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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:00:16 UTC

Update Date

2021-09-26 23:17:51 UTC

HMDB ID

HMDB0259981

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zacopride

Description

4-amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzene-1-carboximidic acid belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring. Based on a literature review very few articles have been published on 4-amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzene-1-carboximidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zacopride is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Zacopride 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

HMDB0259981
     RDKit          3D
Zacopride
 41 43  0  0  0  0  0  0  0  0999 V2000
    2.5670    1.9486   -1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348    1.0490   -0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6568    0.1428   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442    0.1707   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351   -0.6986    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602   -0.6597    0.1491 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2499   -1.5851    1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -2.6986    2.0591 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -1.6126    1.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -0.7334    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -0.7770    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -1.6894    1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    0.0221    0.2165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -0.1903    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4111    1.0349    1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8420    0.9015    0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    1.3560   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.6830   -1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501   -0.5729   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7785   -1.3153   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502   -0.4863    1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    1.4661   -2.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    2.6975   -2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    2.5704   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005    0.8775   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -0.2138   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953   -1.0679    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3291    2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    0.7576   -0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -1.0062    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    1.0591    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0712    1.9675    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1037    1.0403   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0499    2.4408   -0.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.3958   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144    0.3464   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718   -1.1827   -1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5628   -1.4071   -0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3984   -2.2885    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7887   -0.8705    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3353   -0.5426    1.1245 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  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 10  3  1  0
 19 14  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END


  Mrv1533004241523542D          

 21 23  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  6 20  1  0  0  0  0
  5 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259981

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20)

> <INCHI_KEY>
FEROPKNOYKURCJ-UHFFFAOYSA-N

> <FORMULA>
C15H20ClN3O2

> <MOLECULAR_WEIGHT>
309.79

> <EXACT_MASS>
309.1244046

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.25218519672026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzamide

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.0406586349999998

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.770478570588427

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.591333155834501

> <JCHEM_PKA_STRONGEST_BASIC>
7.788264252618395

> <JCHEM_POLAR_SURFACE_AREA>
67.59

> <JCHEM_REFRACTIVITY>
83.97179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zacopride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259981
     RDKit          3D
Zacopride
 41 43  0  0  0  0  0  0  0  0999 V2000
    2.5670    1.9486   -1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348    1.0490   -0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6568    0.1428   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442    0.1707   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351   -0.6986    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602   -0.6597    0.1491 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2499   -1.5851    1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -2.6986    2.0591 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -1.6126    1.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -0.7334    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -0.7770    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -1.6894    1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    0.0221    0.2165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -0.1903    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4111    1.0349    1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8420    0.9015    0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    1.3560   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.6830   -1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501   -0.5729   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7785   -1.3153   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502   -0.4863    1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    1.4661   -2.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    2.6975   -2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    2.5704   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005    0.8775   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -0.2138   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953   -1.0679    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3291    2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    0.7576   -0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -1.0062    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    1.0591    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0712    1.9675    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1037    1.0403   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0499    2.4408   -0.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.3958   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144    0.3464   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718   -1.1827   -1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5628   -1.4071   -0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3984   -2.2885    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7887   -0.8705    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3353   -0.5426    1.1245 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  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 10  3  1  0
 19 14  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.590   0.257   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.590   1.283   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -6.668  -2.310   0.000  0.00  0.00          Cl+0
HETATM   21  N   UNK     0      -6.668  -5.390   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    6                                                            
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0259981
HETATM    1  C1  UNL     1       2.567   1.949  -1.792  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.935   1.049  -0.929  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.657   0.143  -0.198  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.044   0.171  -0.363  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.835  -0.699   0.328  1.00  0.00           C  
HETATM    6  N1  UNL     1       6.260  -0.660   0.149  1.00  0.00           N  
HETATM    7  C5  UNL     1       4.250  -1.585   1.175  1.00  0.00           C  
HETATM    8 CL1  UNL     1       5.276  -2.699   2.059  1.00  0.00          CL  
HETATM    9  C6  UNL     1       2.881  -1.613   1.338  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.041  -0.733   0.643  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.621  -0.777   0.826  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.222  -1.689   1.676  1.00  0.00           O  
HETATM   13  N2  UNL     1      -0.367   0.022   0.217  1.00  0.00           N  
HETATM   14  C9  UNL     1      -1.742  -0.190   0.545  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.411   1.035   1.120  1.00  0.00           C  
HETATM   16  N3  UNL     1      -3.842   0.902   0.876  1.00  0.00           N  
HETATM   17  C11 UNL     1      -4.097   1.356  -0.493  1.00  0.00           C  
HETATM   18  C12 UNL     1      -3.056   0.683  -1.377  1.00  0.00           C  
HETATM   19  C13 UNL     1      -2.550  -0.573  -0.701  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.778  -1.315  -0.168  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.250  -0.486   1.032  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.120   1.466  -2.621  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.825   2.697  -2.180  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.338   2.570  -1.250  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.501   0.877  -1.037  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.676  -0.214  -0.696  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.895  -1.068   0.846  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.439  -2.329   2.019  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.145   0.758  -0.459  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.823  -1.006   1.277  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.285   1.059   2.223  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.071   1.967   0.625  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.104   1.040  -0.833  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.050   2.441  -0.560  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.239   1.396  -1.596  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.514   0.346  -2.349  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.972  -1.183  -1.394  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.563  -1.407  -0.923  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.398  -2.288   0.208  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.789  -0.871   1.956  1.00  0.00           H  
HETATM   41  H20 UNL     1      -5.335  -0.543   1.125  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26   27
CONECT    7    8    9
CONECT    9   10   10   28
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   29
CONECT   14   15   19   30
CONECT   15   16   31   32
CONECT   16   17   21
CONECT   17   18   33   34
CONECT   18   19   35   36
CONECT   19   20   37
CONECT   20   21   38   39
CONECT   21   40   41
END

HMDB0259981
     RDKit          3D
Zacopride
 41 43  0  0  0  0  0  0  0  0999 V2000
    2.5670    1.9486   -1.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9348    1.0490   -0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6568    0.1428   -0.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442    0.1707   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8351   -0.6986    0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602   -0.6597    0.1491 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2499   -1.5851    1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -2.6986    2.0591 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -1.6126    1.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413   -0.7334    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -0.7770    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -1.6894    1.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    0.0221    0.2165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -0.1903    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4111    1.0349    1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8420    0.9015    0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    1.3560   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0561    0.6830   -1.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501   -0.5729   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7785   -1.3153   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502   -0.4863    1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1201    1.4661   -2.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8254    2.6975   -2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    2.5704   -1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005    0.8775   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6762   -0.2138   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953   -1.0679    0.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -2.3291    2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1446    0.7576   -0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -1.0062    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    1.0591    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0712    1.9675    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1037    1.0403   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0499    2.4408   -0.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.3958   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144    0.3464   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718   -1.1827   -1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5628   -1.4071   -0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3984   -2.2885    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7887   -0.8705    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3353   -0.5426    1.1245 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  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 10  3  1  0
 19 14  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzene-1-carboximidate	Generator

Chemical Formula

C₁₅H₂₀ClN₃O₂

Average Molecular Weight

309.79

Monoisotopic Molecular Weight

309.1244046

IUPAC Name

4-amino-N-{1-azabicyclo[2.2.2]octan-3-yl}-5-chloro-2-methoxybenzamide

Traditional Name

zacopride

CAS Registry Number

Not Available

SMILES

COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2

InChI Identifier

InChI=1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20)

InChI Key

FEROPKNOYKURCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Methoxybenzene
Aniline or substituted anilines
Quinuclidine
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboximidic acid
Carboximidic acid derivative
Organoheterocyclic compound
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.94	ALOGPS
logP	1.04	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	7.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.97 m³·mol⁻¹	ChemAxon
Polarizability	32.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	170.442	32859911
AllCCS	[M+H-H2O]+	167.264	32859911
AllCCS	[M+Na]+	174.228	32859911
AllCCS	[M+NH4]+	173.384	32859911
AllCCS	[M-H]-	171.773	32859911
AllCCS	[M+Na-2H]-	171.818	32859911
AllCCS	[M+HCOO]-	171.988	32859911
DeepCCS	[M+H]+	171.337	30932474
DeepCCS	[M-H]-	168.979	30932474
DeepCCS	[M-2H]-	201.865	30932474
DeepCCS	[M+Na]+	177.431	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zacopride	COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3107.4	Standard polar	33892256
Zacopride	COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2659.6	Standard non polar	33892256
Zacopride	COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2924.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zacopride,1TMS,isomer #1	COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2872.1	Semi standard non polar	33892256
Zacopride,1TMS,isomer #1	COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2534.0	Standard non polar	33892256
Zacopride,1TMS,isomer #1	COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3820.9	Standard polar	33892256
Zacopride,1TMS,isomer #2	COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	2669.9	Semi standard non polar	33892256
Zacopride,1TMS,isomer #2	COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	2491.2	Standard non polar	33892256
Zacopride,1TMS,isomer #2	COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	3764.2	Standard polar	33892256
Zacopride,2TMS,isomer #1	COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2755.2	Semi standard non polar	33892256
Zacopride,2TMS,isomer #1	COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2638.2	Standard non polar	33892256
Zacopride,2TMS,isomer #1	COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3683.2	Standard polar	33892256
Zacopride,2TMS,isomer #2	COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	2728.8	Semi standard non polar	33892256
Zacopride,2TMS,isomer #2	COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	2520.5	Standard non polar	33892256
Zacopride,2TMS,isomer #2	COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	3337.5	Standard polar	33892256
Zacopride,3TMS,isomer #1	COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	2637.1	Semi standard non polar	33892256
Zacopride,3TMS,isomer #1	COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	2627.0	Standard non polar	33892256
Zacopride,3TMS,isomer #1	COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C	3188.9	Standard polar	33892256
Zacopride,1TBDMS,isomer #1	COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3078.2	Semi standard non polar	33892256
Zacopride,1TBDMS,isomer #1	COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2756.7	Standard non polar	33892256
Zacopride,1TBDMS,isomer #1	COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3895.1	Standard polar	33892256
Zacopride,1TBDMS,isomer #2	COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	2883.3	Semi standard non polar	33892256
Zacopride,1TBDMS,isomer #2	COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	2682.0	Standard non polar	33892256
Zacopride,1TBDMS,isomer #2	COC1=CC(N)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	3832.9	Standard polar	33892256
Zacopride,2TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3187.8	Semi standard non polar	33892256
Zacopride,2TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	2996.8	Standard non polar	33892256
Zacopride,2TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)NC1CN2CCC1CC2	3709.4	Standard polar	33892256
Zacopride,2TBDMS,isomer #2	COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	3118.5	Semi standard non polar	33892256
Zacopride,2TBDMS,isomer #2	COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	2896.1	Standard non polar	33892256
Zacopride,2TBDMS,isomer #2	COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	3484.7	Standard polar	33892256
Zacopride,3TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	3256.6	Semi standard non polar	33892256
Zacopride,3TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	3171.3	Standard non polar	33892256
Zacopride,3TBDMS,isomer #1	COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N(C1CN2CCC1CC2)[Si](C)(C)C(C)(C)C	3385.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zacopride GC-MS (Non-derivatized) - 70eV, Positive	splash10-08gr-2910000000-2cda421d5a8440308e46	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zacopride 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zacopride 35V, Positive-QTOF	splash10-03e9-0906000000-aa8637b0b5ae5960082c	2021-09-20	HMDB team, MONA	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

97262

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Zacopride (HMDB0259981)

MOL for HMDB0259981 (Zacopride)

3D MOL for HMDB0259981 (Zacopride)

3D SDF for HMDB0259981 (Zacopride)

3D-SDF for HMDB0259981 (Zacopride)

PDB for HMDB0259981 (Zacopride)

3D PDB for HMDB0259981 (Zacopride)

SMILES for HMDB0259981 (Zacopride)

INCHI for HMDB0259981 (Zacopride)

Structure for HMDB0259981 (Zacopride)

3D Structure for HMDB0259981 (Zacopride)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra