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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:45:30 UTC

Update Date

2022-09-22 17:45:00 UTC

HMDB ID

HMDB0245703

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate

Description

Molsidomine, also known as molsidomin stada or corvaton, belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. Molsidomine is a prodrug that is hydrolysed to linsidomine (SIN-1) in the liver via first-pass effect, which subsequently releases NO. 44–59% of molsidomine reach the bloodstream in unchanged form, 3–11% of which are bound to plasma proteins. Molsidomine is an extremely weak basic (essentially neutral) compound (based on its pKa). Ergolines can antagonise the effects of molsidomine. It is also used to treat angina in the context of an acute myocardial infarction. The substance is sensitive to ultraviolet light at wavelengths shorter than 320 nm. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-ethoxy-n-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245703
     RDKit          3D
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.6111    0.3965   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4969   -1.0385   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -1.3847   -0.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -1.3148    0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -0.9307    1.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9546   -1.6678    0.5846 N   0  0  0  0  0  2  0  0  0  0  0  0
    0.8973   -0.7579    0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -0.7974    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0654    0.2471    0.4206 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3505    0.5750   -0.0130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804   -0.2785   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -0.4535   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0757    0.7620   -0.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    1.3676    0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0792    1.7212    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    0.9062    1.3029 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364    0.3042    1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492    0.7569    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147    0.5652    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8267    1.0119   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -1.7250    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9323   -1.1491   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -1.5727   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.3014   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895    0.1760   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -1.0836    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144   -1.0186   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5657    0.7194    1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158    2.2794    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0770    2.5700   -0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829    2.1155    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  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  1  0
  9 16  2  0
 16 17  1  0
 17  7  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  CHG  2   6  -1   9   1
M  END


  Mrv1572010291512042D          

 17 18  0  0  0  0            999 V2000
    1.9109   -0.2767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -0.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9029   -1.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282   -1.7104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -0.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024    0.4398    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.7592    1.2238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0900    1.7104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    0.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2928    1.6395    0.0000 N   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0052    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175    1.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    0.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1446    1.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  7  1  0  0  0  0
  5  6  1  0  0  0  0
 10 12  1  0  0  0  0
  6  1  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1  7  1  0  0  0  0
 14 15  1  0  0  0  0
  1  2  1  0  0  0  0
 13 16  2  0  0  0  0
  2  3  1  0  0  0  0
 15 17  1  0  0  0  0
M  CHG  2   7   1  12  -1
M  END
> <DATABASE_ID>
HMDB0245703

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3

> <INCHI_KEY>
XLFWDASMENKTKL-UHFFFAOYSA-N

> <FORMULA>
C9H14N4O4

> <MOLECULAR_WEIGHT>
242.235

> <EXACT_MASS>
242.101504947

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.73803531577071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ⁵-oxadiazol-3-ylium

> <ALOGPS_LOGP>
-1.04

> <JCHEM_LOGP>
-1.0168913401384128

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.158387817685217

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.991301077599376

> <JCHEM_PKA_STRONGEST_BASIC>
-3.155905039477173

> <JCHEM_POLAR_SURFACE_AREA>
77.91

> <JCHEM_REFRACTIVITY>
76.99079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ⁵-oxadiazol-3-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245703
     RDKit          3D
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.6111    0.3965   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4969   -1.0385   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -1.3847   -0.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -1.3148    0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -0.9307    1.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9546   -1.6678    0.5846 N   0  0  0  0  0  2  0  0  0  0  0  0
    0.8973   -0.7579    0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -0.7974    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0654    0.2471    0.4206 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3505    0.5750   -0.0130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804   -0.2785   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -0.4535   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0757    0.7620   -0.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    1.3676    0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0792    1.7212    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    0.9062    1.3029 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364    0.3042    1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492    0.7569    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147    0.5652    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8267    1.0119   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -1.7250    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9323   -1.1491   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -1.5727   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.3014   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895    0.1760   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -1.0836    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144   -1.0186   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5657    0.7194    1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158    2.2794    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0770    2.5700   -0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829    2.1155    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  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  1  0
  9 16  2  0
 16 17  1  0
 17  7  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  CHG  2   6  -1   9   1
M  END

HEADER    PROTEIN                                 29-OCT-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-OCT-15         0                                  
HETATM    1  N   UNK     0       3.567  -0.516   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.789  -1.846   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.552  -3.184   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.093  -3.193   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.870  -1.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.107  -0.525   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.804   0.821   0.000  0.00  0.00           N+1
HETATM    8  N   UNK     0       3.284   2.284   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       2.035   3.193   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.786   2.284   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.265   0.821   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.547   3.060   0.000  0.00  0.00           N-1
HETATM   13  C   UNK     0      -1.876   2.291   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.206   3.060   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.536   2.291   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.876   0.751   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.870   3.059   0.000  0.00  0.00           C+0
CONECT    1    6    7    2                                                  
CONECT    2    1    3                                                       
CONECT    3    4    2                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    8   11    1                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    7                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   17                                                       
CONECT   16   13                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0245703
HETATM    1  C1  UNL     1       5.611   0.397  -0.080  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.497  -1.039  -0.495  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.115  -1.385  -0.503  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.330  -1.315   0.636  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.885  -0.931   1.697  1.00  0.00           O  
HETATM    6  N1  UNL     1       1.955  -1.668   0.585  1.00  0.00           N1-
HETATM    7  C4  UNL     1       0.897  -0.758   0.706  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.307  -0.797   0.041  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.065   0.247   0.421  1.00  0.00           N1+
HETATM   10  N3  UNL     1      -2.351   0.575  -0.013  1.00  0.00           N  
HETATM   11  C6  UNL     1      -2.980  -0.278  -0.983  1.00  0.00           C  
HETATM   12  C7  UNL     1      -4.447  -0.454  -0.592  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.076   0.762  -0.421  1.00  0.00           O  
HETATM   14  C8  UNL     1      -4.533   1.368   0.715  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.079   1.721   0.458  1.00  0.00           C  
HETATM   16  N4  UNL     1      -0.326   0.906   1.303  1.00  0.00           N  
HETATM   17  O4  UNL     1       0.836   0.304   1.467  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.649   0.757   0.290  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.415   0.565   0.670  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.827   1.012  -0.995  1.00  0.00           H  
HETATM   21  H4  UNL     1       6.062  -1.725   0.179  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.932  -1.149  -1.507  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.559  -1.573  -0.671  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.554  -1.301  -1.018  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.890   0.176  -1.980  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.487  -1.084   0.319  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.914  -1.019  -1.420  1.00  0.00           H  
HETATM   28  H11 UNL     1      -4.566   0.719   1.603  1.00  0.00           H  
HETATM   29  H12 UNL     1      -5.116   2.279   0.909  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.077   2.570  -0.242  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.683   2.116   1.426  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    8   17
CONECT    8    9   23
CONECT    9   10   16   16
CONECT   10   11   15
CONECT   11   12   24   25
CONECT   12   13   26   27
CONECT   13   14
CONECT   14   15   28   29
CONECT   15   30   31
CONECT   16   17
END

