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Showing metabocard for Isosorbide Dinitrate (HMDB0015021)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:50 UTC
HMDB IDHMDB0015021
Secondary Accession Numbers
  • HMDB15021
Metabolite Identification
Common NameIsosorbide Dinitrate
DescriptionIsosorbide Dinitrate is only found in individuals that have used or taken this drug. It is a vasodilator used in the treatment of angina pectoris. Its actions are similar to nitroglycerin but with a slower onset of action. [PubChem]Similar to other nitrites and organic nitrates, isosorbide dinitrate is converted to nitric oxide (NO), an active intermediate compound which activates the enzyme guanylate cyclase (atrial natriuretic peptide receptor A). This stimulates the synthesis of cyclic guanosine 3',5'-monophosphate (cGMP) which then activates a series of protein kinase-dependent phosphorylations in the smooth muscle cells, eventually resulting in the dephosphorylation of the myosin light chain of the smooth muscle fiber. The subsequent release of calcium ions results in the relaxation of the smooth muscle cells and vasodilation.
Structure
Data?1582753248
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015021 (Isosorbide Dinitrate)

883
  Mrv0541 02231215042D          

 18 19  0  0  1  0            999 V2000
    4.8295   -0.6610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    1.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092   -1.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494    2.4054    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.4441    1.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9472   -2.4054    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.6501   -1.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8930    1.6212    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2021   -1.6208    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0488    0.4154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0488   -0.4096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8295    0.6669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2641   -0.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3109    0.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7791    0.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.0754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -1.0697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 15  1  0  0  0  0
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3  9  1  0  0  0  0
 13  3  1  1  0  0  0
  4 10  1  0  0  0  0
 14  4  1  6  0  0  0
  5  9  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 17  1  1  0  0  0
 12 14  1  0  0  0  0
 12 18  1  1  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  CHG  4   5  -1   7  -1   9   1  10   1
M  END
Download

3D MOL for HMDB0015021 (Isosorbide Dinitrate)

HMDB0015021
     RDKit          3D
Isosorbide Dinitrate
 24 25  0  0  0  0  0  0  0  0999 V2000
   -4.4840   -0.7835    1.2410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090   -0.3618    0.1795 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7668   -0.3686   -0.9547 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.7283    0.1049    0.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -0.4761   -0.5871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9971    0.5387   -1.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.6813   -1.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3705    0.2669    0.2833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5639   -0.9276    0.3170 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1242   -2.0118   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -1.7099   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -0.4472    0.5656 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7911    0.2933    0.1044 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8102    0.5964    0.9891 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.0007    0.5688    0.6192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569    0.9381    2.3025 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0570   -1.3455   -1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0617    0.1567   -2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4842    1.5269   -1.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1423    1.0187    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -1.1215    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256   -2.5393    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607   -1.4196   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7392   -0.7342    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  9  5  1  0
 12  8  1  0
  5 17  1  6
  6 18  1  0
  6 19  1  0
  8 20  1  1
  9 21  1  1
 11 22  1  0
 11 23  1  0
 12 24  1  1
M  CHG  4   2   1   3  -1  14   1  16  -1
M  END
Download

3D SDF for HMDB0015021 (Isosorbide Dinitrate)

883
  Mrv0541 02231215042D          

 18 19  0  0  1  0            999 V2000
    4.8295   -0.6610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    1.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092   -1.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1494    2.4054    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.4441    1.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9472   -2.4054    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.6501   -1.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8930    1.6212    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2021   -1.6208    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.0488    0.4154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0488   -0.4096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8295    0.6669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2641   -0.6646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3109    0.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7791    0.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.0754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496   -1.0697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 15  1  0  0  0  0
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3  9  1  0  0  0  0
 13  3  1  1  0  0  0
  4 10  1  0  0  0  0
 14  4  1  6  0  0  0
  5  9  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 17  1  1  0  0  0
 12 14  1  0  0  0  0
 12 18  1  1  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  CHG  4   5  -1   7  -1   9   1  10   1
M  END
> <DATABASE_ID>
HMDB0015021

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1

> <INCHI_KEY>
MOYKHGMNXAOIAT-JGWLITMVSA-N

> <FORMULA>
C6H8N2O8

> <MOLECULAR_WEIGHT>
236.1363

> <EXACT_MASS>
236.028065242

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
18.072878323946657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aS,6R,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.44329140599999994

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8961390622848167

> <JCHEM_POLAR_SURFACE_AREA>
128.56

> <JCHEM_REFRACTIVITY>
44.77140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,6R,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0015021 (Isosorbide Dinitrate)

HMDB0015021
     RDKit          3D
Isosorbide Dinitrate
 24 25  0  0  0  0  0  0  0  0999 V2000
   -4.4840   -0.7835    1.2410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0090   -0.3618    0.1795 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7668   -0.3686   -0.9547 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.7283    0.1049    0.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -0.4761   -0.5871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9971    0.5387   -1.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    0.6813   -1.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3705    0.2669    0.2833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5639   -0.9276    0.3170 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1242   -2.0118   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568   -1.7099   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -0.4472    0.5656 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7911    0.2933    0.1044 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8102    0.5964    0.9891 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.0007    0.5688    0.6192 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569    0.9381    2.3025 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0570   -1.3455   -1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0617    0.1567   -2.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4842    1.5269   -1.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1423    1.0187    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -1.1215    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256   -2.5393    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607   -1.4196   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7392   -0.7342    1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  9  5  1  0
 12  8  1  0
  5 17  1  6
  6 18  1  0
  6 19  1  0
  8 20  1  1
  9 21  1  1
 11 22  1  0
 11 23  1  0
 12 24  1  1
M  CHG  4   2   1   3  -1  14   1  16  -1
M  END
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PDB for HMDB0015021 (Isosorbide Dinitrate)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 883                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.015  -1.234   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.093   1.251   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.493   2.709   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.617  -2.705   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.479   4.490   0.000  0.00  0.00           O-1
HETATM    6  O   UNK     0      12.029   1.880   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.635  -4.490   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0       3.080  -1.881   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      11.000   3.026   0.000  0.00  0.00           N+1
HETATM   10  N   UNK     0       4.111  -3.025   0.000  0.00  0.00           N+1
HETATM   11  C   UNK     0       7.558   0.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.558  -0.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.015   1.245   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.093  -1.241   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.914   0.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.188   0.005   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       7.559   2.007   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       7.559  -1.997   0.000  0.00  0.00           H+0
CONECT    1   12   15                                                       
CONECT    2   11   16                                                       
CONECT    3    9   13                                                       
CONECT    4   10   14                                                       
CONECT    5    9                                                            
CONECT    6    9                                                            
CONECT    7   10                                                            
CONECT    8   10                                                            
CONECT    9    3    5    6                                                  
CONECT   10    4    7    8                                                  
CONECT   11    2   12   13   17                                             
CONECT   12    1   11   14   18                                             
CONECT   13    3   11   15                                                  
CONECT   14    4   12   16                                                  
CONECT   15    1   13                                                       
CONECT   16    2   14                                                       
CONECT   17   11                                                            
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END
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3D PDB for HMDB0015021 (Isosorbide Dinitrate)

COMPND    HMDB0015021
HETATM    1  O1  UNL     1      -4.484  -0.784   1.241  1.00  0.00           O  
HETATM    2  N1  UNL     1      -4.009  -0.362   0.180  1.00  0.00           N1+
HETATM    3  O2  UNL     1      -4.767  -0.369  -0.955  1.00  0.00           O1-
HETATM    4  O3  UNL     1      -2.728   0.105   0.164  1.00  0.00           O  
HETATM    5  C1  UNL     1      -1.684  -0.476  -0.587  1.00  0.00           C  
HETATM    6  C2  UNL     1      -0.997   0.539  -1.463  1.00  0.00           C  
HETATM    7  O4  UNL     1       0.292   0.681  -1.020  1.00  0.00           O  
HETATM    8  C3  UNL     1       0.371   0.267   0.283  1.00  0.00           C  
HETATM    9  C4  UNL     1      -0.564  -0.928   0.317  1.00  0.00           C  
HETATM   10  O5  UNL     1       0.124  -2.012  -0.152  1.00  0.00           O  
HETATM   11  C5  UNL     1       1.457  -1.710  -0.244  1.00  0.00           C  
HETATM   12  C6  UNL     1       1.699  -0.447   0.566  1.00  0.00           C  
HETATM   13  O6  UNL     1       2.791   0.293   0.104  1.00  0.00           O  
HETATM   14  N2  UNL     1       3.810   0.596   0.989  1.00  0.00           N1+
HETATM   15  O7  UNL     1       5.001   0.569   0.619  1.00  0.00           O  
HETATM   16  O8  UNL     1       3.557   0.938   2.303  1.00  0.00           O1-
HETATM   17  H1  UNL     1      -2.057  -1.346  -1.145  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.062   0.157  -2.509  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.484   1.527  -1.462  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.142   1.019   1.036  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.933  -1.122   1.364  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.126  -2.539   0.073  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.661  -1.420  -1.315  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.739  -0.734   1.614  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5
CONECT    5    6    9   17
CONECT    6    7   18   19
CONECT    7    8
CONECT    8    9   12   20
CONECT    9   10   21
CONECT   10   11
CONECT   11   12   22   23
CONECT   12   13   24
CONECT   13   14
CONECT   14   15   15   16
END
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SMILES for HMDB0015021 (Isosorbide Dinitrate)

[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O
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INCHI for HMDB0015021 (Isosorbide Dinitrate)

InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,4:3,6-Dianhydrosorbitol 2,5-dinitrateChEBI
CarvasinChEBI
Cedocard retardChEBI
D-Isosorbide dinitrateChEBI
Dianhydrosorbitol 2,5-dinitrateChEBI
Dinitrate d'isosorbideChEBI
Dinitrato de isosorbidaChEBI
DinitroisosorbideChEBI
DinitrosorbideChEBI
FlindixChEBI
IsoketChEBI
IsorbidChEBI
IsordilChEBI
Isosorbide 2,5-dinitrateChEBI
Isosorbidi dinitrasChEBI
NitrosorbideChEBI
Sorbide nitrateChEBI
SorbidilatChEBI
SorbidnitrateChEBI
Dilatrate-SRKegg
1,4:3,6-Dianhydrosorbitol 2,5-dinitric acidGenerator
D-Isosorbide dinitric acidGenerator
Dianhydrosorbitol 2,5-dinitric acidGenerator
Dinitric acid d'isosorbideGenerator
Isosorbide 2,5-dinitric acidGenerator
Sorbide nitric acidGenerator
Sorbidnitric acidGenerator
Dilatric acid-SRGenerator
Isosorbide dinitric acidGenerator
Sorbide, dinitrateHMDB
DilatrateHMDB
Iso-bidHMDB
Isoket retard 120HMDB
Isoket retard-120HMDB
IsotrateHMDB
Cardonit 40HMDB
Iso bidHMDB
SorbitrateHMDB
Dinitrate, isosorbideHMDB
Isoket retard120HMDB
Isomak RHMDB
SorbonitHMDB
IsoBidHMDB
IsodinitHMDB
Chemical FormulaC6H8N2O8
Average Molecular Weight236.1363
Monoisotopic Molecular Weight236.028065242
IUPAC Name(3S,3aS,6R,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate
Traditional Name(3S,3aS,6R,6aS)-6-(nitrooxy)-hexahydrofuro[3,2-b]furan-3-yl nitrate
CAS Registry Number87-33-2
SMILES
[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O
InChI Identifier
InChI=1S/C6H8N2O8/c9-7(10)15-3-1-13-6-4(16-8(11)12)2-14-5(3)6/h3-6H,1-2H2/t3-,4+,5-,6-/m1/s1
InChI KeyMOYKHGMNXAOIAT-JGWLITMVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassIsosorbides
Direct ParentIsosorbides
Alternative Parents
Substituents
  • Isosorbide
  • Organic nitrate
  • Tetrahydrofuran
  • Alkyl nitrate
  • Organic nitric acid or derivatives
  • Organic nitro compound
  • Dialkyl ether
  • Ether
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point70 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.94 g/LNot Available
LogP1.31HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available151.588http://allccs.zhulab.cn/database/detail?ID=AllCCS00000999
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.94 g/LALOGPS
logP0.87ALOGPS
logP0.44ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area128.56 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity44.77 m³·mol⁻¹ChemAxon
Polarizability18.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.06831661259
DarkChem[M-H]-152.03931661259
DeepCCS[M-2H]-164.73230932474
DeepCCS[M+Na]+139.60330932474
AllCCS[M+H]+149.532859911
AllCCS[M+H-H2O]+145.832859911
AllCCS[M+NH4]+153.032859911
AllCCS[M+Na]+154.032859911
AllCCS[M-H]-146.632859911
AllCCS[M+Na-2H]-146.632859911
AllCCS[M+HCOO]-146.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isosorbide Dinitrate[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O2801.4Standard polar33892256
Isosorbide Dinitrate[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O1624.9Standard non polar33892256
Isosorbide Dinitrate[H][C@]12OC[C@H](O[N+]([O-])=O)[C@@]1([H])OC[C@H]2O[N+]([O-])=O1708.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isosorbide Dinitrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9410000000-92c2931ba576380c836c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isosorbide Dinitrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isosorbide Dinitrate 10V, Positive-QTOFsplash10-000i-0190000000-4ac5c9f364014be4b5ed2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isosorbide Dinitrate 20V, Positive-QTOFsplash10-05fr-0490000000-296d2bcb699d8eeed9cc2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isosorbide Dinitrate 40V, Positive-QTOFsplash10-03di-2900000000-1c95dd82e8ca93a68ef42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isosorbide Dinitrate 10V, Negative-QTOFsplash10-000l-2890000000-b3fc1aa7995241f9c8c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isosorbide Dinitrate 20V, Negative-QTOFsplash10-0076-1960000000-482b81af13a797c89c892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isosorbide Dinitrate 40V, Negative-QTOFsplash10-0006-4900000000-3c42a9008364f7f3fe6b2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00883 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00883 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00883
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6619
KEGG Compound IDC07456
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsosorbide dinitrate
METLIN IDNot Available
PubChem Compound6883
PDB IDNot Available
ChEBI ID6061
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. 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. Atrial natriuretic peptide receptor 1
General function:
Involved in phosphorus-oxygen lyase activity
Specific function:
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate cyclase activity upon binding of the ligand.
Gene Name:
NPR1
Uniprot ID:
P16066
Molecular weight:
118918.11
References
  1. 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 ]
  2. 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 ]
  3. Villarroya M, Lopez MG, de Pascual R, Garcia AG: Preclinical profile of PF9404C, a nitric oxide donor with beta receptor blocking properties. Cardiovasc Drug Rev. 2005 Summer;23(2):149-60. [PubMed:16007231 ]
  4. Takabuchi S, Hirota K, Nishi K, Oda S, Oda T, Shingu K, Takabayashi A, Adachi T, Semenza GL, Fukuda K: The inhibitory effect of sodium nitroprusside on HIF-1 activation is not dependent on nitric oxide-soluble guanylyl cyclase pathway. Biochem Biophys Res Commun. 2004 Nov 5;324(1):417-23. [PubMed:15465035 ]
  5. Beauregard C, Brandt PC, Chiou GC: Nitric oxide and cyclic GMP-mediated protein secretion from cultured lacrimal gland acinar cells. J Ocul Pharmacol Ther. 2002 Oct;18(5):429-43. [PubMed:12419094 ]
Enzyme Details
3. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. 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 ]