Si](C)(C)C)=C1	2358.2	Semi standard non polar	33892256
Midodrine,2TMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN[Si](C)(C)C)O[Si](C)(C)C)=C1	2293.4	Standard non polar	33892256
Midodrine,2TMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN[Si](C)(C)C)O[Si](C)(C)C)=C1	3141.2	Standard polar	33892256
Midodrine,2TMS,isomer #2	COC1=CC=C(OC)C(C(CN(C(=O)CN)[Si](C)(C)C)O[Si](C)(C)C)=C1	2296.9	Semi standard non polar	33892256
Midodrine,2TMS,isomer #2	COC1=CC=C(OC)C(C(CN(C(=O)CN)[Si](C)(C)C)O[Si](C)(C)C)=C1	2291.7	Standard non polar	33892256
Midodrine,2TMS,isomer #2	COC1=CC=C(OC)C(C(CN(C(=O)CN)[Si](C)(C)C)O[Si](C)(C)C)=C1	3245.5	Standard polar	33892256
Midodrine,2TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN[Si](C)(C)C)[Si](C)(C)C)=C1	2359.6	Semi standard non polar	33892256
Midodrine,2TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN[Si](C)(C)C)[Si](C)(C)C)=C1	2508.4	Standard non polar	33892256
Midodrine,2TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN[Si](C)(C)C)[Si](C)(C)C)=C1	3194.9	Standard polar	33892256
Midodrine,2TMS,isomer #4	COC1=CC=C(OC)C(C(O)CNC(=O)CN([Si](C)(C)C)[Si](C)(C)C)=C1	2502.2	Semi standard non polar	33892256
Midodrine,2TMS,isomer #4	COC1=CC=C(OC)C(C(O)CNC(=O)CN([Si](C)(C)C)[Si](C)(C)C)=C1	2548.9	Standard non polar	33892256
Midodrine,2TMS,isomer #4	COC1=CC=C(OC)C(C(O)CNC(=O)CN([Si](C)(C)C)[Si](C)(C)C)=C1	3265.9	Standard polar	33892256
Midodrine,3TMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2320.3	Semi standard non polar	33892256
Midodrine,3TMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2426.6	Standard non polar	33892256
Midodrine,3TMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2906.9	Standard polar	33892256
Midodrine,3TMS,isomer #2	COC1=CC=C(OC)C(C(CNC(=O)CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2440.7	Semi standard non polar	33892256
Midodrine,3TMS,isomer #2	COC1=CC=C(OC)C(C(CNC(=O)CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2475.0	Standard non polar	33892256
Midodrine,3TMS,isomer #2	COC1=CC=C(OC)C(C(CNC(=O)CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2944.6	Standard polar	33892256
Midodrine,3TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2458.4	Semi standard non polar	33892256
Midodrine,3TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2664.0	Standard non polar	33892256
Midodrine,3TMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3019.2	Standard polar	33892256
Midodrine,4TMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2484.3	Semi standard non polar	33892256
Midodrine,4TMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2578.8	Standard non polar	33892256
Midodrine,4TMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	2774.8	Standard polar	33892256
Midodrine,1TBDMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN)O[Si](C)(C)C(C)(C)C)=C1	2597.1	Semi standard non polar	33892256
Midodrine,1TBDMS,isomer #2	COC1=CC=C(OC)C(C(O)CNC(=O)CN[Si](C)(C)C(C)(C)C)=C1	2656.6	Semi standard non polar	33892256
Midodrine,1TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN)[Si](C)(C)C(C)(C)C)=C1	2554.5	Semi standard non polar	33892256
Midodrine,2TBDMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2831.9	Semi standard non polar	33892256
Midodrine,2TBDMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2747.1	Standard non polar	33892256
Midodrine,2TBDMS,isomer #1	COC1=CC=C(OC)C(C(CNC(=O)CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3235.1	Standard polar	33892256
Midodrine,2TBDMS,isomer #2	COC1=CC=C(OC)C(C(CN(C(=O)CN)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2804.5	Semi standard non polar	33892256
Midodrine,2TBDMS,isomer #2	COC1=CC=C(OC)C(C(CN(C(=O)CN)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2701.0	Standard non polar	33892256
Midodrine,2TBDMS,isomer #2	COC1=CC=C(OC)C(C(CN(C(=O)CN)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3303.9	Standard polar	33892256
Midodrine,2TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2865.7	Semi standard non polar	33892256
Midodrine,2TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2878.1	Standard non polar	33892256
Midodrine,2TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3269.9	Standard polar	33892256
Midodrine,2TBDMS,isomer #4	COC1=CC=C(OC)C(C(O)CNC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2965.7	Semi standard non polar	33892256
Midodrine,2TBDMS,isomer #4	COC1=CC=C(OC)C(C(O)CNC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2869.5	Standard non polar	33892256
Midodrine,2TBDMS,isomer #4	COC1=CC=C(OC)C(C(O)CNC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3297.7	Standard polar	33892256
Midodrine,3TBDMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3046.7	Semi standard non polar	33892256
Midodrine,3TBDMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3014.8	Standard non polar	33892256
Midodrine,3TBDMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3156.8	Standard polar	33892256
Midodrine,3TBDMS,isomer #2	COC1=CC=C(OC)C(C(CNC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3153.5	Semi standard non polar	33892256
Midodrine,3TBDMS,isomer #2	COC1=CC=C(OC)C(C(CNC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3013.1	Standard non polar	33892256
Midodrine,3TBDMS,isomer #2	COC1=CC=C(OC)C(C(CNC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3158.0	Standard polar	33892256
Midodrine,3TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3162.1	Semi standard non polar	33892256
Midodrine,3TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3123.8	Standard non polar	33892256
Midodrine,3TBDMS,isomer #3	COC1=CC=C(OC)C(C(O)CN(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3213.4	Standard polar	33892256
Midodrine,4TBDMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3379.0	Semi standard non polar	33892256
Midodrine,4TBDMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3259.1	Standard non polar	33892256
Midodrine,4TBDMS,isomer #1	COC1=CC=C(OC)C(C(CN(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	3114.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Midodrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-9420000000-7d9c097f5836b8a5fae7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Midodrine GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-2901000000-dca22bfb649bee6445c3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Midodrine 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 - Midodrine 10V, Positive-QTOF	splash10-0a59-5590000000-c1d7a0986ff760045ce1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 20V, Positive-QTOF	splash10-000t-3900000000-e616153c52e6dab85f03	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 40V, Positive-QTOF	splash10-05o0-6900000000-90bdd17739520c368242	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 10V, Negative-QTOF	splash10-0udi-2290000000-2b1a688c778f1a3b4f73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 20V, Negative-QTOF	splash10-0fki-9780000000-3ec6e31d870a13fc1277	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 40V, Negative-QTOF	splash10-0596-9510000000-f2530e4ed2f894325b44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 10V, Positive-QTOF	splash10-0a4i-0290000000-be85220bae16e2ca879f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 20V, Positive-QTOF	splash10-001i-1910000000-846cb5ab8c2f374a839a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 40V, Positive-QTOF	splash10-0540-9600000000-457f0b777313d983dbcd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 10V, Negative-QTOF	splash10-0udi-3290000000-bba27a0b4e7c20b0735e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 20V, Negative-QTOF	splash10-00di-9600000000-75c1caa8420dbc10acec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Midodrine 40V, Negative-QTOF	splash10-0pi3-5920000000-8736da98df9e10c5809c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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 DB00211	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00211	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00211

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4050

KEGG Compound ID

C07890

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Midodrine

METLIN ID

Not Available

PubChem Compound

4195

PDB ID

Not Available

ChEBI ID

6933

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

Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)]. Wien Med Wochenschr. 1981 Feb 28;131(4):109-12. [PubMed:6165144 ]
Tsuda M, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K: Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60. Epub 2006 Apr 5. [PubMed:16597710 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Buckner SA, Milicic I, Daza AV, Meyer MD, Altenbach RJ, Williams M, Sullivan JP, Brioni JD: ABT-866, a novel alpha(1A)-adrenoceptor agonist with antagonist properties at the alpha(1B)- and alpha(1D)-adrenoceptor subtypes. Eur J Pharmacol. 2002 Aug 2;449(1-2):159-65. [PubMed:12163120 ]
Taniguchi N, Hamada K, Ogasawara T, Ukai Y, Yoshikuni Y, Kimura K: NS-49, an alpha 1A-adrenoceptor agonist, selectively increases intraurethral pressure in dogs. Eur J Pharmacol. 1996 Dec 27;318(1):117-22. [PubMed:9007522 ]
Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O'Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP: Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist. J Med Chem. 2004 Jun 3;47(12):3220-35. [PubMed:15163201 ]

Enzyme Details

3. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O'Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP: Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist. J Med Chem. 2004 Jun 3;47(12):3220-35. [PubMed:15163201 ]

Showing metabocard for Midodrine (HMDB0014356)

MOL for HMDB0014356 (Midodrine)

3D MOL for HMDB0014356 (Midodrine)

3D SDF for HMDB0014356 (Midodrine)

3D-SDF for HMDB0014356 (Midodrine)

PDB for HMDB0014356 (Midodrine)

3D PDB for HMDB0014356 (Midodrine)

SMILES for HMDB0014356 (Midodrine)

INCHI for HMDB0014356 (Midodrine)

Structure for HMDB0014356 (Midodrine)

3D Structure for HMDB0014356 (Midodrine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References