HMDB0245703
     RDKit          3D
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.6111    0.3965   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4969   -1.0385   -0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -1.3847   -0.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -1.3148    0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -0.9307    1.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9546   -1.6678    0.5846 N   0  0  0  0  0  2  0  0  0  0  0  0
    0.8973   -0.7579    0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3071   -0.7974    0.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0654    0.2471    0.4206 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.3505    0.5750   -0.0130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9804   -0.2785   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -0.4535   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0757    0.7620   -0.4205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    1.3676    0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0792    1.7212    0.4583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263    0.9062    1.3029 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364    0.3042    1.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6492    0.7569    0.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147    0.5652    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8267    1.0119   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -1.7250    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9323   -1.1491   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -1.5727   -0.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.3014   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895    0.1760   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -1.0836    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144   -1.0186   -1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5657    0.7194    1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1158    2.2794    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0770    2.5700   -0.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829    2.1155    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  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  1  0
  9 16  2  0
 16 17  1  0
 17  7  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
M  CHG  2   6  -1   9   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Corvaton	MeSH
Molsidain	MeSH
Morsydomine	MeSH
SIN 10	MeSH
Molsidomin stada	MeSH
Von CT, molsidomin	MeSH
Molsi 1a pharma	MeSH
Molsibeta	MeSH
SIN10	MeSH
Molsi-azu	MeSH
Molsicor	MeSH
Fali cor	MeSH
Molsihexal	MeSH
Molsi azu	MeSH
Molsidomin	MeSH
Molsidomin ratiopharm	MeSH
Fali-cor	MeSH
SIN-10	MeSH
Korvatone	MeSH
Molsidomin heumann	MeSH
Molsidomin-ratiopharm	MeSH
Molsi puren	MeSH
Sydnopharm	MeSH
Duracoron	MeSH
MTW-Molsidomin	MeSH
Heumann, molsidomin	MeSH
Molsiket	MeSH
MTW Molsidomin	MeSH
Molsidomin von CT	MeSH
Corpea	MeSH
Molsi-puren	MeSH
Alpharma brand OF molsidomine	MeSH
Molsidomine normon brand	MeSH
Molsidominratiopharm	MeSH
Stadapharm brand OF molsidomine	MeSH
CT Arzneimittel brand OF molsidomine	MeSH
1a Brand OF molsidomine	MeSH
Azupharma brand OF molsidomine	MeSH
Molsidomine ratiopharm brand	MeSH
Normon brand OF molsidomine	MeSH
Schwarz brand OF molsidomine	MeSH
Molsidomine	MeSH
Molsidomine aventis brand	MeSH
Molsidomine salutas brand	MeSH
Molsidomine schwarz brand	MeSH
Molsidomine CT-arzneimittel brand	MeSH
Sanol brand OF molsidomine	MeSH
CT-Arzneimittel brand OF molsidomine	MeSH
Hexal brand OF molsidomine	MeSH
Merck dura brand OF molsidomine	MeSH
Molsidomine heumann brand	MeSH
Molsidomine stadapharm brand	MeSH
Salutas brand OF molsidomine	MeSH
Heumann brand OF molsidomine	MeSH
Molsidomine betapharm brand	MeSH
Aventis brand OF molsidomine	MeSH
Molsidomine azupharma brand	MeSH
Molsidomine hexal brand	MeSH
Molsidomine MTW brand	MeSH
Betapharm brand OF molsidomine	MeSH
Ratiopharm brand OF molsidomine	MeSH
MTW Brand OF molsidomine	MeSH
Molsidomine 1a brand	MeSH
Molsidomine alpharma brand	MeSH
Molsidomine sanol brand	MeSH
Ethyl N-[3-(morpholin-4-yl)-5H-1,2,3λ⁵-oxadiazol-5-ylidene]carbamic acid	Generator

Chemical Formula

C₉H₁₄N₄O₄

Average Molecular Weight

242.235

Monoisotopic Molecular Weight

242.101504947

IUPAC Name

5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ⁵-oxadiazol-3-ylium

Traditional Name

5-[(ethoxycarbonyl)azanidyl]-3-(morpholin-4-yl)-1,2,3λ⁵-oxadiazol-3-ylium

CAS Registry Number

Not Available

SMILES

CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1

InChI Identifier

InChI=1S/C9H14N4O4/c1-2-16-9(14)10-8-7-13(11-17-8)12-3-5-15-6-4-12/h7H,2-6H2,1H3

InChI Key

XLFWDASMENKTKL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Morpholines

Alternative Parents

Substituents

Morpholine
Carbonic acid derivative
Dialkyl ether
Ether
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.99 m³·mol⁻¹	ChemAxon
Polarizability	23.74 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	151.436	30932474
DeepCCS	[M-H]-	149.041	30932474
DeepCCS	[M-2H]-	181.924	30932474
DeepCCS	[M+Na]+	157.349	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	149.8	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.0	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	155.6	32859911
AllCCS	[M+HCOO]-	155.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate	CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1	2681.4	Standard polar	33892256
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate	CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1	1971.4	Standard non polar	33892256
1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate	CCOC(=O)[N-]C1=C[N+](=NO1)N1CCOCC1	1948.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01dj-7910000000-63f8ea7ee27b88f0912f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 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 - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 10V, Positive-QTOF	splash10-0006-6490000000-c5e4bc21cb85b4e60a70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 20V, Positive-QTOF	splash10-000j-9220000000-abafa3380cf8a5a4d0bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 40V, Positive-QTOF	splash10-000l-9400000000-daea7c7e4e6043483506	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 10V, Negative-QTOF	splash10-0006-5290000000-6d4f7dd885c9fb6c59ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 20V, Negative-QTOF	splash10-002n-9560000000-93fecea706c4877048ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate 40V, Negative-QTOF	splash10-052v-9000000000-a53b47a7b42292d341b5	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09282

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Molsidomine

METLIN ID

Not Available

PubChem Compound

4238

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate (HMDB0245703)

MOL for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

3D MOL for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

3D SDF for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

3D-SDF for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

PDB for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

3D PDB for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

SMILES for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

INCHI for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

Structure for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

3D Structure for HMDB0245703 (1-Ethoxy-N-(3-morpholin-4-yloxadiazol-3-ium-5-yl)methanimidate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra