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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (2) Show 3 proteins XML

enzymes (1)transporters (2) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014718

Secondary Accession Numbers

HMDB14718

Metabolite Identification

Common Name

Mazindol

Description

Mazindol is only found in individuals that have used or taken this drug. It is a tricyclic anorexigenic agent unrelated to and less toxic than amphetamine, but with some similar side effects. It inhibits uptake of catecholamines and blocks the binding of cocaine to the dopamine uptake transporter. [PubChem]Although the mechanism of action of the sympathomimetics in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Unlike other sympathomimetic appetite suppressants such as phentermine, mazindol is thought to inhibit the reuptake of norepinephrine rather than to cause its release.

Structure

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

HMDB0014718
     RDKit          3D
Mazindol
 33 36  0  0  0  0  0  0  0  0999 V2000
    0.5446    0.0754   -2.1448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1812   -0.0674   -0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.1165    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856    1.0870   -0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730    1.3425    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668    0.6068    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516    0.8958    2.3373 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -0.3564    1.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7371   -0.5860    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647    0.9117   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584    2.3133   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    3.0358   -0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1926    2.3877    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    1.0115    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0487    0.2899   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783   -1.1610   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -2.2461   -0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -3.3648   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388   -2.8054   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -1.3408   -0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923    0.1261   -2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    1.7072   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    2.1029   -0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0809   -0.9587    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -1.3382    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    2.7771   -0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    4.1214   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0494    2.9924    0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1271    0.5079    0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -3.9342   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -4.0389    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -3.1042   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -3.1066   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  9  3  1  0
 15 10  1  0
 20 16  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 18 31  1  0
 19 32  1  0
 19 33  1  0
M  END

579
  Mrv0541 02231214472D          

 20 23  0  0  1  0            999 V2000
    7.2861    1.3858    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1476    1.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4025   -0.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -1.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1476    0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3226    0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0648   -0.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0676   -0.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322    0.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575    1.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2299   -0.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1037    1.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5453    0.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156    0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8884    1.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3299    0.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5014    1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  5  1  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 13  2  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 16 17  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014718

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1(N2CCN=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2

> <INCHI_KEY>
ZPXSCAKFGYXMGA-UHFFFAOYSA-N

> <FORMULA>
C16H13ClN2O

> <MOLECULAR_WEIGHT>
284.74

> <EXACT_MASS>
284.071640755

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.42307409582678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(4-chlorophenyl)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.4352790006666662

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.613320052308882

> <JCHEM_PKA_STRONGEST_BASIC>
3.8591774103953047

> <JCHEM_POLAR_SURFACE_AREA>
35.83

> <JCHEM_REFRACTIVITY>
79.42210000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mazindol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014718
     RDKit          3D
Mazindol
 33 36  0  0  0  0  0  0  0  0999 V2000
    0.5446    0.0754   -2.1448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1812   -0.0674   -0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.1165    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856    1.0870   -0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730    1.3425    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668    0.6068    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516    0.8958    2.3373 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -0.3564    1.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7371   -0.5860    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647    0.9117   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584    2.3133   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    3.0358   -0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1926    2.3877    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    1.0115    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0487    0.2899   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783   -1.1610   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -2.2461   -0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -3.3648   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388   -2.8054   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -1.3408   -0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923    0.1261   -2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    1.7072   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    2.1029   -0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0809   -0.9587    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -1.3382    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    2.7771   -0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    4.1214   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0494    2.9924    0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1271    0.5079    0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -3.9342   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -4.0389    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -3.1042   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -3.1066   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  9  3  1  0
 15 10  1  0
 20 16  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 18 31  1  0
 19 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 579                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      13.601   2.587   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.742   2.223   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.218  -0.781   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.449  -3.141   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.742   0.683   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.202   0.683   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.972  -1.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.454  -1.684   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.726  -0.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.207   1.159   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.980  -3.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.147   1.892   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.162  -1.139   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.527   2.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.351   0.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.576   1.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   0.045   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.992   3.141   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.816   0.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.136   2.111   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    5                                                            
CONECT    3    5    7    8                                                  
CONECT    4    7   11                                                       
CONECT    5    2    3    6   10                                             
CONECT    6    5    9   12                                                  
CONECT    7    3    4    9                                                  
CONECT    8    3   11                                                       
CONECT    9    6    7   13                                                  
CONECT   10    5   14   15                                                  
CONECT   11    4    8                                                       
CONECT   12    6   16                                                       
CONECT   13    9   17                                                       
CONECT   14   10   18                                                       
CONECT   15   10   19                                                       
CONECT   16   12   17                                                       
CONECT   17   13   16                                                       
CONECT   18   14   20                                                       
CONECT   19   15   20                                                       
CONECT   20    1   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0014718
HETATM    1  O1  UNL     1       0.545   0.075  -2.145  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.181  -0.067  -0.780  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.401   0.116   0.021  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.286   1.087  -0.401  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.473   1.342   0.295  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.767   0.607   1.430  1.00  0.00           C  
HETATM    7 CL1  UNL     1       5.252   0.896   2.337  1.00  0.00          CL  
HETATM    8  C6  UNL     1       2.899  -0.356   1.857  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.737  -0.586   1.152  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.865   0.912  -0.502  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.858   2.313  -0.476  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.989   3.036  -0.177  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.193   2.388   0.115  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.204   1.012   0.091  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.049   0.290  -0.215  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.778  -1.161  -0.317  1.00  0.00           C  
HETATM   17  N1  UNL     1      -2.440  -2.246  -0.172  1.00  0.00           N  
HETATM   18  C15 UNL     1      -1.590  -3.365  -0.415  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.239  -2.805  -0.762  1.00  0.00           C  
HETATM   20  N2  UNL     1      -0.430  -1.341  -0.665  1.00  0.00           N  
HETATM   21  H1  UNL     1      -0.292   0.126  -2.704  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.140   1.707  -1.275  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.169   2.103  -0.033  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.081  -0.959   2.735  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.060  -1.338   1.487  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.087   2.777  -0.707  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.923   4.121  -0.172  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.049   2.992   0.343  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.127   0.508   0.315  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.039  -3.934  -1.281  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.552  -4.039   0.477  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.550  -3.104  -0.045  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.009  -3.107  -1.797  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3   10   20
CONECT    3    4    4    9
CONECT    4    5   22
CONECT    5    6    6   23
CONECT    6    7    8
CONECT    8    9    9   24
CONECT    9   25
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   17   20
CONECT   17   18
CONECT   18   19   30   31
CONECT   19   20   32   33
END

HMDB0014718
     RDKit          3D
Mazindol
 33 36  0  0  0  0  0  0  0  0999 V2000
    0.5446    0.0754   -2.1448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1812   -0.0674   -0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.1165    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2856    1.0870   -0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730    1.3425    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668    0.6068    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516    0.8958    2.3373 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -0.3564    1.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7371   -0.5860    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8647    0.9117   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8584    2.3133   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    3.0358   -0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1926    2.3877    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037    1.0115    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0487    0.2899   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7783   -1.1610   -0.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -2.2461   -0.1717 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -3.3648   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388   -2.8054   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4303   -1.3408   -0.6652 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923    0.1261   -2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1404    1.7072   -1.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1690    2.1029   -0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0809   -0.9587    2.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -1.3382    1.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869    2.7771   -0.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    4.1214   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0494    2.9924    0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1271    0.5079    0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388   -3.9342   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5518   -4.0389    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -3.1042   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -3.1066   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  9  3  1  0
 15 10  1  0
 20 16  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
 18 31  1  0
 19 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sanorex	Kegg
Mazindol wyeth brand	HMDB
Medix brand OF mazindol	HMDB
Mazanor	HMDB
Mazindol searle brand	HMDB
Novartis brand OF mazindol	HMDB
Sanjorex	HMDB
Teronac	HMDB
Diestet	HMDB
Mazindol medix brand	HMDB
Searle brand OF mazindol	HMDB
Teronak	HMDB
Mazindol novartis brand	HMDB
Mazindole	HMDB
Solucaps	HMDB
Wyeth brand OF mazindol	HMDB

Chemical Formula

C₁₆H₁₃ClN₂O

Average Molecular Weight

284.74

Monoisotopic Molecular Weight

284.071640755

IUPAC Name

5-(4-chlorophenyl)-2H,3H,5H-imidazo[2,1-a]isoindol-5-ol

Traditional Name

mazindol

CAS Registry Number

22232-71-9

SMILES

OC1(N2CCN=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2

InChI Key

ZPXSCAKFGYXMGA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindoline
Isoindole
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Imidolactam
Benzenoid
2-imidazoline
Alkanolamine
Amidine
Carboxylic acid amidine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.64	ALOGPS
logP	3.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	3.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.42 m³·mol⁻¹	ChemAxon
Polarizability	29.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	193.939	30932474
DeepCCS	[M+Na]+	169.505	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	168.9	32859911
AllCCS	[M-H]-	167.9	32859911
AllCCS	[M+Na-2H]-	167.1	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.13 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0302 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	35.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1772.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	156.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	474.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	455.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	67.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1012.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	428.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1252.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	115.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mazindol	OC1(N2CCN=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1	3489.6	Standard polar	33892256
Mazindol	OC1(N2CCN=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1	2360.7	Standard non polar	33892256
Mazindol	OC1(N2CCN=C2C2=CC=CC=C12)C1=CC=C(Cl)C=C1	2536.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mazindol,1TMS,isomer #1	C[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)C2=CC=CC=C2C2=NCCN21	2458.1	Semi standard non polar	33892256
Mazindol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1(C2=CC=C(Cl)C=C2)C2=CC=CC=C2C2=NCCN21	2663.1	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 - Mazindol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3920000000-014167a19bc06d4b57ce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mazindol GC-MS (1 TMS) - 70eV, Positive	splash10-014i-3090000000-fc6fdc778249a1f313a6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mazindol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-0390000000-2514253f04060882685b	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 10V, Positive-QTOF	splash10-000i-0090000000-d3dc6820d6c6134b2013	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 20V, Positive-QTOF	splash10-000i-0390000000-3cdf028f902955c380fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 40V, Positive-QTOF	splash10-01vo-5920000000-5efd9a158e2afed55e22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 10V, Negative-QTOF	splash10-001i-0090000000-ae73b97007675d68826b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 20V, Negative-QTOF	splash10-001i-0190000000-7ab5be67a229e84bec41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 40V, Negative-QTOF	splash10-014l-2920000000-13bafaed87a47c8871a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 10V, Positive-QTOF	splash10-000i-0090000000-467b34577c9cf5fb314a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 20V, Positive-QTOF	splash10-000i-0090000000-884c24d87555dd9b139f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 40V, Positive-QTOF	splash10-01ox-0790000000-181f37bd2b8a9227e5ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 10V, Negative-QTOF	splash10-001i-0090000000-ccaa52cef887c66f191b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 20V, Negative-QTOF	splash10-001i-4090000000-4b24fa7d85c7759e56cc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mazindol 40V, Negative-QTOF	splash10-001i-5890000000-ed80b0de920491d0799e	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00579	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00579	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00579

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3880

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mazindol

METLIN ID

Not Available

PubChem Compound

4020

PDB ID

Not Available

ChEBI ID

146385

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

Not Available

Enzymes

Enzyme Details

1. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Itzhak Y, Martin JL: Effects of cocaine, nicotine, dizocipline and alcohol on mice locomotor activity: cocaine-alcohol cross-sensitization involves upregulation of striatal dopamine transporter binding sites. Brain Res. 1999 Feb 13;818(2):204-11. [PubMed:10082805 ]
Saunders C, Ferrer JV, Shi L, Chen J, Merrill G, Lamb ME, Leeb-Lundberg LM, Carvelli L, Javitch JA, Galli A: Amphetamine-induced loss of human dopamine transporter activity: an internalization-dependent and cocaine-sensitive mechanism. Proc Natl Acad Sci U S A. 2000 Jun 6;97(12):6850-5. [PubMed:10823899 ]
Goettl VM, Wemlinger TA, Fong TG, Neff NH, Hadjiconstantinou M: Retinal cholinergic and dopaminergic deficits of aged rats are improved following treatment with GM1 ganglioside. Brain Res. 2000 Sep 15;877(1):1-6. [PubMed:10980236 ]
Tidjane Corera A, Do-Rego JC, Costentin J, Bonnet JJ: Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes. Neurosci Res. 2001 Mar;39(3):319-25. [PubMed:11248372 ]
Purkerson-Parker S, McDaniel KL, Moser VC: Dopamine transporter binding in the rat striatum is increased by gestational, perinatal, and adolescent exposure to heptachlor. Toxicol Sci. 2001 Dec;64(2):216-23. [PubMed:11719704 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Kulkarni SS, Newman AH, Houlihan WJ: Three-dimensional quantitative structure-activity relationships of mazindol analogues at the dopamine transporter. J Med Chem. 2002 Sep 12;45(19):4119-27. [PubMed:12213055 ]
Houlihan WJ, Kelly L, Pankuch J, Koletar J, Brand L, Janowsky A, Kopajtic TA: Mazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter. J Med Chem. 2002 Sep 12;45(19):4097-109. [PubMed:12213053 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Raffel DM, Chen W: Binding of [3H]mazindol to cardiac norepinephrine transporters: kinetic and equilibrium studies. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):9-16. Epub 2004 Jul 22. [PubMed:15300361 ]
Raffel DM, Chen W, Sherman PS, Gildersleeve DL, Jung YW: Dependence of cardiac 11C-meta-hydroxyephedrine retention on norepinephrine transporter density. J Nucl Med. 2006 Sep;47(9):1490-6. [PubMed:16954558 ]
Zhao L, Johnson KM, Zhang M, Flippen-Anderson J, Kozikowski AP: Chemical synthesis and pharmacology of 6- and 7-hydroxylated 2-carbomethoxy-3-(p-tolyl)tropanes: antagonism of cocaine's locomotor stimulant effects. J Med Chem. 2000 Aug 24;43(17):3283-94. [PubMed:10966747 ]
Ritz MC, Boja JW, Grigoriadis D, Zaczek R, Carroll FI, Lewis AH, Kuhar MJ: [3H]WIN 35,065-2: a ligand for cocaine receptors in striatum. J Neurochem. 1990 Nov;55(5):1556-62. [PubMed:2120386 ]
Sharpe IA, Palant E, Schroeder CI, Kaye DM, Adams DJ, Alewood PF, Lewis RJ: Inhibition of the norepinephrine transporter by the venom peptide chi-MrIA. Site of action, Na+ dependence, and structure-activity relationship. J Biol Chem. 2003 Oct 10;278(41):40317-23. Epub 2003 Jul 28. [PubMed:12885787 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Showing metabocard for Mazindol (HMDB0014718)

MOL for HMDB0014718 (Mazindol)

3D MOL for HMDB0014718 (Mazindol)

3D SDF for HMDB0014718 (Mazindol)

3D-SDF for HMDB0014718 (Mazindol)

PDB for HMDB0014718 (Mazindol)

3D PDB for HMDB0014718 (Mazindol)

SMILES for HMDB0014718 (Mazindol)

INCHI for HMDB0014718 (Mazindol)

Structure for HMDB0014718 (Mazindol)

3D Structure for HMDB0014718 (Mazindol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References