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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:35:19 UTC

Update Date

2021-09-26 23:04:14 UTC

HMDB ID

HMDB0251940

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Esaprazole

Description

Esaprazole, also known as hexaprazol, belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Esaprazole is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Esaprazole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Esaprazole 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

HMDB0251940
     RDKit          3D
Esaprazole
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.0925    1.0446   -1.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599    0.2980   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    0.6405   -1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -0.1951   -0.7347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152    0.2591   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0968    1.3079   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5919    0.6208    0.9670 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863   -0.4780    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852   -0.1659    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -0.6651   -0.2025 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.9862    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -1.3027   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -0.5905   -1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4541   -0.0292    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005   -0.2292    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    0.1415    0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116    1.2624   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283    0.5208   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    1.7203   -1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -0.5794   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.7028   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    1.9767    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8896    1.9187   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    0.2803    0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -0.7039    2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0070   -1.4192    0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -0.9398    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    0.8097    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -1.8791    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023   -1.1311   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -2.4111   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.2426   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.2660   -1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    1.0840   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4926   -0.4405    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -1.2622    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.5251    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.1081    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.2102    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9  4  1  0
 16 11  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END

  Mrv1572004221605082D          

 16 17  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14 11  1  4  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251940

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CN1CCNCC1)=NC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C12H23N3O/c16-12(10-15-8-6-13-7-9-15)14-11-4-2-1-3-5-11/h11,13H,1-10H2,(H,14,16)

> <INCHI_KEY>
RTFADALJKSFJDZ-UHFFFAOYSA-N

> <FORMULA>
C12H23N3O

> <MOLECULAR_WEIGHT>
225.336

> <EXACT_MASS>
225.184112373

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.961428608544765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-cyclohexyl-2-(piperazin-1-yl)ethanimidic acid

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
-1.3146061666429887

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9485949359820833

> <JCHEM_PKA_STRONGEST_BASIC>
9.22339174278562

> <JCHEM_POLAR_SURFACE_AREA>
47.86

> <JCHEM_REFRACTIVITY>
65.08290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-cyclohexyl-2-(piperazin-1-yl)ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251940
     RDKit          3D
Esaprazole
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.0925    1.0446   -1.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599    0.2980   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    0.6405   -1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -0.1951   -0.7347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152    0.2591   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0968    1.3079   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5919    0.6208    0.9670 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863   -0.4780    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852   -0.1659    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -0.6651   -0.2025 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.9862    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -1.3027   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -0.5905   -1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4541   -0.0292    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005   -0.2292    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    0.1415    0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116    1.2624   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283    0.5208   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    1.7203   -1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -0.5794   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.7028   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    1.9767    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8896    1.9187   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    0.2803    0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -0.7039    2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0070   -1.4192    0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -0.9398    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    0.8097    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -1.8791    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023   -1.1311   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -2.4111   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.2426   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.2660   -1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    1.0840   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4926   -0.4405    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -1.2622    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.5251    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.1081    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.2102    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9  4  1  0
 16 11  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      10.669  10.780   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       8.002   6.160   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       8.002   9.240   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    8   13                                                       
CONECT    7    9   13                                                       
CONECT    8    6   15                                                       
CONECT    9    7   15                                                       
CONECT   10   12   15                                                       
CONECT   11    4    5   14                                                  
CONECT   12   10   14   16                                                  
CONECT   13    6    7                                                       
CONECT   14   11   12                                                       
CONECT   15    8    9   10                                                  
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0251940
HETATM    1  O1  UNL     1       1.093   1.045  -1.533  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.060   0.298  -0.993  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.316   0.641  -1.349  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.305  -0.195  -0.735  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.615   0.259  -1.176  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.097   1.308  -0.227  1.00  0.00           C  
HETATM    7  N2  UNL     1      -4.592   0.621   0.967  1.00  0.00           N  
HETATM    8  C5  UNL     1      -3.686  -0.478   1.221  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.285  -0.166   0.697  1.00  0.00           C  
HETATM   10  N3  UNL     1       0.342  -0.665  -0.202  1.00  0.00           N  
HETATM   11  C7  UNL     1       1.715  -0.986   0.136  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.550  -1.303  -1.051  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.824  -0.590  -1.196  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.454  -0.029   0.011  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.701  -0.229   1.288  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.244   0.142   0.981  1.00  0.00           C  
HETATM   17  H1  UNL     1       1.212   1.262  -2.498  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.428   0.521  -2.455  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.465   1.720  -1.145  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.332  -0.579  -1.272  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.525   0.703  -2.195  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.288   1.977   0.076  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.890   1.919  -0.695  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.558   0.280   0.707  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.673  -0.704   2.295  1.00  0.00           H  
HETATM   26  H10 UNL     1      -4.007  -1.419   0.697  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.603  -0.940   1.142  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.923   0.810   1.050  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.649  -1.879   0.826  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.902  -1.131  -1.963  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.742  -2.411  -1.071  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.690   0.243  -1.950  1.00  0.00           H  
HETATM   33  H17 UNL     1       4.578  -1.266  -1.701  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.631   1.084  -0.083  1.00  0.00           H  
HETATM   35  H19 UNL     1       5.493  -0.440   0.186  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.741  -1.262   1.675  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.051   0.525   2.023  1.00  0.00           H  
HETATM   38  H22 UNL     1       2.274   1.108   0.483  1.00  0.00           H  
HETATM   39  H23 UNL     1       1.644   0.210   1.894  1.00  0.00           H  
CONECT    1    2   17
CONECT    2    3   10   10
CONECT    3    4   18   19
CONECT    4    5    9
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   27   28
CONECT   10   11
CONECT   11   12   16   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   36   37
CONECT   16   38   39
END

HMDB0251940
     RDKit          3D
Esaprazole
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.0925    1.0446   -1.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599    0.2980   -0.9932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163    0.6405   -1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -0.1951   -0.7347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152    0.2591   -1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0968    1.3079   -0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5919    0.6208    0.9670 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863   -0.4780    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2852   -0.1659    0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -0.6651   -0.2025 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7152   -0.9862    0.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -1.3027   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -0.5905   -1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4541   -0.0292    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005   -0.2292    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    0.1415    0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2116    1.2624   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283    0.5208   -2.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4648    1.7203   -1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -0.5794   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.7028   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    1.9767    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8896    1.9187   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    0.2803    0.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6730   -0.7039    2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0070   -1.4192    0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030   -0.9398    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    0.8097    1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -1.8791    0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023   -1.1311   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -2.4111   -1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.2426   -1.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779   -1.2660   -1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    1.0840   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4926   -0.4405    0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -1.2622    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.5251    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.1081    0.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444    0.2102    1.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  2  3
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9  4  1  0
 16 11  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Esaprazole monohydrochloride	MeSH
N-((N-Cyclohexylcarbamoyl)methyl)piperazine	MeSH
Hexaprazol	MeSH

Chemical Formula

C₁₂H₂₃N₃O

Average Molecular Weight

225.336

Monoisotopic Molecular Weight

225.184112373

IUPAC Name

N-cyclohexyl-2-(piperazin-1-yl)ethanimidic acid

Traditional Name

N-cyclohexyl-2-(piperazin-1-yl)ethanimidic acid

CAS Registry Number

Not Available

SMILES

OC(CN1CCNCC1)=NC1CCCCC1

InChI Identifier

InChI=1S/C12H23N3O/c16-12(10-15-8-6-13-7-9-15)14-11-4-2-1-3-5-11/h11,13H,1-10H2,(H,14,16)

InChI Key

RTFADALJKSFJDZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
N-piperazineacetamide
N-alkylpiperazine
1,4-diazinane
Piperazine
Carboxamide group
Secondary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Secondary aliphatic amine
Secondary amine
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Carbonyl group
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)

Source

Exogenous

Exogenous (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	0.31	ALOGPS
logP	-1.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	47.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.08 m³·mol⁻¹	ChemAxon
Polarizability	25.96 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]+	154.026	30932474
DeepCCS	[M-H]-	151.605	30932474
DeepCCS	[M-2H]-	186.792	30932474
DeepCCS	[M+Na]+	161.591	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	157.2	32859911
AllCCS	[M+Na]+	158.2	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	157.7	32859911
AllCCS	[M+HCOO]-	158.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Esaprazole	OC(CN1CCNCC1)=NC1CCCCC1	1998.2	Standard polar	33892256
Esaprazole	OC(CN1CCNCC1)=NC1CCCCC1	1958.4	Standard non polar	33892256
Esaprazole	OC(CN1CCNCC1)=NC1CCCCC1	1978.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Esaprazole,2TMS,isomer #1	C[Si](C)(C)OC(CN1CCN([Si](C)(C)C)CC1)=NC1CCCCC1	2099.5	Semi standard non polar	33892256
Esaprazole,2TMS,isomer #1	C[Si](C)(C)OC(CN1CCN([Si](C)(C)C)CC1)=NC1CCCCC1	2079.1	Standard non polar	33892256
Esaprazole,2TMS,isomer #1	C[Si](C)(C)OC(CN1CCN([Si](C)(C)C)CC1)=NC1CCCCC1	2972.9	Standard polar	33892256
Esaprazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1CCN([Si](C)(C)C(C)(C)C)CC1)=NC1CCCCC1	2506.5	Semi standard non polar	33892256
Esaprazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1CCN([Si](C)(C)C(C)(C)C)CC1)=NC1CCCCC1	2429.8	Standard non polar	33892256
Esaprazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1CCN([Si](C)(C)C(C)(C)C)CC1)=NC1CCCCC1	3090.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Esaprazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-003v-9400000000-8cd38aedae4d2d9e4fb9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esaprazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esaprazole GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esaprazole GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esaprazole GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Esaprazole GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Esaprazole 10V, Positive-QTOF	splash10-0002-9010000000-174c3da6e847abc0da68	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 20V, Positive-QTOF	splash10-0002-9000000000-b2ee3d37f7190c1d4a25	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 40V, Positive-QTOF	splash10-05fu-9000000000-71d6b49762be7bf75ab0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 10V, Negative-QTOF	splash10-00di-1190000000-74ad9f4016e046b80161	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 20V, Negative-QTOF	splash10-00dj-9560000000-4999f42fcbf25a86810d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 40V, Negative-QTOF	splash10-0007-9000000000-bad6aa23b36961f176d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 10V, Positive-QTOF	splash10-004i-0090000000-f1d93e7cbe1a25addf7b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 20V, Positive-QTOF	splash10-004i-1190000000-65c890d35290e42a5197	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 40V, Positive-QTOF	splash10-0002-9200000000-aa3fe311ca6ee98165be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 10V, Negative-QTOF	splash10-00di-0090000000-cfa62e996d95535b0a69	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 20V, Negative-QTOF	splash10-00dj-7290000000-70367c500b3e3517f246	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Esaprazole 40V, Negative-QTOF	splash10-0007-9300000000-78df514b3f37c0777152	2021-10-12	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	¹³C NMR Spectrum (1D, 1000 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, 200 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	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	¹H NMR Spectrum (1D, 400 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, 500 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	¹³C NMR Spectrum (1D, 600 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	¹H NMR Spectrum (1D, 700 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	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	¹H NMR Spectrum (1D, 900 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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

68835

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 Esaprazole (HMDB0251940)

MOL for HMDB0251940 (Esaprazole)

3D MOL for HMDB0251940 (Esaprazole)

3D SDF for HMDB0251940 (Esaprazole)

3D-SDF for HMDB0251940 (Esaprazole)

PDB for HMDB0251940 (Esaprazole)

3D PDB for HMDB0251940 (Esaprazole)

SMILES for HMDB0251940 (Esaprazole)

INCHI for HMDB0251940 (Esaprazole)

Structure for HMDB0251940 (Esaprazole)

3D Structure for HMDB0251940 (Esaprazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra